US 8,012,220 B2Granted

Specific monocationic monochromophoric compounds of hydrazone type comprising a 2-, 4-pyridinium or 2-, 4-quinolinium unit, synthesis thereof, dye compositions containing them, and method for dyeing keratin fibres

AssigneeL'oreal

InventorsHervé David, Nadège Murguet, Andrew Greaves

Life of this patent

Estimating the term…

Abstract

The present disclosure relates to monocationic monochromophoric compounds of formula (I) and (II) and dyeing compositions and multicompartment devices comprising monocationic monochromophoric compounds of formula (I) and (II). The disclosure also relates to methods for preparing monocationic monochromophoric compounds of formula (I) and (II), and also to methods for dyeing comprising applying monocationic monochromophoric compounds of formula (I) and (II) to keratin fibers.

Claims10

Dependent claims

At least one monocationic monochromophoric entity comprising one hydrazone entity, wherein the at least one monocationic monocromophoric entity comprising one hydrazone entity is chosen from those of formulae (I) and (II):

the mesomeric forms, addition salts with an acid, and solvates thereof:
wherein:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—)wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl) aminosulphonyl radical ((R2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl (C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
wherein the R2, R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom chosen from chlorine and fluorine;
a C1-C8 alkyl radical optionally substituted by at least one group chosen from hydroxyl, ((di)alkyl)amino, and sulphonylamino groups, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a (C1-C4)alkoxycarbonyl radical;
an optionally substituted aryloxy radical;
an amino radical optionally substituted:
by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group;
or
by one or two phenyl, aminophenyl or methoxyphenyl radicals;
a (C1-C4)alkylcarbonylamino radical wherein the amino functional group may or may not be substituted by a C1-C4 alkyl radical;
an aminocarbonyl radical;
an aminosulphonyl, (di)(C1-C4)alkylaminosulphonyl radical;
a (C1-C4)alkylthio radical;
a phenyl radical;
a trifluoromethyl radical;
or
a thio radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C 4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionall substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which the are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 1 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 1 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

72 more elements

A dyeing composition comprising, as direct dye, in a medium suitable for dyeing keratin fibers, at least one monocationic monochromophoric entity comprising one hydrazone entity, wherein the at least one monocationic monochromophoric entity comprising one hydrazone entity is chosen from those of formulae (I) and (II):

the mesomeric forms, addition salts with an acid, and solvates thereof:
wherein:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C 4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C-1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic(hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C 4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 0 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 0 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

78 more elements

A method for dyeing keratin fibres comprising:

applying to the keratin fibers, at least one composition comprising at least one monocationic monochromophoric entity comprising one hydrazone entity, wherein the monocationic monochromophoric entity comprising one hydrazone entity is chosen from those of formulae (I) and (II):
the mesomeric forms, addition salts with an acid, and solvates thereof:
wherein:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 0 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 0 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different,
wherein the keratin fibers can be either dry or wet fibers, and
leaving the at least one composition on the keratin fibers for a sufficient time to obtain the desired effect.

81 more elements

A multicompartment device comprising at least one first compartment comprising at least one monocationic monochromophoric entity comprising one hydrazone entity, wherein the monocationic monochromophoric entity comprising one hydrazone entity is chosen from those of formulae (I) and (II):

the mesomeric forms, addition salts with an acid, and solvates thereof:
wherein:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 0 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 0 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different;
and at least one second compartment comprising at least one oxidizing agent.

79 more elements

A method for preparing at least one monocationic monochromophoric entity comprising one hydrazone entity, wherein the at least one monocationic monochromophoric entity comprising one hydrazone entity is chosen from those of formulae (I) and (II)

the mesomeric forms, addition salts with an acid, and/or solvates thereof:
comprising
(a) Condensing a heteroaromatic aldehyde or ketone with a hydrazine derivative according to the following reaction:
and
(b) Quaternizing the heterocyclic ring of formula (V) according to the following reaction:
wherein, in formulae I and II:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 1 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 1 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

82 more elements

the mesomeric forms, addition salts with an acid, and/or solvates thereof, comprising:
(a) Condensing a heteroaromatic aldehyde or ketone with a hydrazine derivative according to the following reaction:
(b) Quaternizing the heterocyclic ring of formula (VIII) according to the following reaction:
(c) Aminating formula (IX) according to the following reaction:
and (d) Alkylating formula (X) or (XI) according to the following reaction:
wherein, in formulae I and II:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 0 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 1 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

82 more elements

the mesomeric forms, addition salts with an acid, and/or solvates thereof, comprising:
(a) quaternizing formula (XII) according to the following reaction:
(b) coupling a diazonium salt to formula (XIII) according to the following reaction:
and
(c) alkylating formula (X) or (XI) according to the following reaction:
wherein, in formula I and II:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—) wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl(C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R2 and R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one groups comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a C2-C4 (poly)hydroxyalkoxy group;
an alkoxycarbonyl radical (RO—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylcarbonyloxy radical (RCO—O) wherein R represents a C1-C4 alkyl radical;
an optionally substituted aryloxy radical;
an optionally substituted (di)arylamino radical;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, optionally aromatic heterocycle having 5 or 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminocarbonyl group ((R)2N—CO—) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminosulphonyl radical ((R)2N—SO2—) wherein the R radicals, independently of one another represent a hydrogen atom or a C1-C4 alkyl radical;
an alkylthio radical (R—S—) wherein the R radical represents a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and the R′ radical represents a hydrogen atom or a C1-C4 alkyl radical;
a cyano radical (—C≡N);
a phenyl radical;
a trifluoromethyl radical (—CF3);
a thio (—SH) radical;
an alkylsulphinyl radical (RSO—) wherein the R radical represents a C1-C4 alkyl radical;
or
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionally substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which they are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 1 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 1 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

82 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/296,721Filed 13 Apr 2007 · us provisional application
Priority: FR 06 0332213 Apr 2006
Published: US 2009/0300856 A110 Dec 2009
Granted: 6 Sep 2011
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 213/53
Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom: nitrogen atoms
A61K 8/4926
With one nitrogen as the only hetero atom: having six membered rings
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
C07D 215/12
Having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring…:…

Family

Application60/796,516Us provisional application · filed 2 May 2006
US 2009/0300856 A1Pre-grant publication · published 10 Dec 2009
US 8,012,220 B2This patent

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

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Abstract

the mesomeric forms, addition salts with an acid, and solvates thereof:
wherein:
the R1 radicals, which may be identical or different, represent, independently of one another:
a hydrogen;
an optionally substituted C1-C20 alkyl radical optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an optionally substituted phenyl radical;
an optionally substituted benzyl radical;
an alkylcarbonyl radical (R—CO—) wherein R represents a C1-C4 alkyl radical;
an alkylsulphonyl radical (RSO2—)wherein R represents a C1-C4 alkyl radical;
an arylsulphonyl radical (R′SO2—) wherein R′ represents an optionally substituted phenyl or benzyl radical;
a (di)(alkyl) aminosulphonyl radical ((R2N—SO2—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
or
a (di)(alkyl)aminocarbonyl radical ((R)2N—CO—) wherein the R radicals independently represent a hydrogen or a C1-C4 alkyl radical;
the R5 radicals, which may be identical or different, represent, independently of one another:
an optionally substituted C1-C20 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
a trimethylsilyl (C1-C4)alkyl radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
wherein the R2, R3 radicals, which may be identical or different, represent, independently of one another:
a halogen atom chosen from chlorine and fluorine;
a C1-C8 alkyl radical optionally substituted by at least one group chosen from hydroxyl, ((di)alkyl)amino, and sulphonylamino groups, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
a hydroxyl radical;
a C1-C4 alkoxy radical;
a (C1-C4)alkoxycarbonyl radical;
an optionally substituted aryloxy radical;
an amino radical optionally substituted:
by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group;
or
by one or two phenyl, aminophenyl or methoxyphenyl radicals;
a (C1-C4)alkylcarbonylamino radical wherein the amino functional group may or may not be substituted by a C1-C4 alkyl radical;
an aminocarbonyl radical;
an aminosulphonyl, (di)(C1-C4)alkylaminosulphonyl radical;
a (C1-C4)alkylthio radical;
a phenyl radical;
a trifluoromethyl radical;
or
a thio radical;
wherein R1 can form with an R2 radical located in the ortho position with respect to the NR1 group and with the nitrogen atom substituted by R1, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein two adjacent R2 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted, aromatic or non-aromatic (hetero)cyclic radical comprising 5 or 6 ring members;
wherein two adjacent R3 radicals can form, with one another and with the carbon atoms to which they are attached, a substituted or unsubstituted aromatic ring comprising 5 or 6 ring members;
the R4 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatom and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an amino radical optionally substituted by one or two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl or C1-C2 alkoxy group, it being possible for said alkyl radicals to optionally form, with the nitrogen atom to which they are attached, a saturated or unsaturated or aromatic, optionally substituted heterocycle having 5 or 6 ring members, optionally comprising at least one other heteroatom which may be identical to or different from nitrogen;
an alkylcarbonylamino radical (RCO—NR′—) wherein the R radical represents a C1-C 4 alkyl radical and R′ represents a hydrogen or a C1-C4 alkyl radical;
a ureido radical (N(R)2—CO—NR′—) wherein the R radicals, independently of one another, represent a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
an alkylsulphonylamino radical (RSO2—NR′—) wherein the R radical represents a C1-C4 alkyl radical, and R′ represents a hydrogen or a C1-C4 alkyl radical;
a hydroxycarbonyl radical;
a C1-C4 alkoxycarbonyl radical;
a cyano radical;
an optionally substituted phenyl radical;
or
an optionally substituted benzyl radical;
the R6 and R7 radicals, which may be identical or different, represent, independently of one another:
a hydrogen atom;
an optionally substituted C1-C16 alkyl radical, optionally interrupted by at least one heteroatoms and/or by at least one group comprising at least one heteroatom;
with the proviso that the alkyl radical does not comprise any nitro, nitroso, peroxo or diazo functional groups;
an (alkoxy)aryl radical (-Ph-OR) wherein the R radical represents a hydrogen or a C1-C4 alkyl radical;
a (di)(alkyl)aminoaryl radical (-Ph-N(R)2) wherein the R radicals, independently of one another, represent a hydrogen or a C1-C4 alkyl radical optionall substituted by a hydroxyl;
an alkylsulphonyl radical (RSO2—) wherein the R radical represents a C1-C4 alkyl radical;
an aminocarbonyl radical, a (di)(C1-C4)alkylaminocarbonyl radical;
a CH3CO— radical;
a phenyl;
or
a benzyl optionally substituted by at least one hydroxyl and/or amino group;
wherein the R6 and R7 radicals can optionally form with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted heterocycle comprising from 5 to 7 ring members, optionally comprising another heteroatom which may be identical to or different from nitrogen;
wherein one of the R6 or R7 radicals can also form with the nitrogen atom to which it is attached and with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
wherein the R6 and R7 radicals can form with the nitrogen atom to which the are attached and each with an R2 radical located in the ortho position with respect to the NR6R7 group, a substituted or unsubstituted, saturated or unsaturated heterocycle comprising 5 or 6 ring members;
n is an integer ranging from 1 to 4, wherein when n is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
n′ is an integer ranging from 1 to 4, wherein when n′ is below 4, the unsubstituted carbon atom or atoms bear(s) a hydrogen atom;
the electroneutrality of the compounds of formulae (I) and/or (II) being ensured by at least one cosmetically acceptable anion An, which may be identical or different.

72 more elements

Facts

Application

12/296,721Filed 13 Apr 2007 · us provisional application

Priority

FR 06 0332213 Apr 2006

Published

US 2009/0300856 A110 Dec 2009

Granted

6 Sep 2011

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 213/53
Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom: nitrogen atoms
A61K 8/4926
With one nitrogen as the only hetero atom: having six membered rings
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
C07D 215/12
Having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring…:…