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

Patent metadata

Field	Value
Publication number	US-10927259-B2
Application number	US-201716467352-A
Country	US
Kind code	B2
Filing date	Dec 15, 2017
Priority date	Dec 16, 2016
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

The compounds of formula (I) or (II) 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 compound chosen from compounds of formulae (I) and/or (II) below, organic or mineral acid or base salts thereof, tautomeric forms thereof, optical isomers thereof, geometrical isomers thereof, or solvates thereof:

wherein formulae (I) and (II):
n and n′, which may be identical or different, represent an integer equal to 0, 1, 2, 3, 4 or 5;
R 1 and R 2 , which may be identical or different, represent:
a halogen atom;
a sulfonic radical —SO 3 H or sulfonate radical —SO 3 − ;
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″, An − with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, and/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″, An − , with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group;
amino;
hydroxyl, or thiol;
a radical —W—R 7 , in which:
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, the 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″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, 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″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, 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; 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 wherein R 10 represents a hydrogen atom or a (C 1 -C 6 )alkyl group, 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 alkyl group, 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 8 )—, —S(O)—, —S(O) 2 —, or —C(X)— with X representing an oxygen or sulfur atom or a group NR 10 wherein R 10 represents a hydrogen atom or a (C 1 -C 6 )alkyl group, or combinations thereof; and/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″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, iv) aromatic or non-aromatic, optionally substituted, 5- to 10-membered cationic heterocycles, optionally substituted with one or more (C 1 -C 4 )alkyl groups, 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″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, 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,
a (C 1 -C 6 )alkyl radical optionally substituted with at least one radical chosen from i) hydroxyl, ii) (C 1 -C 4 )alkoxy, iii) amino, iv) (C 1 -C 6 )alkylamino, or v) di(C 1 -C 6 )alkylamino;

R 5 and R 6 , which may be identical or different, represent an atom or group chosen from:
a hydrogen atom,
a halogen atom,
a C 1 -C 6 alkyl radical,
a (C 1 -C 6 )alkyl radical substituted with at least one radical chosen from the following radicals: i) hydroxyl, ii) amino —NH 2 , iii) (C 1 -C 6 )alkylamino, or 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, or iv) di(C 1 -C 6 )alkylamino,

it being understood that:
the compounds of formulae (I) and (II) are dissymmetric,
the sum of n+n′ is greater than or equal to 1,
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;
with:
An − denoting an anion chosen from bromide, chloride, methylsulfate, toluenesulfonate ions, or a mixture of these ions; and
M + representing a cation chosen from sodium, potassium, magnesium, calcium, or ammonium.

2. The compound of formulae (I) or (II) according to claim 1 , wherein R 3 and R 4 represent a hydrogen atom.

3. The compound of formulae (I) or (II) according to claim 1 , wherein R 5 and R 6 represent a hydrogen atom.

4. The compound of formulae (I) or (II) according to claim 1 , wherein n represents an integer equal to 0 or 1.

5. The compound of formulae (I) or (II) according to claim 1 , wherein R 1 and R 2 , which may be identical or different, represent:
a sulfonic radical —SO 3 H or sulfonate radical —SO 3 − ;
a radical —W—R′ 7 , in which:
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″ with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, 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 a radical chosen from the following radicals: a) ammonium —N + RR′R″, An − with R, R′ and R″, which may be identical or different, representing a (C 1 -C 4 )alkyl group optionally substituted with at least one hydroxyl group, and b) aromatic, 5- to 10-membered cationic heterocycle, optionally substituted with one o

Assignees

• Oreal

Inventors

• Sabelle Stéphane
• Blais Stéphane
• Fadli Aziz

Classifications

• A61K2800/4322

  in preparations for temporarily coloring the hair further containing an oxidizing agent · CPC title

• A61K8/466

  containing sulfonic acid derivatives; Salts · CPC title

• A61K8/415

  Aminophenols · CPC title

• C09B55/009

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

• A61K2800/884

  Sequential application · CPC title