# US 12,178,897 B2 · Oxidative dyeing agent for keratin fibers comprising novel dye precursor combinations

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- Number: US 12,178,897 B2
- Document ID: US12178897B2
- Status: Granted
- Kind: B2
- Application number: 18/111,365
- Filed: 2023-02-17
- Published: 2023-08-31
- Granted: 2024-12-31
- Earliest claimed: 2022-02-25
- Assignees: Henkel AG & Co. KGaA
- Applicants: Henkel AG & Co. KGaA
- Inventors: Razi Abbas; Tugce Cansev; Thomas Hippe; Astrid Kleen; Hartmut Manneck; Stefan Hoepfner; Tiffany Lea Fielder
- Web page: https://patentgrep.com/patent/US12178897B2

## CPC

- A61K 8/4973: {with oxygen as the only hetero atom}
- A61K 8/20: Halogens; Compounds thereof
- A61K 8/22: Peroxides; Oxygen; Ozone
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/347: {Phenols}
- A61K 8/411: {Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus}
- A61K 8/415: {Aminophenols}
- A61K 8/463: {containing sulfuric acid derivatives, e.g. sodium lauryl sulfate}
- A61K 8/4926: {having six membered rings}
- A61K 8/494: {with more than one nitrogen as the only hetero atom}
- A61K 8/498: {having 6-membered rings or their condensed derivatives, e.g. coumarin}
- A61K 8/8158: {Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers}
- A61Q 5/10: Preparations for permanently dyeing the hair
- A61K 2800/30: Characterized by the absence of a particular group of ingredients
- A61K 2800/882: Mixing prior to application
- 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

## Abstract

The subject of the present application is an agent for the oxidative dyeing of keratinous fibers, in particular human hair, which contains the coupling oxidation dye precursors 2-(1,3-benzodioxol-5-ylamino)ethanol and 1-phenyl-3-methylpyrazol-5-one in combination with at least one oxidation base.

## Claims

### Claim 1

An agent for the oxidative dyeing of keratinous fibers, comprising:
(A) a coupling oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino) ethanol and/or at least one of its physiologically tolerated salts, and
(B) a coupling oxidation dye precursor 1-phenyl-3-methylpyrazol-5-one and/or at least one of its physiologically tolerated salts, and
(C) at least one oxidation dye precursor, said oxidation dye precursor being an oxidation base-type,
wherein the agent is substantially free of any resorcinol compound of structure (1)
in which X means a hydrogen atom or a C1-C10 alkyl group,
wherein the agent is substantially free of dissolved hydrogen peroxide.

### Claim 2 (depends on 1)

The agent according to claim 1, wherein the coupling oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino) ethanol and/or at least one of its physiologically tolerated salts comprises 0.01 wt % to 5.0 wt % based on the total weight of the agent.

### Claim 3 (depends on 1)

The agent according to claim 1, wherein the coupling oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino) ethanol and/or at least one of its physiologically tolerated salts comprises 0.05 wt % to 1.5 wt % based on the total weight of the agent.

### Claim 4 (depends on 1)

The agent according to claim 1, wherein the coupling oxidation dye precursor 1-phenyl-3-methylpyrazol-5-one and/or at least one of its physiologically tolerated salts comprises 0.01 wt % to 1.0 wt % based on the total weight of the agent.

### Claim 5 (depends on 1)

The agent according to claim 1, wherein the coupling oxidation dye precursor 1-phenyl-3-methylpyrazol-5-one and/or at least one of its physiologically tolerated salts comprises 0.08 wt % to 0.2 wt % based on the total weight of the agent.

### Claim 6 (depends on 1)

The agent according to claim 1, wherein the at least one oxidation base is selected from the group consisting of: para-phenylenediamine, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diamino-phenyl) ethanol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, 4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole, 2-(1,2-dihydroxyethyl)-p-phenylenediamine, N,N′-bis-(2-hydroxyethyl)-N,N′-bis-(4-aminophenyl)-1,3-diamino-propane-2-ol, bis-(2-hydroxy-5-aminophenyl) methane, 1,3-bis-(2,5-diaminophenoxy)-propane-2-ol, N,N′-bis-(4-aminophenyl)-1,4-diazacycloheptane, 1,10-bis-(2,5-diaminophenyl)-1,4,7,10-tetraoxadecane, 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,3-diamino-6,7-dihydro-1H,5H-pyrazolo-[1,2-a]-pyrazole-1-one and their physiologically tolerated salts and mixtures of the aforementioned substances, their physiologically tolerated salts, and mixtures thereof.

### Claim 7 (depends on 1)

The agent according to claim 1, wherein the at least one oxidation base is selected from the group consisting of: para-phenylenediamine, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diamino-phenyl) ethanol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, 4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole, their physiologically tolerated salts, and mixtures thereof.

### Claim 8 (depends on 1)

The agent according to claim 1, wherein the at least one oxidation base and/or at least one of its physiologically tolerated salts is present comprises 0.001 wt % to 5.0 wt % based on the total weight of the agent.

### Claim 9 (depends on 1)

The agent according to claim 1, wherein the at least one oxidation base and/or at least one of its physiologically tolerated salts is present comprises 0.05 wt % to 1.5 wt % based on the total weight of the agent.

### Claim 10 (depends on 1)

The agent according to claim 1, wherein the agent further comprises at least one additional coupling oxidation dye precursor and/or at least one of its physiologically tolerated salts in an amount of 0.001 wt % to 5.0 wt % based on the total weight of the agent.

### Claim 11 (depends on 10)

The agent according to claim 10, wherein the at least one additional coupling oxidation dye precursor is 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, 1,3-phenylenediamine, 2-(2,4-diaminophenoxy) ethanol, 1-methoxy-2-amino-4-(2-hydroxyethylamino) benzene, 1,3-bis (2,4-diaminophenoxy) propane, 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, 3-amino-4-(2-methoxyethoxy)-5methylphenylamine, 1-amino-3-bis-(2-hydroxyethyl) aminobenzene, 2-amino-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 3,5-diamino-2,6-dimethoxypyridine, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2-methylresorcinol, 4-chlororesorcinol, 4-hydroxy-indole, 6-hydroxyindole, 7-hydroxyindole, 4-hydroxyindoline, 6-hydroxyindoline and/or 7-hydroxyindoline, their physiologically tolerated salts, and mixtures thereof.

### Claim 12 (depends on 10)

The agent according to claim 10, wherein the at least one additional coupling oxidation dye precursor is selected from the group consisting of: 3-aminophenol, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, 2-(2,4-diaminophenoxy) ethanol, 1-naphthol, 1-methoxy-2-amino-4-(2-hydroxy-ethylamino) benzene, 1,3-bis (2,4-diaminophenoxy) propane, 3-amino-2-methylamino-6-methoxypyridine, 2,7-dihydroxynaphthalene and their physiologically tolerated salts and mixtures of the aforementioned substances.

### Claim 13 (depends on 1)

The agent according to claim 1, wherein the agent further comprises polyquaternium-53.

### Claim 14 (depends on 13)

The agent according to claim 13, wherein the polyquaternium-53 is present in an amount of about 0.01 wt % to about 3 wt % based on the total weight of the agent.

### Claim 15 (depends on 1)

The agent according to claim 1, wherein the agent comprises a dye precursor mixture, which consists essentially of one of the following combinations, using the free bases or their physiologically tolerated salts:
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diaminophenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 5-amino-2-methylphenol and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diaminophenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 5-amino-2-methylphenol, 2,4-diaminophenoxyethanol and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diamino-phenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2,4-diaminophenoxyethanol and at least one of the oxidation bases para-phenylenediamine, N, N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diaminophenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2,4-diaminophenoxyethanol, 2-amino-3-hydroxypyridine, and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diamino-phenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2-amino-3-hydroxypyridine, and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diaminophenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2-amino-3-hydroxypyridine, 1-naphthol, and at least one of the oxidation bases para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol, 4-aminophenol, toluene-2,5-diamine, 2-methoxymethyl-para-phenylenediamine, 2-(2,5-diamino-phenyl) ethanol and mixtures of the aforementioned oxidation bases;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylene-diamine, 4-amino-3-methylphenol and 4-aminophenol;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 5-amino-2-methylphenol, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 5-amino-2-methylphenol, 2,4-diaminophenoxyethanol, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2,4-diaminophenoxyethanol, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2,4-diaminophenoxyethanol, 2-amino-3-hydroxypyridine, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol;
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2-amino-3-hydroxypyridine, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol; or
2-(1,3-benzodioxol-5-ylamino) ethanol, 1-phenyl-3-methylpyrazol-5-one, 3-aminophenol, 2-amino-3-hydroxypyridine, 1-naphthol, para-phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 4-amino-3-methylphenol and 4-aminophenol.

### Claim 16

A multicomponent kit-of-parts for oxidative dyeing of keratinous fibers, comprising at least two separately packaged components (C1) and (C2), wherein
the first component (C1) is substantially free of dissolved hydrogen peroxide, and comprises:
(A) the coupling oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino) ethanol and/or at least one of its physiologically tolerated salts, and
(B) the coupling oxidation dye precursor 1-phenyl-3-methylpyrazol-5-one and/or at least one of its physiologically tolerated salts, and
(C) at least one oxidation dye precursor of the oxidation base-type,
the second component (C2) is an aqueous hydrogen peroxide-containing composition with acidic pH wherein all components of the kit are free of any resorcinol compound of structure (1)
in which X means a hydrogen atom or a C1-C10 alkyl group.

### Claim 17 (depends on 1)

A process for the oxidative hair dyeing of keratinous fibers, comprising mixing an agent in accordance with claim 1 and an aqueous hydrogen peroxide-containing composition,
directly applying to keratinous fibers,
leaving on the keratinous fibers for a time of from 1 to 60 minutes at room temperature or higher, rinsing the keratinous fibers with water and/or a cleansing composition,
optionally, applying an aftertreatment agent to the keratinous fibers.