Cationic couplers and their use for oxidation dyeing
AssigneeL'oreal
InventorsJean-Jacques Vandenbossche, Laurent Vidal, Jean-Baptiste Saunier, Alain LaGrange
Life of this patent
Estimating the term…
Abstract
The subject of the invention is novel compounds derived from naphth-1-ol comprising at least one cationic group, their use as coupler for the oxidation dyeing of keratinous fibres, compositions for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, containing them in combination with at least one oxidation base, as well as methods of oxidation dyeing using them.
Claims36
A compound of the following formula (I) or an acid addition salt thereof;
- wherein:
- R1 represents a group chosen from —NR4(C═O)R5, —NR6SO2R7 and —(C═O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
- R2 and R3, which are identical or different, represent a hydrogen atom;
- a halogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical is linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that:
- the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond;
- and R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- R2 and R3 cannot represent a hydroxyl radical or a thio radical;
- R2 and R3 cannot each represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
- Y represents a hydrogen or halogen atom;
- a group —OR9, —SR9, or —NH—SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 6 members, wherein the radical may be unsubstituted or substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, and C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- a phenyl radical, wherein the phenyl radical may be unsubstituted or substituted with one or two radicals chosen from C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- or a benzyl radical;
- R4, R6 and R8, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 15 carbon atoms, linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
- it being understood that the —(C═O)— group is not directly linked to the nitrogen atom carrying the radical R6;
- it being understood that the radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, or an alkylthio radical;
- R5 and R7, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bond chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
- it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
- it being understood that R7 cannot represent a thio radical;
- it being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, the members being chosen from carbon, nitrogen and acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
- Z is a cationic group represented by the following formula (II):
- wherein:
- n can take the value 0 or 1;
- B represents an alkyl radical comprising from 1 to 15 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, and wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an —SO2 radical;
- and wherein one or more carbon atoms in the radical may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z;
- the said radical B containing no peroxide bond or diazo, nitro, or nitroso radicals;
- D is chosen from the cationic groups of the following formulae (III) and (IV):
- wherein:
- p and q can, independently of each other, take the value 0 or 1;
- the radical B is linked to the group D by any one of the atoms of the radical D;
- when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
- Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom;
- a sulphur atom;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- or a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
- Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
- Z6 can have the same meanings as those indicated below for the radical R14;
- it being understood that Z6 is different from a hydrogen atom;
- the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
- R14 represents a hydrogen atom;
- a group Z;
- or a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and wherein one or more carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
- it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
- it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- X− represents an organic or inorganic anion;
- with the proviso that at least one of the groups R1 to R3 represents or contains a group Z.
A method of dyeing of keratinous fibres, comprising dyeing the fibres with an oxidation base and an oxidation coupler, wherein the coupler is chosen from a compound of the following formula (I) or an acid addition salt thereof:
- wherein:
- R1 represents a group chosen from —NR4(C═O)R5, —NR6SO2R7 and —(C═O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
- R2 and R3, which are identical or different, represent a hydrogen atom;
- a halogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical is linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that:
- the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond;
- and R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- R2 and R3 cannot represent a hydroxyl radical or a thio radical;
- R2 and R3 cannot each represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
- Y represents a hydrogen or halogen atom;
- a group —OR9, —SR9, or —NH—SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 6 members, wherein the radical may unsubstituted or substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, and C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- a phenyl radical, wherein the phenyl radical may be unsubstituted or substituted with one or two radicals chosen from C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- or a benzyl radical;
- R4, R6 and R8, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 15 carbon atoms, linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
- it being understood that the —(C═O)— group is not directly linked to the nitrogen atom carrying the radical R6;
- it being understood that the radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, or an alkylthio radical;
- R5 and R7, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bond chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
- it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
- it being understood that R7 cannot represent a thio radical;
- it being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, the members being chosen from carbon, nitrogen and acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
- Z is a cationic group represented by the following formula (II):
- wherein:
- n can take the value 0 or 1;
- B an alkyl radical comprising from 1 to 15 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, and wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an —SO2 radical;
- and wherein one or more carbon atoms in the radical may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z;
- the said radical B containing no peroxide bond or diazo, nitro, or nitroso radicals;
- D is chosen from the cationic groups of the following formulae (III) and (IV):
- wherein:
- p and q can, independently of each other, take the value 0 or 1;
- the radical B is linked to the group D by any one of the atoms of the radical D;
- when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
- Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom;
- a sulphur atom;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- or a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
- Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
- Z6 can have the same meanings as those indicated below for the radical R14;
- it being understood that Z6 is different from a hydrogen atom;
- the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
- R14 represents a hydrogen atom;
- a group Z;
- or a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and wherein one or more carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
- it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
- it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- X− represents an organic or inorganic anion;
- with the proviso that at least one of the groups R1 to R3 represents or contains a group Z.
A composition for the oxidation dyeing of keratinous fibres, comprising, in a medium appropriate for dyeing:
- at least one oxidation base, and
- at least one coupler chosen from a compound of the following formula (I) or an acid addition salt thereof:
- wherein:
- R1 represents a group chosen from —NR4(C═O)R5, —NR6SO2R7 and —(C═O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
- R2 and R3, which are identical or different, represent a hydrogen atom;
- a halogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical is linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple, bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that:
- the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond;
- and R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- R2 and R3 cannot represent a hydroxyl radical or a thio radical;
- R2 and R3 cannot each represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
- Y represents a hydrogen or halogen atom;
- a group —OR9, —SR9, or —NH—SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 6 members, wherein the radical may unsubstituted or substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, and C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- a phenyl radical, wherein the phenyl radical may be unsubstituted or substituted with one or two radicals chosen from C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- or a benzyl radical;
- R4, R6 and R8, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 15 carbon atoms, linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
- it being understood that the —(C═O)— group is not directly linked to the nitrogen atom carrying the radical R6;
- it being understood that the radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, or an alkylthio radical;
- R5 and R7, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bond chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
- it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
- it being understood that R7 cannot represent a thio radical;
- it being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, the members being chosen from carbon, nitrogen and acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
- Z is a cationic group represented by the following formula (II):
- wherein:
- n can take the value 0 or 1;
- B represents an alkyl radical comprising from 1 to 15 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, and wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an —SO2 radical;
- and wherein one or more carbon atoms in the radical may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z;
- the said radical B containing no peroxide bond or diazo, nitro, or nitroso radicals;
- D is chosen from the cationic groups of the following formulae (III) and (IV):
- wherein:
- p and q can, independently of each other, take the value 0 or 1;
- the radical B is linked to the group D by any one of the atoms of the radical D;
- when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
- Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom;
- a sulphur atom;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- or a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
- Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
- Z6 can have the same meanings as those indicated below for the radical R14;
- it being understood that Z6 is different from a hydrogen atom;
- the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
- R14 represents a hydrogen atom;
- a group Z;
- or a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and wherein one or more carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
- q
- it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
- it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- X− represents an organic or inorganic anion;
- with the proviso that at least one of the groups R1 to R3 represents or contains a group Z.
A method of oxidation dyeing of keratinous fibres, comprising:
- applying to the fibers at least one dyeing composition;
- and
- developing a color at a pH chosen from acidic, neutral and alkaline pH with the aid of an oxidizing agent which is added just at the time of use to the dyeing composition and which is present in an oxidizing composition applied at least one of simultaneously and sequentially in a separate manner,
- wherein the at least one dyeing composition comprises in a medium appropriate for dyeing:
- at least one oxidation base, and
- at least one coupler chosen from a compound of the following formula (I) or an acid addition salt thereof:
- wherein:
- R1 represents a group chosen from —NR4(C═O)R5, —NR6SO2R7 and —(C═O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
- R2 and R3, which are identical or different, represent a hydrogen atom;
- a halogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical is linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that:
- the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond;
- and R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- R2 and R3 cannot represent a hydroxyl radical or a thio radical;
- R2 and R3 cannot each represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
- Y represents a hydrogen or halogen atom;
- a group —OR9, —SR9, or —NH—SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 6 members, wherein the radical may unsubstituted or substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, and C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- a phenyl radical, wherein the phenyl radical may be unsubstituted or substituted with one or two radicals chosen from C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- or a benzyl radical;
- R4, R6 and R8, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 15 carbon atoms, linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
- it being understood that the —(C═O)— group is not directly linked to the nitrogen atom carrying the radical R6;
- it being understood that the radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, or an alkylthio radical;
- R5 and R7, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bond chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
- it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
- it being understood that R7 cannot represent a thio radical;
- it being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, the members being chosen from carbon, nitrogen and acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
- Z is a cationic group represented by the following formula (II):
- wherein:
- n can take the value 0 or 1;
- B represents an alkyl radical comprising from 1 to 15 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, and wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an —SO2 radical;
- and wherein one or more carbon atoms in the radical may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z;
- the said radical B containing no peroxide bond or diazo, nitro, or nitroso radicals;
- D is chosen from the cationic groups of the following formulae (III) and (IV):
- wherein
- p and q can, independently of each other, take the value 0 or 1;
- the radical B is linked to the group D by any one of the atoms of the radical D;
- when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
- Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom;
- a sulphur atom;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- or a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
- Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
- Z6 can have the same meanings as those indicated below for the radical R14;
- it being understood that Z6 is different from a hydrogen atom;
- the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
- R14 represents a hydrogen atom;
- a group Z;
- or a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and wherein one or more carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
- it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
- it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- X− represents an organic or inorganic anion;
- with the proviso that at least one of the groups R1 to R3 represents or contains a group Z.
A multicompartment device or multicompartment dyeing “kit”, comprising a first compartment and a second compartment, wherein the first compartment comprises at least one dyeing composition, and the second compartment comprises an oxidizing composition,
- wherein the dyeing composition comprises in a medium appropriate for dyeing:
- at least one oxidation base, and
- at least one coupler chosen from a compound of the following formula (I) or an acid addition salt thereof:
- wherein:
- R1 represents a group chosen from —NR4(C═O)R5, —NR6SO2R7 and —(C═O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
- R2 and R3, which are identical or different, represent a hydrogen atom;
- a halogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical is linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that:
- the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an —NH—NH— bond;
- and R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- R2 and R3 cannot represent a hydroxyl radical or a thio radical;
- R2 and R3 cannot each represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
- Y represents a hydrogen or halogen atom;
- a group —OR9, —SR9, or —NH—SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 6 members, wherein the radical may unsubstituted or substituted with one or more radicals chosen from halogen atoms, hydroxyl radicals, and C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- a phenyl radical, wherein the phenyl radical may be unsubstituted or substituted with one or two radicals chosen from C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino, and amino(C1-C4 alkyl) radicals;
- or a benzyl radical;
- R4, R6 and R8, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 15 carbon atoms, linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
- it being understood that the —(C═O)— group is not directly linked to the nitrogen atom carrying the radical R6;
- it being understood that the radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
- it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, or an alkylthio radical;
- R5 and R7, which are identical or different, represent a hydrogen atom;
- a group Z as defined below;
- or a radical comprising from 1 to 20 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more carbon-containing rings comprising from 3 to 7 members, wherein the radical may contain bond chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
- it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
- it being understood that R7 cannot represent a thio radical;
- it being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, the members being chosen from carbon, nitrogen and acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen, or sulphur atom or with an SO2 group, and wherein the carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
- Z is a cationic group represented by the following formula (II):
- wherein:
- n can take the value 0 or 1;
- B represents an alkyl radical comprising from 1 to 15 carbon atoms, wherein the radical may be linear or branched, wherein the branch(es) may form one or more rings comprising from 3 to 7 members, wherein the radical may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, and wherein one or more carbon atoms in the radical may be replaced with an oxygen, nitrogen or sulphur atom or with an —SO2 radical;
- and wherein one or more carbon atoms in the radical may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z;
- the said radical B containing no peroxide bond or diazo, nitro, or nitroso radicals;
- D is chosen from the cationic groups of the following formulae (III) and (IV):
- wherein:
- p and q can, independently of each other, take the value 0 or 1;
- the radical B is linked to the group D by any one of the atoms of the radical D;
- when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
- Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom;
- a sulphur atom;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- or a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
- Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
- Z6 can have the same meanings as those indicated below for the radical R14;
- it being understood that Z6 is different from a hydrogen atom;
- the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
- R14 represents a hydrogen atom;
- a group Z;
- or a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain bonds chosen from one or more double bonds and one or more triple bonds, wherein the double bonds may lead to aromatic groups, wherein one or more carbon atoms of the radical may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and wherein one or more carbon atoms of the radical may, independently of each other, be substituted with one or more halogen atoms;
- the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
- it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
- it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different;
- a nitrogen atom which is unsubstituted or substituted with a radical R14;
- an oxygen atom;
- or a sulphur atom;
- X− represents an organic or inorganic anion;
- with the proviso that at least one of the groups R1 to R3 represents or contains a group Z.
Dependencies are inferred from the claim text.