# US 7,608,116 B2 · Oxidation dye composition comprising at least one mesomorphic phase, process for preparing it and ready-to-use composition for dyeing keratin materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,116 B2 - Document ID: US7608116B2 - Status: Granted - Kind: B2 - Application number: 10/743,004 - Filed: 2003-12-23 - Published: 2004-10-07 - Granted: 2009-10-27 - Earliest claimed: 2002-12-24 - Assignees: L'oreal - Inventors: Luc Nicolas-Morgantini; Jean-Marc Petit - Web page: https://patentgrep.com/patent/US7608116B2 ## CPC - A61K 8/0295: {Liquid crystals} - A61K 8/375: {the alcohol moiety containing more than one hydroxy group} - A61Q 5/10: Preparations for permanently dyeing the hair - 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 oxidation dye compositions comprising, in an aqueous medium suitable for dyeing, at least one oxidation dye, ammonia, and at least one mesomorphic phase present in an amount greater than or equal to 10% by weight, relative to the weight of the composition. The present disclosure also relates to the process for preparing the compositions, as well as ready-to-use compositions for oxidation dyeing of keratin fibers, and multi-compartment kits for oxidation dyeing of keratin fibers, wherein at least one compartment contains the dye composition. Another aspect of the present disclosure is an oxidizing composition comprising a mesomorphic phase. ## Claims ### Claim 1 A dye composition comprising, in an aqueous medium suitable for dyeing, at least one oxidation dye, ammonia, and at least one mesomorphic phase present in an amount greater than or equal to 10% by weight, relative to the total weight of the dye composition, the at least one mesomorphic phase comprising at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of the dye composition, the at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2). ### Claim 2 (depends on 1) The dye composition according to claim 1, wherein the at least one mesomorphic phase is present in an amount greater than or equal to 15% by weight, relative to the total weight of the dye composition. ### Claim 3 (depends on 1) The dye composition according to claim 1, wherein the at least one mesomorphic phase is present in an amount ranging from 10% to 85% by weight, relative to the total weight of the dye composition. ### Claim 4 (depends on 1) The dye composition according to claim 1, wherein the at least one mesomorphic phase is chosen from a lamellar phase Lβ. ### Claim 5 (depends on 1) The dye composition according to claim 1, wherein the at least one mesomorphic phase comprises at least one nonionic surfactant with an HLB value ranging from 1 to 5. ### Claim 6 (depends on 1) The dye composition according to claim 1, wherein the at least one non ionic surfactant is chosen from polyglycerolated fatty alcohols, monooxyethylenated or polyoxyethylenated fatty alcohols, monoglycerolated or polyglycerolated fatty amides comprising from 1 to 5 glycerol groups, monooxyethylenated or polyoxyethylenated alkylphenols comprising greater than or equal to 2 mol of ethylene oxide, condensates of ethylene oxide and of propylene oxide with fatty alcohols, polyoxyethylenated vegetable oils comprising more than 5 mol of ethylene oxide, fatty acid esters of polyethylene glycols, and polyoxyethylenated fatty acid esters of sorbitol. ### Claim 7 (depends on 6) The dye composition according to claim 6, wherein the nonionic surfactant is hexadecyl alcohol comprising 2 mol of glycerol. ### Claim 8 (depends on 1) The dye composition according to claim 1, wherein the at least one mesomorphic phase further comprises at least one fatty alcohol comprising from 8 to 30 carbon atoms. ### Claim 9 (depends on 8) The dye composition according to claim 8, wherein the at least one fatty alcohol is hexadecanol. ### Claim 10 (depends on 8) The dye composition according to claim 8, wherein the at least one fatty alcohol is present in the composition in an amount ranging from 3% to 20% by weight, relative to the total weight of the dye composition. ### Claim 11 (depends on 10) The dye composition according to claim 10, wherein the at least one fatty alcohol is present in the composition in an amount ranging from 5% to 15% by weight, relative to the total weight of the dye composition. ### Claim 12 (depends on 1) The dye composition according to claim 1, wherein the ammonia is present in the composition in an amount ranging from 0.1% to 5% by weight, relative to the total weight of the dye composition. ### Claim 13 (depends on 12) The dye composition according to claim 12, the ammonia is present in the composition in an amount ranging from 1% to 3% by weight, relative to the total weight of the dye composition. ### Claim 14 (depends on 1) The dye composition according to claim 1, wherein the at least one oxidation dye is chosen from oxidation bases and couplers. ### Claim 15 (depends on 14) The dye composition according to claim 14, wherein the oxidation dye is chosen from at least one oxidation base. ### Claim 16 (depends on 15) The dye composition according to claim 15, wherein the at least one oxidation base is chosen from ortho- and para-phenylenediamines, double bases, ortho- and para-aminophenols and heterocyclic bases, and the acid addition salts thereof. ### Claim 17 (depends on 16) The dye composition according to claim 16, wherein the para-phenylenediamines are chosen from the compounds of formula (I): wherein: R1 is chosen from hydrogen, a C1-C4 alkyl group, a C1-C4 monohydroxyalkyl group, a C2-C4 polyhydroxyalkyl group, a (C1-C4)alkoxy(C1-C4)alkyl group, a C1-C4 alkyl group substituted with a nitrogenous group, a phenyl group, and a 4′-aminophenyl group; R2 is chosen from hydrogen, a C1-C4 alkyl group, a C1-C4 monohydroxyalkyl group, a C2-C4 polyhydroxyalkyl group, a (C1-C4)alkoxy(C1-C4)alkyl group and a C1-C4 alkyl group substituted with a nitrogenous group; wherein R1 and R2 may also form, with the nitrogen atom that bears them, a 5- or 6-membered nitrogenous heterocycle optionally substituted with at least one group chosen from alkyl, hydroxy and ureido groups; R3 is chosen from hydrogen, halogens, a C1-C4 alkyl group, a sulfo group, a carboxy group, a C1-C4 monohydroxyalkyl group, a C1-C4 hydroxyalkoxy group, an acetylamino(C1-C4)alkoxy group, a mesylamino(C1-C4)alkoxy group and a carbamoylamino(C1-C4)alkoxy group, R4 is chosen from hydrogen, halogens, and C1-C4 alkyl groups. ### Claim 18 (depends on 17) The dye composition according to claim 17, wherein the nitrogenous groups are chosen from amino, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, tri(C1-C4)alkylamino, monohydroxy(C1-C4)alkylamino, imidazolinium and ammonium groups. ### Claim 19 (depends on 17) The dye composition according to claim 17, wherein the halogens are chosen from chlorine. ### Claim 20 (depends on 16) The dye composition according to claim 16, wherein the double bases are chosen from the compounds of formula (II): wherein, Z1 and Z2, which may be identical or different, are chosen from hydroxyl and —NH2 groups that may be substituted with a C1-C4 alkyl group or with a linking element Y; the linking element Y is chosen from linear and branched alkylene chains comprising from 1 to 14 carbon atoms, which may be interrupted by or terminated by at least one nitrogenous group and/or at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl and C1-C6 alkoxy groups; R5 and R6, which may be identical or different, are chosen from hydrogen, halogens, a C1-C4 alkyl group, a C1-C4 monohydroxyalkyl group, a C2-C4 polyhydroxyalkyl group, a C1-C4 aminoalkyl group, and a linking element Y; R7, R8, R9, R10, R11 and R12, which may be identical or different, are chosen from hydrogen, a linking element Y, and C1-C4 alkyl groups; with the proviso that the compounds of formula (II) comprise only one linking element Y per double base. ### Claim 21 (depends on 20) The dye composition according to claim 20, wherein the at least one hetero atom is chosen from oxygen, sulfur and nitrogen atoms. ### Claim 22 (depends on 20) The dye composition according to claim 20, wherein the nitrogenous groups are chosen from amino, mono(C1-C4)alkylamino, di(C1-C4)alkylamino, tri(C1-C4)alkylamino, monohydroxy(C1-C4)alkylamino, imidazolinium and ammonium groups. ### Claim 23 (depends on 16) The dye composition according to claim 16, wherein the para-aminophenols are chosen from the compounds of formula (III): wherein: R13 is chosen from hydrogen, halogens, C1-C4 alkyl, C1-C4 monohydroxyalkyl, (C1-C4)alkoxy(C1-C4)alkyl, C1-C4 aminoalkyl and hydroxy(C1-C4)alkylamino(C1-C4)alkyl groups, R14 is chosen from hydrogen, halogens, C1-C4 alkyl, C1-C4 monohydroxyalkyl, C2-C4 polyhydroxyalkyl, C1-C4 aminoalkyl, C1-C4 cyanoalkyl and (C1-C4)alkoxy-(C1-C4)alkyl groups. ### Claim 24 (depends on 23) The dye composition according to claim 23, wherein the halogens are chosen from fluorine. ### Claim 25 (depends on 16) The dye composition according to claim 16, wherein the heterocyclic bases are chosen from pyridine derivatives, pyrimidine derivatives, and pyrazole derivatives. ### Claim 26 (depends on 25) The dye composition according to claim 25, wherein the pyrimidine derivatives are chosen from pyrazolopyrimidines. ### Claim 27 (depends on 15) The dye composition according to claim 15, wherein the at least one oxidation base is present in the composition in an amount ranging from 0.0005% to 12% by weight, relative to the total weight of the dye composition. ### Claim 28 (depends on 14) The dye composition according to claim 14, wherein the at least one coupler is chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, and the acid addition salts thereof. ### Claim 29 (depends on 14) The dye composition according to claim 14, wherein the at least one coupler is present in the composition in an amount ranging from 0.0001% to 10% by weight, relative to the total weight of the composition. ### Claim 30 (depends on 16) The dye composition according to claim 16, wherein the acid addition salts of the at least one oxidation base are chosen from hydrochlorides, hydrobromides, sulfates, tartrates, lactates and acetates. ### Claim 31 (depends on 28) The dye composition according to claim 28, wherein the acid addition salts of the at least one coupler are chosen from hydrochlorides, hydrobromides, sulfates, tartrates, lactates and acetates. ### Claim 32 (depends on 1) The dye composition according to claim 1, further comprising at least one direct dye. ### Claim 33 (depends on 1) The dye composition according to claim 1, further comprising at least one adjuvants chosen from anionic, cationic, amphoteric, zwitterionic and nonionic surfactants, provided that the nonionic surfactants are those other than nonionic surfactants with an HLB value of less than or equal to 10; thickeners; fragrances; sequestering agents; UV-screening agents; waxes; silicones chosen from volatile and non-volatile, cyclic, linear and branched, organomodified and non-organomodified silicones; preserving agents; ceramides; pseudoceramides; vegetable, mineral and synthetic oils; vitamins and provitamins; opacifiers; reducing agents; and antioxidants. ### Claim 34 (depends on 1) The dye composition according to claim 1, wherein the cosmetically acceptable aqueous medium comprises water, and may optionally comprise cosmetically acceptable organic solvents. ### Claim 35 A process for preparing a dye composition comprising: a) preparing at least one mesomorphic phase by mixing at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of the dye composition, with water and optionally with at least one fatty alcohol, the at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2), and b) adding at least one oxidation dye to the at least one mesomorphic phase, wherein ammonia is added in step a), step b), or both. ### Claim 36 (depends on 35) The process according to claim 35, wherein the at least one non ionic surfactant of step a) has an HLB value ranging from 1 to 5. ### Claim 37 A ready-to-use composition for the oxidation dyeing of keratin fibers, comprising, in a medium suitable for dyeing, at least one dye composition (A) comprising at least one oxidation dye, ammonia, and at least one mesomorphic phase present in composition (A) in an amount greater than or equal to 10% by weight, relative to the weight of composition (A), the at least one mesomorphic phase comprising at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of composition (A), and at least one composition (B) comprising at least one oxidizing agent, the at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2). ### Claim 38 (depends on 37) The ready-to-use composition according to claim 37, wherein the mesomorphic phase is present in the ready-to-use composition in an amount greater than or equal to 5% by weight, relative to the total weight of the ready-to-use composition. ### Claim 39 (depends on 38) The ready-to-use composition according to claim 38, wherein mesomorphic phase is present in the ready-to-use composition in an amount ranging from 10% to 30% by weight, relative to the total weight of the ready-to-use composition. ### Claim 40 (depends on 37) The ready-to-use composition according to claim 37, wherein the at least one oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates and ferricyanides, persalts, and redox enzymes, optionally in the presence of the respective donor or co-factor thereof. ### Claim 41 (depends on 40) The ready-to-use composition according to claim 40, wherein the redox enzymes are chosen from laccases, peroxidases, and 2-electron oxidoreductases. ### Claim 42 (depends on 40) The ready-to-use composition according to claim 40, wherein the at least one oxidizing agent is hydrogen peroxide. ### Claim 43 (depends on 41) The ready-to-use composition according to claim 41, wherein the at least one oxidizing agent is an aqueous hydrogen peroxide solution with a titre ranging from 1 to 40 volumes. ### Claim 44 (depends on 37) The ready-to-use composition according to claim 37, wherein the ready-to-use composition has a pH ranging approximately from 4 to 12. ### Claim 45 An oxidizing composition, comprising at least one oxidizing agent chosen from hydrogen peroxide, urea peroxide, alkali metal bromates and ferricyanides, persalts, and redox enzymes, optionally in the presence of the respective donor or co-factor thereof, and at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2), wherein the at least one mesomorphic phase is present in the oxidizing composition in an amount greater than or equal to 10% by weight, relative to the total weight of the oxidizing composition, the at least one mesomorphic phase comprising at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of the dye composition. ### Claim 46 A method for dyeing keratin fibers, comprising applying to wet or dry keratin fibers, a ready-to-use composition comprising, in a medium suitable for dyeing, at least one composition (A) comprising at least one oxidation dye, ammonia, and at least one mesomorphic phase present in composition (A) in an amount greater than or equal to 10% by weight, relative to the total weight of composition (A), the at least one mesomorphic phase comprising at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of composition (A), the at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2), and at least one composition (B) comprising at least one oxidizing agent, wherein the ready-to-use composition is prepared extemporaneously at the time of use, and wherein the ready-to-use composition is left on the keratin fibers to act for a leave-in time ranging from 1 to 60 minutes approximately, rinsing the fibers and then optionally washing them with shampoo, then rinsing them again and drying them. ### Claim 47 (depends on 45) The method according to claim 45, wherein the leave-in time ranges approximately from 10 to 45 minutes. ### Claim 48 A multi-compartment kit for the oxidation dyeing of keratin fibers, comprising at least two compartments, wherein at least one compartment contains at least one dye composition comprising at least one oxidation dye, ammonia, and at least one mesomorphic phase present in the dye composition in an amount greater than or equal to 10% by weight, relative to the total weight of the dye composition, the at least one mesomorphic phase comprising at least one nonionic surfactant with an HLB value of less than or equal to 10 in an amount ranging from 10% to 20% by weight, relative to the weight of the dye composition, the at least one mesomorphic phase chosen from inverse hexagonal phases (H2), lamellar phases (Lβ) and inverse cubic phases (I2 and V2), and at least one other compartment contains a composition comprising at least one oxidizing agent.