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Cosmetic Compositions with Tricyclodecane Amides Kosmetische Zusammensetzungen Mit Trizyklodekanamiden Composition Cosmétique Contenant Les Amides De Tricyclododecane

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Cosmetic Compositions with Tricyclodecane Amides Kosmetische Zusammensetzungen Mit Trizyklodekanamiden Composition Cosmétique Contenant Les Amides De Tricyclododecane (19) TZZ Z _T (11) EP 2 969 026 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 8/06 (2006.01) 01.11.2017 Bulletin 2017/44 A61K 8/365 (2006.01) A61Q 17/04 (2006.01) C07D 211/16 (2006.01) C07D 307/22 (2006.01) (2006.01) (2006.01) (21) Application number: 14708585.6 C07D 217/06 C07D 215/08 C07C 233/58 (2006.01) C07D 211/66 (2006.01) C07D 211/60 (2006.01) C07D 211/62 (2006.01) (22) Date of filing: 10.03.2014 C07D 205/04 (2006.01) C07D 207/06 (2006.01) A61K 8/04 (2006.01) A61K 8/368 (2006.01) A61K 8/42 (2006.01) A61K 8/37 (2006.01) A61K 8/49 (2006.01) A61K 8/63 (2006.01) A61Q 19/00 (2006.01) (86) International application number: PCT/EP2014/054604 (87) International publication number: WO 2014/139963 (18.09.2014 Gazette 2014/38) (54) COSMETIC COMPOSITIONS WITH TRICYCLODECANE AMIDES KOSMETISCHE ZUSAMMENSETZUNGEN MIT TRIZYKLODEKANAMIDEN COMPOSITION COSMÉTIQUE CONTENANT LES AMIDES DE TRICYCLODODECANE (84) Designated Contracting States: • CLOUDSDALE, Ian Stuart AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Chapel Hill, North Carolina 27516 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • AU, Van PL PT RO RS SE SI SK SM TR Trumbull, Connecticut 06611 (US) • LEE, Jianming (30) Priority: 13.03.2013 US 201361778831 P Trumbull, Connecticut 06611 (US) • DICKSON, JR, John Kenneth (43) Date of publication of application: Apex, North Carolina 27523 (US) 20.01.2016 Bulletin 2016/03 (74) Representative: Corsten, Michael Allan (73) Proprietors: Unilever N.V. • Unilever PLC Unilever Patent Group London, Greater London EC4Y 0DY (GB) Olivier van Noortlaan 120 Designated Contracting States: 3133 AT Vlaardingen (NL) CY GB IE MT • Unilever N.V. (56) References cited: 3013 AL Rotterdam (NL) EP-A1- 0 199 636 WO-A1-2005/019162 Designated Contracting States: WO-A1-2008/054144 ES-A1- 2 296 463 AL AT BE BG CH CZ DE DK EE ES FI FR GR HR US-A- 5 212 203 HU IS IT LI LT LU LV MC MK NL NO PL PT RO RS SE SI SK SM TR (72) Inventors: • HARICHIAN, Bijan Trumbull, Connecticut 06611 (US) • MOADDEL, Teanoosh Trumbull, Connecticut 06611 (US) 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 2 969 026 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 969 026 B1 • WEBSTER ET AL: "Discovery and biological Remarks: evaluation of adamantyl amide 11beta-HSD1 Thefile contains technical information submitted after inhibitors", BIOORGANIC & MEDICINAL the application was filed and not included in this CHEMISTRY LETTERS, PERGAMON, specification AMSTERDAM, NL, vol. 17, no. 10, 27 April 2007 (2007-04-27), pages 2838-2843, XP022049598, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2007.02.057 • GABRIEL SCHÄFER ET AL: "Facile Synthesis of Sterically Hindered and Electron-Deficient Secondary Amides from Isocyanates", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 51, no. 36, 3 September 2012 (2012-09-03), pages 9173-9175, XP055120011, ISSN: 1433-7851, DOI: 10.1002/anie.201204481 2 EP 2 969 026 B1 Description Field of the Invention 5 [0001] The present invention is directed to a cosmetic composition and method for stabilizing the composition with a tricyclodecane amide. The tricyclodecane amide unexpectedly enhances the solubility of solid agents within liquid agents of the composition and results in a superior cosmetic composition suitable for topical use by consumers. Background of the Invention 10 [0002] A large number of solid agents used in cosmetic compositions, for example, often have low solubilities in solvents or liquid agents, and thus a tendency to recrystallize rapidly within the compositions. Recrystallization of solid cosmetic agents, not only negatively impacts the performance of the cosmetic composition but also can result in a grainy composition having inferior sensory attributes. 15 [0003] With sunscreens, for example, in order to achieve good protection, excessively large proportions of oily solvents are often needed to enhance solubility of the sunscreen. This approach, however, invariably yields a final cosmetic composition that delivers an oily or greasy feel that is not typically enjoyed by consumers. [0004] Another technique employed to prevent solid agent recrystallization in compositions is encapsulation. Encap- sulation, nevertheless, can be expensive and prevents solubilization of solid agent within a composition (like a cosmetic 20 composition). As a result of this, it is often observed that less agent (e.g., active) is delivered through skin when the same is encapsulated and applied topically. [0005] There is an increasing interest to develop cosmetic compositions for topical application that minimize recrys- tallization in the absence of encapsulation. Moreover, there is an increasing interest to enhance solubility of solid agents within compositions so that a maximum amount of such agents may be delivered topically to consumers from cosmetic 25 compositions. This invention, therefore, is directed to stabilized cosmetic compositions that comprise a tricyclodecane amide. The tricyclodecane amide unexpectedly enhances solubility of solid agents in liquid agents within the composi- tions. The enhancement of solid agent solubility is surprisingly achieved while simultaneously delivering compositions that yield excellent sensory benefits upon topical application. Although not wishing to be bound by this theory, it is believed that tricyclodecane amides have a unique cage structure, which renders them small and bulky, therefore allowing 30 them to disturb the ordered packing and formation or growth of crystals. Also as part of the present invention it has been discovered that tricyclodecane amides themselves have cosmetic benefits, such as sebum suppression and boosting UV-A, UV-B, and SPF performance of common sunscreen agents. Additional Information 35 [0006] Efforts have been disclosed for increasing the solubility of benefit agents within a cosmetic composition. In United States Patent Application No. 2006/0024337 A1, a process is described for dissolving lipophilic compounds with amphiphilic block copolymers in cosmetic compositions. Other efforts have been described for enhancing benefit agent deposition within personal wash compositions. In U.S. Patent No. 6,576,228 B1, personal wash compositions with water- 40 soluble compounds for providing enhanced SPF are described. Still other efforts have been disclosed for enhancing benefit agent deposition. In U.S. Patent No. 6,399,045 B1, liquid personal wash compositions with benefit agent and cationic polymers are described. [0007] Tricyclodecane derivatives, and in some cases tricyclodecane amides, have been described. See for instance Kilburn et al., US Patent 8,053,431B2; WO2004/089415A2 (Novo Nordisk A/S); WO2004/089416A2 (Novo Nordisk A/S); 45 Narula et al., US 4,985,403; Mathonneau, US 2006057083; WO06/119283 (Hunton & Williams LLP); WO08/054144 (Amorepacific Corporation). Summary of the Invention 50 [0008] The present invention includes a cosmetic composition precursor comprising: a) a tricyclodecane amide; b) a solid agent; c) a liquid agent; 55 d) wherein both the solid agent and the liquid agent is a cosmetic benefit agent; and e) wherein solid agent to liquid agent weight ratio is in the range from about 0.001 to about 1. [0009] The present invention also includes a cosmetic composition comprising the cosmetic composition precursor. 3 EP 2 969 026 B1 [0010] The present invention also includes a method of delivering a solid cosmetic agent topically to the skin of a consumer with the composition of this invention. [0011] "Solid agent", as used herein, means an agent (e.g., mixture, compound) that is a solid at room temperature (melting point above 20°C), such solid agent having a partition coefficient (Log Po/w) from about -5 to about 15. 5 [0012] "Cosmetic benefit agent", as used herein, means a component or benefit agent that improves a characteristic of teeth, a skin or hair characteristic and/or benefits teeth, skin or hair wherein the same can be, and preferably, is an active in a cosmetic composition, and most preferably, in a topical cosmetic composition classified as a dentifrice, mouthwash, cream (including vanishing), lotion, balm, deodorant, gel, make-up composition, body wash, shampoo or conditioner. 10 [0013] "Liquid agent," as used herein, means an agent (e.g., mixture, compound) that is a liquid at room temperature (melting point below 20°C), such liquid agent having a partition coefficient (Log Po/w) from about -0.75 to about 15. [0014] The octanol-water partition coefficient for solid and liquid agents can be obtained from a variety of published sources such as CRC Handbook of Physics and Chemistry or through the use of on-line software such as ChemSpider. The values reported for Log P of solid and liquid agents in this invention were taken from the on-line ChemSpider source. 15 [0015] Both the solid agent and the liquid agent is a cosmetic benefit agent as described herein. Solid agent and liquid agent are not meant to include agents or ingredients used solely to produce a cosmetic carrier or chassis such as water, polymeric thickeners such as polyacrylates, Aristoflex AVC, silicon containing polymers, emulsifiers, opacifiers, micro- spheres such as those supplied by Kobo Products Inc. examples include polymethylmethacrylate e.g. BPA-500, ethyl- ene/methacrylate copolymers e.g. EA-209, Nylon series such as Nylon-6 e.g. TR-1, Polyethylene e.g. CL2080, polymeth- 20 ylsilsesquioxane e.g.
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