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EP-4734948-A1 - PROCESS FOR TREATING KERATIN FIBRES EMPLOYING AT LEAST ONE THIOPYRIDINONE COMPOUND

EP4734948A1EP 4734948 A1EP4734948 A1EP 4734948A1EP-4734948-A1

Abstract

The present invention relates to a process for treating keratin fibres, in particular human keratin fibres, such as the hair, comprising bringing into contact with said keratin fibres at least one compound of formula (I) or (I'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates. The invention also relates to one or more compounds of formula (II) or (II'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates. The invention also relates to a process for treating keratin fibres, in particular human keratin fibres, such as the hair, comprising bringing into contact with said keratin fibres at least one compound of formula (III) or (III'), as described hereinafter, and the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates.

Inventors

  • SARI, Ozkan
  • GREAVES, ANDREW
  • GENARD, SYLVIE

Assignees

  • L'OREAL

Dates

Publication Date
20260506
Application Date
20240626

Claims (20)

  1. 1. Process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said keratin fibres of at least one compound of the following formula (I) or (!'), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same: (I) (I') in which formulae (I) and (!'): Ri denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3; R2 denotes a cyclic or acyclic radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, ii) -S-R3, iii) -C(0)-0-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-, or c) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; R3 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; R4 denotes a radical selected from the group consisting of a) a hydrogen atom, b) a saturated, linear Ci-Cio or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; X represents an oxygen atom, a sulfur atom, preferably an oxygen atom; R' represents a hydrogen atom or a C1-C4, in particular Ci, alkyl group, and preferably represents a hydrogen atom; it being understood that when R4 denotes e) an ammonium group, the electroneutrality of the compounds of formula (I) or (!') is ensured by one or more cosmetically acceptable anions such as halides preferably selected from chloride or bromide.
  2. 2. Process according to Claim 1, characterized in that Ri represents a) a hydrogen atom.
  3. 3. Process according to Claim 1 or 2, characterized in that R3 represents a) a hydrogen atom or a saturated, linear Ci-Ce or branched C3-C6 alkyl group, and preferably R3 represents a) a hydrogen atom.
  4. 4. Process according to any one of the preceding claims, characterized in that R4 represents a) a hydrogen atom, b) a saturated linear Ci-Ce, in particular C1-C4, alkyl group, or c) an alkali metal.
  5. 5. Process according to any one of the preceding claims, characterized in that R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; said hydrocarbon group being interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.
  6. 6. Process according to any one of Claims 1 to 4, characterized in that R2 denotes b) a saturated, linear C1-C12 or branched C3-C12 hydrocarbon group, substituted by one or more groups iii) -C(O)-O-R4; said hydrocarbon group being additionally optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3, ii) -S-R3, and iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; said hydrocarbon group being additionally optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-.
  7. 7. Process according to any one of the preceding claims, characterized in that the compound(s) of formulae (I) and (f) is or are selected from the group consisting of the compounds of formula (II) or (If), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof: (II) (If) in which formulae (II) and (If): - A represents a divalent, saturated or unsaturated, preferably saturated, cyclic or acyclic, preferably acyclic, linear or branched hydrocarbon chain comprising from 1 to 10 carbon atoms, interrupted by one or more (thio)amide groups -C(X)-N(R')- or (NR')-C(X)-, and optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3; - M denotes a radical selected from the group consisting of a) a hydrogen atom, b) a linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; preferably M represents a) a hydrogen atom or d) an alkali metal; - Ri has the same meaning as in Claim 1 or 2; preferably, Ri represents a hydrogen atom; - R3 has the same meaning as in Claim 1 or 3; preferably, R3 represents a hydrogen atom; - X has the same meaning as in Claim 1; preferably X represents an oxygen atom; - R' has the same meaning as in Claim 1; preferably R' represents a hydrogen atom.
  8. 8. Process according to Claim 7, characterized in that A represents a linear or branched, preferably linear, (C2-Ce)alkylene group; said chain A being interrupted by a -C(X)-N(R')- group with X and R' as defined in Claim 7, more particularly interrupted by a -C(O)-N(H)- group; in particular, A represents a group CH2-C(O)-N(R')-CH2- or -CH2-N(R')-C(X)-CH2- with X and R' as defined in Claim 7, preferably A represents a -CH 2 -C(O)-N(H)-CH 2 - group.
  9. 9. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) or (P), the compounds of formula (II) or (IP) is or are selected from the group consisting of the compounds of formula (IIA) or (IIB) below, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof: (IIA) (IIB) in which formulae (IIA) and (IIB): - Ra and Rb independently of one another denote a hydrogen atom or a C1-C4 alkyl radical optionally substituted by one or more hydroxy (OH) or thiol (SH) radicals; and - n and m independently denote an integer equal to 1 or 2 or 3; preferably n and m are identical and are equal to 1; - M has the same meaning as for the compounds of formula (II) or (If); in particular, M represents a hydrogen atom, an alkali metal, or an alkyl, linear or branched, C1-C4 alkyl group such as methyl or ethyl, preferably a hydrogen atom or an alkali metal such as sodium or potassium.
  10. 10. Process according to any one of the preceding claims, characterized in that the compound(s) of formula (I) or (!'), the compounds of formula (II) or (If), the compounds of formula (IIA) or (IIB) is or are selected from the compounds of formulae (Ila) to (Hi) or (IPa) to (IPi) below, and also the tautomers thereof, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof: with M as defined above, in particular M represents a hydrogen atom, an alkali metal, or a linear or branched C1-C4 alkyl group such as methyl or ethyl, more preferentially a hydrogen atom or an alkali metal such as sodium or potassium.
  11. 11. Process according to any one of the preceding claims, characterized in that the compounds of formula (I) or (!'), the compounds of formula (II) or (If), the compounds of formula (IIA) or (IIB) are selected from the compounds of formula (II- 1) or (II'l) or (II-2) or (11'2) below, and also the organic or mineral acid or base salts thereof, in particular the sodium or potassium salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof:
  12. 12. Process according to any one of Claims 1 to 4, characterized in that the thiopyridinone compound(s) of formulae (I) and (P) is or are selected from the group consisting of the compounds of formula (III) or (IIP), and also one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof: (III) (IIP) in which formulae (III) and (IIP): - Ri is as defined in formula (I) or (P), R2 denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from: i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, and iv) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals, and c) a C5-C12 aryl group, optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals, and - R3 denotes a radical selected from the group consisting of: a) a hydrogen atom, and b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; and R4 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group.
  13. 13. Process according to any one of Claims 1 to 4 or 12, characterized in that the compound(s) of formula (I) or (P) or the compounds of formula (III) or (IIP) are selected from the group consisting of the compounds III-l to III-24 below, the tautomers thereof, the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof: in particular the compounds III-l, III-2, III-4, III-6, III-7, III-9, III-l 1, III-12, ni-14, III-l 5, III-16, HI-17, HI-18, III-19, III-20 or III-21, more particularly III-l, III-9, III- 16, III-l 8, III- 19, III-20 or III-21, preferably III- 18, III- 19, III-20 or III-21, and more preferably the compound of formula III-20.
  14. 14. Process according to any one of the preceding claims, characterized in that the keratin fibres are sensitized, preferably dyed and/or bleached, in particular bleached.
  15. 15. Process according to any one of the preceding claims, characterized in that it comprises at least shaping keratin fibres, preferably a temporary shaping of the keratin fibres, carried out by using mechanical means such as curlers or by treating said keratin fibres with an iron, or a long-lasting shaping of the keratin fibres.
  16. 16. Use of at least one compound of formula (I) or (!'), as defined according to any one of Claims 1 to 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl containing same, for shaping keratin fibres, in particular human keratin fibres, such as the hair.
  17. 17. Use according to Claim 16, characterized in that the compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (II) or (If), as defined according to any one of Claims 7 to 11, the compounds of formula (III) or (IIP), as defined according to Claim 12 or 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.
  18. 18. Use according to Claim 16 or 17, characterized in that the compound(s) of formula (I) or (P) is or are selected from the group consisting of the compounds of formula (III) or (IIP), as defined according to Claim 12 or 13, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.
  19. 19. Compound of formula (II) or (IP), as defined according to any one of Claims 7 to 11, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.
  20. 20. Composition C2 comprising at least one compound of formula (II) or (IP), as defined according to Claim 19, and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof.

Description

DESCRIPTION TITLE: Process for treating keratin fibres employing at least one thiopyridinone compound The present invention relates to a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least bringing into contact with said keratin fibres at least one compound of formula (I) or (P), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and/or the solvates thereof such as the hydrates, or at least one composition Cl comprising same. The invention also relates to one or more compounds of formula (II) or (If), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and the solvates thereof such as the hydrates. The invention also relates to a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least bringing into contact with said keratin fibres at least one compound of formula (III) or (IIP), as described hereinafter, and/or the optical isomers and geometrical isomers thereof, and also the organic or mineral acid or base salts thereof, and/or the solvates thereof such as the hydrates, or at least one composition comprising same. Styling products are hair compositions usually used to build and structure the hairstyle and to give it hold. Such compositions generally comprise one or more film-forming polymers or "fixing polymers", enabling the formation of a coating film on the fibres so as to ensure hold of the hairstyle and/or the formation of micro-welds between the fibres, thus resulting in the fixing of the head of hair. Such compositions are usually in the form of lotions, gels, foams or sprays and are commonly applied to wet hair, which is shaped before blow-drying or drying. However, the shaping conferred by such styling products has the drawback of fading more or less rapidly over time and/or following one or more washes. In other words, such styling products generally lead to a shape-retention of the fibres which is still too often unsatisfactory. Such compositions may also lead to unsatisfactory shaping of the hair, in particular when they are applied to hair which has been sensitized, in particular by one or more chemical treatments, for example at least one relaxing, permanent waving, dyeing and/or bleaching process. There is thus a real need to implement a process for cosmetic treatment of keratin fibres, in particular human keratin fibres, such as the hair, which does not have the drawbacks mentioned above, that is to say which is capable of shaping keratin fibres, including keratin fibres which have been sensitized by at least one chemical treatment, for example at least one relaxing, permanent waving, dyeing and/or bleaching process, and to do so in a long-lasting manner. A subject of the present invention is therefore a process for shaping keratin fibres, in particular human keratin fibres, such as the hair, comprising at least the application to said keratin fibres of at least one compound of the following formula (I) and/or (T), and/or one of the organic or mineral acid or base salts thereof, the solvates thereof, such as the hydrates thereof, the optical isomers thereof, the geometrical isomers thereof, and mixtures thereof, or of at least one composition Cl comprising same: (I) (I') in which formulae (I) and (T): Ri denotes a radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear Ci-Cio or branched C3-C10 alkyl group optionally substituted by one or more groups which may be identical or different and are selected from the group consisting of i) -O-R3 and ii) -S-R3; R2 denotes a cyclic or acyclic radical selected from the group consisting of: a) a hydrogen atom, b) a saturated, linear C1-C12 or branched C3-C12 or cyclic C3-C8 hydrocarbon group, optionally substituted by one or more groups which may be identical or different and are selected from i) -O-R3, ii) -S-R3, iii) -C(O)-O-R4, iv) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; said hydrocarbon group being optionally interrupted by one or more heteroatoms or groups, such as an oxygen atom, a sulfur atom, an NR' or (thio)carbonyl group, or combinations thereof such as (thio)ester or (thio)amide(s), C(X)-N(R')- or -N(R')-C(X)-, or c) a C5-C12 aryl group optionally substituted by one or more hydroxyls and/or by one or more Ci-Cs alkoxy radicals; R3 denotes a radical selected from a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group; R4 denotes a radical selected from the group consisting of a) a hydrogen atom, b) a saturated, linear C1-C10 or branched C3-C10 alkyl group, c) an alkali metal, d) an alkaline earth metal, or e) an ammonium group; X represents an oxygen atom, a sulfur atom, preferably an oxygen atom; R' represent