Composition for dyeing the hair, comprising a heterocyclic oxidation base and a 2-amino-5-ethylphenol coupler
Composition for dyeing the hair, comprising a heterocyclic oxidation base and a 2-amino-5-ethylphenol coupler The present invention relates to a composition for dyeing keratin fibres, comprising a particular heterocyclic oxidation base and a 2-amino-5-ethylphenol coupler. The invention also relates to a process for dyeing keratin fibres using this composition. Finally, the invention relates to the use of such a composition for dyeing keratin fibres, and in particular the hair.
1. A composition for dyeing keratin fibers, comprising:
(A) at least one 2-amino-5-ethylphenol coupler, an addition salt thereof, or a solvate thereof,
(B) at least one pyrazole heterocyclic oxidation base chosen from:
A1) pyrazolopyridines according to formula (I) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R 1 , R 2 , R 3 , R 4 , and R 5 , which may be identical or different, are chosen from a hydrogen atom; a halogen atom; a —NHSO 3 H radical; a hydroxyl radical; a (C 1 -C 4 )alkyl radical; a (C 1 -C 4 )alkoxy radical; a (C 1 -C 4 )alkylthio radical; mono(C 1 -C 4 )alkylamino; a di(C 1 -C 4 )alkylamino radical, wherein the two alkyl groups may form, together with the nitrogen atom to which they are attached, a ring that may be interrupted with at least one nitrogen, oxygen, or sulfur atom; a heterocycle; a nitro radical; a phenyl radical; a carbonyl radical; a (C 1 -C 4 )alkoxycarbonyl radical; a carboxamido radical; a cyano radical; an amino radical; a sulfonyl radical; a —CO 2 H radical, a —SO 3 H radical, a —PO 3 H 2 radical, a —PO 4 H 2 radical, or a group:
wherein R′″ is chosen from an oxygen or nitrogen atom, Q is chosen from an oxygen atom, a NH group, or NH(C 1 -C 4 )alkyl, and Y is chosen from a hydroxyl, amino, C 1 -C 4 alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylamino, or di(C 1 -C 4 )alkylamino radical;
A2) pyrazolopyridine oxidation bases according to formula (II) below
wherein:
Z 1 and Z 2 , independently of each other, are chosen from:
a covalent single bond; or
a divalent radical chosen from:
a —O(CH 2 ) p — radical, wherein p is chosen from an integer ranging from 0 to 6, or
a —NR′ 6 (CH 2 ) q (C 6 H 4 ) t — radical, wherein q is chosen from an integer ranging from 0 to 6, t is chosen from 0 or 1, and R′ 6 is chosen from a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted with at least one hydroxyl group;
Z 1 may also be chosen from a divalent radical —S—, —SO—, or —SO 2 —, wherein R′ 1 is a methyl radical;
R′ 1 and R′ 2 , independently of each other, are chosen from:
a hydrogen atom;
a C 1 -C 10 alkyl radical, which is optionally substituted and optionally interrupted with a heteroatom or a group chosen from O, N, Si, S, SO, or SO 2 ;
a halogen;
a SO 3 H radical;
a substituted or unsubstituted, saturated, unsaturated, or aromatic, 5- to 8-membered ring, optionally containing at least one heteroatom or group chosen from N, O, S, SO 2 , or —CO—, wherein the ring is optionally cationic and/or substituted with a cationic radical; or
a —N + R 19 R 18 R 19 group, wherein R 17 , R 18 , and R 19 are linear or branched C 1 -C 5 alkyls optionally substituted with at least one hydroxyl group;
wherein when Z 1 represents a covalent bond, then R 1 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
wherein when Z 2 represents a covalent bond, then R 2 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
R′ 3 , R′ 4 , and R′ 5 , which may be identical or different, are chosen from:
a hydrogen atom;
a hydroxyl radical;
a C 1 -C 6 alkoxy radical;
a C 1 -C 6 alkylthio radical;
an amino radical;
a monoalkylamino radical;
a C 1 -C 6 dialkylamino radical, wherein the alkyl radicals may form, with the nitrogen atom to which they are attached, a saturated or unsaturated, aromatic or nonaromatic, 5- to 8-membered heterocycle, which may contain at least one heteroatom or group chosen from N, O, S, SO 2 , and CO, wherein the heterocycle is optionally cationic and/or substituted with a cationic radical;
an optionally substituted C 1 -C 6 alkylcarbonyl radical;
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′ independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
a halogen;
a —NHSO 3 H radical;
an optionally substituted C 1 -C 4 alkyl radical;
a saturated, unsaturated or aromatic, optionally substituted carbon-based ring; or
R′ 3 , R′ 4 , and R′ 5 optionally form in pairs a partially saturated or unsaturated ring, and
X is chosen from an ion or group of ions making it possible to ensure the electronegativity of the derivative of formula (II);
wherein least one of the groups R′ 1 or R′ 2 is chosen from a cationic radical; or
A3) diamino-N,N-dihydropyrazolone derivatives according to formula (III) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R″ 3 and R″ 4 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 6 alkyl radical optionally substituted with at least one radical chosen from a OR″ 5 radical, a NR″ 6 R″ 7 radical, a carboxyl radical, a sulfonic radical, a carboxamido CONR″ 6 R″ 7 radical, a sulfonamido radical SO 2 NR″ 6 R″ 7 , a heteroaryl, an aryl optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino group;
an aryl radical optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino;
a 5- or 6-membered heteroaryl radical, optionally substituted with at least one radical chosen from (C 1 -C 4 )alkyl or (C 1 -C 2 )alkoxy; or
R″ 3 and R″ 4 optionally form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which is optionally replaced with an optionally substituted oxygen or nitrogen atom;
R″ 5 , R″ 6 , and R″ 7 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one radical chosen from hydroxyl, C 1 -C 2 alkoxy, carboxamido CONR″ 8 R″ 9 , sulfonyl SO 2 R″ 8 , aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino, aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino or (di)alkyl(C 1 -C 2 )amino; or
R″ 6 and R″ 7 , which may be identical or different, are optionally chosen from a carboxamido radical CONR″ 8 R″ 9 or a sulfonyl radical SO 2 R″ 8 ;
R″ 8 and R″ 9 , which may be identical or different, are chosen from a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one hydroxyl or C 1 -C 2 alkoxy; and
R″ 1 and R″ 2 form, together with the nitrogen atom(s) to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally substituted with at least one radical chosen from halogen atoms and amino, (di)alkyl(C 1 -C 4 )amino, hydroxyl, carboxyl, carboxamido and (C 1 -C 2 )alkoxy radicals, C 1 -C 4 alkyl radicals optionally substituted with at least one hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, or sulfonyl radical.
2. The composition according to claim 1 , wherein the pyrazolopyridines of formula (I) are chosen from those according to the formula below:
wherein:
R 1 , R 2 , and R 3 , which may be identical or different, are chosen from a hydrogen atom; a halogen atom; a hydroxyl radical; a (C 1 -C 4 )alkyl radical; a (C 1 -C 4 )alkylthio radical; a (C 1 -C 4 )alkoxy radical; a —NHSO 3 H radical; an amino radical; a (C 1 -C 4 )alkylamino radical; a di(C 1 -C 4 )alkylamino radical, wherein the two alkyl groups may form, together with the nitrogen atom to which they are attached, a ring that may be interrupted with at least one nitrogen, oxygen, or sulfur atom; a heterocycle; a sulfonamide radical; a carbonyl radical; a (C 1 -C 4 )alkoxycarbonyl radical; a carboxamido radical; or a group:
wherein R′″ is chosen from an oxygen or nitrogen atom, Q is chosen from an oxygen atom, an NH group, or NH(C 1 -C 4 )alkyl, and Y is chosen from a hydroxyl, amino, C 1 -C 4 alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylamino, or di(Ci-C4)alkylamino radical.
3. The composition according to claim 1 , wherein the pyrazolopyridines of formula (I) are chosen from:
pyrazolo[1,5-a]pyridin-3-ylamine;
2-acetylaminopyrazolo[1,5-a]pyridin-3-ylamine;
2-morpholin-4-ylpyrazolo[1,5-a]pyridin-3-ylamine;
3-aminopyrazolo[1,5-a]pyridine-2-carboxylic acid;
2-methoxypyrazolo[1,5-a]pyridin-3-ylamino;
(3-aminopyrazolo[1,5-a]pyridin-7-yl)methanol;
2-(3-aminopyrazolo[1,5-a]pyridin-5-yl)ethanol;
2-(3-aminopyrazolo[1,5-a]pyridin-7-yl)ethanol;
(3-aminopyrazolo[1,5-a]pyridin-2-yl)methanol;
3,6-diaminopyrazolo[1,5-a]pyridine;
3,4-diaminopyrazolo[1,5-a]pyridine;
pyrazolo[1,5-a]pyridine-3,7-diamine;
7-morpholin-4-ylpyrazolo[1,5-a]pyridin-3-ylamine;
pyrazolo[1,5-a]pyridine-3,5-diamine;
5-morpholin-4-ylpyrazolo[1,5-a]pyridin-3-ylamine;
2-[(3-aminopyrazolo[1,5-a]pyridin-5-yl)(2-hydroxyethyl)amino]ethanol;
2-[(3-aminopyrazolo[1,5-a]pyridin-7-yl)(2-hydroxyethyl)amino]ethanol;
3-aminopyrazolo[1,5-a]pyridin-5-ol;
3-aminopyrazolo[1,5-a]pyridin-4-ol;
3-aminopyrazolo[1,5-a]pyridin-6-ol;
3-aminopyrazolo[1,5-a]pyridin-7-ol;
2-methoxy-6,7-dimethylpyrazolo[1,5-a]pyridin-3-amine;
2-[(3-aminopyrazolo[1,5-a]pyridin-2-yl)oxy]ethanol;
4-ethyl-2-methoxy-7-methylpyrazolo[1,5-a]pyridin-3-amine hydrochloride;
1-(3-aminopyrazolo[1,5-a]pyridin-2-yl)pyrrolidin-3-ol;
2,2′-[(3-aminopyrazolo[1,5-a]pyridin-2-yl)imino]diethanol;
2-[(3-aminopyrazolo[1,5-a]pyridin-2-yl)amino]ethanol;
N2-(2-pyridin-3-ylethyl)pyrazolo[1,5-a]pyridine-2,3-diamine; or
addition salts thereof, solvates thereof, or solvates of the salts thereof.
4. The composition according to claim 1 , wherein the pyrazolopyridine oxidation bases are chosen from compounds according to formula (II) below:
wherein:
Z 1 is chosen from:
a covalent single bond; or
a divalent radical chosen from:
a —O(CH 2 ) p — radical, wherein p is chosen from an integer ranging from 0 to 6, or
a —NR′ 6 (CH 2 ) q (C 6 H 4 ) t — radical, wherein q is chosen from an integer ranging from 0 to 6, t is chosen from 0 or 1, and R′ 6 is chosen from a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted with at least one hydroxyl group; or
a radical —S—, —SO—, or —SO 2 —, wherein R′ 1 is a methyl radical;
R′ 1 is chosen from:
a hydrogen atom;
a C 1 -C 10 alkyl radical, which is optionally substituted and optionally interrupted with a heteroatom or a group chosen from O, N, Si, S, SO, or SO 2 ;
a halogen;
a SO 3 H radical;
a substituted or unsubstituted, saturated, unsaturated, or aromatic, 5- to 8-membered ring, optionally containing at least one heteroatom or group chosen from N, O, S, SO 2 , or —CO—, wherein the ring is optionally cationic and/or substituted with a cationic radical; or
a —N + R 19 R 18 R 19 group, wherein R 17 , R 18 and R 19 are linear or branched C 1 -C 5 alkyls optionally substituted with at least one hydroxyl group;
wherein when Z 1 represents a covalent bond, then R 1 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical;
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
wherein when Z 2 represents a covalent bond, then R 2 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
R′ 3 , R′ 4 , and R′ 5 , which may be identical or different, are chosen from:
a hydrogen atom;
a hydroxyl radical;
a C 1 -C 6 alkoxy radical;
a C 1 -C 6 alkylthio radical;
an amino radical;
a monoalkylamino radical;
a C 1 -C 6 dialkylamino radical, wherein the alkyl radicals may form, with the nitrogen atom to which they are attached, a saturated or unsaturated, aromatic or nonaromatic, 5- to 8-membered heterocycle, which optionally contain at least one heteroatom or group chosen from N, O, S, SO 2 , and CO, wherein the heterocycle is optionally cationic and/or substituted with a cationic radical;
an optionally substituted C 1 -C 6 alkylcarbonyl radical;
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
a halogen;
a —NHSO 3 H radical;
an optionally substituted C 1 -C 4 alkyl radical;
a saturated, unsaturated or aromatic, optionally substituted carbon-based ring; or
R′ 3 , R′ 4 , and R′ 5 optionally form in pairs a partially saturated or unsaturated ring.
5. The composition according to claim 1 , wherein the compounds of formulae (I) and (II) are chosen from:
4-(3-Aminopyrazolo[1,5-a]pyridin-2-yl)-1,1-dimethylpiperazin-1-ium salt
3-[2-(3-Aminopyrazolo[1,5-a]pyridin-2-ylamino)ethyl]-1-methyl-3H-imidazol-1-ium salt,
2-[(3-aminopyrazolo[1,5-a]pyridin-2-yl)oxy]ethanol, or addition salts thereof, solvates thereof, or solvates of the salts thereof.
6. The composition according to claim 1 , wherein R″ 1 and R″ 2 form, together with the nitrogen atom(s) to which they are attached, an optionally substituted saturated or unsaturated 5- or 6-membered ring, optionally substituted with at least one C 1 -C 4 alkyl radical, a hydroxyl, a (C 1 -C 2 )alkoxy, a carboxyl, a carboxamido, an amino, or a (di)(C 1 -C 2 )alkylamino.
7. The composition according to claim 1 , wherein R″ 3 and R″ 4 are chosen from a hydrogen atom; a linear or branched C 1 -C 6 alkyl radical optionally substituted with at least one hydroxyl, (C 1 -C 2 )alkoxy, amino or (di)(C 1 -C 2 )alkylamino; or a phenyl radical optionally substituted with at least one hydroxyl, amino, or (C 1 -C 2 )alkoxy.
8. The composition according to claim 1 , wherein the diamino-N,N-dihydropyrazolone derivatives according to formula (III) are chosen from:
2,3-diamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2-amino-3-ethylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2-amino-3-isopropylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2-amino-3-(pyrrolidin-1-yl)-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2-amino-3-(2-hydroxyethyl)amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2-amino-3-dimethylamino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one;
2,3-diamino-5,6,7,8-tetrahydro-1H,6H-pyridazino[1,2-a]pyrazol-1-one;
2,3-diamino-6-hydroxy-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one; or
addition salts thereof, solvates thereof, or solvates of the salts thereof.
9. The composition according to claim 1 , further comprising at least one surfactant.
10. The composition according to claim 9 , wherein the at least one surfactant is chosen from non-ionic surfactants.
11. The composition according to claim 1 , further comprising at least one alkaline agent.
12. The composition according to claim 1 , wherein the at least one pyrazole heterocyclic oxidation base is present in a total amount ranging from about 0.0001% to about 20% by weight, relative to the total weight of the composition.
13. The composition according to claim 1 , wherein the at least one pyrazole heterocyclic oxidation base is present in a total amount ranging from about 0.005% to about 10% by weight, relative to the total weight of the composition.
14. The composition according to claim 1 , further comprising at least one chemical oxidizing agent.
15. The composition according to claim 14 , wherein the at least one chemical oxidizing agent is chosen from hydrogen peroxide.
16. A method for dyeing keratin fibers, comprising applying to the keratin fibers a dye composition, the dye composition comprising:
(A) at least one 2-amino-5-ethylphenol coupler, an addition salt thereof, or a solvate thereof,
(B) at least one pyrazole heterocyclic oxidation base chosen from:
A1) pyrazolopyridines according to formula (I) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R 1 , R 2 , R 3 , R 4 , and R 5 , which may be identical or different, are chosen from a hydrogen atom, a halogen atom; a —NHSO 3 H radical, a hydroxyl radical, a (C 1 -C 4 )alkyl radical, a (C 1 -C 4 )alkoxy radical, a (C 1 -C 4 )alkylthio radical, mono(C 1 -C 4 )alkylamino, a di(C 1 -C 4 )alkylamino radical, wherein the two alkyl groups may form, together with the nitrogen atom to which they are attached, a ring that may be interrupted with at least one nitrogen, oxygen, or sulfur atom, a heterocycle, a nitro radical, a phenyl radical, a carbonyl radical; a (C 1 -C 4 )alkoxycarbonyl radical, a carboxamido radical, a cyano radical, an amino radical, a sulfonyl radical, a —CO 2 H radical, a —SO 3 H radical, a —PO 3 H 2 radical, a —PO 4 H 2 radical, or a group:
wherein R′″ is chosen from an oxygen or nitrogen atom, Q is chosen from an oxygen atom, a NH group, or NH(C 1 -C 4 )alkyl, and Y is chosen from a hydroxyl, amino, C 1 -C4 alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylamino, or di(Ci-C4)alkylamino radical;
A2) pyrazolopyridine oxidation bases according to formula (II) below
wherein:
Z 1 and Z 2 , independently of each other, are chosen from:
a covalent single bond; or
a divalent radical chosen from:
a —O(CH 2 ) p — radical, wherein p is chosen from an integer ranging from 0 to 6, or
a —NR′ 6 (CH 2 ) q (C 6 H 4 ) t — radical, wherein q is chosen from an integer ranging from 0 to 6 and t is chosen from 0 or 1, and R′ 6 is chosen from a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted with at least one hydroxyl group;
Z 1 may also be chosen from a divalent radical —S—, —SO—, or —SO 2 —, wherein R′ 1 is a methyl radical;
R′ 1 and R′ 2 , independently of each other, are chosen from:
a hydrogen atom;
a C 1 -C 10 alkyl radical, which is optionally substituted and optionally interrupted with a heteroatom or a group chosen from O, N, Si, S, SO, or SO 2 ;
a halogen;
a SO 3 H radical;
a substituted or unsubstituted, saturated, unsaturated, or aromatic, 5- to 8-membered ring, optionally containing at least one heteroatom or group chosen from N, O, S, SO 2 , or —CO—, wherein the ring is optionally cationic and/or substituted with a cationic radical; or
a —N + R 19 R 18 R 19 group, wherein R 17 , R 18 , and R 19 are linear or branched C 1 -C 5 alkyls optionally substituted with at least one hydroxyl group;
wherein when Z 1 represents a covalent bond, then R 1 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
wherein when Z 2 represents a covalent bond, then R 2 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
R′ 3 , R′ 4 , and R′ 5 , which may be identical or different, are chosen from:
a hydrogen atom;
a hydroxyl radical;
a C 1 -C 6 alkoxy radical;
a C 1 -C 6 alkylthio radical;
an amino radical;
a monoalkylamino radical;
a C 1 -C 6 dialkylamino radical, wherein the alkyl radicals may form, with the nitrogen atom to which they are attached, a saturated or unsaturated, aromatic or nonaromatic, 5- to 8-membered heterocycle, which may contain at least one heteroatom or group chosen from N, O, S, SO 2 , and CO, wherein the heterocycle is optionally cationic and/or substituted with a cationic radical;
an optionally substituted C 1 -C 6 alkylcarbonyl radical;
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′ independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
a halogen;
a —NHSO 3 H radical;
an optionally substituted C 1 -C 4 alkyl radical;
a saturated, unsaturated or aromatic, optionally substituted carbon-based ring; or
R′ 3 , R′ 4 , and R′ 5 optionally form in pairs a partially saturated or unsaturated ring, and
X is chosen from an ion or group of ions making it possible to ensure the electronegativity of the derivative of formula (II);
wherein least one of the groups R′ 1 or R′ 2 is chosen from a cationic radical; or
A3) diamino-N,N-dihydropyrazolone derivatives according to formula (III) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R″ 3 and R″ 4 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 6 alkyl radical optionally substituted with at least one radical chosen from a OR″ 5 radical, a NR″ 6 R″ 7 radical, a carboxyl radical, a sulfonic radical, a carboxamido CONR″ 6 R″ 7 radical, a sulfonamido radical SO 2 NR″ 6 R″ 7 , a heteroaryl, an aryl optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino group;
an aryl radical optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino;
a 5- or 6-membered heteroaryl radical, optionally substituted with at least one radical chosen from (C 1 -C 4 )alkyl or (C 1 -C 2 )alkoxy; or
R″ 3 and R″ 4 optionally form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which is optionally replaced with an optionally substituted oxygen or nitrogen atom;
R″ 5 , R″ 6 , and R″ 7 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one radical chosen from hydroxyl, C 1 -C 2 alkoxy, carboxamido CONR″ 8 R″ 9 , sulfonyl SO 2 R″ 8 , aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino, aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino or (di)alkyl(C 1 -C 2 )amino; or
R″ 6 and R″ 7 , which may be identical or different, are optionally chosen from a carboxamido radical CONR″ 8 R″ 9 or a sulfonyl radical SO 2 R″ 8 ;
R″ 8 and R″ 9 , which may be identical or different, are chosen from a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one hydroxyl or C 1 -C 2 alkoxy; and
R″ 1 and R″ 2 form, together with the nitrogen atom(s) to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally substituted with at least one radical chosen from halogen atoms and amino, (di)alkyl(C 1 -C 4 )amino, hydroxyl, carboxyl, carboxamido and (C 1 -C 2 )alkoxy radicals, C 1 -C 4 alkyl radicals optionally substituted with at least one hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, or sulfonyl radicals.
17. A multi-compartment device for dyeing keratin fibers, comprising:
at least one first compartment comprising a dye composition, wherein the dye composition comprises:
(A) at least one 2-amino-5-ethylphenol coupler, an addition salt thereof, or a solvate thereof,
(B) at least one pyrazole heterocyclic oxidation base chosen from:
A1) pyrazolopyridines according to formula (I) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R 1 , R 2 , R 3 , R 4 , and R 5 , which may be identical or different, are chosen from a hydrogen atom, a halogen atom, a —NHSO 3 H radical, a hydroxyl radical, a (C 1 -C 4 )alkyl radical, a (C 1 -C 4 )alkoxy radical, a (C 1 -C 4 )alkylthio radical, mono(C 1 -C 4 )alkylamino, a di(C 1 -C 4 )alkylamino radical, wherein the two alkyl groups may form, together with the nitrogen atom to which they are attached, a ring that may be interrupted with at least one nitrogen, oxygen, or sulfur atom, a heterocycle; a nitro radical; a phenyl radical, a carbonyl radical, a (C 1 -C 4 )alkoxycarbonyl radical, a carboxamido radical, a cyano radical, an amino radical, a sulfonyl radical, a —CO 2 H radical, a —SO 3 H radical, a —PO 3 H 2 radical, a —PO 4 H 2 radical, or a group:
wherein R′″ is chosen from an oxygen or nitrogen atom, Q is chosen from an oxygen atom, a NH group, or NH(C 1 -C 4 )alkyl, and Y is chosen from a hydroxyl, amino, C 1 -C 4 alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylamino, or di(C 1 -C 4 )alkylamino radical;
A2) pyrazolopyridine oxidation bases according to formula (II) below
wherein:
Z 1 and Z 2 , independently of each other, are chosen from:
a covalent single bond; or
a divalent radical chosen from:
a —O(CH 2 ) p — radical, wherein p is chosen from an integer ranging from 0 to 6, or
a —NR′ 6 (CH 2 ) q (C 6 H 4 ) t — radical, wherein q is chosen from an integer ranging from 0 to 6 and t is chosen from 0 or 1, and R′ 6 is chosen from a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted with at least one hydroxyl group;
Z 1 may also be chosen from a divalent radical —S—, —SO—, or —SO 2 —, wherein R′ 1 is a methyl radical;
R′ 1 and R′ 2 , independently of each other, are chosen from:
a hydrogen atom;
a C 1 -C 10 alkyl radical, which is optionally substituted and optionally interrupted with a heteroatom or a group chosen from O, N, Si, S, SO, or SO 2 ;
a halogen;
a SO 3 H radical;
a substituted or unsubstituted, saturated, unsaturated, or aromatic, 5- to 8-membered ring, optionally containing at least one heteroatom or group chosen from N, O, S, SO 2 , or —CO—, wherein the ring is optionally cationic and/or substituted with a cationic radical; or
a —N + R 19 R 18 R 19 group, wherein R 17 , R 18 and R 19 are linear or branched C 1 -C 5 alkyls optionally substituted with at least one hydroxyl group;
wherein when Z 1 represents a covalent bond, then R 1 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
wherein when Z 2 represents a covalent bond, then R 2 optionally represents:
an optionally substituted C 1 -C 6 alkylcarbonyl radical; or
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′, independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
R′ 3 , R′ 4 and R′ 5 , which may be identical or different, are chosen from:
a hydrogen atom;
a hydroxyl radical;
a C 1 -C 6 alkoxy radical;
a C 1 -C 6 alkylthio radical;
an amino radical;
a monoalkylamino radical;
a C 1 -C 6 dialkylamino radical, wherein the alkyl radicals may form, with the nitrogen atom to which they are attached, a saturated or unsaturated, aromatic or nonaromatic, 5- to 8-membered heterocycle, which may contain at least one heteroatom or group chosen from N, O, S, SO 2 , and CO, wherein the heterocycle is optionally cationic and/or substituted with a cationic radical;
an optionally substituted C 1 -C 6 alkylcarbonyl radical;
a radical —O—CO—R, —CO—O—R, NR—CO—R′, or —CO—NRR′, wherein R and R′ independently of each other, are chosen from a hydrogen atom or an optionally substituted C 1 -C 6 alkyl radical;
a halogen;
a —NHSO 3 H radical;
an optionally substituted C 1 -C 4 alkyl radical;
a saturated, unsaturated or aromatic, optionally substituted carbon-based ring; or
R′ 3 , R′ 4 , and R′ 5 optionally form in pairs a partially saturated or unsaturated ring, and
X is chosen from an ion or group of ions making it possible to ensure the electronegativity of the derivative of formula (II);
wherein least one of the groups R′ 1 or R′ 2 is chosen from a cationic radical; or
A3) diamino-N,N-dihydropyrazolone derivatives according to formula (III) below, addition salts thereof, solvates thereof, or solvates of the salts thereof:
wherein:
R″ 3 and R″ 4 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 6 alkyl radical optionally substituted with at least one radical chosen from a OR″ 5 radical, a NR″ 6 R″ 7 radical, a carboxyl radical, a sulfonic radical, a carboxamido CONR″ 6 R″ 7 radical, a sulfonamido radical SO 2 NR″ 6 R″ 7 , a heteroaryl, an aryl optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino groups;
an aryl radical optionally substituted with at least one (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino;
a 5- or 6-membered heteroaryl radical, optionally substituted with at least one radical chosen from (C 1 -C 4 )alkyl or (C 1 -C 2 )alkoxy; or
R″ 3 and R″ 4 optionally form, together with the nitrogen atom to which they are attached, a 5- or 7-membered heterocycle, the carbon atoms of which may be replaced with an optionally substituted oxygen or nitrogen atom;
R″ 5 , R″ 6 , and R″ 7 , which may be identical or different, are chosen from:
a hydrogen atom;
a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one radical chosen from hydroxyl, C 1 -C 2 alkoxy, carboxamido CONR″ 8 R″ 9 , sulfonyl SO 2 R″ 8 , aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino, or (di)alkyl(C 1 -C 2 )amino, aryl optionally substituted with a (C 1 -C 4 )alkyl, hydroxyl, C 1 -C 2 alkoxy, amino or (di)alkyl(C 1 -C 2 )amino; or
R″ 6 and R″ 7 , which may be identical or different, are optionally chosen from a carboxamido radical CONR″ 8 R″ 9 or a sulfonyl radical SO 2 R″ 8 ;
R″ 8 and R″ 9 , which may be identical or different, are chosen from a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical optionally substituted with at least one hydroxyl or C 1 -C 2 alkoxy; and
R″ 1 and R″ 2 form, together with the nitrogen atom(s) to which they are attached, a saturated or unsaturated 5- to 7-membered heterocycle optionally substituted with at least one radical chosen from halogen atoms and amino, (di)alkyl(C 1 -C 4 )amino, hydroxyl, carboxyl, carboxamido and (C 1 -C 2 )alkoxy radicals, C 1 -C 4 alkyl radicals optionally substituted with at least one hydroxyl, amino, (di)alkylamino, alkoxy, carboxyl, or sulfonyl radicals.
18. The composition according to claim 1 , wherein the at least one 2-amino-5-ethylphenol coupler is present in a total amount ranging from about 0.0001% to about 20% by weight, relative to the total weight of the composition.
19. The composition according to claim 1 , wherein the at least one 2-amino-5-ethylphenol coupler is present in a total amount ranging from about 0.005% to about 10% by weight, relative to the total weight of the composition.
20. The composition according to claim 1 , wherein the at least one 2-amino-5-ethylphenol coupler is present in a total amount ranging from about 0.01% to about 6% by weight, relative to the total weight of the composition.