US 20130209385A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0209385 A1 Kulkarni et al. (43) Pub. Date: Aug. 15, 2013

(54) COSMETIC COMPOSITION WITH Publication Classification WATERTIGHT FRAGRANCE (51) Int. Cl. (71) Applicant: COTY B.V., (US) A618/8 (2006.01) A618/37 (2006.01) (72) Inventors: Rupali A. Kulkarni, Bridgewater, NJ A61O 19/10 (2006.01) (US); Leslie C. Smith, Princeton, NJ A61O 13/00 (2006.01) (US); William Kopf, Mine Hill, NJ A61O 15/00 (2006.01) (US); Lisa D. Gilliam, Scotch Plains, NJ (52) U.S. Cl. (US); Ralph Macchio, Sparta, NJ (US) CPC ...... A61K 8/8158 (2013.01); A61O 13/00 (2013.01); A61O 15/00 (2013.01); A61O 19/10 (73) Assignee: COTY B.V., HAARLEM (NL) (2013.01); A61K 8/37 (2013.01) (21) Appl. No.: 13/796,659 USPC ...... 424/65; 512/2; 510/130; 424/70.17 (22) Filed: Mar 12, 2013 (57) ABSTRACT Related U.S. Application Data (63) Continuation of application No. 13/014,831, filed on The present invention refers to a cosmetic composition Jan. 27, 2011, now abandoned, which is a continuation which, in particular, enables the perfume component resist of application No. 1 1/362,512, filed on Feb. 27, 2006, wash off by water and sweat and to remain fixed on the skin now abandoned, which is a continuation of application for a long time watertightly. The cosmetic composition com No. PCT/EP2005/000931, filed on Jan. 26, 2005. prises fragrance and a fragrance-fixing complex consisting of (60) Provisional application No. 60/600,018, filed on Aug. 0.01-10% by weight of a hydrophobic, alcohol-soluble, car 9, 2004. boxylated acrylates/octylacrylamide copolymer and 0.01-10% by weight of a hydrolyzedjojoba ester. Further the (30) Foreign Application Priority Data complex is able to significantly reduce the total amount of fragrances while giving the same scent feeling to the con Jan. 27, 2004 (DE) ...... 102004.005095.3 SUC. Patent Application Publication Aug. 15, 2013 Sheet 1 of 4 US 2013/0209385 A1

aggil Be A3S s3 pleife. Patent Application Publication Aug. 15, 2013 Sheet 2 of 4 US 2013/0209385 A1

000"| ~009 009

23S BC s: . Boc eely Patent Application Publication Aug. 15, 2013 Sheet 3 of 4 US 2013/0209385 A1

Patent Application Publication Aug. 15, 2013 Sheet 4 of 4 US 2013/0209385 A1

--lost 25 Feglec

- Alas court 96% E Flagasca & Scintight Corals: 10,000,000,000

1800,000,000

OGOOOOO!--- 1 MENS R 4 HR Title

Fig. 4. US 2013/0209385 A1 Aug. 15, 2013

COSMETIC COMPOSITION WITH well as further active agents. Auxiliaries include e.g. preser WATERTIGHT FRAGRANCE Vatives, colourants, polyols, esters, electrolytes, gel-forming 0001. This application claims the benefit of the filing date agents, polar and non-polar oils, polymers, further copoly of U.S. Provisional Application Ser. No. 60/600,018 filed mers, stabilizers, Surface-active agents. Aug. 9, 2004 which is incorporated by reference herein. 0015 Cosmetic active agents include e.g. organic Sun 0002 The present invention refers to a cosmetic compo screens, Scavengers, moisturizing Substances, vitamins, sition which, in particular, enables the perfume component to enzymes, plant-based active agents, polymers, antioxidants, resist wash off by water and sweat and to remain fixed on the anti-inflammatory natural active agents. skin for a long time (fragrance-watertight composition). 0016 Preferred cosmetic fragrances are oil-soluble fra 0003. It is known to encapsulate perfume oils in liposomes grances Such as all fragrance oils which are known for the or cyclodextrins to achieve a controlled release of these oils. skilled in the art. Several systems have also been used to improve bonding to 0017. The hydrophobic, alcohol-soluble, carboxylated the skin or to extend the time the perfume lasts, e.g. chitin acrylates/octylacrylamide copolymer used according to the derivatives, quaternary chitosans, silicate materials and ther invention is soluble in ethanol, isopropanol and fatty alco moplastic polyamides. hols. It can be made water-soluble or dispersible in water by 0004 U.S. Pat. No. 6,143,353 A discloses the coating of neutralizing the carboxy groups with water-soluble bases pharmaceutically active ingredients as well as fragrant com Such as triethanolamine, Sodium carbonate, aminomethylpro ponents with an aqueous dispersion of a plasticized, hydro panol, potassium hydroxide or ammonium hydroxide. It can phobic acrylic polymer, which acrylic polymer is an (alkyl) thus be easily washed off the skin with soap, if necessary. Due ester of acrylic/methacrylic acid. to the interaction of the copolymer with the hydrolyzedjojoba 0005 U.S. Pat. No. 6,172,037 B1 discloses perfume-fix ester, which ester is soluble in the aqueous-alcoholic system ing Substances comprising polyvinylpyrrolidone, hydroxy and in glycol, and the solvent, fragrant molecules are inte propyl cellulose and a hydrophobic oil. grated into a complex and remain bonded to the skin for a very 0006. The object of the present invention is to provide a long time. At the same time, the aforesaid complex has a cosmetic composition which is wash-off resistant by water strong water-repellent effect. Thus a very good endurance of and at the same time ensures that the perfume component the fragrant molecules on the skin is achieved during rain, remains fixed on the skin for a long time. Sweat, Swimming, etc. 0007. A further object of the invention is to provide a 0018. A preferred copolymer is Acrylates Octylacryla cosmetic composition with reduced fragrance content and a mide Copolymer with an acidity of 2.4 med/g. Such a product feeling of the fragrance by the consumer without any differ is available under DERMACRYL(RAQF or DER CCC. MACRYL(R)79 by National Starch and Chem. Comp., NJ, 0008 According to the invention, the cosmetic composi USA. tion comprising fragrances is further comprising a fragrance 0019. A preferred hydrolyzed jojoba ester is one of plant fixing complex which comprises origin (Simmondsia chinensis) having a saponification value 0.01 to 10% by weight of a hydrophobic, alcohol-soluble, according to AOCS Cd 3-25* of max. 1 mg KOH/g, a iodine carboxylated acrylates/octylacryl-amide copolymer, value according to AOCS Cd 1d-92* of between 14 and 17 0.01 to 10% by weight of a hydrolyzed jojoba ester, g/100 g and a trans isomer value according to AOCS Cd and where all percents are related to the total weight of the 14-95* of max. 0.1% by weight (* test procedure according to cosmetic composition. American Oil Chemists Society). Such a product (INCI: 0009. The range of fragrances is between 0.01 and 35% by Hydrolyzed Jojoba Esters (and) Water) is available under weight. A preferred range is 0.1-16%, more preferred 0.5-8% Floraesters(R K-20W Jojoba by Int. Floratech Technol. Ltd., by weight, most preferred 1 to 5% by weight. Hartsdale, N.Y., USA. 0010. It is preferred that the copolymer be contained in an 0020. The following substances are particularly suitable amount ranging between 0.1 and 5% by weight, more pre for further processing the cosmetic complex. ferred 0.1-1.0% by weight. The carboxylated acrylates/octy 0021 Oils: Silicone oils, mineral oils, Hydrogenated lacrylamide co-polymer can be replaced by the acrylic poly Polyisobutene, Polyisoprene, Squalane, Tridecyl Trimelli mer Dermacryl R. AQF (National Starch & Chemical Co., tate, Trimethylpropane Triisostearate, Isodecyl Citrate, Neo Bridgewater N.J., USA). penty1 Glycol Diheptanoate, PPG-15 Stearyl Ether as well as 0011 Further it is preferred that the jojoba ester is present vegetable oils such as Calendula Oil, Jojoba Oil, Avocado Oil, in a range of 0.1 to 5%, more preferred 0.1-1% by weight. Macadamia Nut Oil, Castor Oil, Cocoa Butter, Coconut Oil, 0012. In a special embodiment of the invention the jojoba Maize Oil, Cottonseed Oil, Olive Oil, Palm Kernel Oil, Rape ester and the copolymer constitute a separately prepared com seed Oil, Safflower Oil, Sesame Seed Oil, Soybean Oil, Sun plex in the relation 1:1-4, preferably 1:1.2-2.8 of jojoba ester: flower Seed Oil. Wheatgerm Oil, Grapeseed Oil, Kukui Nut polymer. Oil. Thistle Oil, and mixtures thereof. Synthetic squalane or 0013. In a further embodiment of the invention the cos squalane made from natural products is suitable too, as well metic composition comprises an alcohol or alcohol/water as cosmetic esters or ethers which can be branched or linear, mixture. saturated or unsaturated. 0014. The aforesaid fragrance-fixing complex can be used 0022 Scavengers: Antioxidants, vitamins such as Vitamin in cosmetic products such as emulsions, creams, lotions, C and derivatives thereof, e.g. ascorbyl acetate, ascorbyl sprays, shower gels, shower oils, bath products, foam baths, phosphate and ascorbyl palmitate; Vitamin A and derivatives perfumes, aftershaves, shaving balms, face lotions, hair con thereof, folic acid and derivatives thereof. Vitamin E and ditioners, skin gels, deodorants, detergents etc. At the same derivatives thereof such as tocopheryl acetate; flavones and time, further cosmetic auxiliaries and carrier Substances as flavonoids; amino acids such as histidine, glycine, tyrosine, they are commonly used in Such preparations can be used, as tryptophan and derivatives thereof carotenoids and carotenes US 2013/0209385 A1 Aug. 15, 2013

Such as C-carotene, B-carotene; uric acid and derivatives ing clays such as umber and red bole, calcium carbonate, thereof C-hydroxy acids such as citric acid, lactic acid, malic French chalk, mica-titanium oxide, mica-titanium oxide-iron acid. oxide, bismuth oxychloride, nylon beads, ceramic beads, 0023 Moisturizing substances: Glycerine, Butylene Gly expanded and non-expanded synthetic polymer powders, col, Propylene Glycol, and mixtures thereof. powdery natural organic compounds Such as milled solid 0024 Organic sunscreens: Derivatives of 4-aminobenzoic algae, milled plant parts, encapsulated and non-encapsulated acid Such as 4-(dimethylamino)-benzoic acid-(2-ethylhexyl) cereal starches and mica-titanium oxide-organic dye. ester; esters of cinnamic acid Such as 4-methoxy cinnamic 0030. Also included in the composition of the invention acid (2-ethylhexyl) Ester; benzophenone derivatives such as are antiperspirants and deodorants, such as Triclosan, Trim 2-Hydroxy-4-methoxybenzophenone; derivatives of 3-ben ethyl Citrate, Farnesol, Aluminum Chlorhydrate, Aluminum Zylidene camphor such as 3-Benzylidene Camphor. Other Zirconium Tetrachlorhydex GLY etc. preferred oil-soluble UV filters are Benzophenone-3, Butyl 0031. In comparative tests, it has been found that the addi Methoxybenzoylmethane, Octyl Methoxycinnamate, Octyl tion of the complex according to the invention brings about a Salicylate, 4-Methylbenzylidene Camphor, Homosalate, and significant increase in waterproofness during a period of 4-6 Octyl Dimethyl PABA. hours, both in a sensory test with test persons and in an 0025 Surface-active agents: Anionic, amphoteric, non analytical test by means of gas chromatography/mass spec ionic or cationic Surface-active agents, or mixtures thereof. troscopy. The waterproofness of an aftershave in a test lasting Cationic polymers or a mixture of anionic and amphoteric 8 hours was also considerably higher than that of the Surface-active agents are particularly preferred. untreated original product. 0026 Non-limiting examples of anionic foaming surface 0032. It has further been found that the addition of the active agents include those selected from the group consisting complex in the range of 0.5-8% by weight, preferably 1-3% of alkyl Sulphates, alkyl ether Sulphates, Sulphated monoglyc by weight, related to the total weight of the cosmetic compo erides, Sulphonated olefins, alkylaryl Sulphonates, primary or sition, e.g. a perfume, to the other ingredients of the cosmetic secondary alkane Sulphonates, alkyl Sulphosuccinates, acyl composition, can reduce the amount of the fragrance usually taurates, acyl isothionates, alkyl glyceryl ether Sulphonates, added to the composition without loss of fragrance intensity. Sulphonate methyl esters, Sulphonated fatty acids, alkyl phos This means that in consumer studies carried out to determine phates, acyl glutamates, acyl sarcosinates, alkyl Sulpho-ac whether there was a difference in fragrance character between etates, acylated peptides, alkyl ether carboxylates, acyl lac a standard product and a product with 20% less fragrance and tylates of anionic Surface-active agents containing fluorine, added 1-2% of the complex of the invention, no significant and mixtures thereof. Mixtures of anionic surface-active difference has been stated. agents can be effectively used in the present invention. 0033. The preferred method for manufacturing the water 0027. Examples of amphoteric surface-active agents proof cosmetic composition consists in that a hydrolyzed which can be used in the present invention include at least jojoba ester is mixed with some alcohol or alcohol/water those having an acid group. The aforesaid group can be a mixture, and at a temperature ranging between 18-40°C. an carboxyl group or a Sulphonic acid group. Quaternary nitro acrylates/octylacrylamide copolymer in powder form is gen and therefore quaternary amino acids are included. They sprayed into the mixture during the mixing process. The should, in general, contain an alkyl group or alkenyl group received complex can dried before use in the cosmetic for having 7 to 18 carbonatoms. Suitable amphoteric detergents mulation or can directly added to the other ingredients of the include simple betaines and amidobetaines which are a mix composition. Mixing of Some alcohol, the ester, the copoly ture of C12- and C14-alkyl groups derived from the coconut mer and optionally a 10% NaCO, solution in that order is so that at least half, preferably three quarters, of the R1-hy also possible. drocarbon chain has 10 to 14 carbonatoms. It is preferred that the other two R2- and R3-hydrocarbon chains be methyl. 0034. The use of the fragrance-fixing complex of the Further, the amphoteric detergent can be a Sulphobetaine. invention is preferred in the following groups of products Amphoacetates and diamphoacetates can also occur as pos 0035 perfumes sible Zwitterionic and/or amphoteric compounds, which can 0.036 hair care and body care products e.g. hair washes, be used. An amphoteric Surface-active agent should, in gen body washes, shower gels, shampoos, conditioners, etc. eral, be contained in an amount ranging approximately 0037 Sun care products e.g. Sun creams, Sun lotions, between 0.1 and 20%, preferably 5 and 18% by weight, after-Sun products, body bronzers, Sun sprays, Sun milks relative to the composition. etc. 0028 Suitable non-ionic surface-active agents include, 0.038 antiperspirants and deodorants but are not limited to, Coconut Acyl Mono-ethanolamide or Coconut Acyl Diethanolamide, Alkyl Polysaccharide, Lacto 0.039 products of color cosmetic e.g. massacres, foun biomamide, Ethylene Glycol Ester, Glycerine Monoether, dations, make-up, lipsticks, lip balms etc. Polyhydroxyamide (Glucamide), primary and secondary 0040. The invention will hereinafter be explained in more alcohol ethoxylates, particularly Cso aliphatic alcohols detail by means of examples. The figures show ethoxylated with an average of 1 to 20 moles ethylene oxide 0041 FIG. 1: Sensory analysis of aftershave of example 1 per mole of alcohol. Mixtures of the aforesaid surface-active 0042 FIG. 2: Analytical results of aftershave of example 1 agents can also be used. 0029 Pigments, pigment mixtures or powders with a pig 0043 FIG. 3: Sensory analysis of EDT of example 11 ment-like effect, also including those with a pearl-gloss effect 0044 FIG. 4: SPME results for fragrance C (ex. 16) skin may be added to the composition of the invention. The may tight headspace include, for example, iron oxides, aluminum silicates such as 0045 All quantities in the examples are given in percent ochre, titanium (di)oxide, mica, kaolin, manganese contain by weight unless indicated otherwise. US 2013/0209385 A1 Aug. 15, 2013

EXAMPLE1 EXAMPLE 3

Aftershave Body Mist 0046) 0050

Phase A Phase A

Ethanol q.S. ad 100 Alcohol ad 100 Octyl Methoxycinnamate O.2 Fragrance 4.5 Benzophenone-3 O.1 Phase B PEG-60 Hydrogenated Castor Oil 1.5 L-Menthol O.15 Water 16 Phase B White Ginger Extract O.1 Phase C Fragrance 7.0 Ethanol 1S.O Alcohol 1.5 Phase C Watertight complex* O.S Phase D Water 12 Allantoin O.1 Colorant O.2 Phase D *see ex. 2 Ethanol 6.O Hydrolyzed Jojoba Esters & Water O.S Acrylates/Octylacrylamide Copolymer 1.O 0051 Mix alcohol and fragrance with agitation. Add Phase E phase B with agitation and mix until clear and uniform. Filter the main batch and add separate mixed phase C to the main Colourants O.O15 batch with agitation. Add phase D and mix until uniform.

0047. The ingredients of Phase A were mixed with one EXAMPLE 4 another, incorporating PEG-60 Hydrogenated Castor Oil at approx. 60° C. Separately, Phases B and C were prepared in Clear Antiperspirant Gel (Female) the same manner. Phase D was prepared by mixing the jojoba ester with ethanol at approx. 25°C. while spraying in the 0.052 copolymer in powder form during the mixing process. The mixture was then stirred until a clear, homogeneous Solution was obtained. First, Phase D was mixed with Phase B. Sub Phase A sequently, Phases A and C were mixed with one another and Cyclomethicone 2.5 the mixture was filtered using a filter cushion (60S). The Dimethicone O.S mixture of Phases D and B was then added into the mixture of Cyclopentasiloxane(and)PEG/PPG-18/18 Dimethicone 7.5 Phases A and C while stirring and finally Phase E was added Triethyl Citrate O.1 and the overall mixture was stirred at a constant speed. Farnesol O.OS Phase B EXAMPLE 2 Aluminum Zirconium Tetrachlorohydrex GLY S4 Water ad 100 Allantoin O.1 Antiperspirant Soft Solid Polysorbate 80 O.S Dipropylene Glycol 21 0048 Phase C Fragrance O.S Phase D Cyclomethicone and Dimethicone Crosspolymer 32 Stearyl Dimethicone 1 Watertight complex* O.S Hydrogenated Castor Oil 1 Cyclomethicone ad 100 *see ex. 2 Watertight complex* O.S Dimethicone 15 0053 Mix phase A and B ingredients separately. If the Aluminum Zirconium Tetrachlorohydrex GLY 24 refractive index of phase A is higher than of phase B, add */3 Acrylates Octylacrylamide Copolymer some water to phase B. Add phase B to phase A very slowly /3 Hydrolyzed Jojoba Esters(and)Water while rapidly mixing phase A and homogenize. Add phase C and mix until uniform. Add phase D while agitation. 0049 Weigh ingredients 1-5 into a vessel, heat to 80-85° C. and mix until waxes have melted and the mixture appears EXAMPLE 4A uniform. Remove from heat and add Dimethicone. The mix ture will set at about 75° C. Add Al Zr-Tetrachlorohydrex 0054 Agel is prepared as in example 4 whereby the water after mixture cools below 75° C. Continue mixing and cool tight complex comprises 0.5% Dermacryl(RAQF and 0.25% ing until the temperature is below 45° C. Hydrolyzed Jojoba Esters. US 2013/0209385 A1 Aug. 15, 2013

EXAMPLE 5 -continued Phase E Conditioner Water 2 0055 Phenonip O.S Phase F Fragrance O.8

Phase A *see ex. 2 Water ad 100 Disodium EDTA O.O2 0.058 Mix water phase A ingredients separately and heat Phase B to 75-85°C. while mixing, maintain temperature. Mix phase B ingredients without Potassium Cetyl Phosphate (PCP) and Steareth-20 1 Dithicone Bisamino Hydroxypropyl Copolyol 0.7 heat to 75-80° C., add PCP until free of lumps. Add melted Watertight complex* O.S phase C ingredients (45-50°C.) to phase B and add phase B Citric Acid C.S. (75°C.) to phase A. Homogenize for 7-10 minutes. Add from Phase C phase D water and TEA at 65° C. and after than the complex. At 50° C. add Cyclomethicone and than Panthenol. Add Cetearyl Alcohol 2 Dipalmitoylethyldimonium Chloride 3 phase E and Fat 35° C. and cool to 30° C. Glyceryl Stearate 0.75 Phase D EXAMPLE 7

Preservative O.S Shampoo Fragrance 1.5 Sodium Hydroxide C.S. 0059

see ex. 2 0056 Combine phase A ingredients with mixing and heat Phase A to 70° C., maintain temperature. Add with mixing phase B PhyllantriolkDisodium EDTA&Hydroxypropyl 55 ingredients one by one to phase A, mix until uniform and GuarkHydroxypropyltrimonium Cloride& adjust pH by citric acid. Combine phase C ingredients and Tocopherylacetate (Miraspec KTS) heat to 70° C. and mix to main batch until uniform. Add Phase B individually phase Dingredients and adjust pH with sodium Fragrance 1 hydroxide. Phase C

Plant extracts O.3 EXAMPLE 6 Water ad 100 Watertight complex* 1.8 Lotion Phase D Colorant O.15 0057 Phase E Citric Acid (20% solution) C.S. Phase F Phase A Ammonium Chloride (20% solutione) 2.4 Water ad 100 *both ingredients 1:1 Disodium EDTA O.OS Glycerine 2 Carbomer O.3 0060 Mix separat prepared phases A and B. Add phase C Pemulan O.1 ingredients while mixing. Add each ingredient of phase C Phase B separately to main main batch until clear and uniform. Con tinue mixing while adding phase D. Adjust pH with phase E Tribehenin 1.3 DC 200, SOO 1 if necessary. Add phase F while mixing. Stearoxytrimethylsilane(and)Stearyl Alcohol 0.7 Diisostearyl Dimer Dillinoleate 6 EXAMPLE 8 BHT O.OS VP. Eicosene Copolymer 1 Shower Gel Potassium Cetyl Phosphate O.S Phase C 0061

Vitamin AAcetate O.S Phase D Phase A Water 2 Triethanolamine 0.4 Water ad 100 Watertight complex* 1.5 Disodium EDTA O.1 Cyclomethicone 1 Hydroxypropyl 1 D Panthenol L 1 DMDM Hydantoin O.3 US 2013/0209385 A1 Aug. 15, 2013

-continued -continued Phase B Watertight complex* 5 Sodium Laureth Sulfate 10 Colorant 1 Disodium Laureth Sulfate 2O Cocamidopropyl Betaine 9 Phase C *see ex. 2 Preservative O.2 Fragrance 2 Dye O.3 EXAMPLE 11 Phase D Sodium Chloride (20% solution) O.8 Phase E Eau de Toilette (EDT) Sodium Hydroxide (25% solution) C.S. 0066 Phase F Dermacryl (R) AQF O.S Hydrolyzed Jojoba Esters O.25 Phase A

0062 Mix separat prepared phases A and B. Add phase C Alcohol ad 100 ingredients while mixing. Add each ingredient of phase C Fragrance 15 separately to main main batch until clear and uniform. Adjust Benzophenone 2 O.1 Viscosity with phase D and continue mixing. Adjust pH with Phase B phase E while mixing. Add phase F while mixing. Water 3.6 Beispiel 8a Phase C

0063 A shower gel is prepared as in example 8 whereby Alcohol 10 the watertight complex comprises 0.5% Dermacryl(R) AQF Watertight complex* 3 and 0.25% Hydrolyzed Jojoba Esters. Phase D

EXAMPLE 9 Colorant O.3

Eau de Toilette *see ex. 2 0.064 0067 Mix separate prepared phases A and B. Mix alcohol and Hydrolyzed Jojoba Esters. Sprinkle in Acrylates/Octy lacrylamide Copolymer while mixing and mix until clear and Phase A uniform. Add phase C to the main batch and after that phase Alcohol ad 100 D. Mix until uniform. Fragrance 17 Benzophenone-2 O.1 Phase B EXAMPLE 12

Water 1.6 Phase C Clear Deodorant Stick

Colorant O.3 Phase D 0068 Dermacryl (R) AQF 5 Hydrolyzed Jojoba Esters 2 Phase A The proceeding is according to example 11. Propylene Glycol ad 100 Sodium Stearate 6.5 EXAMPLE 10 Isosteareth-20 5 Steareth-2 1 Perfume Phase B 10% NaOH SCI O.1 0065 Water 14.5 Watertight complex* O.S Phase C

Alcohol ad 100 Fragrance 1.5 Fragrance 2O Colorant 0.4 Benzophenone 2 O.1 Water 9 *see ex. 2 US 2013/0209385 A1 Aug. 15, 2013

EXAMPLE 13 0076. In a sensory test performed with 4 experienced testers, a result according to FIG. 1 was obtained. The same Perfume samples were analysed by means of gas chromatography/ mass spectroscopy and the diagram according to FIG. 2 was 0069 obtained. The results were achieved by SPME (see example 16 part B). Both results demonstrate that the waterproofness is considerably increased. Phase A 0077. In a comparative test using a EDT according to Example 11 (Sample C but with 0.5% complex only) and the Alcohol 65 Benzophenone-2 O.1 same EDT without the complex of copolymerandjojoba ester Fragrance 13.5 (Sample D), the waterproofness determined by means of a Phase B long-time sensory test was found to be more than twice the values of the same EDT without the complex according to the Water ad 100 invention after 6 hours. A similar test using an aftershave Phase C demonstrated this superiority in a sensory test even after 8 Colorant 1.O hours. Phase D EXAMPLE 16 Dermacryl (R) AQF 10 Hydrolyzed Jojoba Esters 5 Comparative Test II 0070 Phases A and B are mixed and filtered. Phase C is Part A added while mixing. Separately prepared phase D is added to 0078 Comparative tests were carried out to demonstrate the main batch and mixed until clear and uniform. the ability of the complex of the invention to reduce the fragrance content in a perfume. EXAMPLE 1.4 (0079. Two perfumes were produced. Perfume C had the following ingredients (in 96 by weight): 72.7% Alcohol, 0.5% Perfume Diisopropyl Adipate, 0.5% C12-C15-Alkyl Lactate, 12% (0071 Fragrance, 14.3% Water. Perfume C1: the first three ingredi ents were the same as in Perfume C but with 9.6% Fragrance, 15.3% Water, 1% complex of example 2, 0.4% Na-O solu tion (10%). Phase A 0080 A group of 20 panelists were asked to identify the Alcohol 55 different fragrance shares in perfume C and perfume C1. Benzophenone-2 O.1 Three panelists identified the different fragrances correctly, Fragrance 2O 17 did not. Phase B 0081. The same results were obtained with a reduction of Water ad 100 fragrance from 16% to 12.8% and from 15% to 12% respec Phase C tively (each with 1% of the complex in the formula with the reduced fragrance share). Alcohol 10 Dermacryl (R) AQF 3.3 Hydrolyzed Jojoba Esters 1.7 Part B SPME Test Colorant 1.O I0082 Solid-phase micro extraction (SPME) is a method in which analytes partition from a sample into a polymer, coated 0072 Phases A and B are mixed and filtered. Separately on a fused silica rod of typically 1 cm length by 100 um prepared phase C is added to the main batch and mixed until diameter. The fiber is fastened into the end of a fine stainless clear and uniform. steel tube contained in a Syringe-like device and protected by 0073 Phase C is added while mixing. an outer stainless steel needle. The device's plunger is depressed to expose the fiberto the sample matrix, retracted at EXAMPLE 1.5 the end of the sampling time, and then depressed again to expose the fiber to a desorption interface for analysis, in this Comparative Test I case by Gas Chromatography. Reference is made to ex. 2 of US 20O2/O192174A1. 0074 Comparative tests were carried out using the com I0083. The result of the GC measurement is presented in position according to Example 1 (Sample A) and the same FIG. 4 with 12% perfume C and 9.6% perfume C1 including composition without the ingredients of Phase D (Sample B). 1% of the watertight skintight complex according to example 0075. Two drops (approx. 0.3 g) of each sample were 2. Both perfumes show nearly the same area counts. This dropped on to the inner side of the right or left forearm of the confirms the results of the consumer test of part A. test person. The drying time was 15 minutes. Two hours later, 0084. Without further elaboration, it is believed that one the forearm was immersed in water having a temperature of skilled in the art can, using the preceding description, utilize 26°C. for 4 minutes. The forearm was then dried in the air. the present invention to its fullest extent. The preceding pre The immersion and drying process was repeated after 4 and 6 ferred specific embodiments are, therefore, to be construed as hours, rinsing the water container and changing the water in merely illustrative, and not limitative of the remainder of the the container before each immersion. disclosure in any way whatsoever. US 2013/0209385 A1 Aug. 15, 2013

0085. In the foregoing and in the examples, all tempera 55. The method of claim 54, wherein said one or more tures are set forth uncorrected in degrees Celsius and, all parts fragrances are present in an amount ranging between 0.1 and and percentages are by weight, unless otherwise indicated. 8% by weight. I0086. The entire disclosures of all applications, patents 56. The method of claim 47, wherein said hydrolyzed and publications, cited herein and of corresponding German jojoba ester is derived from the plant Simmondsia chinensis application No. 10 2004 005 095.3, filed Jan. 27, 2004, and and has a saponification value according to the American Oil U.S. Provisional Application Ser. No. 60/600,018, filed Aug. Chemists Society test procedure ACOS Cd 3-25 of max. 1 mg KOH?g, a iodine value according to the American Oil Chem 9, 2004, are incorporated by reference herein. ists Society test procedure ACOS CdId-92 of between 14 and 0087. The preceding examples can be repeated with simi 17 g/100g and a trans isomer value according to the American lar Success by Substituting the generically or specifically Oil Chemists Society test procedure ACOS Cd 14-95 of max. described reactants and/or operating conditions of this inven 0.1% by weight. tion for those used in the preceding examples. 57. The method of claim 47, wherein the complex is pro 0088. From the foregoing description, one skilled in the art vided in a cosmetic product selected from perfumes, Eau de can easily ascertain the essential characteristics of this inven Toilettes, hair products, body care products, Sun care prod tion and, without departing from the spirit and scope thereof, ucts, antiperspirants, deodorants, detergents and products of can make various changes and modifications of the invention color cosmetic. to adapt it to various usages and conditions. 58. The method of claim 47, wherein the amount of the 1-46. (canceled) complex in the cosmetic product is in the range of 0.5 to 10% 47. A method of providing water-resistant fragrance, the by weight. method comprising: 59. The method of claim 47, wherein the amount of the applying to skin a cosmetic composition with a watertight complex in the cosmetic product is in the range of 0.5 to 4% fragrance, the composition comprising: a) one or more by weight. fragrances, and b) 0.1 to 15% by weight of a fragrance 60. The method of claim 47, wherein the amount of the fixing complex consisting of 0.01 to 10% by weight of a complex in the cosmetic product is in the range of 0.5 to 1.5% hydrophobic, alcohol-soluble, carboxylated acrylates/ by weight. octylacrylamide copolymer and 0.01 to 10% by weight 61. The method of claim 47, wherein the composition of a hydrolyzed jojoba ester, Such that the one or more further comprises cosmetic auxiliaries, cosmetic actives, and fragrances are resistant to wash off by water and Sweat carrier Substances as commonly used in cosmetic composi and remain fixed on the skin, tions. wherein all percents are related to the total weight of the 62. The method of claim 47, wherein the amount of the cosmetic composition, copolymer is in the range of 0.1 to 5% by weight, the amount characterized in that of the jojoba ester is in the range of 0.1 to 5% by weight, and the fragrance-fixing complex is formed prior to addition said one or more fragrances are present in an amount ranging of the fragrance by spraying at a temperature of 18° to between 0.01 and 35% by weight. 25° C. the acrylates/octylacrylamide copolymer in 63. The method of claim 47, wherein the amount of the powder form into a mixture consisting of the hydro copolymer is in the range of 0.1 to 1% by weight, the amount lyZedjojoba ester and an alcohol or an alcohol/water of the jojoba ester is in the range of 0.1 to 1% by weight, and mixture. said one or more fragrances are present in an amount ranging 48. The method of claim 47, wherein the composition between 0.1 and 16% by weight. further comprises an alcohol or an alcohol/water mixture. 64. The method of claim 47, wherein saidjojoba ester and 49. The method of claim 47, wherein the amount of the said copolymer constitute a separately prepared complex in copolymer is in the range of 0.1 to 5% by weight. the relation 1:1-4 of jojoba ester: polymer. 50. The method of claim 49, wherein the amount of the 65. The method of claim 47, wherein saidjojoba ester and copolymer is in the range of 0.1 to 1% by weight. said copolymer constitute a separately prepared complex in 51. The method of claim 47, wherein the amount of the the relation 1:1.2-2.8 of jojoba ester: polymer. jojoba ester is in the range of 0.1 to 5% by weight. 66. The method of claim 47, wherein said one or more 52. The method of claim 51, wherein the amount of the fragrances are oil-soluble fragrances. jojoba ester is in the range of 0.1 to 1% by weight. 67. The method of claim 47, wherein the amount of the 53. The method of claim 47, wherein said one or more complex is in the range of 0.5-8% by weight, relative to the fragrances are present in an amount ranging between 0.01 and total weight of the cosmetic composition. 35% by weight. 68. The method of claim 47, wherein the amount of the 54. The method of claim 53, wherein said one or more complex is in the range of 1-3% by weight, relative to the total fragrances are present in an amount ranging between 0.1 and weight of the cosmetic composition. 16% by weight. k k k k k