Back to results
US 7,892,294 B2Granted
Method for dyeing keratin fibers using at least one compound of azomethine type comprising a pyrazolopyridine unit
AssigneeL'oreal
InventorsAziz Fadli, Stéphane Blais
Life of this patent
Estimating the term…
Abstract
Provided herein is a method for dyeing keratin fibers, comprising applying to the keratin fibers, at least one composition comprising at least one compound chosen from compounds of leuco type of formula (I), dyes of azomethine type containing a pyrazolopyridine unit of formula (II) corresponding to the compounds of formula (I), mesomeric forms, isomers and tautomers thereof, and also acid-addition salts thereof and solvates thereof:
Claims15
A method for dyeing keratin fibers comprising
- applying to the keratin fibers at least one composition comprising at least one compound chosen from leuco form compounds of formula (I), dyes of azomethine type comprising a pyrazolopyridine unit of formula (II), mesomeric forms, isomers and tautomers thereof, acid-addition salts thereof, and solvates thereof:
- in which:
- Z1 represents an oxygen atom, or a group NR6,
- when Z1 represents NR6 then R1 and R6 can form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered heterocycle,
- Z1 can also represent a divalent radical S, SO or SO2 when R1 is a methyl,
- R1 and R6 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C10 alkyl radical, wherein the substituent can be a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle, or
- a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle,
- R2, R3, R4 and R5 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C4 alkyl,
- a group chosen from NH2, NHR10, NR11R12, OH and OR9, wherein
- R9 and R10 independently represent a linear or branched, optionally substituted C1-C6 alkyl,
- R11 and R12, which may be identical or different, represent an optionally substituted linear or branched C1-C6 alkyl, or R11 and R12, together with the nitrogen atom to which they are attached, form a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally comprising at least one other radical chosen from N, O, S, SO2 and CO, wherein the heterocycle is optionally substituted, or
- two adjacent R2, R3, R4 and R5, together with the two carbon atoms to which they are attached, form a saturated or unsaturated, optionally substituted (hetero)cycle;
- n is an integer ranging from 0 to 3;
- U represents CR or N;
- R represents
- a hydrogen atom,
- a C1-C4 alkyl optionally substituted with a hydroxyl;
- a C1-C4 alkoxy optionally substituted with a hydroxyl;
- or
- a (di)(C1-C4)alkylamino in which the alkyl part is optionally substituted with a hydroxyl;
- X represents:
- a hydroxyl;
- or
- a group NR′1R″1, wherein R′1 and R″1 are independently chosen from a hydrogen atom;
- a C1-C6 alkyl radical optionally substituted with at least one radical chosen from a hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- a phenyloptionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy;
- when R′1 and R″1 are other than a hydrogen, R′1 and R″1 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atoms, and optionally substituted with at least one radical chosen from halogen atoms, aminos, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, carboxamido, (C1-C2)alkoxy, and C1-C4 alkyl radicals, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- when X represents a group NHR′1 and when U represents a group CR in which R denotes an alkoxy, then X and U together can form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- V represents
- an oxygen atom;
- or
- a group NR′1, wherein R′1 is chosen from a hydrogen atom;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino and (di)(C1-C2)alkylamino;
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino and (C1-C2)alkoxy;
- when V represents a group NR′1 and when U represents a group CR in which R denotes an alkoxy, then V and U may form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- Y, which may be identical or different, represent:
- a hydroxyl;
- a C1-C4 alkyl;
- a C1-C4 hydroxyalkyl;
- a halogen atom;
- an oxygen atom substituted with a radical chosen from a C1-C4 alkyl, an aryl and a heteroaryl, these radicals optionally substituted with at least one hydroxyl;
- or
- a group NR′2R′3;
- R′2 and R′3, which may be identical or different, are chosen from
- a hydrogen atom;
- a C1-C4 alkylcarbonyl optionally substituted with a quaternary ammonium group, or with a cationic or non-cationic nitrogenous heterocycle optionally substituted with at least one C1-C4 alkyl;
- an aminocarbonyl;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- and
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy radicals;
- or
- R′2 and R′3 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated, 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atom, and optionally substituted with at least one radical chosen from halogen atoms and amino, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, (di)alkylcarboxamido, (C1-C2)alkoxy, and C1-C4 alkyl, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- or
- two radicals Y borne by two adjacent carbon atoms form, together with the carbon atoms to which they are attached, a saturated or unsaturated, aromatic or non-aromatic, 5- to 6-membered cyclic or heterocyclic group optionally substituted with at least one C1-C4 alkyl.
55 more elements
A composition for dyeing keratin fibers, comprising, in a suitable dyeing medium, at least one compound chosen from leuco form compounds of formula (I), dyes of azomethine type comprising a pyrazolopyridine unit of formula (II), mesomeric forms, isomers and tautomers thereof, acid-addition salts thereof, and solvates thereof,
- in which:
- Z1 represents an oxygen atom, or a group NR6,
- when Z1 represents NR6 then R1 and R6 can form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered heterocycle,
- Z1 can also represent a divalent radical S, SO or SO2 when R1 is a methyl,
- R1 and R6 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C10 alkyl radical, wherein the substituent can be a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle, or
- a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle,
- R2, R3, R4 and R5 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C4 alkyl,
- a group chosen from NH2, NHR10, NR11R12, OH and OR9, wherein
- R9 and R10 independently represent a linear or branched, optionally substituted C1-C6 alkyl,
- R11 and R12, which may be identical or different, represent an optionally substituted linear or branched C1-C6 alkyl, or R11 and R12, together with the nitrogen atom to which they are attached, form a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally comprising at least one other radical chosen from N, O, S, SO2 and CO, wherein the heterocycle is optionally substituted, or
- two adjacent R2, R3, R4 and R5, together with the two carbon atoms to which they are attached, form a saturated or unsaturated, optionally substituted (hetero)cycle;
- n is an integer ranging from 0 to 3;
- U represents CR or N;
- R represents
- a hydrogen atom,
- a C1-C4 alkyl optionally substituted with a hydroxyl;
- a C1-C4 alkoxy optionally substituted with a hydroxyl;
- or
- a (di)(C1-C4)alkylamino in which the alkyl part is optionally substituted with a hydroxyl;
- X represents:
- a hydroxyl;
- or
- a group NR′1R″1, wherein R′1 and R″1 are independently chosen from a hydrogen atom;
- a C1-C6 alkyl radical optionally substituted with at least one radical chosen from a hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- a phenyloptionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy;
- when R′1 and R″1 are other than a hydrogen, R′1 and R″1 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atoms, and optionally substituted with at least one radical chosen from halogen atoms, aminos, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, carboxamido, (C1-C2)alkoxy, and C1-C4 alkyl radicals, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- when X represents a group NHR′1 and when U represents a group CR in which R denotes an alkoxy, then X and U together can form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- V represents
- an oxygen atom;
- or
- a group NR′1, wherein R′1 is chosen from a hydrogen atom;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino and (di)(C1-C2)alkylamino;
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino and (C1-C2)alkoxy;
- when V represents a group NR′1 and when U represents a group CR in which R denotes an alkoxy, then V and U may form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- Y, which may be identical or different, represent:
- a hydroxyl;
- a C1-C4 alkyl;
- a C1-C4 hydroxyalkyl;
- a halogen atom;
- an oxygen atom substituted with a radical chosen from a C1-C4 alkyl, an aryl and a heteroaryl, these radicals optionally substituted with at least one hydroxyl;
- or
- a group NR′2R′3;
- R′2 and R′3, which may be identical or different, are chosen from
- a hydrogen atom;
- a C1-C4 alkylcarbonyl optionally substituted with a quaternary ammonium group, or with a cationic or non-cationic nitrogenous heterocycle optionally substituted with at least one C1-C4 alkyl;
- an aminocarbonyl;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- and
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy radicals;
- or
- R′2 and R′3 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated, 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atom, and optionally substituted with at least one radical chosen from halogen atoms and amino, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, (di)alkylcarboxamido, (C1-C2)alkoxy, and C1-C4 alkyl, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- or
- two radicals Y borne by two adjacent carbon atoms form, together with the carbon atoms to which they are attached, a saturated or unsaturated, aromatic or non-aromatic, 5- to 6-membered cyclic or heterocyclic group optionally substituted with at least one C1-C4 alkyl,
- provided that when X is hydroxyl or V is oxygen, at least one Y is hydroxyl or a group NR′2R′3,
- with the exception of the following compound:
- mesomeric forms thereof, isomers and tautomers thereof, acid-addition salts thereof, and solvates thereof.
57 more elements
At least one compound chosen from leuco form compounds of formula (I) and dyes of azomethine type comprising a pyrazolopyridine unit of formula (II), mesomeric forms, isomers and tautomers thereof, acid-addition salts thereof and solvates thereof:
- in which:
- Z1 represents an oxygen atom, or a group NR6,
- when Z1 represents NR6 then R1 and R6 can form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered heterocycle,
- Z1 can also represent a divalent radical S, SO or SO2 when R1 is a methyl,
- R1 and R6 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C10 alkyl radical, wherein the substituent can be a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle, or
- a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle,
- R2, R3, R4 and R5 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C4 alkyl,
- a group chosen from NH2, NHR10, NR11R12, OH and OR9, wherein
- R9 and R10 independently represent a linear or branched, optionally substituted C1-C6 alkyl,
- R11 and R12, which may be identical or different, represent an optionally substituted linear or branched C1-C6 alkyl, or R11 and R12, together with the nitrogen atom to which they are attached, form a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally comprising at least one other radical chosen from N, O, S, SO2 and CO, wherein the heterocycle is optionally substituted, or
- two adjacent R2, R3, R4 and R5, together with the two carbon atoms to which they are attached, form a saturated or unsaturated, optionally substituted (hetero)cycle;
- n is an integer ranging from 0 to 3;
- U represents CR or N;
- R represents
- a hydrogen atom,
- a C1-C4 alkyl optionally substituted with a hydroxyl;
- a C1-C4 alkoxy optionally substituted with a hydroxyl;
- or
- a (di)(C1-C4)alkylamino in which the alkyl part is optionally substituted with a hydroxyl;
- X represents:
- a hydroxyl;
- or
- a group NR′1R″1, wherein R′1 and R″1 are independently chosen from a hydrogen atom;
- a C1-C6 alkyl radical optionally substituted with at least one radical chosen from a hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- a phenyloptionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy;
- when R′1 and R″1 are other than a hydrogen, R′1 and R″1 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atoms, and optionally substituted with at least one radical chosen from halogen atoms, aminos, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, carboxamido, (C1-C2)alkoxy, and C1-C4 alkyl radicals, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- when X represents a group NHR′1 and when U represents a group CR in which R denotes an alkoxy, then X and U together can form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- V represents
- an oxygen atom;
- or
- a group NR′1, wherein R′1 is chosen from a hydrogen atom;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino and (di)(C1-C2)alkylamino;
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino and (C1-C2)alkoxy;
- when V represents a group NR′1 and when U represents a group CR in which R denotes an alkoxy, then V and U may form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- Y, which may be identical or different, represent:
- a hydroxyl;
- a C1-C4 alkyl;
- a C1-C4 hydroxyalkyl;
- a halogen atom;
- an oxygen atom substituted with a radical chosen from a C1-C4 alkyl, an aryl and a heteroaryl, these radicals optionally substituted with at least one hydroxyl;
- or
- a group NR′2R′3;
- R′2 and R′3, which may be identical or different, are chosen from
- a hydrogen atom;
- a C1-C4 alkylcarbonyl optionally substituted with a quaternary ammonium group, or with a cationic or non-cationic nitrogenous heterocycle optionally substituted with at least one C1-C4 alkyl;
- an aminocarbonyl;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- and
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy radicals;
- or
- R′2 and R′3 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated, 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atom, and optionally substituted with at least one radical chosen from halogen atoms and amino, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, (di)alkylcarboxamido, (C1-C2)alkoxy, and C1-C4 alkyl, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- or
- two radicals Y borne by two adjacent carbon atoms form, together with the carbon atoms to which they are attached, a saturated or unsaturated, aromatic or non-aromatic, 5- to 6-membered cyclic or heterocyclic group optionally substituted with at least one C1-C4 alkyl,
- provided that when X is hydroxyl or V is oxygen, at least one Y is hydroxyl or a group NR′2R′3,
- with the exception of the following compound:
- and mesomeric forms thereof, acid-addition salts thereof and solvates thereof.
57 more elements
A multi-compartment dyeing kit, comprising at least one first compartment which comprises at least one compound of formula (I), and at least one second compartment which comprises at least one oxidizing agent and optionally at least one compound of formula (II), and at least one alkaline agent;
- wherein the at least one compound of formula (I), and the at least one compound of formula (II) are chosen from
- in which:
- Z1 represents an oxygen atom, or a group NR6,
- when Z1 represents NR6 then R1 and R6 can form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered heterocycle,
- Z1 can also represent a divalent radical S, SO or SO2 when R1 is a methyl,
- R1 and R6 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C10 alkyl radical, wherein the substituent can be a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle, or
- a saturated, unsaturated or aromatic, optionally substituted 5- to 8-membered (hetero)cycle,
- R2, R3, R4 and R5 independently represent:
- a hydrogen atom,
- an optionally substituted C1-C4 alkyl,
- a group chosen from NH2, NHR10, NR11R12, OH and OR9, wherein
- R9 and R10 independently represent a linear or branched, optionally substituted C1-C6 alkyl,
- R11 and R12, which may be identical or different, represent an optionally substituted linear or branched C1-C6 alkyl, or R11 and R12, together with the nitrogen atom to which they are attached, form a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally comprising at least one other radical chosen from N, O, S, SO2 and CO, wherein the heterocycle is optionally substituted, or
- two adjacent R2, R3, R4 and R5, together with the two carbon atoms to which they are attached, form a saturated or unsaturated, optionally substituted (hetero)cycle;
- n is an integer ranging from 0 to 3;
- U represents CR or N;
- R represents
- a hydrogen atom,
- a C1-C4 alkyl optionally substituted with a hydroxyl;
- a C1-C4 alkoxy optionally substituted with a hydroxyl;
- or
- a (di)(C1-C4)alkylamino in which the alkyl part is optionally substituted with a hydroxyl;
- X represents:
- a hydroxyl;
- or
- a group NR′1R″1, wherein R′1 and R″1 are independently chosen from a hydrogen atom;
- a C1-C6 alkyl radical optionally substituted with at least one radical chosen from a hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- a phenyloptionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy;
- when R′1 and R″1 are other than a hydrogen, R′1 and R″1 can form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atoms, and optionally substituted with at least one radical chosen from halogen atoms, aminos, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, carboxamido, (C1-C2)alkoxy, and C1-C4 alkyl radicals, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- when X represents a group NHR′1 and when U represents a group CR in which R denotes an alkoxy, then X and U together can form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- V represents
- oxygen atom;
- or
- group NR′1, wherein R′1 is chosen from a hydrogen atom;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino and (di)(C1-C2)alkylamino;
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino and (C1-C2)alkoxy;
- when V represents a group NR′1 and when U represents a group CR in which R denotes an alkoxy, then V and U may form a 6-membered ring of morpholine type, optionally substituted with at least one C1-C4 alkyl;
- Y, which may be identical or different, represent:
- a hydroxyl;
- a C1-C4 alkyl;
- a C1-C4 hydroxyalkyl;
- a halogen atom;
- an oxygen atom substituted with a radical chosen from a C1-C4 alkyl, an aryl and a heteroaryl, these radicals optionally substituted with at least one hydroxyl;
- or
- a group NR′2R′3;
- R′2 and R′3, which may be identical or different, are chosen from
- a hydrogen atom;
- a C1-C4 alkylcarbonyl optionally substituted with a quaternary ammonium group, or with a cationic or non-cationic nitrogenous heterocycle optionally substituted with at least one C1-C4 alkyl;
- an aminocarbonyl;
- a C1-C6 alkyl optionally substituted with at least one radical chosen from hydroxyl, (C1-C2)alkoxy, amino, and (di)(C1-C2)alkylamino;
- and
- a phenyl radical optionally substituted with at least one radical chosen from hydroxyl, amino, and (C1-C2)alkoxy radicals;
- or
- R′2 and R′3 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated, 5- to 7-membered heterocycle optionally comprising at least one additional heteroatom chosen from oxygen and nitrogen atom, and optionally substituted with at least one radical chosen from halogen atoms and amino, (di)(C1-C4)alkylamino, hydroxyl, carboxyl, (di)alkylcarboxamido, (C1-C2)alkoxy, and C1-C4 alkyl, optionally substituted with at least one radical chosen from hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, and sulfonyl;
- or
- two radicals Y borne by two adjacent carbon atoms form, together with the carbon atoms to which they are attached, a saturated or unsaturated, aromatic or non-aromatic, 5- to 6-membered cyclic or heterocyclic group optionally substituted with at least one C1-C4 alkyl.
55 more elements
Dependencies are inferred from the claim text.