Substituted p-phenylenediamines as new oxidation dye precursor products of the developer type

Patent metadata

Field	Value
Publication number	US-10004674-B2
Application number	US-201615379083-A
Country	US
Kind code	B2
Filing date	Dec 14, 2016
Priority date	Dec 15, 2015
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

Compounds, and agents for oxidatively changing the color of keratinic fibers that include such compounds, in particular human hair, in a cosmetic carrier. The compounds are at least one oxidation dye precursor product of formula (I) and/or physiologically acceptable salt thereof,

in which
R1, R2, R3, R4 independently of one another, stand for a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a hydroxy-(C 1 -C 6 )-alkyl group, a polyhydroxy-(C 2 -C 6 )-alkyl group, or a C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl group,
n stands for an integer from 2 to 6, and
Z stands for an aromatic or aliphatic heterocycle or for an aromatic or aliphatic carbocycle.

First claim

What is claimed is:

1. An agent for oxidatively changing the color of keratinic fibers, in particular human hair, including, in a cosmetic carrier, at least one oxidation dye precursor product of formula (I) and/or physiologically acceptable salt thereof,

in which
R1, R2, R3, R4 independently of one another, stand for a hydrogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a hydroxy-(C 1 -C 6 )-alkyl group, a polyhydroxy-(C 2 -C 6 )-alkyl group, or a C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl group,
n stands for an integer from 3 to 6, and
Z stands for an aromatic or aliphatic heterocycle or for an aromatic or aliphatic carbocycle.

2. The agent according to claim 1 , wherein
R1, R2, R3, R4 independently of one another, stand for a hydrogen atom, a C 1 -C 6 -alkyl group or a 2-(hydroxy)ethyl group.

3. The agent according to claim 1 , wherein
one of the groups from R1, R2, R3 and R4 stands for a C 1 -C 6 alkyl group, and the other three groups from R1, R2, R3 and R4 stand for a hydrogen atom.

4. The agent according to claim 1 , wherein
R3, R4 both stand for a hydrogen atom.

5. The agent according to claim 1 , wherein
R1 stands for a methyl group or for a hydrogen atom, and
R2 stands for a hydrogen atom.

6. The agent according to claim 1 , wherein
Z stands for an aromatic or aliphatic heterocycle of formulas (II) to (X),

wherein
R5 stands for a hydrogen atom, a C 1 -C 6 alkyl group or a C 2 -C 6 alkenyl group.

7. The agent according to claim 6 , wherein
Z stands for an aromatic or aliphatic heterocycle of formula (II), (III), (IV) or (V).

8. The agent according to claim 1 , wherein
Z stands for an aromatic or aliphatic carbocycle of formulas (XI) to (XIII),

9. The agent according to claim 1 , wherein the at least one oxidation dye precursor product of formula (I) is selected from the group consisting of
1-N-methyl-2-[3-(pyrrolidin-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(piperidin-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(morpholin-4-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(1H-pyrrol-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(1H-pyrazol-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(1H-imidazol-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(piperazin-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(4-methylpiperazin-1-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(thiomorpholin-4-yl)propyl]benzene-1,4-diamine

1-N-methyl-2-[3-(2,5-dihydro-1H-pyrrol-1-yl)propyl]benzene-1,4-diamine

2-[3-(pyrrolidin-1-yl)propyl]benzene-1,4-diamine

2-[3-(piperidin-1-yl)propyl]benzene-1,4-diamine

2-[3-(morpholin-4-yl)propyl]benzene-1,4-diamine

2-[3-(1H-pyrrol-1-yl)propyl]benzene-1,4-diamine

2-[3-(1H-pyrazol-1-yl)propyl]benzene-1,4-diamine

2-[3-(1H-imidazol-1-yl)propyl]benzene-1,4-diamine

2-[3-(piperazin-1-yl)propyl]benzene-1,4-diamine

2-[3-(4-methylpiperazin-1-yl)propyl]benzene-1,4-diamine

2-[3-(thiomorpholin-4-yl)propyl]benzene-1,4-diamine

2-[3-(2,5-dihydro-1H-pyrrol-1-yl)propyl]benzene-1,4-diamine

and the physiologically acceptable salts of these compounds.

10. The agent according to claim 1 , wherein the one or more oxidation dye precursor products of formula (I) is/are included in a total amount of from 0.001 to 5.0% by weight, in relation to the total weight of the agent.

11. The agent according to claim 1 , further including one or more oxidation dye precursor products selected from the group consisting of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxy ethanol, 5-amino-4-chloro-2-methylphenol, 5-(2-hydroxyethyl)-amino-2-methyl phenol, 2,4-dichloro-3-aminophenol, 2-aminophenol, 3-phenylenediamine, 2-(2,4-diaminophenoxy)ethanol, 1,3-bis(2,4-diaminophenoxy)propane, 1-methoxy-2-amino-4-(2-hydroxyethylamino)benzene, 1,3-bis(2,4-diaminophenyl)propane, 2,6-bis(2′-hydroxyethylamino)-1-methylbenzene, 2-({3-[(2-hydroxyethyl)amino]-4-methoxy-5-methylphenyl}amino)ethanol, 2-({3-[(2-hydroxyethyl)amino]-2-methoxy-5-methylphenyl}amino)ethanol, 2-({3-[(2-hydroxyethyl) amino]-4,5-dimethylphenyl}amino)ethanol, 2-[3-morpholin-4-ylphenyl)amino]ethanol, 3-amino-4-(2-methoxyethoxy)-5-methylphenylamine, 1-amino-3-bis-(2-hydroxyethyl)aminobenzene, resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 1,2,4-trihydroxybenzene, 2-amino-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 3,5-diamino-2,6-dimethoxypyridine, 1-phenyl-3-methylpyrazol-5-one, 1-naphthol, 1,5-dhydroxynaphthaline, 2,7-dihydroxynaphthaline, 1,7-dihydroxynaphthaline, 1,8-dihydroxynaphthaline, 4-hydroxyindol, 6-hydroxyindol, 7-hydroxyindol, 4-hydroxyindolin, 6-hydroxyindolin, 7-hydroxyindolin, and the physiologically acceptable salts thereof.

12. The agent according to claim 1 , further including one or more oxidation dye precursor products selected from the group consisting of p-phenylenediamine, p-toluenediamine, 2-(2-hydroxyethyl)-p-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N-(4-amino-3-methylphenyl)-N-[3-(1H-imidazol-1-yl)propyl]amine, bis-(2-hydroxy-5-aminophenyl)methane,

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Gebert-Schwarzwaelder Antje
• Giesa Helmut
• Schoenebeck Jan-Michael

Classifications

• A61K2800/4324

  in preparations for permanently dyeing the hair · CPC title

• A61K8/49

  containing heterocyclic compounds · CPC title

• A61K8/411

  Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus · CPC title

• C07D295/04

  with substituted hydrocarbon radicals attached to ring nitrogen atoms · CPC title

• C07D241/06

  having one or two double bonds between ring members or between ring members and non-ring members · CPC title