US 7,077,873 B2Granted

Composition for the dyeing of human keratinous fibres comprising a monocationic monoazo dye

AssigneeL'oreal

InventorsHervé David, Nathalie Berteuil, Laurent Vidal

Life of this patent

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Abstract

A subject-matter of the disclosure is a novel composition for the dyeing of human keratinous fibres, for example, the hair, comprising a monocationic monoazo dye of formula (I) W1-N═N—W2-NW3-W4-W5, the dyeing processes employing it, the use of the dyes of formula (I) as direct dyes and the novel compounds of formula (I).

Claims47

Dependent claims

A composition for dyeing human keratinous fibres comprising, in a cosmetically acceptable medium, at least one monocationic monoazo dye of formula (I):

W1—N═N═W2—NW3—W4—W5 (I)
wherein:
W1 is chosen from 5- and 6-membered cationic aromatic heterocycles of formulae (II) and (III):
wherein:
Z1 is chosen from an oxygen atom, a sulphur atom, NR2 radicals, and CR3 radicals,
Z2 is chosen from a nitrogen atom and CR4 radicals,
Z3 is chosen from NR12 radicals and CR13 radicals,
Z4 is chosen from a nitrogen atom and CR14 radicals,
Z5 is chosen from a nitrogen atom and CR15 radicals,
with the proviso that formulae (II) and (III) do not comprise more than two adjacent heteroatoms;
the bond a connects the 5-membered cationic ring of formula (II) to the azo functional group of formula (I),
the bond b connects the 6-membered cationic ring of formula (III) to the azo functional group of formula (I),
X− is chosen from organic and inorganic anions,
W2 and W4 (formula I), which may be identical or different, are chosen from divalent carbonaceous aromatic groups and pyridine groups of formulae (IV) and (V):
W3 is chosen from a hydrogen atom and C1-C6 alkyl radicals that may be optionally substituted with at least one radical chosen from hydroxyl radicals, alkoxy radicals, amino radicals, mono(C1-C4)alkylamino radicals, and di(C1-C4)alkylamino radicals,
W5 is a 5-membered nitrogenous heteroaromatic radical connected to W4 via the nitrogen atom of the ring of the said heteroaromatic radical, wherein the heteroaromatic radical is chosen from pyrazolyl, pyrrolyl, imidazolyl, triazolyl, and thiadiazolyl radicals, it being possible for each of these heteroaromatic radicals to be substituted by at least one entity chosen from hydrogen, chlorine, and fluorine atoms, C1-C6 alkyl radicals optionally substituted by at least one radical chosen from hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, (di)(C1-C4)alkylamino, C2-C4 (poly)hydroxyalkylamino, carboxyl, sulpho, C1-C4 alkoxycarbonyl, and C1-C4 alkylthio radicals;
and at least one phenyl radical, which may be optionally substituted by at least one entity chosen from halogen atoms and hydroxyl, C1-C2 alkoxy, amino, (di)(C1-C2)alkylamino, carboxyl, sulpho, C1-C4 alkyl, and C1-C2 alkylthio radicals,
R1, R2, R9 and R12, which may be identical or different, are chosen from phenyl radicals that may be optionally substituted and C1-C8 alkyl radicals that may be optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and (di)(C1-C2)alkylamino radicals,
R5, R6, R7 and R8, which may be identical or different, are chosen from a hydrogen atom;
a chlorine atom;
a bromine atom;
linear and branched, saturated and unsaturated C1-C8 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, at least one carbon atom of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R5, R6, R7 and R8 do not comprise a peroxide bond or a diazo or nitroso radical,
R3, R4, R10, R11, R13, R14 and R15, which may be identical or different, are chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C16 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, one or more carbon atoms of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms, and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R3, R4, R10, R11, R13, R14 and R15 do not comprise a peroxide bond or a diazo or nitroso radical,
R4 with R13 and R14 with R15 can form a carbonaceous aromatic ring.

23 more elements

A process for the direct dyeing of human keratinous fibres, comprising applying to the fibres a dyeing composition comprising, in a cosmetically acceptable medium,

at least one monocationic monoazo dye of formula (I):
W1—N═N—W2—NW3—W4—W5 (I)
wherein:
W1 is chosen from 5- and 6-membered cationic aromatic heterocycles of formulae (II) and (III):
wherein:
Z1 is chosen from an oxygen atom, a sulphur atom, NR2 radicals, and CR3 radicals,
Z2 is chosen from a nitrogen atom and CR4 radicals,
Z3 is chosen from NR12 radicals and CR13 radicals,
Z4 is chosen from a nitrogen atom and CR14 radicals,
Z5 is chosen from a nitrogen atom and CR15 radicals,
with the proviso that formulae (II) and (III) do not comprise more than two adjacent heteroatoms;
the bond a connects the 5-membered cationic ring of formula (II) to the azo functional group of formula (I),
the bond b connects the 6-membered cationic ring of formula (III) to the azo functional group of formula (I),
X− is chosen from organic and inorganic anions,
W2 and W4 (formula I), which may be identical or different, are chosen from divalent carbonaceous aromatic groups and pyridine groups of formulae (IV) and (V):
W3 is chosen from a hydrogen atom and C1-C6 alkyl radicals that may be optionally substituted with at least one radical chosen from hydroxyl radicals, alkoxy radicals, amino radicals, mono(C1-C4)alkylamino radicals, and di(C1-C4)alkylamino radicals,
W5 is a 5-membered nitrogenous heteroaromatic radical connected to W4 via the nitrogen atom of the ring of the said heteroaromatic radical, wherein the heteroaromatic radicals are chosen from pyrazolyl, pyrrolyl, imidazolyl, triazolyl, and thiadiazolyl radicals, it being possible for each of these heteroaromatic radicals to be substituted by at least one entity chosen from hydrogen, chlorine, and fluorine atoms, C1-C6 alkyl radicals optionally substituted by at least one radical chosen from hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, (di)(C1-C4)alkylamino, C2-C4 (poly)hydroxyalkylamino, carboxyl, sulpho, C1-C4 alkoxycarbonyl, and C1-C4 alkylthio radicals;
and at least one phenyl radical, which may be optionally substituted by at least one entity chosen from halogen atoms and hydroxyl, C1-C2 alkoxy, amino, (di)(C1-C2)alkylamino, carboxyl, sulpho, C1-C4 alkyl, and C1-C2 alkylthio radicals,
R1, R2, R9 and R12, which may be identical or different, are chosen from phenyl radicals that may be optionally substituted and C1-C8 alkyl radicals that may be optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and (di)(C1-C2)alkylamino radicals,
R5, R6, R7 and R8, which may be identical or different, are chosen from a hydrogen atom;
a chlorine atom;
a bromine atom;
linear and branched, saturated and unsaturated C1-C8 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, at least one carbon atom of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R5, R6, R7 and R8 do not comprise a peroxide bond or a diazo or nitroso radical,
R3, R4, R10, R11, R13, R14 and R15, which may be identical or different, are chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C16 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, one or more carbon atoms of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms, and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R3, R4, R10, R11, R13, R14 and R15 do not comprise a peroxide bond or diazo or nitroso radicals,
R4 with R13 and R14 with R15 can form a carbonaceous aromatic ring.

24 more elements

A monocationic monoazo compound chosen from compounds of formula (I):

W1—N═N—W2—NW3—W4—W5 (I)
wherein:
W1 is chosen from 5- and 6-membered cationic aromatic heterocycles of formulae (II) and (III):
wherein:
Z1 is chosen from an oxygen atom, a sulphur atom, NR2 radicals, and CR3 radicals,
Z2 is chosen from a nitrogen atom and CR4 radicals,
Z3 is chosen from NR12 radicals and CR13 radicals,
Z4 is chosen from a nitrogen atom and CR14 radicals,
Z5 is chosen from a nitrogen atom and CR15 radicals,
with the proviso that formulae (II) and (III) do not comprise more than two adjacent heteroatoms;
the bond a connects the 5-membered cationic ring of formula (II) to the azo functional group of formula (I),
the bond b connects the 6-membered cationic ring of formula (III) to the azo functional group of formula (I),
X− is chosen from organic and inorganic anions,
W2 and W4 (formula I), which may be identical or different, are chosen from divalent carbonaceous aromatic groups and pyridine groups of formulae (IV) and (V):
W3 is chosen from a hydrogen atom and C1-C6 alkyl radicals that may be optionally substituted with at least one radical chosen from hydroxyl radicals, alkoxy radicals, amino radicals, mono(C1-C4)alkylamino radicals, and di(C1-C4)alkylamino radicals,
W5 is a 5-membered nitrogenous heteroaromatic radical connected to W4 via the nitrogen atom of the ring of the said heteroaromatic radical, wherein the heteroaromatic radicals are chosen from pyrazolyl, pyrrolyl, imidazolyl, triazolyl, and thiadiazolyl radicals, it being possible for each of these heteroaromatic radicals to be substituted by at least one entity chosen from hydrogen, chlorine, and fluorine atoms, C1-C6 alkyl radicals optionally substituted by at least one radical chosen from hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, (di)(C1-C4)alkylamino, C2-C4 (poly)hydroxyalkylamino, carboxyl, sulpho, C1-C4 alkoxycarbonyl, and C1-C4 alkylthio radicals;
and at least one phenyl radical, which may be optionally substituted by at least one entity chosen from halogen atoms and hydroxyl, C1-C2 alkoxy, amino, (di)(C1-C2)alkylamino, carboxyl, sulpho, C1-C4 alkyl, and C1-C2 alkylthio radicals,
R1, R2, R9 and R12, which may be identical or different, are chosen from phenyl radicals that may be optionally substituted and C1-C8 alkyl radicals that may be optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and (di)(C1-C2)alkylamino radicals,
R5, R6, R7 and R8, which may be identical or different, are chosen from a hydrogen atom;
a chlorine atom;
a bromine atom;
linear and branched, saturated and unsaturated C1-C8 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, at least one carbon atom of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R5, R6, R7 and R8 do not comprise a peroxide bond or a diazo or nitroso radical,
R3, R4, R10, R11, R13, R14 and R15, which may be identical or different, are chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C16 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, one or more carbon atoms of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms, and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R3, R4, R10, R11, R13, R14 and R15 do not comprise a peroxide bond or diazo or nitroso radicals,
R4 with R13 and R14 with R15 can form a carbonaceous aromatic ring.

23 more elements

A multi-compartment kit or device for the dyeing of human keratinous fibres, comprising:

at least one first compartment comprises a composition comprising, in a cosmetically acceptable medium,
at least one monocationic monoazo dye of formula (I):
W1—N═N—W2—NW3—W4—W5 (I)
wherein:
W1 is chosen from 5- and 6-membered cationic aromatic heterocycles of formulae (II) and (III):
wherein:
Z1 is chosen from an oxygen atom, a sulphur atom, NR2 radicals, and CR3 radicals,
Z2 is chosen from a nitrogen atom and CR4 radicals,
Z3 is chosen from NR12 radicals and CR13 radicals,
Z4 is chosen from a nitrogen atom and CR14 radicals,
Z5 is chosen from a nitrogen atom and CR15 radicals,
with the proviso that formulae (II) and (III) do not comprise more than two adjacent heteroatoms;
the bond a connects the 5-membered cationic ring of formula (II) to the azo functional group of formula (I),
the bond b connects the 6-membered cationic ring of formula (III) to the azo functional group of formula (I),
X− is chosen from organic and inorganic anions,
W2 and W4 (formula I), which may be identical or different, are chosen from divalent carbonaceous aromatic groups and pyridine groups of formulae (IV) and (V):
W3 is chosen from a hydrogen atom and C1-C6 alkyl radicals that may be optionally substituted with at least one radical chosen from hydroxyl radicals, alkoxy radicals, amino radicals, mono(C1-C4)alkylamino radicals, and di(C1-C4)alkylamino radicals,
W5 is a 5-membered nitrogenous heteroaromatic radical connected to W4 via the nitrogen atom of the ring of the said heteroaromatic radical, wherein the heteroaromatic radicals are chosen from pyrazolyl, pyrrolyl, imidazolyl, triazolyl, and thiadiazolyl radicals, it being possible for each of these heteroaromatic radicals to be substituted by at least one entity chosen from hydrogen, chlorine, and fluorine atoms, C1-C6 alkyl radicals optionally substituted by at least one radical chosen from hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, (di)(C1-C4)alkylamino, C2-C4 (poly)hydroxyalkylamino, carboxyl, sulpho, C1-C4 alkoxycarbonyl, and C1-C4 alkylthio radicals;
and at least one phenyl radical, which may be optionally substituted by at least one entity chosen from halogen atoms and hydroxyl, C1-C2 alkoxy, amino, (di)(C1-C2)alkylamino, carboxyl, sulpho, C1-C4 alkyl, and C1-C2 alkylthio radicals,
R1, R2, R9 and R12, which may be identical or different, are chosen from phenyl radicals that may be optionally substituted and C1-C8 alkyl radicals that may be optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and (di)(C1-C2)alkylamino radicals,
R5, R6, R7 and R8, which may be identical or different, are chosen from a hydrogen atom;
a chlorine atom;
a bromine atom;
linear and branched, saturated and unsaturated C1-C8 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, at least one carbon atom of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R5, R6, R7 and R8 do not comprise a peroxide bond or a diazo or nitroso radical,
R3, R4, R10, R11, R13, R14 and R15, which may be identical or different, are chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C16 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, one or more carbon atoms of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms, and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R3, R4, R10, R11, R13, R14 and R15 do not comprise a peroxide bond or a diazo or nitroso radical,
R4 with R13 and R14 with R15 can form a carbonaceous aromatic ring;
and
at least one second compartment comprises at least one oxidizing composition.

27 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/658,409Filed 10 Sep 2003 · us provisional application
Priority: FR 02 1118610 Sep 2002
Published: US 2004/0127692 A11 Jul 2004
Granted: 18 Jul 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 8/4946
With more than one nitrogen as the only hetero atom: imidazoles or their condensed derivatives, e.g. benzimidazoles
A61Q 5/065
Preparations for styling the hair, e.g. by temporary shaping or colouring: preparations for temporary colouring the hair, e.g. direct dyes
C09B 44/126
Having one nitrogen atom as the only ring hetero atom: in a six-membered ring, e.g. pyrridinium, quinolinium
C09B 44/16
Containing cyclammonium groups attached to an azo group by a carbon atom of the ring system: 1,3-Diazoles or hydrogenated 1,3-diazoles ; imidazolium

Family

Application60/410,311Us provisional application · filed 13 Sep 2002
US 2004/0127692 A1Pre-grant publication · published 1 Jul 2004
US 7,077,873 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A composition for dyeing human keratinous fibres comprising, in a cosmetically acceptable medium, at least one monocationic monoazo dye of formula (I):

W1—N═N═W2—NW3—W4—W5 (I)
wherein:
W1 is chosen from 5- and 6-membered cationic aromatic heterocycles of formulae (II) and (III):
wherein:
Z1 is chosen from an oxygen atom, a sulphur atom, NR2 radicals, and CR3 radicals,
Z2 is chosen from a nitrogen atom and CR4 radicals,
Z3 is chosen from NR12 radicals and CR13 radicals,
Z4 is chosen from a nitrogen atom and CR14 radicals,
Z5 is chosen from a nitrogen atom and CR15 radicals,
with the proviso that formulae (II) and (III) do not comprise more than two adjacent heteroatoms;
the bond a connects the 5-membered cationic ring of formula (II) to the azo functional group of formula (I),
the bond b connects the 6-membered cationic ring of formula (III) to the azo functional group of formula (I),
X− is chosen from organic and inorganic anions,
W2 and W4 (formula I), which may be identical or different, are chosen from divalent carbonaceous aromatic groups and pyridine groups of formulae (IV) and (V):
W3 is chosen from a hydrogen atom and C1-C6 alkyl radicals that may be optionally substituted with at least one radical chosen from hydroxyl radicals, alkoxy radicals, amino radicals, mono(C1-C4)alkylamino radicals, and di(C1-C4)alkylamino radicals,
W5 is a 5-membered nitrogenous heteroaromatic radical connected to W4 via the nitrogen atom of the ring of the said heteroaromatic radical, wherein the heteroaromatic radical is chosen from pyrazolyl, pyrrolyl, imidazolyl, triazolyl, and thiadiazolyl radicals, it being possible for each of these heteroaromatic radicals to be substituted by at least one entity chosen from hydrogen, chlorine, and fluorine atoms, C1-C6 alkyl radicals optionally substituted by at least one radical chosen from hydroxyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, (di)(C1-C4)alkylamino, C2-C4 (poly)hydroxyalkylamino, carboxyl, sulpho, C1-C4 alkoxycarbonyl, and C1-C4 alkylthio radicals;
and at least one phenyl radical, which may be optionally substituted by at least one entity chosen from halogen atoms and hydroxyl, C1-C2 alkoxy, amino, (di)(C1-C2)alkylamino, carboxyl, sulpho, C1-C4 alkyl, and C1-C2 alkylthio radicals,
R1, R2, R9 and R12, which may be identical or different, are chosen from phenyl radicals that may be optionally substituted and C1-C8 alkyl radicals that may be optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and (di)(C1-C2)alkylamino radicals,
R5, R6, R7 and R8, which may be identical or different, are chosen from a hydrogen atom;
a chlorine atom;
a bromine atom;
linear and branched, saturated and unsaturated C1-C8 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, at least one carbon atom of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R5, R6, R7 and R8 do not comprise a peroxide bond or a diazo or nitroso radical,
R3, R4, R10, R11, R13, R14 and R15, which may be identical or different, are chosen from a hydrogen atom and linear and branched, saturated and unsaturated C1-C16 hydrocarbonaceous chains that can form at least one 3- to 6-membered carbonaceous ring, one or more carbon atoms of the carbonaceous chain of which can be replaced by at least one entity chosen from oxygen, nitrogen, and sulphur atoms, and SO2 groups, and the carbon atoms of which can, independently of one another, be substituted by at least one halogen atom;
with the proviso that R3, R4, R10, R11, R13, R14 and R15 do not comprise a peroxide bond or a diazo or nitroso radical,
R4 with R13 and R14 with R15 can form a carbonaceous aromatic ring.

23 more elements

Facts

Application

10/658,409Filed 10 Sep 2003 · us provisional application

Priority

FR 02 1118610 Sep 2002

Published

US 2004/0127692 A11 Jul 2004

Granted

18 Jul 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61K 8/4946
With more than one nitrogen as the only hetero atom: imidazoles or their condensed derivatives, e.g. benzimidazoles
A61Q 5/065
Preparations for styling the hair, e.g. by temporary shaping or colouring: preparations for temporary colouring the hair, e.g. direct dyes
C09B 44/126
Having one nitrogen atom as the only ring hetero atom: in a six-membered ring, e.g. pyrridinium, quinolinium
C09B 44/16
Containing cyclammonium groups attached to an azo group by a carbon atom of the ring system: 1,3-Diazoles or hydrogenated 1,3-diazoles ; imidazolium