Use of tetra-azapentamethine compounds as direct dyeing agents and novel tetra-azapentamethine compounds
AssigneeL'oreal
InventorsHerve Burgaud, Herve David, Rui Pereira, Beatrice Belcour-Castro
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Abstract
The invention concerns the use as direct dyeing agent of at least one tetra-azapentamethine compound, a dyeing composition comprising at least such a compound, as well as a method for dyeing keratinous fibers, in particular human keratinous fibers and more particularly hair, which consists in applying at least one composition comprising such a compound. The composition also concerns tetra-azapentamethine compounds of formula (I). The invention further concerns a method for bleaching such compounds, as well as bleaching keratinous fibers previously dyed therewith.
Claims29
A tetraazapentamethine compound of formula (I′):
- wherein:
- W′1 represents a cationic heteroaromatic radical of formula (II′) or (III′):
- W′2 represents a heteroaromatic radical of formula (IV′) or (V′):
- wherein:
- Z′0 represents a radical CR′2, a nitrogen atom or a radical NR′21,
- Z′1 represents an oxygen atom or a radical NR′9,
- Z′2 represents a nitrogen atom or a radical CR′10,
- Z′3 represents a nitrogen atom or a radical CR′11,
- Z′4 represents a nitrogen atom or a radical CR′12,
- Z′5 represents a nitrogen atom or a radical CR′13,
- Z′6 represents a nitrogen atom or a radical CR′14,
- Z′7 represents an oxygen atom, or a radical NR′15,
- Z′8 represents a nitrogen atom or a radical CR′16,
- Z′9 represents a nitrogen atom or a radical CR′17,
- Z′10 represents a nitrogen atom or a radical CR′18,
- Z′11 represents a nitrogen atom or a radical CR′19,
- Z′12 represents a nitrogen atom or a radical CR′20,
- Z′13 represents a radical CR′6, a nitrogen atom or a radical NR′22,
- wherein each of the rings of formulae (II′), (III′), (IV′) and (V′) comprise not more than three nitrogen atoms and two of the three nitrogen atoms may be contiguous,
- the bond a of the 5-membered cationic heteroaromatic radical of formula (II′) being linked to the nitrogen atom N1 of formula (I′),
- the bond b of the 6-membered cationic heteroaromatic radical of formula (III′) being linked to the nitrogen atom N1 of formula (I′),
- the double bond a′ of the 5-membered heteroaromatic radical of formula (IV′) being linked to the nitrogen atom N2 of formula (I′),
- the double bond b′ of the 6-membered heteroaromatic radical of formula (V′) being linked to the nitrogen atom N2 of formula (I′),
- the bond b, linking the cationic heteroaromatic radical of formula (III′) to the nitrogen atom N1 of formula (I′), being in an ortho or para position relative to the nitrogen atom bearing the radical R′4 when Z′5 represents a radical CR′13;
- the bond b being in an ortho position relative to the nitrogen atom bearing the radical R′4 when Z′5 represents a nitrogen atom,
- the bond b′, linking the heteroaromatic radical of formula (V′) to the nitrogen atom N2 of formula (I′), being in an ortho or para position relative to the nitrogen atom bearing the radical R′7 when Z′11 represents a radical CR′19;
- the bond b′ being in an ortho position relative to the nitrogen atom bearing the radical R′7 when Z′11 represents a nitrogen atom,
- R′2, R′6, R′10 and R′16 represent, independently of each other, a hydrogen atom;
- a linear or branched C1-C4 alkyl radical, which is unsubstituted or substituted with one to three radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl and sulfonic radicals;
- a phenyl radical, which is unsubstituted or substituted with one or two radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, amino and C1-C2 (di)alkylamino;
- a carboxyl radical;
- a sulfonylamino radical,
- R′1, R′4, R′5, R′7, R′9, R′15 and R′22 represent, independently of each other, a linear or branched C1-C8 alkyl radical, which is unsubstituted or substituted with one to three radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl and sulfonic radicals;
- R′0, R′3, R′8, R′11, R′12, R′13, R′14, R′17, R′18, R′19 and R′20 represent, independently of each other, a hydrogen atom, a linear or branched C1-C16 hydrocarbon-based chain, this chain possibly being saturated or unsaturated with one to three unsaturations, this chain being unsubstituted or substituted with one to three radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, sulfonic, sulfonylamino and C2-C4 (poly)-hydroxyalkylamino radicals or a halogen atom;
- a phenyl radical, which is unsubstituted or substituted with one to three radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, sulfonic, sulfonylamino and C2-C4 (poly)-hydroxyalkylamino radicals or a halogen atom;
- a heteroaryl radical chosen from pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, triazolyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl and pyridazinyl radicals;
- in addition, this hydrocarbon-based chain may be interrupted with one or two oxygen, nitrogen, sulphur atoms or with an SO2 radical,
- R′2 with R′10, R′11 with R′12, R′6 with R′16, and R′17 with R′18, being able to form independently of each other, a 5- or 6-membered carbon-based aromatic ring, which is unsubstituted or substituted with one or two hydroxyl, amino, (di)(C1-C2)alkylamino, C1-C2 alkoxy or C2-C4 (poly)hydroxyalkylamino radicals, subject to W′1 and W′2 not representing, simultaneously, the same bicyclic system,
- wherein R′0, R′3, R′8, R′11, R′12, R′14, R′17, R′18, R′19 and R′20 do not comprise a peroxide bond, or diazo or nitroso radicals,
- X is an organic or inorganic anion.
A Composition for dyeing keratin fibers comprising, in a medium that is suitable for dyeing, at least one compound selected from the group consisting of:
- 2-[5-(N-methyl-2-pyridinylidene)-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-methyl-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-ethyl-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-isopropyl-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-phenyl-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-methylpyridinium chloride
- 2-[5-(N-methyl-2-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-methyl-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-ethyl-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-isopropyl-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-phenyl-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(4-pyrrolidino-N-methyl-2-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-4-pyrrolidino-N-methylpyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-1-formazano]-N-hydroxyethylpyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-methyl-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-ethyl-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-phenyl-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-isopropyl-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-hydroxyethyl-2-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-methyl-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-ethyl-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-phenyl-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-isopropyl-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-carboxyethyl-pyridinium chloride
- 2-[5-(N-carboxyethyl-2-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-carboxyethyl-pyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-methyl-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-ethyl-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-isopropyl-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-phenyl-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-methyl-4-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-methylpyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-1-formazano]-N-hydroxyethylpyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-methyl-1-formazano]-N-hydroxyethylpyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-ethyl-1-formazano]-N-hydroxyethylpyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-phenyl-1-formazano]-N-hydroxyethylpyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-isopropyl-1-formazano]-N-hydroxyethyl pyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-hydroxyethyl pyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-hydroxyethyl-pyridinium chloride
- 4-[5-(N-hydroxyethyl-4-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-hydroxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-1-formazano]-N carboxyethyl-pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-methyl-1-formazano]-N-carboxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-ethyl-1-formazano]-N-carboxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-phenyl-1-formazano]-N-carboxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-isopropyl-1-formazano]-N-carboxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-(4′-methoxyphenyl)-1-formazano]-N-carboxyethyl pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-(4′-hydroxyphenyl)-1-formazano]-N-carboxyethyl-pyridinium chloride
- 4-[5-(N-carboxyethyl-4-pyridinylidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-N-carboxyethyl pyridinium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-1-formazano]-1,3-dimethylimidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-methyl-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-ethyl-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-isopropyl-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-phenyl-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-(4′-methoxyphenyl)-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-(4′-hydroxyphenyl)-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dimethyl-2-imidazolidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-1,3-dimethyl imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-methyl-1-formazano]-1,3-dihydroxyethylimidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-ethyl-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-phenyl-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-isopropyl-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-(4′-methoxyphenyl)-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-(4′-hydroxyphenyl)-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dihydroxyethyl-2-imidazolidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-1,3-dihydroxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-methyl-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-ethyl-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-phenyl-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-isopropyl-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-(4′-methoxyphenyl)-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-(4′-hydroxyphenyl)-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride and
- 2-[5-(1,3-dicarboxyethyl-2-imidazolidene)-3-(4′-N,N-dimethylaminophenyl)-1-formazano]-1,3-dicarboxyethyl-imidazolium chloride.
Dependencies are inferred from the claim text.