Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1998-02-24
2001-03-20
Liott, Caroline D. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S408000, C008S409000, C008S423000, C008S571000, C008S573000, C008S574000, C008S575000, C008S577000, C549S469000
Reexamination Certificate
active
06203580
ABSTRACT:
The invention relates to novel compositions for the oxidation dyeing of keratin fibers, comprising at least one para-aminophenol as oxidation base, to the dyeing process using this composition, to novel para-aminophenols and to a process for their preparation.
It is known to dye keratin fibers, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds such as diaminopyrazole derivatives, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless or weakly colored compounds which, when combined with oxidizing products, may give rise to colored compounds and dyes by a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being selected in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colors.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks and it must allow shades of the desired intensity to be obtained and have good resistance to external agents (light, bad weather, washing, permanent-waving, perspiration and rubbing).
The dyes must also allow white hairs to be covered and, lastly, they must be as unselective as possible, that is to say that they must allow the smallest possible differences in coloration to be produced over the entire length of the same keratin fiber, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
The inventors have now discovered, entirely surprisingly and unexpectedly, that certain para-aminophenols of formula (I) defined below, for those which are novel per se, are suitable for use as oxidation dye precursors.
This discovery forms the basis of the present invention.
A first subject of the invention is thus a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it comprises, in a medium which is suitable for dyeing, as oxidation base, at least one para-aminophenol of formula (I) below, and/or at least one acid-addition salt thereof:
in which:
R
1
represents a hydrogen atom, a linear or branched C
1
-C
4
alkyl radical or a C
1
-C
4
trifluoroalkyl radical,
R
2
and R
3
independently represent a hydrogen atom, a C
1
-C
4
alkyl radical or a C
1
-C
4
monohydroxyalkyl radical,
X, Y and Z independently represent a carbon, nitrogen, oxygen or sulphur atom,
the bonds XY and YZ can be single or double bonds.
As mentioned above, the oxidation dye compositions in accordance with the invention can produce a coloration on keratin fibers in oxidizing medium.
Another subject of the invention is the use of the para-aminophenols of formula (I) as oxidation base in compositions for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair.
In general, the acid-addition salts which can be used in the context of the dye compositions of the invention (oxidation bases and couplers) are selected in particular from the hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
Among the para-aminophenols of formula (I) which can be used as oxidation bases in the compositions in accordance with the invention, mention may be made in particular of:
4-amino-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol,
7-amino-3H-benzoimidazol-4-ol,
7-aminobenzo[b]thiophen-4-ol,
7-amino-2,3-dimethylbenzofuran-4-ol,
4-amino-2,3-dimethylbenzofuran-7-ol,
7-amino-1-propyl-5-trifluoromethyl-1H-benzoimidazol-4-ol,
7-aminobenzo[b]isothiazol-4-ol,
7-amino-1H-benzotriazol-4-ol,
4-amino-2,3-dihydro-1H-indol-7-ol,
7-aminoindan-4-ol,
7-amino-5-methyl-2,1,3-benzothiadiazol-4-ol,
7-amino-2,1,3-benzothiadiazol-4-ol,
7-amino-1-methyl-1H-indol-4-ol,
7-amino-1-(2-hydroxyethyl)-1H-indol-4-ol,
and the acid-addition salts thereof.
Among these para-aminophenols, the ones more particularly preferred are:
4-amino-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol,
7-amino-3H-benzoimidazol-4-ol,
7-amino-1-methyl-1H-indol-4-ol,
and the acid-addition salts thereof.
The para-aminophenol(s) of formula (I) above preferably represent(s) from approximately 0.0005 to approximately 12% by weight relative to the total weight of the dye composition, and even more preferably from approximately 0.005 to approximately 6% by weight.
The medium which is suitable for dyeing (or the support) generally comprises water or a mixture of water and at least one organic solvent to solubilize the compounds which would not be sufficiently soluble in water. Organic solvents which may be mentioned, for example, are C
1
-C
4
lower alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, and aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
The solvents may be present in proportions preferably ranging from approximately 1 to approximately 40% by weight relative to the total weight of the dye composition, and even more preferably from approximately 5 to approximately 30% by weight, relative to the total weight of the dye composition.
The pH of the dye composition in accordance with the invention preferably ranges from 3 to 12 and more preferably from 5 to 11. It may be adjusted to the desired value using acidifying or basifying agents usually used in the dyeing of keratin fibers.
Among the acidifying agents which may be mentioned, by way of example, are inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulphonic acids.
Among the basifying agents which may be mentioned, by way of example, are aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide or potassium hydroxide and the compounds of formula (II) below:
in which:
W is a propylene residue optionally substituted with a hydroxyl group or a C
1
-C
4
alkyl radical;
R
4
, R
5
, R
6
and R
7
independently represent a hydrogen atom or a C
1
-C
4
alkyl or C
1
-C
4
hydroxyalkyl radical.
In addition to the dyes of formula (I) defined above, the dye composition in accordance with the invention can also contain at least one additional oxidation base which can be selected from the oxidation bases conventionally used in oxidation dyeing and among which mention may be made in particular of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases other than the para-aminophenols of formula (I) used in accordance with the invention.
Among the para-phenylenediamines, mention may be made more particularly, by way of example, of para-phenylenediamine, para-toluylenediamine, 2,6-dimethyl-para-phenylenediamine, 2-&bgr;-hydroxyethyl-para-phenylene-diamine, 2-n-propyl-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(&bgr;-hydroxypropyl)-para-phenylenediamine, N,N-bis-(&bgr;-hydroxyethyl)-para-phenylenediamine, 4amino-N-(&bgr;-methoxyethyl)aniline, and the para-phenylenediamines described in French patent application FR-A-2,630,438, the disclosure of which is specifically incorporated by reference herein, and the acid-addition salts thereof.
Among the bis(phenyl)alkylenediamines, mention may be made more particularly, by way of example, of N,N′-bis(&bgr;-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3-diaminopropanol, N,N′-bis(&bgr;-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetrameth
Lagrange Alain
Vandenbossche Jean Jacques
Finnegan, Henderson, Farabow, Garret & Dunner
L'Oreal
Liott Caroline D.
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