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Fragrance Composition Duftstoffzusammensetzung Composition Parfumante

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Fragrance Composition Duftstoffzusammensetzung Composition Parfumante (19) TZZ¥ ¥ZZ_T (11) EP 3 279 300 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C11B 9/00 (2006.01) A61K 8/34 (2006.01) 27.03.2019 Bulletin 2019/13 A61Q 5/02 (2006.01) A61Q 19/10 (2006.01) C07C 29/145 (2006.01) C07C 31/125 (2006.01) (2006.01) (2006.01) (21) Application number: 17184231.3 C11D 3/50 D06M 13/144 C07B 61/00 (2006.01) (22) Date of filing: 30.05.2013 (54) FRAGRANCE COMPOSITION DUFTSTOFFZUSAMMENSETZUNG COMPOSITION PARFUMANTE (84) Designated Contracting States: • Asada, Takahiro AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Wakayama, 640-8580 (JP) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Toki, Naotoshi PL PT RO RS SE SI SK SM TR Wakayama, 640-8580 (JP) (30) Priority: 01.06.2012 JP 2012126075 (74) Representative: Hoffmann Eitle Patent- und Rechtsanwälte PartmbB (43) Date of publication of application: Arabellastraße 30 07.02.2018 Bulletin 2018/06 81925 München (DE) (62) Document number(s) of the earlier application(s) in (56) References cited: accordance with Art. 76 EPC: WO-A1-2010/091969 DE-A1-102010 002 104 13796988.7 / 2 857 482 US-A1- 2011 081 393 (73) Proprietor: KAO CORPORATION • Masahiro Manabe ET AL: "The counterion Tokyo 103-8210 (JP) releasing effect and the partition coefficient of branched alkanols in ionic micellar solution", (72) Inventors: COLLOID & POLYMER SCIENCE, vol. 280, no. 10, • Ueda, Junko 1 October 2002 (2002-10-01), pages 929-935, Wakayama, 640-8580 (JP) XP055477085, DE ISSN: 0303-402X, DOI: • Ataka, Yoshiharu 10.1007/s00396-002-0710-3 Wakayama, 640-8580 (JP) 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 3 279 300 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 279 300 B1 Description Technical Field 5 [0001] The present invention relates to a fragrance composition containing 7-methyloctane-3-ol. Background Art [0002] Fragrance is an important element that produces, for example, preference, a sense of luxury, a sense of ease, 10 and expectations for the effect for products and the like. Furthermore, a distinctive fragrance provides a product differ- entiation effect and the capacity for attracting customers. Particularly, floral fragrance notes are preferred for toiletry products. [0003] Alcohols such as linalool, citronellol, and geraniol are known as fragrance materials that impart floral fragrance notes. 15 [0004] On the other hand, in order to control, for example, a long-lasting property and balance of a fragrance, generally, a fragrance is imparted to a product using a fragrance composition in which a plurality of fragrance materials are mixed together. It is required for the fragrance materials composing the fragrance composition to be highly harmonious with other fragrance materials. 20 Examples of commercial products of alcohols include [0005] 3,4,5,6,6-pentamethylheptane-2-ol, which is sold as Kohinol (product name) by IFF [0006] Furthermore, 25 Patent Document 1 discloses that 2,5,7-trimethyl-3-octanol and 2,4-dimethyl-8-nonanol each are useful as a fra- grance and have a fruit-like fragrance note. Patent Document 2 discloses that, for example, 3-butyl-6-methylheptane-2-ol is useful as a fragrance and has a green narcissus and aromatic gentian like fragrance notes. Patent Document 3 discloses that 3-hydroxy-7-isobutyl-1,6-octadiene and derivatives thereof each are useful as a 30 fragrance and have a fresh grass-like fragrance note. [0007] Very roughly speaking, fragrance materials have similar fragrance notes when they have similar structures to each other, but there are many exceptions. Particularly, when a plurality of substituents are combined to change the structure, it is difficult to predict how the fragrance note will change and it is also difficult to predict the harmonicity wi th 35 other fragrance materials. Prior Art Documents Patent Documents 40 [0008] [Patent Document 1] JP 54(1979)-27506 A [Patent Document 2] WO 2011/135487 45 [Patent Document 3] U.S. Patent No. 3,452,105 [0009] US 2011/081393 describes a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of di-ester compounds of dicarboxylic acid represented by a specific formula. Among the alcohols useful for the esterification, various branched, saturated C9-alcohols are mentioned. 50 [0010] DE 10 2010 002104 is directed to perfume compositions for masking malodors. The compositions comprise anoxidizing agent in combinationwith fragrance compounds selectedfrom saturatedalcohols, saturated esters, saturated ethers and others. [0011] WO 2010/091969 relates to perfume compositions of the lily of the valley type comprising a) 2-methyl∼3-(3- tert.-butylphenyl)propanal and b) 2 ∼isobutyl-4-methyl-tetrahydro-2H-pyran-4-ol and c) optionally one or more additional 55 fragrance substancels) and d) optionally one or more diluent(s). 2 EP 3 279 300 B1 Disclosure of Invention Problem to be Solved by the Invention 5 [0012] Some fragrance materials may interfere with other fragrance components and thereby may change fragrance notes or weaken them mutually. Therefore, in order to increase flexibility in blending odors, it is desired to increase the number of types of fragrance materials. Particularly, fragrance compositions that have fresh floral fragrance notes with a feeling of cleanliness and that are used suitably to impart fragrances to toiletry products have been desired. [0013] Therefore, the present invention is directed to the use of a fragrance composition that has excellent harmonicity 10 with various other fragrances and can impart a stronger floral feeling by being blended. Means for Solving Problem [0014] The present inventors found that saturated aliphatic alcohol with a specific structure has excellent harmonicity 15 with various fragrances and imparts a stronger floral feeling by being blended, and thereby the present invention was completed. [0015] That is, the present invention is directed to the use of a fragrance composition containing 7-methyloctane-3- ol, as a fragrance component. 20 Description of the Invention [Method of Producing 3,6-Dimethylheptane-2-ol] [0016] The 3,6-dimethylheptane-2-ol (represented by Formula (I) below. In the present description, it may also be 25 referred to as Compound (I).) can be synthesized using a common organic chemical reaction. The method of producing it is not limited. For example, Compound (I) can be produced using a method including a step of obtaining Compound (I) by carrying out a cross aldol reaction using isovaleraldehyde (represented by Formula (XI) below. In the present description, it may also be referred to as Compound (XI).) and 2-butanone (represented by Formula (X) below. In the present description, it may also be referred to as Compound (X).), and then dehydrating and reducing it (see Scheme 1). 30 35 40 45 50 [0017] In the aforementioned production method, first, the cross aldol reaction is carried out using isovaleraldehyde 55 (XI) and 2-butanone (X) in the presence of a base catalyst. The base catalyst is preferably alkali metal hydroxide, more preferably sodium hydroxide. The reaction is carried out at a temperature of, for example, 15 to 30°C, for example, 1 to 60 hours. [0018] Particularly, from the viewpoint of making the cross aldol reaction proceed with a good yield, it is preferable to 3 EP 3 279 300 B1 further add water to the reaction solution. [0019] Subsequently, the product thus obtained is dehydrated. Preferably, the dehydration is carried out at the tem- perature not lower than the boiling point of water, with, for example, phosphoric acid being added to the reaction solution. When the pressure of the reaction system is changed, it is preferable that the dehydration be carried out at the temperature 5 not lower than the boiling point of water that is obtained under such pressure. When it is carried out at 1 atm (101 kPa), it is preferable that the product be dehydrated while being heated, for example, at 110 to 160°C. [0020] The dehydration allows 3,6-dimethylhept-3-en-2-one (represented by Formula (III) above. In the present de- scription, it may also be referred to as Compound (III).) to be obtained. [0021] In the cross aldol reaction, when 7-methyloct-4-en-3-one (represented by Formula (IV) below. In the present 10 description, it may also be referred to as Compound (IV).) is obtained together with Compound (III) (see Scheme 2), Compound (III) may be separated from Compound (IV) by precision distillation or a combination of a silica gel column and distillation. This separation allows Compound (III) with a higher purity to be obtained. Alternatively, adjusting the conditions for the separation allows a mixture of Compound (III) and Compound (IV) at a specific ratio to be obtained. 15 20 25 30 35 [0022] Subsequently, Compound (III) is reduced and thereby Compound (I) is obtained. The reduction method is not particularly limited as long as it is a general reduction method. However, from the view point of increasing the purity, a hydrogenation method using a noble metal catalyst is preferred. Specifically, reduction can be carried out by hydrogen- 40 ation under a hydrogen atmosphere in the presence of a noble metal catalyst such as ruthenium, palladium, or platinum. Hydrogenation is carried out under a hydrogen pressure of, for example, 0.1 to 5 MPa preferably at a temperature of 50 to 170°C, more preferably at a temperature of 60 to 160°C, and further preferably at a temperature of 80 to 160°C.
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