Dyeing composition for dyeing keratinous fibres comprising a particular dicationic monoazo dye
AssigneeL'oreal
InventorsLaurent Vidal, Hervé David
Life of this patent
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Abstract
The invention concerns a novel dyeing composition for dying keratinous fibers, in particular human hair, comprising a dicationic monoazo dye, and the dyeing method using said composition and the novel compounds of formulae (I) or (II).
Claims40
A composition for dyeing keratinous fibers, comprising at least one dicationic monoazo dye chosen from compounds of the following formulae (I) and (II):
- Z1—N═N—A1—(A3)n—Z2 (I)
- Z1—N═N—A2 (II)
- wherein:
- n is equal to 0 or 1,
- Z1 is a 5- or 6-membered cationic heteroaromatic radical chosen from radicals of formulae (III) and (IV):
- wherein:
- X is NR3, S or O, Z is CR2 or N, and Y is CR4 or N,
- with the proviso that:
- when X is NR3 or O and Z is CR2, then Y is CR4 or N,
- when X is S, then Z is N or Y is N,
- when X is S and Z is N, then Y is CR4,
- X1 is CR6 or N,
- m is equal to 0, 1, 2 or 3,
- R1, R3 and R5, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom of the ring of formula (III) or (IV);
- wherein at least one of R1, R3 and R5 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R2, R4 and R6, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R2, R4 and R6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- the radicals R2 and R4 can form together a carbonaceous aromatic ring, and
- V is an organic or inorganic anion,
- A1 and A3, which may be identical or different, are each chosen from divalent radicals of formulae (V) and (VI)
- wherein
- n′ is equal to 0, 1, 2 or 3,
- n″ is equal to 0 or 1,
- Y1-Y2 is C—N or N—N,
- when n=0, then the bond a of the group A1 of formula (V) is connected to the functional group Z2 of formula (I) or,
- when n=0, then the bond b′ of the group A1 of formula (VI) is connected to the functional group Z2 of formula (I),
- when n=1, then the bond a of the group A1 of formula (V) is connected to the C1 of the group A3 of formula (V), the bond a of the group A3 of formula (V) being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond a of the group A1 of formula (V) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ being connected to the functional group Z2 of formula (I),
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the C1 carbon of the group A3 of formula (V), the bond a being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the carbon carrying the bond b′ of the group A3 of formula (VI), the bond a′ of the group A3 of formula (VI) being connected to the functional group Z2 of formula (I),
- R8 and R′8, which may be identical or different, are each a noncationic group chosen from a hydrogen atom and linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbon ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R8 and R′8 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R7, R9, R′7 and R′9, which may be identical or different, are each a cationic group Z3 or a noncationic group chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein the noncationic group does not comprise a peroxide bond or a diazo, nitro or nitroso radical, provided that only one of the groups R7, R9, R′7 and R′9 is cationic,
- R7 with R8, or R′7 with R′8 can form together a saturated 5- or 6-membered heterocycle,
- Z3 is a cationic group of the following formula (VII)
- —(B)n′″D (VII)
- wherein:
- B is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 15 carbon atoms, which can form at least one optionally aromatic 3- to 7-membered ring, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein B does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- the radical B is connected to D by any of the atoms of the radical D,
- n′″ is 0 or 1,
- D is a cationic group chosen from the cationic groups of the following formulae (VIII) and (IX):
- wherein:
- p is 0 or 1;
- T1, T2, T3 and T4, which may be identical or different, are each chosen from an oxygen atom;
- a sulfur atom;
- a nitrogen atom which is optionally substituted with at least one radical R14;
- and a carbon atom which is optionally substituted with one or two identical or different radicals R14;
- T5 is chosen from a nitrogen atom and a carbon atom which is optionally substituted with at least one radical R14;
- T6 is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group;
- wherein T6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- T1 or T5 can optionally form with T6 a 5- to 7-membered saturated or unsaturated ring, wherein each member of the ring is optionally substituted with one or two identical or different radicals R14;
- two of the adjacent radicals T1, T2, T3, T4 and T5 can optionally form a 5- to 7-membered ring, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom;
- R10, R11, R12, R13 and R14, which may be identical or different, are each chosen from a hydrogen atom and linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and wherein at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group, and/or can be substituted by, independently of one another, at least one halogen atom;
- wherein at least one of R10, R11, R12, R13 and R14 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R10, R11 and R12 can also form, in pairs with the quaternary nitrogen atom to which they are attached, at least one ring chosen from 5- to 7-membered saturated rings, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom,
- when n′″=0, then the group of formula (IX) can be connected to the compound of formula (V) and (VI) directly by the nitrogen atom of the quaternary ammonium, wherein R13 is a single bond, and
- V′ is an organic or inorganic anion,
- Z2 is chosen from linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, wherein the radical Z2 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- with a proviso that Z2 is not cationic when R7, R9, R′7 or R′9 is cationic,
- A2 is a radical of formula (X) chosen from carbonaceous aromatic, pyridine and pyridazine radicals substituted with at least one radical chosen from 5-membered cationic heteroaromatic radicals, optionally substituted with at least one noncationic radical R19 chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein R19 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- or a radical of formula (XI):
- wherein:
- r is equal to 0 or 1,
- q is equal to 0, 1, 2 or 3,
- s is equal to 0, 1, 2, 3, 4 or 5,
- t is equal to 0, 1, or 2,
- Y3═Y4 is C═C, C═N or N═N,
- if r=0, then X is O, S, NR18, CR20,
- if r=1, then X is CR20,
- R15 and R18, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R15, and R18 does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- R16, R17, R19, R20 and R21, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R16, R17, R19, R20, and R21 does not comprise a peroxide bond or a diazo, nitro or nitroso radical, and
- V″ is an organic or inorganic anion,
- provided that in formula (I), one of the groups A1, Z2 and A3 is a cationic group.
A process for oxidation dyeing of keratinous fibers, comprising applying to the keratinous fiber a dyeing composition comprising at least one dicationic monoazo dye chosen from compounds of the following formulae (I) and (II):
- Z1—N═N—A1—(A3)n—Z2 (I)
- Z1—N═N—A2 (II)
- wherein:
- n is equal to 0 or 1,
- Z1 is a 5- or 6-membered cationic heteroaromatic radical chosen from radicals of formulae (III) and (IV):
- wherein:
- X is NR3, S or O, Z is CR2 or N, and Y is CR4 or N,
- with the proviso that:
- when X is NR3 or O and Z is CR2, then Y is CR4 or N,
- when X is S, then Z is N or Y is N,
- when X is S and Z is N, then Y is CR4,
- X1 is CR6 or N,
- m is equal to 0, 1, 2 or 3,
- R1, R3 and R5, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom of the ring of formula (III) or (IV);
- wherein at least one of R1, R3 and R5 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R2, R4 and R6, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R2, R4 and R6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- the radicals R2 and R4 can form together a carbonaceous aromatic ring, and
- V is an organic or inorganic anion,
- A1 and A3, which may be identical or different, are each chosen from divalent radicals of formulae (V) and (VI)
- wherein
- n′ is equal to 0, 1, 2 or 3,
- n″ is equal to 0 or 1,
- Y1-Y2 is C—N or —N,
- when n=0, then the bond a of the group A1 of formula (V) is connected to the functional group Z2 of formula (I) or,
- when n=0, then the bond b′ of the group A1 of formula (VI) is connected to the functional group Z2 of formula (I),
- when n=1, then the bond a of the group A1 of formula (V) is connected to the C1 of the group A3 of formula (V), the bond a of the group A3 of formula (V) being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond a of the group A1 of formula (V) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ being connected to the functional group Z2 of formula (I),
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the C1 carbon of the group A3 of formula (V), the bond a being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ of the group A3 of formula (VI) being connected to the functional group Z2 of formula (I),
- R8 and R′8, which may be identical or different, are each a noncationic group chosen from a hydrogen atom and linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbon ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group with the exception of the carbon atom connected to the nitrogen atom wherein at least one of the radicals R8 and R′8 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R7, R9, R′7 and R′9, which may be identical or different, are each a cationic group Z3 or a noncationic group chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein the noncationic group does not comprise a peroxide bond or a diazo, nitro or nitroso radical, provided that only one of the groups R7, R9, R′7 and R′9 is cationic,
- R7 with R8, or R′7 with R′8 can form together a saturated 5- or 6-membered heterocycle,
- Z3 is a cationic group of the following formula (VII)
- —(B)n′″.D (VII)
- wherein:
- B is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 15 carbon atoms, which can form at least one optionally aromatic 3- to 7-membered ring, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least on entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein B does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- the radical B is connected to D by any of the atoms of the radical D,
- n′″ is 0 or 1,
- D is a cationic group chosen from the cationic groups of the following formulae (VIII) and (IX):
- wherein:
- p is 0 or 1;
- T1, T2, T3 and T4, which may be identical or different, are each chosen from an oxygen atom;
- a sulfur atom;
- a nitrogen atom which is optionally substituted with at least one radical R14;
- and a carbon atom which is optionally substituted with one or two identical or different radicals R14;
- T5 is chosen from a nitrogen atom and a carbon atom which is optionally substituted with at least one radical R14;
- T6 is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group;
- wherein T6 does not comprise a peroxide and or a diazo, nitro or nitroso radical;
- T1 or T5 can optionally form with T6 a 5- to 7-membered saturated or unsaturated ring, wherein each member of the ring is optionally substituted with one or two identical or different radicals R14;
- two of the adjacent radicals T1, T2, T3, T4 and T5 can optionally form a 5- to 7-membered ring, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom;
- R10, R11, R12, R13 and R14, which may be identical or different, are each chosen from a hydrogen atom and linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and wherein at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group, and/or can be substitute by, independently of one another, at least one halogen atom;
- wherein at least one of R10, R11, R12, R13 and R14 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R10, R11 and R12 can also form, in pairs with the quaternary nitrogen atom to which they are attached, at least one ring chosen from 5- to 7-membered saturated rings, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom,
- when n′″=0, then the group of formula (IX) can be connected to the compound of formula (V) and (VI) directly by the nitrogen atom of the quaternary ammonium, wherein R13 is a single bond, and
- V′ is an organic or inorganic anion,
- Z2 is chosen from linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, wherein the radical Z2 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- with a proviso that Z2 is not cationic when R7, R9, R′7 or R′9 is cationic,
- A2 is a radical of formula (X) chosen from carbonaceous aromatic, pyridine and pyridazine radicals substituted with at least one radical chosen from 5-membered cationic heteroaromatic radicals, optionally substituted with at least one noncationic radical R19 chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein R19 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- or a radical of formula (XI):
- wherein:
- r is equal to 0 or 1,
- q is equal to 0, 1, 2 or 3,
- s is equal to 0, 1, 2, 3, 4 or 5,
- t is equal to 0, 1 or 2,
- Y3═Y4 is C═C, C═N or N═N,
- if r=0, then X is O, S, NR18, CR20,
- if r=1, then X is CR20,
- R15 and R18, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R15, and R18 does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- R16, R17, R19, R20 and R21, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and SO2 group;
- wherein at least one of the radicals R16, R17, R19, R20, and R21 does not comprise a peroxide bond or a diazo, nitro or nitroso radical, and
- V″ is an organic or inorganic anion, provided that in formula (I), one of the groups A1, Z2 and A3 is a cationic group.
A multi-compartment device, comprising
- a first compartment comprising a dyeing composition comprising at least one dicationic monoazo dye chosen from compounds of the following formulae (I) and (II):
- Z1—N═N—A1—(A3)n—Z2 (I)
- Z1—N═N—A2 (II)
- wherein:
- n is equal to 0 or 1,
- Z1 is a 5- or 6-membered cationic heteroaromatic radical chosen from radicals of formulae (III) and (IV):
- wherein:
- X is NR3, S or O, Z is CR2 or N, and Y is CR4 or N,
- with the proviso that:
- when X is NR3 or O and Z is CR2, then Y is CR4;
- or N,
- when X is S, then Z is N or Y is N,
- when X is S and Z is N, then Y is CR4,
- X1 is CR6 or N,
- m is equal to 0, 1, 2 or 3,
- R1, R3 and R5, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom of the ring of formula (III) or (IV);
- wherein at least one of R1, R3 and R5 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R2, R4 and R6, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R2, R4 and R6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- the radicals R2 and R4 can form together a carbonaceous aromatic ring, and
- V is an organic or inorganic anion,
- A1 and A3, which may be identical or different, are each chosen from divalent radicals of formulae (V) and (VI)
- wherein
- n′ is equal to 0, 1, 2 or 3,
- n″ is equal to 0 or 1,
- Y1-Y2 is C—N or N—N,
- when n=0, then the bond a of the group A1 of formula (V) is connected to the functional group Z2 of formula (I) or,
- when n=0, then the bond b′ of the group A1 of formula (VI) is connected to the functional group Z2 of formula (I),
- when n=1, then the bond a of the group A1 of formula (V) is connected to the C1 of the group A3 of formula (V), the bond a of the group A3 of formula (V) being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond a of the group A1 of formula (V) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ being connected to the functional group Z2 of formula (I),
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the C1 carbon of the group A3 of formula (V), the bond a being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ of the group A3 of formula (VI) being connected to the functional group Z2 of formula (I),
- R8 and R′8, which may be identical or different, are each a noncationic group chosen from a hydrogen atom and linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbon ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R8 and R′8 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R7, R9, R′7 and R′9, which may be identical or different, are each a cationic group Z3 or a noncationic group chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein the noncationic group does not comprise a peroxide bond or a diazo, nitro or nitroso radical, provided that only one of the groups R7, R9, R′7 and R′9 is cationic,
- R7 with R8, or R′7 with R′8 can form together a saturated 5- or 6-membered heterocycle,
- Z3 is a cationic group of the following formula (VII)
- —(B)n′″.D (VII)
- wherein:
- B is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 15 carbon atoms, which can form at least one optionally aromatic 3- to 7-membered ring, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein B does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- the radical B is connected to D by any of the atoms of the radical D,
- n′″ is 0 or 1,
- D is a cationic group chosen from the cationic groups of the following formulae (VIII) and (IX):
- wherein:
- p is 0 or 1;
- T1, T2, T3 and T4, which may be identical or different, are each chosen from an oxygen atom;
- a sulfur atom;
- a nitrogen atom which is optionally substituted with at least one radical R14;
- and a carbon atom which is optionally substituted with one or two identical or different radicals R14;
- T5 is chosen from a nitrogen atom and a carbon atom which is optionally substituted with at least one radical R14;
- T6 is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group;
- wherein T6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- T1 or T5 can optionally form with T6 a 5- to 7-membered saturated or unsaturated ring, wherein each member of the ring is optionally substituted with one or two identical or different radicals R14;
- two of the adjacent radicals T1, T2, T3, T4 and T5 can optionally form a 5- to 7-membered ring, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom;
- R10, R11, R12, R13 and R14, which may be identical or different, are each chosen from a hydrogen atom and linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and wherein at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group, and/or can be substituted by, independently of one another, at least one halogen atom;
- wherein at least one of R10, R11, R12, R13 and R14 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R10, R11, an d R12 can also form, in pairs with the quaternary nitrogen atom to which they are attached, at least one ring chosen from 5- to 7-membered saturated rings, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom,
- when n′″=0, then the group of formula (IX) can be connected to the compound of formula (V) an (VI) directly by the nitrogen atom of the quaternary ammonium, wherein R13 is a single bond, and
- V′ is an organic or inorganic anion,
- Z2 is chosen from linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, wherein the radical Z2 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- with a proviso that Z2 is not cationic when R7, R9, R′7 or R′9 is cationic,
- A2 is a radical of formula (X) chosen from carbonaceous aromatic, pyridine and pyridazine radicals substituted with at least one radical chosen from 5-membered cationic heteroaromatic radicals, optionally substituted with at least one noncationic radical R19 chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein R19 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- or a radical of formula (XI):
- wherein:
- r is equal to 0 or 1,
- q is equal to 0, 1, 2 or 3,
- s is equal to 0, 1, 2, 3, 4 or 5,
- t is equal to 0, 1 or 2,
- Y3═Y4 is C═C, C═N or N═N,
- if r=0, then X is O, S, NR18, CR20,
- if r=1, then X is CR20,
- R15 and R18, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R15, and R18 does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- R16, R17, R19, R20 and R21, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R16, R17, R19, R20, and R21 does not comprise a peroxide bond or a diazo, nitro or nitroso radical, and
- V″ is an organic or inorganic anion, provided that in formula (I), one of the groups A1, Z2 and A3 is a cationic group, and
- a second compartment comprising an oxidizing composition.
A dicationic monoazo compound, chosen from compounds of formulae (I) and (II):
- Z1—N═N—A1—(A3)n—Z2 (I)
- Z1—N═N—A2 (II)
- wherein:
- n is equal to 0 or 1,
- Z1 is a 5- or 6-membered cationic heteroaromatic radical chosen from radicals of formulae (III) and (IV):
- wherein:
- X is NR3, S or O, Z is CR2 or N, and Y is CR4 or N,
- with the proviso that:
- when X is NR3 or O and Z is CR2, then Y is CR4 or N,
- when X is S, then Z is N or Y is N,
- when X is S and Z is N, then Y is CR4,
- X1 is CR6 or N,
- m is equal to 0, 1, 2 or 3,
- R1, R3 and R5, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom of the ring of formula (III) or (IV);
- wherein at least one of R1, R3 and R5 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R2, R4 and R6, which may be identical or different, are each chosen from a hydrogen atom and linear an branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein at least one of the radicals R2, R4 and R6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- the radicals R2 and R4 can form together a carbonaceous aromatic ring, and
- V is an organic or inorganic anion,
- A1 and A3, which may be identical or different, are each chosen from divalent radicals of formulae (V) and (VI)
- wherein
- n′ is equal to 0, 1, 2 or 3,
- n″ is equal to 0 or 1,
- Y1-Y2 is C—N or —N,
- when n=0, then the bond a of the group A1 of formula (V) is connected to the functional group Z2 of formula (I) or,
- when n=0, then the bond b′ of the group A1 of formula (VI) is connected to the functional group Z2 of formula (I),
- when n=1, then the bond a of the group A1 of formula (V) is connected to the C1 of the group A3 of formula (V), the bond a of the group A3 of formula (V) being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond a of the group A1 of formula (V) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ being connected to the functional group Z2 of formula (I),
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the C1 carbon of the group A3 of formula (V), the bond a being connected to the functional group Z2 of formula (I) or,
- when n=1, then the bond b′ of the group A1 of formula (VI) is connected to the carbon carrying the bond a′ of the group A3 of formula (VI), the bond b′ of the group A3 of formula (VI) being connected to the functional group Z2 of formula (I),
- R8 is a hydrogen atom
- R′8 is a noncationic group chosen from a hydrogen atom and linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbon ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group with the exception of the carbon atom connected to the nitrogen atom;
- wherein R′8 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R7, R9, R′7 and R′9, which may be identical or different, are each a cationic group Z3 or a noncationic group chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein the noncationic group does not comprise a peroxide bond or a diazo, nitro or nitroso radical, provided that only one of the groups R7, R9, R′7 and R′9 is cationic,
- R7 with R′8 can form together a saturated 5- or 6-membered heterocycle,
- Z3 is a cationic group of the following formula (VII)
- —(B)n′″.D (VII)
- wherein:
- B is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 15 carbon atoms, which can form at least one optionally aromatic 3- to 7-membered ring, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein B does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- the radical B is connected to D by any of the atoms of the radical D,
- n′″ is 0 or 1,
- D is a cationic group chosen from the cationic groups of the following formulae (VIII) and (IX):
- wherein:
- p is 0 or 1;
- T1, T2, T3 and T4, which may be identical or different, are each chosen from an oxygen atom;
- a sulfur atom;
- a nitrogen atom which is optionally substituted with at least one radical R14;
- and a carbon atom which is optionally substituted with one or two identical or different radicals R14;
- T5 is chosen from a nitrogen atom and a carbon atom which is optionally substituted with at least one radical R14;
- T8 is chosen from linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group;
- wherein T6 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- T1 or T5 can optionally form with T6 a 5- to 7-membered saturated or unsaturated ring, wherein each member of the ring is optionally substituted with one or two identical or different radicals R14;
- two of the adjacent radicals T1, T2, T3, T4 and T5 can optionally form a 5- to 7-membered ring, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is a optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom;
- R10, R11, R12, R13 and R14, which may be identical or different, are each chosen from a hydrogen atom and linear and branched hydrocarbonaceous chains comprising from 1 to 10 carbon atoms, which are optionally aromatic, and wherein at least one carbon atom of the hydrocarbonaceous chain can be replaced by at least one entity chosen from oxygen, nitrogen, halogen, and sulfur atoms and an SO2 group, and/or can be substituted by, independently of one another, at least one halogen atom;
- wherein at least one of R10, R11, R12, R13 and R14 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- R10, R11 and R12 can also form, in pairs with the quaternary nitrogen atom to which they are attached, at least one ring chosen from 5- to 7-membered saturated rings, wherein each member of the ring is chosen from a carbon atom which is optionally substituted with one or two identical or different radicals R14, a nitrogen atom which is optionally substituted with at least one radical R14, an oxygen atom, and a sulfur atom,
- when n′″=0, then the group of formula (IX) can be connected to the compound of formula (V) an (VI) directly by the nitrogen atom of the quaternary ammonium, wherein R13 is a single bond, and
- V′ is an organic or inorganic anion,
- Z2 is chosen from linear and branched C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group, wherein the radical Z2 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- with a proviso that Z2 is not cationic when R7, R9, R′7 or R′9 is cationic,
- A2 is a radical of formula (X) chosen from carbonaceous aromatic, pyridine and pyridazine radicals substituted with at least one radical chosen from 5-membered cationic heteroaromatic radicals optionally substituted with at least one noncationic radical R19 chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and an SO2 group;
- wherein R19 does not comprise a peroxide bond or a diazo, nitro or nitroso radical;
- or a radical of formula (XI):
- wherein:
- r is equal to 0 or 1,
- q is equal to 0, 1, 2 or 3,
- s is equal to 0, 1, 2, 3, 4 or 5,
- t is equal to 0, or 2,
- Y3═Y4 is C═C, C═N or N═N,
- if r=0, then X is O, S, NR18, CR20,
- if r=1, then X is CR20,
- R15 and R18, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen, halogen and sulfur atoms and an SO2 group, with the exception of the carbon atom connected to the nitrogen atom;
- wherein at least one of the radicals R15, an R18 does not comprise a peroxide bond or a diazo, nitro or nitroso radical,
- R16, R17, R19, R20 and R21, which may be identical or different, are each chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C10 hydrocarbonaceous chains which can form an optionally aromatic 5- to 7-membered carbonaceous ring;
- it being possible for at least one carbon atom of the hydrocarbonaceous chain to be replaced by at least one entity chosen from oxygen, nitrogen and sulfur atoms and a SO2 group;
- wherein at least one of the radicals R16, R17, R19, R20, and R21 does not comprise a peroxide bond or a diazo, nitro or nitroso radical, and
- V″ is an organic or inorganic anion,
- provided that in formula (I), one of the groups A1, Z2 and A3 is a cationic group.
Dependencies are inferred from the claim text.