COMPOSITION COMPRISING A DICARBONYL DERIVATIVE AND METHOD FOR STRAIGHTENING THE HAIR USING THIS COMPOSITION

Abstract

The present invention relates to a cosmetic composition comprising: one or more dicarbonyl derivatives corresponding to formula (I) below, and/or derivatives thereof and/or hydrates thereof and/or salts thereof:

##STR00001##

in which formula (I) R═H, COOH, linear or branched C.sub.1-C.sub.6 alkyl which is optionally substituted with an OH or COOH or Br radical; phenyl or benzyl optionally substituted with an OH or COOH radical; or alternatively an indolyl radical or

##STR00002## one or more silanes corresponding to formula (II) below and/or oligomers thereof:

R.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x(OH).sub.y  (II)

in which formula (II): R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.6 hydrocarbon-based chain substituted with a group chosen from the following groups: amine NH.sub.2 or NHR (R═C.sub.1-C.sub.20 and especially C.sub.1-C.sub.6 alkyl optionally substituted with a radical comprising a silicon atom, C.sub.3-C.sub.40 cycloalkyl or C.sub.6-C.sub.30 aromatic), or with a hydroxyl group, a thiol group, an aryl or aryloxy group which is unsubstituted or substituted, in particular with an amino group or with a C.sub.1-C.sub.4 aminoalkyl group; R.sub.1 possibly being interrupted with a heteroatom (O, S or NH) or a carbonyl group (CO), R.sub.2 and R.sub.3, which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms, y denotes an integer ranging from 0 to 3, and z denotes an integer ranging from 0 to 3, and x denotes an integer ranging from 0 to 2,
with z+x+y=3.

The invention also relates to a process for straightening keratin fibers, especially the hair, using the compounds of formulae (I) and (II) with a straightening step using a straightening iron at a temperature of at least 150° C., preferably ranging from 150 to 250° C.

Claims

1.-21. (canceled)

22. A cosmetic composition comprising: at least one compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof: ##STR00005## wherein in formula (I): R represents an atom or group chosen from i) hydrogen, ii) carboxyl —C(O)—OH, iii) linear or branched C.sub.1-C.sub.6 alkyl which is optionally substituted, iv) optionally substituted phenyl, v) optionally substituted benzyl, vi) an indolyl group, or vii) an imidazolylmethyl group and tautomers thereof, and compounds represented by the formula below: ##STR00006## and tautomers thereof, wherein * represents the part linked to the rest of the dicarbonyl compound; and at least one silane of formula (II) and/or oligomers thereof:
R.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x(OH).sub.y  (II) wherein in formula (II): R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.6 hydrocarbon-based chain substituted with a group chosen from the following groups: amine NH.sub.2 or NHR wherein R is chosen from C.sub.1-C.sub.20 alkyl and C.sub.1-C.sub.6 alkyl, optionally substituted with a group comprising a silicon atom, C.sub.3-C.sub.40 cycloalkyl or C.sub.6-C.sub.30 aromatic, a hydroxyl group, a thiol group, or an aryl or aryloxy group which is optionally substituted with an amino group or with a C.sub.1-C.sub.4 aminoalkyl group; R.sub.1 being optionally interrupted with a heteroatom, O, S, NH, or a carbonyl group (CO), R.sub.2 and R.sub.3, which may be identical or different, each represent a linear or branched C.sub.1-C.sub.6 alkyl group, y denotes an integer ranging from 0 to 3, z denotes an integer ranging from 0 to 3, and x denotes an integer ranging from 0 to 2, wherein z+x+y=3; wherein the cosmetic composition has a pH of less than 4.

23. The cosmetic composition according to claim 22, wherein R is chosen from a hydrogen atom; a linear or branched C.sub.1-C.sub.6 alkyl group optionally substituted with at least one hydroxyl —OH group, carboxyl —C(O)OH group, halogen, or Br; phenyl substituted with at least one —OH or —C(O)OH group; or benzyl substituted with at least one —OH or —C(O)OH group.

24. The cosmetic composition according to claim 22, wherein the at least one compound is chosen from glyoxylic acid or pyruvic acid; derivatives thereof, salts thereof, or hydrates thereof.

25. The cosmetic composition according to claim 22, wherein the at least one compound is chosen from glyoxylic acid esters, glyoxylic acid amides, glyoxylic acid acetals, glyoxylic acid hemiacetals, glyoxylic acid thioacetals, glyoxylic acid hemithioacetals, glyoxylic acid ester acetals, glyoxylic acid ester hemiacetals, glyoxylic acid ester thioacetals, and glyoxylic acid ester hemithioacetals; or derivatives thereof, hydrates thereof, or salts thereof.

26. The cosmetic composition according to claim 22, wherein the at least one compound is glyoxylic acid in its hydrate form.

27. The cosmetic composition according to claim 22, wherein the total amount of the compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof ranges from about 0.5% to about 15% by weight, relative to the total weight of the cosmetic composition.

28. The cosmetic composition according to claim 22, wherein: R.sub.2 is chosen from a C.sub.1-C.sub.4 alkyl group, a linear C.sub.1-C.sub.4 alkyl group, or an ethyl group; and R.sub.3 is chosen from a C.sub.1-C.sub.4 alkyl group, a linear C.sub.1-C.sub.4 alkyl group, a methyl group, or an ethyl group.

29. The cosmetic composition according to claim 22, wherein R.sub.1 represents a C.sub.1-C.sub.6 aminoalkyl group.

30. The cosmetic composition according to claim 22, wherein z is equal to 3.

31. The cosmetic composition according to claim 22, wherein: R.sub.1 is an acyclic chain, and the at least one silane of formula (II) comprises only one silicon atom in its structure.

32. The cosmetic composition according to claim 22, wherein the at least one silane of formula (II) is chosen from 3-aminopropyltriethoxysilane (APTES), 3-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m-aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, or N-(2-aminoethylaminomethyl)phenethyltrimethoxysilane; or oligomers thereof.

33. The cosmetic composition according to claim 22, comprising at least one compound chosen from 3-aminopropyltriethoxysilane or oligomers thereof.

34. The cosmetic composition according to claim 22, wherein the total active material content of silane of formula (II) and/or the oligomers thereof ranges from about 0.05% to about 20% by weight, relative to the total weight of the cosmetic composition.

35. The cosmetic composition according to claim 22, wherein the weight ratio of the total amount of the compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof to the total amount of silane of formula (II) and/or oligomers thereof ranges from about 0.1 to about 10.

36. The cosmetic composition according to claim 22, wherein the cosmetic composition is aqueous and comprises water in an amount ranging from about 5% to about 98% by weight, relative to the total weight of the composition.

37. The cosmetic composition according to claim 22, wherein the cosmetic composition has a pH ranging from 1 to 3.

38. The cosmetic composition according to claim 22, wherein the cosmetic composition may be obtained by mixing a first composition comprising at least one compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof, and a second composition comprising at least one silane.

39. A method for straightening hair, the method comprising: applying to the hair a composition A comprising: at least one compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof: ##STR00007## wherein in formula (I): R represents an atom or group chosen from i) hydrogen, ii) carboxyl —C(O)—OH, iii) linear or branched C.sub.1-C.sub.6 alkyl which is optionally substituted, iv) optionally substituted phenyl, v) optionally substituted benzyl, vi) an indolyl group, or vii) an imidazolylmethyl group and tautomers thereof, or compounds represented by the formula below: ##STR00008## and tautomers thereof, wherein * represents the part linked to the rest of the dicarbonyl compound; and at least one silane of formula (II) and/or oligomers thereof:
R.sub.1Si(OR.sub.2).sub.z(R.sub.3).sub.x(OH).sub.y  (II) wherein in formula (II): R.sub.1 is a linear or branched, saturated or unsaturated, cyclic or acyclic C.sub.1-C.sub.6 hydrocarbon-based chain substituted with a group chosen from the following groups:  amine NH.sub.2 or NHR wherein R is chosen from C.sub.1-C.sub.20 alkyl and C.sub.1-C.sub.6 alkyl, optionally substituted with a group comprising a silicon atom, C.sub.3-C.sub.40 cycloalkyl or C.sub.6-C.sub.30 aromatic,  a hydroxyl group,  a thiol group, or  an aryl or aryloxy group which is optionally substituted with an amino group or with a C.sub.1-C.sub.4 aminoalkyl group; R.sub.1 being optionally interrupted with a heteroatom, O, S, NH, or a carbonyl group (CO), R.sub.2 and R.sub.3, which may be identical or different, each represent a linear or branched C.sub.1-C.sub.6 alkyl group, y denotes an integer ranging from 0 to 3, z denotes an integer ranging from 0 to 3, and x denotes an integer ranging from 0 to 2, wherein z+x+y=3; wherein the composition A has a pH of less than 4; and performing a straightening step using a straightening device at a temperature of at least 150° C.

40. The method according to claim 39, further comprising allowing composition A to contact the keratin fibers for a contact time ranging from about 10 minutes to about 60 minutes.

41. The method according to claim 39, wherein: the step of applying composition A to the hair further comprises a successive application to the hair, in any order, with or without intermediate rinsing, of: a composition B comprising at least one compound chosen from dicarbonyl compounds of formula (I), derivatives thereof, hydrates thereof, or salts thereof, followed by allowing the composition B to contact the keratin fibers for a contact time ranging from about 10 minutes to about 60 minutes; and a composition C comprising at least one silane of formula (II) and/or oligomers thereof followed by allowing the composition C to contact the keratin fibers for a contact time ranging from about 10 minutes to about 60 minutes.

Description

EXAMPLES

[0137] The following compositions are prepared, compositions 1 and 2 being compositions in accordance with the invention and compositions C1 to C6 being comparative examples.

TABLE-US-00001 1 C1 C2 C3 2 C4 Glyoxylic acid 5 g 5 g — — — — Pyruvic acid — — — 8 g 8 g Aminopropyltriethoxysilane 5 g — 5 g 5 g 5 g — Water qs 100 g qs 100 g qs 100 g qs 100 g qs 100 g qs 100 g Sodium hydroxide/ qs pH 2.2 qs pH 2.2 — qs pH 2.2 qs pH 2.2 qs pH 2.2 hydrochloric acid

[0138] Process for a One-Step Use:

[0139] The compositions, optionally shaken before use, are applied at room temperature to curly hair, which may be natural or dyed, or sensitized by a prior bleaching step, at a rate of 1 g per 2 g of hair. After 15 minutes, the hair is rinsed, dried with a hairdryer (blow-drying) and then straightened by treating with flat tongs heated to 210° C. It is subsequently shampooed to examine the persistence of the straightening effects and of modification of the mechanical and cosmetic properties of the fibers.

[0140] Compositions C2 and C3 do not make it possible to obtain permanent straightening.

[0141] Composition 1 makes it possible to obtain straightening properties superior to those obtained with composition C1 and composition 2 makes it possible to obtain straightening properties superior to those obtained with composition C4, whether in terms of curl relaxation, protection of the natural or artificial color, resistance of the fibers to mechanical stresses (pulling, rubbing, twisting), sheen, smooth feel and smooth look.

[0142] Process for a Two-Step Use:

[0143] According to another process in two steps without rinsing, composition C2 or C3, or alternatively C1, is first applied to hair, at a rate of 1 g per 2 g of hair, the compositions are left to act for 15 minutes and then, without rinsing, 1 g per 2 g of hair of composition C1, or alternatively C2 or C3, is applied for 15 minutes. The hair is then dried (blow-drying) and then straightened by passing through flat tongs brought to 210° C. (10 passes on locks separated into two thicknesses).

[0144] The application of composition C1 combined with the application of compositions C2 or C3 leads to performance superior to that obtained with composition C1 used alone.

[0145] Similarly, composition C2 or C3, or alternatively C4, is first applied to hair, at a rate of 1 g per 2 g of hair, the compositions are left to act for 15 minutes and then, without rinsing, 1 g per 2 g of hair of composition C4, or alternatively C2 or C3, is applied for 15 minutes. The hair is then dried (blow-drying) and then straightened by passing through flat tongs brought to 210° C. (10 passes on locks separated into two thicknesses).

[0146] The application of composition C4 combined with the application of compositions C2 or C3 leads to performance superior to that obtained with composition C4 used alone.