Tri-aromatic azomethine direct dyes comprising at least one unit derived from resorcinol, dyeing composition, method and use
The present invention relates to azomethine-type direct dyes with a tri-aromatic unit having the following formula (I): and their use for coloring keratin fibers, particularly human keratin fibers such as the hair. The invention also relates to a composition for dyeing keratin fibers comprising, in a suitable medium for dyeing, such direct dyes. Another subject of the present invention is a method for dyeing keratin fibers using said dyeing composition. Finally the present invention also relates to precursors for these direct dyes.
1. An azomethine-type direct dye with a tri-aromatic unit of formula (I), the organic or inorganic acid or base salts thereof, the tautomeric forms thereof, the optical isomers and geometric isomers thereof, and/or the solvates thereof:
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom, or a linear or branched C 1 -C 6 alkyl radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical.
2. Azomethine direct dye according to claim 1 , wherein:
n is an integer equal to 0, 1 or 2;
R is chosen from:
a C 1 -C 2 alkyl radical,
a C 1 -C 2 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals; wherein An − represents a cosmetically acceptable anion or mixture of anions,
a C 1 -C 2 alkoxy radical, and
a chlorine atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 3 alkyl radical substituted with a hydroxyl radical, and
a C 1 -C 2 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 2 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom, or a linear or branched C 1 -C 3 alkyl radical, and R 4 , which may be identical or different, is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 3 alkyl radical, or
a linear or branched C 1 -C 3 alkyl radical substituted with at least one hydroxyl or C 1 -C 2 alkoxy radical;
when R 1 and R 2 denote a hydrogen atom and n equals 0 then X does not denote a hydroxyl or amino —NH 2 radical.
3. The azomethine direct dye according to claim 1 , wherein R 1 is chosen from a hydrogen atom and a linear or branched C 1 -C 9 alkyl radical.
4. The azomethine direct dye according to claim 1 , wherein R 2 is a hydrogen atom.
5. The azomethine direct dye according to claim 1 , wherein X is an amino —NR 3 R 4 radical in which R 3 is chosen from a hydrogen atom and a linear or branched C 1 -C 3 alkyl radical, and R 4 is chosen from a hydrogen atom and a linear or branched C 1 -C 3 alkyl radical, optionally substituted by a hydroxyl radical.
6. The azomethine direct dye according to claim 1 , wherein the compound is chosen from the following compounds and the geometric or optical isomeric forms thereof, the salts with an organic or inorganic acid thereof, and the solvates thereof:
2-[4-(Ethylisopropylamino)- phenyl- amino]-4-[4-(ethylisopropyl- amino)phenylimino]-5- hydroxy-3-methylcyclohexa- 2,5-dienone
2-{4-[Ethyl(2-hydroxyethyl)- amino]-2-methyl- phenylamino}-4-{4-[ethyl(2- hydroxyethyl)-amino]-2- methylphenylimino}-5- hydroxy-3-methyl- cyclohexa-2,5-dienone
2-(4-Amino-2,3-dimethyl- phenylamino)-4-[4-amino- 2,3-dimethylphenylimino]-5- hydroxy-3-methylcyclohexa- 2,5-dienone
2-(4-Aminophenylamino)-4- [4-aminophenylimino]-5- hydroxy-3-methyl- cyclohexa-2,5-dienone
5-Hydroxy-2-(4-hydroxy- phenylamino)- 4-[4-hydroxyphenylimino]- 3-methylcyclohexa-2,5- dienone
2-(4-Amino-3 (or 2)-methyl- phenylamino)-4- [4-amino-3 (or 2)-methyl- phenylimino]- 5-hydroxy-3-methyl- cyclohexa-2,5-dienone
2-(3-Chloro-4-hydroxy- phenylamino)- 4-[3-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- methylcyclohexa-2,5- dienone
2-(2-Chloro-4-hydroxy- phenylamino)- 4-[2-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- methylcyclohexa-2,5- dienone
5-Hydroxy-2-[4-(6-hydroxy- hexylamino)phenylamino]-4- [4-(6-hydroxy- hexylamino)phenylimino]-3- methyl- cyclohexa-2,5-dienone
2-[4-(Ethylisopropylamino)- phenyl- amino]-4-[4-(ethylisopropyl- amino)phenylimino]-5- hydroxycyclohexa-2,5- dienone
2-{4-[Ethyl(2-hydroxy- ethyl)amino]-2-methyl- phenylamino}-4-{4-[ethyl(2- hydroxyethyl)amino]-2- methylphenylimino}-5- hydroxy- cyclohexa-2,5-dienone
2-(4-Amino-2,3-dimethyl- phenylamino)-4-[4-amino- 2,3-dimethylphenylimino]-5- hydroxy-3-methylcyclohexa- 2,5-dienone
2-(4-Amino-3-methyl- phenylamino)-4- [4-amino-3 (or 2)-methyl- phenylimino]- 5-hydroxycyclohexa-2,5- dienone
2-(3-Chloro-4-hydroxy- phenylamino)- 4-[3-chloro-4-hydroxy- phenylimino]-5-hydroxy- cyclohexa-2,5-dienone
2-(2-Chloro-4-hydroxy- phenylamino)- 4-[2-chloro-4-hydroxy- phenylimino]-5-hydroxy- cyclohexa-2,5-dienone
5-Hydroxy-2-[4-(6-hydroxy- hexylamino)phenylamino]-4- [4-(6-hydroxy- hexylamino)phenylimino]- cyclohexa-2,5-dienone
6-[4-(Ethylisopropylamino)- phenyl- amino]-4-[4-(ethylisopropyl- amino)phenylimino]-3- hydroxy-2- methoxycyclohexa-2,5- dienone
2-{4-[Ethyl(2-hydroxyethyl)- amino]-2-methyl- phenylamino}-4-{4-[ethyl(2- hydroxyethyl)amino]-2- methylphenylimino}-2- hydroxy-2-methoxy- cyclohexa-2,5-dienone
2-(4-Amino-2,3-dimethyl- phenylamino)-4-[4-amino- 2,3-dimethylphenylimino]-3- hydroxy-2- methoxycyclohexa-2,5- dienone
2-(4-Aminophenylamino)-4-[4- aminophenylimino]-3-hydroxy- 2-methoxy- cyclohexa-2,5-dienone
3-Hydroxy-2-(4-hydroxy- phenylamino)- 4-[4-hydroxyphenylimino]-2- methoxycyclohexa-2,5-dienone
2-(4-Amino-3 (or 2)-methyl- phenylamino)-4- [4-amino-3 (or 2)-methyl- phenylimino]- 3-hydroxy-2-methoxycyclohexa- 2,5-dienone
2-(3-Chloro-4-hydroxy- phenylamino)- 4-[3-chloro-4-hydroxy- phenylimino]-3-hydroxy-2- methoxycyclohexa-2,5-dienone
2-(2-Chloro-4-hydroxy- phenylamino)- 4-[2-chloro-4-hydroxy- phenylimino]-3-hydroxy-2- methoxycyclohexa-2,5- dienone
3-Hydroxy-2-[4-(6-hydroxy- hexylamino)phenylamino]-4- [4-(6-hydroxy- hexylamino)phenylimino]-2- methoxy- cyclohexa-2,5-dienone
2-[4-(Ethylisopropylamino)- phenyl- amino]-4-[4-(ethylisopropyl- amino)phenylimino]-5- hydroxy-3-pentylcyclohexa- 2,5-dienone
2-{4-[Ethyl(2-hydroxyethyl)- amino]-2-methyl- phenylamino}-4-{4-[ethyl(2- hydroxyethyl)amino]-2- methylphenylimino}-5- hydroxy-3-pentyl- cyclohexa-2,5-dienone
2-(4-Amino-2,3-dimethyl- phenylamino)-4-[4-amino- 2,3-dimethylphenylimino]-5- hydroxy-3-pentylcyclohexa- 2,5-dienone
2-(4-Aminophenylamino)-4- [4-aminophenylimino]-5- hydroxy-3-pentyl- cyclohexa-2,5-dienone
5-Hydroxy-2-(4-hydroxy- phenylamino)- 4-[4-hydroxyphenylimino]-3- pentylcyclohexa-2,5-dienone
2-(4-Amino-3 (or 2)-methyl- phenylamino)-4- [4-amino-3 (or 2)-methyl- phenylimino]- 5-hydroxy-3- pentylcyclohexa-2,5-dienone
2-(3-Chloro-4-hydroxy- phenylamino)- 4-[3-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- pentylcyclohexa-2,5-dienone
2-(2-Chloro-4-hydroxy- phenylamino)- 4-[2-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- pentylcyclohexa-2,5-dienone
5-Hydroxy-2-[4-(6- hydroxyhexylamino)phenyl- amino]-4-[4-(6-hydroxy- hexylamino)phenylimino]-3- pentyl- cyclohexa-2,5-dienone
2-[4-(Ethylisopropylamino)- phenyl- amino]-4-[4-(ethylisopropyl- amino)phenylimino]-5- hydroxy-3-hydroxymethyl- cyclohexa-2,5-dienone
2-{4-[Ethyl(2-hydroxyethyl)- amino]-2-methyl- phenylamino}-4-{4-[ethyl(2- hydroxyethyl)amino]-2- methylphenylimino}-5- hydroxy-3-hydroxymethyl- cyclohexa-2,5-dienone
2-(4-Amino-2,3- dimethylphenylamino)-4-[4- amino-2,3- dimethylphenylimino]-5- hydroxy-3-hydroxymethyl- cyclohexa-2,5-dienone
2-(4-Aminophenylamino)-4- [4-aminophenylimino]-5- hydroxy-3-hydroxymethyl- cyclohexa-2,5-dienone
5-Hydroxy-2-(4-hydroxy- phenylamino)- 4-[4-hydroxyphenylimino]-3- hydroxymethylcyclohexa-2,5- dienone
2-(4-Amino-3 (or 2)-methyl- phenylamino)-4- [4-amino-3 (or 2)-methyl- phenylimino]- 5-hydroxy-3-hydroxymethyl- cyclohexa-2,5-dienone
2-(3-Chloro-4-hydroxy- phenylamino)- 4-[3-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- hydroxymethylcyclohexa-2,5- dienone
2-(2-Chloro-4-hydroxy- phenylamino)- 4-[2-chloro-4-hydroxy- phenylimino]-5-hydroxy-3- hydroxymethylcyclohexa-2,5- dienone
5-Hydroxy-2-[4-(6-hydroxy- hexylamino)phenylamino]-4- [4-(6-hydroxy- hexylamino)phenylimino]-3- hydroxymethylcyclohexa-2,5- dienone.
7. A composition for dyeing keratin fibers, comprising, in a suitable dyeing medium, at least one azomethine-type direct dye of formula (I):
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom, or a linear or branched C 1 -C 6 alkyl radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical.
8. A method for dyeing keratin fibers, the method comprising:
applying to the keratin fibers a dye composition comprising, in a suitable medium for dyeing, for a time sufficient to obtain a desired coloration, at least one azomethine-type direct dye of formula (I):
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom or a linear or branched l radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical;
rinsing the fibers;
optionally washing the fibers with shampoo;
optionally rinsing the fibers; and
drying the keratin fibers or leaving the keratin fibers to dry.
9. A method for lightening keratin fibers, the method comprising:
applying a dye composition comprising, in a suitable dyeing medium, (i) at least one azomethine-type direct dye of formula (I) free of oxidizing agent, and (ii) a cosmetic composition comprising at least one oxidizing agent, wherein compositions (i) and (ii) are applied to the keratin fibers sequentially or simultaneously for a time sufficient to obtain a desired lightening:
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical;
rinsing the fibers;
optionally washing the fibers with shampoo;
optionally rinsing the fibers; and
drying the fibers or leaving the fibers to dry.
10. A leuco-type compound having the following formula (II), the organic or inorganic salts with an acid or a base thereof, the tautomeric forms thereof, the optical isomers and geometric isomers thereof, and the solvates thereof:
wherein:
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical.
11. A cosmetic composition comprising, in a cosmetically acceptable medium, at least one leuco-type compound of formula (II) as defined according to claim 10 .
12. A method for dyeing keratin fibers, the method comprising:
applying to the fibers for a time sufficient to develop a desired coloration, a cosmetic composition comprising at least one leuco-type compound of formula (II) in the presence of at least one oxidizing agent:
wherein:
n is an integer equal to 0, 1, 2, 3 or 4;
R is chosen from:
a linear or branched C 1 -C 4 alkyl radical,
a linear or branched C 1 -C 4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An − radicals, wherein An − represents a cosmetically acceptable anion or a combination of anions,
a C 1 -C 4 alkoxy radical, and
a halogen atom;
R 1 is chosen from:
a hydrogen atom,
a linear or branched C 1 -C 9 alkyl radical,
a linear or branched C 1 -C 9 alkyl radical substituted with at least one hydroxyl radical, and
a C 1 -C 3 alkoxy radical;
R 2 is chosen from:
a hydrogen atom, and
a C 1 -C 3 alkoxy radical;
X is chosen from:
a hydroxyl radical, and
a —NR 3 R 4 radical wherein R 3 is chosen from a hydrogen atom or a linear or branched C 1 -C 6 alkyl radical, and R 4 , which may be identical or different, is chosen from a hydrogen atom, a linear or branched C 1 -C 6 alkyl radical, or a linear or branched C 1 -C 6 alkyl radical substituted with at least one hydroxyl or C 1 -C 4 alkoxy radical;
when R 1 and R 2 represent a hydrogen atom and n equals 0 then X does not represent a hydroxyl or amino —NH 2 radical;
rinsing the fibers;
optionally washing the fibers with shampoo;
optionally rinsing the fibers, and
drying the fibers or leaving the fibers to dry.
13. A multi-compartment device comprising a first compartment configured to contain the dye composition according to claim 7 , and a second compartment configured to contain at least one oxidizing agent.
14. A multi-compartment kit comprising a first compartment configured to contain the dye composition according to claim 7 , and a second compartment configured to contain at least one oxidizing agent.
15. A multi-compartment device comprising a first compartment configured to contain the dye composition according to claim 10 , and a second compartment configured to contain at least one oxidizing agent.
16. A multi-compartment kit comprising a first compartment configured to contain the dye composition according to claim 10 , and a second compartment configured to contain at least one oxidizing agent.