(Dis)symmetric azomethine-type direct dye comprising at least one pyrazolopyridine unit, process for dyeing keratin fibers using this dye
AssigneeL'oreal
InventorsStéphane Sabelle, Stéphane Blais, Aziz Fadli
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Abstract
The subject of the present invention is symmetric or dissymetric azomethine direct dyes comprising at least one pyrazolopyridine unit of formula (I), a composition comprising said dyes, a process for treating keratin fibers using said dyes, a process for preparing these compounds, synthesis intermediates and a kit. In which formula (I) X, Y1, Y2, Z1, and R1 to R5 are as defined in the description.
Claims20
A compound chosen from azomethine dyes comprising at least one pyrazolopyridine unit of formula (I), a leuco form, an optical isomer, a geometrical isomer, a tautomers thereof, an organic or mineral acid or base addition salt thereof, a solvate thereof, or a hydrate thereof:
- in which formula (I):
- Y1 and Y2, which may be identical or different, represent a nitrogen atom or a group C(R) with R representing a hydrogen atom or a (C1-C6)alkyl group;
- Z1 represents an oxygen atom or a group —N(R6)—;
- when Z1 represents —N(R6)—, then R1 and R6 optionally form, together with the nitrogen atom to which they are attached, an optionally substituted, optionally cationic, 5- to 8-membered, saturated, unsaturated or aromatic heterocycle;
- R1 and R6, which may be identical or different, represent:
- a hydrogen atom;
- a C1-C10 alkyl radical optionally interrupted with one or more non-adjacent heteroatoms, and/or optionally substituted;
- an optionally substituted, 5- to 8-membered, cationic or non-cationic, saturated, unsaturated or aromatic (hetero)cyclic radical;
- R2, R3, R4, and R5, which may be identical or different, each independently represent:
- a hydrogen atom;
- an optionally substituted C1-C6 alkyl radical;
- a group chosen from —NH2, —N(H)R10, —N(R11)R12, OH and/or —OR9, with R9 and R10 representing an optionally substituted, linear or branched C1-C6 alkyl, R11 and R12, which may be identical or different, representing an optionally substituted, linear or branched C1-C6 alkyl, wherein R11 and R12 optionally form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally containing one or more other heteroatoms or groups chosen from N, O, S, S(O)2 and C(O), the heterocycle being optionally substituted;
- a halide and/or
- R2, R3, R4, and R5 form, in pairs, with adjacent radicals, an optionally substituted, saturated or unsaturated (hetero)cycle;
- X represents an optionally substituted aryl or optionally substituted heteroaryl radical;
- wherein
- when the compounds of formula (I) are cationic, then their electro-neutrality is provided by one or more cosmetically acceptable anions which may be identical or different;
- and
- when Y1 represents NH and Y2 represents a CH group, then X represents a group other than a pyrazolo[1,5-a]pyridin-3-yl group which is optionally substituted.
A method for dyeing keratin fibers, comprising applying to keratin fibers a compound chosen from azomethine dyes comprising at least one pyrazolopyridine unit of formulae (I), a leuco form, an optical isomer, a geometrical isomer, a tautomers thereof, an organic or mineral acid or base addition salt thereof, a solvate thereof, or a hydrate thereof:
- in which formula (I):
- Y1 and Y2, which may be identical or different, represent a nitrogen atom or a group C(R) with R representing a hydrogen atom or a (C1-C6)alkyl group;
- Z1 represents an oxygen atom or a group —N(R6)—;
- when Z1 represents —N(R6)—, then R1 and R6 optionally form, together with the nitrogen atom to which they are attached, an optionally substituted, optionally cationic, 5- to 8-membered, saturated, unsaturated or aromatic heterocycle;
- R1 and R6, which may be identical or different, represent:
- a hydrogen atom;
- a C1-C10 alkyl radical optionally interrupted with one or more non-adjacent heteroatoms, and/or optionally substituted;
- an optionally substituted, 5- to 8-membered, cationic or non-cationic, saturated, unsaturated or aromatic (hetero)cyclic radical;
- R2, R3, R4, and R5, which may be identical or different, each independently represent:
- a hydrogen atom;
- an optionally substituted C1-C6 alkyl radical;
- a group chosen from —NH2, —N(H)R10, —N(R11)R12, OH and/or —OR9, with R9 and R10 representing an optionally substituted, linear or branched C1-C6 alkyl, R11 and R12, which may be identical or different, representing an optionally substituted, linear or branched C1-C6 alkyl, wherein R11 and R12 optionally form, together with the nitrogen atom to which they are attached, a saturated, unsaturated or aromatic 5- to 8-membered heterocycle optionally containing one or more other heteroatoms or groups chosen from N, O, S, S(O)2 and C(O), the heterocycle being optionally substituted;
- a halide and/or
- R2, R3, R4, and R5 form, in pairs, with adjacent radicals, an optionally substituted, saturated or unsaturated (hetero)cycle;
- X represents an optionally substituted aryl or optionally substituted heteroaryl radical;
- wherein
- when the compounds of formula (I) are cationic, then their electro-neutrality is provided by one or more cosmetically acceptable anions which may be identical or different;
- and
- when Y1 represents NH and Y2 represents a CH group, then X represents a group other than a pyrazolo[1,5-a]pyridin-3-yl group which is optionally substituted.
Dependencies are inferred from the claim text.