# US 2017/0281501 A1 · 4,5-diaminoimidazoles as novel developer-type oxidation dye precursors

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- Number: US 2017/0281501 A1
- Document ID: US20170281501A1
- Status: Published application
- Kind: A1
- Application number: 15/479,136
- Filed: 2017-04-04
- Published: 2017-10-05
- Earliest claimed: 2016-04-05
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Antje Gebert-Schwarzwalder; Helmut Giesa; Jan-Michael Schonebeck
- Web page: https://patentgrep.com/patent/US20170281501A1

## CPC

- A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles}
- A61Q 5/10: Preparations for permanently dyeing the hair
- C07C 211/09: Diamines
- C07C 211/18: containing at least two amino groups bound to the carbon skeleton
- C07D 233/24: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C09B 57/00: Other synthetic dyes of known constitution
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

An agent for oxidative changing of the color of keratin fibers, in particular human hair, includes, in a cosmetic support, as a developer-type oxidation dye precursor, at least one compound of formula (I) as further defined herein.

## Claims

### Claim 1

An agent for oxidative changing of the color of keratin fibers, in particular human hair, including, in a cosmetic support, as a developer-type oxidation dye precursor, at least one compound of formula (I)
wherein
R1, R2 independently of one another stand for hydrogen, a C1-C6 alkyl group, a C2-C6 alkenyl group, a hydroxy C1-C6 alkyl group, a polyhydroxy C2-C6 alkyl group, a C1-C6-alkyloxy C2-C6 alkyl group, an amino C1-C6 alkyl group, a polyamino C2-C6 alkyl group, a di(C1-C6-alkyl)amino C1-C6 alkyl group, a C1-C6 alkanoyl group, an aryl group or an aryl C1-C6 alkyl group,
R3, R4 independently of one another stand for hydrogen, a C1-C6 alkyl group, a C2-C6 alkenyl group, a hydroxy C1-C6 alkyl group, a polyhydroxy C2-C6 alkyl group, a C1-C6-alkyloxy C2-C6 alkyl group, an amino C1-C6 alkyl group, a polyamino C2-C6 alkyl group, a di(C1-C6-alkyl)amino C1-C6 alkyl group, a C1-C6 alkanoyl group, an aryl group or an aryl C1-C6 alkyl group,
R5, R6 independently of one another stand for hydrogen, a C1-C6 alkyl group, a C2-C6 alkenyl group, a hydroxy C1-C6 alkyl group, an aryl group or an aryl C1-C6 alkyl group,
and/or a physiologically compatible salt thereof.

### Claim 2 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R1 and R2 independently of one another stand for hydrogen or a C1-C6 alkanoyl group.

### Claim 3 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R1 and R2 both stand for hydrogen.

### Claim 4 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R3 and R4 independently of one another stand for hydrogen, a C1-C6 alkyl group or a C1-C6 alkanoyl group.

### Claim 5 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R5 stands for hydrogen or for a C1-C6 alkyl group.

### Claim 6 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R5 stands for a methyl group or an ethyl group.

### Claim 7 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I) in which R6 stands for hydrogen.

### Claim 8 (depends on 1)

The agent according to claim 1, wherein the agent includes at least one compound of formula (I), which is selected from the group consisting of
1H-imidazole-4,5-diamine
1-methyl-1H-imidazole-4,5-diamine
1-ethyl-1H-imidazole-4,5-diamine
4-N-methyl-1H-imidazole-4,5-diamine
1,4-N-dimethyl-1H-imidazole-4,5-diamine
1-ethyl-4-N-methyl-1H-imidazole-4,5-diamine
4-N-ethyl-1H-imidazole-4,5-diamine
4-N-ethyl-1-methyl-1H-imidazole-4,5-diamine
1,4-N-diethyl-1H-imidazole-4,5-diamine
5-N-methyl-1H-imidazole-4,5-diamine
1,5-N-dimethyl-1H-imidazole-4,5-diamine
1-ethyl-5-N-methyl-1H-imidazole-4,5-diamine
5-N-ethyl-1-H-imidazole-4,5-diamine
5-N-ethyl-1-methyl-1H-imidazole-4,5-diamine
1,5-N-diethyl-1H-imidazole-4,5-diamine
4-N,5-N-dimethyl-1H-imidazole-4,5-diamine
1,4-N,5-N-trimethyl-1H-imidazole-4,5-diamine
1-ethyl-4-N,5-N-dimethyl-1H-imidazole-4,5-diamine
4-N-ethyl-5-N-methyl-1H-imidazole-4,5-diamine
4-N-ethyl-1,5-N-dimethyl-1H-imidazole-4,5-diamine
1,4-N-diethyl-5N-methyl-1H-imidazole-4,5-diamine
5-N-ethyl-4-N-methyl-1H-imidazole-4,5-diamine
5-N-ethyl-1,4-N-dimethyl-1H-imidazole-4,5-diamine
1-5-N-diethyl-4N-methyl-1H-imidazole-4,5-diamine
4-N, 5-N-diethyl-1H-imidazole-4,5-diamine
4-N, 5-N-diethyl-1-methyl-1H-imidazole-4,5-diamine
1,4-N, 5-N-triethyl-1H-imidazole-4,5-diamine
N-(5-amino-1H-imidazole-4-yl)acetamide
N-(5 -amino-1-methyl-1H-imidazole-4-yl)acetamide
N-(5-amino-1-ethyl-1H-imidazole-4-yl)acetamide
N-(4-amino-1H-imidazole-5-yl)acetamide
N-(4-amino-1-methyl-1H-imidazole-5-yl)acetamide
N-(4-amino-1-ethyl-1H-imidazole-5-yl)acetamide
N-acetyl-N-(5-amino-1H-imidazole-4-yl)acetamide
N-acetyl-N-(5-amino-1-methyl-1H-imidazole-4-yl)acetamide
N-acetyl-N-(5-amino-1-ethyl-1H-imidazole-4-yl)acetamide
N-acetyl-N-(4-amino-1H-imidazole-5-yl)acetamide
N-acetyl-N-(4-amino-1-methyl-1H-imidazole-5-yl)acetamide
N-acetyl-N-(4-amino-1-ethyl-1H-imidazole-5-yl)acetamide
and the physiologically compatible salts of such compounds.

### Claim 9 (depends on 1)

The agent according to claim 1, wherein the agent includes one or more compounds of formula (I) in a total quantity of from 0.001 to 5.0 wt.% relative to the total weight of the agent.

### Claim 10 (depends on 1)

The agent according to claim 1, further including at least one coupler-type oxidation dye precursor selected from the group consisting of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4-chloro-2-methylphenol, 5-(2-hydroxyethyl)-amino-2-methylphenol, 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′-hydroxyethyleneamino)-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-morpholine-4-yl phenyl)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-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 4-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole, 4-hydroxyindolin, 6-hydroxyindolin, 7-hydroxyindolin, and physiologically compatible salts of such compounds.