| Title: |
Composition comprising novel polyurethanes and cosmetic treatment process |
| Document Number: |
20070283977 |
| Publication Date: |
December 13, 2007 |
| Appl. No: |
11/723455 |
| Application Filed: |
March 20, 2007 |
| Abstract: |
The present disclosure relates to novel polyurethanes comprising cationic units, of diisocyanates and of nonionic units derived from polyolefins comprising at least 10 mol % of units comprising at least one residual carbon-carbon double bond. The present disclosure also relates to cosmetic or pharmaceutical compositions comprising the polyurethanes, and also to a cosmetic treatment process, for example for shaping and/or holding the hair, comprising the application of such a composition. |
| Inventors: |
Mougin, Nathalie (Paris, FR); Schultze, Xavier (Pontault-Combault, FR) |
| Claim: |
1. A polyurethane comprising: (a1) at least one cationic or cationizable unit derived from at least one tertiary or quaternary amine comprising at least two reactive functions containing labile hydrogen, (a2) at least one nonionic unit derived from at least one polyolefin comprising at least two reactive functions containing labile hydrogen, said polyolefin comprising at least 10 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin; (b) at least one unit derived from a compound comprising at least two isocyanate functions. |
| Claim: |
2. A polyurethane according to claim 1, wherein the amines forming the units (al) are chosen from compounds of formulae: [chemical expression included] wherein: each Ra, independently of each other, is a linear or branched divalent C1-C6 alkylene group, or alternatively a C3-C6 cycloalkylene or arylene group, or mixtures thereof; these groups optionally being substituted with at least one halogen atom and/or optionally comprising at least one heteroatom chosen from O, N, P and S, each Rb is, independently of each other, a linear or branched C1-C6 alkyl group, or alternatively a C3-C6 cycloalkyl or aryl group, or mixtures thereof; these groups optionally being substituted with at least one halogen atom and/or optionally comprising at least one heteroatom chosen from O, N, P and S, each R′b is chosen from H and a linear or branched C1-C6 alkyl group, or alternatively a C3-C6 cycloalkyl or aryl group, or mixtures thereof; these groups optionally being substituted with at least one halogen atom and/or optionally comprising at least one heteroatom chosen from O, N, P and S, m and p are, independently of each other, equal to 0 or 1; each X is, independently, an oxygen or sulfur atom, or a group NH or NRc, wherein Rc is a C1-C6 alkyl group, and A− is a physiologically acceptable counterion. |
| Claim: |
3. A polyurethane according to claim 2, wherein said counterion A− is a halide. |
| Claim: |
4. A polyurethane according to claim 1, wherein the amines are: of formula: [chemical expression included] in which formulas above or in the amine formulas in claim 1 Ra is a linear or branched divalent C1-C6 alkylene group; and/or Rb is a linear or branched C1-C6 alkyl group; and/or X═O. |
| Claim: |
5. A polyurethane according to claim 4, wherein the amines are of formula: [chemical expression included] wherein Ra is a linear or branched divalent C1-C6 alkylene group; and Rb is a linear or branched C1-C6 alkyl group. |
| Claim: |
6. A polyurethane according to claim 1, wherein the amines are chosen from N-methyldiethanolamine and N-tert-butyldiethanolamine. |
| Claim: |
7. A polyurethane according to claim 1, wherein the polyolefin comprising at least two reactive functions containing labile hydrogen, forming the nonionic units (a2), is an olefin homopolymer. |
| Claim: |
8. A polyurethane according to claim 7, wherein the homopolymer is chosen from 1,2-butadiene, 1,4-butadiene and isoprene homopolymers in their cis and trans forms; 1,2-polybutadienes, poly(cis-1,4-isoprenes) and poly(trans-1,4-isoprenes). |
| Claim: |
9. A polyurethane according to claim 1, wherein the polyolefin comprising at least two reactive functions containing labile hydrogen, forming the nonionic units (a2), is an olefin copolymer consisting of units comprising at least one C═C double bond. |
| Claim: |
10. A polyurethane according to claim 9, wherein the polyolefin is chosen from copolymers comprising 1,2-butadiene units and/or 1,4-butadiene units in its cis and/or trans forms, and/or isoprene units as a mixture. |
| Claim: |
11. A polyurethane according to claim 9, wherein the polyolefin is a 1,2-buta-diene/1,4-butadiene statistical copolymer. |
| Claim: |
12. A polyurethane according claim 9, wherein the polyolefin is statistical and corresponds to the following structure: [chemical expression included] wherein: m, n and p are mole fractions ranging from 0 to 1, and m+n+p=1; n is an integer ranging from 10 to 100; x is 0 or 1, and X is a divalent carbon-based radical comprising 1 to 10 carbon atoms. |
| Claim: |
13. A polyurethane according to claim 12, wherein m ranges from 0.15 to 0.7, p ranges from 0.15 to 0.7, q ranges from 0.1 to 0.4, and n is an integer ranging from 15 to 50. |
| Claim: |
14. A polyurethane according to claim 12, wherein the polyolefin is chosen from: polybutadienes with hydroxyl end groups; polybutadienes with primary hydroxyl end groups; polybutadienes with secondary hydroxyl end groups. |
| Claim: |
15. A polyurethane according to claim 14, wherein the polyolefin is chosen from: polybutadienes with hydroxyl end groups corresponding to the following structure: [chemical expression included] wherein m=0.6, p=q=0.2 and n=25; polybutadienes with primary hydroxyl end groups, of structure: [chemical expression included] with m=0.17, p=0.65 and q=0.18, and n is such that the number-average molecular weight Mn ranges from 1000 to 10,000; polybutadienes with secondary hydroxyl end groups corresponding to the following structure: [chemical expression included] with m=0.17, p=0.65 and q=0.18 and n is such that the number-average molecular weight Mn ranges from 1000 to 12 000. |
| Claim: |
16. A polyurethane according to claim 1, wherein the polyolefin comprising at least two reactive functions containing labile hydrogen, forming the nonionic units (a2), is a copolymer also comprising additional units not comprising a C═C double bond, present in a maximum amount of 90 mol %. |
| Claim: |
17. A polyurethane according to claim 16, wherein the additional units are chosen from ethylene —(CH2—CH2)n—, propylene —(CH2—CH2—CH2)n— or isopropylene —(CH2CH (CH3))n-units, and/or butylene units of formula: [chemical expression included] and also mixtures thereof. |
| Claim: |
18. A polyurethane according to claim 1, wherein the at least one polyolefin that may be used to form the units (a2) comprises at least 20 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin. |
| Claim: |
19. A polyurethane according to claim 18, wherein the at least one polyolefin that may be used to form the units (a2) comprises 100 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin. |
| Claim: |
20. A polyurethane according to claim 1, wherein the at least one polyolefin is chosen from: homopolymers; copolymers of structure: [chemical expression included] wherein m, n and p are mole fractions ranging from 0 to 1, and m+n+p=1; p ranges from 0.1 to 0.8; and q ranges from 0.05 to 0.5; n is an integer ranging from 10 to 100; x is 0 or 1, and X is a divalent carbon-based radical comprising 1 to 10 carbon atoms. |
| Claim: |
21. A polyurethane according to claim 20, wherein the homopolymers are chosen from 1,4-polybutadiene and 1,2-polybutadiene |
| Claim: |
22. A polyurethane according to claim 20 wherein in said copolymers, m ranges from 0.15 to 0.7, p ranges from 0.15 to 0.7, q ranges from 0.1 to 0.4, and n is an integer ranging from 15 to 50. |
| Claim: |
23. A polyurethane according to claim 1, wherein the at least one polyolefin forming the nonionic units (a2) has a number-average molecular mass (Mn) ranging from 400 to 50 000. |
| Claim: |
24. A polyurethane according to claim 23, wherein the at least one polyolefin forming the nonionic units (a2) has a number-average molecular mass (Mn) ranging from 1500 to 12 000. |
| Claim: |
25. A polyurethane according to claim 1, wherein the compound comprising at least two isocyanate functions is chosen from diisocyanates, or mixtures of a diisocyanate and of a polyisocyanate comprising more than two isocyanate functions, wherein said polyisocyanate represents 0.1% to 40% of the weight of the mixture. |
| Claim: |
26. A polyurethane according to claim 25, wherein said polyisocyanate represents 0.1% to 30% of the weight of the mixture. |
| Claim: |
27. A polyurethane according to claim 1, wherein the compound comprising at least two isocyanate functions is chosen from conjugated or non-conjugated, aromatic or non-aromatic cyclic aliphatic diisocyanates. |
| Claim: |
28. A polyurethane according to claim 1, in which the compound comprising at least two isocyanate functions is chosen from methylenediphenyl diisocyanate, methylenecyclohexane diisocyanate, isophorone diisocyanate, toluene diisocyanate, naphthalene diisocyanate, 1,4-butane diisocyanate and 1,6-hexane diisocyanate, and mixtures thereof. |
| Claim: |
29. A polyurethane according to claim 1, comprising: at least one cationic unit resulting from amines of formula: [chemical expression included] wherein: Ra is a linear or branched divalent C1-C6 alkylene group; Rb is a linear or branched C1-C6 alkyl group; and X is O; at least one nonionic unit resulting from polyolefins chosen from 1,4-polybutadiene and 1,2-polybutadiene homopolymers; or copolymers of structure: [chemical expression included] wherein m, n and p are mole fractions ranging from 0 to 1, and m+n+p=1; p ranges from 0.1 to 0.8; q ranges from 0.05 to 0.5; n is an integer ranging from 10 to 100; x=0 or 1, and X is equal to a divalent carbon-based radical, comprising 1 to 10 carbon atoms; and at least one unit resulting from aliphatic diisocyanates. |
| Claim: |
30. A polyurethane according to claim 29, wherein m ranges from 0.15 to 0.7, p ranges from 0.15 to 0.7, q ranges from 0.1 to 0.4, and n is an integer ranging from 15 to 50. |
| Claim: |
31. A polyurethane according to claim 1, comprising: at least one cationic unit resulting from amines of formula: [chemical expression included] wherein Ra is a linear or branched divalent C1-C6 alkylene group; and Rb is a linear or branched C1-C6 alkyl group; at least one nonionic unit resulting from polyolefins of structure: [chemical expression included] wherein m, n and p are mole fractions ranging from 0 to 1, and m+n+p=1; p ranges from 0.1 to 0.8; and q ranges from 0.05 to 0.5; n is an integer ranging from 10 to 100; x=0 or 1, and X is a divalent carbon-based radical, comprising 1 to 10 carbon atoms; and at least one unit resulting from diisocyanates chosen from methylenecyclohexane diisocyanate, isophorone diisocyanate, 1,4-butane diisocyanate and 1,6-hexane diisocyanate, and mixtures thereof. |
| Claim: |
32. A polyurethane according to claim 31, wherein m ranges from 0.15 to 0.7, p ranges from 0.15 to 0.7, q ranges from 0.1 to 0.4, and n is an integer ranging from 15 to 50. |
| Claim: |
33. A polyurethane according to claim 1 wherein: the amines forming the cationic or cationizable units (a1) represent from 0.1% to 50% by weight, relative to the total weight of the final polyurethane; and/or the polyolefins forming the nonionic units (a2) represent from 30% to 99% by weight, relative to the total weight of the final polyurethane; and/or the compounds comprising at least two isocyanate functions forming the units (b) represent from 1% to 60% by weight, relative to the total weight of the final polyurethane. |
| Claim: |
34. A polyurethane according to claim 33, wherein the amines forming the cationic or cationizable units (a1) represent from 5% to 20% by weight relative to the total weight of the final polyurethane. |
| Claim: |
35. A polyurethane according to claim 33, wherein the polyolefins forming the nonionic units (a2) represent from 60% to 80% by weight relative to the total weight of the final polyurethane. |
| Claim: |
36. A polyurethane according to claim 33, wherein the polyolefins forming the compounds comprising at least two isocyanate functions forming the units (b) represent from 15% to 35% by weight relative to total weight of the final polyurethane. |
| Claim: |
37. A cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one polyurethane comprising: (a1) at least one cationic or cationizable unit derived from at least one tertiary or quaternary amine comprising at least two reactive functions containing labile hydrogen, (a2) at least one nonionic unit derived from at least one polyolefin comprising at least two reactive functions containing labile hydrogen, said polyolefin comprising at least 10 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin; (b) at least one unit derived from a compound comprising at least two isocyanate functions. |
| Claim: |
38. A composition according to claim 37, wherein the polyurethane is present in an amount ranging from 0.1% to 90% by weight relative to the weight of the composition. |
| Claim: |
39. A composition according to claim 38, wherein the polyurethane is present in an amount ranging from 6% to 10% by weight relative to the weight of the composition. |
| Claim: |
40. A composition according to claim 37, wherein the physiologically acceptable medium comprises at least one compound chosen from water, alcohols, polyols, polyol or glycol ethers, hydrophilic C2-C4 aldehydes, esters, carbon-based oils, silicone oils, fluorosilicone oils; gelling agents and/or thickeners such as anionic, nonionic or cationic associative or non-associative polymers; anionic, nonionic, cationic and/or amphoteric surfactants; pro-penetrating agents, emulsifiers, fragrances, preserving agents, fillers, sunscreens; silicones; dyestuffs, proteins, vitamins, provitamins; fixing or non-fixing, anionic, nonionic, cationic or amphoteric polymers; moisturizers, emollients, softeners; mineral, plant or synthetic oils; hydrophilic or lipophilic active agents; antifoams, antiperspirants, free-radical scavengers, bactericidal agents and anti-dandruff agents; and also mixtures thereof. |
| Claim: |
41. A composition according to claim 37, which is in a form chosen from a product for caring for, cleansing and/or making up bodily or facial skin, the lips, the eyelashes, the nails and the hair; an antisun or self-tanning product; a body hygiene product; and a hair product. |
| Claim: |
42. A composition according to claim 37, which is in the form of a hair composition for holding the hairstyle or for shaping the hair. |
| Claim: |
43. A composition according to claim 37, which is in the form of a hair composition of hair lacquer type, and in which the polyurethane is present in an amount ranging from 0.1% to 25% by weight, relative to the weight of the composition. |
| Claim: |
44. A composition according to claim 43, wherein the polyurethane is present in an amount ranging from 4% to 8% by weight relative to the weight of the composition. |
| Claim: |
45. A composition according to claim 37, which is in the form of a styling composition in which the polyurethane is present in an amount ranging from 0.5% to 20% by weight, relative to the weight of the composition. |
| Claim: |
46. A composition according to claim 45, wherein the polyurethane is present in an amount ranging from 5% to 8% relative to the weight of the composition. |
| Claim: |
47. A composition according to claim 37, which is in the form of a hair composition of shampoo type in which the polyurethane is present in an amount ranging from 0.1% to 20% by weight, relative to the weight of the composition. |
| Claim: |
48. A composition according to claim 47, wherein the polyurethane is present in an amount ranging from 2% to 5% relative to the weight of the composition. |
| Claim: |
49. A cosmetic treatment process for making up, caring for, cleansing, coloring or shaping keratin materials comprising applying to said keratin materials: (a1) at least one cationic or cationizable unit derived from at least one tertiary or quaternary amine comprising at least two reactive functions containing labile hydrogen, (a2) at least one nonionic unit derived from at least one polyolefin comprising at least two reactive functions containing labile hydrogen, said polyolefin comprising at least 10 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin; (b) at least one unit derived from a compound comprising at least two isocyanate functions. |
| Claim: |
50. A cosmetic treatment process for shaping and/or holding the hair, comprising applying to hair: (a1) at least one cationic or cationizable unit derived from at least one tertiary or quaternary amine comprising at least two reactive functions containing labile hydrogen, (a2) at least one nonionic unit derived from at least one polyolefin comprising at least two reactive functions containing labile hydrogen, said polyolefin comprising at least 10 mol % of units comprising at least one C═C double bond, relative to the total amount of units forming said polyolefin; (b) at least one unit derived from a compound comprising at least two isocyanate functions; optionally followed by a rinsing step. |
| Current U.S. Class: |
132203/000 |
| Current International Class: |
61; 45; 61; 61; 61; 08; 61; 61; 61; 61 |
| Accession Number: |
edspap.20070283977 |
| Database: |
USPTO Patent Applications |
