Use of substituted dihydroisoquinolinium salts for treating keratin materials, compositions and implementation processes

Patent metadata

Field	Value
Publication number	US-11083679-B2
Application number	US-201616064291-A
Country	US
Kind code	B2
Filing date	Dec 23, 2016
Priority date	Dec 23, 2015
Publication date	Aug 10, 2021
Grant date	Aug 10, 2021

Abstract

The present invention relates to the use of one or more particular dihydroisoquinolinium salts of formula (I) 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 one or more chemical oxidizing agents. A subject of the invention is also a composition for lightening keratin materials, comprising one or more dihydroisoquinolinium salts and one or more chemical oxidizing agents. The present invention also relates to one or more particular dihydroisoquinolinium 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 treating keratin materials comprising applying to said keratin materials, optionally in the presence of one or more chemical oxidizing agents, at least one compound chosen from:
(a) compounds of formula (I), the addition salts thereof, or the solvates thereof:

wherein in formula (I):
R is chosen from:
a linear or branched C 1 -C 12 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 10 R 11 groups;

R 1 is chosen from:
a linear or branched C 1 -C 12 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C 1 -C 6 alkoxy, or amino —NR 10 R 11 groups;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 , are chosen from, independently of each other, a radical chosen from:
a hydrogen atom,
a halogen atom,
a linear or branched 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, or amino —NR 10 R 11 groups,
a C 1 -C 6 alkoxy radical,
a hydroxyl radical,
an amino radical —NR 10 R 11 , or
an aminocarbonyl radical —CONH 2 ;

R 10 and R 11 , which may be identical or different, are chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical;
with the proviso that R, R 2 , R 3 , R 4 and R 5 cannot all be identical; and
An − represents an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (I); or

(b) 2,3,3-trimethyl-3,4-dihydroisoquinolinium toluene-4-sulfonate (Compound 2):

2. The method according to claim 1 , wherein R 4 , R 5 , R 6 and R 9 are identical and represent a hydrogen atom.

3. The method according to claim 1 , wherein R 7 and R 8 are identical and represent a hydrogen atom or a C 1 -C 6 alkoxy radical.

4. The method according to claim 1 , wherein the compound of formula (I) is chosen from the compounds of formula (II), the addition salts thereof, or the solvates thereof:

wherein in formula (II):
R is chosen from:
a linear or branched C 1 -C 12 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 10 R 11 groups;

R 1 is chosen from:
a linear or branched C 1 -C 12 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C 1 -C 6 alkoxy, or amino —NR 10 R 11 groups;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are chosen from, independently of each other, a radical chosen from:
a hydrogen atom,
a halogen atom,
a linear or branched 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, or amino —NR 10 R 11 groups, or
an aminocarbonyl radical —CONH 2 ;

R 10 and R 11 , which may be identical or different, are chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical;
with the proviso that R, R 2 , R 3 , R 4 and R 5 cannot all be identical; and
An − represents an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (II).

5. The method according to claim 4 , wherein R 2 and R 3 are identical and represent a hydrogen atom or a linear or branched 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, or amino —NR 10 R 11 groups.

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

7. The method according to claim 4 , wherein R 6 , R 7 , R 8 and R 9 are identical and represent a hydrogen atom.

8. The method according to claim 1 , wherein the compound of formula (I) is chosen from the following compounds:

1,2,3,3-tetramethyl- 3,4-dihydroisoquinolinium toluenesulfonate (Compound 1)

6,7-dimethoxy- 1,2-dimethyl-,3,4- dihydroisoquinolinium toluene-4-sulfonate (Compound 3)

1-(cyanomethyl)-2- methyl-3,4- dihydroisoquinolinium tetrafluoroborate (Compound 4)

or mixtures thereof.

9. A method for improving the oxidizing activity of at least one chemical oxidizing agent, the method comprising combining at least one chemical oxidizing agent with a compound chosen from:
(a) compounds of formula (I), the addition salts thereof, or the solvates thereof:

wherein in formula (I):
R is chosen from:
a linear or branched C 1 -C 12 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 10 R 11 groups;

R 1 is chosen from:
a linear or branched C 1 -C 12 alkyl radical optionally substituted with at least one group, which may be identical or different, chosen from hydroxyl, C 1 -C 6 alkoxy, or amino —NR 10 R 11 groups;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 , are chosen from, independently of each other, a radical chosen from:
a hydrogen atom,
a halogen atom,
a linear or branched 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, or amino —NR 10 R 11 groups,
a C 1 -C 6 alkoxy radical,
a hydroxyl radical,
an amino radical —NR 10 R 11 , or
an aminocarbonyl radical —CONH 2 ;

R 10 and R 11 , which may be identical or different, are chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical;
with the proviso that R, R 2 , R 3 , R 4 and R 5 cannot all be identical; and
An − represents an organic or mineral anion or mixture of anions which ensures the electrical neutrality of the compounds of formula (I); or

(b) 2,3,3-trimethyl-3,4-dihydroisoquinolinium toluene-4-sulfonate (Compound 2):

10. A composi

Assignees

• Oreal

Inventors

• Sabelle Stéphane
• Fadli Aziz
• Charrier Alexandra

Classifications

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• A61K8/49

  containing heterocyclic compounds · CPC title

• A61Q5/08

  Preparations for bleaching the hair · CPC title

• A61K8/4926 Primary

  having six membered rings · CPC title

• A61K8/22

  Peroxides; Oxygen; Ozone · CPC title