PROCESS FOR PROTECTING AND REPAIRING KERATIN FIBRES, BASED ON OXIDIZED POLYSACCHARIDE AND ON (POLY)SACCHARIDE WITH AMINE GROUP

Abstract

The invention relates to i) a process for treating keratin fibres, in particular human keratin fibres such as the hair, employing a) at least one oxidized polysaccharide, in particular oxidized inulin, and b) at least one (polysaccharide with amine group(s); ii) a composition comprising the ingredients a) and b); iii) the use of a) and b) to treat keratin fibres, in particular human keratin fibres such as the hair, and iv) a multi-compartment kit or device comprising a) and b). The invention makes it possible to obtain good hair-conditioning cosmetic properties, with a long-lasting effect.

Claims

1.-22. (canceled)

23. A method for treating keratin fibers, comprising: (i) applying to the keratin fibers a first composition comprising at least one oxidized polysaccharide; and (ii) applying to the keratin fibers a second composition comprising at least one (poly)saccharide comprising at least one amine group.

24. The method according to claim 23, wherein (i) and (ii) are carried out simultaneously or sequentially.

25. The method according to claim 23, wherein the at least one oxidized polysaccharide comprises at least one aldehyde group and optionally, at least one anionic group.

26. The method according to claim 23, wherein the at least one oxidized polysaccharide is chosen from compounds according to formula (I) below:
P—(CHO)m(COOX)n   (I) wherein: P is a polysaccharide chain; X is chosen from a hydrogen atom, an ion derived from an alkali metal or an alkaline-earth metal, aqueous ammonia, organic amines, or basic amino acids; m+n is greater than or equal to 1; m is the degree of substitution of the polysaccharide with at least one aldehyde group (DS(CHO)), which is within the range from 0.001 to 2; and n is the degree of substitution of the polysaccharide with at least one carboxylic group (DS(COOX)), which is within the range from 0 to 2.

27. The method according to claim 26, wherein the polysaccharide chain is chosen from celluloses, starches, guar gums, inulins, xanthan gums, pullulan gums, agar-agar gums, carrageenan gums, gellan gums, gum arabics, tragacanth gums, xylans and derivatives thereof, cellobiose, maltodextrin, scleroglucan, chitosan, ulvan, fucoidan, alginate, pectin, heparin, or hyaluronic acid.

28. The method according to claim 26, wherein the polysaccharide chain is chosen from celluloses, hydroxyethylcelluloses, hydroxypropylcelluloses, starches, carboxymethylcelluloses, or inulins.

29. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from monosaccharides with at least one amine group.

30. The method according to claim 23, wherein the at least one (poly)saccharide is a monosaccharide with at least one amine group chosen from pentosamines, hexosamines, or heptosamines.

31. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from monosaccharides with at least one amine group, glucosamines according to formula (A), organic or inorganic acid salts or base salts thereof, or solvates thereof: ##STR00009## wherein: R.sup.a, R.sup.b, R.sup.d, R.sup.e, and R.sup.f, which are identical or different, are chosen from a hydroxyl or (C.sub.1-C.sub.4)alkoxy group, wherein the alkyl group is optionally substituted with at least one hydroxyl or carboxyl group, and an NR.sub.1R.sub.2 group, wherein R.sub.1 and R.sub.2, which are identical or different, are chosen from: i) a hydrogen atom, ii) a (C.sub.1-C.sub.6)alkyl group which is optionally substituted with at least one hydroxyl or NH.sub.2 group, iii) an aryl group, iv) an aryl(C.sub.1-C.sub.4)alkyl group, v) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl group, vi) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl(C.sub.1-C.sub.4)alkyl group, vii) —C(Y)—(Y′).sub.p—R′.sub.1, wherein Y and Y′, which are identical or different, are chosen from an oxygen or sulfur atom or N(R′.sub.2), and p=0 or 1, wherein R′.sub.1 and R′.sub.2 are chosen from compounds corresponding to i) to vi) defined above; further wherein at least one of the radicals R.sup.a, R.sup.b, R.sup.d, R.sup.e, and R.sup.f, is an NR.sub.1R.sub.2 group.

32. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from monosaccharides with at least one amine group, glucosamines according to formula (A′) below, organic or inorganic acid salts or base salts thereof, or solvates thereof: ##STR00010## wherein: R.sup.a, R.sup.b, R.sup.d, R.sup.e, and R.sup.f, which are identical or different, are chosen from a hydroxyl or (C.sub.1-C.sub.4)alkoxy group, the alkyl group of which is optionally substituted with at least one hydroxyl or carboxyl group, and an NR.sub.1R.sub.2 group, wherein R.sub.1 and R.sub.2, which are identical or different, are chosen from: i) a hydrogen atom, ii) a (C.sub.1-C.sub.6)alkyl group which is optionally substituted with at least one hydroxyl or NH.sub.2 group, iii) an aryl group, iv) an aryl(C.sub.1-C.sub.4)alkyl group, v) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl group, vi) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl(C.sub.1-C.sub.4)alkyl group, vii) —C(Y)—(Y′).sub.p—R′.sub.1, wherein Y and Y′, which are identical or different, are chosen from an oxygen or sulfur atom or N(R′.sub.2), and p=0 or 1, wherein R′.sub.1 and R′.sub.2 are chosen from compounds corresponding to i) to vi) defined above; further wherein at least one of the radicals R.sup.a, R.sup.b, R.sup.d, R.sup.e, and R.sup.f, is an NR.sub.1R.sub.2 group.

33. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from polysaccharides with at least one amine group or polyglucosamine.

34. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from polysaccharides with at least one amine group according to formula (B) below, organic or inorganic acid salts or base salts thereof, or solvates thereof: ##STR00011## wherein: n is an integer greater than or equal to 2; and R.sub.a, R.sub.b, and R.sub.c, which are identical or different, are chosen from a hydroxyl or (C.sub.1-C.sub.4)alkoxy group, the alkyl group of which is optionally substituted with at least one hydroxyl or carboxyl group, and an NR.sub.1R.sub.2 group, which are identical or different, are chosen from: i) a hydrogen atom, ii) a (C.sub.1-C.sub.6)alkyl group which is optionally substituted with at least one hydroxyl or NH.sub.2 group, iii) an aryl group, iv) an aryl(C.sub.1-C.sub.4)alkyl group, v) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl group, vi) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl(C.sub.1-C.sub.4)alkyl group, vii) —C(Y)—(Y′).sub.p—R′.sub.1, wherein Y and Y′, which are identical or different, are chosen from an oxygen or sulfur atom or N(R′.sub.2), and p=0 or 1, wherein R′.sub.1 and R′.sub.2 are chosen from compounds corresponding to i) to vi) defined above; further wherein at least one of the radicals R.sub.a, R.sub.b, and R.sub.c, is an NR.sub.1R.sub.2 group.

35. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from polysaccharides with at least one amine group according to formula (B′) below, organic or inorganic acid salts or base salts thereof, or solvates thereof: ##STR00012## wherein: R′ is chosen from a hydrogen atom or a (C.sub.1-C.sub.4)alkylcarbonyl group; R″ is chosen from a hydrogen atom or a (C.sub.1-C.sub.4)alkyl group optionally substituted with a carboxyl group; and n is an integer greater than or equal to 2.

36. The method according to claim 23, wherein the at least one (poly)saccharide is chosen from polysaccharides with at least one amine group according to formula (B″) below, organic or inorganic acid salts or base salts thereof, or solvates thereof: ##STR00013## wherein: n is an integer ranging from 5 to 500; and R.sub.a, R.sub.b, and R.sub.c, which are identical or different, are chosen from a hydroxyl or (C.sub.1-C.sub.4)alkoxy group, the alkyl group of which is optionally substituted with at least one hydroxyl or carboxyl group, and an NR.sub.1R.sub.2 group, which are identical or different, are chosen from: i) a hydrogen atom, ii) a (C.sub.1-C.sub.6)alkyl group which is optionally substituted with at least one hydroxyl or NH.sub.2 group, iii) an aryl group, iv) an aryl(C.sub.1-C.sub.4)alkyl group, v) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl group, vi) a (hetero)cyclo(C.sub.5-C.sub.7)alkyl(C.sub.1-C.sub.4)alkyl group, vii) —C(Y)—(Y′).sub.p—R′.sub.1, wherein Y and Y′, which are identical or different, are chosen from an oxygen or sulfur atom or N(R′.sub.2), and p=0 or 1, wherein R′.sub.1 and R′.sub.2 are chosen from compounds corresponding to i) to vi) defined above; further wherein at least one of the radicals R.sub.a, R.sub.b, and R.sub.c, is an NR.sub.1R.sub.2 group.

37. The method according to claim 23, wherein the at least one oxidized polysaccharide is present in the first composition in an amount ranging from about 0.05% to about 15% by weight, relative to the total weight of the first composition.

38. The method according to claim 23, wherein the at least one (poly)saccharide with at least one amine group is present in the second composition in an amount ranging from about 0.01% to about 10% by weight, relative to the total weight of the second composition.

39. The method according to claim 23, wherein the at least one (poly)saccharide with at least one amine group is chosen from a monosaccharide with at least one amine group, and wherein the pH of the composition ranges from about 2.5 to about 9.5.

40. The method according to claim 23, wherein (i) and (ii) are carried out simultaneously by applying to the keratin fibers a composition comprising the at least one oxidized polysaccharide and the at least one (poly)saccharide with at least one amine group.

41. The method according to claim 23, further comprising (iii) heating the keratin fibers to a temperature ranging from about 100° C. to about 250° C.

42. The method according to claim 23, wherein the steps are carried out in the following order: (i) applying the first composition comprising the at least one oxidized polysaccharide; (ii) applying the second composition comprising the at least one (poly)saccharide with at least one amine group; and optionally, (iii) heating the keratin fibers to a temperature ranging from about 100° C. to about 250° C.

Description

EXAMPLES

[0167] The following compositions were prepared; the % are percentages by weight in g per 100 g of composition.

TABLE-US-00001 Compositions Ingredients Composition 1 Control Milli-Q water only Composition 2 Comparative Oxidized inulin (OI)* at 5% in water, spontaneous pH of 3.0 Composition 3 Comparative Glucosamine at 5% in water, spontaneous pH of 4.4 Composition 4 Invention OI* at 5% + glucosamine at 5% in water, spontaneous pH of 3.0 Composition 5 Comparative Polyglucosamine - chitosan** at 1% in water, spontaneous pH of 4.3 Composition 6 Invention OI at 5% + polyglucosamine - chitosan** at 1% in water, spontaneous pH of 3.0 * Chitosan sold bySigma Aldrich under reference 523682. ** The oxidized inuiin (OI) polymer was prepared by oxidation of inulin sold under the name Inutec N25 by Orafti, by performing a reactive extrusion process as described in the article “Water soluble oxidized starches by peroxide reactive extrusion” by R.E. Wing and J.L. Willett, Industrial Crops and Products 7, 1997, pages 45-52. A BC21 co-rotating twin-screw extruder sold by the company Clextral was used, and aqueous hydrogen peroxide solution was used as oxidizing agent. 01: is obtained by reactive extrusion of a mixture of 78% by weight of inulin arid 1.57%> by weight of aqueous hydrogen peroxide solution; the spontaneous pH after reactive extrusion is 3.8. Compound 1 thus obtained has a carbonyl content of .sub.1.23.sub.%o (w/w, and a carboxyl content of 0.1.sub.7%> (w/w).

Evaluation Protocol

[0168] The tests for evaluating the treatment of the keratin fibres were carried out the following way:

[0169] Straight, 20 cm, 1.3 g locks of Caucasian hair were bleached (alkaline sensitivity AS 20%) and then underwent 10 cycles of exposure according to the following routine: [0170] 1) Placing the dry locks of hair in contact with a composition 1 to 5 in an amount of 2 g of composition per 1 g of hair, with 30 minutes of immersion at 40° C.; [0171] 2) Wringing out the locks then drying with a hair dryer at 60° C. with passage of a soft brush; [0172] 3) Applying a straightening iron at 190° C.: 5 passes of 9 seconds; [0173] 4) Wetting the locks with tap water, applying a shampoo containing 2% lauryl ether sulfate (% in g per 100 g composition), massaging for 15 seconds and careful rinsing with water at 37° C. for 10 seconds; [0174] 5) Drying with a hood at 60° C. for 10 minutes.

[0175] Persistence on shampooing: repetition of the sequence of steps 4 and 5 described above 9 times.

Evaluations

[0176] Feel: After applying and drying, the dry locks were evaluated sensorially on tactile criteria by 5 members of laboratory personnel who had been trained in the sensory evaluation of hair. Only the ends of the locks (bottom 3 cm) were evaluated. A score from 1 (locks very coarse to the touch) to 5 (locks very soft to the touch) was given. The averages of these scores are reported.

[0177] Disentangling: Tests of disentangling using a comb were carried out after immersion for 10 seconds in water, by 5 passes of a small-toothed plastic comb (7 teeth/cm, diameter of the teeth approx. 800 ∝η1). A score from 1 (locks very difficult to disentangle) to 5 (locks very easy to disentangle) was given, The averages of these scores are reported.

Results:

[0178] Protocol 1: application of ingredient a) oxidized polysaccharide (oxidized inulin)+b) monosaccharide with amine group (glucosamine) applied together to keratin fibres, followed by a heat treatment using a straightening iron

TABLE-US-00002 Average score for softness of dry locks after 1 after 10 Cornpositions shampoo wash shampoo washes Composition 1 3.1 3.1 Composition 2 3.4 3.3 Composition 3 3.6 3.4 Composition 4 4.2 3.8

[0179] The locks treated with composition 4 according to the invention are perceived to be softer than the locks treated with the other, comparative, compositions, after 1 or even 10 shampoo washes.

[0180] Protocol 2: application of ingredient a) oxidized polysaccharide (oxidized inulin)+b) polysaccharide with amine groups (chitosan) applied together to keratin fibres, followed by a heat treatment usinq a straightening iron

TABLE-US-00003 Average score for softness of ends of dry locks after 1 after 10 Composition shampoo wash shampoo washes Composition 1 2.3 2.2 Composition 2 2.4 2.4 Composition 5 3.0 2.6 Composition 6 3.4 3.1 Protocol 2 Average score for ease of wet disentangling after 1 after 10 Composition shampoo wash shampoo washes Composition 1 2.2 2.3 Composition 2 1.9 2.1 Composition 5 3.7 3.0 Composition 6 4.1 3.3

[0181] The locks treated with composition 6 according to the invention are perceived to be softer at their dry ends and easier to disentangle using a comb when wet than the locks treated with the other compositions, after 1 or even 10 shampoo washes.

[0182] These results show that combining ingredients a) and b), especially a) oxidized inulin and b) glucosamine, leads to better sensory results than the ingredients a) or b) used individually, with improved dry softness, and that this effect persists up to 10 shampoo washes.

[0183] It was also observed that combining ingredients a) and b), especially a) oxidized inulin and b) polyglucosamine, improves the ease of wet disentangling perceived and the softness of dry ends, compared to those ingredients used individually. It was observed that this effect persists even after 10 shampoo washes.