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WO 2012/158483 A2 22 November 2012 (22.11.2012) P O P C T

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WO 2012/158483 A2 22 November 2012 (22.11.2012) 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 2012/158483 A2 22 November 2012 (22.11.2012) P O P C T (51) International Patent Classification: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, C09J 11/00 (2006.01) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, (21) International Application Number: KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, PCT/US20 12/037429 MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (22) International Filing Date: OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, 11 May 2012 ( 11.05.2012) SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 61/486,379 16 May 201 1 (16.05.201 1) US UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (71) Applicant (for all designated States except US) : AVERY EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, DENNISON CORPORATION [US/US]; 150 N. Orange MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, Grove Blvd., Pasadena, CA 9 1103 (US). TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). (72) Inventors; and (75) Inventors/Applicants (for US only): WIBAUX, Anne, Declarations under Rule 4.17 : Marie [FR/BE]; Avery Dennison Corporation, 150 N. Or — as to applicant's entitlement to applyfor and be granted a ange Grove Blvd., Pasadena, CA 9 1103 (US). JOHNSON, patent (Rule 4.1 7(H)) Peter [US/US]; Avery Dennison Corporation, 150 N. Or ange Grove Blvd., Pasadena, CA 9 1103 (US). — as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.1 7(in)) (74) Agents: BEMBENICK, Brian, G. et al; Avery Dennison Corporation, 8080 Norton Parkway, 22-d, Mentor, OH Published: 44060 (US). — without international search report and to be republished (81) Designated States (unless otherwise indicated, for every upon receipt of that report (Rule 48.2(g)) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, < 00 o (54) Title: ADHESIVE CONTAINING MICROPARTICLES (57) Abstract: Methods for forming and incorporating microparticles containing one or more active agents into adhesives are de scribed. The methods involve spray drying a liquid of the one or more active agents and obtaining the active agent in a particulate form. The dry powder is then blended or otherwise incorporated with the adhesive of interest. Also described are various medical products utilizing the adhesive and one or more active agents in microparticle form, and related methods of use. ADHESIVE CONTAINING MICROPARTICLES CROSS REFERENCES TO RELATED APPLICATIONS [0001] The present application claims the benefit of U.S. Provisional Patent Application No. 61/486,379 filed May 16, 2011, which is incorporated herein by reference in its entirety. FIELD [0002] The present invention relates t o ad hesives containing microparticles of one or more active agents, methods for incorporating microparticles of actives into an adhesive, and products using such adhesives. BACKGROUND [0003] A wide array of medical products use adhesive for affixing the product onto a user's skin. As will be appreciated, it is desira ble to include one or more active agents such as antimicrobial agents in the medical product or ad hesive to prevent or at least minimize microbial growth or reproduction along the skin, as such can readily lead t o infection and other undesira ble conditions. [0004] Accordingly, artisans have attempted t o incorporate a wide range of antimicrobial agents into medical products or materials. Although certain agents have been incorporated into adhesives, effective incorporation into an adhesive composition presents a formida ble technical challenge. It is difficu lt to efficiently disperse such agents within the adhesive. Furthermore, certain antimicrobial agents undergo a loss in efficacy upon incorporation in an ad hesive formulation due t o the presence of solvents or other components in the adhesive. [0005] Accordingly, it would be desira ble to provide a method for incorporating one or more active agents and particularly an antimicrobial agent into an adhesive formulation such that the agent is effectively dispersed and retains its efficacy when residing in the adhesive. SUMMARY [0006] The difficulties and drawbacks associated with previously known compositions, products, and practices are addressed in the present methods, adhesive compositions, products using such compositions and related methods of use. [0007] In one aspect, the present su bject matter provides an adhesive composition comprising an adhesive and microparticles dispersed in the adhesive. The microparticles include a matrix material and at least one active agent. [0008] As will be realized, the su bject matter is capa ble of other and different embodiments and its several details are capa ble of modifications in various respects, all without departing from the invention. Accordingly, the description is to be regarded as illustrative and not restrictive. DETAILED DESCRIPTION OF THE EMBODIMENTS [0009] The present su bject matter generally provides an adhesive composition comprising microparticles that include one or more active agents. The present su bject matter also provides various methods relating to the preparation of the ad hesives and microparticles, and various products using such ad hesives. Active Agents and Forming Microparticles [0010] A wide array of one or more active agents can be incorporated in the adhesives described herein. Preferably, the active agents are hydrophilic. Non-limiting examples of preferred active agents include benzocaine, procaine hydrochloride, tetracaine, tetracaine hydrochloride, dibucaine, lidocaine, lidocaine hydrochloride, bupivicaine, dyclonin, etidocaine, mepivicaine, butamen picrate, dimethisoquin hydrochloride, cyclomethylcaine sulfate, and the like; analgesics and anti-inflammatory agents such as buprenorphin, butophanol tartrate, acetaminophen, fentanyl, mefenamic acid, flutenamic acid, diclofenac, oxyphenbutazone, phenybutazone, ibuprofen, flurbiprofen, naproxen, menthol, methyl salicylate, phenol, salicylic acid, benzyl alcohol, camphor, camphorated metacresol, juniper tar, resorcinol, allyl isothiocyanate, capsaicin, and the like; corticosteroids such as alclometasone dipropionate, amcinocide, hydrocortisone, betamethasone dipropionate, betamethasone valerate, desoximetasone, clobetasol propionate, flurandrenolide, halcinonide, halobetasol, estradiol, testosterone, progesterone, fluticasone, clobetasol, dexamethasone, dexonide, fluocinolone acetonide, flucinonide, medroxyprogesterone, mometasone furoate, triamcinolone, and the like; antibiotics such as bacitracin, bacitracin zinc, chlortetracycline hydrochloride, chlorhexadine gluconate, clindamycin, cliquinol, neomycin sulfate, polymyxin B sulfate, erythromycin, gentamicin, sulfathiazole, sulfacetamide, sulfa benzamide, oxytetracycline hydrochloride, tetracycline, and the like; antimicrobial agents such as benzalkonium chloride, chlorhexidine gluconate, hexachlorophene, mafenide acetate, nitrofurazone, nystatin, acetosulfamine, clortrimazole, povidone-iodine, and the like; antifungal agents such as amphotericin B, butoconazole, cetylpyridinium chloride, chlorxylenol, cyclopirox olamine, clioquinol, clotrimazole, sulconazole nitrate, nystatin, oxyconazole, econazole nitrate, ketoconazole, miconazole nitrate, naftifine hydrochloride, pentamycin, pyrrolinitrin, terbinafine, triacetin, and the like; debriding agents such as deoxyribonuclease, collagenolytic, debridement, fibrinolytic or proteolytic enzymes, papain, papain-urea, and the like; antihistamines such as chlorcyclizine hydrochloride, diphenylhydramine hydrochloride, tripelennamine hydrochloride, and the like; antiepileptics such as nitrazepa m, meprobamate, clonazepam, and the like; coronary vasodilators such as nitroglycerine, dipyridamole, erythritol, tetranitrate, pentaerythritol tetranitrate, propatyinitrate, and the like; dermatological agents such as retina l, retinol, retinoic acid and their derivatives, hydroxyacids, alphaketoacids, and the like; and other drugs such as benzoyl peroxide, podofilox, masoprocol, nicotine, scopolamine, nitroglycerine, fluorouracil, hydrocolloids, hydroquinone, monobenzone, tretinoin and acyclovir. Preferred drugs for use herein include acne-benzoyl peroxide, Vitamin C, and Vitamin E. [0011] Although the one or more active agent(s) incorporated in the microparticles are prefera bly hydrophilic, the su bject matter includes the incorporation of one or more active(s) that are hydrophobic, and the incorporation of a com bination of hydrophilic agents and hydrophobic agents. [0012] The microparticles may also comprise one or more matrix binder, or excipient materials. Prefera bly, the matrix materials are inert or su bstantially so. Non-limiting examples of matrix materials include binders such as saccharide binders, protein binders, and synthetic polymer binders; fillers such as plant cellu lose, dibasic calcium phosphate, vegeta ble fats and oils, sugar fillers, calcium carbonate,
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