Polyester polyurethanes, process for preparing them, pseudolatices produced from the said polyester polyurethanes and their use in cosmetic compositions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61K-007/00
A61K-007/02
C08J-003/03
C08L-075/06
출원번호
US-0511073
(2000-02-23)
우선권정보
FR-1993-309608 (1993-08-04)
발명자
/ 주소
Mondet, Jean
Lion, Bertrand
Mougin, Nathalie
Piot, Bertrand
de La Poterie, Valé
rie
출원인 / 주소
L'Oreal
대리인 / 주소
Oliff & Berridge, PLC
인용정보
피인용 횟수 :
21인용 특허 :
13
초록▼
The present invention relates to polyurethanes and a process for preparing them. These polyester polyurethanes contain units corresponding to the following formulae (I) and (II):The polyester polyurethanes according to the present invention form pseudolatices and may be utilized as film-forming resi
The present invention relates to polyurethanes and a process for preparing them. These polyester polyurethanes contain units corresponding to the following formulae (I) and (II):The polyester polyurethanes according to the present invention form pseudolatices and may be utilized as film-forming resin in cosmetic compositions.
대표청구항▼
1. A stable pseudolatex comprising in suspension in an aqueous phase particles of non-crosslinked neutralized polyester polyurethane, wherein the polyester polyurethane contains units corresponding to the following formulae (I) and (II):in which:R represents an alkylene or cycloalkylene radical or a
1. A stable pseudolatex comprising in suspension in an aqueous phase particles of non-crosslinked neutralized polyester polyurethane, wherein the polyester polyurethane contains units corresponding to the following formulae (I) and (II):in which:R represents an alkylene or cycloalkylene radical or a bivalent aromatic radical having from 6 to 15 carbon atoms,n represents an integer such that the molecular weight of the recurring unit is between 400 and 5,000,R 1 represents a bivalent radical selected from the group consisting of:(i) —(CH 2 ) m —, m being an integer between 2 and 12, and(ii) the movable bond being in the ortho, meta or para position,R 2 represents a bivalent radical selected from the group consisting of:R 3 representing a hydrogen atom or a branched alkyl radical having from 1 to 3 carbon atoms,R 4 representing a hydrogen atom or a linear or branched alkyl radical having from 1 to 4 carbon atoms,R 5 representing a linear or branched alkyl radical having from 1 to 4 carbon atoms, andp being 0 or 1;in whichR is us defined above for the units of formula (I),A represents an alkylene radical having from 2 to 20 carbon atoms, substituted with a sulphonic acid function, or interrupted by a tertiary nitrogen atom;wherein the mole ratio between the units (II) and units (I) being between 1:1 and 10:1,wherein the sulphonic acid function is neutralized with a neutralizing agent selected from the group consisting of an inorganic base and an organic base, and the tertiary nitrogen atom is neutralized with a neutralizing agent selected from the group consisting of an inorganic acid and an organic acid, the degree of neutralization being between 20 and 100%, andwherein the average diameter or the particles is between 5 and 300 nm. 2. A stable pseudolatex comprising in suspension in an aqueous phase particles of non-crosslinked neutralized polyester polyurethane, wherein the polyester polyurethane consists of units consisting of formulae (I) and (II), and optionally of units of formula (III):in which:in which:R is as defined in claim 1 for the units of formula (I),B and B′, which are identical or different, represent —O— or —NH—, it not being possible for B and B′ simultaneously to represent —O—, andX represents an alkylene or cycloalkylene radical having from 2 to 12 carbon atoms or a bivalent aromatic radical having from 6 to 12 carbon atoms. 3. Stable pseudolatex according to claim 2, wherein the molecular weight of said polyester polyurethane, measured by steric exclusion chromatography, is comprised between 4,000 and 500,000. 4. Stable pseudolatex according to claim 2, wherein the molecular weight of said polyester polyurethane, measured by steric exclusion chromatography, is comprised between 6,000 and 200,000. 5. Stable pseudolatex according to claim 2, wherein the average size of the particles is between 10 and 250 nm. 6. Stable pseudolatex according to claim 2, wherein the size polydispersity of the particles, measured by quasi-elastic light scattering, is less than 0.5. 7. Stable pseudolatex according to claim 2, wherein the size polydispersity of the particles, measured by quasi-elastic light scattering, is between 0.05 and 0.4. 8. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the mole ratio between the units (II) and the unite (I) is between 1:1 and 5:1. 9. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the radical R is selected from the group consisting of hexamethylene, 4,4′-biphenylenemethane, 2,4-tolylene, 2,6-tofylene, 1,5-naphtylene, p-phenylene and 4,4′-methylene-bis (cyclohexyl) radicals and a bivalent radical derived from isophorone. 10. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the radical R is selected from the group consisting of 4,4′-biphenylenemethane and 4,4-methylone-bis (cyclohexyl) radical s. 11. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane R 2 represents a bivalent radical formula:and R 1 represents —(CH 2 ) 8 — or a p-phenylene radical. 12. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane the bivalent radical A of thy unit of formula (II) is chosen from the group consisting of:R 6 representing a linear or branched alkyl radical having from 1 to 3 carbon atoms,Y representing a carboxylic acid group, or a salt thereof andw and z, which are identical or different, representing an integer between 1 and 5. 13. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the radical A of the unit of formula (II) is 14. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane:the radical R is selected from the group consisting of 4,4′-biphenylenemethane and 4,4′-methylene-bis (cyclohexyl) radicals,R 2 represents a bivalent radical of formula: R 1 represents —(CH 2 ) 8 — and/or a p-phenylene radical. 15. Stable pseudolatex according to claim 14, wherein in said polyester polyurethane, the radical A of the unit of formula (II) is 16. Stable pseudolatex according to claim 15, wherein said polyester polyurethane does not contain units of formula (III). 17. Cosmetic composition comprising the pseudolatex according to claim 16 in a cosmetic carrier. 18. Cosmetic composition according to claim 17, wherein the pseudolatex is present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 19. Cosmetic composition according to claim 17, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic composition. 20. Stable pseudolatex according to claim 2, wherein said polyester polyurethane does not contain units of formula (III). 21. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the mob ratio of the sum of the units of formulae (II) and (III) to the units of formula (I) is an integer between 1 and 10. 22. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the mole ratio of the sum of the units of formulae (II) and (III) to the units of formula (I) in an integer between 1 and 5. 23. Stable pseudolatex according to claim 2, wherein in said polyester polyurethane, the bivalent radical —B—X—B′— of the units of formula (III) is selected from the group consisting —NH—CH 2 —CH 2 —CH 2 —NH—, —O—CH 2 —CH 2 —NH— and —NH —CH 2 —CH 2 —O—. 24. Stable pseudolatex according to claim 2, wherein said polyester polyurethane is made of units of formula (I), (II) and (III), and wherein:the radical R is selected from the group consisting of 4,4′-biphenylenemethane and 4-4′ -methylene bis (cyclohexyl) radicals,R 2 represents a bivalent radical of formula: R 1 represents —(CH 2 ) 8 — and/or a p-phenylene,the radical A is the bivalent radical —B—X—B′— of the units of formula (III) is selected from the group consisting of —NH—CH 2 —CH 2 —CH 2 —NH—, —O—CH 2 —CH 2 —NH— and —NH—CH 2 —CH 2 —O—. 25. Cosmetic composition comprising the pseudolatex according to claim 24 in a cosmetic carrier. 26. Cosmetic composition according to claim 25, wherein the pseudolatex is a present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 27. Cosmetic composition according to claim 25, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic composition. 28. Stable pseudolatex according to claim 2, wherein the inorganic base or organic base is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonia solution, 2-amino-2-methyl-1-propanol (AMP), triethanolamine, triisopropanolamine (TIPA), monoethanolamine, diethanolamine, tris(2-hydroxy-1-propyl)amine, 2-amino-2-methyl-1,3-propanediol (AMPD) and 2-amino-2-hydroxymethyl-1,3-propanediol, and lysine. 29. Cosmetic composition comprising the pseudolatex according to claim 2, in a cosmetic carrier. 30. Cosmetic composition according to claim 29, wherein the pseudolatex is present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 31. Cosmetic composition according to claim 29, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic position. 32. Stable pseudolatex according to claim 1, wherein the molecular weight of said polyester polyurethane, measured by steric exclusion chromatography, is comprised between 4,000 and 500,000. 33. Stable pseudolatex according to claim 1, wherein the molecular weight of said polyester polyurethane, measured by steric exclusion chromatography, is comprised between 6,000 and 200,000. 34. Stable pseudolatex according to claim 1, wherein the average size of the particles is between 10 and 250 nm. 35. Stable pseudolatex according to claim 1, wherein the size polydispersity of the particles, measured by quasi-elastic light scattering, is less than 0.5. 36. Stable pseudolatex according to claim 1, wherein the size polydispersity of the particles, measured by quasi-elastic light scattering, is between 0.05 and 0.4. 37. Stable pseudolatex according to claim 1, wherein in said polyester polyurethane, the mole ratio between the units (II) and the units ( 1 ) is between 1:1 and 5:1. 38. Stable pseudo latex according to claim 1, wherein in said polyester polyurethane, the radical R is selected from the group consisting of hexamethylene, 4,4′-biphenylenemethane, 2,4-tolylene, 2,6-tolylene, 1,5-naphtylene, p-phenylene and 4,4′-methylene-bis (cyclohexyl) radicals and a bivalent radical derived from isophorone. 39. Stable pseudolatex according to claim 1, wherein in said polyester polyurethane, the radical R is selected from the group consisting of 4,4′-biphenylenemethane and 4,4-methylene-bis (cyclohexyl) radicals. 40. Stable pseudolatex according to claim 1, wherein in said polyester polyurethane, R 2 represents a bivalent radical formula:and R 1 represents —(CH 2 ) 8 —or a p-phenylene radical. 41. Stable pseudo latex according to claim 1, wherein in said polyester polyurethane the bivalent radical A of the unit of formula (II) is chosen from the group consisting of:R 6 representing a linear or branched alkyl radical having from 1 to 3 carbon atoms,Y representing a sulphonic acid group or a salt thereof, andw and z, which are identical or different, representing an integer between 1 and 5R 7 representing a linear or branched alkyl radical having from 1 to 4 carbon atoms, andr and s, which are identical or different representing an inter between 1 and 10. 42. Stable pseudolatex according to claim 1, wherein in said polyester polyurethane, the bivalent radical A of the unit of formula (II) is 43. Stable pseudolatex according to claim 1, wherein in said polyester polyurethane:the radical R is selected from the group consisting of 4,4′-biphenylenemethane and 4,4′-methylene-bis (cyclohexyl) radicals,R 2 represents a bivalent radical of formulaR 1 represents —(CH 2 ) 8 — and/or a p-phenylene. 44. Stable pseudolatex according to claim 43, wherein in said polyester polyurethane, the radical A of the unit of formula (II) is 45. Cosmetic composition comprising the pseudolatex according to claim 44 in a cosmetic carrier. 46. Cosmetic composition according to claim 45, wherein the pseudolatex is present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 47. Cosmetic composition according to claim 45, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic composition. 48. Stable pseudolatex according to claim 1, wherein said polyester polyurethane further contains units corresponding to the following formula (III):in which:R is as defined in claim 1, for the units of formula (I),B and B′, which are identical or different, represent —O— or —NH—, it not being possible far B and B′ simultaneously to represent —O—, andX represents an alkylene or cycloalkylene radical having from 2 to 12 carbon atoms or a bivalent aromatic radical having from 6 to 12 carbon atoms. 49. Stable pseudolatex according to claim 48, wherein in said polyester polyurethane, the mole ratio of the sum of the units of formulae (II) and (III) to the units of formula (I) is an integer between 1 and 10. 50. Stable pseudolatex according to claim 48, wherein in said polyester polyurethane, the mole ratio of the sum of the units of formulae (II) and (III) to the units of formula (I) is an integer between 1 and 5. 51. Stable pseudolatex according to claim 48, wherein in said polyester polyurethane, the bivalent radical —B—X—B′— of the units of formula (III) is selected from the group consisting of —NH—CH 2 —CH 2 —NH—, —O—CH 2 —CH 2 —NH— and —NH —CH 2 —CH 2 —O—. 52. Stable pseudolatex according to claim 51, wherein in said polyester polyurethane,the radical R is selected from the group consisting of 4, 4′-biphenylenemethane and 4,4′-methylene bis (cyclohexyl) radicals,R 2 represents a bivalent radical of formula:R 1 represents —(CH 2 ) 8 — and/or p-phenylene, andA represents 53. Cosmetic composition comprising the pseudolatex according to claim 48 in a cosmetic carrier. 54. Cosmetic composition according to claim 53, wherein the pseudolatex is a present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 55. Cosmetic composition according to claim 53, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic composition. 56. Stable pseudolatex according to claim 1, wherein the inorganic base or organic base is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonia solution, 2-amino-2-methyl-1-propanol (AMP), triethanolamine, triisopropanolamine (TIPA), monoethlanolamine, diethanolamine, tris(2-hydroxy-1-propyl)amine, 2-amino 2-methyl-1,3-propanediol (AMPD), 2-amino-2-hydroxymethyl-1,3-propanediol and lysine. 57. Stable pseudolatex according to claim 1, wherein the inorganic acid or organic acid is selected from the group consisting of hydrochloric acid, lactic acid, glycolic acid and mandelic acid. 58. Cosmetic composition comprising the pseudolatex according to claim 1 in a cosmetic carrier. 59. Cosmetic composition according to claim 58, wherein the pseudolatex is present in a proportion of between 0.5 and 30% by weight relative to the total weight of the cosmetic composition. 60. Cosmetic composition according to claim 58, wherein the pseudolatex is present in a proportion of between 1 and 25% by weight relative to the total weight of the cosmetic composition.
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