Dye composition comprising a cationic para-aminophenol oxidation base

Abstract

The present invention relates to a para-aminophenol compound of formula (I), the addition salts thereof with an acid and the solvates thereof: in which: R represents a hydrogen or halogen atom; a C 1 -C 4 alkyl radical; a carboxyl radical or a (C 1 -C 4 )alkoxycarbonyl radical; Z1 is an oxygen atom or a group NR2; R2 is a hydrogen atom or a linear or branched C 1 -C 4 alkyl radical, a benzyl radical or an acetyl radical; R1 is a saturated, linear or branched C 1 -C 10 alkyl radical, which is substituted with or interrupted by a cationic radical, optionally interrupted by one or more oxygen atoms and/or by one or more groups NR2, optionally substituted with one or more radicals chosen from hydroxyl, alkoxy or C 1 -C 4 hydroxyalkyl radicals; or R1 is a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle optionally substituted with one or more radicals chosen from C 1 -C 4 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido or C 1 -C 4 hydroxyalkyl radicals; and when Z1 represents NR2 then R1 and R2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl radicals and hydroxyl, C 1 -C 4 alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals, it being possible for this heterocycle to contain one or more heteroatoms chosen from N or O, preferably N; or R1 and R2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical and optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl radicals and hydroxyl, C 1 -C 4 alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals; An − represents an anion or a mixture of anions which are organic or inorganic and are cosmetically acceptable.

1 - 13 . (canceled) 
     
     
         14 . A para-Aminophenol compound of formula (I), the addition salts thereof with an acid, and the solvates thereof: 
       
         
           
           
               
               
           
         
         wherein:
 R is chosen from a hydrogen atom, a halogen atom, a C 1 -C 4  alkyl radical, a carboxyl radical, and a (C 1 -C 4 )alkoxycarbonyl radical; 
 Z1 is chosen from an oxygen atom and a group NR2; 
 R2 is chosen from a hydrogen atom, a linear or branched C 1 -C 4  alkyl radical, a benzyl radical, and an acetyl radical; 
 R1 is chosen from a saturated, linear or branched C 1 -C 10  alkyl radical, which is substituted with or interrupted by a cationic radical; or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle; 
 
         with the proviso that when Z1 represents NR2, then R1 and R2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle; or a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical; and 
         An −  represents an anion or a mixture of anions which are organic or inorganic and are cosmetically acceptable. 
       
     
     
         15 . The compound according to  claim 14 , wherein R1 is a saturated, linear or branched C 1 -C 10  alkyl radical, which is interrupted by at least one oxygen atom and/or by at least one group NR2, and/or substituted with at least one radical chosen from hydroxyl, alkoxy or C 1 -C 4  hydroxyalkyl radicals; or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle substituted with at least one radical chosen from C 1 -C 4  alkyl, hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido or C 1 -C 4  hydroxyalkyl radicals. 
     
     
         16 . The compound according to  claim 14 , wherein when Z1 is NR2, then R1 and R2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle substituted with at least one radical chosen from C 1 -C 10  alkyl radicals and hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4  hydroxyalkyl radicals, wherein the heterocycle includes at least one heteroatom chosen from N or O; or a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with at least one radical chosen from C 1 -C 10  alkyl radicals and hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4  hydroxyalkyl radicals. 
     
     
         17 . The compound according to  claim 14 , wherein the cationic radical is a linear or branched or heterocyclic radical comprising a quaternary ammonium, the quaternary ammonium being of the type —N + RaRbRc, wherein Ra, Rb and Rc, which may be identical or different, are chosen from a C 1 -C 6  alkyl radical. 
     
     
         18 . The compound according to  claim 17 , wherein the C 1 -C 6  alkyl radical is substituted with a hydroxyl;
 with the proviso that when Ra and Rb form a 5- to 8-membered heterocycle, the radical Rc is a C 1 -C 6  alkyl radical optionally substituted with a hydroxyl.   
     
     
         19 . The compound according to  claim 14  wherein:
 R is chosen from a hydrogen atom and a C 1 -C 4  alkyl radical; 
 Z1 is chosen from an oxygen atom and a group NR2, wherein R2 is chosen from a hydrogen atom and a C 1 -C 2  alkyl radical; 
 R1 is chosen from a linear or branched C 1 -C 8  alkyl radical, which is substituted with or interrupted by a cationic radical; or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle. 
 
     
     
         20 . The compound according to  claim 19 , wherein:
 R is a hydrogen atom;   R2 is chosen from a hydrogen atom and CH 3 ;   R1 is chosen from a linear or branched C 1 -C 8  alkyl radical interrupted by at least one oxygen atom and/or by at least one group NR2, and/or substituted with a hydroxyl radical,   wherein said cationic radical is substituted with at least one radical chosen from C 1 -C 4  alkyl or C 1 -C 4  alkoxy radicals; or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle substituted with at least one radical chosen from C 1 -C 4  alkyl, hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, thio, (C 1 -C 4 )alkylthio, carboxyl, (C 1 -C 4 )alkylcarbonyl, sulfonyl, amido or C 1 -C 4  hydroxyalkyl radicals.   
     
     
         21 . The compound according to  claim 14  wherein:
 R is chosen from a hydrogen atom and a C 1 -C 4  alkyl radical; 
 Z1 represents NR2; and 
 R1 and R2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical. 
 
     
     
         22 . The compound according to  claim 21  wherein:
 R is a hydrogen atom; and 
 R1 and R2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical and substituted with at least one radical chosen from C 1 -C 10  alkyl radicals and hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 1 -C 4 )alkylcarbonyl, amido and C 1 -C 4  hydroxyalkyl radicals. 
 
     
     
         23 . The compound according to  claim 14 , wherein Z1 represents NR2, and R1 and R2 form, together with the nitrogen atom to which they are attached, a noncationic heterocycle chosen from pyrrolidine, piperidine, morpholine, and mixtures thereof. 
     
     
         24 . The compound according to  claim 14 , wherein at least one of R1 and a saturated or unsaturated cationic 5- to 8-membered heterocycle formed by R1 and R2 are substituted with or interrupted by a cationic radical chosen from trimethylammonium, triethylammonium, dimethylethylammonium,
 diethylmethylammonium, diisopropylmethylammonium, hydroxyethyldiethylammonium, imidazolium, pyridinium, piperazinium, pyrrolidinium, morpholinium, pyrimidinium, thiazolium, benzimidazolium and piperidinium radicals and mixtures thereof.   
     
     
         25 . The compound according to  claim 14 , wherein:
 R represents a hydrogen atom or a C 1 -C 4  alkyl radical;   Z1 represents NR2; and   R1 and R2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle.   
     
     
         26 . The compound according to  claim 25 , wherein:
 R represents a hydrogen atom; and   R1 and R2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle substituted with at least one radical chosen from C 1 -C 10  alkyl radicals and hydroxyl, C 1 -C 4  alkoxy, amino, (C 1 -C 4 )alkylam ino, di(C 1 -C 4 )alkylamino, (C 1 -C 4 )alkylcarbonyl, am ido and C 1 -C 4  hydroxyalkyl radicals.   
     
     
         27 . The compound according to  claim 25 , wherein the heterocycle contains at least one heteroatom chosen from N and O. 
     
     
         28 . The compound according to  claim 25 , wherein the cationic heterocycle is chosen from imidazolium, pyridinium, piperidinium, piperazinium, pyrrolidinium, morpholinium, pyrimidinium, thiazolium, benzimidazolium, benzothiazolium and oxazolium radicals and combinations thereof. 
     
     
         29 . The compound according to  claim 14 , wherein the compound is chosen from:
 2-(2-amino-5-hydroxyphenoxy)-N,N,N-trimethylethanaminium, An − ,   1-[2-(2-amino-5-hydroxyphenoxy)ethyl]-1-methylpiperidinium, An − ,   1-[2-(2-amino-5-hydroxyphenoxy)ethyl]-1-methylpyrrolidinium, An − ,   4-[2-(2-amino-5-hydroxyphenoxy)ethyl]-4-methylmorpholin-4-ium, An − ,   1-[2-(2-amino-5-hydroxyphenoxy)ethyl]-3-methyl-1H-imidazol-3-ium, An − ,   4-[2-(2-amino-5-hydroxyphenoxy)ethyl]-1,1-dimethylpiperazin-1-ium, An − ,   3-(2-amino-5-hydroxyphenoxy)-N,N,N-trimethylpropan-1-aminium, An − ,   1-[3-(2-amino-5-hydroxyphenoxy)propyl]-1-methylpiperidinium, An − ,   1-[3-(2-amino-5-hydroxyphenoxy)propyl]-1-methylpyrrolidinium, An − ,   4-[3-(2-amino-5-hydroxyphenoxy)propyl]-4-methylmorpholin-4-ium, An − ,   1-[3-(2-amino-5-hydroxyphenoxy)propyl]-3-methyl-1H-imidazol-3-ium, An − ,   4-[3-(2-amino-5-hydroxyphenoxy)propyl]-1,1-dimethylpiperazin-1-ium, An − ,   2-[(2-amino-5-hydroxyphenyl)amino]-N,N,N-trimethylethanaminium, An − ,   4-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-1,1-dimethylpiperazin-1-ium, An − ,   4-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-1-(2-hydroxyethyl)-1-methylpiperazin-1-ium, An − ,   1-{3-[(2-amino-5-hydroxyphenyl)amino]propyl}-1-methylpiperidinium, An − ,   1-{3-[(2-amino-5-hydroxyphenyl)amino]propyl}-1-methylpyrrolidinium, An − ,   4-{3-[(2-amino-5-hydroxyphenyl)amino]propyl}-4-methylmorpholin-4-ium, An − ,   1-{3-[(2-amino-5-hydroxyphenyl)amino]propyl}-3-methyl-1H-imidazol-3-ium, An − ,   3-[(2-amino-5-hydroxyphenyl)(methyl)amino]-N,N,N-trimethylpropan-1-aminium, An − ,   1-{3-[(2-amino-5-hydroxyphenyl)(methyl)amino]propyl}-1-methylpyrrolidinium, An − ,   1-{3-[(2-amino-5-hydroxyphenyl)(methyl)amino]propyl}-1-methylpiperidinium, An − ,   4-{3-[(2-amino-5-hydroxyphenyl)(methyl)amino]propyl}-4-methylmorpholin-4-ium, An − ,   4-(2-amino-5-hydroxyphenyl)-1,1-dimethylpiperazin-1-ium, An − ,   4-(2-amino-5-hydroxyphenyl)-1,1-bis(2-hydroxyethyl)piperazin-1-ium, An − ,   1-[2-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)ethyI]-1-methylpiperidinium, An − ,   1-[2-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)ethyl]-3-methyl-1H-imidazol-3-ium, An − ,   2-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)-N,N,N-trimethylethanaminium, An − ,   2-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}-N,N,N-trimethylethanaminium, An − ,   1-(2-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}ethyl)-1-methylpiperidinium, An − ,   4-(2-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}ethyl)-1,1-dimethylpiperazin-1-ium, An − ,   4-(2-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}ethyl)-4-methylmorpholin-4-ium, An − ,   3-[(2-amino-5-hydroxyphenyl)amino]-N,N,N-trimethylpropan-1-aminium, An − ,   4-{3-[(2-amino-5-hydroxyphenyl)amino]propyl}-1,1-dimethylpiperazin-1-ium, An − ,   1-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-1-methylpiperidinium, An − ,   1-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-1-methylpyrrolidinium, An − ,   4-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-4-methylmorpholin-4-ium, An − ,   1-{2-[(2-amino-5-hydroxyphenyl)amino]ethyl}-3-methyl-1H-imidazol-3-ium, An − ,   2-[(2-amino-5-hydroxyphenyl)(methyl)amino]-N,N,N-trimethylethanaminium, An − ,   1-{2-[(2-amino-5-hydroxyphenyl)(methyl)amino]ethyl}-1-methylpyrrolidinium, An − ,   1-{2-[(2-amino-5-hydroxyphenyl)(methyl)amino]ethyl}-1-methylpiperidinium, An − ,   4-{2-[(2-amino-5-hydroxyphenyl)(methyl)amino]ethyl}-4-methylmorpholin-4-ium, An − ,   1-(2-amino-5-hydroxyphenyl)-N,N,N-trimethylpyrrolidin-3-aminium, An − ,   4-(2-amino-5-hydroxyphenyl)-1-(2-hydroxyethyl)-1-methylpiperazin-1-ium, An − ,   1-[2-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)ethyl]-1-methylpyrrolidinium, An − ,   4-[2-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)ethyl]-4-methylmorpholin-4-ium, An − ,   3-({2-[(2-amino-5-hydroxyphenyl)amino]ethyl}amino)-N,N,N-trimethylpropan-1-aminium, An − ,   3-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}-N,N,N-trimethylpropan-1-aminium, An − ,   1-(2-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}ethyl)-1-methylpyrrolidinium, An − ,   4-(3-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}propyl)-1,1-dimethylpiperazin-1-ium, An − ,   4-(3-{2-[(2-amino-5-hydroxyphenyl)amino]ethoxy}propyl)-4-methylmorpholin-4-ium, An − ,   the addition salts thereof with an acid and/or solvates thereof, and mixtures thereof.   
     
     
         30 . A dye composition for dyeing keratin fibers comprising, in a medium that is suitable for dyeing keratin fibers, at least one para-Aminophenol compound of formula (I), the addition salts thereof with an acid, and the solvates thereof: 
       
         
           
           
               
               
           
         
         wherein:
 R is chosen from a hydrogen or halogen atom; a C 1 -C 4  alkyl radical; a carboxyl radical; and a (C 1 -C 4 )alkoxycarbonyl radical; 
 Z1 is chosen from an oxygen atom and a group NR2; 
 R2 is chosen from a hydrogen atom, a linear or branched C 1 -C 4  alkyl radical, a benzyl radical, and an acetyl radical; 
 R1 is chosen from a saturated, linear or branched C 1 -C 10  alkyl radical, which is substituted with or interrupted by a cationic radical; 
 
         or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle; 
         with the proviso when Z1 represents NR2 then
 R1 and R2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle; or a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical; and 
 An −  represents an anion or a mixture of anions which are organic or inorganic and are cosmetically acceptable. 
 
       
     
     
         31 . A method for dyeing keratin fibers, the method comprising:
 applying to the keratin fibers in the presence of at least one oxidizing agent for a period of time sufficient to develop the desired coloring, a para-Aminophenol compound of formula (I), the addition salts thereof with an acid, and the solvates thereof:   
       
         
           
           
               
               
           
         
         wherein:
 R is chosen from a hydrogen or halogen atom; a C 1 -C 4  alkyl radical; a carboxyl radical; and a (C 1 -C 4 )alkoxycarbonyl radical; 
 Z1 is chosen from an oxygen atom and a group NR2; 
 R2 is chosen from a hydrogen atom, a linear or branched C 1 -C 4  alkyl radical, a benzyl radical, and an acetyl radical; 
 R1 is chosen from a saturated, linear or branched C 1 -C 10  alkyl radical, which is substituted with or interrupted by a cationic radical; 
 
         or a saturated, unsaturated or aromatic cationic 5- to 8-membered heterocycle; 
         with the proviso when Z1 represents NR2 then
 R1 and R2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated cationic 5- to 8-membered heterocycle; or a saturated or unsaturated noncationic 5- to 8-membered heterocycle substituted with a cationic radical; and 
 An −  represents an anion or a mixture of anions which are organic or inorganic and are cosmetically acceptable. 
 
       
     
     
         32 . A multi-compartment device comprising a first compartment configured to contain the dye composition according to  claim 30  and a second compartment configured to contain at least one oxidizing agent. 
     
     
         33 . The dye composition according  claim 30  further comprising an oxidizing agent chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes.