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.