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US 6,270,533 B1Granted
Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods
AssigneeL'oreal
InventorsAlain Genet, Alain Lagrange
Life of this patent
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Abstract
The invention relates to novel dibenzene oxidation bases containing at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring and aliphatic chains containing at least one quaternized unsaturated ring, to their use for the oxidation dyeing of keratin fibres, to dye compositions containing them and to oxidation dyeing processes using them.
Claims39
A compound of formula (I), or an acid addition salt thereof:
- wherein:
- B is a divalent linker arm which represents a group Z or an alkyl chain, said alkyl chain being uninterrupted or interrupted by at least one group Z and/or by at least one hetero atom, said alkyl chain being unsubstituted or substituted with at least one radical selected from hydroxyl and C1-C6 alkoxy radicals, said alkyl chain having no ketone functions or at least one ketone function;
- R1, R2, R3, R′1, R′2 and R′3, are identical or different and represent
- a divalent linker arm B,
- a hydrogen atom;
- a halogen atom;
- a group Z;
- a (C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl radical;
- an N-Z-amino(C1-C6)alkylcarbonyl radical;
- an N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N-Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- a carboxyl radical;
- a (C1-C6)alkylcarboxyl radical;
- a C1-C6 alkylsulphonyl radical;
- an aminosulphonyl radical;
- an N-Z-aminosulphonyl radical;
- a C1-C6 N-alkylaminosulphonyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N-Z-aminosulphonyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a carbamyl radical;
- an N-(C1-C6)alkylcarbamyl radical;
- an N,N-di(C1-C6)alkylcarbamyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a cyano radical;
- a group OR6
- a group SR6;
- an amino group protected with a (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, trifluoro(C1-C6)alkylcarbonyl, amino(C1-C6)alkylcarbonyl, N-Z-amino(C1-C6)alkylcarbonyl, N-(C1-C6)alkylamino(C1-C6)alkylcarbonyl, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl, carbamyl, N-(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C1-C6 N-alkylaminosulphonyl, N,N-di(C1-C6)alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
- R6 represents a divalent linker arm B,
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a group Z;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- a carboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N-Z-aminosulphonyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, N-(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, thiocarbamyl and C1-C6 alkylsulphonyl radicals, or with a group Z;
- A represents a group —NR4R5 or a hydroxyl radical;
- A′ represents a group —NR′4R′5 or a hydroxyl radical;
- R4, R5, R′4 and R′5, are identical or different and represent
- a divalent linker arm B,
- a hydrogen atom;
- a group Z;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a thiocarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a sulpho(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N-Z-aminosulphonyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, carbamyl, N-(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
- Z is selected from the unsaturated cationic groups of formulae (II) and (III) below, and the saturated cationic groups of formula (IV) below:
- wherein:
- D is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by at least one hetero atom, and said alkyl chain being unsubstituted or substituted with at least one hydroxyl or C1-C6 alkoxy radical, said alkyl chain having no ketone function or at least one ketone function;
- the ring members E, G, J, L and M, are identical or different and represent a carbon, oxygen, sulphur or nitrogen atom;
- n is an integer ranging from 0 to 4 inclusive;
- m is an integer ranging from 0 to 5 inclusive;
- the radicals R, are identical or different and represent
- a divalent linker arm B,
- a group Z,
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a (C1-C6)alkylcarbonyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical,
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- a group NHR″ or NR″R′″ wherein R″ and R′″ are identical or different and represent a C1-C6 alkyl radical, a monohydroxy(C1-C6)alkyl radical or a polyhydroxy(C2-C6)alkyl radical;
- R7 represents
- a divalent linker arm B,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a carbamyl(C1-C6)alkyl radical,
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical,
- a benzyl radical
- a group Z of formula (II), (III) or (IV) as defined above;
- R8, R9 and R10, are identical or different and represent
- a divalent linker arm B,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- an aryl radical,
- a benzyl radical,
- an amido(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical
- an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- two of the radicals R8, R9 and R10 may together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring, wherein said ring may contain at least one additional hetero atom, wherein said ring is unsubstituted or substituted with
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a keto(C1-C6)alkyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- one of the radicals R8, R9 and R10 may represent a second group Z which is identical to or different from the first group Z;
- R11 represents
- a divalent linker arm B,
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- an amino(C1-C6)alkyl radical,
- an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- a carboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical;
- a sulphonamido(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylketo(C1-C6)alkyl radical;
- an N-(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N-(C1-C6)alkylsulphonamido(C1-C6)alkyl radical;
- x and y are integers equal to 0 or 1;
- with the proviso that:
- in the unsaturated cationic group of formula (II):
- when x=0, the divalent linker arm D is attached to the nitrogen atom,
- when x=1, the divalent linker arm D is attached to one of the ring members E, G, J or L,
- y can take the value 1 only:
- 1) when the ring members E, G, J and L simultaneously represent a carbon atom and when the radical R7 is connected to the nitrogen atom of the unsaturated ring;
- or
- 2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the radical R7 is attached;
- in the unsaturated cationic group of formula (III):
- when x=0, the divalent linker arm D is attached to the nitrogen atom,
- when x=1, the divalent linker arm D is attached to one of the ring members E, G, J, L or M,
- y can take the value 1 only when at least one of the ring members E, G, J, L and M represents a divalent atom and when the radical R7 is connected to the nitrogen atom of the unsaturated ring;
- in the cationic group of formula (IV):
- when x=0, then the divalent linker arm is attached to the nitrogen atom bearing the radicals R8 to R10,
- when x=1, then two of the radicals R8 to R10 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the divalent linker arm D is connected to a carbon atom of said saturated ring;
- X− represents a monovalent or divalent anion;
- and further with the proviso that:
- the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1.
205 more elements
A process according to claim 36, wherein said oxidizing agent is selected from perborates and persulphates.
Dependencies are inferred from the claim text.