US 2006/0156490 A1 · Symmetrical diazo compounds comprising 2-imidazolium groups and a cationic linker, compositions comprising them, method of coloring, and device

Symmetrical cationic diazo compounds of formula (I) below, their resonance forms, and their acid addition salts and/or solvates:

in which formula:
the radicals R1, which are identical or not, represent:
an optionally substituted C1-C4 alkyl radical;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
the radicals R2, which are identical or not, represent:
an optionally substituted C1-C16 alkyl radical optionally interrupted by one or more heteroatoms and/or by one or more groups containing at least one heteroatom and selected preferably from oxygen, nitrogen, sulphur, —CO—, —SO2— or combinations thereof, said alkyl radical being further optionally substituted by one or more groups selected from thio (—SH), C1-C4 thioalkyl;
C1-C4 alkylsulphinyl or C1-C4 alkylsulphonyl groups;
a hydroxyl group,
a C1-C4 alkoxy group,
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R represents a C1-C4 alkyl radical,
an alkylcarbonyloxy radical (RCO—O—) in which R represents a C1-C4 alkyl radical,
an alkylcarbonyl radical (R—CO—) in which R represents a C1-C4 alkyl radical,
an amino group,
an amino group substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group, it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 to 2 heteroatoms, selected from N, O and S, preferably N, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
an alkylcarbonylamino group (RCO—NR′—) in which the radical R represents a C1-C4 alkyl radical and the radical R′ represents hydrogen or a C1-C4 alkyl radical;
an aminocarbonyl group ((R)2N—CO—) in which the radicals R independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′ independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an aminosulphonyl group ((R)2N—SO2—) in which the radicals R independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylsulphonylamino group (RSO2—NR′—) in which R represents a C1-C4 alkyl radical and R′ represents a hydrogen atom or a C1-C4 alkyl radical;
an optionally substituted aryl radical;
an optionally substituted (C1-C4)alkylaryl radical;
an alkylsulphinyl group (R—SO—) in which R represents a C1-C4 alkyl radical;
an alkylsulphonyl group (R—SO2—) in which R represents a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom, preferably chlorine or fluorine;
a thio group (HS—);
an alkylthio group (RS—) in which the radical R represents an optionally substituted C1-C4 alkyl radical;
when e is 2, the two radicals R2 may optionally form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 5 or 6 ring members, preferably 6 ring members, which is optionally substituted by one or more identical or non-identical groups selected from hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, amino substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group;
e is an integer from 0 to 2;
when e is less than 2, the unsubstituted carbon atom(s) of the heterocycle carry a hydrogen atom,
the radicals R3, which are identical or not, represent:
an optionally substituted C1-C16 alkyl radical optionally interrupted by one or more heteroatoms or by one or more groups containing at least one heteroatom and selected preferably from oxygen, nitrogen, sulphur, —CO—, —SO2— or combinations thereof,
a hydroxyl group,
a C1-C4 alkoxy group,
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl group (RO—CO—) in which R represents a C1-C4 alkyl radical,
an alkylcarbonyloxy radical (RCO—O—) in which R represents a C1-C4 alkyl radical;
an alkylcarbonyl radical (R—CO—) in which R represents a C1-C4 alkyl radical;
an amino group;
an amino group substituted by one or two identical or different C1-C4 alkyl radicals optionally carrying at least one hydroxyl group;
it being possible for the two alkyl radicals optionally to form, with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 to 2 heteroatoms, selected from N, O and S, preferably N, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
an alkylcarbonylamino group (RCO—NR′—) in which the radical R represents a C1-C4 alkyl radical and the radical R′ represents a hydrogen atom or a C1-C4 alkyl radical;
an aminocarbonyl group ((R)2N—CO—) in which the radicals R independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
a ureido group (N(R)2—CO—NR′—) in which the radicals R and R′ independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an aminosulphonyl group ((R)2N—SO2—) in which the radicals R independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylsulphonylamino group (RSO2—NR′—) in which the radicals R and R′ independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
a thio group (HS—);
an alkylthio group (RS—) in which the radical R represents a C1-C4 alkyl radical;
an alkylsulphinyl group (R—SO—) in which R represents a C1-C4 alkyl radical;
an alkylsulphonyl group (R—SO2—) in which R represents a C1-C4 alkyl radical;
a nitro group;
a cyano group;
a halogen atom, preferably chlorine or fluorine;
when m′ is greater than or equal to 2, two adjacent radicals R3 may form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic, containing 6 ring members, which is optionally substituted by one or more groups selected from the following groups:
hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, C2-C4 (poly)hydroxyalkoxy, C1-C4 alkylcarbonylamino, amino, amino substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group,
m′ is an integer from 0 to 4;
when m′ is less than 4, then the unsubstituted carbon atom(s) of the aromatic ring carry a hydrogen atom;
W1 radicals, which are identical, represent:
a hydrogen atom,
a halogen atom selected from bromine, chlorine and fluorine, preferably chlorine and fluorine,
an —NR5R6, OR7, —NR4—Ph—NR5R6, —NR4—Ph—OR7, —O—Ph—OR7 or —O—Ph—NR5R6 group, where:
R4 and R7, which are identical or not, represent a hydrogen atom, an optionally substituted C1-C20, preferably C1-C16, alkyl radical, an optionally substituted C1-C3 aralkyl radical or an optionally substituted phenyl radical;
R5 and R6, which are identical or not, represent a hydrogen atom, an optionally substituted C1-C20, preferably C1-C16, alkyl radical, an optionally substituted phenyl radical, an optionally substituted C1-C3 aralkyl radical or an alkylcarbonyl radical (R—CO—) in which R is a C1-C4 alkyl radical;
R5 and R6 may optionally form, with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 or 2 heteroatoms, selected from N, O and S, preferably N, and containing 5 to 7 ring members, which is saturated or unsaturated, aromatic or non-aromatic and is optionally substituted;
R5 and R6, independently of one another, may form, with the carbon atom of the aromatic ring adjacent to that to which —NR5R6 is attached, a 5- or 6-membered saturated heterocycle;
Ph represents an optionally substituted phenyl radical;
L, a cationic linker connecting the two identical azo chromophores, represents a C2-C40 alkyl radical which carries at least one cationic charge and is optionally substituted and/or optionally interrupted by one or more saturated or unsaturated, aromatic or non-aromatic, identical or different (hetero)cycles containing 3 to 7 ring members and/or optionally interrupted by one or more heteroatoms or groups containing at least one heteroatom, or combinations thereof, such as, for example, oxygen, nitrogen, sulphur, —CO—, —SO2— or combinations thereof, the linker L containing no azo, nitro, nitroso or peroxo bond;
with the proviso that the linker L carries at least one cationic charge;
the electroneutrality of the compound of formula (I) being ensured by one or more identical or non-identical, cosmetically acceptable anions An.

69 more elements

Compounds according to either of the preceding claims, characterized in that the radicals R2, which are identical or not, represent:

a halogen atom selected from chlorine and fluorine;
a C1-C4 alkyl radical optionally substituted by one or more identical or different radicals selected from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, thio (—SH), C1-C4 alkylsulphinyl, C1-C4 alkylsulphonyl and C1-C4 thioalkyl radicals;
a phenyl radical optionally substituted by one or more identical or different radicals selected from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino and C1-C2 (di)alkylamino radicals or a halogen atom such as chlorine or fluorine;
a C1-C4 alkoxy radical;
a C1-C4 alkylsulphonylamino radical;
a C2-C4 (poly)hydroxyalkoxy radical;
an amino radical;
a C1-C2 (di)alkylamino radical;
a C2-C4 (poly)hydroxyalkylamino radical;
an alkylsulphonylamino radical (RSO2N—) in which the radical R represents a C1-C4 alkyl radical;
an aminosulphonyl radical ((R)2NSO2—) in which the radicals R independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (RS—) in which the radical R represents a C1-C4 alkyl radical;
an alkylsulphinyl radical (RSO—) in which the radical R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (R—SO2—) in which the radical R represents a C1-C4 alkyl radical;
an alkylcarbonylamino radical (RCONR′—) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical and the radical R′ represents a hydrogen atom or a C1-C4 alkyl radical.

12 more elements

Compounds according to one of the preceding claims, characterized in that the radicals R3, which are identical or different, represent:

an optionally substituted C1-C16, preferably C1-C8 alkyl radical;
a halogen atom such as chlorine or fluorine;
a hydroxyl group;
a C1-C2 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy radical;
an amino radical;
an amino radical substituted by one or two identical or different C1-C4 alkyl radicals which optionally carry at least one hydroxyl group or at least one C1-C4 alkoxy radical, it being possible for the two alkyl radicals to form, with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 or 2 heteroatoms, selected from N, O and S, preferably N, the heterocycle containing 5 to 7 ring members, being saturated or unsaturated, aromatic or non-aromatic, and being optionally substituted;
an alkylcarbonylamino radical (RCO—NR′—) in which the radical R represents a C1-C4 alkyl radical and the radical R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (R′SO2—NR—) in which the radical R represents a hydrogen atom or a C1-C4 alkyl radical and the radical R′ represents a C1-C4 alkyl radical;
an aminosulphonyl radical ((R)2N—SO2—) in which the radicals R, which are identical or not, represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (RS—) in which the radical R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (R—SO2—) in which the radical R represents a C1-C4 alkyl radical.

9 more elements

Compounds according to one of the preceding claims, characterized in that L represents advantageously a C2-C20 alkyl radical:

1—interrupted by at least one group corresponding to the following formulae:
in which:
R9 and R10 independently of one another represent a C1-C8 alkyl radical;
a C1-C6 monohydroxyalkyl radical;
a C2-C6 polyhydroxyalkyl radical;
a C1-C6 alkoxy-C1-C6 alkyl radical;
an aryl radical such as phenyl which is optionally substituted;
an arylalkyl radical such as benzyl which is optionally substituted;
a C1-C6 aminoalkyl radical;
a C1-C6 aminoalkyl radical whose amine is substituted by one or more identical or different C1-C4 alkyl radicals, or C1-C6 alkylsulphonyl;
two radicals R9 may form, together with the nitrogen atom to which they are attached, an optionally substituted 5-, 6- or 7-membered saturated or unsaturated ring;
R13 radicals, which are identical or different, represent a halogen atom selected from bromine, chlorine and fluorine, a C1-C6 alkyl radical, a C1-C6 monohydroxyalkyl radical, a C2-C6 polyhydroxyalkyl radical, a C1-C6 alkoxy radical, a C1-C4 (di)alkylamino radical, a hydroxycarbonyl radical, a C1-C6 alkylcarbonyl radical, a C1-C6 thioalkyl radical, a C1-C6 alkylthio radical, an amino radical (di)substituted by a C1-C6 alkyl radical, C1-C6 alkylsulphonyl, a benzyl radical which is optionally substituted, or a phenyl radical which is optionally substituted by one or more radicals selected from methyl, hydroxyl, amino and methoxy radicals;
An is an organic or inorganic anion or anion mixture;
z is an integer between 1 and 3;
if z<3, the unsubstituted carbon atoms carry a hydrogen atom;
v is an integer 1 or 2, preferably 1;
2—optionally interrupted by one or more heteroatoms or groups containing at least one heteroatom, or combinations thereof, such as, for example, oxygen, nitrogen, sulphur, a —CO— group, a —SO2— group;
with the proviso that there is no nitro, nitroso or peroxo group or bond in the linker L;
3—and optionally substituted by one or more radicals selected from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, and amino radicals substituted by one or more linear or branched C1-C2 alkyl groups which optionally carry at least one hydroxyl group.

16 more elements

Symmetrical diazo compounds comprising 2-imidazolium groups and a cationic linker, compositions comprising them, method of coloring, and device

Life of this patent

Symmetrical diazo compounds comprising 2-imidazolium groups and a cationic linker, compositions comprising them, method of coloring, and device

Life of this patent

Abstract

Claims27