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The Two Tonttitulu Muutunumurtin

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The Two Tonttitulu Muutunumurtin THETWO TONTTITULUUS 20170319462A1 MUUTUNUMURTIN ( 19) United States (12 ) Patent Application Publication ( 10) Pub . No. : US 2017/ 0319462 A1 Marchant et al. (43 ) Pub . Date : Nov . 9 , 2017 ( 54 ) THERMOPLASTIC POLYURETHANE FILM Publication Classification FOR DELIVERY OF ACTIVE AGENTS TO (51 ) Int. Ci. SKIN SURFACES A61K 8 / 87 (2006 . 01 ) A610 19 /02 (2006 .01 ) (71 ) Applicant: Lubrizol Advanced Materials , Inc. , A61K 47 /34 ( 2006 .01 ) Cleveland , OH (US ) A61K 9 / 70 ( 2006 .01 ) A61K 9 / 00 ( 2006 . 01 ) (72 ) Inventors : Nancy S . Marchant, Medina , OH A61K 8 / 73 ( 2006 .01 ) (US ) ; Pallavi Kulkarni, Woburn , MA A61K 8 /64 (2006 .01 ) (US ) ; Anthony J . Walder, Essex , MA A61K 8 /42 ( 2006 .01 ) A61K 8 / 368 ( 2006 . 01 ) (US ) ; Paul M . Basone, Akron , OH A610 19 / 08 (2006 .01 ) (US ) ; Shawn Lankowski, Denvers, MA A61K 8 / 34 (2006 .01 ) (US ) ; Juan Cebrián Puche , Gava ( ES) ; ( 52 ) U . S . Cl. Sandra Mendez , Gava (ES ) ; Mireia CPC . .. .. .. A61K 8 / 87 ( 2013 .01 ) ; A610 19 / 08 Martin , Gava ( ES ) ( 2013 .01 ) ; A610 19 / 02 (2013 .01 ) ; A61K 47/ 34 ( 2013 .01 ) ; A61K 9 / 7007 ( 2013 . 01 ) ; A61K 8 / 34 ( 21 ) Appl. No. : 15/ 520 , 661 ( 2013 . 01 ) ; A61K 8 / 735 (2013 .01 ) ; A61K 8 /64 ( 2013 .01 ) ; A61K 8 / 42 ( 2013 .01 ) ; A61K 8 / 368 (22 ) PCT Filed : Oct . 23 , 2015 ( 2013 .01 ) ; A61K 9 /0014 ( 2013 .01 ) ( 86 ) PCT No. : PCT/ US2015 / 057084 (57 ) ABSTRACT $ 371 ( c ) ( 1 ) , A polymer film suited to use as a face mask or transdermal ( 2 ) Date : patch includes at least 30 wt. % of a thermoplastic polyure Apr. 20 , 2017 thane polymer which is the reaction product of a first polyether polyol having a molecular weight of at least 3000 daltons, optionally , a second polyether polyol having a Related U . S . Application Data molecular weight of no more than 2500 daltons, at least one (60 ) Provisional application No . 62/ 220 ,552 , filed on Sep . of a third polyol having a molecular weight of up to 800 18 , 2015 , provisional application No . 62 /073 ,314 , daltons , and a chain extender , a diisocyanate , optionally, a filed on Oct. 31 , 2014 . catalyst. The film includes up to 5 wt. % water. 102 14 - 0 0000 0000 000 000 0 . 000000000000 0 . 000000 800000000000000 , 0000 9000 000 900000080000 000 000 00X00000000000000 88 0 . 00 . 000 .000 . 000 20 Patent Application Publication Nov . 9 , 2017 Sheet 1 of 10 US 2017 /0319462 A1 102 16 Fig. 1 18 000000000000000000000000000000000000000000000000000000000000000000000000000000000 OBO000 000 000 0000 008RO MASAŽUOSIAL8500000000000000000 0800 002000 614 . 2 Patent Application Publication Nov. 9 , 2017 Sheet 2 of 10 US 2017/ 0319462 Al I8 2 32 Oo do oc0000 dou08ooo da Q009es 9000 00080p 000 i doo0290000000000 doggogo909 0003 00000000 0000000 ?????Fig. 3 20 Patent Application Publication Nov . 9 , 2017 Sheet 3 of 10 US 2017 /0319462 A1 70 60 50 Fig.4 EX.FRATEOFSWELL MINUTES 30 20 600% 500% 400% 300% 200% 100% 0% UP PICK % WT Patent Application Publication Nov . 9 , 2017 Sheet 4 of 10 US 2017 /0319462 A1 0.40.4 EX.A XEX.F IEX.B AEX.C Lex 0:30.3 COMPARISONOFBUFFERUPTAKE 0.2DRYFILMTHICKNESS,INmm Fig.5 D.IORYFILMTHORESINmm 0.1 0%+ 1000% -2006 +%008 700% 300% 200% +%001 UPTAKE SOLUTION %WT Patent Application Publication Nov . 9 , 2017 Sheet 5 of 10 US 2017 /0319462 A1 ATUMCORNEUM III11 IIIIIIIIII ITITITO FLUIDRECEPTOR IIIIIIIII TIITLILIT EPIDERMIS TITUT 24H III 111 Ult O AVDERMIS TL11 IIII EDI 1.8%CAFFEINESOLUTION MINT IIIIIIIII IIIIIIIII LLLLLLLL ILLITTII IIIIIIIII ULIUUULIL (GUIDELINEAMOUNT) 1.8%CAFFEINESOLUTION Fig.6 TIIMI IIIIIIII III IIIIIIII IIIIIIII WILTTI U1LLLL 1.8%CAFFEINE SOLUTION ???????????????????????????? IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII POLYMERHYDROGEL+ IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIILLLLLLLLLLLLLLLLLLLLLLLLLL 1.8%CAFFEINE o o W 0 - M ) cm / ugO ( PENETRATIONI A SKIN Patent Application Publication Nov . 9 , 2017 Sheet 6 of 10 US 2017 /0319462 A1 FLUIDRECEPTORDRECEPTOR STRATUMCORNEUM 1 1 1 1 11 DERMIS EPIDERMIS 1 1 1 1 1 IIIII 1111 IIIIII BIOCELLULOSE+1.8%CAFFEINE LOTT | 1 | 1 1 1 1 LTL 11 11 111 1 1 1 1 AVDERMIS 1 I 111 1 1 1 1 III It TI TTI O Fig.7 IIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIII LLLLLLLLLLLLLLLLILIIT IIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIII III IIIIIIIIIIIIIIIIIIIIIIIIII POLYMER+1.8%CAFFEINE IIIIIIIIIIIIIIIIIIIIIIII 111TITUITULIITTOLIITIT TIILILOTULIITTO w PENETRATIO SKIN Patent Application Publication Nov . 9 , 2017 Sheet 7 of 10 US 2017 /0319462 A1 RECEPTORFLUID STRATUMCORNEUM ITD LITTVILA EPIDERMIS LIIT T 111 II LIIT 11111 ILT III 1 III IIIII 1111 OTT simoAV LILIT 1TTU LIIT 1 1 1 1 IT 11 Z III PALMITATESOLUTION II 11 ME 2%DIMETHYLMETHOXYCHROMANYL Fig.8 IIIIIIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIIII # 11 IIIIIIIIIIIIIIIIIIIIIIIIIIII 1 1 1 1 1 1 1 IIIIIIIIIIIIIIIIIIII TUILLITTUITITUUTTITULLI IIIIIIIIIIIIIIIIIIIIIIIIIIII ! IIIIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIIII 1 1 1 1 1 IIIIIIIIIIIIIIIIIIIIIIII IIIIIIIIIIIIIIIIIIIIIIIIIIII ! POLYMER+2%DIMETHYLMETHOXY CHROMANYLPALMITATE +00° 900 5.00 00 3.00 2.00 0.00 )? cm / mg( PENETRATION SKIN Patent Application Publication Nov . 9 , 2017 Sheet 8 of 10 US 2017 /0319462 A1 SCNE+0 SOLUTION FILML Fig.9 FILMD HA FILMK 0 0 0 A W ru - o ) % ( PERMEATED3 ACID SALICYLLIC Patent Application Publication Nov . 9 , 2017 Sheet 9 of 10 US 2017 /0319462 A1 28 2024 16 TIME(n) Fig.10 12 E o ACOMMERCIALPATCH ET •FILMK OFILMD 4-20 I to 25 ? o ) % ( PERMEATEDL HCT LIDOCAINE Patent Application Publication Nov . 9 , 2017 Sheet 10 of 10 US 2017 /0319462 A1 82 82_ 24 20 16 TIME(h) Fig.11 21 HO FILMK ACOMMERCIALPATCH OFILML ? 2 ? 1 - ) % ( PERMEATED3 SODIUM DICLOFENAC3 US 2017 /0319462 A1 Nov . 9 , 2017 THERMOPLASTIC POLYURETHANE FILM BRIEF DESCRIPTION FOR DELIVERY OF ACTIVE AGENTS TO [0007 ] In accordance with one aspect of the exemplary SKIN SURFACES embodiment, a polymer film includes at least 30 wt. % of a [0001 ] This application claims the priority of PCT / thermoplastic polyurethane polymer which is the reaction US2015 /057084 (WO 2016 / 069396 ) , filed Oct . 23 , 2015 , product of a first polyether polyol having a molecular weight U . S . Provisional Application Ser . No. 62/ 073 , 314 , filed Oct. of at least 3000 daltons , optionally , a second polyether 31 , 2014 , and U . S . Provisional Application Ser. No . 62 / 220 , polyol having a molecular weight of no more than 2500 552 , filed Sep . 18 , 2015 , from which the PCT application daltons , at least one of a third polyol having a molecular claims priority , the disclosure of each of which is hereby weight of up to 800 daltons, and a chain extender , a incorporated by reference in its entirety . diisocyanate , optionally , a catalyst ; and up to 5 wt. % water. [0008 ]. In accordance with another aspect of the exemplary embodiment, a method of forming a face mask or body patch BACKGROUND includes forming a thermoplastic polyurethane polymer [ 0002 ] The exemplary embodiment relates to the delivery from a first polyether polyol having a molecular weight of at of active agents to skin surfaces and finds particular appli least 3000 daltons, optionally , a second polyether polyol cation in connection with a thermoplastic polyurethane film having a molecular weight of no more than 2500 daltons , that serves as a vehicle for skin treatment active agents and and at least one of a third polyolhaving a molecular weight a face mask or body patch formed from the film . of up to 800 daltons and a chain extender . The method [0003 ] Face masks have been traditionally used for pro further includes casting the thermoplastic polyurethane viding active agents to the face and other skin surfaces. The polymer with an active agent in solution to form a cast film active agents may include vitamins , moisturizers , cleansers , which includes the active agent dispersed in the thermoplas anti - wrinkle agents , lightening agents , skin toning agents , tic polyurethane polymer . and others . [0009 ] In accordance with another aspect of the exemplary [0004 ] Conventional face masks include hydrocolloid lay embodiment, a face mask or body patch includes a hydrated ers containing the active agents and other nutrients . The film which includes at least 50 wt. % water , 5 to 30 wt. % hydrocolloid layers are often held together by fabric or a of a thermoplastic polyurethane polymer , and at least one synthetic mesh which provides a physical and mechanical active agent. support. Such multi - layered face masks tend to be time consuming and costly to manufacture . Hydrocolloid face BRIEF DESCRIPTION OF THE DRAWINGS masks are typically formed by hot solution casting of a [0010 ] FIG . 1 is a schematic top plan view of a face mask ; mixture of polysaccharide polymers such as carrageenan , [0011 ] FIG . 2 is a side sectional view of a hydrated face locust bean gum (galactomannans ) , agarose , agar , and xan mask on the skin of a wearer ; than gum . Generally the polysaccharide components are [ 0012 ]. FIG . 3 illustrates a body patch ; added to a mixture of water , glycerin , and polypropylene [0013 ]. FIG . 4 illustrates rate of swell for an exemplary glycol and heated to approximately 80 to 90° C . to dissolve polyurethane film ; the polymer and obtain a molten state . The colloid solution [ 0014 ] FIG . 5 illustrates buffer uptake for different poly is cooled to about 60° C . and the cosmetic additives are urethane films at different thicknesses ; added . This intermediate cooling step is to avoid harming [0015 ]. FIG . 6 illustrates percutaneous absorption by pig temperature - sensitive active agents . The thickened solution skin of 1 . 8 % caffeine solution loaded on an exemplary is cast as a film with a knife at a set thickness . A rayon polymer film ; reinforcing material may be added . The solution is then [ 0016 ] FIG . 7 shows percutaneous absorption by pig skin cooled to 25° C . and kept between release films until the film of a 1 . 8 % caffeine solution loaded on an exemplary polymer sets to a firm gel before cutting to shape . The final gel film film and on biocellulose (microbial cellulose ) ; thickness is between 0 .
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