WO2000021485B1 - Polyurethanes as topical skin protectants - Google Patents

Polyurethanes as topical skin protectants

Info

Publication number
WO2000021485B1
WO2000021485B1 PCT/US1999/023107 US9923107W WO0021485B1 WO 2000021485 B1 WO2000021485 B1 WO 2000021485B1 US 9923107 W US9923107 W US 9923107W WO 0021485 B1 WO0021485 B1 WO 0021485B1
Authority
WO
WIPO (PCT)
Prior art keywords
cancelled
polyurethane
molecular weight
skin
lower alkyl
Prior art date
Application number
PCT/US1999/023107
Other languages
French (fr)
Other versions
WO2000021485A2 (en
WO2000021485A3 (en
Inventor
Daniel A W Bucks
Albert M Dorsky
Sui Yuen Eddie Hou
Original Assignee
Bertek Pharm Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bertek Pharm Inc filed Critical Bertek Pharm Inc
Priority to ES99956517.9T priority Critical patent/ES2470974T3/en
Priority to AU13114/00A priority patent/AU1311400A/en
Priority to EP99956517.9A priority patent/EP1119374B1/en
Publication of WO2000021485A2 publication Critical patent/WO2000021485A2/en
Publication of WO2000021485A3 publication Critical patent/WO2000021485A3/en
Publication of WO2000021485B1 publication Critical patent/WO2000021485B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups

Abstract

Polyurethane compositions for the protection of skin from material that is harmful to the skin or substances that are capable of penetrating the skin, are described.

Claims

AMENDED CLAIMS[received by the International Bureau on 29 June 2000 (29.06.00); original claims 7-14, 22 and 36 amended; original claims 1-6, 15-21 and 35 cancelled; remaining claims unchanged (6 pages)]
1. CANCELLED.
2. CANCELLED.
3. CANCELLED.
4. CANCELLED.
5. CANCELLED.
6. CANCELLED.
7. The method of Claim 22 wherein X is
Figure imgf000004_0001
8. The method of Claim 22, wherein Y is oxygen or -NR'-.
9. The method of Claim 22, wherein R is an alkylene radical containing about 2 to 6 carbon atoms.
10. The method of Claim 9 wherein R is -CH2CH2-, -CH2CH2CH2-, -CH2(CH3)- CH2- or -CH2CH2(CH3)-.
11. The method of Claim 22, wherein R is an alkenylene radical containing about 1 to 2 double bonds.
12. The method of Claim 22, wherein m is an integer from about 1 to 60.
13. The method of Claim 22, wherein n and n are correlated with m so as to provide a polyurethane compound having a molecular weight of about 220 to 200,000.
14. The method of Claim 13 , wherein n and n are correlated with m so as to provide a polyurethane compound having a molecular weight of about 1000 to 20,000.
15. CANCELLED.
16. CANCELLED.
17. CANCELLED.
18. CANCELLED.
19. CANCELLED.
35
20. CANCELLED.
21. CANCELLED.
22. A method for protecting the skin of a mammal, comprising applying to the skin of a mammal an effective amount of a polyurethane of Formula (I) in the absence of a pharmacologically active agent:
H-[-(YR)m-OC(O)NH-X-NHC(O)]n—
— (YR)m-OC(O)NH-X-NHC(O)O-(RY)m— — [C(O)NH-X-NHC(O)O-(RY)m-]n-H wherein: X is an alkylene or alkenylene radical containing from 1 to about 20 carbon atoms, or a cycloalkylene or cycloalkenylene radical containing from about 5 to 20 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, unsubstituted or substituted with one or more lower alkyl, lower alkoxy, lower alkoxy-substituted lower alkyl, nitro or amino groups or halogen atoms;
Y is oxygen, sulfur or -NR'-, where R' is hydrogen or lower alkyl; R is the same or different, and is chosen from alkylene, alkenylene, - SiR2R3-, and -CR2R3-NR4-CR2R3-, wherein R2, R3 and R4 are independently hydrogen or lower alkyl; m is an integer selected to provide a (YR) moiety having a molecular weight of from about 40 to about 10,000; and n and n are the same or a different integer from 0-30 inclusive, correlated with m so as to provide a polyurethane compound having a molecular weight of up to about 200,000; wherein said polyurethane forms a barrier on the surface of the skin and is absorbed into the outer layer of the skin.
23. The method of Claim 22 wherein said polyurethane is combined with a diluent.
36
24. The method of Claim 23 wherein said diluent is a solvent, emollient, humectant or emulsifier.
25. The method of Claim 22, wherein the polyurethane is applied as a cream, ointment, gel, lotion, foam, aerosol, spray, or liquid.
26. The method of Claim 25, wherein the composition is a liquid.
27. The method of Claim 26, wherein the composition further comprises an alcohol.
28. The method of Claim 22, wherein Y is oxygen, X is a cycloalkylene radical and R is alkylene.
29. The method of Claim 28, wherein X is 4,4'-dicyclohexylmethane and R is 1 ,2- propylene.
30. The method of Claim 29, wherein m is 12, and one of n and n' is 0 and the other one of n and n1 is from 1-3.
31. The method of Claim 29, wherein m is 51 , and one of n and n' is 0 and the other one of n and n' is from 1 -3.
32. The method of Claim 28, wherein X is 4,4'-dicyclohexylmethane and R is ethylene.
33. The method of Claim 32, wherein m is 8, and one of n and n' is 0 and the other one of n and n' is from 1-3.
34. The method of Claim 22 wherein the polyurethane is selected from the group consisting of poly [oxy (methyl- 1,2-ethanediy 1)], α-hydro-ω-hydroxy-, polymer with 1, l'-methylene-bis-[4-isocyanatocyclohexane] and having a molecular weight of 4000; poly[oxy(methyl-l,2-ethanediyl)], α-hydro-ω-hydroxy-, polymer with 1, l'-methylene-bis-[4-isocyanatocyclohexane] and having a molecular weight of 14,000; and poly(oxy-l,2-ethanediyl), αhydro-ω- hydroxy-, polymer with l,r-methylene-bis-[4-isocyanatocyclohexane].
35. CANCELLED.
37
36. Use of a polyurethane of the formula:
H-[-(YR)m-OC(O)NH-X-NHC(O)]n—
— (YR)m-OC(O)NH-X-NHC(O)O-(RY)m— — [C(O)NH-X-NHC(O)O-(RY)m-]n-H wherein:
X is an alkylene or alkenylene radical containing from 1 to about 20 carbon atoms, or a cycloalkylene or cycloalkenylene radical containing from about 5 to 20 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, unsubstituted or substituted with one or more lower alkyl, lower alkoxy, lower alkoxy-substituted lower alkyl, nitro or amino groups or halogen atoms;
Y is oxygen, sulfur or -NR'-, where R' is hydrogen or lower alkyl; R is the same or different, and is chosen from alkylene, alkenylene, - SiR2R3-, and -CR2R3-NR4-CR2R3-, wherein R2, R3 and R4 are independently hydrogen or lower alkyl; m is an integer selected to provide a (YR) moiety having a molecular weight of from about 40 to about 10,000; and n and n are the same or a different integer from 0-30 inclusive, correlated with m so as to provide a polyurethane compound having a molecular weight of up to about 200,000; for the preparation of a topical composition for protecting the skin of a mammal, wherein an effective amount of the topical composition, in the absence of a pharmacologically active agent, is applied to the skin of a mammal and forms a barrier on the surface of the skin and is absorbed into the outer layer of the skin.
37. The use of Claim 36 wherein said polyurethane is combined with a diluent.
38. The use of Claim 37 wherein said diluent is a solvent, emollient, humectant or emulsifϊer.
39. The use of Claim 36 wherein the composition is applied as a cream, ointment, gel, lotion, foam, aerosol, spray, or liquid.
40. The use of Claim 39 wherein the composition further comprises an alcohol.
41. The use of Claim 36 wherein Y is oxygen, X is a cycloalkylene radical and R is alkylene.
38
42. The use of Claim 41 wherein X is 4,4'-dicyclohexylmethane and R is 1,2- propylene.
43. The use of Claim 42 wherein m is 12, and one of n and n1 is 0 and the other one of n and n' is from 1-3.
44. The use of Claim 42 wherein m is 51 , and one of n and n' is 0 and the other one of n and n' is from 1-3.
45. The use of Claim 41 wherein X is 4,4'-dicyclohexylmethane and R is ethylene.
46. The use of Claim 45 wherein m is 8, and one of n and n' is 0 and the other one of n and n' is from 1-3.
47. The use of Claim 36 wherein the polyurethane is selected from the group consisting of poly[oxy(methyl-l,2-ethanediyl)], α-hydro-ω-hydroxy-, polymer with 1, r-methylene-bis-[4-isocyanatocyclohexane] and having a molecular weight of 4000; poly[oxy(methyl-l,2-ethanediyl)], α-hydro-ω-hydroxy-, polymer with 1, r-methylene-bis-[4-isocyanatocyclohexane] and having a molecular weight of 14,000; and poly(oxy-l,2-ethanediyl), αhydro-ω- hydroxy-, polymer with l,r-methylene-bis-[4-isocyanatocyclohexane].
39
PCT/US1999/023107 1998-10-09 1999-10-05 Polyurethanes as topical skin protectants WO2000021485A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
ES99956517.9T ES2470974T3 (en) 1998-10-09 1999-10-05 Polyurethanes as typical skin protectors
AU13114/00A AU1311400A (en) 1998-10-09 1999-10-05 Polyurethanes as topical skin protectants
EP99956517.9A EP1119374B1 (en) 1998-10-09 1999-10-05 Polyurethanes as topical skin protectants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/169,208 US6277364B1 (en) 1998-10-09 1998-10-09 Polyurethanes as topical skin protectants
US09/169,208 1998-10-09

Publications (3)

Publication Number Publication Date
WO2000021485A2 WO2000021485A2 (en) 2000-04-20
WO2000021485A3 WO2000021485A3 (en) 2000-07-20
WO2000021485B1 true WO2000021485B1 (en) 2000-11-09

Family

ID=22614638

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/023107 WO2000021485A2 (en) 1998-10-09 1999-10-05 Polyurethanes as topical skin protectants

Country Status (6)

Country Link
US (1) US6277364B1 (en)
EP (1) EP1119374B1 (en)
AU (1) AU1311400A (en)
ES (1) ES2470974T3 (en)
PT (1) PT1119374E (en)
WO (1) WO2000021485A2 (en)

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FR2811993B1 (en) * 2000-07-21 2006-08-04 Oreal NOVEL CATIONIC ASSOCIATIVE POLYMERS AND THEIR USE AS THICKENERS
FR2823118B1 (en) * 2001-04-04 2004-03-19 Lavipharm Lab Inc NOVEL FILM-FORMING COMPOSITION FOR TOPICAL USE AND ITS USE FOR THE DELIVERY OF ACTIVE AGENTS
AU2002352691A1 (en) * 2001-12-07 2003-06-23 Regenesis, Llc Cleaning article containing hydrophilic polymers
US7294342B2 (en) * 2002-07-11 2007-11-13 Summers Laboratories, Inc. Ectoparasite asphyxiator compositions and methods for their application
US8258191B2 (en) 2005-10-31 2012-09-04 Coloplast A/S Topical skin barriers and methods of evaluation thereof
US8211871B2 (en) * 2005-10-31 2012-07-03 Coloplast A/S Topical skin barriers and methods of evaluation thereof
CA2940494C (en) 2014-03-14 2022-11-08 Gojo Industries, Inc. Hand sanitizers with improved aesthetics and skin-conditioning to encourage compliance with hand hygiene guidelines
US10078207B2 (en) 2015-03-18 2018-09-18 Endochoice, Inc. Systems and methods for image magnification using relative movement between an image sensor and a lens assembly
US11452685B2 (en) * 2017-10-30 2022-09-27 L'oreal Cosmetic compositions providing for a transformative texture

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Also Published As

Publication number Publication date
WO2000021485A2 (en) 2000-04-20
EP1119374B1 (en) 2014-03-12
EP1119374A4 (en) 2007-08-01
PT1119374E (en) 2014-06-24
AU1311400A (en) 2000-05-01
US6277364B1 (en) 2001-08-21
ES2470974T3 (en) 2014-06-24
EP1119374A2 (en) 2001-08-01
WO2000021485A3 (en) 2000-07-20

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