US 7,410,506 B2Granted

Dicationic bis-hydrazone compound, dye composition comprising at least one such compound, implementation process therefor and uses thereof

AssigneeL'oreal

InventorsHervé David, Andrew Greaves, Leïla Hercouet, Alain Lagrange

Life of this patent

Estimating the term…

Abstract

The present disclosure relates to a novel family of dicationic bis-hydrazone compounds that may be used as direct dyes, and to a dye composition for dyeing keratin fibers, for example, human keratin fibers such as the hair, comprising, in a suitable dyeing medium, at least one such compound. Also disclosed are dyeing processes implementing this composition and uses thereof.

Claims33

Dependent claims

A dicationic bis-hydrazone compound of formula (I)

DYE-L-DYE
in which each of the chromophores DYE, which may be identical or different, is chosen from chromophores of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) below:
wherein:
the groups R1 and R5, independently of each other, are chosen from linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chains, which can form one or more optionally substituted, optionally aromatic 3- to 7-membered carbon-based rings, the chains being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom,
the groups R2 and R3, independently of each other, are chosen from:
a halogen atom chosen from bromine, chlorine and fluorine;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form one or more optionally aromatic 3- to 6-membered carbon-based rings, the chain being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
a hydroxyl group;
a C1-C4 alkoxy group;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R is a C1-C4 alkyl radical;
or an alkylcarbonyloxy radical (RCO—O—) in which R is a C1-C4 alkyl radical;
an optionally substituted aryloxy group;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a carbamoyl group ((R)2N—CO—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a sulfonamide group ((R)2N—SO2—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylthio group (R—S—) in which the group R is a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom;
a trifluoromethyl group (CF3);
R1 and R2 may also form, with the nitrogen atom substituted with R1, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered heterocycle;
two adjacent radicals R2 may form, together with the carbon atoms to which they are attached, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
two adjacent radicals R3 can together form a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
the groups R4, independently of each other, are chosen from:
a hydrogen atom;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form at least one optionally aromatic 3- to 6-membered carbon-based ring, the chains being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
n is an integer from 0 to 5,
n′ is an integer from 0 to 4,
the bond a in formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) links each of the chromophores DYE to the linker L of formula (I),
X is an organic or mineral anion or mixture of anions for equilibrating the charge(s) of the compound Ia or Ib;
the group L is a linear or branched C1-C60 hydrocarbon-based chain that can form at least one optionally aromatic, optionally substituted 3- to 7-membered carbon-based ring, the chain being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom, L not comprising any peroxide, nitro, diazo or nitroso groups, the linker L being linked to the quaternized nitrogen atom of each of the chromophores DYE via a carbon atom, L not being cationic;
with the proviso that when the two chromophores DYE are identical and correspond to formula (Ia) with n=n′=0, then the group L is not one of the following groups:

37 more elements

A dye composition for dyeing keratin fibers, comprising, in a suitable dyeing medium, at least one dicationic bis-hydrazone compound of formula (I)

DYE-L-DYE
in which each of the chromophores DYE, which may be identical or different, is chosen from chromophores of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) below:
wherein:
the groups R1 and R5, independently of each other, are chosen from linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chains, which can form one or more optionally substituted, optionally aromatic 3- to 7-membered carbon-based rings, the chains being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom,
the groups R2 and R3, independently of each other, are chosen from:
a halogen atom chosen from bromine, chlorine and fluorine;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form one or more optionally aromatic 3- to 6-membered carbon-based rings, the chain being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
a hydroxyl group;
a C1-C4 alkoxy group;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R is a C1-C4 alkyl radical;
or an alkylcarbonyloxy radical (RCO—O—) in which R is a C1-C4 alkyl radical;
an optionally substituted aryloxy group;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a carbamoyl group ((R)2N—CO—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a sulfonamide group ((R)2N—SO2—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylthio group (R—S—) in which the group R is a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom;
a trifluoromethyl group (CF3);
R1 and R2 may also form, with the nitrogen atom substituted with R1, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered heterocycle;
two adjacent radicals R2 may form, together with the carbon atoms to which they are attached, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
two adjacent radicals R3 can together form a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
the groups R4, independently of each other, are chosen from:
a hydrogen atom;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form at least one optionally aromatic 3- to 6-membered carbon-based ring, the chains being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
n is an integer from 0 to 5,
n′ is an integer from 0 to 4,
the bond a in formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) links each of the chromophores DYE to the linker L of formula (I),
X is an organic or mineral anion or mixture of anions for equilibrating the charge(s) of the compound Ia or Ib;
the group L is a linear or branched C1-C60 hydrocarbon-based chain that can form at least one optionally aromatic, optionally substituted 3- to 7-membered carbon-based ring, the chain being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom, L not comprising any peroxide, nitro, diazo or nitroso groups, the linker L being linked to the quaternized nitrogen atom of each of the chromophores DYE via a carbon atom, L not being cationic;
with the proviso that when the two chromophores DYE are identical and correspond to formula (Ia) with n=n′=0, then the group L is not one of the following groups:

37 more elements

A process for dyeing keratin fibers, comprising applying a dye composition to keratin fibers and leaving it to act for a period sufficient to obtain a desired coloration, wherein said dye composition comprises, in a suitable dyeing medium, at least one dicationic bis-hydrazone compound of formula (I)

DYE-L-DYE
in which each of the chromophores DYE, which may be identical or different, is chosen from chromophores of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) below:
wherein:
the groups R1 and R5, independently of each other, are chosen from linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chains, which can form one or more optionally substituted, optionally aromatic 3- to 7-membered carbon-based rings, the chains being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom,
the groups R2 and R3, independently of each other, are chosen from:
a halogen atom chosen from bromine, chlorine and fluorine;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form one or more optionally aromatic 3- to 6-membered carbon-based rings, the chain being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
a hydroxyl group;
a C1-C4 alkoxy group;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R is a C1-C4 alkyl radical;
or an alkylcarbonyloxy radical (RCO—O—) in which R is a C1-C4 alkyl radical;
an optionally substituted aryloxy group;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a carbamoyl group ((R)2N—CO—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a sulfonamide group ((R)2N—SO2—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylthio group (R—S—) in which the group R is a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom;
a trifluoromethyl group (CF3);
R1 and R2 may also form, with the nitrogen atom substituted with R1, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered heterocycle;
two adjacent radicals R2 may form, together with the carbon atoms to which they are attached, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
two adjacent radicals R3 can together form a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
the groups R4, independently of each other, are chosen from:
a hydrogen atom;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form at least one optionally aromatic 3- to 6-membered carbon-based ring, the chains being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
n is an integer from 0 to 5,
n′ is an integer from 0 to 4,
the bond a in formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) links each of the chromophores DYE to the linker L of formula (I),
X is an organic or mineral anion or mixture of anions for equilibrating the charge(s) of the compound Ia or Ib;
the group L is a linear or branched C1-C60 hydrocarbon-based chain that can form at least one optionally aromatic, optionally substituted 3- to 7-membered carbon-based ring, the chain being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom, L not comprising any peroxide, nitro, diazo or nitroso groups, the linker L being linked to the quaternized nitrogen atom of each of the chromophores DYE via a carbon atom, L not being cationic;
with the proviso that when the two chromophores DYE are identical and correspond to formula (Ia) with n=n′=0, then the group L is not one of the following groups:

37 more elements

A process for obtaining dyeing results on keratin fibers that show good resistance to external agents and to shampoo, said process comprising applying to keratin fibers a dye composition comprising, in a suitable dyeing medium, at least one dicationic bis-hydrazone compound of formula (I)

DYE-L-DYE
in which each of the chromophores DYE, which may be identical or different, is chosen from chromophores of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) below:
wherein:
the groups R1 and R5, independently of each other, are chosen from linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chains, which can form one or more optionally substituted, optionally aromatic 3- to 7-membered carbon-based rings, the chains being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom,
the groups R2 and R3, independently of each other, are chosen from:
a halogen atom chosen from bromine, chlorine and fluorine;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form one or more optionally aromatic 3- to 6-membered carbon-based rings, the chain being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
a hydroxyl group;
a C1-C4 alkoxy group;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R is a C1-C4 alkyl radical;
or an alkylcarbonyloxy radical (RCO—O—) in which R is a C1-C4 alkyl radical;
an optionally substituted aryloxy group;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a carbamoyl group ((R)2N—CO—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a sulfonamide group ((R)2N—SO2—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylthio group (R—S—) in which the group R is a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom;
a trifluoromethyl group (CF3);
R1 and R2 may also form, with the nitrogen atom substituted with R1, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered heterocycle;
two adjacent radicals R2 may form, together with the carbon atoms to which they are attached, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
two adjacent radicals R3 can together form a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
the groups R4, independently of each other, are chosen from:
a hydrogen atom;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form at least one optionally aromatic 3- to 6-membered carbon-based ring, the chains being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
n is an integer from 0 to 5,
n′ is an integer from 0 to 4,
the bond a in formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) links each of the chromophores DYE to the linker L of formula (I),
X is an organic or mineral anion or mixture of anions for equilibrating the charge(s) of the compound Ia or Ib;
the group L is a linear or branched C1-C60 hydrocarbon-based chain that can form at least one optionally aromatic, optionally substituted 3- to 7-membered carbon-based ring, the chain being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom, L not comprising any peroxide, nitro, diazo or nitroso groups, the linker L being linked to the quaternized nitrogen atom of each of the chromophores DYE via a carbon atom, L not being cationic;
with the proviso that when the two chromophores DYE are identical and correspond to formula (Ia) with n=n′=0, then the group L is not one of the following groups:

37 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/249,370Filed 14 Oct 2005 · us provisional application
Priority: FR 04 1087014 Oct 2004
Published: US 2006/0096043 A111 May 2006
Granted: 12 Aug 2008
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

A61K 8/4946
With more than one nitrogen as the only hetero atom: imidazoles or their condensed derivatives, e.g. benzimidazoles
A61K 8/494
Containing heterocyclic compounds: with more than one nitrogen as the only hetero atom
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
A61Q 5/10
Preparations for care of the hair: preparations for permanently dyeing the hair

Family

Application60/627,158Us provisional application · filed 15 Nov 2004
US 2006/0096043 A1Pre-grant publication · published 11 May 2006
US 7,410,506 B2This patent

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

Timeline

Citations

Open elsewhere

Building an agent or pulling many patents? Use the API or MCP server instead of scraping pages. Get an API key

patentgrep

Loading patent…

Abstract

A dicationic bis-hydrazone compound of formula (I)

DYE-L-DYE
in which each of the chromophores DYE, which may be identical or different, is chosen from chromophores of formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) below:
wherein:
the groups R1 and R5, independently of each other, are chosen from linear or branched, saturated or unsaturated C1-C20 hydrocarbon-based chains, which can form one or more optionally substituted, optionally aromatic 3- to 7-membered carbon-based rings, the chains being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom,
the groups R2 and R3, independently of each other, are chosen from:
a halogen atom chosen from bromine, chlorine and fluorine;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form one or more optionally aromatic 3- to 6-membered carbon-based rings, the chain being optionally substituted or being optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
a hydroxyl group;
a C1-C4 alkoxy group;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R is a C1-C4 alkyl radical;
or an alkylcarbonyloxy radical (RCO—O—) in which R is a C1-C4 alkyl radical;
an optionally substituted aryloxy group;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a carbamoyl group ((R)2N—CO—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a sulfonamide group ((R)2N—SO2—) in which the radicals R, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylthio group (R—S—) in which the group R is a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom;
a trifluoromethyl group (CF3);
R1 and R2 may also form, with the nitrogen atom substituted with R1, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered heterocycle;
two adjacent radicals R2 may form, together with the carbon atoms to which they are attached, a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
two adjacent radicals R3 can together form a saturated or unsaturated, substituted or unsubstituted 5- or 6-membered aromatic ring or heterocycle;
the groups R4, independently of each other, are chosen from:
a hydrogen atom;
linear or branched, saturated or unsaturated C1-C16 hydrocarbon-based chains, which can form at least one optionally aromatic 3- to 6-membered carbon-based ring, the chains being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing at least one hetero atom;
an amino group, an amino group substituted with at least one C1-C4 alkyl radical, which may be identical or different, optionally bearing at least one hydroxyl group, the two alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- or 6-membered heterocycle, optionally bearing another nitrogen or non-nitrogen hetero atom;
an alkylcarbonylamino group (RCO—NR—) in which the radicals R, independently of each other, are chosen from C1-C4 alkyl radicals;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
an alkylsulfonylamino group (RSO2—NR′—) in which the radicals R and R′, independently of each other, are chosen from a hydrogen atom and a C1-C4 alkyl radical;
n is an integer from 0 to 5,
n′ is an integer from 0 to 4,
the bond a in formulae (Ia), (Ib), (Ic), (Id), (Ie), (If) and (Ig) links each of the chromophores DYE to the linker L of formula (I),
X is an organic or mineral anion or mixture of anions for equilibrating the charge(s) of the compound Ia or Ib;
the group L is a linear or branched C1-C60 hydrocarbon-based chain that can form at least one optionally aromatic, optionally substituted 3- to 7-membered carbon-based ring, the chain being optionally substituted, optionally interrupted with at least one hetero atom or with at least one group bearing a hetero atom, L not comprising any peroxide, nitro, diazo or nitroso groups, the linker L being linked to the quaternized nitrogen atom of each of the chromophores DYE via a carbon atom, L not being cationic;
with the proviso that when the two chromophores DYE are identical and correspond to formula (Ia) with n=n′=0, then the group L is not one of the following groups:

37 more elements

Facts

Application

11/249,370Filed 14 Oct 2005 · us provisional application

Priority

FR 04 1087014 Oct 2004

Published

US 2006/0096043 A111 May 2006

Granted

12 Aug 2008

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

A61K 8/4946
With more than one nitrogen as the only hetero atom: imidazoles or their condensed derivatives, e.g. benzimidazoles
A61K 8/494
Containing heterocyclic compounds: with more than one nitrogen as the only hetero atom
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
A61Q 5/10
Preparations for care of the hair: preparations for permanently dyeing the hair