Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-06-03
2002-08-27
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S408000, C008S410000, C008S412000, C008S416000, C008S421000, C008S424000
Reexamination Certificate
active
06440176
ABSTRACT:
The subject-matter of the invention is a composition for the oxidation dyeing of keratinous fibres, in particular of human keratinous fibres, such as hair, comprising at least one suitably selected para-phenylenediamine derivative as oxidation base, in combination with at least one suitably selected coupler of meta-aminophenol or meta-diphenol type, and the dyeing process employing this composition.
It is known to dye keratinous fibres and in particular human hair with dyeing compositions comprising oxidation dye precursors, in particular ortho- or para-phenylenediamines or ortho- or para-aminophenols, generally known as oxidation bases. Oxidation dye precursors or oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing substances, can give rise by an oxidative coupling process to coloured and colouring compounds.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or colouring modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols or meta-diphenols.
The variety of the molecules employed as oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The so-called “permanent” colouring obtained by virtue of these oxidation dyes has, however, to satisfy a certain number of requirements. Thus, it must be without disadvantage toxicologically and it must make it possible to obtain shades with the desired intensity and behave well in the face of external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
Provision has already been made, in particular in French Patent Application FR-A-2 364 888, for compositions for the oxidation dyeing of keratinous fibres comprising, as oxidation base, para-phenylenediamines substituted in the 2 position, such as, for example, 2-(&bgr;-mesylaminoethyloxy)-para-phenylenediamine, optionally in combination with one or more couplers of meta-aminophenol, such as, for example, 5-amino-2-methylphenol, meta-phenylenediamine or meta-diphenol type, in order to obtain, in oxidizing alkaline medium, colourings with blue shades which are more or less purple, these being very luminous. The colourings obtained with these compositions are not, however, entirely satisfactory, in particular as regards the behaviour of these colourings with respect to various attacks which hair may be subjected to and in particular with respect to perspiration and permanent waving.
The present invention is targeted at providing novel compositions for the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as hair, which exhibit very good dyeing properties.
Thus, the Applicant Company has now just discovered that it is possible to obtain novel dyes which are particularly resistant and which generate intense colourings by combining:
at least one para-phenylenediamine derivative of formula (I) defined below and/or one of its addition salts with an acid,
at least coupler of formula (II) defined below and/or one of its addition salts with an acid.
This discovery is at the basis of the present invention.
The first subject-matter of the invention is therefore a composition for the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as hair, characterized in that it comprises, in a medium appropriate for dyeing:
at least one oxidation base chosen from para-phenylenediamine derivatives of following formula (I) and their addition salts with an acid:
in which:
R
1
represents a hydrogen atom or a mesyl, carbamoyl or acetyl radical,
n is an integer between 1 and 4 inclusive;
at least one coupler chosen from compounds of following formula (II) and their addition salts with an acid:
in which:
R
2
represents a hydroxyl radical or an NHR
4
group where R
4
denotes a hydrogen atom or a C
1
-C
4
alkyl, C
1
-C
4
monohydroxyalkyl or C
2
-C
4
polyhydroxyalkyl radical,
R
3
represents a hydrogen atom, a C
1
-C
4
alkyl or C
1
-C
4
alkoxy radical or a halogen atom chosen from chlorine, bromine and fluorine;
it being understood that, when n=2, when R
1
represents a mesyl radical, when R
3
represents a methyl radical in the 6 position and when R
2
represents an NHR
4
group, then R
4
is other than a hydrogen atom.
The colourings obtained with the above compositions exhibit a good dyeing power and excellent properties of resistance both with respect to atmospheric agents, such as light and bad weather, and with respect to perspiration and various treatments which hair can be subjected to (shampoos, permanent deformations).
Another subject-matter of the invention is a process for the oxidation dyeing of keratinous fibres employing this composition.
The addition salts with an acid which can be used in the context of the dyeing compositions of the invention can in particular be chosen from hydrochlorides, hydrobromides, sulphates and tartrates.
Mention may more particularly be made, among the para-phenylenediamine derivatives of above formula (I), of 2-(&bgr;-mesylaminoethyloxy)-para-phenylenediamine, 2-(&bgr;-ureidoethyloxy)-para-phenylenediamine, 2-(&bgr;-acetylaminoethyloxy)-para-phenylenediamine, 2-(&bgr;-aminoethyloxy)-para-phenylenediamine and their addition salts with an acid.
Mention may more particularly be made, among the couplers of above formula (II), of meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(&bgr;-hydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-(&bgr;-hydroxyethyl)amino-2-methylphenol, 5-N-(&ggr;-hydroxypropyl)amino-2-methylphenol, 1,3-dihydroxybenzene, 2-methyl-1,3-dihydroxybenzene, 4-chloro-1,3-dihydroxybenzene and their addition salts with an acid.
The para-phenylenediamine derivative or derivatives of formula (I) in accordance with the invention and/or its or their addition salts with an acid preferably represent from 0.0005 to 10% by weight approximately of the total weight of the dyeing composition and more preferably still from 0.05 to 7% by weight approximately.
The coupler or couplers of formula (II) in accordance with the invention and/or its or their addition salts with an acid preferably represent from 0.0001 to 5% by weight approximately of the total weight of the dyeing composition and more preferably still from 0.005 to 3% by weight approximately.
The medium appropriate for dyeing (or vehicle) is generally composed of water or of a mixture of water and of at least one organic solvent, in order to dissolve the compounds which would not be sufficiently soluble in water. Mention may be made, for example, as organic solvent, of lower C
1
-C
4
alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers, such as 2-butoxyethanol, propylene glycol, diethylene glycol monoethyl ether and diethylene glycol monomethyl ether, and aromatic alcohols, such as benzyl alcohol or phenoxyethanol, the analogous products and their mixtures.
The solvents can be present in proportions preferably of between 1 and 40% by weight approximately with respect to the total weight of the dyeing composition and more preferably still between 5 and 30% by weight approximately.
The pH of the dyeing composition as defined above is generally between 5 and 12 approximately. It can be adjusted to the desired value by means of acidifying or basifying agents commonly used in dyeing keratinous fibres.
Mention may be made, among acidifying agents, by way of examples, of inorganic or organic acids, such as hydrochloric acid, orthophosphoric acid, carboxylic acids, such as tartaric acid, citric acid or lactic acid, or sulphonic acids.
Mention may be made, among basifying agents, by way of examples, of aqueous ammonia, alkaline carbonates, alkanolamines, such as mono-, di- and triethanolamines, and their derivatives, sodium hydroxide, potassium hydroxide and the compounds of following formula (III):
in which R is a propylene residue optionally substituted by a hydroxyl group or a C
1
-C
4
alkyl radical; and R
5
, R
6
, R
7
and R
8
, which are identical or different, represent a hydrogen atom
Audousset Marie-Pascale
Cotteret Jean
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal
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