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US 9,233,057 B2Granted
Particular quinone direct dyes, dye composition comprising at least one such dye, implementation process therefor and use thereof
AssigneeL'oreal
InventorStephane Sabelle
Life of this patent
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Abstract
The present invention relates to quinone direct dyes of formula (I) below, organic or mineral acid or base salts thereof, tautomeric forms, optical isomers or geometrical isomers thereof and/or solvates thereof: and also to the use thereof for dyeing keratin fibers, in particular human keratin fibers such as the hair. The invention also relates to a composition for dyeing keratin fibers, comprising such direct dyes in a suitable dyeing medium. Similarly, a subject of the present invention is a process for dyeing keratin fibers, using the said dye composition.
Claims16
A quinone direct dye of formula (I), the organic or mineral acid or base salts thereof, the tautomeric forms thereof, the optical isomers or geometrical 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 C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy radical.
16 more elements
A composition for dyeing keratin fibers, comprising, in a suitable dyeing medium, at least one quinone 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 C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radicals;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy radical.
16 more elements
A method for dyeing keratin fibers, the method comprising:
- applying to the keratin fibers a dye composition comprising, in a suitable dyeing medium, for a time sufficient to obtain a desired coloration, at least one quinone 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 C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radicals;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy 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.
22 more elements
A method for lightening keratin fibers, the method comprising:
- applying a dye composition comprising, in a suitable dyeing medium, (i) at least one quinone 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 that is 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 C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radicals;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy radical;
- rinsing the fibers;
- optionally washing the fibers with shampoo;
- optionally rinsing the fibers;
- and
- drying the fibers or leaving the fibers to dry.
22 more elements
A leuco type compound of formula (II), the organic or mineral acid or base salts thereof, the tautomeric forms thereof, the optical isomers or geometrical isomers thereof, and the solvates thereof:
- wherein:
- n is an integer equal to 0, 1, 2, 3 or 4;
- R is chosen from:
- a linear or branched C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radicals;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy radical.
16 more elements
A method for dyeing keratin fibers, the method comprising:
- applying to the keratin fibers, which may be wet or dry, simultaneously or sequentially (i) a dye composition comprising at least one compound of formula (II), and (ii) an oxidizing composition comprising 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 C1-C4 alkyl radical,
- a linear or branched C1-C4 alkyl radical substituted with at least one radical chosen from hydroxyl, imidazolium, and An radicals, wherein An represents a cosmetically acceptable anion or combination of anions,
- a C1-C4 alkoxy radical, and
- a halogen atom;
- R1 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radicals;
- R2 is chosen from:
- a linear or branched C1-C5 alkyl radical, and
- a linear or branched C1-C5 alkyl radical substituted with at least one hydroxyl radical;
- X is chosen from:
- a hydroxyl radical, and
- a radical —NR3R4 wherein R3 and R4 represent, independently of each other:
- a hydrogen atom;
- a linear or branched C1-C6 alkyl radical;
- a linear or branched C1-C6 alkyl radical, substituted with at least one hydroxyl or C1-C4 alkoxy radical.
17 more elements
Dependencies are inferred from the claim text.