Use of dihydroisoquinolinium double derivatives for treating keratin materials, compositions and implementation processes

Patent metadata

Field	Value
Publication number	US-11406579-B2
Application number	US-201616064129-A
Country	US
Kind code	B2
Filing date	Dec 23, 2016
Priority date	Dec 23, 2015
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

The present invention relates to the use of one or more dihydroisoquinolinium double salts for treating keratin materials, in particular keratin fibres, especially human keratin fibres such as the hair. The invention also relates to a process for treating keratin materials using said salts and optionally in the presence of one or more chemical oxidizing agents. A subject of the invention is also a composition for lightening keratin materials, comprising one or more dihydroisoquinolinium double salts as defined below and one or more chemical oxidizing agents. The present invention also relates to one or more particular dihydroisoquinolinium double salts and also to compositions containing them, in particular compositions comprising a physiologically acceptable medium.

First claim

The invention claimed is:

1. A method for lightening human hair, the method comprising:
applying to said human hair at least one compound of formula (I), the tautomeric forms thereof, the addition salts thereof, or the solvates thereof optionally in the presence of at least one chemical oxidizing agent:

wherein in formula (I):
R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R′ 1 , R′ 2 , R′ 3 , R′ 5 , R′ 6 , R′ 7 , R′ 8 , R′ 9 and R′ 10 , independently of each other, are chosen from:
a hydrogen atom;
a halogen atom,
a C 1 -C 6 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C 1 -C 6 alkoxy, cyano, or amino —NR a R b groups,
a C 1 -C 6 alkoxy radical;
a hydroxyl radical;
an amino radical —NR a R b ,
an aminocarbonyl radical —CONH 2 , or
a carboxyl radical —CO 2 H,

R 4 and R′ 4 together form a divalent radical L such that L is chosen from a linear or branched, saturated or unsaturated C 1 -C 15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur,
R a and R b are chosen from, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 6 alkyl radical,
Anion denotes an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (I).

2. The method according to claim 1 , wherein a radical chosen from the radicals R i and a radical chosen from the radicals R′ j when i=j, together form:
a divalent radical L representing a linear or branched, saturated or unsaturated C 1 -C 15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, or
a single bond.

3. The method according to claim 1 , wherein a radical chosen from the radicals R i and a radical chosen from the radicals R′ j when i and j are identical and are equal to 3 or 4, together form a divalent radical L, or a covalent single bond.

4. The method according to claim 1 , wherein:
R 1 and R′ 1 are identical to each other, R 2 and R′ 2 are identical to each other, R 3 and R′ 3 are identical to each other, R 5 and R′ 5 are identical to each other, R 6 and R′ 6 are identical to each other, R 7 and R′ 7 are identical to each other, R 8 and R′ 8 are identical to each other, R 9 and R′ 9 are identical to each other, R 10 and R′ 10 are identical to each other and, independently from one pair to another, are chosen from
a hydrogen atom;
a halogen atom,
a C 1 -C 6 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, cyano, C 1 -C 6 alkoxy, or amino NR a R b groups,
a C 1 -C 6 alkoxy radical;
a hydroxyl radical;
an amino radical NR a R b ,
an aminocarbonyl radical —CONH 2 , or
a carboxyl radical —CO 2 H,

R 4 and R′ 4 together form a divalent radical L such that L is chosen from a linear or branched, saturated or unsaturated C 1 -C 15 alkylene radical, optionally substituted with at least one hydroxyl group and/or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur,
R a and R b , independently of each other, are chosen from a hydrogen atom or a linear or branched, saturated or unsaturated C 1 -C 6 alkyl radical.

5. The method according to claim 1 , wherein:
R 1 , R′ 1 , R 2 , R′ 2 , R 3 , R′ 3 , R 5 , R′ 5 , R 6 , R′ 6 , R 7 , R′ 7 , R 8 , R′ 8 , R 9 and R′ 9 denote a hydrogen atom,
R 4 and R′ 4 together form a divalent radical L such that L represents a saturated linear C 1 -C 15 alkylene radical, optionally substituted with at least one hydroxyl group or interrupted with at least one non-adjacent heteroatom chosen from oxygen, nitrogen, or sulfur, L optionally denoting a saturated, linear or branched C 2 -C 10 alkylene radical, optionally substituted with at least one hydroxyl group or interrupted with at least one non-adjacent heteroatom chosen from oxygen.

6. The method according to claim 1 , wherein the at least one compound of formula (I), the tautomeric forms thereof, the addition salts thereof, and/or the solvates thereof are chosen from the following compounds, the tautomeric forms thereof, the addition salts thereof, and/or the solvates thereof:

2,2′-butane-1,4- diyldi-3,4 dihydroisoquinolinium dibromide Compound 1

2,2′-ethane-1,4-diyldi- 3,4 dihydroisoquinolinium dibromide Compound 2

2,2′-propane-1,4- diyldi-3,4 dihydroisoquinolinium dibromide Compound 3

2,2′-pentane-1,4- diyldi-3,4 dihydroisoquinolinium dibromide Compound 4

2,2′-(2- hydroxypropane-1,3- diyl)di-3,4- dihydroisoquinolinium dibromide Compound 5

2,2′-hexane-1,4- diyldi-3,4- dihydroisoquinolinium dibromide Compound 6

2,2′-[2,2- bis(hydroxymethyl)pro- propane-1,3-diyl]di-3,4- dihydroisoquinolinium dibromide Compound 7

2,2′-(oxydiethane-2,1- diyl)di-3,4- dihydroisoquinolinium dibromide Compound 8

Assignees

• Oreal

Inventors

• Sabelle Stéphane
• Fadli Aziz

Classifications

• C07D401/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A61Q5/08

  Preparations for bleaching the hair · CPC title

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title

• A61K2800/4322

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

• A61K8/4926 Primary

  having six membered rings · CPC title