# US 12,109,291 B2 · Oxidative dyeing agent for keratin fibers comprising novel dye precursor combinations > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,109,291 B2 - Document ID: US12109291B2 - Status: Granted - Kind: B2 - Application number: 18/111,117 - Filed: 2023-02-17 - Published: 2023-10-05 - Granted: 2024-10-08 - 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/US12109291B2 ## CPC - A61K 8/4973: {with oxygen as the only hetero atom} - A61K 8/411: {Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus} - A61Q 5/10: Preparations for permanently dyeing the hair - A61K 2800/30: Characterized by the absence of a particular group of ingredients - A61K 2800/4324: in preparations for permanently dyeing the hair - 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 precursor 2-(1,3-benzodioxol-5-ylamino)ethanol in combination with the oxidation base 2-methoxymethyl-para-phenylenediamine. ## 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) an oxidation base 2-methoxymethyl-para-phenylenediamine and/or at least one of its physiologically tolerated salts, wherein the agent is substantially free of any resorcinol compound of structure (I) in which X means a hydrogen atom or a C1-C10 alkyl group, wherein the agent is further substantially free of any chlorinated aromatic nitro dyes, and wherein the agent is further substantially free of dissolved hydrogen peroxide. ### Claim 2 (depends on 1) The agent according to claim 1, wherein the 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 oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino)ethanol and/or at least one of its physiologically tolerated salts comprises 0.03 wt % to 3.0 wt % based on the total weight of the agent. ### Claim 4 (depends on 1) The agent according to claim 1, wherein the 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 5 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-p-phenylenediamine 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 6 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-p-phenylenediamine and/or at least one of its physiologically tolerated salts comprises 0.03 wt % to 3.0 wt % based on the total weight of the agent. ### Claim 7 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-p-phenylenediamine 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 8 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-para-phenylenediamine or at least one of its physiologically tolerated salts (B) and the oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino)ethanol or at least one of its physiologically tolerated salts (A) are present at a molar ratio (B)/(A) of 1.0 to 2.3. ### Claim 9 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-para-phenylenediamine or at least one of its physiologically tolerated salts (B) and the oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino)ethanol or at least one of its physiologically tolerated salts (A) are present at a molar ratio (B)/(A) of 1.1 to 2.0. ### Claim 10 (depends on 1) The agent according to claim 1, wherein the oxidation base 2-methoxymethyl-para-phenylenediamine or at least one of its physiologically tolerated salts (B) and the oxidation dye precursor 2-(1,3-benzodioxol-5-ylamino)ethanol or at least one of its physiologically tolerated salts (A) are present at a molar ratio (B)/(A) of 1.3 to 1.6. ### Claim 11 (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 a total amount of 0.001 wt % to 5.0% based on the total weight of the agent. ### Claim 12 (depends on 11) The agent according to claim 11, 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)-5-methylphenylamine, 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-phenyl-3-methylpyrazol-5-one, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 4-chlororesorcinol, 4-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole, 4-hydroxyindoline, 6-hydroxyindoline and/or 7-hydroxyindoline, their physiologically tolerated salts, and mixtures of the aforementioned substances. ### Claim 13 (depends on 1) The agent according to any claim 1, wherein the agent further comprises at least one additional oxidation base and/or at least one of its physiologically tolerated salts in a total amount of 0.001 wt % to 5.0 wt % based on the total weight of the agent. ### Claim 14 (depends on 13) The agent according to claim 13, wherein the at least one additional oxidation base is selected from the group consisting of: 4,5-diamino-1-(2-hydroxyethyl)-1H-pyrazole, 2-(2,5-diaminophenyl)ethanol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, toluene-2,5-diamine, 4-amino-3-methylphenol, 4-aminophenol, p-phenylenediamine, 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, their physiologically tolerated salts, and mixtures of the aforementioned substances. ### Claim 15 (depends on 1) The agent according to claim 1, further comprisesing polyquaternium-53 in an amount of about 0.01 wt % to about 3 wt % based on the total weight of the agent. ### Claim 16 (depends on 1) The agent according to claim 1, further comprisesing polyquaternium-53 in an amount of about 0.05 wt % to about 2 wt % based on the total weight of the agent. ### Claim 17 (depends on 1) The agent according to claim 1, further comprisesing polyquaternium-53 in an amount of about 0.1 wt % to about 1 wt % based on the total weight of the agent. ### Claim 18 (depends on 1) The agent according to claim 1, further comprisesing polyquaternium-53 in an amount of about 0.2 wt % to about 0.7 wt % based on the total weight of the agent. ### Claim 19 A multicomponent kit-of-parts for oxidative dyeing of keratinous fibers, comprising at least two separately packaged components (C1) and (C2), wherein a 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 oxidation base 2-methoxymethyl-para-phenylenediamine and/or at least one of its physiologically tolerated salts, a second component (C2) being an aqueous hydrogen peroxide-containing composition with acidic pH, wherein all components of the kit are free of any resorcinol compound of structure (I) in which X means a hydrogen atom or a C1-C10 alkyl group, wherein all components of the kit are further substantially free of any chlorinated aromatic nitro dyes. ### Claim 20 (depends on 1) A process for the oxidative dyeing of keratinous fibers, comprising mixing an agent of claim 1 with an aqueous hydrogen peroxide-containing composition yielding a ready-to-use composition, applying the read-to-use mixture to keratinous fibers and leaving the composition on the keratinous fibers for a period of time of 1 to 60 minutes at room temperature or higher, rinsing the keratinous fibers with water and/or cleaning composition, and optionally applying to the keratinous fibers an aftertreatment agent, and/or optionally drying the keratinous fibers.