# US 12,109,289 B2 · Compositions for imparting color and tone to the hair > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,109,289 B2 - Document ID: US12109289B2 - Status: Granted - Kind: B2 - Application number: 17/853,722 - Filed: 2022-06-29 - Published: 2023-02-09 - Granted: 2024-10-08 - Earliest claimed: 2021-06-30 - Assignees: L'oreal - Applicants: L'Oreal - Inventors: Minli Shi; Kimberly Dreher; Leslie Warner; Brian Kluck - Web page: https://patentgrep.com/patent/US12109289B2 ## CPC - A61K 8/41: Amines - A61K 8/342: {Alcohols having more than seven atoms in an unbroken chain} - A61K 8/362: Polycarboxylic acids - A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids - A61K 8/39: Derivatives containing from 2 to 10 oxyalkylene groups - A61K 8/411: {Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus} - A61K 8/415: {Aminophenols} - A61K 8/42: Amides - A61K 8/44: Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof - A61K 8/466: {containing sulfonic acid derivatives; Salts} - A61K 8/55: Phosphorus compounds - A61K 8/92: Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof - A61Q 5/10: Preparations for permanently dyeing the hair - A61K 2800/43: Pigments; Dyes - A61K 2800/596: Mixtures of surface active compounds - 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 present disclosure relates to compositions for altering the tone or color of the hair comprising at least one amino acid, at least one carboxylic acid, monoethanolamine, at least one oxidation base chosen from toluene-2,5-diamine, acid salts thereof, or solvates thereof, and a coupler system comprising one or more couplers chosen from 2,4-diaminophenoxyethanol, meta-aminophenol, derivatives thereof, addition salts thereof, solvates thereof, solvates of salts thereof, or mixtures thereof. The disclosure also relates to methods of using the compositions and kits comprising the compositions. ## Claims ### Claim 1 A hair color toning composition comprising: (a) at least one amino acid; (b) at least one carboxylic acid; (c) monoethanolamine, present in an amount ranging from about 0.01% to about 1.3% by weight, relative to the total weight of the composition; (d) a surfactant mixture comprising (i) at least one amphoteric surfactant, and (ii) at least one surfactant chosen from anionic surfactants or non-ionic surfactants; (e) at least one fatty compound; (f) at least one oxidation base chosen from toluene-2,5-diamine, acid salts thereof, or solvates thereof; (g) a coupler comprising at least one coupler chosen from: (I) 2,4-diaminophenoxyethanol, derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; (II) meta-aminophenol (1-hydroxy-3-aminobenzene), derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; or (III) mixtures thereof; and (h) at least one solvent, wherein the hair color toning composition has a pH ranging from about 7 to about 10.4. ### Claim 2 (depends on 1) The hair color toning composition according to claim 1, wherein the at least one amino acid is chosen from taurine, alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine, or mixtures thereof. ### Claim 3 (depends on 1) The hair color toning composition according to claim 1, wherein the total amount of amino acids ranges from about 0.05% to about 5% by weight, relative to the total weight of the composition. ### Claim 4 (depends on 1) The hair color toning composition according to claim 1, wherein the at least one carboxylic acid is chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, sebacic acid, maleic acid, fumaric acid, benzoic acid, citraconic acid, aconitic acid, trimesic acid, propane-1,2,3-tricarboxylic acid, or mixtures thereof. ### Claim 5 (depends on 1) The hair color toning composition according to claim 1, wherein the at least one carboxylic acid comprises citric acid. ### Claim 6 (depends on 1) The hair color toning composition according to claim 1, wherein the total amount of carboxylic acids ranges from about 0.01% to about 3% by weight, relative to the weight of the composition. ### Claim 7 (depends on 1) The hair color toning composition according to claim 1, wherein the at least one fatty compound is chosen from C12-C22 fatty alcohols. ### Claim 8 (depends on 1) The hair color toning composition according to claim 1, wherein the total amount of oxidation base ranges from about 0.001% to about 20% by weight, relative to the total weight of the composition. ### Claim 9 (depends on 1) The hair color toning composition according to claim 1, wherein the total amount of coupler ranges from about 0.001% to about 20% by weight, relative to the total weight of the composition. ### Claim 10 (depends on 1) The hair color toning composition according to claim 1, further comprising: (i) one or more additional oxidative bases chosen from p-aminophenol, N, N-bis((2-hydroxyethyl)-p-phenylenediamine sulfate, Hydroxypropyl bis (N-hydroxyethyl-p-phenylenediamine) HCl, O-Aminophenol, N-methyl-p-aminophenol sulfate, N-methyl-p-aminophenol sulfate, 2,3-Diaminohydropyrazolo pyrazolone dimethosulfate, 1-Hydroxyethyl 4,5-diamino pyrazole sulfate, 2-[(3-1-Aminopyrazolo[1,5-A]pyridin-2-yl)oxy]ethanol hydrochloride, derivatives thereof, addition salts thereof, solvates thereof, solvates of salts thereof, or mixtures thereof, and/or (ii) one or more additional couplers chosen from hydroxybenzomorpholine (hydroxy-6-benzomorpholine), 2-amino-3-hydroxypyridine, m-aminophenol, 2-methyl-5-hydroxyethylaminophenol, hydroxy-6-indole, 2-amino-3-hydroxypyridine, 5-amino-6-chloro-o-cresol, 1-naphthol, derivatives thereof, addition salts thereof, solvates thereof, solvates of salts thereof, or mixtures thereof. ### Claim 11 (depends on 1) The hair color toning composition according to claim 1, further comprising at least one conditioning agent. ### Claim 12 (depends on 1) The hair color toning composition according to claim 1, wherein the monoethanolamine is present in the composition in an amount ranging from about 0.1% to about 1.3% by weight, relative to the total weight of the composition. ### Claim 13 (depends on 1) The hair color toning composition according to claim 1, wherein the at least one amino acid comprises taurine and the at least one carboxylic acid comprises citric acid. ### Claim 14 A method for altering the tone or color of the hair, comprising mixing (i) a hair color toning composition with (ii) an oxidizing composition to form a mixture having a pH ranging from about 6.0 to about 6.8, and applying the mixture to the hair, wherein: (i) the hair color toning composition comprises: (a) at least one amino acid, (b) at least one carboxylic acid, (c) monoethanolamine, present in an amount ranging from about 0.01% to about 1.3% by weight, relative to the total weight of the composition, (d) a surfactant mixture comprising (i) at least one amphoteric surfactant and (ii) at least one surfactant chosen from anionic or non-ionic surfactants, (e) at least one fatty compound, (f) at least one oxidation base chosen from toluene-2,5-diamine, acid salts thereof, or solvates thereof; (g) a coupler system comprising at least one coupler chosen from: (I) 2,4-diaminophenoxyethanol, derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; (II) meta-aminophenol (1-hydroxy-3-aminobenzene), derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; or (III) mixtures thereof; and (h) at least one solvent; wherein the hair color toning composition has a pH ranging from about 7 to about 10.4, and (ii) the oxidizing composition comprises at least one oxidizing agent. ### Claim 15 (depends on 14) The method according to claim 14, wherein the at least one amino acid is chosen from taurine, alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine, or mixtures thereof. ### Claim 16 (depends on 14) The method according to claim 14, wherein the total amount of amino acid ranges from about 0.05% to about 5% by weight, relative to the weight of the hair color toning composition. ### Claim 17 (depends on 14) The method according to claim 14, wherein the at least one carboxylic acid is chosen from oxalic acid, malonic acid, glutaric acid, succinic acid, adipic acid, glycolic acid, citric acid, tartaric acid, malic acid, sebacic acid, maleic acid, fumaric acid, benzoic acid, citraconic acid, aconitic acid, trimesic acid, propane-1,2,3-tricarboxylic acid, or mixtures thereof. ### Claim 18 (depends on 14) The method according to claim 14, wherein the total amount of carboxylic acids ranges from about 0.01% to about 3% by weight, relative to the weight of the hair color toning composition. ### Claim 19 A hair color toning composition comprising: (a) from about 0.1% to about 2% taurine by weight, relative to the weight of the composition, (b) from about 0.1% to about 3% citric acid by weight, relative to the weight of the composition, (c) from about 0.1% to about 1.3% monoethanolamine by weight, relative to the weight of the composition, (d) at least one surfactant, (e) at least one fatty compound chosen from C12-C22 fatty alcohols, (f) at least one oxidation base chosen from toluene-2,5-diamine, acid salts thereof, or solvates thereof; (g) at least one coupler chosen from 2,4-diaminophenoxyethanol HCl, derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; meta-aminophenol, derivatives thereof, addition salts thereof, solvates thereof, or solvates of salts thereof; or mixtures thereof; and (h) at least one solvent, wherein the hair color toning composition has a pH ranging from about 8.5 to about 10. ### Claim 20 (depends on 19) The hair color toning composition according to claim 19, wherein the coupler comprises 2,4-diaminophenoxyethanol HCl and meta-aminophenol.