US009265711 B2 (12) United States Patent (10) Patent No.: US 9,265,711 B2 Kulkarni et al. (45) Date of Patent: Feb. 23, 2016 (54) COSMETIC COMPOSITION WITH (58) Field of Classification Search WATERTIGHT FRAGRANCE CPC ......... A61Q 1/00; A61Q 19/00; A61Q 13/00; A61Q 15/00; A61Q 19/10; A61K 8/8152: (71) Applicant: COTY B.V., Haarlem (NL) A61K 8/81.58: A61K 8/92: A61K 8/96; A61K 8/922: A61K 8/8141; A61K 2800/56; (72) Inventors: Rupali A. Kulkarni, Bridgewater, NJ A61K 28OOF57 (US); Leslie C. Smith, Princeton, NJ See application file for complete search history. (US); William Kopf, Mine Hill, NJ (US); Lisa D. Gilliam, Scotch Plains, NJ (56) References Cited (US); Ralph Macchio, Sparta, NJ (US) U.S. PATENT DOCUMENTS (73) Assignee: COTY B.V., Haarlem (NL) 5,989,529 A 1 1/1999 Kaplan 6,027,739 A 2/2000 Nichols (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 151 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 13/796,659 DE 10002107 8, 2001 DE 101.08387 8, 2002 (22) Filed: Mar 12, 2013 (Continued) (65) Prior Publication Data OTHER PUBLICATIONS US 2013/0209385 A1 Aug. 15, 2013 Cummings, "Built to last: A new jojoba derivative has been found to have impressive Substantivity properties in a wide range of formula Related U.S. Application Data tion types,” J. Soap, Perfumery & Cosmetics (2001) 74: 42-45. (63) Continuation of application No. 13/014,831, filed on (Continued) Jan. 27, 2011, now abandoned, which is a continuation of application No. 1 1/362,512, filed on Feb. 27, 2006, Primary Examiner — Lakshmi Channavaljala now abandoned, which is a continuation of application (74) Attorney, Agent, or Firm — Novak Druce Connolly Bove + Quigg LLP (Continued) (57) ABSTRACT (30) Foreign Application Priority Data The present invention refers to a cosmetic composition Jan. 27, 2004 (DE) ......................... 10 2004 OO5 095 which, in particular, enables the perfume component resist wash off by water and sweat and to remain fixed on the skin (51) Int. Cl. for a long time watertightly. The cosmetic composition com A6 IK 8/02 (2006.01) prises fragrance and a fragrance-fixing complex consisting of A 6LX8/97 (2006.01) 0.01-10% by weight of a hydrophobic, alcohol-soluble, car boxylated acrylates/octylacrylamide copolymer and (Continued) 0.01-10% by weight of a hydrolyzedjojoba ester. Further the (52) U.S. Cl. complex is able to significantly reduce the total amount of CPC ................. A61K 8/8158 (2013.01); A61K 8/37 fragrances while giving the same scent feeling to the con (2013.01); A61K 8/922 (2013.01); A61O 13/00 SUC. (2013.01); A61O 15/00 (2013.01); A61O 19/10 (2013.01) 22 Claims, 4 Drawing Sheets 10 Wins 2 ours i lours US 9,265,711 B2 Page 2 Related U.S. Application Data 2004/O146477 A1 7/2004 Meffert et al. 2004/0265343 A1 12, 2004 Hill No. PCT/EP2005/000931, filed on Jan. 26, 2005, now 2009,019 1243 A9 T/2009 H11 abandoned. FOREIGN PATENT DOCUMENTS (60) Provisional application No. 60/600,018, filed on Aug. 9, 2004. EP 1133973 A1 9, 2001 EP O71.0114 B1 2, 2003 EP 1715841 B1 5/2007 WO O 1492.57 T 2001 (51) Int. Cl. WO 2005OO4831 A1 1, 2005 A6 IK 8/84 (2006.01) WO 2005070371 8, 2005 A6 IK 8/8 (2006.01) A6 IK 8/92 (2006.01) OTHER PUBLICATIONS A61O 13/00 (2006.01) Final Office Action (USPTO) mailed on Oct. 28, 2010 in U.S. Appl. A6 IK S/37 (2006.01) No. 1 1/362,512. (10 pages). A61O 15/00 (2006.01) Final Office Action (USPTO) mailed on Sep. 14, 2012 in U.S. Appl. A61O 19/10 (2006.01) No. 13/014,831. (15 pages). International Preliminary Report on Patentability mailed on Jul. 27. (56) References Cited 2006 in International Application No. PCT/EP2005.000931, Interna tional Filing Date Jan. 26, 2005. (5 pages). U.S. PATENT DOCUMENTS International Search Report and the Written Opinion of the ISA mailed on Jul. 27, 2006 in International Application No. PCT/ 6,143,353 A 11/2000 Oshlack et al. EP2005.000931, International Filing Date Jan. 26, 2005. (5 pages). 6,172,037 B1 1/2001 Perring et al. Non Final Office Action (USPTO) mailed on Mar. 25, 2010 in U.S. 6,190,681 B1 2/2001 Fishman Appl. No. 1 1/362,512. (8 pages). 6,287,579 B1 9, 2001 Kleiman et al. Non Final Office Action (USPTO) mailed on Mar. 29, 2012 in U.S. 7,041,278 B2 5, 2006 Barone et al. Appl. No. 13/014,831. (10 pages). 7.323,162 B2 1/2008 Martin et al. Non Final Office Action (USPTO) mailed on May 22, 2009 in U.S. 2002/0192174 A1 12/2002 Kawakami et al. Appl. No. 1 1/362,512. (10 pages). 2004/0028641 A1 2, 2004 Barone et al. “Spray N Go Sunblock” data sheet (2003), Floratech U.S. Patent Feb. 23, 2016 Sheet 1 of 4 US 9,265,711 B2 aggil Be A3S s3 pleife. U.S. Patent US 9.265,711 B2 ?? "F~~~–——————……–……..…._________________suo|||||||| 009'?. U.S. Patent Feb. 23, 2016 Sheet 3 of 4 US 9,265,711 B2 | ----~~~~|~~~~~~~~~~~*** *º**********************-----~--~~~~--~~~**--~--~--~--~-------„… f(EJIS 33 LIEufe. U.S. Patent Feb. 23, 2016 Sheet 4 of 4 US 9,265,711 B2 --Aisa Catal 2: EC Fagance C 3-Alsacort 95% ECFalaics & Scintight Corals: COOOOOOOO) ; 1,000,000,099 s RCGOOOOO MNS HR t. SR Title US 9,265,711 B2 1. 2 COSMETIC COMPOSITION WITH shower gels, shower oils, bath products, foam baths, per WATERTIGHT FRAGRANCE fumes, aftershaves, shaving balms, face lotions, hair condi tioners, skin gels, deodorants, detergents etc. At the same CROSS REFERENCE TO RELATED time, further cosmetic auxiliaries and carrier Substances as APPLICATIONS they are commonly used in Such preparations can be used, as well as further active agents. Auxiliaries include e.g. preser This Continuation Application is a Continuation of U.S. Vatives, colourants, polyols, esters, electrolytes, gel-forming patent application Ser. No. 13/014,831, filed Jan. 27, 2011, agents, polar and non-polar oils, polymers, further copoly which is a continuation application of U.S. application Ser. mers, stabilizers, Surface-active agents. No. 1 1/362,512 filed Feb. 27, 2006 which claims priority to 10 Cosmetic active agents include e.g. organic Sunscreens, International Application No. PCT/EP2005/000931 filed Jan. Scavengers, moisturizing Substances, Vitamins, enzymes, 26, 2005, which claims priority to German Application No. plant-based active agents, polymers, antioxidants, anti-in DE 10 2004 005 095.3 filed Jan. 27, 2004 and to U.S. Provi flammatory natural active agents. sional Application No. 60/600,018, filed Aug. 29, 2004, all of Preferred cosmetic fragrances are oil-soluble fragrances which are incorporated by reference in their entirety herein. 15 such as all fragrance oils which are known for the skilled in The present invention refers to a cosmetic composition the art. which, in particular, enables the perfume component to resist The hydrophobic, alcohol-soluble, carboxylated acrylates/ wash off by water and sweat and to remain fixed on the skin octylacrylamide copolymer used according to the invention is for a long time (fragrance-watertight composition). soluble in ethanol, isopropanol and fatty alcohols. It can be It is known to encapsulate perfume oils in liposomes or made water-soluble or dispersible in water by neutralizing the cyclodextrins to achieve a controlled release of these oils. carboxy groups with water-soluble bases Such as triethanola Several systems have also been used to improve bonding to mine, Sodium carbonate, aminomethylpropanol, potassium the skin or to extend the time the perfume lasts, e.g. chitin hydroxide or ammonium hydroxide. It can thus be easily derivatives, quaternary chitosans, silicate materials and ther washed off the skin with soap, if necessary. Due to the inter moplastic polyamides. 25 action of the copolymer with the hydrolyzed jojoba ester, U.S. Pat. No. 6,143,353 A discloses the coating of phar which ester is soluble in the aqueous-alcoholic system and in maceutically active ingredients as well as fragrant compo glycol, and the solvent, fragrant molecules are integrated into nents with an aqueous dispersion of a plasticized, hydropho a complex and remain bonded to the skin for a very longtime. bic acrylic polymer, which acrylic polymer is an (alkyl) ester At the same time, the aforesaid complex has a strong water of acrylic/methacrylic acid. 30 repellent effect. Thus a very good endurance of the fragrant U.S. Pat. No. 6,172,037 B1 discloses perfume-fixing sub molecules on the skin is achieved during rain, Sweat, Swim stances comprising polyvinylpyrrolidone, hydroxy-propyl ming, etc. cellulose and a hydrophobic oil. A preferred copolymer is Acrylates Octylacrylamide The object of the present invention is to provide a cosmetic Copolymer with an acidity of 2.4 med/g. Such a product is composition which is wash-off resistant by water and at the 35 available under DERMACRYL(RAQF or DER same time ensures that the perfume component remains fixed MACRYL(R)79 by National Starch and Chem. Comp., NJ, on the skin for a long time. USA. A further object of the invention is to provide a cosmetic A preferred hydrolyzed jojoba ester is one of plant origin composition with reduced fragrance content and a feeling of (Simmondsia chinensis) having a saponification value the fragrance by the consumer without any difference. 40 according to AOCS Cd 3-25* of max.