Fragrance Compositions Duftstoffzusammensetzungen Compositions Parfumées

(19) TZZ _¥_T

(11) EP 2 961 374 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 8/34 (2006.01) A61K 8/37 (2006.01) 25.01.2017 Bulletin 2017/04 A61K 8/60 (2006.01) A61Q 15/00 (2006.01) A61Q 19/00 (2006.01) A61Q 19/10 (2006.01) (21) Application number: 14824649.9 (86) International application number: (22) Date of filing: 11.12.2014 PCT/US2014/069654

(87) International publication number: WO 2015/089246 (18.06.2015 Gazette 2015/24)

(54) FRAGRANCE COMPOSITIONS DUFTSTOFFZUSAMMENSETZUNGEN COMPOSITIONS PARFUMÉES

(84) Designated Contracting States: • STONEHOUSE, Jonathan, Richard AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Egham GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Surrey TW20 9NW (GB) PL PT RO RS SE SI SK SM TR • STAITE, William, Eoghan Egham (30) Priority: 13.12.2013 US 201361915514 P Surrey TW20 9NW (GB) 10.06.2014 US 201462009923 P • STANTON, David, Thomas Cincinnati, Ohio 45202 (US) (43) Date of publication of application: • TODINI, Oreste 06.01.2016 Bulletin 2016/01 1853 Brussels (BE)

(73) Proprietor: The Procter & Gamble Company (74) Representative: Kohol, Sonia Cincinnati, OH 45202 (US) Technical Centres Limited Procter & Gamble Patent Department (72) Inventors: Rusham Park • BONNET, Christelle, Marie, Sandrine Whitehall Lane 78300 Poissy (FR) Egham, Surrey TW20 9NW (GB) • HOLLAND, Lynette, Anne, Makins Egham (56) References cited: Surrey TW20 9NW (GB) WO-A1-2011/154926 WO-A1-2014/093807 • PASTOR, Fabienne WO-A2-2013/060691 WO-A2-2013/064412 78300 Poissy (FR) US-A- 4 324 703 • VELAZQUEZ MENDOZA, Jose, Maria Egham Surrey TW20 9NW (GB)

Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 961 374 B1

Printed by Jouve, 75001 PARIS (FR) EP 2 961 374 B1

Description

FIELD OF THE INVENTION

5 [0001] The present invention relates to the field of perfumery. In particular, the compositions of the present invention have improved intensity and/or longevity of the fragrance profile.

BACKGROUND OF THE INVENTION

10 [0002] It has been a long tradition that highly skilled perfumers carefully select fragrance materials to blend into a composition with the goal of achieveing an overall specific fragrance profile of strength and character. In so doing, they need to bear in mind differences in the individual character and volatility of the fragrance materials that are the components of the full fragrance. Conventional perfuming compositions have fragrance profile characterized by a high amount of the low volatile fragrance materials and lower amounts of the volatile fragrance materials. The low volatile fragrance materials 15 are known as "base notes", while the volatile fragrance materials can be further divided into high volatile fragrance materials, identified as "top or head notes", and medium volatile fragrance materials, identified as "middle or heart notes". [0003] The top notes tend to smell citrusy, green, light, fresh, and comprise typically from about 0.1 wt% to 40 wt% relative to the total weight of the perfume formulation. Top notes tend to evaporate quickly due to their high volatility and are characterized by vapor pressure > 0.1 Torr at 25°C (Calculated using Advanced Chemistry Development (ACD/Labs) 20 Software V11.02 (© 1994-2013 ACD/Labs)). Typically, perfumers use top notes to deliver the initial impression of the composition but do not rely on them to contribute much to its overall fragrance profile over time after application. [0004] Middle or heart notes make up from about 0.1 wt% to about 40 wt% relative to the total weight of the perfume formulation. Generally, they become dominant to the untrained nose from several minutes after application and can last up to a few hours afterwards. Middle notes are associated with floral aromas ( e.g., jasmin, rose), fruity, marine or spicy 25 aromas and have an intermediate volatity in the vapor pressure range of 0.001 to 0.1 Torr at 25°C. [0005] Base or bottom notes can exist at >30 wt% relative to the total weight of the perfume formulation. They are characterized as animalic, woody, sweet, amber or musky, not being very volatile and having a vapor pressure < 0.133 Pa (0.001 Torr) at 25°C. Typically, they are not perceived as dominant until several hours after the application of the perfume or during "dry-down". Base notes are relied upon to improve the strength of the overall fragrance profile over 30 time and replace the heart notes when these are declining, The consequence of using base notes at high levels is that they impart particular odour characters, such as for example, musky, woody, ambery, warm and sweet, which overpower and dominate the fragrance character over time. Some of these base notes have become such common materials ( e.g., hedione, galaxolide, etc.) that many fragrance dry-downs appear repetitive, boring, non-memorable and un-interesting to consumers. However, if base notes are reduced or excluded then the fragrance strength weakens over time and does 35 not last for a sufficient duration. [0006] To date, due to the volatility of the fragrance materials, the possible types of fragrance profiles or characters have been somewhat limited. A common complaint by consumers is that middle notes tend to fade too quickly after application of the composition and that the character of the middle notes are undesirably altered by the presence of large amounts of the base notes during the period known as the "dry-down" phase. 40 [0007] Thus, it is desirable to have a composition which retains a significant portion of its initial fragrance character over time, hence, the floral, fruity or spicy characters of the ’heart notes’ are perceived for many hours It is also desirable that the fragrance strength of the composition remains noticeable to the consumer over longer periods of time. It is further desirable to be able to create new to the world fragrance profiles wherein one, or several, well-recognized heart note characters, are maintained over time. 45 [0008] It is therefore a challenge to formulate a composition having improved longevity of the fragrance character, preferably components derived from the volatile fragrance materials, without having the fragrance character substantially altered over time by the presence of the base notes in the composition. One approach for addressing the challenge has been to formulate with higher proportions of perfume raw materials with a low volatility and which are therefore more substantive on the substrate. However, as discussed above, this restricts the type of fragrance profile that can be 50 achieved over time. [0009] Another approach, as disclosed in U.S. Patent 4,264,478 (Amerchol Corp.), has been to use a non-odorous material, such as an alkoxylated methyl glucoside, as a modulator to extend the longevity of the perfume raw materials, which are normally too volatile to last for very long. However, U.S. Patent ’478 simply teaches the addition of the modulator to an existing fragrance composition with a traditional construction of high levels of base note materials. As such, the 55 resultant overall effect on the fragrance profile of the composition would be to make the whole fragrance weaker because the impact of the modulator on the more volatile fragrance materials cannot be noticed due to the presence of excessive levels of the base notes in the composition. [0010] Similarly, Moshel, et al., Perfumer & Flavorist, Vol. 7, pp.41-47, 1982, teaches that alkoxylated methyl glucosides

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function as a "fixative" and bind to individual perfume raw materials for improving the longevity of a particular perfume raw material. Moshel, et al., shows that the fixative’s ability to improve the longevity for any particular perfume raw material will depend on its boiling point. However, Moshel, et al., does not disclose or suggest how to formulate with the fixative for a full fragrance composition, which incorporates multiple perfume raw materials, so that the fragrance strength 5 is maintained and the character of the middle notes is perceived as dominant after many hours. [0011] As such the prior art teachings still have limitations, and does not adequately teach how to provide a composition wherein the prolonged fragrance profile has sufficient strength to be noticeable and remains distinctive in character over time. Therefore, there remains a need for a composition that is perceived by the consumer over long, preferably very long, duration after application. There is also a need for a composition which exhibits enhanced intensity of the fragrance 10 profile over time, preferably so that the volatile fragrance materials remains significantly consistent from its initial impression to the end. It is desirable that the compositions are relevant to fragrances derived from volatile fragrance materials having a vapor pressure ≥ 0.133 Pa (0.001 Torr) at 25°C. [0012] US4324703 A discusses Colognes, toilet waters, after-bath splashes and other fragranced compositions with the addition of methyl glucoside polyols. 15 [0013] WO13064412 A2 and WO13060691 A2 discuss discusses a perfuming composition said to be capable of prolonging the release of a perfuming component into the surrounding environment when applied on a body surface. The composition comprises PPG-3 myristyl ether as a fragrance evaporation modulator in the presence of high amounts of ethanol. [0014] WO2011154926 discusses a perfuming composition capable of prolonging the release of a perfuming compo- 20 nent into the surrounding environment when applied on a body surface. The composition comprises isocetyl alcohol as a fragrance evaporation modulator in the presence of high amounts of ethanol.

SUMMARY OF THE INVENTION

25 [0015] In a first aspect, the present invention is directed to a composition in accordance with the claims. In another aspect, the present invention is directed to a method in accordance with the claims. [0016] In yet another aspect, the present invention is further directed to a method of modifying or enhancing the odour properties of a body surface with a composition of the present invention, by contacting or treating the body surface with the composition. 30 [0017] In other aspects there are provided a method for producing a consumer product, and a perfuming consumer product or article. [0018] These and other features of the present invention will become apparent to one skilled in the art upon review of the following detailed description when taken in conjunction with the appended claims.

35 BRIEF DESCRIPTION OF THE DRAWINGS

[0019] While the specification concludes with claims particularly pointing out and distinctly claiming the invention, it is believed that the invention will be better understood from the following description of the accompanying figures wherein:

40 Figure 1 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition A" of the present invention comprising 8.00 wt% of low volatile fragrance materials as compared to "Composition B", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of time elapsed since application of the composition. Figure 2 provides the panel test results of perceived fragrance profile, particularly fragrance character dominance, 45 of "Composition A" of the present invention comprising 8.00 wt% of low volatile fragrance materials as compared to "Composition B", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of time elapsed since application of the composition. Figure 3 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition C" of the present invention comprising 0.20 wt% of low volatile fragrance materials as compared to "Composition 50 D", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of time elapsed since application of the composition. Figure 4 provides the panel test results of perceived differences in the fragrance profile, particularly differences in the fragrance character, of "Composition C" of the present invention comprising 0.20 wt% of low volatile fragrance materials as compared to "Composition D", a control absent of a fragrance modulator (PPG-20 Methyl Glucose 55 Ether), and as a function of time elapsed since application of the composition. Figure 5 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition N" of the present invention comprising 54 wt% of low volatile fragrance materials as compared to "Composition O", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of time elapsed since

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application of the composition. Figure 6 provides the panel test results of perceived fragrance profile, particularly fragrance character dominance, of "Composition N" of the present invention comprising 54 wt% of low volatile fragrance materials as compared to "Composition O", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of 5 time elapsed since application of the composition. Figure 7 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition I" wherein the fragrance component comprises 40.14 wt% of low volatile fragrance materials as compared to "Com- position J", a control absent of a fragrance modulator (PPG-20 Methyl Glucose Ether), and as a function of time elapsed since application of the composition. 10 Figure 8 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition b" wherein the fragrance component comprises 1.0 wt% of low volatile fragrance material as compared to "Com- position a", a control composition absent of a fragrance modulator (Simulsol SL11W™), and as a function of time elapsed since application of the composition. Figure 9 provides the panel test results of perceived fragrance profile, particularly fragrance intensity, of "Composition 15 d" wherein the fragrance component comprises 1.0 wt% of low volatile fragrance material as compared to "Com- position c", a control composition absent of a fragrance modulator (Plantacare ® 810 UP), and as a function of time elapsed since application of the composition.

DETAILED DESCRIPTION OF THE INVENTION 20 Definitions

[0020] As used herein, articles such as "a" and "an" when used in a claim, are understood to mean one or more of what is claimed or described. 25 [0021] As used herein, the terms "include", "includes" and "including" are meant to be non-limiting. [0022] As used herein, the term "composition" includes a fine fragrance composition intended for application to a body surface, such as for example, skin or hair, i.e., to impart a pleasant odour thereto, or cover a malodour thereof. They are generally in the form of perfume concentrates, perfumes, eau de parfums, eau de toilettes, aftershaves, colognes, body splashes, or body sprays. The fine fragrance compositions may be ethanol based compositions. The term "com- 30 position" may also include a cosmetic composition, which comprises a fragrance material for the purposes of delivering a pleasant smell to drive consumer acceptance of the cosmetic composition. The term "composition" may also include cleaning compositions, such as fabric care composition or home care compositions, including air care compositions, for use on clothing or other substrates such as hard surfacese (.g., dishes, floors, countertops). Additional non-limiting examples of "composition" may also include facial or body powder, foundation, body/facial oil, mousse, creams e(.g., 35 cold creams), waxes, sunscreens and blocks, bath and shower gels, lip balms, self-tanning compositions , masks and patches. [0023] As used herein, the term "consumer" means both the user of the composition and the observer nearby or around the user. [0024] As used herein, the term "fragrance material" and "fragrance materials" relates to a perfume raw material, or 40 a mixture of perfume raw materials, that are used to impart an overall pleasant odour or fragrance profile to a composition. "Fragrance materials" can encompass any suitable perfume raw materials for fragrance uses, including materials such as, for example, alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulfurous heterocyclic compounds and essential oils. However, naturally occurring plant and animal oils and exudates comprising complex mixtures of various chemical components are also know for use as "fragrance materials". The 45 individual perfume raw materials which comprise a known natural oil can be found by reference to Journals commonly used by those skilled in the art such as "Perfume and Flavourist" or "Journal of Essential Oil Research", or listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA andmore recently re-publisehdby Allured Publishing Corporation Illinois(1994). Additionally, some perfume raw materials are supplied by the fragrance houses (Firmenich, International Flavors & Fragrances, Givaudan, Symrise) as mixtures 50 in the form of proprietary speciality accords. Non-limiting examples of the fragrance materials useful herein include pro- fragrances such as acetal pro-fragrances, ketal pro-fragrances, ester pro-fragrances, hydrolyzable inorganic-organic pro-fragrances, and mixtures thereof. The fragrance materials may be released from the pro-fragrances in a number of ways. For example, the fragrance may be released as a result of simple hydrolysis, or by a shift in an equilibrium reaction, or by a pH-change, or by enzymatic release. 55 [0025] As used herein, the term "fragrance profile" means the description of how the fragrance perceived by the human nose evolves over time from when it is first applied. It is a result of the combination of the top, middle and base notes, if present, of a fragrance. A fragrance profile is composed of 2 characteristics: ’intensity’ and ’character’. The ’intensity’ relates to the perceived strength whilst ’character’ refers to the odour impression or quality of the perfume,i.e., fruity,

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floral, woody, etc. [0026] As used herein, the terms "perfume" and "fragrance" are used interchangeably to designate the component in the composition that is formed of fragrance materials, i.e., ingredients capable of imparting or modifying the odour of skin or hair or other substrate. 5 [0027] As used herein, the terms "modulator" and "fixative" are used interchangeably to designate an agent having the capacity to affect the fragrance profile by impacting the fragrance materials’ evaporation rate. By incorporating the modulator, it is desired that the fragrance profile, preferably the volatile fragrance materials components, of the composition can be perceived by an observer or user thereof, over a longer period of time, as compared to the same perception in the absence of the modulator. In particular, according to the invention, alkoxylated glucoside, preferably PPG-20 10 Methyl Glucose Ether (Glucam™ P-20 available from Lubrizol (USA)), is a modulator of the perceived tenacity of the compositions of the present invention, i.e., it is used to prolong the perceived intensity of the fragrance profile over time, ascompared tothe perception when PPG-20 MethylGlucose Ether isnot used inthe composition. However,as discovered bythe inventors, simplyadding modulators to atraditionally constructed fragrance compositionwill not ensure an improved or enhanced fragrance profile over time. Instead, it is only when the modulators are added in the presence of reduce 15 levels of low volatile fragrance materials can the intensity of the fragrance profile, preferably the volatile fragrance materials, be perceived for longer periods as compared to control composition absent the modulators and low levels of low volatile fragrance materials. [0028] As used herein, the term "co-modulator" means an agent that is added to the composition in addition to the modulators and has the similar function of impacting the evaporation rate and intensity of the fragrance materials, so as 20 to improve or prolong the perception of the fragrance profile by the consumer. Preferred example of a co-modulator is isocetyl alcohol (CERAPHYL® ICA; see PCT Publication No. WO2013/64412 (Firmenich)). [0029] As used herein, the term "non-odorous" means an agent that does not impart an odour of its own when added into a composition of the present invention. For example, a "non-odorous modulator" such as PPG-20 Methyl Glucose Ether does not impart a new odour that alters the character of the composition to which it is added. 25 [0030] As used herein, the term "vapor pressure" means the partial pressure in air at a defined temperature for a given chemical species. It defines a chemical species’ desire to be in the gas phase rather than the liquid or solid state. The higher the vapour pressure the greater the proportion of the material that will, at equilibrium, be found in a closed headspace. It is also related to the rate of evaporation of a fragrance material which is defined in an open environment where material is leaving the system. The vapor pressure is determined according to the reference program Advanced 30 Chemistry Development (ACD/Labs) Software Version 11.02, (© 1994-2013). [0031] It is understood that the test methods that are disclosed in the Test Methods Section of the present application must be used to determine the respective values of the parameters of Applicants’ inventions as described and claimed herein. [0032] In all embodiments of the present invention, all percentages are by weight of the total composition, as evident 35 by the context, unless specifically stated otherwise. All ratios are weight ratios, unless specifically stated otherwise, and all measurements are made at 25°C, unless otherwise designated.

Compositions

40 [0033] Specifically, in one aspect, the present invention provides for a composition comprising a fragrance component present in an amount of from 1 wt% to 30 wt%, preferably less than 25 wt%, preferably less than 20 wt%, preferably less than 15 wt%, preferably less than 10 wt% or preferably less than 8 wt%, relative to the total weight of the composition. Alternatively, the fragrance component is present in an amout of from about 0.04 wt%, 0.3 wt%, 1 wt%, 8 wt% or 10 wt%, to about 15 wt%, 20 wt%, 25 wt% or 30 wt%, relative to the total weight of the composition. 45 [0034] Further, the fragrance component comprises at least one low volatile fragrance material having a vapor pressure < 0.001 Torr at 25°C. In certain embodiments, the compositions of the present invention comprises at least 5 low volatile fragrance materials. It is preferred that the composition of the present invention comprises low, preferably very low, or even neglible, levels of the low volatile fragrance materials than would traditionally be present in a composition. As such, compositions of the present invention can comprise low levels of the volatile fragrance material present in an amount 50 of from about 0.01 wt% to about 30 wt%, preferably less than about 25%, preferably less than about 20 wt%, preferably less than about 12 wt%, preferably less than about 10 wt%, preferably less than about 8 wt%, preferably less than about 5 wt%, preferably less than about 2 wt%, or preferably less than about 1 wt%, or combinations thereof, relative to the total weight of the fragrance component. Alternatively, the low volatile fragrance material is present in an amount of from about 0.01 wt%, 1 wt%, 2 wt%, 5 wt%, 8 wt%, 10 wt%, 12 wt%, 15 wt%, 20 wt%, 25 wt% or 30 wt%, relative to the total 55 weight of the fragrance component. If there is more than one low volatile fragrance materials, then the ranges provided hereinabove cover the total of all of the low volatile fragrance materials. [0035] The composition further comprises at least one non-odorous fragrance modulator formed from an alkoxylated glucoside, preferably selected from the group consisting of methyl glucoside polyol, ethyl glucoside polyol, and propyl

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glucoside polyol, wherein the alkoxylated glucoside is preferably PPG-20 Methyl Glucose Ether (GLUCAM™ P-20 avilable from Lubrizol, USA). The alkoxylated glucoside is present in an amount of from about 0.1 wt% to about 20 wt%, preferably from about 0.5 wt% to about 18 wt% or more preferably from about 2.5 wt% to about 15 wt% or combinations thereof, relative to the total weight of the composition. Alternatively, the alkoxylated glucoside is present in an amount 5 of from about 0.1 wt%, 0.5 wt% or 2.5 wt% to about 15 wt%, 18 wt% or 20 wt%, relative to the total weight of the composition. If there is more than one non-odorous fragrance modulators, then the ranges provided hereinabove cover the total of all of the non-odorous fragrance modulators. [0036] In an embodiment, the non-odorous modulator of the present invention is preferably a liquid at temperatures lower than 100°C, preferably at ambient temperature. Particularly preferred non-odorous modulators are fully miscible 10 with the PRMs to form a single phase liquid. However, if the PRMs are not entirely miscible, or are immiscible, then co- solvents (e.g., dipropylene glycol (DPG), triethyl citrate, or others as well known to those skilled in the art) can be added to aid in the solubility of the PRMs. [0037] The inventors have surprisingly discovered that by reducing the levels of the low volatile fragrance materials (i.e., base notes) in a composition, the effect of the non-odorous modulator on the fragrance profile, particularly the 15 portion of the fragrance profile which is derived from volatile fragrance materials i.e( ., top and middle notes), can be improved. By "improved" it is meant that the fragrance character of the composition, particular the components contributed by the volatile fragrance materials, can be perceived by the consumer at later time points such as, for example, 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, and possibly all the way up to 24 hrs after application as compared to controls, i.e., compositions containing normal or large levels of the low volatile fragrance materials and the non-odorous modulator 20 or compositions containing reduced levels of low volatility fragrance materials and no non-odorous modulator. [0038] Alternatively, by "improved" it can mean that the perception of the components contributed by the volatile fragrance materials, by the consumer, is markedly increased or enhanced as compared to the controls. "Increased" or "enhanced" perception of the fragrance profile means that the consumer perceives the fragrance profile of a composition as not changing from its initial impression or the changes are minimal from when the composition was first applied to 25 when it dissipates. [0039] Typically, it has been very difficult to formulate fragrance profile with an accord, particularly a floral accord characteristic of the middle notes, which can last for very long periods, especially throughout the life of the composition after its application, without giving way to the stronger odours of the base notes. The present invention of reducing levels of the low volatile fragrance materials ( i.e., base notes) with the modulators will allow perfumers to increase the perception 30 of the volatile perfume materials, particularly the middle notes, to create new characters and address a re-occurring consumer issue that particular fragrance profiles, particularly the floral aromas, do not last long enough. [0040] Such a solution as presented herein provides enhanced longevity of the fragrance profile, particularly amongst those composition formulated from volatile fragrance materials having medium to high vapor pressure ranges ( ≥ 0.133 Pa (0.001 Torr) at 25°C), without having to rely on the 35 presence or significant amounts of the low volatile fragrance materials, which has a tendency to overpower and alter the overall character of a fragrance. This provides the perfumer options to formulate accords having new fragrance profiles. [0041] In another aspect, the present invention also provides a composition, wherein the fragrance component further comprising one or more volatile fragrance materials having a vapor pressure ≥ 0.133 Pa (0.001 Torr) at 25°C. The volatile 40 fragrance material is present in an amount of from about 70 wt% to about 99.9 wt%, preferably greater than about 80 wt%, or most preferably greater than 88 wt%, or combinations thereof, relative to the total weight of the fragrance component. Alternatievly, the volatile fragrance material is present in an amount of from about 70 wt%, 75 wt%, 80 wt%, 85 wt%, 88 wt%, 90 wt%, 92 wt%, 95 wt%, 98 wt% or 99.9 wt%, relative to the total weight of the fragrance component. In certain embodiments, the compositions of the 45 present invention comprise at least 5, at least 10, at least 15 or at least 20, volatile fragrance materials. If there is more than one volatile fragrance materials, then the ranges provided hereinabove cover the total weight of all of the volatile fragrance materials. [0042] In one embodiment, the volatile fragrance materials can be divided into: (i) a high volatile fragrance material having a vapor pressure > 13.3 Pa (0.1 Torr) at 25°C, and (ii) a medium volatile 50 fragrance material having a vapor pressure in the range of from 0.133 Pa (0.001 Torr) at 25°C to 13.3 Pa (0.1 Torr) at 25°C. While the further classification of the volatile fragrance materials into high and medium volatile fragrance materials is provided to help illustrate the fragrance characters of the perfume raw materials and is useful for when it comes to formulating new fragrance profiles, it should not be construed as limiting on what qualifies as a volatile fragrance material. [0043] In yet another aspect, the low volatile fragrance material is preferably selected from ingredients listed in Table 55 1 hereinafter. [0044] In yet another aspect, the present invention also provides a composition further comprising one or more non- odorous fragrance co-modulators selected from the group consisting of:

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(i) Isocetyl alcohol (CERAPHYL® ICA); (ii) PPG-3 myristyl ether (preferably Tegosoft™ APM and/or Varonic® APM); (iii) Neopentyl glycol diethylhexanoate (preferably Schercemol™ NGDO); and (iv) mixture thereof preferably with isocetyl alcohol (CERAPHYL ® ICA); 5 wherein the fragrance co-modulators are present in an amount of from about 0.05 wt% to about 10 wt%, preferably from about 0.5 wt% to about 6 wt%, or combinations thereof, relative to the total weight of the composition. Alternatively, the fragrance co-modulators is present in an amount of from about 0.05 wt% or 0.5 wt% to about 6 wt% or 10 wt%, relative to the total weight of the composition. If there is more than one non-odorous fragrance co-modulator, then the ranges 10 provided hereinabove cover all of the non-odorous fragrance co-modulators. [0045] In one embodiment, the non-odorous fragrance modulators are formed of at least 50 wt% of a non-odorous fragrance modulator, relative to the total weight of the non-odorous modulators and the non-odorous co-modulators present in the composition. [0046] In yet another aspect, the present invention provides a composition comprising: 15 (i) from about 50 wt% to about 80 wt% of ethanol; (ii) from about 0.1 wt% to about 20 wt% of at least one non-odorous fragrance modulator formed of an alkoxylated glucoside selected from the group consisting of methyl glucoside polyol, ethyl glucoside polyol, and propyl glucoside polyol, preferably PPG-20 Methyl Glucose Ether; and 20 (iii) a fragrance component; and wherein wt% of the non-odorous fragrance modulator is greater than the fragrance component.

Entrapment Materials

25 [0047] In yet another aspect, compositions of the present invention may comprise an entrapment material at a level such that the weight ratio of the entrapment material to the fragrance materials is in the range of from about 1:20 to about 20:1. Preferably, the composition may comprise an entrapment material present in the amount of from about 0.001 wt% to about 40 wt%, from about 0.1 wt% to about 25 wt%, from about 0.3 wt% to about 20 wt%, from about 0.5 wt% to about 10 wt%, or from about 0.75 wt% to about 5 wt%, relative to the total weight of the composition. The compositions 30 disclosed herein may comprise from 0.001 wt% to 40%, from 0.1 wt% to 25 wt%, from 0.3 wt% to 20 wt%, from 0.5 wt% to 10 wt% or from 0.75 wt% to 5 wt%, relative to the total weight of the composition, of a cyclic oligosaccharide. [0048] Suitable entrapment materials for use herein are selected from polymers; capsules, microcapsules and nano- capsules; liposomes, absorbents; cyclic oligosaccharides and mixtures thereof. Preferred are absorbents and cyclic oligosaccharides and mixtures thereof. Highly preferred are cyclic oligosaccharidessee ( PCT Publication Nos. 35 WO2000/67721 (Procter & Gamble); and WO2000/67720 (Procter & Gamble); and U.S. Patent No. US 6,893,647 (Procter & Gamble)). [0049] As used herein, the term "cyclic oligosaccharide" means a cyclic structure comprising six or more saccharide units. Preferred for use herein are cyclic oligosaccharides having six, seven or eight saccharide units and mixtures thereof, more preferably six or seven saccharide units and even more preferably seven saccharide units. It is common 40 in the art to abbreviate six, seven and eight membered cyclic oligosaccharides to α, β and γ respectively. [0050] The cyclic oligosaccharide of the compositions used for the present invention may comprise any suitable saccharide or mixtures of saccharides. Examples of suitable saccharides include, but are not limited to, glucose, fructose, mannose, galactose, maltose and mixtures thereof. However, preferred for use herein are cyclic oligosaccharides of glucose. The preferred cyclic oligosaccharides for use herein are α-cyclodextrins or β-cyclodextrins, or mixtures thereof, 45 and the most preferred cyclic oligosaccharides for use herein are β-cyclodextrins. [0051] The cyclic oligosaccharide, or mixture of cyclic oligosaccharides, for use herein may be substituted by any suitable substituent or mixture of substituents. Herein the use of the term "mixture of substituents" means that two or more different suitable substituents can be substituted onto one cyclic oligosaccharide. The derivatives of cyclodextrins consist mainly of molecules wherein some of the OH groups have been substituted. Suitable substituents include, but 50 are not limited to, alkyl groups; hydroxyalkyl groups; dihydroxyalkyl groups; (hydroxyalkyl)alkylenyl bridging groups such as cyclodextrin glycerol ethers; aryl groups; maltosyl groups; allyl groups; benzyl groups; alkanoyl groups; cationic cyclodextrins such as those containing 2-hydroxy-3-(dimethylamino) propyl ether; quaternary ammonium groups; anionic cyclodextrins such as carboxyalkyl groups, sulphobutylether groups, sulphate groups, and succinylates; amphoteric cyclodextrins; and mixtures thereof. 55 [0052] The substituents may be saturated or unsaturated, straight or branched chain. Preferred substituents include saturated and straight chain alkyl groups, hydroxyalkyl groups and mixtures thereof. Preferred alkyl and hydroxyalkyl substituents are selected from C 1-C8 alkyl or hydroxyalkyl groups or mixtures thereof, more preferred alkyl and hydroxyalkyl substituents are selected from C1-C6 alkyl or hydroxyalkyl groups or mixtures thereof, even more preferred alkyl

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and hydroxyalkyl substituents are selected from C1-C4 alkyl or hydroxyalkyl groups and mixtures thereof. Especially preferred alkyl and hydroxyalkyl substituents are propyl, ethyl and methyl, more especially hydroxypropyl and methyl and even more preferably methyl. [0053] Preferred cyclic oligosaccharides for use in the present invention are unsubstituted, or are substituted by only 5 saturated straight chain alkyl, or hydroxyalkyl substituents. Therefore, preferred examples of cyclic oligosaccharides for use herein are α-cyclodextrin, β-cyclodextrin, methyl-α-cyclodextrin, methyl-β-cyclodextrin, hydroxypropyl-α-cyclodextrin and hydroxypropyl-β-cyclodextrin. Most preferred examples of cyclic oligosaccharides for use herein are methyl- α- cyclodextrin and methyl-β-cyclodextrin. These are available from Wacker-Chemie GmbH Hanns-Seidel-Platz 4, Munchen, DE under the tradename Alpha W6 M and Beta W7 M respectively. Especially preferred is methyl-β-cyclo- 10 dextrin. [0054] The cyclic oligosaccharides of the compositions used for the present invention are preferably soluble in water, ethanol, or both water and ethanol. As used herein "soluble" means at least about 0.1 g of solute dissolves in 100 mL of solvent, at 25°C and 1 atm of pressure. Preferably the cyclic oligosaccharides for use herein have a solubility of at least about 1 g/100 mL, at 25°C and 1 atm of pressure. Preferred is that cyclic oligosaccharides are only present at 15 levels up to their solubility limits in a given composition at room temperature. A person skilled in the art will recognise that the levels of cyclic oligosaccharides used in the present invention will also be dependent on the components of the composition and their levels, for example the solvents used or the exact fragrance oils, or combination of fragrance oils, present in the composition. Therefore, although the limits stated for the entrapment material are preferred, they are not exhaustive. 20 Volatile Solvents

[0055] In yet another aspect, the present invention provides the solution to the problem of extending the longevity of the fragrance profile of compositions, particularly fine fragrance and cosmetic compositions, preferably fine fragrance 25 compositions, which commonly contain high levels of ethanol or other alcohols ( e.g., methanol, propanol, isopropanol, butanol, and mixtures thereof) commonly found in commercial fine fragrance products. Accordingly, ethanol may be present in any of the compositions of the present invention, and more specifically, it will form from about 10 wt% to about 80 wt%, or even from about 25 wt% to about 75 wt% of the composition, or combinations thereof, relative to the total weight of the composition. Alternatively, ethanol may be present in an amount of from about 10 wt% or 25 wt% to about 30 75 wt% or 80 wt%, relative to the total weight of the composition. Any acceptable quality of ethanol, compatible and safe for the specific intended use of the composition such as, for example, topical applications of fine fragrance or cosmetic compositions, and is convenient for use in the compositions according to the present invention.

Non-Volatile Solvents 35 [0056] The composition may comprise a non-volatile solvent or a mixture of non-volatile solvents. Non-limiting examples of non-volatile solvents include benzyl benzoate, diethyl phthalate, isopropyl myristate, propylene glycol, dipropylene glycol, triethyl citrate, and mixtures thereof. These solvents often are introduced to the product via the perfume oil as many perfume raw materials may be purchased as a dilution in one of these solvents. Where non-volatile solvents are 40 present, introduced either with the perfume materials or separately, then for the purposes of calculating the proportion of fragrance component having a vapour pressure of < 0.001 Torr at 25°C the total fragrance components does not include non-volatile solvents. In addition if present with cyclic oligosacchrides, the non-volatile solvent may be included at a weight ratio of the non-volatile solvent to the cyclic oligosaccharide of less than 1:1, less than 1:2, less than 1:10, or less than 1:100. 45 Water

[0057] In yet another aspect, water may be present in any of the compositions of the present invention, and more specifically, it shall not exceed about 40 wt%, preferably about 20 wt% or less, or more preferably about 10 wt% or less, 50 relative to the total weight of the composition. Alternatively, water may be present in an amount of from about 10 wt% or 20 wt% to about 40 wt%, relative to the total weight of the composition. When the composition is a cosmetic composition the level of water should not be so high that the product becomes cloudy thus negatively impacting the product aesthetics. It is understood that the amount of water present in the composition may be from the water present in the ethanol used in the composition, as the case may be. 55 Propellants

[0058] The compositions describedherein may include apropellant. Some examples of propellants include compressed

8 EP 2 961 374 B1

air, nitrogen, inert gases, carbon dioxide, and mixtures thereof. Propellants may also include gaseous hydrocarbons like propane, n-butane, isobutene, cyclopropane, and mixtures thereof. Halogenated hydrocarbons like 1,1-difluoroethane may also be used as propellants. Some non-limiting examples of propellants include 1,1,1,2,2-pentafluoroethane, 1,1,1,2- tetrafluoroethane, 1,1,1,2,3,3,3-heptafluoropropane, trans-1,3,3,3-tetrafluoroprop-1-ene, dimethyl ether, dichlorodifluor- 5 omethane (propellant 12), 1,1-dichloro-1,1,2,2-tetrafluoroethane (propellant 114), 1-chloro-1,1-difluoro-2,2-trifluor- oethane (propellant 115), 1-chloro-1,1-difluoroethylene (propellant 142B), 1,1-difluoroethane (propellant 152A), mono- chlorodifluoromethane, and mixtures thereof. Some other propellants suitable for use include, but are not limited to, A- 46 (a mixture of isobutane, butane and propane), A-31 (isobutane), A-17 (n-butane), A-108 (propane), AP70 (a mixture of propane, isobutane and n-butane), AP40 (a mixture of propane, isobutene and n-butane), AP30 (a mixture of propane, 10 isobutane and n-butane), and 152A (1,1 diflouroethane). The propellant may have a concentration from about 15%, 25%, 30%, 32%, 34%, 35%, 36%, 38%, 40%, or 42% to about 70%, 65%, 60%, 54%, 52%, 50%, 48%, 46%, 44%, or 42% by weight of the total fill of materials stored within the container.

Antiperspirant Active 15 [0059] The compositions described herein may be free of, substantially free of, or may include an antiperspirant active (i.e., any substance, mixture, or other material having antiperspirant activity). Examples of antiperspirant actives include astringent metallic salts, like the inorganic and organic salts of aluminum, zirconium and zinc, as well as mixtures thereof. Such antiperspirant actives include, for example, the aluminum and zirconium salts, such as aluminum halides, aluminum 20 hydroxyhalides, zirconyl oxyhalides, zirconyl hydroxyhalides, and mixtures thereof.

Other Ingredients

[0060] In yet another aspect, the composition consists essentially of the recited ingredients but may contain small 25 amounts (not more than about 10 wt%, preferably no more than 5 wt%, or preferably no more than 2 wt% thereof, relative to the total weight of the composition) of other ingredients that do not impact on the fragrance profile, particularly the evaporation rate and release of the fragrance materials. For example, a fine fragrance composition may comprise stabilizing or anti-oxidant agents, UV filters or quenchers, or colouring agents, commonly used in perfumery. There are a number of other examples of additional ingredients that are suitable for inclusion in the present compositions, particularly 30 in compositions for cosmetic use. These include, but are not limited to, alcohol denaturants such as denatonium benzoate; UV stabilisers such as benzophenone-2; antioxidants such as tocopheryl acetate; preservatives such as phenoxyethanol, benzyl alcohol, methyl paraben, and propyl paraben; dyes; pH adjusting agents such as lactic acid, citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, and sodium carbonate; deodorants and anti-microbials such as farnesol and zinc phenolsulphonate; humectants such as glycerine; oils; skin conditioning agents such as allantoin; 35 cooling agents such as trimethyl isopropyl butanamide and menthol; hair conditioning ingredients such as panthenol, panthetine, pantotheine, panthenyl ethyl ether, and combinations thereof; silicones; solvents such as hexylene glycol; hair-hold polymers such as those described in PCT Publication WO94/08557 (Procter & Gamble); salts in general, such as potassium acetate and sodium chloride and mixtures thereof. [0061] In yet another aspect, the composition of the present invention, depending on its intended use, is a mixture of 40 fragrance materials possibly together with other ingredients such as, for example, perfume carriers. By the term "perfume carrier", it is meant to include materials which are practically neutral from a perfumery point of view, i.e., which does not significantly alter the organoleptic properties of perfuming components. The perfume carrier may be a compatible liquid or solid fillers, diluents, extenders and the like. The term "compatible", as used herein, means that the components of the compositions of this invention are capable of being combined with the primary actives of the present invention, and 45 with each other, in a manner such that there is no interaction which would substantially reduce the efficacy of the composition under ordinary use situations. The type of carrier utilized in the present invention depends on the type of product desired and may comprise, but are not limited to, solutions, aerosols, emulsions (including oil-in-water or water- in-oil), gels, and liposomes. Preferably, the carrier is a liquid and will be a solvent such as, for example, dipropyleneglycol , diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol, or ethyl citrate (triethyl citrate). 50 [0062] In yet another aspect, the compositions for use in the present invention may take any form suitable for use, more preferably for perfumery or cosmetic use. These include, but are not limited to, vapour sprays, aerosols, emulsions, lotions, liquids, creams, gels, sticks, ointments, pastes, mousses, powders, granular products, substrates, cosmetics (e.g. semi-solid or liquid makeup, including foundations) and the like. Preferably the compositions for use in the present invention take the form of a vapour spray. Compositions of the present invention can be further added as an ingredient 55 to other compositions, preferably fine fragrance or cosmetic compositions, in which they are compatible. As such they can be used within solid composition or applied substrates etc. [0063] It has been ascertained that, amongst such compositions of the present invention, the preferred compositions are those comprising of:

9 EP 2 961 374 B1

(i) a fragrance component present in the amount of from about 1.0 wt% to about 30 wt% relative to the total weight of the composition, and wherein the fragrance component comprises:

(a) at least one low volatile fragrance material having a vapor pressure < 0.133 Pa (0.001 Torr) at 25°C, present 5 in the amount of from about 0.1 wt% to about 30 wt%, preferably less than about 28 wt%, preferably less than about 25 wt%, preferably less than about 22 wt%, preferably less than 20 wt%, preferably less than 18 wt%, or preferably less than 15 wt%, relative to the total weight of the fragrance component; and (b) at least one volatile fragrance material having a vapor pressure ≥ 0.133 Pa (0.001 Torr) at 25°C, present in the amount of from about 70 wt% to about 99.9 wt%, relative to the total weight of the fragrance component; and 10 (ii) at least one non-odorous fragrance modulator formed of an alkoxylated glucoside, preferably PPG-20 Methyl Glucose Ether, in the amount of from about 2.5 wt% to about 20 wt%, relative to the total weight of the composition.

[0064] In an embodiment, the composition further comprises one or more non-odorous fragrance co-modulators se- 15 lected from the group consisting of isocetyl alcohol (CERAPHYL® ICA), PPG-3 myristyl ether (preferably Tegosoft™ APM and/or Varonic® APM), neopentyl glycol diethylhexanoate (preferably Schercemol™ NGDO), and mixture thereof preferably with isocetyl alcohol (CERAPHYL® ICA), present in the amount of from about 0.5 wt% to about 10 wt%, relative to the total weight of the composition. [0065] Therefore, it goes without saying that the compositions of the present invention encompasses any composition 20 comprising any of the ingredients cited herein, in any embodiment wherein each such ingredient is independently present in any appropriate amount as defined herein. Many such compositions, than what is specifically set out herein, can be encompassed.

Article of Manufacture 25 [0066] The composition may be included in an article of manufacture comprising a spray dispenser. The spray dispenser may comprise a vessel for containing the composition to be dispensed. The spray dispenser may comprise an aerosolized composition (i.e. a composition comprising a propellant) within the vessel as well. Other non-limiting examples of spray dispensers include non-aerosol dispensers ( e.g. vapor sprays), manually activated dispensers, pump-spray dispensers, 30 or any other suitable spray dispenser available in the art.

Methods of Using the Compositions

[0067] The composition of the present invention according to any embodiments described herein is a useful perfuming 35 composition, which can be advantangeously used as consumer products intended to perfume any suitable substrate. As used herein, the term "substrate" means any surface to which the composition of the present invention may be applied to without causing any undue adverse effect. For example, this can include a wide range of surfaces including human or animal skin or hair, paper (fragranced paper), air in a room (air freshner or aromatherapy composition), fabric, furnishings, dishes, hard surfaces and related materials. Preferred substrates include body surfaces such as, for example, 40 hair and skin, most preferably skin. [0068] The composition of the present invention may be used in a conventional manner for fragrancing a substrate. An effective amount of the composition, typically from about 1 mL to about 10,000 mL, preferably from about 10 mL to about 1,000 mL, more preferably from about 25 mL to about 500 mL, or most preferably from about 50 mL to about 100 mL, or combinations thereof, is applied to the suitable substrate. Alternatively, an effective amount of the composition 45 of the present invention is from about 1 mL, 10 mL, 25 mL or 50 mL to about 100 mL, 500 mL, 1,000 mL or 10,000 mL. The composition may be applied by hand or applied utilizing a delivery apparatus such as, for example, vaporizer or atomizer. Preferably, the composition is allowed to dry after its application to the substrate. The scope of the present invention should be considered to cover one or more distinct applications of the composition or the continuous release of a composition via a vaporizer or other type of atomizer. 50 [0069] In one embodiment, present invention preferably relates to fine fragrance compositions in the form of a perfume, an eau de toilette, an eau de parfum, a cologne, a body splash, or a body spray. Therefore, according to this embodiment, the present invention provides a method of modifying or enhancing the odour properties of a body surface, preferably hair or skin, comprising contacting or treating the body surface with a composition of the present invention. [0070] In another embodiment, the present invention relates to compositions of the present invention that may be used 55 as consumer products or articles selected from the group consisting of a fabric care product, an air care product, or a home care product. Therefore, according to this embodiment, the present invention provides a method of modifying or enhancing the odour properties of a substrate, preferably fabric, furnishings, dishes, hard surfaces and related materials, comprising contacting or treating the substrate with a composition of the present invention.

10 EP 2 961 374 B1

[0071] In another aspect, the present invention is directed to a method of enhancing the fragrance profile of a composition, preferably by improving the longevity of an aroma of the composition. The method comprises bringing into contact or mixing at least one non-odorous fragrance modulator with at least one low volatile fragrance material according to the composition of the present invention. Preferably, the aroma is derived from the volatile fragrance materials in the 5 composition and is characterized by a floral aroma. Non-limiting examples of floral aroma include lavender-type note, a rose-type note, a lily of the valley-type note, a muguet-type note, a jasmine-type note, a magnolia-type note, a cyclamen- type note, a hyacinth-type note, a lilac-type note, an orange blossom-type note, a cherry blossom-type note, a peony- type note, a lotus-type note, a linden blossom-type note, an osmanthus-type note, a lilac-type note, a heliotrope-type note, a violet-type note, an orris-type note, a tiare-type note and the like. 10 [0072] In one embodiment, the fragrance profile or aroma of the composition is detectable by a consumer at later time points such as, for example, 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, and possibly all the way up to 24 hours after application of the composition to a substrate as compared to controls.

Fragrance Materials 15 [0073] In order that the compositions can be developed with the appropriate fragrance profile for the present invention, the "fragrance materials" have been classified by their vapour pressure, as determined according to the reference program Advanced Chemistry Development (ACD/Labs) Software Version 11.02, (1994-2013). For the purpose of clarity, when the fragrance materials refer to a single individual compound, its vapor pressure should be determined according 20 to the reference program cited above. In the case that the fragrance materials are a natural oil, extract or absolute, which comprises a mixture of several compounds, the vapor pressure of the complete oil should be treated a a mixture of the individual perfume raw material components using the reference program cited above. The individual components and their level, in any given natural oil or extract, can be determined by direct injection of the oil into a GC-MS column for analysis as known by one skilled in the art. In the scenario that the fragrance materials are a proprietary speciality accord, 25 so called ’bases’, the vapor pressure, using the reference program cited above, should preferably be obtained from the supplier. However, it is understood by one skilled in the art that they can physically analyze the composition of a full fragrance oil available commercially to identity the fragrance raw materials and their levels using standard GC-MS techniques. This would be irrespective of wether they had been added to the fragrance oil as individual chemicals, as components of naturals or from proprietary bases. Although proprietary bases and and naturals are included in our 30 examples, when analyzing a commercially available fragrance via GC-MS one could simply identify the components of the base or natural oil as part of the overall fragrance mixture and their levels, without being able to identify which proprietary base or natural oil the fragrance had come from. [0074] The nature and type of fragrance materials in the compositions according to the present invention can be selected by the skilled person, on the basis of its general knowledge together with the teachings contained herein, with 35 reference to the intended use or application of the composition and the desired fragrance profile effect. Examples of suitable fragrance materials are disclosed in U.S. Pat. No. 4,145,184, U.S. Pat. No. 4,209,417, U.S. Pat. No. 4,515,705, and U.S. Pat. No. 4,152,272, provided that the composition comprises low volatile fragrance materials at levels in an amount of from about 0.1 wt% to about 30 wt%, preferably less than about 28 wt%, preferably less than about 25 wt%, preferably less than about 22 wt%, preferably less than 20 wt%, preferably less than 18 wt%, or preferably less than 15 40 wt%, or combinations thereof, relative to the total weight of the fragrance component. [0075] Examples of fragrance materials having a vapor pressure < 0.133 Pa (0.001 Torr) at 25°C (according to the reference program Advanced Chemistry Development (ACD/Labs) Software Version 11.02, (© 1994-2013)) to form the at most about 30 wt% of the low volatile fragrance materials are listed in Table 1 hereinafter.

45 Table 1 - Low Volatile Fragrance Materials for Use in the Compositions Vapor Pressure CAS Number Chemical name Common Name** (Torr at 25°C)* Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1- 1211-29-6 Methyl jasmonate 0.00096500 50 yl-, methyl ester, (1R,2R)- 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3- 28219-60-5 Hindinol 0.00096100 cyclopenten-1-yl)- Methyl beta-naphthyl 93-08-3 Ethanone, 1-(2-naphthalenyl)- 0.00095700 55 ketone 67633-95-8 3-Decanone, 1-hydroxy- Methyl Lavender Ketone 0.00095100

11 EP 2 961 374 B1

(continued)

Vapor Pressure CAS Number Chemical name Common Name** (Torr at 25°C)* 5 Cyclopropanemethanol, 1-methyl-2-[(1,2,2- 198404-98-7 Javanol® 0.00090200 trimethylbicyclo[3.1.0]hex-3-yl) methyl]- 121-32-4 Benzaldehyde, 3-ethoxy-4-hydroxy- Ethyl vanillin 0.00088400 28940-11-6 2H-1,5-Benzodioxepin-3(4H)-one, 7-methyl- Oxalone® 0.00083100 10 139504-68-0 2-Butanol, 1-[[2-(1,1-dimethylethyl)cyclohexyl]oxy]- Amber core 0.00080300 Spiro[5.5]undec-8-en-1- 502847-01-0 Spiro[5.5]undec-8-en-1-one, 2,2, 7,9-tetramethyl- 0.00073100 one, 2,2,7,9-tetramethyl- Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl 15 2570-03-8 trans-Hedione 0.00071000 ester, (1R,2R)-rel- Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl Methyl 24851-98-7 0.00071000 ester dihydrojasmonate 101-86-0 Octanal, 2-(phenylmethylene)- Hexylcinnamic aldehyde 0.00069700 20 Cyclopentanecarboxylic acid, 2-hexyl-3-oxo-, 37172-53-5 Dihydro Iso Jasmonate 0.00067500 methyl ester 65113-99-7 3-Cyclopentene-1-butanol, α,β,2, 2,3-pentamethyl- Sandalore® 0.00062500 Cyclopentanone, 2-(3,7-dimethyl-2,6-octadien-1- 25 68133-79-9 Apritone 0.00062000 yl)- 7212-44-4 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl- Nerolidol 0.00061600 53243-59-7 2-Pentenenitrile, 3-methyl-5-phenyl-, (2Z)- Citronitril 0.00061500 30 134123-93-6 Benzenepropanenitrile, 4-ethyl-α, α-dimethyl- Fleuranil 0.00057600 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8- 77-53-2 Cedrol Crude 0.00056900 tetramethyl-, (3R,3aS,6R,7R,8aS)- Ethanone, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8- 54464-57-2 Iso-E Super® 0.00053800 35 tetramethyl-2-naphthalenyl)- Propanoic acid, 2-methyl-, 4-formyl-2- 20665-85-4 Vanillin isobutyrate 0.00051200 methoxyphenyl ester 1,6-Heptadien-3-one, 1-(2,6,6-trimethyl-2- 79-78-7 Hexalon 0.00049800 40 cyclohexen-1-yl)- 6259-76-3 Benzoic acid, 2-hydroxy-, hexyl ester Hexyl Salicylate 0.00049100 93-99-2 Benzoic acid, phenyl ester Phenyl Benzoate 0.00047900 Cyclohexanepropanol, 2,2,6-trimethyl-α-propyl-, 153859-23-5 Norlimbanol 0.00046900 45 (1R,6S)- 70788-30-6 Cyclohexanepropanol, 2,2,6-trimethyl-α-propyl- Timberol 0.00046900 Benzoic acid, 2-hydroxy-, 3-methyl-2-buten-1-yl 68555-58-8 Prenyl Salicylate 0.00045700 ester 50 2H-1,5-Benzodioxepin-3(4H)-one, 7-(1- 950919-28-5 Cascalone 0.00045500 methylethyl)- Butanal, 4-(octahydro-4,7-methano-5H-inden-5- 30168-23-1 Dupical 0.00044100 ylidene)- 55 Cyclopenta[g]-2-benzopyran, 1,3, 4,6,7,8- 1222-05-5 Galaxolide 0.00041400 hexahydro-4,6,6,7,8,8-hexamethyl-

12 EP 2 961 374 B1

(continued)

Vapor Pressure CAS Number Chemical name Common Name** (Torr at 25°C)* 5 Cyclopentanone, 2-[2-(4-methyl-3-cyclohexen-1- 1222-05-5 Nectaryl 0.00036700 yl)propyl]- 2(3H)-Naphthalenone, 4,4a,5,6,7, 8-hexahydro- 4674-50-4 Nootkatone 0.00035800 4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)- 10 3487-99-8 2-Propenoic acid, 3-phenyl-, pentyl ester Amyl Cinnamate 0.00035200 118-71-8 4H-Pyran-4-one, 3-hydroxy-2-methyl- Maltol 0.00033700 1-Propanol, 2-methyl-3-[(1,7,7- 128119-70-0 Bornafix 0.00033400 trimethylbicyclo[2.2.1]hept-2-yl) oxy]- 15 1-Naphthalenol, 1,2,3,4,4a,5,8, 8a-octahydro- 103614-86-4 Octalynol 0.00033200 2,2,6,8-tetramethyl- 2-Butenoic acid, 2-methyl-, (2E)-3,7-dimethyl-2,6- 7785-33-3 Geranyl Tiglate 0.00033200 octadien-1-yl ester, (2E)- 20 1,3-Dioxane, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5- 117933-89-8 Karanal 0.00033100 methyl-5-(1-methylpropyl)- 629-92-5 Nonadecane Nonadecane 0.00032500 4-Penten-2-ol, 3-methyl-5-(2,2,3-trimethyl-3- 67801-20-1 Ebanol 0.00028100 25 cyclopenten-1-yl)- Propanoic acid, 2-methyl-, 2-methyl-4-oxo-4H- 65416-14-0 Maltol Isobutyrate 0.00028000 pyran-3-yl ester 2-Buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3- 28219-61-6 Laevo Trisandol 0.00028000 30 cyclopenten-1-yl)- 1,6-Methanonaphthalen-1(2H)-ol, octahydro- 5986-55-0 Healingwood 0.00027800 4,8a,9,9-tetramethyl-, (1R,4S,4aS,6R,8aS)- 2H-1,5-Benzodioxepin-3(4H)-one, 7-(1,1- 195251-91-3 Transluzone 0.00026500 35 dimethylethyl)- 120-51-4 Benzoic acid, phenylmethyl ester Benzyl Benzoate 0.00025400 3100-36-5 8-Cyclohexadecen-1-one Cyclohexadecenone 0.00025300 65405-77-8 Benzoic acid, 2-hydroxy-, (3Z)-3-hexen-1-yl ester cis-3-Hexenyl salicylate 0.00024600 40 4940-11-8 4H-Pyran-4-one, 2-ethyl-3-hydroxy- Ethyl Maltol 0.00022800 541-91-3 Cyclopentadecanone, 3-methyl- Muskone 0.00017600 118-58-1 Benzoic acid, 2-hydroxy-, phenylmethyl ester Benzyl salicylate 0.00017500 45 81783-01-9 6,8-Nonadien-3-one, 2,4,4,7-tetramethyl-, oxime Labienoxime 0.00017300 25485-88-5 Benzoic acid, 2-hydroxy-, cyclohexyl ester Cyclohexyl Salicylate 0.00017300 Amyl Cinnamic 91-87-2 Benzene, [2-(dimethoxymethyl)-1-hepten-1-yl]- Aldehyde Dimethyl 0.00016300 50 Acetal 3-Cyclopentene-1-butanol, β,2,2, 3-tetramethyl-δ- 104864-90-6 Firsantol 0.00016000 methylene- 224031-70-3 4-Penten-1-one, 1-spiro[4.5]dec-7-en-7-yl- Spirogalbanone 0.00015300 55 Acetic acid, 2-(1-oxopropoxy)-, 1-(3,3- 236391-76-7 Romandolide® 0.00012400 dimethylcyclohexyl)ethyl ester

13 EP 2 961 374 B1

(continued)

Vapor Pressure CAS Number Chemical name Common Name** (Torr at 25°C)* 5 2-Penten-1-ol, 5-[(1R,3R,6S)-2,3- 115-71-9 dimethyltricyclo[2.2.1.02,6]hept-3-yl]-2-methyl-, cis-alpha-Santalol 0.00011800 (2Z)- 4-Penten-2-ol, 3,3-dimethyl-5-(2, 2,3-trimethyl-3- 107898-54-4 Polysantol® 0.00011700 10 cyclopenten-1-yl) 5,8-Methano-2H-1-benzopyran-2-one, 6- 107898-54-4 Florex 0.00011000 ethylideneoctahydro- 69486-14-2 4-Cyclopentadecen-1-one, (4Z)- Exaltenone 0.00009640 15 Ethanone, 1-[(3R,3aR,7R,8aS)-2, 3,4,7,8,8a- 32388-55-9 hexahydro-3,6,8,8-tetramethyl-1H-3a,7- Vertofix® 0.00008490 methanoazulen-5-yl]- 1,3-Dioxolane, 2,4-dimethyl-2-(5, 6,7,8-tetrahydro- 131812-67-4 Okoumal® 0.00007600 5,5,8,8-tetramethyl-2-naphthalenyl)- 20 106-02-5 Oxacyclohexadecan-2-one Exaltolide® 0.00006430 1-Propanol, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2- 141773-73-1 Helvetolide® 0.00005790 methyl-, 1-propanoate

25 63314-79-4 5-Cyclopentadecen-1-one, 3-methyl- Delta Muscenone 0.00005650 2-Penten-1-ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3- 77-42-9 cis-beta-Santalol 0.00004810 methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)- 2H-1,5-Benzodioxepin-3(4H)-one, 7-(3- 362467-67-2 Azurone 0.00004770 30 methylbutyl)- Ethanone, 1-(2,6,10-trimethyl-2, 5,9- 28371-99-5 Trimofix O 0.00004580 cyclododecatrien-1-yl)- 1H-3a,6-Methanoazulene-3-methanol, octahydro- 16223-63-5 Khusimol 0.00004400 35 7,7-dimethyl-8-methylene-, (3S,3aR, 6R,8aS)- 10461-98-0 Benzeneacetonitrile, α-cyclohexylidene- Peonile 0.00004290 Benzoic acid, 2-[(2-methylpentylidene)amino]-, 50607-64-2 Mevantraal 0.00004070 methyl ester

40 94-47-3 Benzoic acid, 2-phenylethyl ester Phenyl Ethyl Benzoate 0.00003480 3100-36-5 Cyclohexadec-8-en-1-one Globanone® 0.00003310 Cyclohexanol, 4-(1,7,7-trimethylbicyclo[2.2.1]hept- 66072-32-0 Iso Bornyl Cyclohexanol 0.00003010 2-yl)- 45 3-Cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4- 31906-04-4 Lyral® 0.00002940 methylpentyl)- Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8- 21145-77-7 Musk Plus 0.00002860 hexamethyl-2-naphthalenyl)- 50 Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8- 21145-77-7 Fixolide 0.00002860 hexamethyl-2-naphthalenyl)- 22442-01-9 2-Cyclopentadecen-1-one, 3-methyl- Muscenone 0.00002770 109-29-5 Oxacycloheptadecan-2-one Silvanone Ci 0.00002600 55 Para Cresyl Phenyl 101-94-0 Benzeneacetic acid, 4-methylphenyl ester 0.00002330 Acetate

14 EP 2 961 374 B1

(continued)

Vapor Pressure CAS Number Chemical name Common Name** (Torr at 25°C)* 5 Phenyl Ethyl Phenyl 102-20-5 Benzeneacetic acid, 2-phenylethyl ester 0.00002300 Acetate 118562-73-5 Cyclododecaneethanol, β-methyl- Hydroxyambran 0.00001800 103-41-3 2-Propenoic acid, 3-phenyl-, phenylmethyl ester Benzyl Cinnamate 0.00001050 10 Benzoic acid, 2,4-dihydroxy-3,6-dimethyl-, methyl 4707-47-5 Veramoss 0.00001050 ester Naphtho[2,1-b]furan-6(7H)-one, 8,9-dihydro-1,5,8- 183551-83-9 Myrrhone 0.00000977 trimethyl-, (8R)- 15 Para Anisyl Phenyl 102-17-0 Benzeneacetic acid, (4-methoxyphenyl)methyl ester 0.00000813 Acetate Benzene, 2-methoxy-1-(phenylmethoxy)-4-(1- 120-11-6 Benzyl Iso Eugenol 0.00000676 propen-1-yl)- 20 Benzeneacetic acid, (2E)-3,7-dimethyl-2,6- 102-22-7 Geranyl Phenylacetate 0.00000645 octadien-1-yl ester 111879-80-2 Oxacyclohexadec-12-en-2-one, (12E)- Habanolide 100% 0.00000431 87-22-9 Benzoic acid, 2-hydroxy-, 2-phenylethyl ester Phenyl Ethyl Salicylate 0.00000299 25 2-Propenoic acid, 3-phenyl-, 1-ethenyl-1,5-dimethyl- 78-37-5 Linalyl Cinnamate 0.00000174 4-hexen-1-yl ester 28645-51-4 Oxacycloheptadec-10-en-2-one Ambrettolide 0.00000139

30 123-69-3 Oxacycloheptadec-8-en-2-one, (8Z)- Ambrettolide 0.00000136 3391-83-1 1,7-Dioxacycloheptadecan-8-one Musk RI 0.00000057 68527-79-7 7-Octen-2-ol, 8-(1H-indol-1-yl)-2,6-dimethyl- Indolene 0.000000445 54982-83-1 1,4-Dioxacyclohexadecane-5,16-dione Zenolide 0.00000000834 35 105-95-3 1,4-Dioxacycloheptadecane-5,17-dione Ethylene Brassylate 0.00000000313 Phenol, 4-[3-(benzoyloxy)-1-propen-1-yl]-2- 4159-29-9 Coniferyl benzoate 0.00000000170 methoxy- Benzoic acid, 2-[(1-hydroxy-3-phenylbutyl)amino]-, 144761-91-1 Trifone DIPG 0.00000000093 40 methyl ester * Vapor Pressures were acquired from Scifinder, which utilizes the ACD Software V.11.02, as described in the Test Methods Section. 1 Torr equals 133.3 Pa. ** Origin: The low volatile fragrance materials may be obtained from one or more of the following companies: Firmenich 45 (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlet, New Jer- sey), Bedoukian (Danbury, Connecticut), Sigma Aldrich (St. Louis, Missouri), Millennium Speciality Chemicals (Ol- ympia Fields, Illinois), Polarone International (Jersey City, New Jersey), and Aroma & Flavor Specialities (Danbury, Connecticut).

50 [0076] In one embodiment, the compositions of the present invention are those wherein the low volatile fragrance materials comprise at most about 30 wt%, preferably at most about 28 wt%, preferably at most about 25 wt%, preferably at most about 22 wt%, preferably at most about 20 wt%, preferably at most about 18 wt%, preferably at most about 15 wt%,, or alternatively combinations thereof, relative to the total weight of the fragrance component. Exemplary low volatile fragrance materials selected from the group consisting of the ingredients mentioned in Table 1 are preferred. However, 55 it is understood by one skilled in the art that other low volatile fragrance materials, not recited in Table 1, would also fall within the scope of the present invention, so long as they have a vapor pressure < 0.001 Torr at 25°C. [0077] In another aspect, the compositions of the present invention further comprises one or more volatile fragrance

15 EP 2 961 374 B1

material having a vapor pressure ≥ 0.001 Torr at 25°C (according to the reference program Advanced Chemistry De- velopment (ACD/Labs) Software Version 11.02, (© 1994-2013)). Examples of volatile fragrance materials are listed in the Table 2 hereinafter.

5 Table 2 -Volatile Fragrance Materials for Use in the Compositions Vapor CAS Number Chemical name Common Name** Pressure (Torr at 25°C)*

10 107-31-3 Formic acid, methyl ester Methyl Formate 732.00000000 75-18-3 Methane, 1,1’-thiobis- Dimethyl Sulfide 1.0% In DEP 647.00000000 141-78-6 Acetic acid ethyl ester Ethyl Acetate 112.00000000 105-37-3 Propanoic acid, ethyl ester Ethyl Propionate 44.50000000 15 110-19-0 Acetic acid, 2-methylpropyl ester Isobutyl Acetate 18.00000000 105-54-4 Butanoic acid, ethyl ester Ethyl Butyrate 13.90000000 14765-30-1 1-Butanol Butyl Alcohol 8.52000000

20 7452-79-1 Butanoic acid, 2-methyl-, ethyl ester Ethyl-2-Methyl Butyrate 7.85000000 123-92-2 1-Butanol, 3-methyl-, 1-acetate Iso Amyl Acetate 5.68000000 66576-71-4 Butanoic acid, 2-methyl-, 1-methylethyl ester Iso Propyl 2-Methylbutyrate 5.10000000 110-43-0 2-Heptanone Methyl Amyl Ketone 4.73000000 25 6728-26-3 2-Hexenal, (2E)- Trans-2 Hexenal 4.62000000 123-51-3 1-Butanol, 3-methyl- Isoamyl Alcohol 4.16000000 1191-16-8 2-Buten-1-ol, 3-methyl-, 1-acetate Prenyl acetate 3.99000000

30 57366-77-5 1,3-Dioxolane-2-methanamine, N-methyl- Methyl Dioxolan 3.88000000 Bicyclo[3.1.1]hept-2-ene, 2,6, 6-trimethyl-, 7785-70-8 Alpha Pinene 3.49000000 (1R,5R)- Bicyclo[2.2.1]heptane, 2,2-dimethyl-3- 79-92-5 Camphene 3.38000000 35 methylene- 4-Methoxy-2-Methyl-2- 94087-83-9 2-Butanethiol, 4-methoxy-2-methyl- 3.31000000 Butanenthiol 39255-32-8 Pentanoic acid, 2-methyl-, ethyl ester Manzanate 2.91000000 40 Bicyclo[3.1.0]hexane, 4-methylene-1-(1- 3387-41-5 Sabinene 2.63000000 methylethyl)- Bicyclo[3.1.1]heptane, 6,6-dimethyl-2- 127-91-3 Beta Pinene 2.40000000 methylene- 45 105-68-0 1-Butanol, 3-methyl-, 1-propanoate Amyl Propionate 2.36000000 123-35-3 1,6-Octadiene, 7-methyl-3-methylene- Myrcene 2.29000000 124-13-0 Octanal Octyl Aldehyde 2.07000000 7392-19-0 2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl- Limetol 1.90000000 50 111-13-7 2-Octanone Methyl Hexyl Ketone 1.72000000 123-66-0 Hexanoic acid, ethyl ester Ethyl Caproate 1.66000000 470-82-6 2-Oxabicyclo[2.2.2]octane, 1, 3,3-trimethyl- Eucalyptol 1.65000000 55 99-87-6 Benzene, 1-methyl-4-(1-methylethyl)- Para Cymene 1.65000000 104-93-8 Benzene, 1-methoxy-4-methyl- Para Cresyl Methyl Ether 1.65000000

16 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 13877-91-3 1,3,6-Octatriene, 3,7-dimethyl- Ocimene 1.56000000 138-86-3 Cyclohexene, 1-methyl-4-(1-methylethenyl)- dl-Limonene 1.54000000 Cyclohexene, 1-methyl-4-(1-methylethenyl)-, 5989-27-5 d-limonene 1.54000000 10 (4R)- 106-68-3 3-Octanone Ethyl Amyl Ketone 1.50000000 110-41-8 Undecanal, 2-methyl- Methyl Nonyl Acetaldehyde 1.43000000 142-92-7 Acetic acid, hexyl ester Hexyl acetate 1.39000000 15 110-93-0 5-Hepten-2-one, 6-methyl- Methyl Heptenone 1.28000000 81925-81-7 2-Hepten-4-one, 5-methyl- Filbertone 1% in TEC 1.25000000 3681-71-8 3-Hexen-1-ol, 1-acetate, (3Z)- cis-3-Hexenyl acetate 1.22000000 20 97-64-3 Propanoic acid, 2-hydroxy-, ethyl ester Ethyl Lactate 1.16000000 Cyclohexene, 1-methyl-4-(1- 586-62-9 Terpineolene 1.13000000 methylethylidene)- 51115-64-1 Butanoic acid, 2-methylbutyl ester Amyl butyrate 1.09000000 25 106-27-4 Butanoic acid, 3-methylbutyl ester Amyl Butyrate 1.09000000 1,4-Cyclohexadiene, 1-methyl-4-(1- 99-85-4 Gamma Terpinene 1.08000000 methylethyl)- 18640-74-9 Thiazole, 2-(2-methylpropyl)- 2-Isobutylthiazole 1.07000000 30 928-96-1 3-Hexen-1-ol, (3Z)- cis-3-Hexenol 1.04000000 100-52-7 Benzaldehyde Benzaldehyde 0.97400000 141-97-9 Butanoic acid, 3-oxo-, ethyl ester Ethyl Acetoacetate 0.89000000 35 928-95-0 2-Hexen-1-ol, (2E)- Trans-2-Hexenol 0.87300000 928-94-9 2-Hexen-1-ol, (2Z)- Beta Gamma Hexenol 0.87300000 Cyclohexane, 3-ethoxy-1,1,5-trimethyl-, cis- 24691-15-4 Herbavert 0.85200000 (9CI) 40 4-Methyl-4-Mercaptopentan-2- 19872-52-7 2-Pentanone, 4-mercapto-4-methyl- 0.84300000 one 1ppm TEC 3016-19-1 2,4,6-Octatriene, 2,6-dimethyl-, (4E,6E)- Allo-Ocimene 0.81600000 Oxirane, 2,2-dimethyl-3-(3-methyl-2,4- 45 69103-20-4 Myroxide 0.80600000 pentadien-1-yl)- 189440-77-5 4,7-Octadienoic acid, methyl ester, (4E)- Anapear 0.77700000 67633-96-9 Carbonic acid, (3Z)-3-hexen-1-yl methyl ester Liffarome™ 0.72100000

50 123-68-2 Hexanoic acid, 2-propen-1-yl ester Allyl Caproate 0.67800000 106-72-9 5-Heptenal, 2,6-dimethyl- Melonal 0.62200000 106-30-9 Heptanoic acid, ethyl ester Ethyl Oenanthate 0.60200000 3-Cyclohexene-1-carboxaldehyde, 2,4- 68039-49-6 Ligustral or Triplal 0.57800000 55 dimethyl- Phenyl Acetaldehyde Dimethyl 101-48-4 Benzene, (2,2-dimethoxyethyl)- 0.55600000 Acetal

17 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1- 16409-43-1 Rose Oxide 0.55100000 propen-1-yl)- 925-78-0 3-Nonanone Ethyl Hexyl Ketone 0.55100000 10 100-47-0 Benzonitrile Benzyl Nitrile 0.52400000 589-98-0 3-Octanol Octanol-3 0.51200000 58430-94-7 1-Hexanol, 3,5,5-trimethyl-, 1-acetate Iso Nonyl Acetate 0.47000000 10250-45-0 4-Heptanol, 2,6-dimethyl-, 4-acetate Alicate 0.45400000 15 105-79-3 Hexanoic acid, 2-methylpropyl ester Iso Butyl Caproate 0.41300000 2349-07-7 Propanoic acid, 2-methyl-, hexyl ester Hexyl isobutyrate 0.41300000 Cyclohexanecarboxylic acid, 1,4-dimethyl-, 23250-42-2 Cyprissate 0.40500000 20 methyl ester, trans- 122-78-1 Benzeneacetaldehyde Phenyl acetaldehyde 0.36800000 5405-41-4 Butanoic acid, 3-hydroxy-, ethyl ester Ethyl-3-Hydroxy Butyrate 0.36200000 105-53-3 Propanedioic acid, 1,3-diethyl ester Diethyl Malonate 0.34400000 25 93-58-3 Benzoic acid, methyl ester Methyl Benzoate 0.34000000 16356-11-9 1,3,5-Undecatriene Undecatriene 0.33600000 65405-70-1 4-Decenal, (4E)- Decenal (Trans-4) 0.33100000

30 54546-26-8 1,3-Dioxane, 2-butyl-4,4,6-trimethyl- Herboxane 0.33000000 13254-34-7 2-Heptanol, 2,6-dimethyl- Dimethyl-2 6-Heptan-2-ol 0.33000000 98-86-2 Ethanone, 1-phenyl- Acetophenone 0.29900000 93-53-8 Benzeneacetaldehyde, α-methyl- Hydratropic aldehyde 0.29400000 35 Propanoic acid, 2-methyl-, 1, 3-dimethyl-3- 80118-06-5 Iso Pentyrate 0.28500000 buten-1-yl ester 557-48-2 2,6-Nonadienal, (2E,6Z)- E Z-2,6-Nonadien-1-al 0.28000000

40 24683-00-9 Pyrazine, 2-methoxy-3-(2-methylpropyl)- 2-Methoxy-3-Isobutyl Pyrazine 0.27300000 104-57-4 Formic acid, phenylmethyl ester Benzyl Formate 0.27300000 104-45-0 Benzene, 1-methoxy-4-propyl- Dihydroanethole 0.26600000 Cyclohexanone, 5-methyl-2-(1-methylethyl)-, 491-07-6 Iso Menthone 0.25600000 45 (2R,5R)-rel- Cyclohexanone, 5-methyl-2-(1-methylethyl)-, 89-80-5 Menthone Racemic 0.25600000 (2R,5S)-rel- 2463-53-8 2-Nonenal 2 Nonen-1-al 0.25600000 50 55739-89-4 Cyclohexanone, 2-ethyl-4,4-dimethyl- Thuyacetone 0.25000000 150-78-7 Benzene, 1,4-dimethoxy- Hydroquinone Dimethyl Ether 0.25000000 64988-06-3 Benzene, 1-(ethoxymethyl)-2-methoxy- Rosacene 0.24600000 76-22-2 Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl- Camphor gum 0.22500000 55 67674-46-8 2-Hexene, 6,6-dimethoxy-2,5, 5-trimethyl- Methyl pamplemousse 0.21400000 112-31-2 Decanal Decyl Aldehyde 0.20700000

18 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 16251-77-7 Benzenepropanal, β-methyl- Trifernal 0.20600000 93-92-5 Benzenemethanol, α-methyl-, 1-acetate Methylphenylcarbinol acetate 0.20300000 143-13-5 Acetic acid, nonyl ester Nonyl Acetate 0.19700000 10 122-00-9 Ethanone, 1-(4-methylphenyl)- Para Methyl Acetophenone 0.18700000 24237-00-1 2H-Pyran, 6-butyl-3,6-dihydro-2,4-dimethyl- Gyrane 0.18600000 Propanoic acid, 2-methyl-, (3Z)-3-hexen-1-yl 41519-23-7 Hexenyl isobutyrate 0.18200000 ester 15 93-89-0 Benzoic acid, ethyl ester Ethyl Benzoate 0.18000000 20780-48-7 3-Octanol, 3,7-dimethyl-, 3-acetate Tetrahydro Linalyl Acetate 0.18000000 1-Hexanol, 5-methyl-2-(1-methylethyl)-, 1- 40853-55-2 Tetrahydro Lavandulyl Acetate 0.17300000 20 acetate 933-48-2 Cyclohexanol, 3,3,5-trimethyl-, (1R,5R)-rel- Trimethylcyclohexanol 0.17300000 35158-25-9 2-Hexenal, 5-methyl-2-(1-methylethyl)- Lactone of Cis Jasmone 0.17200000 18479-58-8 7-Octen-2-ol, 2,6-dimethyl- Dihydromyrcenol 0.16600000 25 140-11-4 Acetic acid, phenylmethyl ester Benzyl acetate 0.16400000 14765-30-1 Cyclohexanone, 2-(1-methylpropyl)- 2-sec-Butyl Cyclo Hexanone 0.16300000 20125-84-2 3-Octen-1-ol, (3Z)- Octenol 0.16000000

30 142-19-8 Heptanoic acid, 2-propen-1-yl ester Allyl Heptoate 0.16000000 100-51-6 Benzenemethanol Benzyl Alcohol 0.15800000 10032-15-2 Butanoic acid, 2-methyl-, hexyl ester Hexyl-2-Methyl Butyrate 0.15800000 695-06-7 2(3H)-Furanone, 5-ethyldihydro- Gamma Hexalactone 0.15200000 35 21722-83-8 Cyclohexaneethanol, 1-acetate Cyclohexyl Ethyl Acetate 0.15200000 111-79-5 2-Nonenoic acid, methyl ester Methyl-2-Nonenoate 0.14600000 16491-36-4 Butanoic acid, (3Z)-3-hexen-1-yl ester Cis 3 Hexenyl Butyrate 0.13500000 40 111-12-6 2-Octynoic acid, methyl ester Methyl Heptine Carbonate 0.12500000 59323-76-1 1,3-Oxathiane,2-methyl-4-propyl-, (2R,4S)-rel- Oxane 0.12300000 62439-41-2 Heptanal, 6-methoxy-2,6-dimethyl- Methoxy Melonal 0.11900000 Bicyclo[2.2.1]heptan-2-ol, 1, 3,3-trimethyl-, 2- 45 13851-11-1 Fenchyl Acetate 0.11700000 acetate 115-95-7 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate Linalyl acetate 0.11600000 18479-57-7 2-Octanol, 2,6-dimethyl- Tetra-Hydro Myrcenol 0.11500000

50 111-87-5 1-Octanol Octyl Alcohol 0.11400000 3-Cyclohexene-1-methanethiol, α,α,4- 71159-90-5 Grapefruit mercaptan 0.10500000 trimethyl- Cyclohexanemethanol, α,α,4-trimethyl-, 1- 80-25-1 Menthanyl Acetate 0.10300000 acetate 55 88-41-5 Cyclohexanol,2-(1,1-dimethylethyl)-, 1-acetate Verdox™ 0.10300000 32210-23-4 Cyclohexanol,4-(1,1-dimethylethyl)-, 1-acetate Vertenex 0.10300000

19 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 24168-70-5 Pyrazine, 2-methoxy-3-(1-methylpropyl)- Methoxyisobutylpyrazine 0.09950000 Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, 89-79-2 Iso-Pulegol 0.09930000 (1R,2S,5R)- 10 112-12-9 2-Undecanone Methyl Nonyl Ketone 0.09780000 103-05-9 Benzenepropanol, α,α-dimethyl- Phenyl Ethyl Dimethyl Carbinol 0.09770000 Bicyclo[2.2.1]heptan-2-ol, 1, 7,7-trimethyl-, 2- 125-12-2 Iso Bornyl Acetate 0.09590000 acetate, (1R, 2R,4R)-rel- 15 78-70-6 1,6-Octadien-3-ol, 3,7-dimethyl- Linalool 0.09050000 101-97-3 Benzeneacetic acid, ethyl ester Ethyl Phenyl Acetate 0.08970000 100-86-7 Benzeneethanol, α,α-dimethyl- Dimethyl Benzyl Carbinol 0.08880000

20 Cyclopropanecarboxylic acid, (3Z)-3-hexen-1- 188570-78-7 Montaverdi 0.08640000 yl ester 3-Cyclohexene-1-methanol, 3, 5-dimethyl-, 1- 67634-25-7 Floralate 0.08500000 acetate

25 112-44-7 Undecanal Undecyl Aldehyde 0.08320000 32669-00-4 Ethanone, 1-(3-cycloocten-1-yl)- Tanaisone® 0.08150000 98-53-3 Cyclohexanone, 4-(1,1-dimethylethyl)- Patchi 0.07780000 35854-86-5 6-Nonen-1-ol, (6Z)- cis-6-None-1-ol 0.07770000 30 5331-14-6 Benzene, (2-butoxyethyl)- Butyl phenethyl ether 0.07760000 80-57-9 Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl- Verbenone 0.07730000 Cyclohexanecarboxylic acid, 2,2,6-trimethyl-, 22471-55-2 Thesaron 0.07670000 ethyl ester, (1R,6S)-rel- 35 60-12-8 Benzeneethanol Phenethyl alcohol 0.07410000 106-26-3 2,6-Octadienal, 3,7-dimethyl-, (2Z)- Neral 0.07120000 5392-40-5 2,6-Octadienal, 3,7-dimethyl- Citral 0.07120000 40 Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1- 89-48-5 Menthyl Acetate 0.07070000 acetate, (1R, 2S,5R)-rel- 119-36-8 Benzoic acid, 2-hydroxy-, methyl ester Methyl salicylate 0.07000000 4180-23-8 Benzene, 1-methoxy-4-(1E)-1-propen-1-yl- Anethol 0.06870000 45 7549-37-3 2,6-Octadiene, 1,1-dimethoxy-3,7-dimethyl- Citral Dimethyl Acetal 0.06780000 Cyclohexanemethanol, α,3,3-trimethyl-, 1- 25225-08-5 Aphermate 0.06780000 formate 3913-81-3 2-Decenal, (2E)- 2-Decene-1-al 0.06740000 50 15373-31-6 3-Cyclopentene-1-acetonitrile, 2,2,3-trimethyl- Cantryl® 0.06700000 2-Cyclohexen-1-one, 2-methyl-5-(1- 6485-40-1 Laevo carvone 0.06560000 methylethenyl)-, (5R)-

55 16587-71-6 Cyclohexanone, 4-(1,1-dimethylpropyl)- Orivone 0.06490000 6,10-Dioxaspiro[4.5]decane, 8,8-dimethyl- 62406-73-9 Opalal CI 0.06290000 7-(1-methylethyl)-

20 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 3720-16-9 2-Cyclohexen-1-one, 3-methyl-5-propyl- Livescone 0.06270000 13816-33-6 Benzonitrile, 4-(1-methylethyl)- Cumin Nitrile 0.06230000 67019-89-0 2,6-Nonadienenitrile Violet Nitrile 0.06200000 10 Butanoic acid, 2-methyl-, (3Z) -3-hexen-1-yl cis-3-Hexenyl Alpha Methyl 53398-85-9 0.06130000 ester Butyrate 16510-27-3 Benzene, 1-(cyclopropylmethyl)-4-methoxy- Toscanol 0.05870000 111-80-8 2-Nonynoic acid, methyl ester Methyl Octine Carbonate 0.05680000 15 103-45-7 Acetic acid, 2-phenylethyl ester Phenyl Ethyl Acetate 0.05640000 13491-79-7 Cyclohexanol, 2-(1,1-dimethylethyl)- Verdol 0.05430000 7786-44-9 2,6-Nonadien-1-ol 2,6-Nonadien-1-ol 0.05370000 20 103-28-6 Propanoic acid, 2-methyl-, phenylmethyl ester Benzyl Iso Butyrate 0.05130000 Bicyclo[2.2.1]heptan-2-ol, 1, 2,3,3- 28462-85-3 Humus Ether 0.04870000 tetramethyl-, (1R,2R, 4S)-rel- 122-03-2 Benzaldehyde, 4-(1-methylethyl)- Cuminic Aldehyde 0.04820000 25 358331-95-0 2,5-Octadien-4-one, 5,6,7-trimethyl-, (2E)- Pomarose 0.04810000 3-Cyclohexen-1-ol, 4-methyl-1-(1- 562-74-3 Terpinenol-4 0.04780000 methylethyl)- 68527-77-5 3-Cyclohexene-1-methanol, 2, 4,6-trimethyl- Isocyclogeraniol 0.04640000 30 35852-46-1 Pentanoic acid, (3Z)-3-hexen-1-yl ester Cis-3-Hexenyl Valerate 0.04580000 Bicyclo[2.2.1]heptan-2-ol, 1, 7,7-trimethyl-, 2- 2756-56-1 Iso Bornyl Propionate 0.04540000 propanoate, (1R,2R,4R)-rel- Benzene, 1-methyl-4-(1-methylethyl)-2-(1- 35 14374-92-6 Verdoracine 0.04460000 propen-1-yl)- 6784-13-0 3-Cyclohexene-l-propanal, β, 4-dimethyl- Limonenal 0.04380000 41884-28-0 1-Hexanol, 5-methyl-2-(1-methylethyl)-, (2R)- Tetrahydro Lavandulol 0.04230000 40 22457-23-4 3-Heptanone, 5-methyl-, oxime Stemone® 0.04140000 104-50-7 2(3H)-Furanone, 5-butyldihydro- Gamma Octalactone 0.04080000 143-08-8 1-Nonanol Nonyl Alcohol 0.04070000 Acetic acid, 2-(3-methylbutoxy)-, 2-propen-1-yl 45 67634-00-8 Allyl Amyl Glycolate 0.04000000 ester Bicyclo[2.2.1]heptan-2-ol, 1, 7,7-trimethyl-, 464-45-9 1-Borneol 0.03980000 (1S,2R,4S)- Bicyclo[2.2.1]heptan-2-ol, 1, 7,7-trimethyl-, 1.7.7-Trimethyl-Bicyclo-1.2.2- 50 124-76-5 0.03980000 (1R,2R,4R)-rel- Heptanol-2 Cyclohexanol, 2-(1,1-dimethylpropyl)-, 1- 67874-72-0 Coniferan 0.03980000 acetate 3-Cyclohexene-1-methanol, α, α,4-trimethyl-, 80-26-2 Terpinyl Acetate 0.03920000 55 1-acetate 498-81-7 Cyclohexanemethanol, α,α,4-trimethyl- Dihydro Terpineol 0.03920000

21 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 112-45-8 10-Undecenal Undecylenic aldehyde 0.03900000 2,4-Cyclohexadiene-1-carboxylic acid, 2,6,6- 35044-57-6 Ethyl Safranate 0.03880000 trimethyl-, ethyl ester 10 106-21-8 1-Octanol, 3,7-dimethyl- Dimethyl Octanol 0.03860000 82461-14-1 Furan, tetrahydro-2,4-dimethyl-4-phenyl- Rhubafuran® 0.03780000 56011-02-0 Benzene, [2-(3-methylbutoxy) ethyl]- Phenyl Ethyl Isoamyl Ether 0.03690000 103-37-7 Butanoic acid, phenylmethyl ester Benzyl Butyrate 0.03660000 15 118-61-6 Benzoic acid, 2-hydroxy-, ethyl ester Ethyl salicylate 0.03480000 98-52-2 Cyclohexanol, 4-(1,1-dimethylethyl)- Patchon 0.03480000 115-99-1 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-formate Linalyl Formate 0.03440000 20 112-54-9 Dodecanal Lauric aldehyde 0.03440000 53046-97-2 3,6-Nonadien-1-ol, (3Z,6Z)- 3,6 Nonadien-1-ol 0.03360000 76649-25-7 3,6-Nonadien-1-ol 3,6-Nonadien-1-ol 0.03360000

25 1975-78-6 Decanenitrile Decanonitrile 0.03250000 Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 2216-51-5 L-Menthol 0.03230000 (1R,2S,5R)- Propanoic acid, 2-methyl-, 4-methylphenyl 103-93-5 Para Cresyl iso-Butyrate 0.03120000 ester 30 Propanoic acid, 2-methyl-, (1R,2S,4R)-1,7,7- 24717-86-0 Abierate 0.03110000 trimethylbicyclo[2.2.1]hept-2-yl ester, rel- 67845-46-9 Acetaldehyde, 2-(4-methylphenoxy)- Aldehyde XI 0.03090000 2-Butenoic acid, 2-methyl-, (3Z)-3-hexen-1-yl 35 67883-79-8 Cis-3-Hexenyl Tiglate 0.03060000 ester, (2E)- Bicyclo[3.1.1]hept-2-ene-2-propanal, 6,6- 33885-51-7 Pino Acetaldehyde 0.03040000 dimethyl-

40 70214-77-6 2-Nonanol, 6,8-dimethyl- Nonadyl 0.03010000 215231-33-7 Cyclohexanol, 1-methyl-3-(2-methylpropyl)- Rossitol 0.02990000 120-72-9 1H-Indole Indole 0.02980000 2463-77-6 2-Undecenal 2-Undecene-1-al 0.02970000 45 675-09-2 2H-Pyran-2-one, 4,6-dimethyl- Levistamel 0.02940000 98-55-5 3-Cyclohexene-1-methanol, α, α,4-trimethyl- alpha-Terpineol 0.02830000 81786-73-4 3-Hepten-2-one, 3,4,5,6,6-pentamethyl-, (3Z)- Koavone 0.02750000

50 39212-23-2 2(3H)-Furanone, 5-butyldihydro-4-methyl- Methyl Octalactone 0.02700000 53767-93-4 7-Octen-2-ol, 2,6-dimethyl-, 2-acetate Dihydro Terpinyl Acetate 0.02690000 104-55-2 2-Propenal, 3-phenyl- Cinnamic Aldehyde 0.02650000 144-39-8 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-propanoate Linalyl Propionate 0.02630000 55 3,7-Dimethyl-1,6-nonadien-3- 61931-80-4 1,6-Nonadien-3-ol, 3,7-dimethyl-, 3-acetate 0.02630000 yl acetate

22 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 65443-14-3 Cyclopentanone, 2,2,5-trimethyl-5-pentyl- veloutone 0.02610000 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, 141-12-8 Neryl Acetate 0.02560000 (2Z)- 10 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, 105-87-3 Geranyl acetate 0.02560000 (2E)- Methyl Nonyl Acetaldehyde 68141-17-3 Undecane, 1,1-dimethoxy-2-methyl- 0.02550000 Dimethyl Acetal 15 2206-94-2 Benzenemethanol, α-methylene-, 1-acetate Indocolore 0.02550000 123-11-5 Benzaldehyde, 4-methoxy- Anisic aldehyde 0.02490000 Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, 57576-09-7 Iso Pulegol Acetate 0.02480000 1-acetate, (1R,2S,5R)- 20 51566-62-2 6-Octenenitrile, 3,7-dimethyl- Citronellyl Nitrile 0.02470000 30385-25-2 6-Octen-2-ol, 2,6-dimethyl- Dihydromyrcenol 0.02440000 101-84-8 Benzene, 1,1’-oxybis- Diphenyl Oxide 0.02230000

25 136-60-7 Benzoic acid, butyl ester 136-60-7 0.02170000 5,8-Methano-2H-1-benzopyran, 6- 93939-86-7 Rhuboflor 0.02120000 ethylideneoctahydro- 83926-73-2 Cyclohexanepropanol, α,α-dimethyl- Coranol 0.02100000 30 125109-85-5 Benzenepropanal, β-Methyl-3-(1-methylethyl)- Florhydral 0.02070000 104-21-2 Benzenemethanol, 4-methoxy-, 1-acetate Anisyl Acetate 0.02050000 2563-07-7 Phenol, 2-ethoxy-4-methyl- Ultravanil 0.02030000 7493-57-4 Benzene, [2-(1-propoxyethoxy)ethyl]- Acetaldehyde 0.01990000 35 141-25-3 7-Octen-1-ol, 3,7-dimethyl- Rhodinol 0.01970000 3-Methoxy-7,7-dimethyl-10- Bicyclo[4.3.1]decane, 3-methoxy-7,7-dimethyl- 216970-21-7 methylenebicyclo[4.3.1] 0.01960000 10-methylene- decane 40 Propanoic acid, 2-(1,1-dimethylpropoxy)-, 319002-92-1 Sclareolate® 0.01960000 propyl ester, (2S)- 85-91-6 Benzoic acid, 2-(methylamino)-, methyl ester Dimethyl anthranilate 0.01930000

45 7540-51-4 6-Octen-1-ol, 3,7-dimethyl-, (3S)- L-Citronellol 0.01830000 543-39-5 7-Octen-2-ol, 2-methyl-6-methylene- Myrcenol 0.01820000 18479-54-4 4,6-Octadien-3-ol, 3,7-dimethyl- Muguol 0.01800000 5-Oxatricyclo[8.2.0.04,6] dodecane, 4,9,12,12- 1209-61-6 Tobacarol 0.01730000 50 tetramethyl- 2-Cyclohexene-1-carboxylic acid, 2-ethyl-6,6- 57934-97-1 Givescone 0.01710000 dimethyl-, ethyl ester 3-Buten-2-one, 4-(2,6,6-trimethyl-1- 79-77-6 beta-Ionone 0.01690000 55 cyclohexen-1-yl)-, (3E)- 4,7-Methano-1H-inden-5-ol, octahydro-, 5- 64001-15-6 Dihydro Cyclacet 0.01630000 acetate

23 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 134-20-3 Benzoic acid, 2-amino-, methyl ester Methyl anthranilate 0.01580000 Spiro 1,3-dioxolane-2,8’(5’H)-[2H-2,4a] 154171-77-4 methanonaphthalene], hexahydro-1’,1’,5’,5’- Ysamber K® 0.01470000 10 tetramethyl-, (2’S,4’aS,8’aS)-(9CI) Spiro 1,3-dioxolane-2,8’(5’H)-[2H- 154171-76-3 2,4a]methanonaphthalene], hexahydro- Ysamber 0.01470000 1’,1’,5’,5’-tetramethyl- 3-Buten-2-one, 4-(2,6,6-trimethyl-2- 15 127-41-3 alpha-Ionone 0.01440000 cyclohexen-1-yl)-, (3E)- Dimethyl Benzyl Carbinyl 151-05-3 Benzeneethanol, α,α-dimethyl-, 1-acetate 0.01390000 Acetate 4,7-Methano-1H-inden-5-ol, 3a,4,5,6,7,7a- 20 2500-83-6 Flor Acetate 0.01370000 hexahydro-, 5-acetate 150-84-5 6-Octen-1-ol, 3,7-dimethyl-, 1-acetate Citronellyl acetate 0.01370000 2H-Pyran, tetrahydro-2-methyl-4-methylene-6- 30310-41-9 Pelargene 0.01350000 phenyl- 25 Bicyclo[3.3.1]nonane, 2-ethoxy-2,6,6- 68845-00-1 Boisiris 0.01350000 trimethyl-9-methylene- 106-24-1 2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)- Geraniol 0.01330000 Bicyclo[7.2.0]undec-4-ene, 4, 11,11-trimethyl- 30 75975-83-6 Vetyvenal 0.01280000 8-methylene-, (1R,4E,9S)- 1H-3a,7-Methanoazulene, octahydro-6- 19870-74-7 methoxy-3,6,8,8-tetramethyl-, (3R,3aS,6S,7R, Cedryl methyl ether 0.01280000 8aS)- 35 Bicyclo[7.2.0]undec-4-ene, 4, 11,11-trimethyl- 87-44-5 Caryophyllene Extra 0.01280000 8-methylene-, (1R,4E,9S)- 54440-17-4 1H-Inden-1-one, 2,3-dihydro-2,3,3-trimethyl- Safraleine 0.01260000 110-98-5 2-Propanol, 1,1’-oxybis- Ambrocenide 0.01250000 40 41890-92-0 2-Octanol, 7-methoxy-3,7-dimethyl- Osyrol® 0.01250000 71077-31-1 4,9-Decadienal, 4,8-dimethyl- Floral Super 0.01230000 65-85-0 Benzoic Acid Benzoic Acid 0.01220000 45 61444-38-0 3-Hexenoic acid, (3Z)-3-hexen-1-yl ester, (3Z)- cis-3-hexenyl-cis-3-hexenoate 0.01220000 Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 116044-44-1 3-(1-methylethyl)-, ethyl ester, Herbanate 0.01210000 (1R,2S,3S,4S)-rel- 50 104-54-1 2-Propen-1-ol, 3-phenyl- Cinnamic alcohol 0.01170000 Propanoic acid, 2-methyl-, 1-ethenyl-1,5- 78-35-3 Linalyl isobutyrate 0.01170000 dimethyl-4-hexen-1-yl ester 23495-12-7 Ethanol, 2-phenoxy-, 1-propanoate Phenoxy Ethyl Propionate 0.01130000 55 103-26-4 2-Propenoic acid, 3-phenyl-, methyl ester Methyl Cinnamate 0.01120000 67634-14-4 Benzenepropanal, 2-ethyl-a,a-dimethyl- Florazon (ortho-isomer) 0.01110000

24 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 5454-19-3 Propanoic acid, decyl ester N-Decyl Propionate 0.01100000 93-16-3 Benzene, 1,2-dimethoxy-4-(1-propen-1-yl)- Methyl Iso Eugenol 0.01100000 81782-77-6 3-Decen-5-ol, 4-methyl- 4-Methyl-3-decen-5-ol 0.01070000 10 97-53-0 Phenol, 2-methoxy-4-(2-propen-1-yl)- Eugenol 0.01040000 120-57-0 1,3-Benzodioxole-5-carboxaldehyde Heliotropin 0.01040000 4826-62-4 2-Dodecenal 2 Dodecene-1-al 0.01020000

15 20407-84-5 2-Dodecenal, (2E)- Aldehyde Mandarin 0.01020000 5462-06-6 Benzenepropanal, 4-methoxy-α-methyl- Canthoxal 0.01020000 1,4-Cyclohexanedicarboxylic acid, 1,4- Dimethyl 1,4- 94-60-0 0.01020000 dimethyl ester cyclohexanedicarboxylate 20 2-Buten-1-one, 1-(2,6,6-trimethyl-3- 57378-68-4 delta-damascone 0.01020000 cyclohexen-1-yl)- 2-Butanone, 4-(2,6,6-trimethyl-1-cyclohexen- 17283-81-7 Dihydro Beta Ionone 0.01020000 1-yl)- 25 1885-38-7 2-Propenenitrile, 3-phenyl-, (2E)- Cinnamalva 0.01010000 103-48-0 Propanoic acid, 2-methyl-, 2-phenylethyl ester Phenyl Ethyl Iso Butyrate 0.00994000 2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2- 488-10-8 Cis Jasmone 0.00982000 penten-1-yl- 30 Acetaldehyde, 2-[(3,7-dimethyl-6-octen-1- 7492-67-3 Citronellyloxyacetaldehyde 0.00967000 yl)oxy]- 1-Cyclohexene-1-ethanol, 4-(1-methylethyl)-, 68683-20-5 Iso Bergamate 0.00965000 1-formate 35 3025-30-7 2,4-Decadienoic acid, ethyl ester, (2E,4Z)- Ethyl 2,4-Decadienoate 0.00954000 103-54-8 2-Propen-1-ol, 3-phenyl-, 1-acetate Cinnamyl Acetate 0.00940000 Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a- 6790-58-5 Synambran 0.00934000 tetramethyl-, (3aR,5aS,9aS, 9bR)- 40 18127-01-0 Benzenepropanal, 4-(1,1-dimethylethyl)- Bourgeonal 0.00934000 Naphtho [2,1-b]furan, dodecahydro-3a,6,6,9a- 3738-00-9 Ambroxan 0.00934000 tetramethyl- 1,4-Methanonaphthalen-5(1H) -one, 45 51519-65-4 Tamisone 0.00932000 4,4a,6,7,8,8a-hexahydro- Dodecanoic acid, 12-hydroxy-, λ-lactone 148-05-1 Dodecalactone 0.00931000 (6CI,7CI); 1,12- Cyclohexanepropanoic acid, 2-propen-1-yl 50 2705-87-5 Allyl Cyclohexane Propionate 0.00925000 ester 7011-83-8 2(3H)-Furanone, 5-hexyldihydro-5-methyl- Lactojasmone® 0.00885000 61792-11-8 2,6-Nonadienenitrile, 3,7-dimethyl- Lemonile® 0.00884000

55 692-86-4 10-Undecenoic acid, ethyl ester Ethyl Undecylenate 0.00882000 103-95-7 Benzenepropanal, α-methyl-4-(1-methylethyl)- Cymal 0.00881000 94201-19-1 1-Oxaspiro[4.5]decan-2-one, 8-methyl- Methyl Laitone 10% TEC 0.00872000

25 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 104-61-0 2(3H)-Furanone, dihydro-5-pentyl- γ-Nonalactone 0.00858000 706-14-9 2(3H)-Furanone, 5-hexyldihydro- γ -Decalactone 0.00852000 2-Buten-1-one, 1-(2,6,6-trimethyl-2- 24720-09-0 α-Damascone 0.00830000 10 cyclohexen-1-yl)-, (2E)- 2-Buten-1-one, 1-(2,4,4-trimethyl-2- 39872-57-6 Isodamascone 0.00830000 cyclohexen-1-yl)-, (2E)- 705-86-2 2H-Pyran-2-one, tetrahydro-6-pentyl- Decalactone 0.00825000 15 67634-15-5 Benzenepropanal, 4-ethyl-a,a-dimethyl- Floralozone 0.00808000 40527-42-2 1,3-Benzodioxole, 5-(diethoxymethyl)- Heliotropin Diethyl Acetal 0.00796000 4-Penten-1-one, 1-(5,5-dimethyl-1- 56973-85-4 Neobutenone α 0.00763000 cyclohexen-1-yl)- 20 Bicyclo[3.1.1]hept-2-ene-2-ethanol, 6,6- 128-51-8 Nopyl Acetate 0.00751000 dimethyl-, 2-acetate 103-36-6 2-Propenoic acid, 3-phenyl-, ethyl ester Ethyl Cinnamate 0.00729000

® 25 5182-36-5 1,3-Dioxane, 2,4,6-trimethyl-4-phenyl- Floropal 0.00709000 42604-12-6 Cyclododecane, (methoxymethoxy)- Boisambrene 0.00686000 Bicyclo[3.1.1]hept-2-ene-2-propanal, α,α,6,6- 33885-52-8 Pinyl Iso Butyrate Alpha 0.00685000 tetramethyl- 30 3288-99-1 Benzeneacetonitrile, 4-(1,1-dimethylethyl)- Marenil CI 0.00665000 2-Buten-1-one, 1-(2,6,6-trimethyl-1- 35044-68-9 beta-Damascone 0.00655000 cyclohexen-1-yl)- 1,4-Methanonaphthalen-6(2H) -one, 41724-19-0 Plicatone 0.00652000 35 octahydro-7-methyl- Bicyclo[3.2.1]octan-8-one, 1, 5-dimethyl-, 75147-23-8 Buccoxime® 0.00647000 oxime Cyclohexene, 4-(1,5-dimethyl-4-hexen-1- 495-62-5 Bisabolene 0.00630000 40 ylidene)-1-methyl- 2785-87-7 Phenol, 2-methoxy-4-propyl- Dihydro Eugenol 0.00624000 87-19-4 Benzoic acid, 2-hydroxy-, 2-methylpropyl ester Iso Butyl Salicylate 0.00613000 4430-31-3 2H-1-Benzopyran-2-one, octahydro- Octahydro Coumarin 0.00586000 45 Cyclohexanone, 2-(1-mercapto-1- 38462-22-5 Ringonol 50 TEC 0.00585000 methylethyl)-5-methyl- 2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, 77-83-8 Ethylmethylphenylglycidate 0.00571000 ethyl ester 50 3-Cyclohexene-1-carboxaldehyde, 4-(4- Iso Hexenyl Cyclohexenyl 37677-14-8 0.00565000 methyl-3-penten-1-yl)- Carboxaldehyde Propanoic acid, 2-methyl-, 2-phenoxyethyl 103-60-6 Phenoxy Ethyl iso-Butyrate 0.00562000 ester 55 18096-62-3 Indeno[1,2-d]-1,3-dioxin,4, 4a,5,9b-tetrahydro- Indofloro® 0.00557000 2H-Pyran-4-ol, tetrahydro-4-methyl-2-(2- 63500-71-0 Florosa Q 0.00557000 methylpropyl)-

26 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 65405-84-7 Cyclohexanebutanal, α,2,6,6-tetramethyl- Cetonal® 0.00533000 10339-55-6 1,6-Nonadien-3-ol, 3,7-dimethyl- Ethyl linalool 0.00520000 3-Buten-2-one, 4-(2,2,6-trimethyl-7- 23267-57-4 Ionone Epoxide Beta 0.00520000 10 oxabicyclo[4.1.0] hept-1-yl)- 97-54-1 Phenol, 2-methoxy-4-(1-propen-1-yl)- Isoeugenol 0.00519000 67663-01-8 2(3H)-Furanone, 5-hexyldihydro-4-methyl- Peacholide 0.00512000 Bicyclo[3.1.1]hept-2-ene-2-propanal, α,α,6,6- 15 33885-52-8 Pinyl Iso Butyrate Alpha 0.00512000 tetramethyl- 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3- 23696-85-7 Damascenone 0.00503000 cyclohexadien-1-yl)- 80-71-7 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- Maple Lactone 0.00484000 20 Propanoic acid, 2,2-dimethyl-, 2-phenylethyl 67662-96-8 Pivarose Q 0.00484000 ester 2437-25-4 Dodecanenitrile Clonal 0.00480000

25 141-14-0 6-Octen-1-ol, 3,7-dimethyl-, 1-propanoate Citronellyl Propionate 0.00469000 55066-49-4 Benzenepentanal, β-methyl- Mefranal 0.00455000 7493-74-5 Acetic acid, 2-phenoxy-, 2-propen-1-yl ester Allyl Phenoxy Acetate 0.00454000 Benzenepropanal, 4-(1,1-dimethylethyl)-a- 80-54-6 Lilial® 0.00444000 30 methyl- 4,7-Methano-1H-indene-2-carboxaldehyde, 86803-90-9 Scentenal® 0.00439000 octahydro-5-methoxy- Pentitol, 1,5-anhydro-2,4-dideoxy-2-pentyl-, 3- 18871-14-2 Jasmal 0.00434000 35 acetate 58567-11-6 Cyclododecane, (ethoxymethoxy)- Boisambren Forte 0.00433000 Naphth[2,3-b] oxirene, 1a,2,3,4,5,6,7,7a- 94400-98-3 octahydro-1a,3,3,4,6,6-hexamethyl-, Molaxone 0.00425000 40 (1aR,4S,7aS)-rel- 3-Buten-2-one, 4-(2,5,6,6-tetramethyl-2- 79-69-6 alpha-Irone 0.00419000 cyclohexen-1-yl)- 65442-31-1 Quinoline, 6-(1-methylpropyl)- Iso Butyl Quinoline 0.00408000 45 87731-18-8 Carbonic acid, 4-cycloocten-1-yl methyl ester Violiff 0.00401000 1H-Indene-5-propanal, 2,3-dihydro-3,3- 173445-65-3 Hivernal (A-isomer) 0.00392000 dimethyl- 23911-56-0 Ethanone, 1-(3-methyl-2-benzofuranyl)- Nerolione 0.00383000 50 3-Cyclohexene-1-carboxaldehyde, 1-methyl- 52474-60-9 Precyclemone B 0.00381000 3-(4-methyl-3-penten-1-yl)- 6-Oxabicyclo[3.2.1]octane, 5-methyl-1-(2,2,3- 139539-66-5 Cassifix 0.00381000 trimethyl-3-cyclopenten-1-yl)- 55 32764-98-0 2H-Pyran-2-one, tetrahydro-6-(3-penten-1-yl)- Jasmolactone 0.00355000 78417-28-4 2,4,7-Decatrienoic acid, ethyl ester Ethyl 2,4,7-decatrienoate 0.00353000

27 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 140-26-1 Butanoic acid, 3-methyl-, 2-phenylethyl ester Beta Phenyl Ethyl Isovalerate 0.00347000 Spiro[1,4-methanonaphthalene-2(1H), 2’- 41816-03-9 oxirane], 3,4,4a,5,8,8a-hexahydro-3’,7- Rhubofix® 0.00332000 10 dimethyl- Ethanol, 2-[[(1R,2R,4R)-1,7, 7- 7070-15-7 Arbanol 0.00326000 trimethylbicyclo[2.2.1]hept-2-yl]oxy]-, rel- Phenol, 2-methoxy-4-(1-propen-1-yl)-, 1- 93-29-8 Iso Eugenol Acetate 0.00324000 15 acetate 2H-Indeno[4,5-b]furan, decahydro- 476332-65-7 Amber Xtreme Compound 1 0.00323000 2,2,6,6,7,8,8-heptamethyl- Acetic acid, 2-(cyclohexyloxy)-, 2-propen-1-yl 68901-15-5 Cyclogalbanate 0.00323000 ester 20 107-75-5 Octanal, 7-hydroxy-3,7-dimethyl- Hydroxycitronellal 0.00318000 Naphtho[2,1-b]furan, 9b-ethyldodecahydro- 217816-75-6 Grisalva 0.00305000 3a,7,7-trimethyl-

25 313973-37-4 1,6-Heptadien-3-one, 2-cyclohexyl- Pharaone 0.00298000 137-00-8 5-Thiazoleethanol, 4-methyl- Sulfurol 0.00297000 1-Penten-3-one, 1-(2,6,6-trimethyl-2- 7779-30-8 Methyl Ionone 0.00286000 cyclohexen-1-yl)- 30 3-Buten-2-one, 3-methyl-4-(2,6,6-trimethyl-2- 127-51-5 Isoraldeine Pure 0.00282000 cyclohexen-1-yl)- 1,4-Cyclohexanedicarboxylic acid, 1,4-diethyl 72903-27-6 Fructalate 0.00274000 ester 35 gamma-Undecalactone 104-67-6 2(3H)-Furanone, 5-heptyldihydro- 0.00271000 (racemic) 1205-17-0 1,3-Benzodioxole-5-propanal, α-methyl- Helional 0.00270000 4H-Inden-4-one, 1,2,3,5,6,7-hexahydro- 33704-61-9 Cashmeran 0.00269000 40 1,1,2,3,3-pentamethyl- Cyclohexanone, 4-(1-ethoxyethenyl)-3,3,5,5- 36306-87-3 Kephalis 0.00269000 tetramethyl- 97384-48-0 Benzenepropanenitrile, α-ethenyl-α-methyl- Citrowanil® B 0.00265000 45 141-13-9 9-Undecenal, 2,6,10-trimethyl- Adoxal 0.00257000 2110-18-1 Pyridine, 2-(3-phenylpropyl)- Corps Racine VS 0.00257000 Indeno[1,2-d]-1,3-dioxin,4, 4a,5,9b-tetrahydro- 27606-09-3 Magnolan 0.00251000 2,4-dimethyl- 50 Propanoic acid, 2-methyl-, 3a, 4,5,6,7,7a- 67634-20-2 Cyclabute 0.00244000 hexahydro-4,7-methano-1H-inden-5-yl ester 1-Naphthalenol, 1,2,3,4,4a,7, 8,8a-octahydro- 65405-72-3 Oxyoctaline Formate 0.00236000 2,4a,5,8a-tetramethyl-, 1-formate 55 103694-68-4 Benzenepropanol, β,β,3-trimethyl- Majantol 0.00224000

28 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 2-Cyclohexen-1-one, 4-(2-buten-1-ylidene)- 13215-88-8 Tabanone Coeur 0.00223000 3,5,5-trimethyl- 25152-85-6 3-Hexen-1-ol, 1-benzoate, (3Z)- Cis-3-Hexenyl Benzoate 0.00203000 10 121-33-5 Benzaldehyde, 4-hydroxy-3-methoxy- Vanillin 0.00194000 1H-3a,7-Methanoazulen-6-ol, octahydro- 77-54-3 3,6,8,8-tetramethyl-, 6-acetate, (3R, Cedac 0.00192000 3aS,6R,7R,8aS)- 15 4,7-Methano-1H-inden-6-ol, 3a,4,5,6,7,7a- 76842-49-4 Frutene 0.00184000 hexahydro-8,8-dimethyl-, 6-propanoate 121-39-1 2-Oxiranecarboxylic acid, 3-phenyl-, ethyl ester Ethyl Phenyl Glycidate 0.00184000 4H-4a,9-Methanoazuleno[5,6-d]-1,3-dioxole, 20 211299-54-6 octahydro-2,2, 5,8,8,9a-hexamethyl-, (4aR, Ambrocenide 0.00182000 5R,7aS,9R)- Dimethyl benzyl carbinyl 10094-34-5 Butanoic acid, 1,1-dimethyl-2-phenylethyl ester 0.00168000 butyrate

25 Cyclododeca[c]furan, 1,3,3a, 40785-62-4 Muscogene 0.00163000 4,5,6,7,8,9,10,11,13a-dodecahydro- 75490-39-0 Benzenebutanenitrile, α,α,γ-trimethyl- Khusinil 0.00162000 55418-52-5 2-Butanone, 4-(1,3-benzodioxol-5-yl)- Dulcinyl 0.00161000 30 Benzoic acid, 4-hydroxy-3-methoxy-, methyl 3943-74-6 Carnaline 0.00157000 ester 3-Cyclopentene-1-butanol, β, 2,2,3- 72089-08-8 tetramethyl-2-Methyl-4-(2,2,3-trimethyl-3- Brahmanol 0.00154000

35 cyclopenten-1-yl)butanol 2-Butenal, 2-methyl-4-(2,6,6-trimethyl-1- 3155-71-3 Boronal 0.00147000 cyclohexen-1-yl)- 41199-20-6 2-Naphthalenol, decahydro-2, 5,5-trimethyl- Ambrinol 0.00140000

40 107-74-4 1,7-Octanediol, 3,7-dimethyl- Hydroxyol 0.00139000 91-64-5 2H-1-Benzopyran-2-one Coumarin 0.00130000 1,3-Dioxolane, 2-[6-methyl-8-(1- 68901-32-6 Glycolierral 0.00121000 methylethyl)bicyclo[2.2.2] oct-5-en-2-yl]- 45 Propanoic acid, 2,2-dimethyl-, 3a,4,5,6,7,7a- 68039-44-1 Pivacyclene 0.00119000 hexahydro-4,7-methano-1H-inden-6-yl ester Butanoic acid, (2E)-3,7-dimethyl-2,6-octadien- 106-29-6 Geranyl Butyrate 0.00116000 1-yl ester 50 5471-51-2 2-Butanone, 4-(4-hydroxyphenyl)- Raspberry ketone 0.00106000

29 EP 2 961 374 B1

(continued)

Vapor CAS Number Chemical name Common Name** Pressure (Torr 5 at 25°C)* 109-42-2 10-Undecenoic acid, butyl ester Butyl Undecylenate 0.00104000 * Vapor Pressures were acquired from Scifinder, which utilizes the ACD Software V.11.02, as described in the Test Methods Section. 1 Torr equal 133.3 Pa. 10 ** Origin: The low volatile fragrance materials may be obtained from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenteuil, France), IFF (Hazlet, New Jer- sey), Bedoukian (Danbury, Connecticut), Sigma Aldrich (St. Louis, Missouri), Millennium Speciality Chemicals (Ol- ympia Fields, Illinois), Polarone International (Jersey City, New Jersey) and Aroma & Flavor Specialities (Danbury, Connecticut). 15 [0078] It is understood by one skilled in the art that other volatile fragrance materials, not recited in Table 2, would also fall within the scope of the present invention, so long as they have a vapor pressure of ≥ 0.133 Pa (0.001 Torr) at 25°C.

Modulators & Co-Modulators 20 [0079] In one aspect, compositions of the present invention comprise at least one non-odorous modulator formed from an alkoxylated glucoside, selected from the group consisting of methyl glucoside polyol, ethyl glucoside polyol and propyl glucoside polyol, preferably PPG-10 Methyl Glucose Ether, PPG-20 Methyl Glucose Ether, Ethoxylated Methyl Glucose Ether, Caprylyl/Capryl Glucoside, Undecyl Glucoside, or combinations thereof. 25 [0080] Preferably, the modulator is Undecyl Glucoside and is available under the tradename Simulsol ® SL 11 W from SEPPIC, France. [0081] In another embodiment of formula (I), the modulator is a compound of formula (Ia):

[0082] In an embodiment of formula (Ia), wherein w + x + y + z is equal to 4 to 40, preferably 8 to 36, more preferably 10 to 32, more preferably 10 to 28, or combinations thereof. Preferably, the modulator is a PPG-10 Methyl Glucose Ether available under the tradename Glucam™ P-10 or Ethoxylated Methyl Glucose Ether and is available under the tradename 45 Glucam™ E-20, respectively, from Lubrizol (USA). More preferably, the modulator is a PPG-20 Methyl Glucose Ether, and is available under the tradename Glucam™ P-20 from Lubrizol (USA). [0083] In an embodiment, the modulator is a compound of formula (II):

30 EP 2 961 374 B1

wherein:

R10 is hydrogen, alkyl, alkenyl or alkynyl; 15 each R11 is independently selected from hydrogen, alkyl, alkenyl, alkynyl; each R12 is independently selected from hydrogen, alkyl, alkenyl, or alkynyl; each R13 is independently selected from hydrogen, alkyl, alkenyl, or alkynyl; each R14 is selected from alkylene, alkenylene, or alkynylene; and R15 is hydrogen, alkyl, alkenyl or alkynyl; 20 wherein t is 5 or less, preferably 1, 2 or 3.

[0084] Preferably, the modulator of formula (II) is Caprylyl/Capryl Glucoside and is available under the tradename Plantacare® 810 UP from BASF, Ludwigshafen, Germany. [0085] The inventors discovered that the alkoxylated glucoside acts as a modulator of the perceived intensity and/or 25 longevity of the fragrance profile of the composition of the present invention when low levels of the low volatile fragrance materials are used. For example, the modulators act to prolong the duration during which the fragrance profile can be perceived as compared to a control composition in the absence of the modulators. As another example, the modulators can improve the intensity of the fragrance profile such that it remains significantly the same from initial impression to the end as compared to a control composition. 30 [0086] While not wishing to be bound by theory, it is believed that the modulators associate to the fragrance materials and retard evaporation. [0087] In another aspect, compositions of the present invention further comprise one or more non-odorous fragrance co-modulators. The fragrance co-modulators consist of substances capable of increasing the intensity and/or longevity of the fragrance profile, and therefore of the composition, as compared to control composition absent the co-modulators. 35 In one embodiment, the non-odorous fragrance co-modulators are selected from the group consisting of:

[0088] PPG-3 myristyl ether is commercialized by various suppliers including:

(i) Evonik-Goldschmidt under the tradename Tegosoft™ APM; 45 (ii) Degussa under the tradename Varonic® APM; (iii) International Speciality Products as a mixture of PPG-3 myristyl ether with isocetyl alcohol; (iv) Lubrizol Advanced Materials (USA) as a mixture of PPG-3 myristyl ether with neopentyl glycol diethylhexanoate under the tradename Schercemol™ NGDO ester; and (v) combinations thereof. 50 [0089] However, any such commercial forms of PPG-3 myristyl ether and mixtures thereof, are appropriate for use as co-modulators in the compositions of the present invention. [0090] The composition comprises the non-odorous fragrance co-modulators present in an amount of from about 0.05 wt% to about 10 wt%, preferably from about 0.5 wt% to about 6 wt%, or combinations thereof, relative to the total weight 55 of the composition. Alternatively, the non-odorous fragrance co-modulators is present in an amount of from about 0.05 wt% or 0.5 wt% to about 6 wt% or 10 wt%, relative to the total weight of the composition. Preferably, the non-odorous fragrance co-modulator exist as mixtures of PPG-3 myristyl ether together with CERAPHYL® ICA and Schercemol™ NGDO ester, wherein the PPG-3 myristyl ether is 50 wt% and the other two components thereof are present in equal

31 EP 2 961 374 B1

wt% in the mixture, wherein the wt% is the total weight of all the co-modulators in the composition. In particular, mixtures of PPG-3 myristyl ether with CERAPHYL ® ICA, in a 1:1 weight ratio, is preferred (PCT Publication No. WO2013/064412 (Firmenich)). [0091] In another embodiment, the co-modulators exist as mixtures of Neopentyl Glycol Diethylhexanoate together 5 with CERAPHYL® ICA, wherein the Neopentyl Glycol Diethylhexanoate is 50 wt% and CERAPHYL® ICA is 50 wt% in the compositions are useful. Similarly, compositions of the present invention that contain at least 50 wt% of Schercemol™ NGDO ester together with Tegosoft™ APM also proved to be useful to prolong the perception of the fragrance profile from the substrate on which it has been applied, as compared to control compositions (PCT Publication No. WO2013/060691 (Firmenich)). 10 [0092] It is understood that the addition of the co-modulators is intended to further improve the intensity and/or longevity of the fragrance profile of the composition above the improvement already provided for by the modulators. Preferably, at least 50 wt% of the non-odorous fragrance modulator is PPG-20 Methyl Glucose Ether, with the remainder to 100 wt% possibly being one or more other modulators or co-modulators. [0093] In yet another aspect, compositions of the present invention comprises one or more non-odorous fragrance 15 co-modulators selected from the group consisting of:

(v) Isocetyl alcohol (CERAPHYL® ICA); (vi) PPG-3 myristyl ether (preferably Tegosoft™ APM and/or Varonic ® APM); (vii) Neopentyl glycol diethylhexanoate (preferably Schercemol™ NGDO); and 20 (viii) mixture thereof preferably with isocetyl alcohol (CERAPHYL ® ICA).

and being essentially free of non-odorous modulators formed from an alkoxylated glucoside selected from the group consisting of methyl glucoside polyol, ethyl glucoside polyol and propyl glucoside polyol. As used herein, the term "essentially free" means that the composition is free of that ingredient or no ingredient is intended to be added to the 25 composition. [0094] In an embodiment, a composition comprising:

(i) a fragrance component present in an amount of from about 0.04 wt% to about 30 wt%, preferably 1 wt% to about 30 wt%, preferably less than about 25 wt%, preferably less than about 20 wt%, preferably less than about 15 wt%, 30 preferably less than about 10 wt% or preferably less than 8 wt%, relative to the total weight of the composition; and wherein:

(a) the fragrance component comprises at least one low volatile fragrance material having a vapor pressure < 0.001 Torr at 25°C; and 35 (b) the low volatile fragrance material is present in an amount of from about 0.1 wt% to about 30 wt%, preferably less than about 28 wt%, preferably less than about 25 wt%, preferably less than about 22 wt%, preferably less than 20 wt%, preferably less than 18 wt%, or preferably less than 15 wt%, relative to the total weight of the fragrance component;

40 (ii) one or more non-odorous fragrance co-modulators selected from the group consisting of:

(a) Isocetyl alcohol (CERAPHYL® ICA); (b) PPG-3 myristyl ether (preferably Tegosoft™ APM and/or Varonic ® APM); (c) Neopentyl glycol diethylhexanoate (preferably Schercemol™ NGDO); and 45 (d) mixture thereof preferably with isocetyl alcohol (CERAPHYL ® ICA);

wherein the co-modulators are present in an amount of from about 0.05 wt% or 0.5 wt% to about 6 wt% or 10 wt%, relative to the total weight of the composition

50 TEST METHODS

[0095] The following assays set forth must be used in order that the invention described and claimed herein may be more fully understood.

55 Test Method 1: Determining Vapor Pressure

[0096] In order to determine the vapor pressure for the fragrance materials, go to the websitehttps:// scifinder.cas.org/scifinder/view/scifinder/scifinderExplore.jsf and follow these steps to acquire the vapor pressure.

32 EP 2 961 374 B1

1. Input the CAS registry number for the particular fragrance material. 2. Select the vapor pressure from the search results. 3. Record the vapor pressure (given in Torr at 25°C).

5 [0097] SciFinder uses Advanced Chemistry Development (ACD/Labs) Software Version 11.02. (© 1994-2013). If the CAS number for the particular fragrance material is unknown or does not exist, you can utilize the ACD/Labs reference program to directly determine the vapor pressure.

Test Method 2: Olfactory Tests 10 [0098] In order to show the effect of the modulators/co-modulators and low volatile fragrance materials on the perception of fragrance profile in a composition of the present invention, test compositions are made, as described in the Example section, and given to panelists to evaluate. [0099] At the testing facility, 50 mL samples of the compositions or the controls are applied to glass slides and placed 15 on a hot plate at 32°C to represent skin temperature for varying durations. The panelists are asked to evaluate the perceived fragrance profile (intensity and/or character) from each pair of samples,i.e., that of the test composition of the present invention vs. the corresponding control, at time 0 and later time points (1, 2, 3 4 and 6 hours post application) as the fragrance profile evolves. Their assessments are recorded. Panelists are selected from individuals who are either trained to evaluate fragrances according to the scales below or who have experience of fragrance evaluation in the 20 industry.

(a) Fragrance Intensity:

[0100] The panelists are asked to give a score on a scale of 1 to 5 for perceived fragrance intensity according to the 25 odour intensity scale set out in Table 3 herein below.

Table 3 - Odour Intensity Scale Score Fragrance Intensity

30 1 Very Poor 2 Poor 3 Good 4 Very Good 35 5 Excellent

(b) Fragrance Character:

40 [0101] The panelists are asked to assess the fragrance character in one of 2 ways:

i) a score on a scale of 0 to 3 for the dominance of particular characters that are relevant to that particular fragrance, e.g.: floral, rose, muguet, fruity, apple, berry, citrus, woody, musk just to name a few, according to the odour grading scale set out in Table 4i herein below; 45 ii) a score on a scale of 1 to 5 for changes in the perceived fragrance character change for the test compositions versus the controls according to the odour grading scale set out in Table 4ii herein below.

Table 4i - Character Dominance Odour Grading scale 50 Score Fragrance Character Dominance 0 Not noticeable 1 Slight presence of the character

55 2 Moderate presence of the character 3 Dominance of the character

33 EP 2 961 374 B1

Table 4ii - Character Difference Odour Grading Scale Score Fragrance Character Change

5 1 Perfume character is unchanged, i.e., no difference between the sample vs. the control. 2 Slight perfume character change when compared directly with the control. 3 Moderate perfume change but similar character to the control, 4 Large difference in perfume character from the control. 10 5 Total difference in the perfume character from the control.

[0102] The results of the panelists are averaged and then analysed using Analysis of Variance methods. The model treats the subject as a random effect and looks at the impact of product, time and the interaction between product and 15 time. From the analysis the least square means for the product and time interaction are obtained. These means (as well as their confidence intervals) are then plotted to enable comparisons between products at each time point. It should be noted that the confidence levels plotted are intended as a guide, and not as a statistical comparison, as they do not take into account that multiple testing has been performed. As well as a graphical assessment, statistical comparisons between the two products at each of the time points are performed with a Sidak correction for multiple comparisons. The p-values 20 for the product differences were obtained, with p-values < 0.05 indicating a statistical difference between the two products at 5% significance (or 95% confidence).

EXAMPLES

25 [0103] The following examples are provided to further illustrate the present invention and are not to be construed as limitations of the present invention, as many variations of the present invention are possible without departing from its scope. In the following 1 Torr equals 133.3 Pa. 5

Examples 1 to 6 - Fragrances 30 [0104] Examples 1a to 5 are non-limiting examples of formulations of fragrance materials intended to form the fragrance component of the compositions of the present invention. The exemplary formulations of the fragrance materials span the range from "simple accords" (<10 fragrance materials) to "complex fragrances" (> 30 fragrance materials). Typically, full bodied fragrance compositions do not comprise less than about 30 fragrance materials. Examples 1b and 6 are 35 examples of a formulation of fragrance materials intended to form the fragrance component that fall outside the scope of the present invention. The following fragrance formulations are made by mixing the listed ingredients in the listed proportions (wt%) at room temperature, wherein the wt% is relative to the total weight of the fragrance component.

Table 5a - Example 1a - Fresh Floral Accord (Fragrance I - 8.00 wt% Low Volatile Fragrance Materials) 40 Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) Benzyl acetate 140-11-4 0.1640 11.0 Linalool 78-70-6 0.0905 10.0

45 Phenethyl alcohol 60-12-8 0.0741 16.0 Indole 120-72-9 0.0298 1.0 α-Terpineol 98-55-5 0.0283 3.0 Geranyl acetate 105-87-3 0.0256 5.0 50 Cymal 103-95-7 0.00881 6.0 Hydroxycitronellal 107-75-5 0.00318 23.0 Majantol 103694-68-4 0.00224 17.0

55 Hexyl cinnamic aldehyde 101-86-0 0.000697 8.0

34 EP 2 961 374 B1

Table 5b - Example 1b - Traditional Floral Accord (Fragrance VII - 54.00 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%)

5 Benzyl acetate 140-11-4 0.1640 5.5 Linalool 78-70-6 0.0905 5.0 Phenethyl alcohol 60-12-8 0.0741 8.0 Indole 120-72-9 0.0298 0.5 10 α-Terpineol 98-55-5 0.0283 1.5 Geranyl acetate 105-87-3 0.0256 2.5 Cymal 103-95-7 0.00881 3.0

15 Hydroxycitronellal 107-75-5 0.00318 11.5 Majantol 103694-68-4 0.00224 8.5 Hexyl cinnamic aldehyde 101-86-0 0.000697 4.0 iso gamma super 68155-66-8 0.000565 12.50 20 Sandalore 65113-99-7 0.000625 18.75 Habanolide 111879-80-2 0.00000431 18.75

25 Table 6 - Example 2 - Floral Gourmand Accord (Fragrance II - 0.20 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) Manzanate 39255-32-8 2.910000 1.0

30 Hexyl acetate 142-92-7 1.390000 4.0 Verdox™ 88-41-5 0.103000 10.0 Phenethyl alcohol 60-12-8 0.074100 16.0 Cymal 103-95-7 0.008810 4.0 35 Ethylmethylphenylg lycidate 77-83-8 0.005710 7.5 Hydroxycitronellal 107-75-5 0.003180 24.0 Methyl Ionone 7779-30-8 0.002860 22.5

40 Gamma-Undecalactone (Ald C14) 104-67-6 0.002710 9.0 Methyl laitone* 94201-19-1 0.000697 0.2 Triethyl citrate (TEC) 77-93-0 -- 1.8 * Supplied at 10% in TEC. 45

Table 7 - Example 3 - Woody Accord (Fragrance III - 7.00 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) 50 Vertenex 32210-23-4 0.103000 7.0 Koavone 81786-73-4 0.027500 40.0 Cedryl methyl ether 19870-74-7 0.012800 5.0

55 Synambran 6790-58-5 0.009340 2.0 Methyl Ionone 7779-30-8 0.002860 6.0 Kephalis 36306-87-3 0.002690 20.0

35 EP 2 961 374 B1

(continued)

Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) Cashmeran 33704-61-9 0.002690 2.0 5 Ambrocenide 211299-54-6 0.001820 3.0 Brahmanol 72089-08-8 0.001540 8.0 Sandalore® 65113-99-7 0.000625 7.0

Table 8 - Example 4 - Fresh Male Accord (Fragrance IV - 13.51 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%)

15 d-Limonene 5989-27-5 1.540000 10.0 Dihydromyrcenol 18479-58-8 0.166000 10.0 Boisiris 68845-00-1 0.013500 6.5 Canthoxal 5462-06-6 0.010200 8.0 20 Helional 1205-17-0 0.002700 10.0 Kephalis 36306-87-3 0.002690 20.0 Majantol 103694-68-4 0.002240 15.5

25 Javanol® 198404-98-7 0.000902 5.0 Galaxolide* 1222-05-5 0.000414 7.5 Isopropyl Myristate 110-27-0 -- 7.5 * Supplied at 50% in Isopropyl myristate. 30

Table 9 - Example 5 - Sweet Dream 18 Fragrance (Fragrance V - 11.15 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) 35 Prenyl acetate 1191-16-8 3.99000000 0.100 Manzanate 39255-32-8 2.91000000 0.200 Hexyl acetate 142-92-7 1.39000000 0.700

40 cis-3-Hexenyl acetate 3681-71-8 1.22000000 0.200 Benzaldehyde 100-52-7 0.97400000 0.200 Liffarome 67633-96-9 0.72100000 0.150 Hexyl isobutyrate 2349-07-7 0.41300000 0.055 45 Dihydromyrcenol 18479-58-8 0.16600000 2.500 Benzyl acetate 140-11-4 0.16400000 0.700 Linalyl acetate 115-95-7 0.11600000 2.500

50 Verdox 88-41-5 0.10300000 4.000 Phenethyl alcohol 60-12-8 0.07410000 8.000 Rossitol 215231-33-7 0.02990000 1.500 alpha-Terpineol 98-55-5 0.02830000 1.500 55 Geranyl acetate 105-87-3 0.02560000 1.500 Rhodinol 141-25-3 0.01970000 0.700

36 EP 2 961 374 B1

(continued)

Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) Givescone 57934-97-1 0.01710000 0.700 5 Methyl anthranilate 134-20-3 0.01580000 0.050 Ysamber K 154171-77-4 0.01470000 1.000 alpha-Ionone 127-41-3 0.01440000 3.000 10 Citronellyl acetate 150-84-5 0.01370000 0.500 cis-3-hexenyl-cis-3-hexenoate 61444-38-0 0.01220000 0.200 Cinnamic alcohol 104-54-1 0.01170000 0.100 delta-damascone 57378-68-4 0.01020000 0.200 15 Citronellyloxyacetal dehyde 7492-67-3 0.00967000 0.100 Cymal 103-95-7 0.00881000 0.500 Floralozone 67634-15-5 0.00808000 0.100 20 Ethylmethylphenylg lycidate 77-83-8 0.00571000 0.200 Florosa Q 63500-71-0 0.00557000 3.000 Ethyl linalool 10339-55-6 0.00520000 6.400 Pivarose 67662-96-8 0.00484000 2.500 25 Hydroxycitronellal 107-75-5 0.00318000 7.500 Methyl Ionone 7779-30-8 0.00286000 4.000 gamma-Undecalactone 104-67-6 0.00271000 0.500 30 Kephalis 36306-87-3 0.00269000 5.000 Cashmeran 33704-61-9 0.00269000 1.000 Magnolan 27606-09-3 0.00251000 3.000

35 Majantol 103694-68-4 0.00224000 6.900 Brahmanol 72089-08-8 0.00154000 3.000 Coumarin 91-64-5 0.00130000 0.500 Glycolierral 68901-32-6 0.00121000 0.100 40 Raspberry ketone 5471-51-2 0.00106000 0.100 Top Mango base3 -- -- 0.500 Cherry base3 -- -- 0.200 3 45 Cassis base -- -- 0.300 Bergamot Oil4 -- -- 6.000 Prunella base3 -- -- 0.500 Hexyl cinnamic aldehyde 101-86-0 0.00069700 1.500 50 Sandalore 65113-99-7 0.00062500 3.000 Dupical 30168-23-1 0.00044100 0.005 Galaxolide1 1222-05-5 0.00041400 1.500

55 Ebanol 67801-20-1 0.00028100 2.000 Helvetolide 141773-73-1 0.00005790 2.000 Warm Milk base5 -- -- 0.200

37 EP 2 961 374 B1

(continued)

Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) Vanilla Absolute2,6 -- -- 0.100 5 Isopropyl Myristate -- -- 1.500 Dipropylene Glycol -- -- 6.040 Total 100.00 10 1 supplied at 50% in IPM. 2 Supplied at 50% in DiPG. 3 Proprietary bases that contain a mixture of perfume raw materials, judged to be of high volatility for the purposes of calculating % of low volatility PRMs. 4 Natural oils or extracts that contain a mixture of perfume raw materials, judged to be of high volatility for the purposes 15 of calculating % of low volatility PRMs. 5 Proprietary bases that contain a mixture of perfume raw materials, judged to be of low volatility for the purposes of calculating % of low volatility PRMs. 6 Natural oils or extracts that contain a mixture of perfume raw materials, judged to be of low volatility for the purposes of calculating % of low volatility PRMs. 20

Table 10 - Example 6 - Fresh Floral GF 6-7 Accord (Fragrance VI - 40.14 wt% Low Volatile Fragrance Materials) Ingredients CAS Number Vapor Pressure (Torr at 25°C) Parts (wt%) 25 Ligustral or Triplal 68039-49-6 0.578000 0.15 Benzyl acetate 140-11-4 0.164000 0.31 Verdox 88-41-5 0.103000 5.38 Phenethyl alcohol 60-12-8 0.074100 1.54 30 Indole 120-72-9 0.029800 0.02 Heliotropin 120-57-0 0.010400 1.23 gamma-Decalactone 706-14-9 0.008520 0.38 35 Florol 63500-71-0 0.005570 15.38 Ethyl linalool 10339-55-6 0.005200 26.15 Isoeugenol 97-54-1 0.005190 0.08

40 alpha-Irone 79-69-6 0.004190 1.54 Vanillin 121-33-5 0.001940 6.15 Dimethyl benzyl carbinyl butyrate 10094-34-5 0.001680 1.54 Methyl beta-naphthyl ketone 93-08-3 0.000957 0.77 45 Methyl dihydrojasmonate 24851-98-7 0.000710 30.60 Benzyl salicylate 118-58-1 0.000175 7.69 Polysantol 107898-54-4 0.000117 0.77

50 Lrg 201 4707-47-5 0.000029 0.31

Examples 7 - Compositions Comprising Fragrance Modulators

[0105] Compositions A, C, E, G, and L are examples of fine fragrance compositions according to the present invention, 55 made with Fragrances I to V, respectively. They are prepared by admixture of the components described in Tables 11a, in the proportions indicated. In parallel, control Compositions B, D, F, H, and M, are prepared by replacing the non- odorous fragrance modulator, Glucam™ P-20, by the same amount of demineralized water. Additionally, Compositions

38 EP 2 961 374 B1

I and N are examples of a fine fragrance composition comprising excessive levels of low volatile fragrance materials, and Compositions J and O are their corresponding controls, minus the non-odorous fragrance modulator, Glucam™ P- 20. Composition K is an example of a fine fragrance composition of the present invention with both modulator and co- modulator. 5

39 EP 2 961 374 B1

20 1 75.0 to 100 to 25 Composition (wt%) Composition

35 Table 11a - Fine Fragrance Compositions Fragrance Fine - 11a Table

40 BDFHIABCDEFGH JKLMNO ------7.07.0------8.08.0 ------8.45 8.45 ------7.07.0------7.0 7.0 ------7.0 7.0 ------7.07.0------7.0------15.0 -- 15.0 -- 15.0 -- 15.0 -- 15.0 -- 7.5 15.0 -- 15.0 --

50 Wt% is relative to the total weight of the composition. the of weight total the to relative is Wt% Ingredients 1 Fragrance V VII IV Fragrance Fragrance VI Fragrance Fragrance Fragrance I III Fragrance Fragrance Ethanol Fragrance II Fragrance Glucam™P-20 Isocetyl alcohol CERAPHYL ICA------7.5------CERAPHYL alcohol Isocetyl water Demineralized 55

40 EP 2 961 374 B1

[0106] Compositions AA, BB, CC, DD, EE, FF, HH, II, and JJ are examples of fine fragrance compositions according to the present invention, made with Fragrances I, II and V the non-odorous fragrance modulators: Glucam™ P-10, Glucam™ E-10, and Glucam™ E-20, respectively. They are prepared by admixture of the components in Table 11b, in the proportions indicated. In parallel, Compositions GG and KK, are prepared by incorporating a non-odorous fragrance 5 modulator and a co-modulator (Glucam™ P-10and Isocetyl alcohol CERAPHYL ICA) or two non-odorous fragrance modulators (Glucam™ P-10, Glucam™ P-20), respectively.

Table 11b - Fine Fragrance Compositions Composition (wt%)1 10 Ingredients AA BB CC DD EE FF GG HH II JJ KK Fragrance I 7.0 7.0 7.0 ------7.0 ------7.0 Fragrance II ------7.0 7.0 7.0 ------15 Fragrance V ------7.0 7.0 7.0 -- Ethanol 75.0 Glucam™ P-20 ------7.5 Glucam™ P-10 15 -- -- 15 -- -- 7.5 15 -- -- 7.5 20 Glucam™ E-10 -- 15 -- -- 15 ------15 -- -- Glucam™ E-20 -- -- 15 -- -- 15 ------15 -- Isocetyl alcohol CERAPHYL ICA ------7.5 ------25 Demineralized water to 100

[0107] Compositions b and d are examples of compositions according to the present invention, made with single perfume raw materials and the non-odorous modulators Simulsol SL 11W™ and Plantacare® 810 UP, respectively. 30 They are prepared by admixture of the components in Table 11c, in the proportions indicated. In parallel, control Com- positions a and c are prepared without a non-odorous modulator as a control.

Table 11c - Single Pefume Raw Material Compositions Composition (wt%)1 35 Ingredients abcd Phenethyl alcohol 1.0 1.0 - - Cymal - - 1.0 1.0

40 Simulsol SL11W™2 -2.7- - Plantacare® 810 UP3 ---2.5 Ethanol 75 Demineralized water to 100 45 1 Wt% is relative to the total weight of the composition. 2 Added as a 55 wt% active solution in water. 3 Added as a 62 wt% active solution in water.

50 [0108] Compositions P and Q are examples of body spray compositions according to the present invention. They are prepared by admixture of the components described in Table 12, in the proportions indicated.

Table 12 - Body Spray Compositions Compositions (wt%1) 55 Ingredients CAS Number PQPPQQ Denatured Ethanol 64-17-5 39.70 59.45 39.70 39.70

41 EP 2 961 374 B1

(continued)

Compositions (wt%1) Ingredients CAS Number PQPPQQ 5 Water 7732-18-5 - 0.75 -- -- Dipropylene Glycol 25265-71-8 15.00 -- 15.00 15.00 Isopropyl Myristate 110-27-0 1.00 -- 1.00 1.00 10 Zinc Phenosulphonate 127-82-2 0.50 -- 0.50 0.50 Cavasol® W7 methylated Beta-cyclodextrin 128446-36-6 -- 1.00 -- -- Fragrance2 -- 1.20 1.20 1.20 1.20 Glucam™ P-20 61849-72-7 2.60 2.60 -- -- 15 Glucam™ P-10 61849-72-7 -- -- 2.60 -- Glucam™ E-20 68239-42-9 ------2.60 Propane 74-98-6 4.86 -- 4.86 4.86 20 Isobutane 72-28-5 27.14 -- 27.14 27.14 1,1-Difluoroethane (HFC-152a) 75-37-6 8.00 35.00 8.00 8.00 1 wt% relative to the total weight of the composition. 2 Can be any Fragrances I, II, or V. 25

[0109] Composition R is an example of body lotion composition according to the present invention. It is prepared by admixture of the components described in Table 13, in the proportions indicated.

Table 13 - Body Lotion Composition 30 Compositions (wt%1) Ingredients CAS Number RST Water 7732-18-5 qsp 100 % qsp 100 % qsp 100 % 35 Trilon® B 64-02-8 0.05 0.05 0.05 Carbopol® ETD 2050 9003-01-4 0.2 0.2 0.2 Pemulen™ TR1 9063-87-0 0.2 0.2 0.2 Nexbase® 2008 68037-01-4 8 8 8 40 Silicone V100 63148-62-9 6 6 6 Glucam™ P-20 61849-72-7 3 -- -- Glucam™ P-10 61849-72-7 -- 3 -- 45 Glucam™ E-20 68239-42-9 -- -- 3 Tris Amino™ Ultra Pur 102-71-6 0.4 0.4 0.4 Fragrance2 -- 3 3 3 Preservatives -- qs qs qs 50 1 wt% relative to the total weight of the composition. 2 Can be any Fragrances I, II, or V.

Example 8 - Odour Test 55

[0110] Compositions disclosed in Table 11a are applied to glass slides in accordance with the protocol described in the Method Section and a panel of 9 expert panelists evaluated the perceived fragrance profile at intial time 0, then at

42 EP 2 961 374 B1

various time points typically 1 hour, 2 hours, 3 hours, 4 hours and 6 hours post application.

(a) Compositions A vs. B:

5 Panellists are asked to score the compositions for the intensity of the fragrance on a scale of 1 to 5, wherein 1 represents a low fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. The results of the panel test are then averaged. Figure 1 shows the effect of the fragrance modulator and reduced levels of low volatile fragrance materials for compositions A and B on fragrance intensity. Fragrance intensity is maintained for up to 6 hours in the presence of the modulator whilst it drops in the absence of the 10 modulator. The modulator acts to maintain the continued evaporation over time of the perfume materials. The effect of the improved fragrance strength of the present invention is noticeable at 3 hours and 6 hours with an indication of a statistical difference at 6 hours after application on the slides as indicated graphically by the confidence intervals. Statistical analysis using the Sidak corrections for multiple comparisons confirm the sta- tisticallysignificant difference between the 2 productsat 6 hours at 5% significancelevel (p= 0.0008, i.e.,p < 0.05). 15 Panellists are are also asked to score the composition for the dominance of the muguet character on a scale of 0 to 3 wherein 0 represents not detectable and 3 represents it being the dominant character. The results of the panel test are then averaged. Figure 2 shows the effect of the fragrance modulator and reduced levels of low volatile fragrance materials for compositions A and B on muguet character dominance. The muguet character is reduced by the modulator at the initial time point but is then released over the remainder of the time for up 20 to at least 6 hours. The effect of the improved fragrance character over time of the compositions of the present invention are noticeable at 3 and 6 hours with an indication of a statistical difference at 6 hours after application on the slides as indicated by the confidence intervals. Statistical analysis using both the Sidak corrections for multiple comparisons confirm the statistically significant difference between the 2 products at 0 and 6 hours at 5% significance level (p = 0.0261 respectively, i.e., p < 0.05). 25 (b) Compositions C vs. D:

Panellists are asked to score the compositions for the intensity of the fragrance on a scale of 1 to 5, wherein 1 represents a low fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. 30 The results of the panel test are then averaged. Figure 3 shows the effect of the fragrance modulator and reduced levels of low volatile fragrance materials for compositions C and D on fragrance intensity. Fragrance intensity is maintained for up to 6 hours in the presence of the modulator whilst it drops in the absence of the modulator. The modulator acts to maintain the continued evaporation over time of the perfume materials. The effect of the improved fragrance strength of the present invention is noticeable at 2 and 4 hours and significant 35 at 6 hours after application on the slides as indicated graphically by the confidence intervals. Statistical analysis using the Sidak corrections for multiple comparisons confirm the statistically significant difference between the 2 products at 4 hours at 5% significance level (p=0.035, i.e., p < 0.05) and at 6 hours at 5% significance level (p = < 0.0001, i.e., p < 0.05). Panellists are asked to score the compositions on a scale of 1 to 5, wherein 1 represents the perfume character 40 remains unchanged and 5 represents a total change in the perfume character. The results of the panel test were averaged and plotted together with the confidence intervals. Figure 4 shows the effect of the fragrance modulator and reduced levels of low volatile fragrance materials for compositions C and D. The presence of the modulator results in noticeable changes in perfume character. Statistical analysis using the Sidak corrections for multiple comparisons confirm the statistically significant difference between the 2 products at 1 hour (p = 45 0.002, i.e., p < 0.05), 4 hours (p = 0.0003, i.e., p < 0.05) and 6 hours (p = < 0.001, i.e., p < 0.05) at 5% significance level. Similar effects are observed for compositions E to H, and L to M (data not shown).

(c) Compositions N and O 50 Panellists are asked to score the compositions for the intensity of the fragrance on a scale of 1 to 5, wherein 1 represents a low fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. The results of the panel test are then averaged. Figure 5 shows the effect of the fragrance modulator and excessive levels of low volatile fragrance materials for compositions N and O on fragrance intensity. Fragrance intensity is unaffected by the addition of the modulator. There are no statistical differences between the 2 products. 55 Panellists are also asked to score the composition for the dominance of the muguet character on a scale of 0 to 3 wherein 0 represents not detectable and 3 represents it being the dominant character. The results of the panel test are then averaged. Figure 6 shows the effect of the fragrance modulator and excessive levels of low volatile fragrance materials for compositions N and O on muguet character dominance. The muguet character is perceived initially

43 EP 2 961 374 B1

but then drops quickly over time. After 1 hour it is only slightly perceived and after 6 hours it is not present in either composition. Addition of the modulator does not result in prolonged release of the muguet character as was seen in compositions A and B. There are no statistical differences between the 2 products. (d) Compositions I and J 5 Panellists are asked to score the compositions for the intensity of the fragrance on a scale of 1 to 5, wherein 1 represents a low fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. The results of the panel test are then averaged. Figure 7 shows the effect of the fragrance modulator in the presence of execessive levels of low volatile fragrance materials for compositions I and J. The effects of the modulator is negated in more traditional fragrance composition where execessive amounts of the low volatile fragrance materials are 10 present. The fragrance appears to be suppressed with a loss of strength. This is noticeable at all time points and appears significant as indicated graphically by the confidence intervals. Statistical analysis using the Sidak corrections for multiple comparisons confirm the statistically significant difference between the 2 products at time 0 (p = 0.0229, i.e., p < 0.05), at 1 hour (p = 0.0013, i.e., p < 0.05), at 3 hours (p = 0.0013, i.e., p < 0.05) and at 6 hours (p = 0.0003, i.e., p < 0.05) at 5% significance level. 15 [0111] Compositions disclosed in Table 11c are applied to glass slides in accordance with the protocol described in the Method Section and a panel of 8 expert panelists evaluated the perceived fragrance profile at intial time 0, then at various time points typically 1 hour, 3 hours, 5 hours and 6 hours post application.

20 (e) Compositions a vs. b:

(f) Compositions c vs. d:

Panellists are asked to score the compositions for the intensity of the fragrance on a scale of 1 to 5, wherein 1 35 represents a low fragrance intensity is detected and 5 represents a very strong fragrance intensity is detected. The results of the panel test are then averaged. Figure 9 shows the effect of the fragrance modulator Plantacare ® 810UP on Cymal. Addition of the modulator maintains the intensity of the perfume raw material from 1 hour up to 6 hours whilst the control, in the absence of the modulator, drops over the 6 hours. The modulator acts to maintain the continued evaporation over time of the perfume material. Statistical analysis using the Tukey 40 correction for multiple comparisons confirms the statistically significant difference at 3 hours at 95% significance level (p = 0.0002, i.e., p < 0.05) and at 6 hours at 95% significance level (p 0.0022, i.e., p < 0.05).

[0112] It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum 45 numerical limitation given throughout this specification will include every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical. [0113] The citation of any document is not an admission that it is prior art with respect to any invention disclosed or claimed herein or that it alone, or in any combination with any other reference or references, teaches, suggests or 50 discloses any such invention. [0114] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention. 55

44 EP 2 961 374 B1

Claims

1. A composition comprising:

5 (i) a fragrance component present in an amount of from 1 wt% to 30 wt%, preferably less than 25 wt%, preferably less than 20 wt%, preferably less than 15 wt%, preferably less than 10 wt% or preferably less than 8 wt%, relative to the total weight of the composition; and wherein:

(a) the fragrance component comprises at least one low volatile fragrance material having a vapor pressure 10 < 0.133 Pa (0.001 Torr) at 25°C; (b) the low volatile fragrance material is present in an amount of from 0.1 wt% to 30 wt%, preferably less than 25 wt%, preferably less than 20 wt%, or preferably less than 12 wt%, relative to the total weight of the fragrance component; (c) the fragrance component further comprising one or more volatile fragrance materials having a vapor 15 pressure ≥ 0.133 Pa (0.001 Torr) at 25°C; and (d) the volatile fragrance material is present in an amount of from 70 wt% to 99.9 wt%, preferably greater than80 wt%, or most preferably greater than88%, relative to the totalweight of thefragrance component; and

(ii) at least one non-odorous fragrance modulator formed of an alkoxylated glucoside selected from the group 20 consisting of methyl glucoside polyol, ethyl glucoside polyol, propyl glucoside polyol, preferably PPG-10 Methyl Glucose Ether, PPG-20 Methyl Glucose Ether, Ethoxylated Methyl Glucose Ether, Caprylyl/Capryl Glucoside, Undecyl Glucoside, or combinations thereof, in an amount of from 0.1 wt% to 20 wt%, preferably 0.5 wt% to 18 wt%, or more preferably 2.5 wt% to 15%, relative to the total weight of the composition.

25 2. The composition of claim 1, wherein the low volatile fragrance material is selected from the group consisting of: 2- Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; Ethanone, 1-(2-naphthalenyl)-; 3-Decanone, 1-hydroxy-; Cyclopropanemethanol, 1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-; Benzaldehyde, 3- ethoxy-4-hydroxy-; 2H-1,5-Benzodioxepin-3(4H)-one, 7-methyl-; 2-Butanol, 1-[[2-(1,1-dimethylethyl)cyclohexyl]oxy]-; Spiro[5.5]undec-8-en-1-one, 2,2,7,9-tetramethyl-; Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl 30 ester, (1R,2R)-rel-; Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester; Octanal, 2-(phenylmethylene)-; Cy- clopentanecarboxylic acid, 2-hexyl-3-oxo-, methyl ester; 3-Cyclopentene-1-butanol,α ,β,2,2,3-pentamethyl-; Cy- clopentanone, 2-(3,7-dimethyl-2,6-octadien-1-yl)-; 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-; 2-Pentenenitrile, 3- methyl-5-phenyl-, (2Z)-; Benzenepropanenitrile, 4-ethyl-α,α-dimethyl-; 1H-3a,7-Methanoazulen-6-ol, octahydro- 3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-; Ethanone, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphtha- 35 lenyl)-; Propanoic acid, 2-methyl-, 4-formyl-2-methoxyphenyl ester; 1,6-Heptadien-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; Benzoic acid, 2-hydroxy-, hexyl ester; Benzoic acid, phenyl ester; Cyclohexanepropanol, 2,2,6- trimethyl-α-propyl-, (1R,6S)-; Cyclohexanepropanol, 2,2,6-trimethyl-α-propyl-; Benzoic acid, 2-hydroxy-, 3-methyl- 2-buten-1-yl ester; 2H-1,5-Benzodioxepin-3(4H)-one, 7-(1-methylethyl)-; Butanal, 4-(octahydro-4,7-methano-5H- inden-5-ylidene)-; Cyclopenta[g]-2-benzopyran, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-; Cyclopentanone, 40 2-[2-(4-methyl-3-cyclohexen-1-yl)propyl]-;2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-; 2-Propenoic acid, 3-phenyl-, pentyl ester; 4H-Pyran-4-one, 3-hydroxy-2-methyl-; 1-Pro- panol, 2-methyl-3-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy]-; 1-Naphthalenol, 1,2,3,4,4a,5,8,8a-octahydro- 2,2,6,8-tetramethyl-; 2-Butenoic acid, 2-methyl-, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester, (2E)-; 1,3-Dioxane, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-; Nonadecane; 4-Penten-2-ol, 3-methyl-5-(2, 2,3- 45 trimethyl-3-cyclopenten-1-yl)-; Propanoic acid, 2-methyl-, 2-methyl-4-oxo-4H-pyran-3-yl ester; 2-Buten-1-ol, 2-ethyl- 4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1R,4S,4aS,6R,8aS)-; 2H-1, 5-Benzodioxepin-3(4H)-one, 7-(1,1-dimethylethyl)-; Benzoic acid, phenylmethyl ester; 8-Cyclohexadecen-1-one; Benzoic acid, 2-hydroxy-, (3Z)-3-hexen-1-yl ester; 4H-Pyran-4-one, 2-ethyl-3-hydroxy-; Cyclopentadecanone, 3-methyl-; Benzoic acid, 2-hydroxy-, phenylmethyl ester; 6,8-Nonadien-3-one, 2,4,4,7-tetram- 50 ethyl-, oxime; Benzoic acid, 2-hydroxy-, cyclohexyl ester; Benzene, [2-(dimethoxymethyl)-1-hepten-1-yl]-; 3-Cy- clopentene-1-butanol, β,2,2,3-tetramethyl-δ-methylene-; 4-Penten-1-one, 1-spiro[4.5]dec-7-en-7-yl-; Acetic acid, 2-(1-oxopropoxy)-, 1-(3,3-dimethylcyclohexyl)ethyl ester; 2-Penten-1-ol, 5-[(1R,3R,6S)-2,3-dimethyltricyclo[2.2.1.02,6]hept-3-yl]-2-methyl-, (2Z)-; 4-Penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 5,8- Methano-2H-1-benzopyran-2-one, 6-ethylideneoctahydro-; 4-Cyclopentadecen-1-one, (4Z)-; Ethanone, 55 1-[(3R,3aR,7R, 8aS)-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-5-yl]-; 1,3-Dioxolane, 2,4-dimethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-; Oxacyclohexadecan-2-one; 1-Propanol, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methyl-, 1-propanoate; 5-Cyclopentadecen-1-one, 3-methyl-; 2-Penten-1- ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)-; 2H-1,5-Benzodioxepin-3(4H)-one,

45 EP 2 961 374 B1

7-(3-methylbutyl)-; Ethanone, 1-(2,6,10-trimethyl-2,5,9-cyclododecatrien-1-yl)-; 1H-3a,6-Methanoazulene-3-methanol, octahydro-7,7-dimethyl-8-methylene-, (3S,3aR,6R,8aS)-; Benzeneacetonitrile, α-cyclohexylidene-; Benzoic acid, 2-[(2-methylpentylidene)amino]-, methyl ester; Benzoic acid, 2-phenylethyl ester; 5-Cyclohexadecen-1-one; Cyclohexanol, 4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-; 3-Cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4-meth- 5 ylpentyl)-; Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-; Ethanone, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-; 2-Cyclopentadecen-1-one, 3-methyl-; Oxacycloheptadecan-2-one; Benzeneacetic acid, 4-methylphenyl ester; Benzeneacetic acid, 2-phenylethyl ester; Cyclododecaneethanol, β-methyl-; 2-Propenoic acid, 3-phenyl-, phenylmethyl ester; Benzoic acid, 2,4-dihydroxy-3,6-dimethyl-, methyl ester; Naphtho[2,1-b]furan- 6(7H)-one, 8,9-dihydro-l,5,8-trimethyl-, (8R)-; Benzeneacetic acid, (4-methoxyphenyl)methyl ester; Benzene, 2- 10 methoxy-1-(phenylmethoxy)-4-(1-propen-1-yl)-; Benzeneacetic acid, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester; Ox- acyclohexadec-12-en-2-one, (12E)-; Benzoic acid, 2-hydroxy-, 2-phenylethyl ester; 2-Propenoic acid, 3-phenyl-, 1- ethenyl-1,5-dimethyl-4-hexen-1-yl ester; Oxacycloheptadec-10-en-2-one; Oxacycloheptadec-8-en-2-one, (8Z)-; 1,7-Dioxacycloheptadecan-8-one; 7-Octen-2-ol, 8-(1H-indol-1-yl)-2,6-dimethyl-; 1,4-Dioxacyclohexadecane-5,16- dione; 1,4-Dioxacycloheptadecane-5,17-dione; Phenol, 4-[3-(benzoyloxy)-1-propen-1-yl]-2-methoxy-; Benzoic acid, 15 2-[(1-hydroxy-3-phenylbutyl)amino]-, methyl ester; and combinations thereof.

3. The composition of claim 1, wherein the volatile fragrance material is selected from the group consisting of: Formic acid, methyl ester; Methane, 1,1’-thiobis-; Acetic acid ethyl ester; Propanoic acid, ethyl ester; Acetic acid, 2-methylpropyl ester; Butanoic acid, ethyl ester; 1-Butanol; Butanoic acid, 2-methyl-, ethyl ester; 1-Butanol, 3-methyl-, 1- 20 acetate; Butanoic acid, 2-methyl-, 1-methylethyl ester; 2-Heptanone; 2-Hexenal, (2E)-; 1-Butanol, 3-methyl-; 2- Buten-1-ol, 3-methyl-, 1-acetate; 1,3-Dioxolane-2-methanamine, N-methyl-; Bicyclo[3.1.1] hept-2-ene, 2,6,6-trimethyl-, (1R,5R)-; Bicyclo[2.2.1]heptane, 2,2-dimethyl-3-methylene-; 2-Butanethiol, 4-methoxy-2-methyl-; Pentanoic acid, 2-methyl-, ethyl ester; Bicyclo[3.1.0]hexane, 4-methylene-1-(1-methylethyl)-; Bicyclo[3.1.1]heptane, 6,6-dimethyl-2-methylene-; 1-Butanol, 3-methyl-, 1-propanoate; 1,6-Octadiene, 7-methyl-3-methylene-; Octanal; 2H-Pyran, 25 2-ethenyltetrahydro-2,6,6-trimethyl-; 2-Octanone; Hexanoic acid, ethyl ester; 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-; Benzene, 1-methyl-4-(1-methylethyl)-; Benzene, 1-methoxy-4-methyl-; 1,3,6-Octatriene, 3,7-dimethyl-; Cy- clohexene, 1-methyl-4-(1-methylethenyl)-; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-; 3-Octanone; Unde- canal, 2-methyl-; Acetic acid, hexyl ester; 5-Hepten-2-one, 6-methyl-; 2-Hepten-4-one, 5-methyl-; 3-Hexen-1-ol, 1- acetate, (3Z)-; 3-Hexen-1-ol, 1-acetate; Propanoic acid, 2-hydroxy-, ethyl ester; Butanoic acid, 2-methylbutyl ester; 30 Butanoic acid, 3-methylbutyl ester; 1,4-Cyclohexadiene, 1-methyl-4-(1-methylethyl)-; Thiazole, 2-(2-methylpropyl)-; 3-Hexen-1-ol, (3Z)-; Benzaldehyde; Butanoic acid, 3-oxo-, ethyl ester; 2-Hexen-1-ol, (2E)-; 2-Hexen-1-ol, (2Z)-; Cyclohexane, 3-ethoxy-1,1,5-trimethyl-, cis- (9CI); 2-Pentanone, 4-mercapto-4-methyl-; 2,4,6-Octatriene, 2,6-dimethyl-, (4E,6E)-; Oxirane, 2,2-dimethyl-3-(3-methyl-2,4-pentadien-1-yl)-; 4,7-Octadienoic acid, methyl ester, (4E)-; Carbonic acid, (3Z)-3-hexen-1-yl methyl ester; Hexanoic acid, 2-propen-1-yl ester; 5-Heptenal, 2,6-dimethyl-; Hep- 35 tanoic acid, ethyl ester; 3-Cyclohexene-1-carboxaldehyde, 2,4-dimethyl-; Benzene, (2,2-dimethoxyethyl)-; 2H- Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-; 3-Nonanone; Benzonitrile; 3-Octanol; 1-Hexanol, 3,5,5-trimethyl-, 1-acetate; 4-Heptanol, 2,6-dimethyl-, 4-acetate; Hexanoic acid, 2-methylpropyl ester; Propanoic acid, 2- methyl-, hexyl ester; Cyclohexanecarboxylic acid, 1,4-dimethyl-, methyl ester, trans-; Benzeneacetaldehyde; Buta- noic acid, 3-hydroxy-, ethyl ester; Propanedioic acid, 1,3-diethyl ester; Benzoic acid, methyl ester; 1,3,5-Undeca- 40 triene; 4-Decenal, (4E)-; 1,3-Dioxane, 2-butyl-4,4,6-trimethyl-; 2-Heptanol, 2,6-dimethyl-; Ethanone, 1-phenyl-; Ben- zeneacetaldehyde, α-methyl-; Propanoic acid, 2-methyl-, 1,3-dimethyl-3-buten-1-yl ester; 2,6-Nonadienal, (2E,6Z)-; Pyrazine, 2-methoxy-3-(2-methylpropyl)-; Formic acid, phenylmethyl ester; Benzene, 1-methoxy-4-propyl-; Cy- clohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5R)-rel-; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-; 2-Nonenal; Cyclohexanone, 2-ethyl-4,4-dimethyl-; Benzene, 1,4-dimethoxy-; Benzene, 1-(ethoxymethyl)-2-meth- 45 oxy-; Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-; 2-Hexene, 6,6-dimethoxy-2,5,5-trimethyl-; Decanal; Benzenepro- panal, β-methyl-; Benzenemethanol, α-methyl-, 1-acetate; Acetic acid, nonyl ester; Ethanone, 1-(4-methylphenyl)-; 2H-Pyran, 6-butyl-3,6-dihydro-2,4-dimethyl-; Propanoic acid, 2-methyl-, (3Z)-3-hexen-1-yl ester; Benzoic acid, ethyl ester; 3-Octanol, 3,7-dimethyl-, 3-acetate; 1-Hexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate; Cyclohexanol, 3,3,5- trimethyl-, (1R,5R)-rel-; 2-Hexenal, 5-methyl-2-(1-methylethyl)-; 7-Octen-2-ol, 2,6-dimethyl-; Acetic acid, phenylme- 50 thyl ester; Cyclohexanone, 2-(1-methylpropyl)-; 3-Octen-1-ol, (3Z)-; Heptanoic acid, 2-propen-1-yl ester; Benzen- emethanol; Butanoic acid, 2-methyl-, hexyl ester; 2(3H)-Furanone, 5-ethyldihydro-; Cyclohexaneethanol, 1-acetate; 2-Nonenoic acid, methyl ester; Butanoic acid, (3Z)-3-hexen-1-yl ester; 2-Octynoic acid, methyl ester; 1,3-Oxathiane, 2-methyl-4-propyl-, (2R,4S)-rel-; Heptanal, 6-methoxy-2,6-dimethyl-; Bicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethyl-, 2- acetate; 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-acetate; 2-Octanol, 2,6-dimethyl-; 1-Octanol; 3-Cyclohexene-1-meth- 55 anethiol, α,α,4-trimethyl-;Cyclohexanemethanol, α,α,4-trimethyl-, 1-acetate; Cyclohexanol, 2-(1,1-dimethylethyl)-, 1-acetate; Cyclohexanol, 4-(1,1-dimethylethyl)-, 1-acetate; Pyrazine, 2-methoxy-3-(1-methylpropyl)-; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-; 2-Undecanone; Benzenepropanol, α,α-dimethyl-; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, 2-acetate, (1R, 2R,4R)-rel-; 1,6-Octadien-3-ol, 3,7-dimethyl-; Benzeneacetic acid, ethyl

46 EP 2 961 374 B1

ester; Benzeneethanol, α,α-dimethyl-; Cyclopropanecarboxylic acid, (3Z)-3-hexen-1-yl ester; 3-Cyclohexene-1- methanol, 3,5-dimethyl-, 1-acetate; Undecanal; Ethanone, 1-(3-cycloocten-1-yl)-; Cyclohexanone, 4-(1,1-dimethylethyl)-; 6-Nonen-1-ol, (6Z)-; Benzene, (2-butoxyethyl)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-; Cyclohex- anecarboxylic acid, 2,2,6-trimethyl-, ethyl ester, (1R,6S)-rel-; Benzeneethanol; 2,6-Octadienal, 3,7-dimethyl-, (2Z)-; 5 2, 6-Octadienal, 3,7-dimethyl-; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S, 5R)-rel-; Benzoic acid, 2-hydroxy-, methyl ester; Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-; 2,6-Octadiene, 1,1-dimethoxy-3,7-dimethyl-; Cyclohexanemethanol, α,3,3-trimethyl-, 1-formate; 2-Decenal, (2E)-; 3-Cyclopentene-1-acetonitrile, 2,2,3-trimethyl-; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5R)-; Cyclohexanone, 4-(1,1-dimethylpropyl)-; 6,10-Di- oxaspiro[4.5]decane, 8,8-dimethyl-7-(1-methylethyl)-; 2-Cyclohexen-1-one, 3-methyl-5-propyl-; Benzonitrile, 4-(1- 10 methylethyl)-; 2,6-Nonadienenitrile; Butanoic acid, 2-methyl-, (3Z)-3-hexen-1-yl ester; Benzene, 1-(cyclopropylmethyl)-4-methoxy-; 2-Nonynoic acid, methyl ester; Acetic acid, 2-phenylethyl ester; Cyclohexanol, 2-(1,1-dimethylethyl)-; 2,6-Nonadien-1-ol; Propanoic acid, 2-methyl-, phenylmethyl ester; Bicyclo[2.2.1]heptan-2-ol, 1, 2,3,3-tetramethyl-, (1R,2R,4S)-rel-;Benzaldehyde, 4-(1-methylethyl)-; 2,5-Octadien-4-one, 5, 6,7-trimethyl-, (2E)-; 3-Cyclohex- en-1-ol, 4-methyl-1-(1-methylethyl)-; 3-Cyclohexene-1-methanol, 2,4,6-trimethyl-; Pentanoic acid, (3Z)-3-hexen-1- 15 yl ester; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, 2-propanoate, (1R,2R,4R)-rel-; Benzene, 1-methyl-4-(1-methylethyl)-2-(1-propen-1-yl)-;3-Cyclohexene-1-propanal, β,4-dimethyl-; 1-Hexanol, 5-methyl-2-(1-methylethyl)-, (2R)-; 3-Heptanone, 5-methyl-, oxime; 2(3H)-Furanone, 5-butyldihydro-; 1-Nonanol; Acetic acid, 2-(3-methylbutoxy)-, 2- propen-1-yl ester; Bicyclo[2.2.1]heptan-2-ol, 1, 7,7-trimethyl-, (1S,2R,4S)-; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-rel-; Cyclohexanol, 2-(1,1-dimethylpropyl)-, 1-acetate; 3-Cyclohexene-1-methanol,α ,α,4-trime- 20 thyl-, 1-acetate; Cyclohexanemethanol, α,α,4-trimethyl-; 10-Undecenal; 2,4-Cyclohexadiene-1-carboxylic acid, 2,6,6-trimethyl-, ethyl ester; 1-Octanol, 3,7-dimethyl-; Furan, tetrahydro-2,4-dimethyl-4-phenyl-; Benzene, [2-(3- methylbutoxy)ethyl]-; Butanoic acid, phenylmethyl ester; Benzoic acid, 2-hydroxy-, ethyl ester; Cyclohexanol, 4-(1,1- dimethylethyl)-; 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-formate; Dodecanal; 3,6-Nonadien-1-ol, (3Z,6Z)-; 3,6-Nonadien- 1-ol; Decanenitrile; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R, 2S,5R)-; Propanoic acid, 2-methyl-, 4-methyl- 25 phenyl ester; Propanoic acid, 2-methyl-, (1R,2S, 4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-; Acetaldehyde, 2-(4-methylphenoxy)-; 2-Butenoic acid, 2-methyl-, (3Z)-3-hexen-1-yl ester, (2E)-; Bicyclo[3.1.1]hept-2-ene-2-propanal, 6,6-dimethyl-; 2-Nonanol, 6,8-dimethyl-; Cyclohexanol, 1-methyl-3-(2-methylpropyl)-; 1H-Indole; 2-Undece- nal; 2H-Pyran-2-one, 4,6-dimethyl-; 3-Cyclohexene-1-methanol, α,α,4-trimethyl-; 3-Hepten-2-one, 3,4,5,6,6-pentamethyl-, (3Z)-; 2(3H)-Furanone, 5-butyldihydro-4-methyl-; 7-Octen-2-ol, 2,6-dimethyl-, 2-acetate; 2-Propenal, 3- 30 phenyl-; 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-propanoate; 1,6-Nonadien-3-ol, 3,7-dimethyl-, 3-acetate; Cyclopen- tanone, 2,2,5-trimethyl-5-pentyl-; 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, (2Z)-; 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetate, (2E)-; Undecane, 1,1-dimethoxy-2-methyl-; Benzenemethanol, α-methylene-, 1-acetate; Benzal- dehyde, 4-methoxy-; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, 1-acetate, (1R,2S,5R)-; 6-Octenenitrile, 3,7- dimethyl-;6-Octen-2-ol, 2,6-dimethyl-; Benzene, 1,1’-oxybis-; Benzoic acid, butyl ester; 5,8-Methano-2H-1-benzo- 35 pyran, 6-ethylideneoctahydro-; Cyclohexanepropanol, α,α-dimethyl-; Benzenepropanal, β-methyl-3-(1-methylethyl)-; Benzenemethanol, 4-methoxy-, 1-acetate; Phenol, 2-ethoxy-4-methyl-; Benzene, [2-(1-propoxyethoxy)ethyl]-; 7-Octen-1-ol, 3,7-dimethyl-; Bicyclo[4.3.1] decane, 3-methoxy-7,7-dimethyl-10-methylene-; Propanoic acid, 2-(1,1- dimethylpropoxy)-, propyl ester, (2S)-; Benzoic acid, 2-(methylamino)-, methyl ester; 6-Octen-1-ol, 3,7-dimethyl-, (3S)-; 7-Octen-2-ol, 2-methyl-6-methylene-; 4,6-Octadien-3-ol, 3,7-dimethyl-; 5-Oxatricyclo[8.2.0.04,6]dodecane, 40 4,9,12,12-tetramethyl-; 2-Cyclohexene-1-carboxylic acid, 2-ethyl-6,6-dimethyl-, ethyl ester; 3-Buten-2-one, 4-(2,6,6- trimethyl-1-cyclohexen-1-yl)-, (3E)-; 4,7-Methano-1H-inden-5-ol, octahydro-, 5-acetate; Benzoic acid, 2-amino-, methyl ester; Spiro[1,3-dioxolane-2,8’(5’H)-[2H-2,4a]methanonaphthalene], hexahydro-1’,1’,5’,5’-tetramethyl-, (2’S,4’aS,8’aS)- (9CI); Spiro[1,3-dioxolane-2,8’(5’H)-[2H-2,4a]methanonaphthalene], hexahydro-1’,1’,5’,5’-tetramethyl-; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-; Benzeneethanol, α,α-dimethyl-, 1-acetate; 4,7- 45 Methano-1H-inden-5-ol, 3a,4,5,6,7,7a-hexahydro-, 5-acetate; 6-Octen-1-ol, 3,7-dimethyl-, 1-acetate; 2H-Pyran, tetrahydro-2-methyl-4-methylene-6-phenyl-; Bicyclo[3.3.1]nonane, 2-ethoxy-2,6,6-trimethyl-9-methylene-; 2,6-Octad- ien-1-ol, 3,7-dimethyl-, (2E)-; Bicyclo[7.2.0] undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-; 1H-3a,7- Methanoazulene, octahydro-6-methoxy-3,6,8,8-tetramethyl-, (3R,3aS,6S,7R,8aS)-; Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-; 1H-Inden-1-one, 2,3-dihydro-2,3,3-trimethyl-;2-Propanol, 1,1’-oxy- 50 bis-;2-Octanol, 7-methoxy-3,7-dimethyl-; 4,9-Decadienal, 4,8-dimethyl-; Benzoic Acid; 3-Hexenoic acid, (3Z)-3-hexen-1-yl ester, (3Z)-; Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 3-(1-methylethyl)-, ethyl ester, (1R,2S,3S,4S)-rel-; 2-Propen-1-ol, 3-phenyl-; Propanoic acid, 2-methyl-, 1-ethenyl-1,5-dimethyl-4-hexen-1-yl ester; Ethanol, 2-phenoxy-, 1-propanoate; 2-Propenoic acid, 3-phenyl-, methyl ester; Benzenepropanal, 2-ethyl-a,a-dimethyl-; Propanoic acid, decyl ester; Benzene, 1,2-dimethoxy-4-(1-propen-1-yl)-; 3-Decen-5-ol, 4-methyl-; Phenol, 2-methoxy-4-(2- 55 propen-1-yl)-; 1-Propanone, 1-[2-methyl-5-(1-methylethyl)-2-cyclohexen-1-yl]-; 1,3-Benzodioxole-5-carboxaldehyde; 2-Dodecenal; 2-Dodecenal, (2E)-; Benzenepropanal, 4-methoxy- α-methyl-; 1,4-Cyclohexanedicarboxylic acid, 1,4-dimethyl ester; 2-Buten-1-one, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-; 2-Butanone, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 2-Propenenitrile, 3-phenyl-, (2E)-; Propanoic acid, 2-methyl-, 2-phenylethyl ester; 2-Cyclopenten-

47 EP 2 961 374 B1

1-one, 3-methyl-2-(2Z)-2-penten-1-yl-; Acetaldehyde, 2-[(3,7-dimethyl-6-octen-1-yl)oxy]-; 1-Cyclohexene-1-ethanol, 4-(1-methylethyl)-, 1-formate; 2,4-Decadienoic acid, ethyl ester, (2E,4Z)-; 2-Propen-1-ol, 3-phenyl-, 1-acetate; Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS, 9bR)-; Benzenepropanal, 4-(1,1-dimethylethyl)-; Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-; 1,4-Methanonaphthalen-5(1H)-one, 5 4,4a,6,7,8,8a-hexahydro-; Dodecanoic acid, 12-hydroxy-, λ-lactone (6CI,7CI); 1,12-; Cyclohexanepropanoic acid, 2-propen-1-yl ester; 2(3H)-Furanone, 5-hexyldihydro-5-methyl-; 2,6-Nonadienenitrile, 3,7-dimethyl-; 10-Undecenoic acid, ethyl ester; Benzenepropanal,α-methyl-4-(1-methylethyl)-; 1-Oxaspiro[4.5]decan-2-one, 8-methyl-; 2(3H)-Furanone, dihydro-5-pentyl-; 2(3H)-Furanone, 5-hexyldihydro-; 2-Buten-1-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (2E)-; 2-Buten-1-one, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-, (2E)-; 2H-Pyran-2-one, tetrahydro-6-pentyl-; 10 Benzenepropanal, 4-ethyl-α,α-dimethyl-; 1,3-Benzodioxole, 5-(diethoxymethyl)-; 4-Penten-1-one, 1-(5,5-dimethyl- 1-cyclohexen-1-yl)-; Bicyclo[3.1.1]hept-2-ene-2-ethanol, 6,6-dimethyl-, 2-acetate; 2-Propenoic acid, 3-phenyl-, ethyl ester; 1,3-Dioxane, 2,4,6-trimethyl-4-phenyl-; Cyclododecane, (methoxymethoxy)-; Bicyclo[3.1.1]hept-2-ene-2-propanal, α,α,6,6-tetramethyl-; Benzeneacetonitrile, 4-(1,1-dimethylethyl)-; 2-Buten-1-one, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 1,4-Methanonaphthalen-6(2H)-one, octahydro-7-methyl-; Bicyclo[3.2.1]octan-8-one, 1,5-dimethyl-, 15 oxime; Benzenepentanol, γ-methyl-; Cyclohexene, 4-(1,5-dimethyl-4-hexen-1-ylidene)-1-methyl-; Phenol, 2-methoxy-4-propyl-; Benzoic acid, 2-hydroxy-, 2-methylpropyl ester; 2H-1-Benzopyran-2-one, octahydro-;Cyclohexanone, 2-(1-mercapto-1-methylethyl)-5-methyl-; 2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester; 3-Cyclohexene- 1-carboxaldehyde, 4-(4-methyl-3-penten-1-yl)-; Propanoic acid, 2-methyl-, 2-phenoxyethyl ester; Indeno[1,2-d]-1,3- dioxin, 4,4a,5,9b-tetrahydro-; 2H-Pyran-4-ol, tetrahydro-4-methyl-2-(2-methylpropyl)-; Cyclohexanebutanal, 20 α,2,6,6-tetramethyl-; 1,6-Nonadien-3-ol, 3,7-dimethyl-; 3-Buten-2-one, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1- yl)-; Phenol, 2-methoxy-4-(1-propen-1-yl)-; 2(3H)-Furanone, 5-hexyldihydro-4-methyl-; 1-Penten-3-one, 1-(2,6,6- trimethyl-2-cyclohexen-1-yl)-; 2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-; 2-Cyclopenten-1-one, 2- hydroxy-3-methyl-; Propanoic acid, 2,2-dimethyl-, 2-phenylethyl ester; Dodecanenitrile; 6-Octen-1-ol, 3,7-dimethyl-, 1-propanoate; Benzenepentanal, β-methyl-; Acetic acid, 2-phenoxy-, 2-propen-1-yl ester; Benzenepropanal, 4-(1,1- 25 dimethylethyl)-α-methyl-; 4,7-Methano-1H-indene-2-carboxaldehyde, octahydro-5-methoxy-; Pentitol, 1,5-anhydro- 2,4-dideoxy-2-pentyl-, 3-acetate; Cyclododecane, (ethoxymethoxy)-; 3-Buten-2-one, 4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-; Quinoline, 6-(1-methylpropyl)-; Carbonic acid, 4-cycloocten-1-yl methyl ester; 1H-Indene-5-propanal, 2, 3-dihydro-3,3-dimethyl-; Ethanone, 1-(3-methyl-2-benzofuranyl)-; 3-Cyclohexene-1-carboxaldehyde, 1- methyl-3-(4-methyl-3-penten-1-yl)-; 6-Oxabicyclo[3.2.1]octane, 5-methyl-1-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 30 2H-Pyran-2-one, tetrahydro-6-(3-penten-1-yl)-; 2,4,7-Decatrienoic acid, ethyl ester; Butanoic acid, 3-methyl-, 2- phenylethyl ester; Spiro[1,4-methanonaphthalene-2(1H),2’-oxirane], 3,4,4a,5,8,8a-hexahydro-3’,7-dimethyl-; Etha- nol, 2-[[(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]oxy]-, rel-; Phenol, 2-methoxy-4-(1-propen-1-yl)-, 1-acetate; 2H-Indeno[4,5-b]furan, decahydro-2,2,6,6,7,8,8-heptamethyl-; Acetic acid, 2-(cyclohexyloxy)-, 2-propen-1-yl ester; Octanal, 7-hydroxy-3,7-dimethyl-; Naphtho[2,1-b]furan, 9b-ethyldodecahydro-3a,7,7-trimethyl-; 1,6-Heptadi- 35 en-3-one, 2-cyclohexyl-; 5-Thiazoleethanol, 4-methyl-; 1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; 3- Buten-2-one, 3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; 1,4-Cyclohexanedicarboxylic acid, 1,4-diethyl ester; 2(3H)-Furanone, 5-heptyldihydro-; 1,3-Benzodioxole-5-propanal, α-methyl-; 4H-Inden-4-one, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-; Cyclohexanone, 4-(1-ethoxyethenyl)-3,3,5,5-tetramethyl-;Benzenepropanenitrile,α - ethenyl-α-methyl-; 9-Undecenal, 2,6,10-trimethyl-; Pyridine, 2-(3-phenylpropyl)-; Indeno[1,2-d]-1,3-dioxin, 40 4,4a,5,9b-tetrahydro-2,4-dimethyl-;Propanoic acid, 2-methyl-, 3a,4,5,6,7,7a-hexahydro-4,7-methano-1H-inden-5-yl ester; 1-Naphthalenol, 1,2,3, 4,4a,7,8,8a-octahydro-2,4a,5,8a-tetramethyl-, 1-formate; Benzenepropanol, β,β,3-trimethyl-; 2-Cyclohexen-1-one, 4-(2-buten-1-ylidene)-3,5,5-trimethyl-; 3-Hexen-1-ol, 1-benzoate, (3Z)-; Benzalde- hyde, 4-hydroxy-3-methoxy-; 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, 6-acetate, (3R,3aS,6R,7R,8aS)-; 4,7-Methano-1H-inden-6-ol, 3a,4,5,6,7,7a-hexahydro-8,8-dimethyl-, 6-propanoate; 2-Ox- 45 iranecarboxylic acid, 3-phenyl-, ethyl ester; 4H-4a,9-Methanoazuleno[5,6-d]-1,3-dioxole, octahydro-2,2,5,8,8,9a- hexamethyl-, (4aR,5R,7aS,9R)-; Butanoic acid, 1,1-dimethyl-2-phenylethyl ester; Cyclododeca[c]furan, 1, 3,3a,4,5,6,7,8,9,10,11,13a-dodecahydro-; Benzenebutanenitrile, α,α,γ-trimethyl-; 2-Butanone, 4-(1,3-benzodioxol- 5-yl)-; Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester; 3-Cyclopentene-1-butanol, β,2,2,3-tetramethyl-2-Methyl- 4-(2,2,3-trimethyl-3-cyclopenten-1-yl)butanol; 2-Butenal, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 2-Naph- 50 thalenol, decahydro-2,5,5-trimethyl-;1,7-Octanediol, 3,7-dimethyl-; 2H-1-Benzopyran-2-one; 1,3-Dioxolane, 2-[6- methyl-8-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-; Propanoic acid, 2,2-dimethyl-, 3a,4,5,6,7,7a-hexahydro-4,7- methano-1H-inden-6-yl ester; Butanoic acid, (2E)-3, 7-dimethyl-2,6-octadien-1-yl ester; 2-Butanone, 4-(4-hydroxyphenyl)-; 10-Undecenoic acid, butyl ester; and combinations thereof.

55 4. The composition of claim 1, wherein the volatile fragrance material is selected from the group consisting of:

(i) a high volatile fragrance material having a vapor pressure > 0.1 Torr at 25°C; (ii) a moderate volatile fragrance material having a vapor pressure in the range of 0.1 Torr at 25°C to 0.001 Torr

48 EP 2 961 374 B1

at 25°C; and (iii) combinations thereof.

5. The composition of claim 1, further comprising ethanol in the amount of from 50 wt% to 80 wt%, or from 55 wt% to 5 75 wt%, relative to the total weight of the composition.

6. The composition of claim 1, further comprising one or more non-odorous fragrance co-modulators selected from the group consisting of:

10 (i) Isocetyl alcohol; (ii) PPG-3 myristyl ether; (iii) Neopentyl glycol diethylhexanoate; and (iv) mixtures thereof preferably with isocetyl alcohol.

15 wherein the one or more non-odorous fragrance co-modulators are present in the amount of from 0.05 wt% to 10 wt%, preferably from 0.5 wt% to 6 wt%, relative to the total weight of the composition.

7. The composition of claim 8, wherein the non-odorous fragrance modulators are formed of at least 50 wt% of a non- odorous fragrance modulator, relative to the combined weight of the non-odorous fragrance modulators and the 20 non-odorous fragrance co-modulators.

8. The composition according to claim 1, further comprising one or more non-odorous fragrance co-modulators selected from the group consisting of Isocetyl alcohol, PPG-3 myristyl ether, Neopentyl glycol diethylhexanoate or mixture thereof preferably with isocetyl alcohol, preferably in the amount of from 0.5 wt% to 6 wt%, relative to the total weight 25 of the composition.

9. A method to enhance the fragrance profile of a composition, preferably improve the longevity of an aroma, preferably a floral aroma, of a composition, comprising bringing into contact or mixing at least one non-odorous fragrance modulator with at least one low volatile fragrance material according to a composition as defined in any preceding 30 claims.

10. The method of claim 9, wherein the floral aroma is selected from the group consisting of a lavender-type note, a rose-type note, a lily of the valley-type note, a muguet-type note, a jasmine-type note, a magnolia-type note, a cyclamen-type note, a hyacinth-type note, a lilac-type note, an orange blossom-type note, a cherry blossom-type 35 note, a peony-type note, a lotus-type note, a linden blossom-type note, an osmanthus-type note, a lilac-type note, a heliotrope-type note, a violet-type note, an orris-type note, a tiare-type note and combinations thereof.

11. A method for producing a consumer product comprising bringing into contact or mixing into the product an orga- noleptically active quantity of a fragrance composition according to any one of claims 1-8. 40 12. A perfuming consumer product or article comprising a fragrance composition according to any one of claims 1-8, wherein the perfuming consumer product is selected from the group consisting of a fabric care product, an air care product, or a home care product.

45 13. A method of modifying or enhancing the odour properties of a body surface, comprising contacting or treating the body surface with a composition according to any one of claims 1-8.

Patentansprüche 50 1. Zusammensetzung, umfassend:

(i) eine in einer Menge von 1 Gew.-% bis 30 Gew.-%, vorzugsweise weniger als 25 Gew.-%, vorzugsweise weniger als 20 Gew.-%, vorzugsweise weniger als 15 Gew.-%, vorzugsweise weniger als 10 Gew.-% oder 55 vorzugsweise weniger als 8 Gew.-% im Verhältnis zum Gesamtgewicht der Zusammensetzung vorhandene Duftstoffkomponente; und wobei:

(a) die Duftstoffkomponente wenigstens ein niederflüchtiges Duftstoffmaterial umfasst, das einen Dampf-

49 EP 2 961 374 B1

druck von < 0,133 Pa (0,001 Torr) bei 25 °C aufweist; (b) das niederflüchtige Duftstoffmaterial in einer Menge von ab 0,1 Gew.-% bis 30 Gew.-%, vorzugsweise weniger als 25 Gew.-%, vorzugsweise weniger als 20 Gew.-% oder vorzugsweise weniger als 12 Gew.-% im Verhältnis zum Gesamtgewicht der Duftstoffkomponente vorhanden ist; 5 (c) die Duftstoffkomponente außerdem ein oder mehrere flüchtige Duftstoffmaterialen umfasst, die einen Dampfdruck von ≥ 0,133 Pa (0,001 Torr) bei 25 °C aufweisen; und (d) das flüchtige Duftstoffmaterial in einer Menge von ab 70 Gew.-% bis 99,9 Gew.-%, vorzugsweise mehr als 80 Gew.-% oder am meisten bevorzugt mehr als 88 Gew.-% im Verhältnis zum Gesamtgewicht der Duftstoffkomponente vorhanden ist; und 10 (ii) wenigstens einen geruchlosen Duftstoffmodulator, der aus einem alkoxylierten Glucosid gebildet ist, aus- gewählt aus der Gruppe bestehend aus Methylglucosidpolyol, Ethylglucosidpolyol und Propylglucosidpolyol, vorzugsweise PPG-10 Methlyglucoseether, PPG-20 Methlyglucoseether, ethoxyliertem Methlyglucoseether, Caprylyl/Caprylglucosid, Undecylglucosid oder Kombinationen davon in einer Menge von ab 0,1 Gew.-% bis 15 20 Gew.-%, vorzugsweise 0,5 Gew.-% bis 18 Gew.-% oder mehr bevorzugt 2,5 Gew.-% bis 15 Gew.-% im Verhältnis zum Gesamtgewicht der Zusammensetzung.

2. Zusammensetzung nach Anspruch 1, wobei das niederflüchtige Duftstoffmaterial ausgewählt ist aus der Gruppe bestehend aus: 2-Buten-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; Ethanon, 1-(2-naphthalenyl)-; 3-De- 20 canon, 1-hydroxy-; Cyclopropanmethanol, 1-methyl-2-[(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)methyl]-; Benzalde- hyd, 3-ethoxy-4-hydroxy-; 2H-1,5-Benzodioxepin-3(4H)-on, 7-methyl-; 2-Butanol, 1-[[2-(1,1-dimethylethyl)cyclohexyl]oxy]-; Spiro[5.5]undec-8-en-1-on, 2,2,7,9-tetramethyl-; Cyclopentanessigsäure, 3-oxo-2-pentyl-, methylester, (1 R,2R)-rel-; Cyclopentanessigsäure, 3-oxo-2-pentyl-, methylester; Octanal, 2-(phenylmethylen)-; Cyclopentancar- bonsäure, 2-hexyl-3-oxo-, methylester; 3-Cyclopenten-1-butanol, α,β,2,2,3-pentamethyl-; Cyclopentanon, 2-(3,7- 25 dimethyl-2,6-octadien-1-yl)-; 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-; 2-Pentennitril, 3-methyl-5-phenyl-, (2Z)-; Benzenpropannitril, 4-ethyl-α,α-dimethyl-; 1H-3a,7-Methanazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)-; Ethanon, 1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-; Propansäure, 2- methyl-, 4-formyl-2-methoxyphenylester; 1,6-Heptadien-3-on, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; Benzoesäure, 2-hydroxy-, hexylester; Benzoesäure, phenylester; Cyclohexanpropanol, 2,2,6-trimethyl-α-propyl-, (1 R,6S)-; Cyc- 30 lohexanpropanol, 2,2,6-trimethyl-α-propyl-; Benzoesäure, 2-hydroxy-, 3-methyl-2-buten-1-ylester; 2H-1,5-Benzodi- oxepin-3(4H)-on, 7-(1-methylethyl)-; Butanal, 4-(octahydro-4,7-methano-5H-inden-5-yliden)-; Cyclopenta[g]-2-benzopyran, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-; Cyclopentanon, 2-[2-(4-methyl-3-cyclohexen-1-yl)propyl]-; 2(3H)-Naphthalenon, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-; 2-Propen- säure, 3-phenyl-, pentylester; 4H-Pyran-4-on, 3-hydroxy-2-methyl-; 1-Propanol, 2-methyl-3-[(1,7,7-trimethylbicyc- 35 lo[2.2.1]hept-2-yl)oxy]-; 1-Naphthalenol, 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8-tetramethyl-; 2-Butensäure, 2-methyl-, (2E)-3,7-dimethyl-2,6-octadien-1-ylester, (2E)-; 1,3-Dioxan, 2-(2,4-dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-; Nonadecan; 4-Penten-2-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; Propansäure, 2-Methyl-, 2-Methyl-4-oxo-4H-pyran-3-ylester; 2-Buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 1,6-Methannaph- thalen-1 (2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1 R,4S,4aS,6R,8aS)-; 2H-1,5-Benzodioxepin-3(4H)-on, 7-(1,1- 40 dimethylethyl)-; Benzoesäure, phenylmethylester; 8-Cyclohexadecen-1-on; Benzoesäure, 2-hydroxy-, (3Z)-3-hexen-1-ylester; 4H-Pyran-4-on, 2-ethyl-3-hydroxy-; Cyclopentadecanon, 3-methyl-; Benzoesäure, 2-hydroxy-, phenylmethylester; 6,8-Nonadien-3-on, 2,4,4,7-tetramethyl-, oxim; Benzoesäure, 2-hydroxy-, cyclohexylester; Benzen, [2-(dimethoxymethyl)-1-hepten-1-yl]-; 3-Cyclopenten-1-butanol, β,2,2,3-tetramethyl-δ-methylen-; 4-Penten-1-on, 1- spiro[4.5]dec-7-en-7-yl-; Essigsäure, 2-(1-oxopropoxy)-, 1-(3,3-dimethylcyclohexyl)ethylester; 2-Penten-1-ol, 5-[(1 45 R,3R,6S)-2,3-dimethyltricyclo[2.2.1.02,6]hept-3-yl]-2-methyl-, (2Z)-; 4-Penten-2-ol, 3,3-dimethyl-5-(2,2,3-trimethyl- 3-cyclopenten-1-yl)-; 5,8-Methan-2H-1-benzopyran-2-on, 6-ethylidenoctahydro-; 4-Cyclopentadecen-1-on, (4Z)-; Ethanon, 1-[(3R,3aR,7R,8aS)-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanazulen-5-yl]-; 1,3-Dio- xolan, 2,4-dimethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-; Oxacyclohexadecan-2-on; 1-Propa- nol, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methyl-, 1-propanoat; 5-Cyclopentadecen-1-on, 3-methyl-; 2-Penten-1- 50 ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)-; 2H-1,5-Benzodioxepin-3(4H)-on, 7-(3-methylbutyl)-; Ethanon, 1-(2,6,10-trimethyl-2,5,9-cyclododecatrien-1-yl)-; 1H-3a,6-Methanazulen-3-methanol, octahydro-7,7-dimethyl-8-methylen-, (3S,3aR,6R,8aS)-; Benzenacetonitril, α-cyclohexyliden-; Benzoesäure, 2-[(2- methylpentylidene)amino]-, methylester; Benzoesäure, 2-phenylethylester; 5-Cyclohexadecen-1-on; Cyclohexanol, 4-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-; 3-Cyclohexen-1-carboxaldehyd, 4-(4-hydroxy-4-methylpentyl)-; Etha- 55 non, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl)-; Ethanon, 1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-; 2-Cyclopentadecen-1-on, 3-methyl-; Oxacycloheptadecan-2-on; Benzenessigsäure, 4-methylphenylester; Benzenessigsäure, 2-Phenylethylester; Cyclododecaneethanol, β-methyl-; 2-Propensäure, 3-phenyl-, phenylmethylester; Benzoesäure, 2,4-dihydroxy-3,6-dimethyl-, methylester; Naphtho[2,1-b]furan-6(7H)-on, 8,9-dihy-

50 EP 2 961 374 B1

dro-1,5,8-trimethyl-, (8R)-; Benzenessigsäure, (4-methoxyphenyl)methylester; Benzen, 2-methoxy-1-(phenylmethoxy)-4-(1-propen-1-yl)-; Benzenessigsäure, (2E)-3,7-dimethyl-2,6-octadien-1-ylester; Oxacyclohexadec-12-en-2- on, (12E)-; Benzoesäure, 2-hydroxy-, 2-phenylethylester; 2-Propensäure, 3-phenyl-, 1-ethenyl-1,5-dimethyl-4-hexen-1-ylester; Oxacycloheptadec-10-en-2-on; Oxacycloheptadec-8-en-2-on, (8Z)-; 1,7-Dioxacycloheptadecan-8- 5 on; 7-Octen-2-ol, 8-(1 H-indol-1-yl)-2,6-dimethyl-; 1,4-Dioxacyclohexadecan-5,16-dion; 1,4-Dioxacycloheptadecan- 5,17-dion; Phenol, 4-[3-(benzoyloxy)-1-propen-1-yl]-2-methoxy-; Benzoesäure, 2-[(1-hydroxy-3-phenylbutyl)amino]-, methylester; und Kombinationen davon.

3. Zusammensetzung nach Anspruch 1, wobei das flüchtige Duftstoffmaterial ausgewählt ist aus der Gruppe bestehend 10 aus: Ameisensäure, Methylester; Methan, 1,1’-thiobis-; Essigsäureethylester; Propansäure, Ethylester; Essigsäure, 2-methylpropylester; Butansäure, Ethylester; 1-Butanol; Butansäure, 2-methyl-, Ethylester; 1-Butanol, 3-methyl-, 1- acetat; Butansäure, 2-methyl-, 1-methylethylester; 2-Heptanon; 2-Hexenal, (2E)-; 1-Butanol, 3-methyl-; 2-Buten-1- ol, 3-methyl-, 1-acetat; 1,3-Dioxolan-2-methanamin, N-methyl-; Bicyclo[3.1.1]hept-2-en, 2,6,6-trimethyl-, (1R,5R)-; Bicyclo[2.2.1]heptan, 2,2-dimethyl-3-methylen-; 2-Butanethiol, 4-methoxy-2-methyl-; Pentansäure, 2-methyl-, Ethyl- 15 ester; Bicyclo[3.1.0]hexan, 4-methylen-1-(1-methylethyl)-; Bicyclo[3.1.1]heptan, 6,6-dimethyl-2-methylen-; 1-Buta- nol, 3-methyl-, 1-propanoat; 1,6-Octadien, 7-methyl-3-methylen-; Octanal; 2H-Pyran, 2-ethenyltetrahydro-2,6,6-trimethyl-; 2-Octanon; Hexansäure, Ethylester; 2-Oxabicyclo[2.2.2]octan, 1,3,3-trimethyl-; Benzen, 1-methyl-4-(1-methylethyl)-; Benzen, 1-methoxy-4-methyl-; 1,3,6-Octatrien, 3,7-dimethyl-; Cyclohexen, 1-methyl-4-(1-methylethenyl)-; Cyclohexen, 1-methyl-4-(1-methylethenyl)-, (4R)-; 3-Octanon; Undecanal, 2-methyl-; Essigsäure, hexylester; 20 5-Hepten-2-on, 6-methyl-; 2-Hepten-4-on, 5-methyl-; 3-Hexen-1-ol, 1-acetat, (3Z)-; 3-Hexen-1-ol, 1-acetat; Propan- säure, 2-hydroxy-, Ethylester; Butansäure, 2-methylbutylester; Butansäure, 3-methylbutylester; 1,4-Cyclohexadien, 1-methyl-4-(1-methylethyl)-; Thiazol, 2-(2-methylpropyl)-; 3-Hexen-1-ol, (3Z)-; Benzaldehyd; Butansäure, 3-oxo-, Ethylester; 2-Hexen-1-ol, (2E)-; 2-Hexen-1-ol, (2Z)-; Cyclohexan, 3-ethoxy-1,1,5-trimethyl-, cis- (9Cl); 2-Pentanon, 4-mercapto-4-methyl-; 2,4,6-Octatrien, 2,6-dimethyl-, (4E,6E)-; Oxiran, 2,2-dimethyl-3-(3-methyl-2,4-pentadien-1- 25 yl)-; 4,7-Octadiensäure, Methylester, (4E)-; Kohlensäure, (3Z)-3-hexen-1-yl methylester; Hexansäure, 2-propen-1- ylester; 5-Heptenal, 2,6-dimethyl-; Heptansäure, Ethylester; 3-Cyclohexen-1-carboxaldehyd, 2,4-dimethyl-; Benzen, (2,2-dimethoxyethyl)-; 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-; 3-Nonanon; Benzonitril; 3-Octa- nol; 1-Hexanol, 3,5,5-trimethyl-, 1-acetat; 4-Heptanol, 2,6-dimethyl-, 4-acetat; Hexansäure, 2-methylpropylester; Propansäure, 2-methyl-, hexylester; Cyclohexancarboxylsäure, 1,4-dimethyl-, Methylester, trans-; Benzenacetal- 30 dehyd; Butansäure, 3-hydroxy-, Ethylester; Propandisäure, 1,3-diethylester; Benzoesäure, Methylester; 1,3,5-Un- decatrien; 4-Decenal, (4E)-; 1,3-Dioxan, 2-butyl-4,4,6-trimethyl-; 2-Heptanol, 2,6-dimethyl-; Ethanon, 1-phenyl-; Benzenacetaldehyd, α-methyl-; Propansäure, 2-methyl-, 1,3-dimethyl-3-buten-1-ylester; 2,6-Nonadienal, (2E,6Z)-; Pyrazin, 2-methoxy-3-(2-methylpropyl)-; Ameisensäure, phenylmethylester; Benzen, 1-methoxy-4-propyl-; Cyclo- hexanon, 5-methyl-2-(1-methylethyl)-, (2R,5R)-rel-; Cyclohexanon, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-; 2-No- 35 nenal; Cyclohexanon, 2-ethyl-4,4-dimethyl-; Benzen, 1,4-dimethoxy-; Benzen, 1-(ethoxymethyl)-2-methoxy-; Bicy- clo[2.2.1]heptan-2-on, 1,7,7-trimethyl-; 2-Hexen, 6,6-dimethoxy-2,5,5-trimethyl-; Decanal; Benzenpropanal, β-methyl-; Benzenmethanol, α-methyl-, 1-acetat; Essigsäure, nonylester; Ethanon, 1-(4-methylphenyl)-; 2H-Pyran, 6- butyl-3,6-dihydro-2,4-dimethyl-; Propansäure, 2-methyl-, (3Z)-3-hexen-1-ylester; Benzoesäure, Ethylester; 3-Octa- nol, 3,7-dimethyl-, 3-acetat; 1-Hexanol, 5-methyl-2-(1-methylethyl)-, 1-acetat; Cyclohexanol, 3,3,5-trimethyl-, 40 (1R,5R)-rel-; 2-Hexenal, 5-methyl-2-(1-methylethyl)-; 7-Octen-2-ol, 2,6-dimethyl-; Essigsäure, phenylmethylester; Cyclohexanon, 2-(1-methylpropyl)-; 3-Octen-1-ol, (3Z)-; Heptansäure, 2-propen-1-ylester; Benzenmethanol; Butan- säure, 2-methyl-, hexylester; 2(3H)-Furanon, 5-ethyldihydro-; Cyclohexanethanol, 1-acetat; 2-Nonensäure, Methyl- ester; Butansäure, (3Z)-3-hexen-1-ylester; 2-Octyonicsäure, Methylester; 1,3-Oxathian, 2-methyl-4-propyl-, (2R,4S)-rel-; Heptanal, 6-methoxy-2,6-dimethyl-; Bicyclo[2.2.1]heptan-2-ol, 1,3,3-trimethyl-, 2-acetat; 1,6-Octadien- 45 3-ol, 3,7-dimethyl-, 3-acetat; 2-Octanol, 2,6-dimethyl-; 1-Octanol; 3-Cyclohexen-1-methanethiol,α ,α,4-trimethyl-; Cyclohexanmethanol, α,α,4-trimethyl-, 1-acetat; Cyclohexanol, 2-(1,1-dimethylethyl)-, 1-acetat; Cyclohexanol, 4-(1,1-dimethylethyl)-, 1-acetat; Pyrazin, 2-methoxy-3-(1-methylpropyl)-; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1 R,2S,5R)-; 2-Undecanon; Benzenpropanol,α ,α-dimethyl-; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, 2- acetat, (1 R,2R,4R)-rel-; 1,6-Octadien-3-ol, 3,7-dimethyl-; Benzenessigsäure, Ethylester; Benzenethanol,α ,α-di- 50 methyl-; Cyclopropancarboxylsäure, (3Z)-3-hexen-1-ylester; 3-Cyclohexen-1-methanol, 3,5-dimethyl-, 1-acetat; Un- decanal; Ethanon, 1-(3-cycloocten-1-yl)-; Cyclohexanon, 4-(1,1-dimethylethyl)-; 6-Nonen-1-ol, (6Z)-; Benzen, (2- butoxyethyl)-; Bicyclo[3.1.1]hept-3-en-2-on, 4,6,6-trimethyl-; Cyclohexancarboxylsäure, 2,2,6-trimethyl-, Ethylester, (1 R,6S)-rel-; Benzenethanol; 2,6-Octadienal, 3,7-dimethyl-, (2Z)-; 2,6-Octadienal, 3,7-dimethyl-; Cyclohexanol, 5- methyl-2-(1-methylethyl)-, 1-acetat, (1 R,2S,5R)-rel-; Benzoesäure, 2-hydroxy-, Methylester; Benzen, 1-methoxy- 55 4-(1E)-1-propen-1-yl-; 2,6-Octadien, 1,1-dimethoxy-3,7-dimethyl-; Cyclohexanmethanol, α,3,3-trimethyl-, 1-formiat; 2-Decenal, (2E)-; 3-Cyclopenten-1-acetonitril, 2,2,3-trimethyl-; 2-Cyclohexen-1-on, 2-methyl-5-(1-methylethenyl)-, (5R)-; Cyclohexanon, 4-(1,1-dimethylpropyl)-; 6,10-Dioxaspiro[4.5]decan, 8,8-dimethyl-7-(1-methylethyl)-; 2-Cyclo- hexen-1-on, 3-methyl-5-propyl-; Benzonitril, 4-(1-methylethyl)-; 2,6-Nonadienenitril; Butansäure, 2-methyl-, (3Z)-3-

51 EP 2 961 374 B1

hexen-1-ylester; Benzen, 1-(cyclopropylmethyl)-4-methoxy-; 2-Nonynonsäure, Methylester; Essigsäure, 2-phenylethylester; Cyclohexanol, 2-(1,1-dimethylethyl)-; 2,6-Nonadien-1-ol; Propansäure, 2-methyl-, phenylmethylester; Bicyclo[2.2.1]heptan-2-ol, 1,2,3,3-tetramethyl-, (1 R,2R,4S)-rel-;Benzaldehyd, 4-(1-methylethyl)-; 2,5-Octadien-4- on, 5,6,7-trimethyl-, (2E)-; 3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-; 3-Cyclohexen-1-methanol, 2,4,6-trime- 5 thyl-; Pentansäure, (3Z)-3-hexen-1-ylester; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, 2-propanoat, (1 R,2R,4R)-rel-; Benzen, 1-methyl-4-(1-methylethyl)-2-(1-propen-1-yl)-; 3-Cyclohexen-1-propanal, β,4-dimethyl-; 1- Hexanol, 5-methyl-2-(1-methylethyl)-, (2R)-; 3-Heptanon, 5-methyl-, oxim; 2(3H)-Furanon, 5-butyldihydro-; 1-Non- anol; Essigsäure, 2-(3-methylbutoxy)-, 2-propen-1-ylester; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S,2R,4S)-; Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1 R,2R,4R)-rel-; Cyclohexanol, 2-(1,1-dimethylpropyl)-, 1-acetat; 3-Cy- 10 clohexen-1-methanol, α,α,4-trimethyl-, 1-acetat; Cyclohexanmethanol, α,α,4-trimethyl-; 10-Undecenal; 2,4-Cyclo- hexadien-1-carboxylsäure, 2,6,6-trimethyl-, Ethylester; 1-Octanol, 3,7-dimethyl-; Furan, tetrahydro-2,4-dimethyl-4- phenyl-; Benzen, [2-(3-methylbutoxy)ethyl]-; Butansäure, phenylmethylester; Benzoesäure, 2-hydroxy-, Ethylester; Cyclohexanol, 4-(1,1-dimethylethyl)-; 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-formiat; Dodecanal; 3,6-Nonadien-1-ol, (3Z,6Z)-; 3,6-Nonadien-1-ol; Decannitril; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1 R,2S,5R)-; Propansäure, 2- 15 methyl-, 4-methylphenylester; Propansäure, 2-methyl-, (1R, 2S,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylester, rel-; Acetaldehyd, 2-(4-methylphenoxy)-; 2-Butensäure, 2-methyl-, (3Z)-3-hexen-1-ylester, (2E)-; Bicyclo[3.1.1]hept-2- en-2-propanal, 6,6-dimethyl-; 2-Nonanol, 6,8-dimethyl-; Cyclohexanol, 1-methyl-3-(2-methylpropyl)-; 1H-Indol; 2- Undecenal; 2H-Pyran-2-on, 4,6-dimethyl-; 3-Cyclohexen-1-methanol,α ,α,4-trimethyl-; 3-Hepten-2-on, 3,4,5,6,6- pentamethyl-, (3Z)-; 2(3H)-Furanon, 5-butyldihydro-4-methyl-; 7-Octen-2-ol, 2,6-dimethyl-, 2-acetat; 2-Propenal, 3- 20 phenyl-; 1,6-Octadien-3-ol, 3,7-dimethyl-, 3-propanoat; 1,6-Nonadien-3-ol, 3,7-dimethyl-, 3-acetat; Cyclopentanon, 2,2,5-trimethyl-5-pentyl-; 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetat, (2Z)-; 2,6-Octadien-1-ol, 3,7-dimethyl-, 1-acetat, (2E)-; Undecan, 1,1-dimethoxy-2-methyl-; Benzenmethanol, α-methylen-, 1-acetat; Benzaldehyd, 4-methoxy-; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, 1-acetat, (1 R,2S,5R)-; 6-Octennitril, 3,7-dimethyl-;6-Octen-2-ol, 2,6- dimethyl-; Benzen, 1,1’-oxybis-; Benzoesäure, butylester; 5,8-Methano-2H-1-benzopyran, 6-ethylideneoctahydro-; 25 Cyclohexanpropanol, α,α-dimethyl-; Benzenpropanal, β-methyl-3-(1-methylethyl)-; Benzenmethanol, 4-methoxy-, 1-acetat; Phenol, 2-ethoxy-4-methyl-; Benzen, [2-(1-propoxyethoxy)ethyl]-; 7-Octen-1-ol, 3,7-dimethyl-; Bicyc- lo[4.3.1]decan, 3-methoxy-7,7-dimethyl-10-methylen-; Propansäure, 2-(1,1-dimethylpropoxy)-, propylester, (2S)-; Benzoesäure, 2-(methylamino)-, Methylester; 6-Octen-1-ol, 3,7-dimethyl-, (3S)-; 7-Octen-2-ol, 2-methyl-6-methylen-; 4,6-Octadien-3-ol, 3,7-dimethyl-; 5-Oxatricyclo[8.2.0.04,6]dodecan, 4,9,12,12-tetramethyl-; 2-Cyclohexen-1- 30 carboxylsäure, 2-ethyl-6,6-dimethyl-, Ethylester; 3-Buten-2-on, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-; 4,7- Methano-1H-inden-5-ol, octahydro-, 5-acetat; Benzoesäure, 2-amino-, Methylester; Spiro[1,3-dioxolan- 2,8’(5’H)-[2H-2,4a]methanonaphthalen], hexahydro-1’,1’,5’,5’-tetramethyl-, (2’S,4’aS,8’aS)- (9Cl); Spiro[1,3-dioxolan-2,8’(5’H)-[2H-2,4a]methanonaphthalen], hexahydro-1’,1’,5’,5’-tetramethyl-; 3-Buten-2-on, 4-(2,6,6-trimethyl-2- cyclohexen-1-yl)-, (3E)-; Benzenethanol, α,α-dimethyl-, 1-acetat; 4,7-Methano-1H-inden-5-ol, 3a,4,5,6,7,7a-hexa- 35 hydro-, 5-acetat; 6-Octen-1-ol, 3,7-dimethyl-, 1-acetat; 2H-Pyran, tetrahydro-2-methyl-4-methylen-6-phenyl-; Bicy- clo[3.3.1]nonan, 2-ethoxy-2,6,6-trimethyl-9-methylen-; 2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)-; Bicyclo[7.2.0]undec- 4-en, 4,11,11-trimethyl-8-methylen-, (1 R,4E,9S)-; 1H-3a,7-Methanoazulen, octahydro-6-methoxy-3,6,8,8-tetramethyl-, (3R,3aS,6S,7R,8aS)-; Bicyclo[7.2.0]undec-4-en, 4,11,11-trimethyl-8-methylen-, (1 R,4E,9S)-; 1H-lnden-1-on, 2,3-dihydro-2,3,3-trimethyl-;2-Propanol, 1,1’-oxybis-;2-Octanol, 7-methoxy-3,7-dimethyl-; 4,9-Decadienal, 4,8-di- 40 methyl-; Benzoesäure; 3-Hexensäure, (3Z)-3-hexen-1-ylester, (3Z)-; Bicyclo[2.2.1]hept-5-en-2-carboxylsäure, 3-(1- methylethyl)-, Ethylester, (1 R,2S,3S,4S)-rel-; 2-Propen-1-ol, 3-phenyl-; Propansäure, 2-methyl-, 1-ethenyl-1,5-dimethyl-4-hexen-1-ylester; Ethanol, 2-phenoxy-, 1-propanoat; 2-Propensäure, 3-phenyl-, Methylester; Benzenpro- panal, 2-ethyl-α,α-dimethyl-; Propansäure, decylester; Benzen, 1,2-dimethoxy-4-(1-propen-1-yl)-; 3-Decen-5-ol, 4- methyl-; Phenol, 2-methoxy-4-(2-propen-1-yl)-; 1-Propanon, 1-[2-methyl-5-(1-methylethyl)-2-cyclohexen-1-yl]-; 1,3- 45 Benzodioxol-5-carboxaldehyd; 2-Dodecenal; 2-Dodecenal, (2E)-; Benzenpropanal, 4-methoxy- α-methyl-; 1,4-Cyc- lohexandicarboxylsäure, 1,4-dimethylester; 2-Buten-1-on, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-; 2-Butanon, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 2-Propennitril, 3-phenyl-, (2E)-; Propansäure, 2-methyl-, 2-phenylethylester; 2-Cyclopenten-1-on, 3-methyl-2-(2Z)-2-penten-1-yl-; Acetaldehyd, 2-[(3,7-dimethyl-6-octen-1-yl)oxy]-; 1-Cyclohe- xen-1-ethanol, 4-(1-methylethyl)-, 1-formiat; 2,4-Decadiensäure, Ethylester, (2E,4Z)-; 2-Propen-1-ol, 3-phenyl-, 1- 50 acetat; Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-; Benzenpropanal, 4-(1,1- dimethylethyl)-; Naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-; 1,4-Methanonaphthalen-5(1H)-on, 4,4a,6,7,8,8a-hexahydro-; Dodecansäure, 12-hydroxy-, λ-lacton (6Cl,7Cl); 1,12-; Cyclohexanpropansäure, 2-propen-1-ylester; 2(3H)-Furanon, 5-hexyldihydro-5-methyl-; 2,6-Nonadienenitril, 3,7-dimethyl-; 10-Undecensäure, Ethylester; Benzenpropanal, α-methyl-4-(1-methylethyl)-; 1-Oxaspiro[4.5]decan-2-on, 8-methyl-; 2(3H)-Furanon, 55 dihydro-5-pentyl-; 2(3H)-Furanon, 5-hexyldihydro-; 2-Buten-1-on, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (2E)-; 2- Buten-1-on, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-, (2E)-; 2H-Pyran-2-on, tetrahydro-6-pentyl-; Benzenpropanal, 4- ethyl-α,α-dimethyl-; 1,3-Benzodioxol, 5-(diethoxymethyl)-; 4-Penten-1-on, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-; Bi- cyclo[3.1.1]hept-2-en-2-ethanol, 6,6-dimethyl-, 2-acetat; 2-Propensäure, 3-phenyl-, Ethylester; 1,3-Dioxan, 2,4,6-

52 EP 2 961 374 B1

trimethyl-4-phenyl-; Cyclododecan, (methoxymethoxy)-; Bicyclo[3.1.1]hept-2-en-2-propanal, α,α,6,6-tetramethyl-; Benzenacetonitril, 4-(1,1-dimethylethyl)-; 2-Buten-1-on, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 1,4-Methanonaph- thalen-6(2H)-on, octahydro-7-methyl-; Bicyclo[3.2.1]octan-8-on, 1,5-dimethyl-, oxim; Benzenpentanol,γ -methyl-; Cyclohexen, 4-(1,5-dimethyl-4-hexen-1-yliden)-1-methyl-; Phenol, 2-methoxy-4-propyl-; Benzoesäure, 2-hydroxy-, 5 2-methylpropylester; 2H-1-Benzopyran-2-on, octahydro-;Cyclohexanon, 2-(1-mercapto-1-methylethyl)-5-methyl-; 2-Oxirancarboxylsäure, 3-methyl-3-phenyl-, Ethylester; 3-Cyclohexen-1-carboxaldehyd, 4-(4-methyl-3-penten-1- yl)-; Propansäure, 2-methyl-, 2-phenoxyethylester; Indeno[1,2-d]-1,3-dioxin, 4,4a,5,9b-tetrahydro-; 2H-Pyran-4-ol, tetrahydro-4-methyl-2-(2-methylpropyl)-; Cyclohexanbutanal, α,2,6,6-tetramethyl-; 1,6-Nonadien-3-ol, 3,7-dimethyl-; 3-Buten-2-on, 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-; Phenol, 2-methoxy-4-(1-propen-1-yl)-; 10 2(3H)-Furanon, 5-hexyldihydro-4-methyl-; 1-Penten-3-on, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; 2-Buten-1-on, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-; 2-Cyclopenten-1-on, 2-hydroxy-3-methyl-; Propansäure, 2,2-dimethyl-, 2-phenylethylester; Dodecannitril; 6-Octen-1-ol, 3,7-dimethyl-, 1-propanoat; Benzenepentanal,β -methyl-; Essig- säure, 2-phenoxy-, 2-propen-1-ylester; Benzenpropanal, 4-(1,1-dimethylethyl)-α-methyl-; 4,7-Methano-1H-inden- 2-carboxaldehyd, octahydro-5-methoxy-; Pentitol, 1,5-anhydro-2,4-dideoxy-2-pentyl-, 3-acetat; Cyclododecan, 15 (ethoxymethoxy)-; 3-Buten-2-on, 4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-; Quinolin, 6-(1-methylpropyl)-; Kohlen- säure, 4-cycloocten-1-yl methylester; 1H-Inden-5-propanal, 2,3-dihydro-3,3-dimethyl-; Ethanon, 1-(3-methyl-2- benzofuranyl)-; 3-Cyclohexen-1-carboxaldehyd, 1-methyl-3-(4-methyl-3-penten-1-yl)-; 6-Oxabicyclo[3.2.1]octan, 5- methyl-1-(2,2,3-trimethyl-3-cyclopenten-1-yl)-; 2H-Pyran-2-on, tetrahydro-6-(3-penten-1-yl)-; 2,4,7-Decatriensäure, Ethylester; Butansäure, 3-methyl-, 2-phenylethylester; Spiro[1,4-methanonaphthalen-2(1H),2’-oxiran], 20 3,4,4a,5,8,8a-hexahydro-3’,7-dimethyl-; Ethanol, 2-[[(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]oxy]-, rel-; Phenol, 2-methoxy-4-(1-propen-1-yl)-, 1-acetat; 2H-lndeno[4,5-b]furan, decahydro-2,2,6,6,7,8,8-heptamethyl-; Es- sigsäure, 2-(cyclohexyloxy)-, 2-propen-1-ylester; Octanal, 7-hydroxy-3,7-dimethyl-; Naphtho[2,1-b]furan, 9b-ethyldodecahydro-3a,7,7-trimethyl-; 1,6-Heptadien-3-on, 2-cyclohexyl-; 5-Thiazolethanol, 4-methyl-; 1-Penten-3-on, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; 3-Buten-2-on, 3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-; 1,4-Cyclohe- 25 xandicarboxylsäure, 1,4-diethylester; 2(3H)-Furanon, 5-heptyldihydro-; 1,3-Benzodioxol-5-propanal, α-methyl-; 4H- Inden-4-on, 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-; Cyclohexanon, 4-(1-ethoxyethenyl)-3,3,5,5-tetramethyl-;Benzenpropannitril, α-ethenyl-α-methyl-; 9-Undecenal, 2,6,10-trimethyl-; Pyridin, 2-(3-phenylpropyl)-; Inde- no[1,2-d]-1,3-dioxin, 4,4a,5,9b-tetrahydro-2,4-dimethyl-;Propansäure, 2-methyl-, 3a,4,5,6,7,7a-hexahydro-4,7-methano-1H-inden-5-ylester; 1-Naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-2,4a,5,8a-tetramethyl-, 1-formiat; Benzen- 30 propanol, β,β,3-trimethyl-; 2-Cyclohexen-1-on, 4-(2-buten-1-yliden)-3,5,5-trimethyl-; 3-Hexen-1-ol, 1-benzoat, (3Z)-; Benzaldehyd, 4-hydroxy-3-methoxy-; 1H-3a,7-Methanoazulen-6-ol, octahydro-3,6,8,8-tetramethyl-, 6-acetat, (3R,3aS,6R,7R,8aS)-; 4,7-Methano-1H-inden-6-ol, 3a,4,5,6,7,7a-hexahydro-8,8-dimethyl-, 6-propanoat; 2-Oxiran- carboxylsäure, 3-phenyl-, Ethylester; 4H-4a,9-Methanoazuleno[5,6-d]-1,3-dioxol, octahydro-2,2,5,8,8,9a-hexamethyl-, (4aR,5R,7aS,9R)-; Butansäure, 1,1-dimethyl-2-phenylethylester; Cyclododeca[c]furan, 35 1,3,3a,4,5,6,7,8,9,10,11,13a-dodecahydro-; Benzenbutannitril, α,α,γ-trimethyl-; 2-Butanon, 4-(1,3-benzodioxol-5- yl)-; Benzoesäure, 4-hydroxy-3-methoxy-, Methylester; 3-Cyclopenten-1-butanol,β ,2,2,3-tetramethyl-2-methyl- 4-(2,2,3-trimethyl-3-cyclopenten-1-yl)butanol; 2-Butenal, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-; 2-Naph- thalenol, decahydro-2,5,5-trimethyl-;1,7-Octandiol, 3,7-dimethyl-; 2H-1-Benzopyran-2-on; 1,3-Dioxolan, 2-[6-methyl-8-(1-methylethyl)bicyclo[2.2.2]oct-5-en-2-yl]-; Propansäure, 2,2-dimethyl-, 3a,4,5,6,7,7a-hexahydro-4,7-me- 40 thano-1H-inden-6-ylester; Butansäure, (2E)-3,7-dimethyl-2,6-octadien-1-ylester; 2-Butanon, 4-(4-hydroxyphenyl)-; 10-Undecensäure, butylester; und Kombinationen davon.

4. Zusammensetzung nach Anspruch 1, wobei das flüchtige Duftstoffmaterial ausgewählt ist aus der Gruppe bestehend aus: 45 (i) einem hochflüchtigen Duftstoffmaterial, das einen Dampfdruck von > 13 Pa (0,1 Torr) bei 25 °C aufweist; (ii) einem mäßig flüchtigen Duftstoffmaterial, das einen Dampfdruck im Bereich von 13 Pa (0,1 Torr) bei 25 °C bis 0,133 Pa (0,001 Torr) bei 25 °C aufweist; und (iii) Kombinationen davon. 50 5. Zusammensetzung nach Anspruch 1, welche ferner Ethanol mit einer Menge von 50 Gew.-% bis 80 Gew.-% oder von 55 Gew.-% bis 75 Gew.-% im Verhältnis zum Gesamtgewicht der Zusammensetzung umfasst.

6. Zusammensetzung nach Anspruch 1, die ferner ein oder mehrere geruchlose Duftstoff-Co-Modulatoren umfasst, 55 vorzugsweise ausgewählt aus der Gruppe bestehend aus:

(i) Isocetyl-Alkohol; (ii) PPG-3-Myristylether;

53 EP 2 961 374 B1

(iii) Neopentylgycoldiethylhexanoat; und (iv) Mischungen davon, vorzugsweise mit Isocetyl-Alkohol.

wobei die ein oder mehreren geruchlosen Duftstoff-Co-Modulatoren mit einer Menge von 0,05 Gew.-% bis 10 Gew.- 5 %,vorzugsweise von 0,5 Gew.-%bis 6 Gew.-%im Verhältnis zum Gesamtgewicht derZusammensetzung vorhanden sind.

7. Zusammensetzung nach Anspruch 8, wobei die geruchlosen Duftstoff-Modulatoren aus wenigstens 50 Gew.-% eines geruchlosen Duftstoff-Modulators im Verhältnis zum kombinierten Gewicht der geruchlosen Duftstoff-Modu- 10 latoren und der geruchlosen Duftstoff-Co-Modulatoren gebildet sind.

8. Zusammensetzung nach Anspruch 1, welche ferner ein oder mehrere geruchlose Duftstoff-Co-Modulatoren umfasst, ausgewählt aus der Gruppe bestehend aus Isocetyl-Alkohol, PPG-3 Myristylether, Neopentyl-Glycol-Diethylhexa- noat oder einer Mischung davon, vorzugsweise in der Menge von ab 0,5 Gew.-% bis 6 Gew.-% im Verhältnis zum 15 Gesamtgewicht der Zusammensetzung.

9. Verfahren zur Verbesserung des Duftstoffprofils einer Zusammensetzung, vorzugsweise zur Steigerung der Per- sistenz eines Aromas, vorzugsweise eines blumigen Aromas, einer Zusammensetzung, welches das in-Berührung- bringen oder Mischen wenigstens eines geruchlosen Duftstoff-Modulators mit wenigstens einem niederflüchtigen 20 Duftstoffmaterial gemäß einer Zusammensetzung, wie in vorstehenden Ansprüchen beschrieben, umfasst.

10. Verfahren nach Anspruch 9, wobei das blumige Aroma ausgewählt ist aus der Gruppe bestehend aus einer laven- delartigen Note, einer rosenartigen Note, einer maiglöckenartigen Note, einer muguetartigen Note, einer jasminar- tigen Note, einer magnolienartigen Note, einer alpenveilchenartigen Note, einer hyazinthenartigen Note, einer flie- 25 derartigen Note, einer orangenblütenartigen Note, einer kirschblütenartigen Note, einer pfingstrosenartigen Note, einer lotosartigen Note, einer lindenblütenartigen Note, einer duftblütenartigen Note, einer fliederartigen Note, einer vanilleblumenartigen Note, einer veilchenartigen Note, einer Florentiner Schwertlilie-artigen Note, einer tiaréblüten- artigen Note und Kombinationen davon.

30 11. Verfahren zur Herstellung eines Endprodukts, welches das in-Berührungbringen mit oder das Mischen-in-das-Pro- dukt einer organoleptisch wirksamen Menge einer Duftstoff-Zusammensetzung nach einem der Ansprüche 1-8 umfasst.

12. Parfümierendes Endprodukt oder Gegenstand, das bzw. der eine Duftstoff-Zusammensetzung nach einem der 35 Ansprüche 1-8 umfasst, wobei das parfümierende Endprodukt ausgewählt ist aus der Gruppe bestehend aus einem Stoffpflegeprodukt, einem Luftpflegeprodukt oder einem Hauspflegeprodukt.

13. Verfahren zur Veränderung oder Verbesserung der Geruchseigenschaften einer Körperoberfläche, welche das in- Berührung-bringen mit oder das Behandeln der Körperoberfläche mit einer Zusammensetzung nach einem der 40 Ansprüche 1-8 umfasst.

Revendications

45 1. Composition comprenant :

(i) un composant de parfum présent en une quantité de 1 % en poids à 30 % en poids, de préférence moins de 25 % en poids, de préférence moins de 20 % en poids, de préférence moins de 15 % en poids, de préférence moins de 10 % en poids ou de préférence moins de 8 % en poids, par rapport au poids total de la composition ; 50 et dans laquelle :

(a) le composant de parfum comprend au moins un matériau de parfum faiblement volatil possédant une pression de vapeur < 0,133 Pa (0,001 Torr) à 25 °C ; (b) le matériau de parfum faiblement volatil est présent en une quantité de 0,1 % en poids à 30 % en poids, 55 de préférence moins de 25 % en poids, de préférence moins de 20 % en poids, ou de préférence moins de 12 % en poids, par rapport au poids total du composant de parfum ; (c) le composant de parfum comprenant en outre un ou plusieurs matériaux de parfum volatils possédant une pression de vapeur ≥ 0,133 Pa (0,001 Torr) à 25 °C ; et

54 EP 2 961 374 B1

(d) le matériau de parfum volatil est présent en une quantité de 70 % en poids à 99,9 % en poids, de préférence plus de 80 % en poids, ou le plus préférablement plus de 88 %, par rapport au poids total du composant de parfum ; et

5 (ii) au moins un modulateur de parfum non odoriférant formé d’un glucoside alcoxylé choisi dans le groupe constitué de méthyl glucoside polyol, éthyl glucoside polyol et propyl glucoside polyol, de préférence PPG-10 Méthyl Glucose Éther, PPG-20 Méthyl Glucose Éther, Méthyl Glucose Éther éthoxylé, Caprylyl/Capryl Gluco- side, Undécyl Glucoside, ou des combinaisons de ceux-ci, en une quantité de 0,1 % en poids à 20 % en poids, de préférence 0,5 % en poids à 18 % en poids, ou plus préférablement 2,5 % en poids à 15 %, par rapport au 10 poids total de la composition.

2. Composition selon la revendication 1, dans laquelle le matériau de parfum faiblement volatil est choisi dans le groupe constitué de : 2-butén-1-ol, 2-méthyl-4-(2,2,3-triméthyl-3-cyclopentén-1-yl)- ; éthanone, 1-(2-naphtalényl)- ; 3-décanone, 1-hydroxy- ; cyclopropaneméthanol, 1-méthyl-2- [(1,2,2-triméthylbicyclo[3.1.0]hex-3-yl)méthyl]- ; ben- 15 zaldéhyde, 3-éthoxy-4-hydroxy- ; 2H-1,5-benzodioxépin-3(4H)-one, 7-méthyl- ; 2-butanol, 1-[[2-(1,1- diméthyléthyl)cyclohexyl]oxy]- ; spiro[5.5]undéc-8-én-1-one, 2,2,7,9-tétraméthyl- ; acide cyclopentane-acétique, 3- oxo-2-pentyl-, ester méthylique, (1 R,2R)-rel- ; acide cyclopentane-acétique, 3-oxo-2-pentyl-, ester méthylique ; octanal, 2-(phénylméthylène)- ; acide cyclopentane-carboxylique, 2-hexyl-3-oxo-, ester méthylique ; 3-cyclopentè- ne-1-butanol, α,β,2,2,3-pentaméthyl- ; cyclopentanone, 2-(3,7-diméthyl-2,6-octadién-1-yl)- ; 1,6,10-dodécatrién-3- 20 ol, 3,7,11-triméthyl- ; 2-pentènenitrile, 3-méthyl-5-phényl-, (2Z)- ; benzènepropanenitrile, 4-éthyl-α,α-diméthyl- ; 1 H-3a,7-méthanoazulén-6-ol, octahydro-3,6,8,8-tétraméthyl-, (3R,3aS,6R,7R,8aS)- ; éthanone, 1-(1,2,3,4,5,6,7,8- octahydro-2,3,8,8-tétraméthyl-2-naphtalényl)- ; acide propanoïque, 2-méthyl-, ester 4-formyl-2- méthoxyphénylique ; 1,6-heptadién-3-one, 1-(2,6,6-triméthyl-2-cyclohexén-1-yl)- ; acide benzoïque, 2-hydroxy-, ester hexylique ; acide benzoïque, ester phénylique ; cyclohexanepropanol, 2,2,6-triméthyl-α-propyl-, (1 R,6S)- ; cy- 25 clohexanepropanol, 2,2,6-triméthyl-α-propyl- ; acide benzoïque, 2-hydroxy-, ester 3-méthyl-2-butén-1-ylique ; 2H- 1,5-benzodioxépin-3(4H)-one, 7-(1-méthyléthyl)- ; butanal, 4-(octahydro-4,7-méthano-5H-indén-5-ylidène)- ; cyclopenta[g]-2-benzopyran, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexaméthyl- ; cyclopentanone, 2-[2-(4-méthyl-3-cyclo- hexén-1-yl)propyl]- ; 2(3H)-naphtalénone, 4,4a,5,6,7,8-hexahydro-4,4a-diméthyl-6-(l-méthyléthényl)-, (4R,4aS,6R)- ; acide 2-propénoïque, 3-phényl-, ester pentylique ; 4H-pyran-4-one, 3-hydroxy-2-méthyl-; 1-propanol, 30 2-méthyl-3-[(1,7,7-triméthylbicyclo[2.2.1]hept-2-yl)oxy]- ; 1-naphtalénol, 1,2,3,4,4a,5,8,8a-octahydro-2,2,6,8- tétraméthyl- ; acide 2-buténoïque, 2-méthyl-, ester (2E)-3,7-diméthyl-2,6-octadién-1-ylique, (2E)- ; 1,3-dioxane, 2-(2,4-diméthyl-3-cyclohexén-1-yl)-5-méthyl-5-(1-méthylpropyl)- ; nonadécane ; 4-pentén-2-ol, 3-méthyl-5-(2,2,3- triméthyl-3-cyclopentén-1-yl)- ; acide propanoïque, 2-méthyl-, ester 2-méthyl-4-oxo-4H-pyran-3-ylique ; 2-butén-1- ol, 2-éthyl-4-(2,2,3-triméthyl-3-cyclopentén-1-yl)- ; 1,6-méthanonaphtalén-1 (2H)-ol, octahydro-4,8a,9,9-tétramé- 35 thyl-, (1 R,4S,4aS,6R,8aS)- ; 2H-1,5-benzodioxépin-3(4H)-one, 7-(1,1-diméthyléthyl)- ; acide benzoïque, ester phénylméthylique ; 8-cyclohexadécén-1-one ; acide benzoïque, 2-hydroxy-, ester (3Z)-3-hexén-1-ylique ; 4H-pyran- 4-one, 2-éthyl-3-hydroxy- ; cyclopentadécanone, 3-méthyl- ; acide benzoïque, 2-hydroxy-, ester phénylméthylique ; 6,8-nonadién-3-one, 2,4,4,7-tétraméthyl-, oxime ; acide benzoïque, 2-hydroxy-, ester cyclohexylique ; benzène, [2-(diméthoxyméthyl)-1-heptén-1-yl]- ; 3-cyclopentène-1-butanol, β,2,2,3-tétraméthyl-δ-méthylène- ; 4-pentén-1- 40 one, 1-spiro[4.5]déc-7-én-7-yl- ; acide acétique, 2-(1-oxopropoxy)-, ester 1-(3,3-diméthylcyclohexyl)éthylique ; 2- pentén-1-ol, 5-[(1R,3R,6S)-2,3-diméthyltricyclo[2.2.1.02,6]hept-3-yl]-2-méthyl-, (2Z)- ; 4-pentén-2-ol, 3,3-diméthyl- 5-(2,2,3-triméthyl-3-cyclopentén-1-yl)- ; 5,8-méthano-2H-1-benzopyran-2-one, 6-éthylidèneoctahydro- ; 4-cyclo- pentadécén-1-one, (4Z)- ; éthanone, 1-[(3R,3aR,7R,8aS)-2,3,4,7,8,8a-hexahydro-3,6,8,8-tétraméthyl-1H-3a,7-mé- thanoazulén-5-yl]- ; 1,3-dioxolane, 2,4-diméthyl-2-(5,6,7,8-tétrahydro-5,5,8,8-tétraméthyl-2-naphtalényl)- ; oxacy- 45 clohexadécan-2-one ; 1-propanol, 2-[1-(3,3-diméthylcyclohexyl)éthoxy]-2-méthyl-, 1-propanoate ; 5-cyclopentadé- cén-1-one, 3-méthyl- ; 2-pentén-1-ol, 2-méthyl-5-[(1S,2R,4R)-2-méthyl-3-méthylènebicyclo[2.2.1]hept-2-yl]-, (2Z)- ; 2H-1,5-benzodioxépin-3(4H)-one, 7-(3-méthylbutyl)- ; éthanone, 1-(2,6,10-triméthyl-2,5,9-cyclododecatrién-1-yl)- ; 1H-3a,6-méthanoazulène-3-méthanol, octahydro-7,7-diméthyl-8-méthylène-, (3S,3aR,6R,8aS)- ; benzèneacetoni- trile, α-cyclohexylidène- ; acide benzoïque, 2-[(2-méthylpentylidène)amino]-, ester méthylique ; acide benzoïque, 50 ester 2-phényléthylique ; 5-cyclohexadécén-1-one ; cyclohexanol, 4-(1,7,7-triméthylbicyclo[2.2.1]hept-2-yl)- ; 3-cy- clohexène-1-carboxaldéhyde, 4-(4-hydroxy-4-méthylpentyl)- ; éthanone, 1-(5,6,7,8-tétrahydro-3,5,5,6,8,8-hexamé- thyl-2-naphtalényl)- ; éthanone, 1-(5,6,7,8-tétrahydro-3,5,5,6,8,8-hexaméthyl-2- ; 2-cyclopentadécén-1-one, 3- méthyl- ; oxacycloheptadécan-2-one ; acide benzène-acétique, ester 4-méthylphénylique ; acide benzène-acétique, ester 2-phényléthylique ; cyclododécane-éthanol,β-méthyl- ; acide 2-propénoïque, 3-phényl-, ester 55 phénylméthylique ; acide benzoïque, 2,4-dihydroxy-3,6-diméthyl-, ester méthylique ; naphto[2,1-b]furan-6(7H)-one, 8,9-dihydro-1,5,8-triméthyl-, (8R)-; acide benzène-acétique, ester (4-méthoxyphényl)méthylique ; benzène, 2-mé- thoxy-1-(phénylméthoxy)-4-(1-propén-1-yl)- ; acide benzène-acétique, ester (2E)-3,7-diméthyl-2,6-octadién-1- ylique ; oxacyclohexadéc-12-én-2-one, (12E)- ; acide benzoïque, 2-hydroxy-, ester 2-phényléthylique ; acide 2-

55 EP 2 961 374 B1

propénoïque, 3-phényl-, ester 1-éthényl-1,5-diméthyl-4-hexén-1-ylique ; oxacycloheptadéc-10-én-2-one ; oxacyclo- heptadéc-8-en-2-one, (8Z)- ; 1,7-dioxacycloheptadécan-8-one ; 7-octén-2-ol, 8-(1H-indol-1-yl)-2,6-diméthyl- ; 1,4- dioxacyclohexadécane-5,16-dione ; 1,4-dioxacycloheptadécane-5,17-dione ; phénol, 4-[3-(benzoyloxy)-1-propén- 1-yl]-2-méthoxy- ; acide benzoïque, 2-[(1-hydroxy-3-phénylbutyl)amino]-, ester méthylique ; et des combinaisons 5 de ceux-ci.

3. Composition selon la revendication 1, dans laquelle le matériau de parfum volatil est choisi dans le groupe constitué de : acide formique, ester méthylique ; méthane, 1,1’-thiobis- ; acide acétique ester éthylique ; acide propanoïque, ester éthylique ; acide acétique, ester 2-méthylpropylique ; acide butanoïque, ester éthylique ; 1-butanol ; acide 10 butanoïque, 2-méthyl-, ester éthylique ; 1-butanol, 3-méthyl-, 1-acétate ; acide butanoïque, 2-méthyl-, ester 1- méthyléthylique ; 2-heptanone ; 2-hexénal, (2E)- ; 1-butanol, 3-méthyl- ; 2-butén-1-ol, 3-méthyl-, 1-acétate ; 1,3- dioxolane-2-méthanamine, N-méthyl- ; bicyclo[3.1.1]hept-2-ène, 2,6,6-triméthyl-, (1R,5R)- ; bicyclo[2.2.1]heptane, 2,2-diméthyl-3-méthylène- ; 2-butanethiol, 4-méthoxy-2-méthyl- ; acide pentanoïque, 2-méthyl-, ester éthylique ; bicyclo[3.1.0]hexane, 4-méthylène-1-(1-méthyléthyl)-; bicyclo[3.1.1]heptane, 6,6-diméthyl-2-méthylène- ; 1-buta- 15 nol, 3-méthyl-, 1-propanoate ; 1,6-octadiène,7-méthyl-3-méthylène- ;octanal ;2H-pyran, 2-éthényltétrahydro-2,6,6- triméthyl- ; 2-octanone ; acide hexanoïque, ester éthylique ; 2-oxabicyclo[2.2.2]octane, 1,3,3-triméthyl- ; benzène, 1-méthyl-4-(1-méthyléthyl)- ; benzène, 1-méthoxy-4-méthyl- ; 1,3,6-octatriène, 3,7-diméthyl- ; cyclohexène, 1-mé- thyl-4-(1-méthyléthényl)- ; cyclohexène, 1-méthyl-4-(1-méthyléthényl)-, (4R)- ; 3-octanone ; undécanal, 2-méthyl- ; acide acétique, ester hexylique ; 5-heptén-2-one, 6-méthyl- ; 2-heptén-4-one, 5-méthyl- ; 3-hexén-1-ol, 1-acétate, 20 (3Z)- ; 3-hexén-1-ol, 1-acétate ; acide propanoïque, 2-hydroxy-, ester éthylique ; acide butanoïque, ester 2- méthylbutylique ; acide butanoïque, ester 3-méthylbutylique ; 1,4-cyclohexadiène, 1-méthyl-4-(1-méthyléthyl)- ; thiazole, 2-(2-méthylpropyl)- ; 3-hexén-1-ol, (3Z)- ; benzaldéhyde ; acide butanoïque, 3-oxo-, ester éthylique ; 2- hexén-1-ol, (2E)- ; 2-hexén-1-ol, (2Z)- ; cyclohexane, 3-éthoxy-1,1,5-triméthyl-, cis- (9CI) ; 2-pentanone, 4-mercapto-4-méthyl- ; 2,4,6-octatriène, 2,6-diméthyl-, (4E,6E)- ; oxirane, 2,2-diméthyl-3-(3-méthyl-2,4-pentadién-1-yl)- ; 25 4,7-acide octadiénoïque, ester méthylique, (4E)- ; acide carbonique, ester (3Z)-3-hexén-1-yl-méthylique ; acide hexanoïque, ester 2-propén-1-ylique ; 5-hepténal, 2,6-diméthyl- ; acide heptanoïque, ester éthylique ; 3-cyclohexè- ne-1-carboxaldéhyde, 2,4-diméthyl- ; benzène, (2,2-diméthoxyéthyl)-; 2H-pyran, tétrahydro-4-méthyl-2-(2-méthyl- 1-propén-1-yl)- ; 3-nonanone ; benzonitrile ; 3-octanol ; 1-hexanol, 3,5,5-triméthyl-, 1-acétate ; 4-heptanol, 2,6-di- méthyl-, 4-acétate ; acide hexanoïque, ester 2-méthylpropylique ; acide propanoïque, 2-méthyl-, ester hexylique ; 30 acide cyclohexanecarboxylique, 1,4-diméthyl-, ester méthylique, trans- ; benzèneacetaldéhyde ; acide butanoïque, 3-hydroxy-, ester éthylique ; acide propanedioïque, ester 1,3-diéthylique ; acide benzoïque, ester méthylique ; 1,3,5- undecatriène ; 4-décénal, (4E)- ; 1,3-dioxane, 2-butyl-4,4,6-triméthyl- ; 2-heptanol, 2,6-diméthyl- ; éthanone, 1-phé- nyl-; benzèneacétaldéhyde, α-méthyl- ; acide propanoïque, 2-méthyl-, ester 1,3-diméthyl-3-butén-1-ylique ; 2,6- nonadiénal, (2E,6Z)- ; pyrazine, 2-méthoxy-3-(2-méthylpropyl)- ; acide formique, ester phénylméthylique ; benzène, 35 1-méthoxy-4-propyl- ; cyclohexanone, 5-méthyl-2-(1-méthyléthyl)-, (2R,5R)-rel- ; cyclohexanone, 5-méthyl-2-(1- méthyléthyl)-, (2R,5S)-rel- ; 2-nonénal ; cyclohexanone, 2-éthyl-4,4-diméthyl- ; benzène, 1,4-diméthoxy- ; benzène, 1-(éthoxyméthyl)-2-méthoxy- ; bicyclo[2.2.1]heptan-2-one, 1,7,7-triméthyl- ; 2-hexène, 6,6-diméthoxy-2,5,5- triméthyl- ; décanal ; benzènepropanal, β-méthyl- ; benzèneméthanol, α-méthyl-, 1-acétate ; acide acétique, ester nonylique ; éthanone, 1-(4-méthylphényl)- ; 2H-pyran, 6-butyl-3,6-dihydro-2,4-diméthyl- ; acide propanoïque, 2-mé- 40 thyl-, ester (3Z)-3-hexén-1-ylique ; acide benzoïque, ester éthylique ; 3-octanol, 3,7-diméthyl-, 3-acétate ; 1-hexanol, 5-méthyl-2-(1-méthyléthyl)-, 1-acétate ; cyclohexanol, 3,3,5-triméthyl-, (1R,5R)-rel- ; 2-hexénal, 5-méthyl-2-(1- méthyléthyl)- ; 7-octén-2-ol, 2,6-diméthyl- ; acide acétique, ester phénylméthylique ; cyclohexanone, 2-(1- méthylpropyl)- ; 3-octén-1-ol, (3Z)- ; acide heptanoïque, ester 2-propén-1-ylique ; benzèneméthanol ; acide buta- noïque, 2-méthyl-, ester hexylique ; 2(3H)-furanone, 5-éthyldihydro- ; cyclohexane-éthanol, 1-acétate ; acide 2- 45 nonénoïque, ester méthylique ; acide butanoïque, ester (3Z)-3-hexén-1-ylique ; acide 2-octynoïque, ester méthylique ; 1,3-oxathiane, 2-méthyl-4-propyl-, (2R,4S)-rel- ; heptanal, 6-méthoxy-2,6-diméthyl- ; bicyclo[2.2.1]heptan-2-ol, 1,3,3-triméthyl-, 2-acétate ; 1,6-octadién-3-ol, 3,7-diméthyl-, 3-acétate ; 2-octanol, 2,6-diméthyl- ; 1- octanol ; 3-cyclohexène-1-méthanethiol, α,α,4-triméthyl- ;cyclohexaneméthanol, α,α,4-triméthyl-, 1-acétate ; cyclohexanol, 2-(1,1-diméthyléthyl)-, 1-acétate ; cyclohexanol, 4-(1,1-diméthyléthyl)-, 1-acétate ; pyrazine, 2-méthoxy- 50 3-(1-méthylpropyl)- ;cyclohexanol, 5-méthyl-2-(1-méthyléthényl)-,(1 R,2S,5R)- ; 2-undécanone ;benzènepropanol, α,α-diméthyl- ; bicyclo[2.2.1]heptan-2-ol, 1,7,7-triméthyl-, 2-acétate, (1R,2R,4R)-rel- ; 1,6-octadién-3-ol, 3,7- diméthyl- ; acide benzène-acétique, ester éthylique ; benzène-éthanol, α,α-diméthyl- ; acide cyclopropanecarboxy- lique, ester (3Z)-3-hexén-1-yl ; 3-cyclohexène-1-méthanol, 3,5-diméthyl-, 1-acétate ; undécanal ; éthanone, 1-(3- cyclooctén-1-yl)- ; cyclohexanone, 4-(1,1-diméthyléthyl)- ; 6-nonén-1-ol, (6Z)- ; benzène, (2-butoxyéthyl)- ; bicy- 55 clo[3.1.1]hept-3-én-2-one, 4,6,6-triméthyl- ; acide cyclohexanecarboxylique, 2,2,6-triméthyl-, ester éthylique, (1R,6S)-rel- ; benzène-éthanol ; 2,6-octadiénal, 3,7-diméthyl-, (2Z)- ; 2,6-octadiénal, 3,7-diméthyl- ; cyclohexanol, 5-méthyl-2-(1-méthyléthyl)-, 1-acétate, (1R,2S,5R)-rel- ; acide benzoïque, 2-hydroxy-, ester méthylique ; benzène, 1-méthoxy-4-(1E)-1-propén-1-yl- ; 2,6-octadiène, 1,1-diméthoxy-3,7-diméthyl- ; cyclohexaneméthanol, α,3,3-trimé-

56 EP 2 961 374 B1

thyl-, 1-formiate ; 2-décénal, (2E)- ; 3-cyclopentène-1-acétonitrile, 2,2,3-triméthyl- ; 2-cyclohexén-1-one, 2-méthyl- 5-(1-méthyléthényl)-, (5R)- ; cyclohexanone, 4-(1,1-diméthylpropyl)- ; 6,10-dioxaspiro[4.5]décane, 8,8-diméthyl- 7-(1-méthyléthyl)- ; 2-cyclohexén-1-one, 3-méthyl-5-propyl- ; benzonitrile, 4-(1-méthyléthyl)- ; 2,6-nonadiènenitrile ; acide butanoïque, 2-méthyl-, ester (3Z)-3-hexén-1-ylique ; benzène, 1-(cyclopropylméthyl)-4-méthoxy- ; acide 2- 5 nonynoïque, ester méthylique ; acide acétique, ester 2-phényléthylique ; cyclohexanol, 2-(1,1-diméthyléthyl)- ; 2,6- nonadién-1-ol ; acide propanoïque, 2-méthyl-, ester phénylméthylique ; bicylo[2.2.1]heptan-2-ol, 1,2,3,3-tétramé- thyl-, (1R,2R,4S)-rel- ; benzaldéhyde, 4-(1-méthyléthyl)- ; 2,5-octadién-4-one, 5,6,7-triméthyl-, (2E)- ; 3-cyclohexén- 1-ol, 4-méthyl-1-(1-méthyléthyl)- ; 3-cyclohexène-1-méthanol, 2,4,6-triméthyl- ; acide pentanoïque, ester (3Z)-3- hexén-1-ylique ; bicyclo[2.2.1]heptan-2-ol, 1,7,7-triméthyl-, 2-propanoate, (1 R,2R,4R)-rel- ; benzène, 1-méthyl- 10 4-(1-méthyléthyl)-2-(1-propén-1-yl)- ; 3-cyclohexène-1-propanal, β,4-diméthyl- ; 1-hexanol, 5-méthyl-2-(1-méthylé- thyl)-, (2R)- ; 3-heptanone, 5-méthyl-, oxime ; 2(3H)-furanone, 5-butyldihydro- ; 1-nonanol ; acide acétique, 2-(3- méthylbutoxy)-, ester2-propén-1-ylique ;bicyclo[2.2.1]heptan-2-ol, 1,7,7-triméthyl-, (1S,2R,4S)- ;bicyclo[2.2.1]heptan-2-ol, 1,7,7-triméthyl-, (1 R,2R,4R)-rel- ; cyclohexanol, 2-(1,1-diméthylpropyl)-, 1-acétate ; 3-cyclohexène-1-mé- thanol, α,α,4-triméthyl-, 1-acétate ; cyclohexaneméthanol, α,α,4-triméthyl- ; 10-undécénal ; acide 2,4-cyclohexa- 15 diène-1-carboxylique, 2,6,6-triméthyl-, ester éthylique ; 1-octanol, 3,7-diméthyl- ; furane, tétrahydro-2,4-diméthyl-4- phényl- ; benzène, [2-(3-méthylbutoxy)éthyl]- ; acide butanoïque, ester phénylméthylique ; acide benzoïque, 2-hydroxy-, ester éthylique ; cyclohexanol, 4-(1,1-diméthyléthyl)- ; 1,6-octadién-3-ol, 3,7-diméthyl-, 3-formiate ; dodécanal ; 3,6-nonadién-1-ol, (3Z,6Z)- ; 3,6-nonadién-1-ol ; décanenitrile ; cyclohexanol, 5-méthyl-2-(1-méthylé- thyl)-, (1 R,2S,5R)- ; acide propanoïque, 2-méthyl-, ester 4-méthylphénylique ; acide propanoïque, 2-méthyl-, ester 20 (1 R,2S,4R)-1,7,7-triméthylbicyclo[2.2.1]hept-2-ylique, rel- ; acétaldéhyde, 2-(4-méthylphenoxy)- ; acide 2-buténoï- que, 2-méthyl-, ester (3Z)-3-hexén-1-ylique, (2E)- ; bicyclo[3.1.1]hept-2-ène-2-propanal, 6,6-diméthyl- ; 2-nonanol, 6,8-diméthyl- ; cyclohexanol, 1-méthyl-3-(2-méthylpropyl)- ; 1H-indole ; 2-undécénal ; 2H-pyran-2-one, 4,6- diméthyl- ; 3-cyclohexène-1-méthanol, α,α,4-triméthyl- ; 3-heptén-2-one, 3,4,5,6,6-pentaméthyl-, (3Z)- ; 2(3H)-furanone, 5-butyldihydro-4-méthyl- ; 7-octén-2-ol, 2,6-diméthyl-, 2-acétate ; 2-propénal, 3-phényl- ; 1,6-octadién-3-ol, 25 3,7-diméthyl-, 3-propanoate ; 1,6-nonadién-3-ol, 3,7-diméthyl-, 3-acétate ; cyclopentanone, 2,2,5-triméthyl-5- pentyl- ; 2,6-octadién-1-ol, 3,7-diméthyl-, 1-acétate, (2Z)- ; 2,6-octadién-1-ol, 3,7-diméthyl-, 1-acétate, (2E)- ; undé- cane, 1,1-diméthoxy-2-méthyl- ; benzèneméthanol, α-méthylène-, 1-acétate ; benzaldéhyde, 4-méthoxy- ; cyclohexanol, 5-méthyl-2-(1-méthyléthényl)-, 1-acétate, (1R,2S,5R)- ; 6-octènenitrile, 3,7-diméthyl- ;6-octén-2-ol, 2,6- diméthyl- ; benzène, 1,1’-oxybis- ; acide benzoïque, ester butylique ; 5,8-méthano-2H-1-benzopyran, 6- 30 éthylidèneoctahydro- ; cyclohexanepropanol, α,α-diméthyl- ; benzènepropanal, β-méthyl-3-(1-méthyléthyl)- ; ben- zèneméthanol, 4-méthoxy-, 1-acétate ; phénol, 2-éthoxy-4-méthyl- ; benzène, [2-(1-propoxyéthoxy)éthyl]- ; 7-octén- 1-ol, 3,7-diméthyl- ; bicyclo[4.3.1]décane, 3-méthoxy-7,7-diméthyl-10-méthylène- ; acide propanoïque, 2-(1,1-dimé- thylpropoxy)-, ester propylique, (2S)- ; acide benzoïque, 2-(méthylamino)-, ester méthylique ; 6-octén-1-ol, 3,7- diméthyl-, (3S)- ; 7-octén-2-ol, 2-méthyl-6-méthylène- ; 4,6-octadién-3-ol, 3,7-diméthyl- ; 5-oxatricy- 35 clo[8.2.0.04,6]dodécane, 4,9,12,12-tétraméthyl- ; acide 2-cyclohexène-1-carboxylique, 2-éthyl-6,6-diméthyl-, ester éthylique ; 3-Butén-2-one, 4-(2,6,6-triméthyl-1-cyclohexén-1-yl)-, (3E)- ; 4,7-méthano-1H-indén-5-ol, octahydro-, 5- acétate ; acide benzoïque, 2-amino-, ester méthylique ; spiro[1,3-dioxolane-2,8’(5’H)-[2H-2,4a]méthanonaphtalè- ne], hexahydro-1’,1’,5’,5’-tétraméthyl-, (2’S,4’aS,8’aS)- (9CI) ; spiro[1,3-dioxolane-2,8’(5’H)-[2H-2,4a]méthano- naphtalène], hexahydro-1’,1’,5’,5’-tétraméthyl- ; 3-butén-2-one, 4-(2,6,6-triméthyl-2-cyclohexén-1-yl)-, (3E)- ; ben- 40 zène-éthanol, α,α-diméthyl-, 1-acétate ; 4,7-méthano-1H-indén-5-ol, 3a,4,5,6,7,7a-hexahydro-, 5-acétate ; 6-octén- 1-ol, 3,7-diméthyl-, 1-acétate ; 2H-pyrane, tétrahydro-2-méthyl-4-méthylène-6-phényl- ; bicyclo[3.3.1]nonane, 2- éthoxy-2,6,6-triméthyl-9-méthylène- ; 2,6-octadién-1-ol, 3,7-diméthyl-, (2E)- ; bicyclo[7.2.0]undéc-4-ène, 4,11,11- triméthyl-8-méthylène-, (1 R,4E,9S)- ; 1H-3a,7-méthanoazulène, octahydro-6-méthoxy-3,6,8,8-tétraméthyl-, (3R,3aS,6S,7R,8aS)- ; bicyclo[7.2.0]undéc-4-ène, 4,11,11-triméthyl-8-méthylène-, (1 R,4E,9S)- ; 1H-indén-1-one, 45 2,3-dihydro-2,3,3-triméthyl- ; 2-propanol, 1,1’-oxybis- ; 2-octanol, 7-méthoxy-3,7-diméthyl- ; 4,9-décadiénal, 4,8- diméthyl- ; acide benzoïque ; acide 3-hexénoïque, ester (3Z)-3-hexén-1-ylique, (3Z)- ; acide bicyclo[2.2.1]hept-5- ène-2-carboxylique, 3-(1-méthyléthyl)-, ester éthylique, (1 R,2S,3S,4S)-rel- ; 2-propén-1-ol, 3-phényl-; acide propa- noïque, 2-méthyl-, ester 1-éthényl-1,5-diméthyl-4-hexén-1-ylique ; éthanol, 2-phénoxy-, 1-propanoate ; acide 2- propénoïque, 3-phényl-, ester méthylique ; benzènepropanal, 2-éthyl-α,α-diméthyl- ; acide propanoïque, ester 50 décylique ; benzène, 1,2-diméthoxy-4-(1-propén-1-yl)- ; 3-décén-5-ol, 4-méthyl- ; phénol, 2-méthoxy-4-(2-propén- 1-yl)- ; 1-propanone, 1-[2-méthyl-5-(1-méthyléthyl)-2-cyclohexén-1-yl]- ; 1,3-benzodioxole-5-carboxaldéhyde ; 2- dodécénal ; 2-dodécénal, (2E)- ; benzènepropanal, 4-méthoxy-α-méthyl- ; acide 1,4-cyclohexanedicarboxylique, ester 1,4-diméthylique ; 2-butén-1-one, 1-(2,6,6-triméthyl-3-cyclohexén-1-yl)- ; 2-butanone, 4-(2,6,6-triméthyl-1-cy- clohexén-1-yl)- ; 2-propènenitrile, 3-phényl-, (2E)- ; acide propanoïque, 2-méthyl-, ester 2-phényléthylique ; 2-cy- 55 clopentén-1-one, 3-méthyl-2-(2Z)-2-pentén-1-yl- ; acétaldéhyde, 2-[(3,7-diméthyl-6-octén-1-yl)oxy]- ; 1-cyclohexè- ne-1-éthanol, 4-(1-méthyléthyl)-, 1-formiate ; acide 2,4-déecadiénoïque, ester éthylique, (2E,4Z)- ; 2-propén-1-ol, 3-phényl-, 1-acétate ; naphto[2,1-b]furane, dodécahydro-3a,6,6,9a-tétraméthyl-, (3aR,5aS,9aS,9bR)- ; benzène- propanal, 4-(1,1-diméthyléthyl)- ; naphto[2,1-b]furane, dodécahydro-3a,6,6,9a-tétraméthyl- ; 1,4-méthanonaphta-

57 EP 2 961 374 B1

lén-5(1H)-one, 4,4a,6,7,8,8a-hexahydro- ; acide dodécanoïque, 12-hydroxy-, λ-lactone (6Cl,7Cl) ; 1,12- ; acide cy- clohexanepropanoïque, ester 2-propén-1-ylique ; 2(3H)-furanone, 5-hexyldihydro-5-méthyl- ; 2,6-nonadiènenitrile, 3,7-diméthyl- ; 10-acide undécénoïque, ester éthylique ; benzènepropanal,α -méthyl-4-(1-méthyléthyl)- ; 1-oxaspiro[4.5]décan-2-one, 8-méthyl- ; 2(3H)-furanone, dihydro-5-pentyl- ; 2(3H)-furanone, 5-hexyldihydro- ; 2-butén-1- 5 one, 1-(2,6,6-triméthyl-2-cyclohexén-1-yl)-, (2E)- ; 2-butén-1-one, 1-(2,4,4-triméthyl-2-cyclohexén-1-yl)-, (2E)- ; 2H- pyran-2-one, tétrahydro-6-pentyl- ; benzènepropanal, α,α-diméthyl- 4-éthyl- ; 1,3-benzodioxole, 5-(diéthoxyméthyl)- ; 4-pentén-1-one, 1-(5,5-diméthyl-1-cyclohexén-1-yl)- ; bicyclo[3.1.1]hept-2-ène-2-éthanol, 6,6- diméthyl-, 2-acétate ; acide 2-propénoïque, 3-phényl-, ester éthylique ; 1,3-dioxane, 2,4,6-triméthyl-4-phényl- ; cy- clododécane, (méthoxyméthoxy)- ; bicyclo[3.1.1]hept-2-ène-2-propanal, α,α,6,6-tétraméthyl- ; benzèneacetonitrile, 10 4-(1,1-diméthyléthyl)-; 2-butén-1-one, 1-(2,6,6-triméthyl-1-cyclohexén-1-yl)- ; 1,4-méthanonaphtalén-6(2H)-one, octahydro-7-méthyl- ; bicyclo[3.2.1]octan-8-one, 1,5-diméthyl-, oxime ; benzènepentanol, γ-méthyl- ; cyclohexène, 4-(1,5-diméthyl-4-hexén-1-ylidène)-1-méthyl- ; phénol, 2-méthoxy-4-propyl- ; acide benzoïque acid, 2-hydroxy-, ester 2-méthylpropylique ; 2H-1-benzopyran-2-one, octahydro- ; cyclohexanone, 2-(1-mercapto-1-méthyléthyl)-5- méthyl- ; acide 2-oxiranecarboxylique, 3-méthyl-3-phényl-, ester éthylique ; 3-cyclohexène-1-carboxaldéhyde, 4-(4- 15 méthyl-3-pentén-1-yl)- ; acide propanoïque, 2-méthyl-, ester 2-phenoxyéthylique ; indéno[1,2-d]-1,3-dioxin, 4,4a,5,9b-tétrahydro- ; 2H-pyran-4-ol, tétrahydro-4-méthyl-2-(2-méthylpropyl)- ; cyclohexanebutanal,α,2,6,6- tétraméthyl- ; 1,6-nonadién-3-ol, 3,7-diméthyl- ; 3-butén-2-one, 4-(2,2,6-triméthyl-7-oxabicyclo[4.1.0]hept-1-yl)- ; phénol, 2-méthoxy-4-(1-propén-1-yl)- ; 2(3H)-furanone, 5-hexyldihydro-4-méthyl- ; 1-pentén-3-one, 1-(2,6,6-trimé- thyl-2-cyclohexén-1-yl)- ; 2-butén-1-one, 1-(2,6,6-triméthyl-1,3-cyclohexadién-1-yl)- ; 2-cyclopentén-1-one, 2-hy- 20 droxy-3-méthyl- ; acide propanoïque, 2,2-diméthyl-, ester 2-phényléthylique ; dodécanenitrile ; 6-octén-1-ol, 3,7- diméthyl-, 1-propanoate ; benzènepentanal, β-méthyl- ; acide acétique, 2-phénoxy-, ester 2-propén-1-ylique ; ben- zènepropanal, 4-(1,1-diméthyléthyl)-α-méthyl- ; 4,7-méthano-1H-indène-2-carboxaldéhyde, octahydro-5- méthoxy- ; pentitol, 1,5-anhydro-2,4-didéoxy-2-pentyl-, 3-acétate ; cyclododécane, (éthoxyméthoxy)- ; 3-butén-2- one,4-(2,5,6,6-tétraméthyl-2-cyclohexén-1-yl)- ;quinoléine, 6-(1-méthylpropyl)- ;acide carbonique, ester4-cyclooc- 25 tén-1-yl méthylique ; 1 H-indène-5-propanal, 2,3-dihydro-3,3-diméthyl- ; éthanone, 1-(3-méthyl-2-benzofuranyl)- ; 3-cyclohexène-1-carboxaldéhyde, 1-méthyl-3-(4-méthyl-3-pentén-1-yl)- ; 6-oxabicyclo[3.2.1]octane, 5-méthyl- 1-(2,2,3-triméthyl-3-cyclopentén-1-yl)- ;2H-pyran-2-one, tétrahydro-6-(3-pentén-1-yl)- ;acide 2,4,7-décatriénoïque, ester éthylique ; acide butanoïque, 3-méthyl-, ester 2-phényléthylique ; spiro[1,4-méthanonaphtalène-2(1H),2’-oxirane], 3,4,4a,5,8,8a-hexahydro-3’,7-diméthyl- ; éthanol, 2-[[(1R,2R,4R)-1,7,7-triméthylbicyclo[2.2.1]hept-2-yl]oxy]-, 30 rel- ; phénol, 2-méthoxy-4-(1-propén-1-yl)-, 1-acétate ; 2H-indéno[4,5-b]furane, décahydro-2,2,6,6,7,8,8- heptaméthyl- ; acide acétique, 2-(cyclohexyloxy)-, ester 2-propén-1-ylique ; octanal, 7-hydroxy-3,7-diméthyl- ; naphto[2,1-b]furane, 9b-éthyldodecahydro-3a,7,7-triméthyl- ; 1,6-heptadién-3-one, 2-cyclohexyl- ; 5-thiazole-étha- nol, 4-méthyl- ; 1-pentén-3-one, 1-(2,6,6-triméthyl-2-cyclohexén-1-yl)- ; 3-butén-2-one, 3-méthyl-4-(2,6,6-triméthyl- 2-cyclohexén-1-yl)- ; acide 1,4-cyclohexanedicarboxylique, ester 1,4-diéthylique ; 2(3H)-furanone, 5- 35 heptyldihydro- ; 1,3-benzodioxole-5-propanal, α-méthyl- ; 4H-indén-4-one, 1,2,3,5,6,7-hexahydro-1,1,2,3,3- pentaméthyl- ; cyclohexanone, 4-(1-éthoxyéthényl)-3,3,5,5-tétraméthyl- ; benzènepropanenitrile, α-éthényl-α-mé- thyl-; 9-undécénal, 2,6,10-triméthyl- ; pyridine, 2-(3-phénylpropyl)- ; indéno[1,2-d]-1,3-dioxine, 4,4a,5,9b-tétrahydro- 2,4-diméthyl- ; acide propanoïque, 2-méthyl-, ester 3a,4,5,6,7,7a-hexahydro-4,7-méthano-1H-indén-5-ylique ; 1- naphtalénol, 1,2,3,4,4a,7,8,8a-octahydro-2,4a,5,8a-tétraméthyl-, 1-formiate ; benzènepropanol, β,β,3-triméthyl- ; 2- 40 cyclohexén-1-one, 4-(2-butén-1-ylidène)-3,5,5-triméthyl- ; 3-hexén-1-ol, 1-benzoate, (3Z)- ; benzaldéhyde, 4-hydroxy-3-méthoxy- ; 1H-3a,7-méthanoazulén-6-ol, octahydro-3,6,8,8-tétraméthyl-, 6-acétate, (3R,3aS,6R,7R,8aS)- ; 4,7-méthano-1H-indén-6-ol, 3a,4,5,6,7,7a-hexahydro-8,8-diméthyl-, 6-propanoate ; acide 2-oxiranecarboxylique, 3- phényl-, ester éthylique ; 4H-4a,9-méthanoazuléno[5,6-d]-1,3-dioxole, octahydro-2,2,5,8,8,9a-hexaméthyl-, (4aR,5R,7aS,9R)- ; acide butanoïque, ester 1,1-diméthyl-2-phényléthylique ; cyclododéca[c]furan, 45 1,3,3a,4,5,6,7,8,9,10,11,13a-dodécahydro- ; benzènebutanenitrile, α,α,γ-triméthyl- ; 2-butanone, 4-(1,3-benzodioxol-5-yl)- ; acide benzoïque, 4-hydroxy-3-méthoxy-, ester méthylique ; 3-cyclopentène-1-butanol, β,2,2,3-tétra- méthyl-2-méthyl-4-(2,2,3-triméthyl-3-cyclopentén-1-yl)butanol ; 2-buténal, 2-méthyl-4-(2,6,6-triméthyl-1-cyclo- hexén-1-yl)- ; 2-naphtalénol, décahydro-2,5,5-triméthyl- ; 1,7-octanediol, 3,7-diméthyl- ; 2H-1-benzopyran-2-one ; 1,3-dioxolane, 2-[6-méthyl-8-(1-méthyléthyl)bicyclo[2.2.2]oct-5-én-2-yl]- ; acide propanoïque, 2,2-diméthyl-, ester 50 3a,4,5,6,7,7a-hexahydro-4,7-méthano-1H-indén-6-ylique ; acide butanoïque, ester (2E)-3,7-diméthyl-2,6-octadién- 1-ylique ; 2-butanone, 4-(4-hydroxyphényl)-; acide 10-undécénoïque, ester butylique ; et des combinaisons de ceux- ci.

4. Composition selon la revendication 1, dans laquelle le matériau de parfum volatil est choisi dans le groupe constitué 55 de :

(i) un matériau de parfum hautement volatil possédant une pression de vapeur > 13 Pa (0,1 Torr) à 25 °C ; (ii) un matériau de parfum modérément volatil possédant une pression de vapeur dans la plage de 13 Pa (0,1

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Torr) à 25 °C à 0,133 Pa (0,001 Torr) à 25 °C ; et (iii) leurs combinaisons.

5. Composition selon la revendication 1, comprenant en outre de l’éthanol dans la quantité de 50 % en poids à 80 % 5 en poids, ou de 55 % en poids à 75 % en poids, par rapport au poids total de la composition.

6. Composition selon la revendication 1, comprenant en outre un ou plusieurs co-modulateurs de parfum non odori- férants choisis dans le groupe constitué de :

10 (i) l’alcool isocétylique ; (ii) l’éther myristylique de PPG-3 ; (iii) le diéthylhexanoate de néopentyl glycol ; et (iv) mélanges de ceux-ci, de préférence avec de l’alcool isocétylique.

15 dans laquelle le ou les co-modulateurs de parfum non odoriférants sont présents dans la quantité de 0,05 % en poids à 10 % en poids, de préférence de 0,5 % en poids à 6 % en poids, par rapport au poids total de la composition.

7. Composition selon la revendication 8, dans laquelle les modulateurs de parfum non odoriférants sont formés d’au moins 50 % en poids d’un modulateur de parfum non odoriférant, par rapport au poids combiné des modulateurs 20 de parfum non odoriférants et des co-modulateurs de parfum non odoriférants.

8. Composition selon la revendication 1, comprenant en outre un ou plusieurs co-modulateurs de parfum non odori- férants choisis dans le groupe constitué d’alcool isocétylique, éther myristylique de PPG-3, diéthylhexanoate de néopentyl glycol ou un mélange de ceux-ci de préférence avec de l’alcool isocétylique, de préférence dans la quantité 25 de 0,5 % en poids à 6 % en poids, par rapport au poids total de la composition.

9. Procédé pour renforcer le profil de parfum d’une composition, de préférence améliorer la longévité d’un arôme, de préférence un arôme floral, d’une composition, comprenant la mise en contact ou le mélange d’au moins un modulateur de parfum non odoriférant avec au moins un matériau de parfum faiblement volatil conformément à une 30 composition selon l’une quelconque des revendications précédentes.

10. Procédé selon la revendication 9, dans lequel l’arôme floral est choisi dans le groupe constitué d’une note de type lavande, une note de type rose, une note de type lis des vallées, une note de type muguet, une note de type jasmin, une note de type magnolia, une note de type cyclamen, une note de type jacinthe, une note de type lilas, une note 35 de type fleur d’oranger, une note de type fleur de cerisier, une note de type pivoine, une note de type lotus, une note de type tilleul, une note de type Osmanthus, une note de type lilas, une note de type héliotrope, une note de type violette, une note de type iris, une note de type tiaré et des combinaisons de ceux-ci.

11. Procédé de production d’un produit de consommation, comprenant la mise en contact ou le mélange dans le produit 40 d’une quantité active du point de vue organoleptique d’une composition de parfum selon l’une quelconque des revendications 1 à 8.

12. Produit ou article de consommation parfumant comprenant une composition de parfum selon l’une quelconque des revendications 1 à 8, dans lequel le produit de consommation parfumant est choisi dans le groupe constitué d’un 45 produit pour le soin des tissus, un produit pour le soin de l’air ou un produit pour le soin de la maison.

13. Procédé de modification ou de renforcement des propriétés d’odeur d’une surface corporelle, comprenant la mise en contact ou le traitement de la surface corporelle avec une composition selon l’une quelconque des revendications 1 à 8. 50

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REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• US 4264478 A [0009] • US 6893647 B [0048] • US 4324703 A [0012] • WO 9408557 A [0060] • WO 13064412 A2 [0013] • US 4145184 A [0074] • WO 13060691 A2 [0013] • US 4209417 A [0074] • WO 2011154926 A [0014] • US 4515705 A [0074] • WO 201364412 A [0028] • US 4152272 A [0074] • WO 200067721 A [0048] • WO 2013064412 A [0090] • WO 200067720 A [0048] • WO 2013060691 A [0091]

Non-patent literature cited in the description

•MOSHELal.et Perfumer & Flavorist, 1982, vol. 7, • Advanced Chemistry Development (ACD/Labs) Soft- 41-47 [0010] ware, 1994 [0030] [0073] [0075] [0077] [0097] • S. ARCTANDER. Perfume and Flavor Chemicals. Al- lured Publishing Corporation, 1969 [0024]