Cationic azo dyes with julolidine units, dyeing composition containing them, method of dyeing

A method for dyeing keratin fibers, comprising:

• applying to the keratin fibers a dyeing composition comprising at least one direct dye,
• leaving the composition on the keratin fibers for a waiting time ranging from 3 minutes to 1 hour;
• and
• rinsing the keratin fibers,
• wherein said direct dye is chosen from cationic azo compounds with a julolidine unit of formula (I):
• wherein:
• A is a cationic aromatic heterocycle chosen from compounds of formulae (IIa), (IIb), and (IIc):
• wherein:
• R1 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one carbon ring with 3 to 7 ring members, optionally condensed with the aromatic ring, optionally substituted, optionally interrupted by at least one group chosen from heteroatom chosen from oxygen, nitrogen and sulphur, and carbonyl groups;
• wherein R1 does not contain a nitro, nitroso, peroxide and diazo bond;
• and wherein R1 is directly attached to the nitrogen atom, quaternized or not, of the heteroaromatic ring A by means of a carbon atom;
• R2 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one aromatic or non-aromatic carbon ring, with 3 to 6 ring members, optionally substituted, optionally interrupted by at least one heteroatom or by at least one group bearing at least one heteroatom;
• hydroxyl groups;
• C1-C4 alkoxy groups;
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups, R11O—CO—, wherein R11 is chosen from C1-C4 alkyl radicals;
• alkylcarbonyloxy radicals, R12CO—O—, wherein R12 is chosen from C1-C4 alkyl radicals;
• amino groups and amino groups substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, wherein the two alkyl radicals optionally form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members optionally bearing another heteroatom identical to or different from nitrogen;
• alkylcarbonylamino groups, R13CO—NR13— and R13CO—NH—, wherein the radicals R13, independently of one another, are chosen from C1-C4 alkyl radicals;
• carbamoyl groups, (R14)2N—CO, wherein the radicals R14, independently of one another, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups, (R15)2N—CO—NR16—, wherein the radicals R15 and R16, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• sulphonamide groups, (R17)2N—SO2—, wherein the radicals R17, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups, R18SO2—NR19—, wherein the radicals R18 and R19, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• guanidinium groups, (R20)2N—C(═NH2+)—NR21−, wherein the radicals R20 and R21, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• wherein two radicals R2, carried by adjacent carbon atoms optionally form, together with the carbon atom to which each is attached, an aromatic or non-aromatic condensed ring;
• m is an integer ranging from 0 to 4;
• e is an integer ranging from 0 to 2;
• p is an integer ranging from 0 to 1;
• D is chosen from groups CR2 and nitrogen atoms;
• Q is chosen from groups NR1 and atoms of oxygen and sulphur;
• bond a from formulae (IIa), (IIb) or (IIc), joins group A to the azo group;
• when two radicals R2 carried by two adjacent carbon atoms form an aromatic ring, bond a optionally joins group A to the azo group via said aromatic ring;
• wherein the electroneutrality of the compounds is provided by at least one anion An−, which may be identical or different, and is cosmetically acceptable;
• X, Y and Z are optional substituents on the alkyl and aryl rings of the three-ring nucleus;
• x is an integer ranging from 0 to 2;
• y is an integer ranging from 0 to 6;
• and
• z is an integer ranging from 0 to 6;
• or their addition salts or their solvates,
• wherein, in the definitions above, when an alkyl radical or the alkyl part of a radical is substituted, said substituted alkyl comprises at least one substituent chosen from:
• hydroxyl groups,
• C1-C4 alkoxy groups and C2-C4 (poly)hydroxyalkoxy groups,
• amino groups and amino groups substituted with at least one C1-C4 alkyl group, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• wherein, in the definitions above, when an aryl or heteroaryl radical or the aryl or heteroaryl part of a radical is substituted, said substituted aryl or heteroaryl comprises at least one substituent carried by a carbon atom, wherein for the aromatic ring of the three ring nucleus of said julolidine unit said substituent is X, and wherein X or said at least one substituent is chosen from:
• C1-C16 alkyl radicals, optionally substituted with at least one radical chosen from hydroxy, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, acylamino, amino substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 7 ring members, optionally containing another heteroatom identical to or different from nitrogen;
• halogen atoms;
• hydroxyl groups;
• C1-C2 alkoxy radicals;
• C2-C4 (poly)-hydroxyalkoxy radicals;
• amino radicals;
• amino radicals substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group;
• acylamino radicals, —NR31—COR32, wherein the radical R31 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group and the radical R32 is chosen from C1-C2 alkyl radicals;
• carbamoyl radicals, (R33)2N—CO—, wherein the radicals R33, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• alkylsulphonylamino radicals, R34SO2—NR35—, wherein the radical R34 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R35 is chosen from C1-C4 alkyl radicals and phenyl radicals;
• aminosulphonyl radicals, (R36)2N—SO2—, wherein the radicals R36, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• wherein, in the definitions above, when the cyclic or heterocyclic part of a non-aromatic radical is substituted, it comprises at least one substituent carried by a carbon atom, wherein for the non-aromatic rings of the three ring nucleus of said julolidine unit said substituents are Y and Z, and wherein Y and Z or said at least one substituent is chosen from:
• hydroxyl groups,
• C1-C4 alkoxy and C2-C4 (poly)hydroxyalkoxy radicals,
• alkylcarbonylamino radicals, (R41CO—NR42—, wherein the radical R42 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R41 is chosen from C1-C2 alkyl radicals and amino radicals substituted with two C1-C4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• wherein for all definitions above, when a ring does not carry the maximum number of substituents, the unsubstituted position or positions then carry a hydrogen atom.

A composition for dyeing keratin fibers comprising, in a suitable dyeing medium, at least one direct dye chosen from cationic azo compounds with a julolidine unit of formula (I):

• wherein:
• A is a cationic aromatic heterocycle compound chosen from compounds of formulae (IIa), (IIb), and (IIc):
• wherein:
• R1 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one carbon ring with 3 to 7 ring members, optionally condensed with the aromatic ring, optionally substituted, optionally interrupted by at least one group chosen from heteroatom chosen from oxygen, nitrogen and sulphur, and carbonyl groups;
• wherein R1 does not contain a nitro, nitroso, peroxide and diazo bond;
• and wherein R1 is directly attached to the nitrogen atom, quaternized or not, of the heteroaromatic ring A by means of a carbon atom;
• R2 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one aromatic or non-aromatic carbon ring, with 3 to 6 ring members, optionally substituted, optionally interrupted by at least one heteroatom or by at least one group bearing at least one heteroatom;
• hydroxyl groups;
• C1-C4 alkoxy groups;
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups, R11O—CO—, wherein R11 is chosen from C1-C4 alkyl radicals;
• alkylcarbonyloxy radicals, R12CO—O—, wherein R12 is chosen from C1-C4 alkyl radicals;
• amino groups and amino groups substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, wherein the two alkyl radicals optionally form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members optionally bearing another heteroatom identical to or different from nitrogen;
• alkylcarbonylamino groups, R13CO—NR13— and R13CO—NH—, wherein the radicals R13, independently of one another, are chosen from C1-C4 alkyl radicals;
• carbamoyl groups, (R14)2N—CO, wherein the radicals R14, independently of one another, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups, (R15)2N—CO—NR16—, wherein the radicals R15 and R16, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• sulphonamide groups, (R17)2N—SO2—, wherein the radicals R17, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups, R18SO2—NR19—, wherein the radicals R18 and R19, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• guanidinium groups, (R20)2N—C(═NH2+)—NR21—, wherein the radicals R20 and R21, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• wherein two radicals R2, carried by adjacent carbon atoms optionally form, together with the carbon atom to which each is attached, an aromatic or non-aromatic condensed ring;
• m is an integer ranging from 0 to 4;
• e is an integer ranging from 0 to 2;
• p is an integer ranging from 0 to 1;
• D is chosen from groups CR2 and nitrogen atoms;
• Q is chosen from groups NR1 and atoms of oxygen and sulphur;
• bond a from formulae (IIa), (IIb) or (IIc), joins group A to the azo group;
• when two radicals R2 carried by two adjacent carbon atoms form an aromatic ring, bond a optionally joins group A to the azo group via said aromatic ring;
• wherein the electroneutrality of the compounds is provided by at least one anion An−, which may be identical or different, and are cosmetically acceptable;
• X, Y and Z are optional substituents on the alkyl and aryl rings of the three-ring nucleus;
• x is an integer ranging from 0 to 2;
• y is an integer ranging from 0 to 6;
• and
• z is an integer ranging from 0 to 6;
• or their addition salts or their solvates,
• wherein, in the definitions above, when an alkyl radical or the alkyl part of a radical is substituted, said substituted alkyl comprises at least one substituent chosen from:
• hydroxyl groups,
• C1-C4 alkoxy groups and C2-C4 (poly)hydroxyalkoxy groups,
• amino groups and amino groups substituted with at least one C1-C4 alkyl group, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• wherein, in the definitions above, when an aryl or heteroaryl radical or the aryl or heteroaryl part of a radical is substituted, said substituted aryl or heteroaryl comprises at least one substituent carried by a carbon atom, wherein for the aromatic ring of the three ring nucleus of said julolidine unit said substituent is X, and wherein X or said at least one substituent is chosen from:
• C1-C16 alkyl radicals, optionally substituted with at least one radical chosen from hydroxy, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, acylamino, amino substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 7 ring members, optionally containing another heteroatom identical to or different from nitrogen;
• halogen atoms;
• hydroxyl groups;
• C1-C2 alkoxy radicals;
• C2-C4 (poly)-hydroxyalkoxy radicals;
• amino radicals;
• amino radicals substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group;
• acylamino radicals, —NR31—COR32, wherein the radical R31 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group and the radical R32 is chosen from C1-C2 alkyl radicals;
• carbamoyl radicals, (R33)2N—CO—, wherein the radicals R33, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• alkylsulphonylamino radicals, R34SO2—NR35—, wherein the radical R34 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R35 is chosen from C1-C4 alkyl radicals and phenyl radicals;
• aminosulphonyl radicals, (R36)2N—SO2—, wherein the radicals R36, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• wherein, in the definitions above, when the cyclic or heterocyclic part of a non-aromatic radical is substituted, it comprises at least one substituent carried by a carbon atom, wherein for the non-aromatic rings of the three ring nucleus of said julolidine unit said substituents are Y and Z, and wherein Y and Z or said at least one substituent is chosen from:
• hydroxyl groups,
• C1-C4 alkoxy and C2-C4 (poly)hydroxyalkoxy radicals,
• alkylcarbonylamino radicals, (R41CO—NR42—, wherein the radical R42 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R41 is chosen from C1-C2 alkyl radicals and amino radicals substituted with two C1-C4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen,
• wherein for all definitions above, when a ring does not carry the maximum number of substituents, the unsubstituted position or positions then carry a hydrogen atom.

A kit comprising:

• a first compartment comprising a composition comprising at least one direct dye, and
• a second compartment comprising a composition comprising at least one oxidizing agent,
• wherein said at least one direct dye is chosen from cationic azo compounds having a julolidine unit of formula (I):
• wherein:
• A is a cationic aromatic heterocycle chosen from compounds of formulae (IIa), (IIb), and (IIc):
• wherein:
• R1 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one carbon ring with 3 to 7 ring members, optionally condensed with the aromatic ring, optionally substituted, optionally interrupted by at least one group chosen from heteroatom chosen from oxygen, nitrogen and sulphur, and carbonyl groups;
• wherein R1 does not contain a nitro, nitroso, peroxide and diazo bond;
• and wherein R1 is directly attached to the nitrogen atom, quaternized or not, of the heteroaromatic ring A by means of a carbon atom;
• R2 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one aromatic or non-aromatic carbon ring, with 3 to 6 ring members, optionally substituted, optionally interrupted by at least one heteroatom or by at least one group bearing at least one heteroatom;
• hydroxyl groups;
• C1-C4 alkoxy groups;
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups, R11O—CO—, wherein R11 is chosen from C1-C4 alkyl radicals;
• alkylcarbonyloxy radicals, R12CO—O—, wherein R12 is chosen from C1-C4 alkyl radicals;
• amino groups and amino groups substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, wherein the two alkyl radicals optionally form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members optionally bearing another heteroatom identical to or different from nitrogen;
• alkylcarbonylamino groups, R13CO—NR13— and R13CO—NH—, wherein the radicals R13, independently of one another, are chosen from C1-C4 alkyl radicals;
• carbamoyl groups, (R14)2N—CO, wherein the radicals R14, independently of one another, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups, (R15)2N—CO—NR16—, wherein the radicals R15 and R16, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• sulphonamide groups, (R17)2N—SO2—, wherein the radicals R17, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups, R18SO2—NR19—, wherein the radicals R18 and R19, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• guanidinium groups, (R20)2N—C(═NH2+)—NR21—, wherein the radicals R20 and R21, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• wherein two radicals R2, carried by adjacent carbon atoms optionally form, together with the carbon atom to which each is attached, an aromatic or non-aromatic condensed ring;
• m is an integer ranging from 0 to 4;
• e is an integer ranging from 0 to 2;
• p is an integer ranging from 0 to 1;
• D is chosen from groups CR2 and nitrogen atoms;
• Q is chosen from groups NR1 and atoms of oxygen and sulphur;
• bond a from formulae (IIa), (IIb) or (IIc), joins group A to the azo group;
• when two radicals R2 carried by two adjacent carbon atoms form an aromatic ring, bond a optionally joins group A to the azo group via said aromatic ring;
• wherein the electroneutrality of the compounds is provided by at least one anion An−, which may be identical or different, and is cosmetically acceptable;
• X, Y and Z are optional substituents on the alkyl and aryl rings of the three-ring nucleus;
• x is an integer ranging from 0 to 2;
• y is an integer ranging from 0 to 6;
• and
• z is an integer ranging from 0 to 6;
• or their addition salts or their solvates,
• wherein, in the definitions above, when an alkyl radical or the alkyl part of a radical is substituted, said substituted alkyl comprises at least one substituent chosen from:
• hydroxyl groups,
• C1-C4 alkoxy groups and C2-C4 (poly)hydroxyalkoxy groups,
• amino groups and amino groups substituted with at least one C1-C4 alkyl group, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• wherein, in the definitions above, when an aryl or heteroaryl radical or the aryl or heteroaryl part of a radical is substituted, said substituted aryl or heteroaryl comprises at least one substituent carried by a carbon atom, wherein for the aromatic ring of the three ring nucleus of said julolidine unit said substituent is X, and wherein X or said at least one substituent is chosen from:
• C1-C16 alkyl radicals, optionally substituted with at least one radical chosen from hydroxy, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, acylamino, amino substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 7 ring members, optionally containing another heteroatom identical to or different from nitrogen;
• halogen atoms;
• hydroxyl groups;
• C1-C2 alkoxy radicals;
• C2-C4 (poly)-hydroxyalkoxy radicals;
• amino radicals;
• amino radicals substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group;
• acylamino radicals, —NR31—COR32, wherein the radical R31 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group and the radical R32 is chosen from C1-C2 alkyl radicals;
• carbamoyl radicals, (R33)2N—CO—, wherein the radicals R33, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• alkylsulphonylamino radicals, R34SO2—NR35—, wherein the radical R34 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R35 is chosen from C1-C4 alkyl radicals and phenyl radicals;
• aminosulphonyl radicals, (R36)2N—SO2—, wherein the radicals R36, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• wherein, in the definitions above, when the cyclic or heterocyclic part of a non-aromatic radical is substituted, it comprises at least one substituent carried by a carbon atom, wherein for the non-aromatic rings of the three ring nucleus of said julolidine unit said substituents are Y and Z, and wherein Y and Z or said at least one substituent is chosen from:
• hydroxyl groups,
• C1-C4 alkoxy and C2-C4 (poly)hydroxyalkoxy radicals,
• alkylcarbonylamino radicals, (R41CO—NR42—, wherein the radical R42 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R41 is chosen from C1-C2 alkyl radicals and amino radicals substituted with two C1-C4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• and
• wherein for all definitions above, when a ring does not carry the maximum number of substituents, the unsubstituted position or positions then carry a hydrogen atom.

A cationic azo compound having a julolidine unit of formula (I):

• wherein:
• A is a cationic aromatic heterocycle compound chosen from compounds of formulae (IIa), (IIb), and (IIc):
• wherein:
• R1 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one carbon ring with 3 to 7 ring members, optionally condensed with the aromatic ring, optionally substituted, optionally interrupted by at least one group chosen from heteroatom chosen from oxygen, nitrogen and sulphur, and carbonyl groups;
• wherein R1 does not contain a nitro, nitroso, peroxide and diazo bond;
• wherein R1 is directly attached to the nitrogen atom, quaternized or not, of the heteroaromatic ring A by means of a carbon atom;
• R2 is chosen from, independently of one another:
• linear and branched, saturated and unsaturated C1-C16 hydrocarbon chains, which optionally form at least one aromatic or non-aromatic carbon ring, with 3 to 6 ring members, optionally substituted, optionally interrupted by at least one heteroatom or by at least one group bearing at least one heteroatom;
• hydroxyl groups;
• C1-C4 alkoxy groups;
• C2-C4 (poly)hydroxyalkoxy groups;
• alkoxycarbonyl groups, R11O—CO—, wherein R11 is chosen from C1-C4 alkyl radicals;
• alkylcarbonyloxy radicals, R12CO—O—, wherein R12 is chosen from C1-C4 alkyl radicals;
• amino groups and amino groups substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, wherein the two alkyl radicals optionally form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members optionally bearing another heteroatom identical to or different from nitrogen;
• alkylcarbonylamino groups, R13CO—NR13— and R13CO—NH—, wherein the radicals R13, independently of one another, are chosen from C1-C4 alkyl radicals;
• carbamoyl groups, (R14)2N—CO, wherein the radicals R14, independently of one another, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• ureido groups, (R15)2N—CO—NR16—, wherein the radicals R15 and R16, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• sulphonamide groups, (R17)2N—SO2—, wherein the radicals R17, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• alkylsulphonylamino groups, R18SO2—NR19—, wherein the radicals R18 and R19, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• guanidinium groups, (R20)2N—C(═NH2+)—NR21—, wherein the radicals R20 and R21, independently of one another, are chosen from hydrogen atoms and C1-C4 alkyl radicals;
• nitro groups;
• cyano groups;
• halogen atoms;
• wherein two radicals R2, carried by adjacent carbon atoms optionally form, together with the carbon atom to which each is attached, an aromatic or non-aromatic condensed ring;
• m is an integer ranging from 0 to 4;
• e is an integer ranging from 0 to 2;
• p is an integer ranging from 0 to 1;
• D is chosen from groups CR2 and nitrogen atoms;
• Q is chosen from groups NR1 and atoms of oxygen and sulphur;
• bond a from formulae (IIa), (IIb) or (IIc), joins group A to the azo group;
• when two radicals R2 carried by two adjacent carbon atoms form an aromatic ring, bond a optionally joins group A to the azo group via said aromatic ring;
• wherein the electroneutrality of the compounds is provided by at least one anion An−, which may be identical or different, and are cosmetically acceptable;
• X, Y and Z are optional substituents on the alkyl and aryl rings of the three-ring nucleus;
• x is an integer ranging from 0 to 2;
• y is an integer ranging from 0 to 6;
• and
• z is an integer ranging from 0 to 6;
• or their addition salts or their solvates,
• wherein, in the definitions above, when an alkyl radical or the alkyl part of a radical is substituted, said substituted alkyl comprises at least one substituent chosen from:
• hydroxyl groups,
• C1-C4 alkoxy groups and C2-C4 (poly)hydroxyalkoxy groups,
• amino groups and amino groups substituted with at least one C1-C4 alkyl group, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• wherein, in the definitions above, when an aryl or heteroaryl radical or the aryl or heteroaryl part of a radical is substituted, said substituted aryl or heteroaryl comprises at least one substituent carried by a carbon atom, wherein for the aromatic ring of the three ring nucleus of said julolidine unit said substituent is X, and wherein X or said at least one substituent is chosen from:
• C1-C16 alkyl radicals, optionally substituted with at least one radical chosen from hydroxy, C1-C2 alkoxy, C2-C4 (poly)-hydroxyalkoxy, acylamino, amino substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 7 ring members, optionally containing another heteroatom identical to or different from nitrogen;
• halogen atoms;
• hydroxyl groups;
• C1-C2 alkoxy radicals;
• C2-C4 (poly)-hydroxyalkoxy radicals;
• amino radicals;
• amino radicals substituted with one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group;
• acylamino radicals, —NR31—COR32, wherein the radical R31 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group and the radical R32 is chosen from C1-C2 alkyl radicals;
• carbamoyl radicals, (R33)2N—CO—, wherein the radicals R33, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• alkylsulphonylamino radicals, R34SO2—NR35—, wherein the radical R34 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R35 is chosen from C1-C4 alkyl radicals and phenyl radicals;
• aminosulphonyl radicals, (R36)2N—SO2—, wherein the radicals R36, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group;
• wherein, in the definitions above, when the cyclic or heterocyclic part of a non-aromatic radical is substituted, it comprises at least one substituent carried by a carbon atom, wherein for the non-aromatic rings of the three ring nucleus of said julolidine unit said substituents are Y and Z, and wherein Y and Z or said at least one substituent is chosen from:
• hydroxyl groups,
• C1-C4 alkoxy and C2-C4 (poly)hydroxyalkoxy radicals,
• alkylcarbonylamino radicals, (R41CO—NR42—, wherein the radical R42 is chosen from hydrogen atoms and C1-C4 alkyl radicals optionally bearing at least one hydroxyl group, and the radical R41 is chosen from C1-C2 alkyl radicals and amino radicals substituted with two C1-C4 alkyl groups, which may be identical or different, optionally bearing at least one hydroxyl group, and said alkyl radicals can form, with the nitrogen atom to which they are attached, a heterocycle with 5 or 6 ring members, optionally containing at least one other heteroatom which may or may not be nitrogen;
• and
• wherein for all definitions above, when a ring does not carry the maximum number of substituents, the unsubstituted position or positions then carry a hydrogen atom,
• with the exception of
• 2-(9-julolidylazo)-3-methylbenzothiazolium perchlorate
• 2-(9-julolidylazo)-3-ethylthiazolium perchlorate.