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WO 2017/108725 Al 29 June 2017 (29.06.2017) P O P C T

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WO 2017/108725 Al 29 June 2017 (29.06.2017) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/108725 Al 29 June 2017 (29.06.2017) P O P C T (51) International Patent Classification: Bebington, Wirral Merseyside CH63 3JW (GB). A61K 8/26 (2006.01) A61K 8/88 (2006.01) THOMPSON, Katherine, Mary; Unilever R&D Port A61K 8/11 (2006.01) A61K 9/48 (2006.01) Sunlight Quarry Road East, Bebington, Wirral Merseyside A61Q 15/00 (2006.01) CUD 3/50 (2006.01) CH63 3JW (GB). A61K 8/84 (2006.01) (74) Agent: WHALEY, Christopher; Unilever PLC, Unilever (21) International Application Number: Patent Group Colworth House, Sharnbrook, Bedford Bed PCT/EP2016/081814 fordshire MK44 1LQ (GB). (22) International Filing Date: (81) Designated States (unless otherwise indicated, for every 19 December 2016 (19. 12.2016) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (25) Filing Language: English BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, (26) Publication Language: English DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, (30) Priority Data: KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, 15201732.3 2 1 December 201 5 (21. 12.2015) EP MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, 15201749.7 2 1 December 201 5 (21. 12.2015) EP NL NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, (71) Applicant (for AE, AG, AU, BB, BH, BN, BW, BZ, CA, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, CY, EG, GB, GD, GH, GM, IE, IL, IN, KE, KN, KW, LC, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, LK, LS, MT, MW, MY, NA, NG, NZ, OM, PG, QA, RW, SA, ZA, ZM, ZW. SC, SD, SG, SL, SZ, TT, TZ, UG, VC, ZA, ZM, Z W only): (84) Designated States (unless otherwise indicated, for every UNILEVER PLC [GB/GB]; Unilever House, 100 Victoria kind of regional protection available): ARIPO (BW, GH, Embankment, London Greater London EC4Y 0DY (GB). GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant (for all designated States except AE, AG, AU, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, BB, BH, BN, BW, BZ, CA, CY, EG, GB, GD, GH, GM, IE, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, IL, IN, KE, KN, KW, LC, LK, LS, MT, MW, MY, NA, NG, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, NZ, OM, PG, QA, RW, SA, SC, SD, SG, SL, SZ, TT, TZ, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, UG, US, VC, ZA, ZM, ZW): UNILEVER N.V. [NL/NL]; SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Weena 455, 3013 AL Rotterdam (NL). GW, KM, ML, MR, NE, SN, TD, TG). (71) Applicant (for US only): CONOPCO, INC., d b/a UNI¬ Declarations under Rule 4.17 : LEVER [US/US]; 800 Sylvan Avenue AG West, S. Wing, — as to applicant's entitlement to apply for and be granted a Englewood Cliffs, New Jersey 07632 (US). patent (Rule 4.1 7(H)) (72) Inventors: BARNETT, Stuart, Anthony; Unilever R&D — as to the applicant's entitlement to claim the priority of the Port Sunlight Quarry Road East, Bebington, Wirral Mer- earlier application (Rule 4.1 7(in)) seyside CH63 3JW (GB). JONES, Craig, Warren; Uni — of inventorship (Rule 4.17(iv)) lever R&D Port Sunlight Quarry Road East, Bebington, Wirral Merseyside CH63 3JW (GB). KHOSHDEL, Ezat; Published: Unilever R&D Port Sunlight Quarry Road East, Bebington, — with international search report (Art. 21(3)) Wirral Merseyside CH63 3JW (GB). MERRINGTON, James; Unilever R&D Port Sunlight Quarry Road East, (54) Title: METHOD OF DELIVERING AN ACTIVE AGENT TO SKIN (57) Abstract: A method of delivering an active agent to skin, preferably axilla, comprising the steps of: a) applying to skin an anti perspirant composition comprising an antiperspirant (AP) active selected from astringent active salts comprising aluminium, zirconi - um and mixed aluminium /zirconium salts and at least 0.1 wt% of core shell microcapsules whereby the microcapsules come into contact with the skin each microcapsule having an inner shell formed of a first synthetic polymer and containing the active agent and the inner shell capable of allowing at least a portion of the active agent to pass from inside the inner shell to outside the inner shell to 00 enable it to come into contact with the skin, the inner shell being coated with a coating of insoluble polyamide with a solubility in o water of less than 1 g/L at 25°C, the polyamide formed by the reaction of: (i) at least one low molecular weight dicarboxylic acid having from 3 to 12 carbon atoms, or ester thereof; (ii) at least one poly(alkylene glycol) polyamine having the formula (I) H 2N-(- C(R)H -CH2-0-)x-C(R)H -CH2-NH2 (I) where x ranges from about 2 to 5, R is an alkyl of one to four carbon atoms; (iii) optionally, at o least one high molecular weight dicarboxylic acid (dimer) having from 20 to 40 carbon atoms, or ester thereof; and wherein the coat ing further comprises a crosslinker to improve hardness and further reduce solubility, such that, while the coating is present the re - lease of the active agent onto the skin is retarded; b) sweating to produce sweat that comes into contact with at least part of the poly o amide coating and the antiperspirant active; c) degrading the polyamide coating by the action of protease enzymes present in the sweat thereby to cause delayed release of the active agent onto the skin after the microcapsule first comes into contact with sweat. METHOD OF DELIVERING AN ACTIVE AGENT TO SKIN Field of the Invention The present invention relates to a method of delivering an active agent, preferably perfume, to skin using microcapsules which release the active agent after their exposure to protease. Background and Prior Art It has been proposed to design core shell microcapsules to release an active agent as a triggered response of exposure of the shell to enzymes, including those enzymes that naturally occur on skin. US 2008/02741 49 (Evonik) discloses cosmetic skin treatment compositions containing microcapsules that give controlled release of active ingredients on skin by means of enzymatically degradable organic polymers containing ester linkages triggered to release by lipases. We have found that naturally occurring levels of lipases are unreliable as a trigger for skin applications. W O 2009/126742 (Appian Labs) discloses the release of active ingredients from microcapsules by exposure to metalloproteinase. The microcapsules are coated in crosslinked gelatin which then releases the microcapsules in a controlled manner on exposure to the metalloproteinase that is found at specific sites in an organism to be treated. The technology thus provides targeted release. Crosslinked gelatin is unsuitable as a coating material because it is moisture sensitive and thus very limited in terms of the formulations into which it can be added. Also the most common crosslinkers are chemicals that are undesirable for skin contact (e.g. glutaraldehyde). Furthermore aldehyde cross-linked gelatin coacervate capsules can show a high degree of fragrance leakage during storage and are relatively soft and so can be mechanically prematurely ruptured. W O 201 5/01 4628 (Unilever) discloses a deodorant spray containing a particle with an insoluble enzymatically degradable shell. Two degradation mechanisms are disclosed, one utilising lipase and one utilising protease. Among the shell materials that can be degraded by proteases nylon or polyamide is taught. We have since determined that nylons are not sufficiently degraded to be of practical utility as triggered release shells. This document also discloses the possibility to form a secondary coating from any of the shell materials taught. No details are given of the coating material or the particle onto which it is to be coated. It has been proposed to use polyamides as an encapsulation or microcapsule coating material. Typically this material is mentioned as an alternative but is not the main focus of patent documents. The following documents disclose polyamide microcapsules which utilise polyoxyamines as a monomer, but not for any kind of biotriggering benefit: US 2002/01 58356 (Institut Francais Petrole) discloses microcapsules made by reaction of acid chlorides (e.g. adipoyl chloride) with polyoxylyeneamine (Jeffamines). According to paras 0053 and 0059 PO is preferred over EO for the latter material. The resulting capsules are over 100 micron diameter. US 4777089 (Lion) discloses core shell microcapsules, possibly containing perfume in the core, using a water-soluble nylon for the shell AQ Nylon P70 is a copolymer of 1-6 hexadioic acid with α,ω -diethylamine-PEG (CAS 24991 -53-5) and caprolactam. The water soluble nylon shell is removed on dilution. Sweat and saliva are mentioned as diluents. JP 2012/1 7 1974 (Sekisui Plastics) discloses microspheres comprising water-soluble polyamide coating layers (AQ-Nylon T70) around (polystyrene) solid resin particles. The delivery of the polyamide from aqueous solution is said to be more environmentally friendly than from another solvent system. The following documents disclose other polyamide shell or polyamide coated microcapsules, but not for any kind of biotriggering benefit: US 4835248 (Hoechst, 30/05/1 989) discloses sparingly soluble polyamide microcapsules comprising biodegradable polymers of a dicarboxylic acid and a diamine (with carboxy- substitutent).
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