Naphthalene cationic coupler for oxidation dyeing of keratin fiber
AssigneeL'oreal
InventorsJean-Jacques Vandenbossche, Alain Lagrange
Life of this patent
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Abstract
The invention relates to a composition for the oxidation dyeing of keratin fibers, and in particular of human keratin fibers such as the hair, comprising at least one oxidation base and, as coupler, at least one 2-hydroxynaphthalene of formula (I) comprising at least one cationic group Z of formula (II), to their use as couplers for the oxidation dyeing of keratin fibers, to oxidation dyeing processes using them and to novel cationic 2-hydroxynaphthalenes of formula (I′).
Claims73
A composition for oxidation dyeing keratin fibres comprising, in a medium appropriate for dyeing:
- at least one coloring compound chosen from oxidation bases and acid addition salts of said oxidation bases, and
- at least one coupler chosen from compounds of formula (I) below and acid addition salts thereof:
- wherein:
- groups R1, R2 and R3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L:
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom.
A liquid, a cream, or a gel for dyeing keratin fibers comprising, in a medium appropriate for dyeing:
- at least one coloring compound chosen from oxidation bases and acid addition salts of said oxidation bases, and
- at least one coupler chosen from compounds of formula (I) below and acid addition salts thereof:
- wherein:
- groups R1, R2 and R3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (II), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said inker D s bonded to the nitrogen atom that is bonded to E and L;
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5-and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom.
A process for oxidation dyeing keratin fibers comprising
- (A) applying to said keratin fibers at least one dyeing composition comprising, in a medium appropriate for dyeing:
- at least one coloring compound chosen from oxidation bases and acid addition salts of said oxidation bases, and
- at least one coupler chosen from compounds of formula (I) below and acid addition salts thereof:
- wherein:
- groups R1, R2 and R3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom;
- and
- (B) developing a color with at least one oxidizing agent, wherein said oxidizing agent is combined at the time of use with said at least one dyeing composition or said at least one oxidizing agent is applied simultaneously with or sequentially to said at least one dyeing composition.
A process for oxidation dyeing keratin fibers comprising
- (A) applying to said keratin fibers at least one dyeing composition comprising, in a medium appropriate for dyeing:
- at least one coloring compound chosen from oxidation bases and acid addition salts of said oxidation bases, and
- at least one coupler chosen from compounds of formula (I) below and acid addition salts thereof:
- wherein:
- groups R1, R2 and R3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6 alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-Cr)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom;
- and
- (B) developing a color with at least one oxidizing agent present in an amount sufficient to develop a color, wherein said at least one oxidizing agent is combined at the time of use with said at least one dyeing composition,
- (C) leaving said combination to act for a time ranging from 3 to 50 minutes, and
- (D) rinsing said keratinous fibers, shampooing said keratinous fibers after said shampooing, and drying said keratinous fibers.
A kit comprising two compartments, wherein:
- (a) a first compartment comprises at least one dyeing composition comprising, in a medium suitable for dyeing:
- at least one coloring compound chosen from oxidation bases and acid addition salts of said oxidation bases, and
- at least one coupler chosen from compounds of formula (I) below and acid addition salts thereof:
- wherein:
- groups R1, R2 and R3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl group, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from:
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom;
- and
- (b) a second compartment comprises at least one oxidizing agent.
A compound of formula (I′) or an acid addition salt thereof:
- wherein:
- R′1, R′2 and R′3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1,y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom;
- and
- provided that when two of R′1, R′2, and R′3 simultaneously are a hydrogen atom, and when the other group R′1, R′2, and R′3 is a group comprising a functional group chosen from amido and carboxyl functional groups, then said amido and carboxyl functional group is not directly bonded to the naphthol ring system;
- and further excluding:
- 6-hydroxy-N,N,N-trimethyl-1-naphthalenemethanaminium chloride;
- and
- [(2-hydroxy-1-naphthyl)methyl]trimethylammonium iodide.
A process for dyeing keratin fibers comprising applying to said keratin fibers at least one coupler chosen from compounds of formula (I′) and acid addition salts thereof:
- wherein:
- R′1, R′2 and R′3, which may be identical or different, are each chosen from:
- (1) a hydrogen and a halogen atom;
- (2) groups Z chosen from groups of formulae (II), (III), and (IV):
- wherein:
- linker D is chosen from linear and branched divalent alkylene groups, optionally comprising at least one hetero atom, and optionally substituted with at least one group chosen from hydroxyl groups and C1-C6alkoxy groups, and optionally comprising at least one ketone functional group;
- E, G, J, L and M, which may be identical or different, are each an atom chosen from carbon, oxygen, sulfur, and nitrogen;
- n is an integer ranging from 0 to 4;
- m is an integer ranging from 0 to 5;
- R, which may be identical or different, are each chosen from:
- groups Z, as defined above;
- a halogen atom, a hydroxyl group, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, (C1-C6)alkylcarbonyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, groups NHR2 and NR2R′″ in which R2 and R′″, which may be identical or different, are each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups and C2-C6polyhydroxyalkyl groups;
- R5 is chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, cyano(C1-C6)alkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, benzyl groups, and groups Z, as defined above;
- R6, R7 and R8, which may be identical or different, are each chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, aryl groups, benzyl groups, C1-C6amidoalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups;
- two of the groups R6, R7 and R8 can together also form, with the nitrogen atom to which said two groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered carbon-based rings comprising at least one hetero atom, it being possible for said at least one ring to be substituted with at least one unit chosen from halogen atoms, hydroxyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, nitro groups, cyano groups, cyano(C1-C6)alkyl groups, C1-C6alkoxy groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, amido groups, aldehydo groups, carboxyl groups, keto(C1-C6)alkyl groups, thio groups, C1-C6thioalkyl groups, C1-C6alkylthio groups, amino groups optionally protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups and groups Z, as defined above;
- R9 is a group chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, aryl groups, benzyl groups, C1-C6aminoalkyl groups, C1-C6aminoalkyl groups, wherein the amine is protected with at least one group chosen from (C1-C6)alkylcarbonyl groups, carbamyl groups and C1-C6alkylsulfonyl groups, carboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, tri(C1-C6)alkylsilane(C1-C6)alkyl groups, C1-C6sulfonamidoalkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylketo(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, and N—(C1-C6)alkylsulfonamido(C1-C6)alkyl groups;
- a and y, which may be identical or different, are each chosen from 0 and 1, provided that:
- in said groups of formula (II) at least one of the following applies:
- 1) a=0, y=0, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 2) a=0, y=1, E, G, J, and L are carbon atoms, and said linker D and R5 are bonded to the nitrogen atom that is bonded to E and L;
- 3) a=0, y=1, at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded, and said linker D is bonded to the nitrogen atom that is bonded to E and L;
- 4) a=1, y=0, said linker D is bonded to one of said ring members chosen from E, G, J and L;
- 5) a=1, y=1, said ring members E, G, J, and L are carbon atoms one of which is bonded to said linker D, and R5 is bonded to the nitrogen atom that is bonded to E and L;
- and
- 6) a=1, y=1, said linker D is bonded to one of said ring members chosen from E, G, J and L, and at least one of said ring members E, G, J, and L is a nitrogen atom to which R5 is bonded;
- in said groups of formula (III) at least one of the following applies:
- 1) a=0, y=0, said linker D is bonded to the nitrogen atom that is bonded to E and M;
- 2) a=0, y=1, said linker D and said R5 are bonded to the nitrogen atom that is bonded to E and L, and at least one of said ring members E, G, J, L, and M is chosen from divalent atoms;
- 3) a=1, y=0, said linker D is bonded to a said ring member chosen from E, G, J, L, and M;
- 4) a=1, y=1, at least one of said ring members E, G, J, L, and M is chosen from divalent atoms one of which is bonded to said linker D, and said R5 is bonded to the nitrogen atom that is bonded to E and M;
- in said groups of formula (IV) at least one of the following applies:
- 1) a=0, y=0 or 1, said linker D is bonded to the nitrogen that is bonded to groups R6, R7, and R8;
- 2) a=1, y=0 or 1, two of the groups R6, R7, and R8 form, together with the nitrogen atom to which said groups are commonly bonded, at least one saturated ring chosen from 5- and 6-membered rings as defined above, and said linker D is bonded to a carbon atom of said at least one saturated ring;
- X− is chosen from monovalent anions and divalent anions;
- provided that said compounds of formula (I) comprise at least one group Z;
- (3) (C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl groups, carboxyl groups, (C1-C6)alkylcarboxyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkoxy(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, and cyano groups, wherein Z is defined above;
- (4) groups —OR4 and groups —SR4, wherein said R4 are chosen from:
- C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, and C2-C6polyhydroxyalkyl groups, groups Z as defined above, (C1-C6)alkoxy(C1-C6)alkyl groups, aryl groups, benzyl groups, carboxy(C1-C6)alkyl groups, (C1-C6)alkylcarboxy(C1-C6)alkyl groups, cyano(C1-C6)alkyl groups, carbamyl(C1-C6)alkyl groups, N—(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl groups, C1-C6trifluoroalkyl groups, C1-C6aminosulfonylalkyl groups, C1-C6N—Z-aminosulfonylalkyl groups, N—(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, N,N-di(C1-C6)alkylaminosulfonyl(C1-C6)alkyl groups, (C1-C6)alkylsulfinyl(C1-C6)alkyl groups, (C1-C6)alkylsulfonyl(C1-C6)alkyl groups, (C1-C6)alkylcarbonyl(C1-C6)alkyl groups, C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group, C1-C6aminoalkyl groups, wherein said alkyl is unsubstituted or substituted with at least one hydroxyl group and, wherein said amine is substituted with one or two groups, which may be identical or different, each chosen from C1-C6alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, thiocarbamyl groups and C1-C6alkylsulfonyl groups and groups Z as defined above, and, when said amine is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based rings and rings comprising at least one hetero atom;
- (5) amino groups protected with at least one group chosen from
- (C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, trifluoro(C1-C6)alkylcarbonyl groups, amino(C1-C6)alkylcarbonyl groups, N—Z-amino(C1-C6)alkylcarbonyl groups, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, C1-C6alkylsulfonyl groups, aminosulfonyl groups, N—Z-aminosulfonyl groups, C1-C6N-alkylaminosulfonyl groups, N,N-di(C1-C6)alkylaminosulfonyl groups, thiocarbamyl groups, formyl groups, and groups Z as defined above wherein said linker D in said groups Z comprises at least one ketone functional group directly bonded to the nitrogen atom of said amino group;
- (6) C1-C6aminoalkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group;
- (7) amino(C1-C6)alkyl groups, wherein the alkyl is optionally substituted with at least one hydroxyl group and wherein said amino is substituted with one or two groups, which may be identical or different, chosen from alkyl groups, C1-C6monohydroxyalkyl groups, C2-C6polyhydroxyalkyl groups, (C1-C6)alkylcarbonyl groups, carbamyl groups, N—(C1-C6)alkylcarbamyl groups, N,N-di(C1-C6)alkylcarbamyl groups, (C1-C6)alkylsulfonyl groups, formyl groups, trifluoro(C1-C6)alkylcarbonyl groups, (C1-C6)alkylcarboxyl groups, thiocarbamyl groups, and said groups Z as defined above, and, when said amino is substituted with two groups, said two groups may optionally form, together with the nitrogen atom to which said two groups are commonly bonded, at least one ring chosen from 5- and 6-membered carbon-based ring and 5- and 6-membered rings comprising at least one hetero atom;
- and
- provided that when two of R′1, R′2, and R′3 simultaneously are a hydrogen atom, and when the other group R′1, R′2, and R′3 is a group comprising a functional group chosen from amido and carboxyl functional groups, then said amido and carboxyl functional group is not directly bonded to the naphthol ring system;
- and further excluding:
- 6-hydroxy-N,N,N-trimethyl-1-naphthalenemethanaminium chloride;
- and
- [(2-hydroxy-1-naphthyl)methyl]trimethylammonium iodide.
Dependencies are inferred from the claim text.