Symmetric azomethine direct dyes, process for their preparation, cosmetic composition comprising at least one such dye and use thereof

Patent metadata

Field	Value
Publication number	US-11504318-B2
Application number	US-201716467591-A
Country	US
Kind code	B2
Filing date	Dec 15, 2017
Priority date	Dec 16, 2016
Publication date	Nov 22, 2022
Grant date	Nov 22, 2022

Abstract

The present invention relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, in one or more steps, comprising the application to said keratin fibres of a composition comprising one or more compounds of formula (I) and/or (II), and also to the use thereof for dyeing keratin fibres, and to a device: in which formula (I) or (II) R 1 , R 3 , R 4 , R 5 , R 6 , and n are as defined in the description. The compounds of formula (I) according to the invention can give powerful, chromatic and sparingly selective colourings with good colour build-up, which are resistant to the various attacking factors to which keratin fibres may be subjected, such as inclement weather, light, washing and perspiration.

First claim

The invention claimed is:

1. A method for dyeing keratin fibers, comprising applying to said keratin fibers a composition comprising at least one compound selected from compounds of formula (I) or (II) below, organic or mineral acid or base salts thereof, tautomers thereof, optical isomers thereof, geometrical isomers thereof, or solvates thereof:

wherein formulae (I) and (II):
n represents an integer equal to 0, 1, 2, 3, 4 or 5;
R 1 represents:
a halogen atom,
a sulfonic radical —SO 3 H or sulfonate radical —SO 3 − , M + ;
a carboxyl radical —CO 2 H, a carboxylate radical —COO − ;
an aromatic or non-aromatic, 5- to 10-membered cationic heterocycle, which is optionally substituted with one or more identical or different radicals chosen from C 1 -C 4 alkyl and C 1 -C 4 hydroxyalkyl;
an aromatic or non-aromatic, 5- to 6-membered non-cationic heterocycle, substituted with:
an ammonium radical —N + RR′R″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with one or more hydroxyl groups, or
an aromatic or non-aromatic, 5- to 10-membered cationic heterocycle, which is optionally substituted with one or more identical or different radicals chosen from C 1 -C 4 alkyl and C 1 -C 4 hydroxyalkyl,

an ammonium radical —N + RR′R″, wherein R, R′ and R″, which may be identical or different, represent a C 1 -C 4 alkyl group, or
a radical —W—R 7 , wherein:
W represents:
 an oxygen or sulfur atom,
 a divalent group —N(R 8 )— or
 a linear or branched, saturated or unsaturated, divalent hydrocarbon-based chain, comprising from 1 to 14 carbon atoms, said hydrocarbon-based chain being:
 optionally substituted with one or more radicals, which may be identical or different, chosen from the following radicals: i) hydroxyl, ii) (di)(C 1 -C 6 )(alkyl)amino, iii) ammoniums —N + RR′R″, iv) aromatic or non-aromatic, optionally substituted, 5- to 10-membered cationic heterocycles, v) aromatic or non-aromatic, 5- or 6-membered non-cationic heterocycles, substituted with one or more radicals, which may be identical or different, chosen from the following radicals: a) ammonium —N + RR′R″, and b), aromatic or non-aromatic, 5- to 10-membered cationic heterocycle, optionally substituted with one or more identical or different radicals chosen from C 1 -C 4 alkyl;
 and/or
 optionally interrupted, optionally starting, and/or optionally terminating with one or more divalent heteroatoms or groups, which may be identical or different, chosen from:
 —O—, —S—, —N(R 10 )—, —S(O)—, —S(O) 2 —, and —C(X)— with X representing an oxygen or sulfur atom or a group NR 10 and R 10 representing a hydrogen atom or a (C 1 -C 6 )alkyl group, and
 combinations thereof;
R 7 and R 8 , which may be identical or different, represent:
 a hydrogen atom,
 a linear or branched C 1 -C 14 alkyl group, said alkyl group being:
 optionally interrupted with one or more heteroatoms or groups selected from —O—, —S—, —N(R 10 )—, —S(O)—, —S(O) 2 —, —C(X)—, or combinations thereof; or

optionally substituted with one or more radicals, which may be identical or different, chosen from the following radicals: i) hydroxyl, ii) (di)(C 1 -C 6 )(alkyl)amino, iii) ammoniums —N + RR′R″, iv) aromatic or non-aromatic, optionally substituted, 5- to 10-membered cationic heterocycles, v) aromatic or non-aromatic, 5- or 6-membered non-cationic heterocycles, substituted with one or more radicals, which may be identical or different, chosen from the following radicals: a) ammonium —N + RR′R″, or b), aromatic or non-aromatic, 5- to 10-membered cationic heterocycle, optionally substituted with one or more identical or different radicals chosen from C 1 -C 4 alkyl; R 3 and R 4 , which may be identical or different, representing a hydrogen atom;
R 5 and R 6 , which may be identical or different, represent an atom or group chosen from:
a hydrogen a t om,
a halogen atom,
a C 1 -C 6 alkyl radical,
a (C 1 -C 6 )alkyl radical substituted with one or more radicals chosen from the following radicals: i) hydroxyl, ii) amino —NH 2 , iii) (C 1 -C 6 )alkylamino, and iv) di(C 1 -C 6 )alkylamino,
a (C 1 -C 6 )alkoxy radical, or
a (C 1 -C 6 )alkoxy radical substituted with one or more radicals chosen from the following radicals: i) hydroxyl, ii) amino, iii) (C 1 -C 6 )alkylamino, and iv) di(C 1 -C 6 )alkylamino,

wherein:
the compounds of formulae (I) and (II) are symmetric,
when the compound of formula (I) or (II) is cationic, it optionally comprises one or more anions An − and optionally one or more cations M + to ensure the electrical neutrality of the molecule;
wherein:
An − denoting an anion chosen from bromide, chloride, a methylsulfate ion, a toluenesulfonate ion, or a mixture thereof;
M + representing a cation chosen from sodium, potassium, magnesium, calcium, or ammonium.

2. The method according to claim 1 , further comprising:
applying an oxidizing composition, wherein the oxidizing composition comprises at least one chemical oxidizing agent chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids, or oxidase enzymes; wherein the fibers are optionally rinsed, washed, or dried between the first and second steps.

3. The method according to claim 1 , wherein the composition comprising the at least one compound of formula (I) and/or (II) further comprises at least one chemical oxidizing agent chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, perborates, persulfates, peracids, or oxidase enzymes (with the optional cofactors thereof, wherein the method optionally further comprises at least one step chosen from rinsing, washing, or drying the keratin fibers.

4. The method according to claim 1 , wherein R 5 and R 6 represent a hydrogen atom.

5. The method according to claim 1 , wherein R 1 represents:
a sulfonic radical —SO 3 H or sulfonate radical —SO 3 − , M + ;
a hydrogen atom;
a radical —W′—R′ 7 , wherein:
W′ represents an oxygen or sulfur atom or a divalent group —N(R′ 8 )—;
R′ 7 and R′ 8 , which may be identical or different, represent a linear or branched, saturated or unsaturated alkyl group, comprising from 1 to 8 carbon atoms, said hydrocarbon-based chain being:
optionally substituted with one or more radicals, which may be identical or different, chosen from the following radicals: i) hydroxyl, ii) (di)(C 1 -C 6 )(alkyl)amino, iii) ammoniums —N + RR′R″, iv) aromatic or non-aromatic, 5- to 10-membered cationic heterocycles, optionally substituted with at least one (C 1 -C 4 )alkyl group chosen from (C 1 -C 4 )(alkyl)imidazoliums, (C 1 -C 4 )(alkyl)piperaziniums, (C 1 -C 4 )(alkyl)pyrrolidiniums, (C 1 -C 4 )(alkyl)piperidiniums, morpholiniums, v) aromatic or non-aromatic, 5- or 6-membered non-cationic heterocycles, substituted with a radical chosen from the following radicals: a) ammonium —N + RR′R″, An − , and b), aromatic, 5- to 10-membered cationic heterocycle, optionally substituted with one or more radicals, which may be identical or different, chosen from C 1 -C 4 alkyl; or
optionally interrupted with one or more divalent heteroatoms or groups, which may be identical or different, chosen from:
—O—, —N(R 10 )—, and —C(O)—, or
combinations thereof;

R′ 7 , and R′ 8 , which may be identical or different, represent:
a hydrogen atom,
a linear or branched C 1 -C 14 , said alkyl group being:
optionally interrupted with at least one heteroatom or group, which may be identical or different, chosen from —O—, —S—, —N(R 10 )—, —S(O)—, —S(O) 2 —, —C(X)—, or combinations thereof; or
optionally substituted with one or more radicals, which may be identical or different, chosen from the followin

Assignees

• Oreal

Inventors

• Sabelle Stéphane
• Blais Stéphane
• Fadli Aziz

Classifications

• A61K8/4946 Primary

  Imidazoles or their condensed derivatives, e.g. benzimidazoles · CPC title

• A61K8/415

  Aminophenols · CPC title

• A61K8/413

  Indoanilines; Indophenol; Indoamines · CPC title

• C09B55/009

  Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image) · CPC title

• C09B55/002

  Monoazomethine dyes · CPC title