Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-04-26
2004-02-17
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S423000
Reexamination Certificate
active
06692540
ABSTRACT:
A subject-matter of the invention is a composition for the oxidation dyeing of keratinous fibres comprising at least one pyrazolo[1,5-a]pyrimidine as oxidation base and at least one pyridine coupler, and the oxidation 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, ortho- or para-aminopnenols, bisphenylalkylenediamines or, alternatively, heterocyclic compounds, 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, meta-diphenols and certain heterocyclic compounds.
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 have no disadvantages with regard to toxicology 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).
The dyes must also make it possible to cover white hair and, finally, be as unselective as possible, that is to say make it possible to obtain the least possible differences in colouring along the same keratinous fibre, this being because the latter can be sensitized (i.e. damaged) to a varying degree between its tip and its root.
Provision has already been made, in particular in Patent Application FR-A-2,750,048, for the use of pyrazolo[1,5-a]pyrimidines as oxidation base, alone or in combination with one or more couplers. However, the colourings obtained are not always powerful enough, chromatic enough or sufficiently resistant to the various attacks which hair may be subjected to.
In point of fact, the Applicant Company has now just discovered, entirely unexpectedly and surprisingly, that the combination of the pyrazolo[1,5-a]pyrimidines of formula (I) defined hereinbelow and of at least one pyridine coupler of formula (II) defined hereinbelow made it possible to obtain powerful colourings furthermore exhibiting improved properties of resistance with respect to various attacks which hair may be subjected to (shampoos, light, bad weather, permanent waves, perspiration, rubbing and the like).
These discoveries form the basis of the present invention.
A 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 pyrazolo[1,5-a]pyrimidines of following formula (I) and their addition salts with an acid or with a base:
in which:
R
1
, R
2
, R
3
and R
4
, which are identical or different, denote a hydrogen atom, a (C
1
-C
4
)alkyl radical, an aryl radical, a hydroxy(C
1
-C
4
)alkyl radical, a polyhydroxy(C
2
-C
4
)alkyl radical, a (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl radical, an amino(C
1
-C
4
)alkyl radical (it being possible for the amine to be protected by an acetyl, an amido or a sulphonyl), a (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical, a di[(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered aliphatic or heterocyclic ring), a hydroxy(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical or a di[hydroxy(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radical;
the X radicals, which are identical or different, denote a hydrogen atom, a (C
1
-C
4
)alkyl radical, an aryl radical, a hydroxy(C
1
-C
4
)alkyl radical, a polyhydroxy(C
2
-C
4
)alkyl radical, an amino(C
1
-C
4
)alkyl radical, a (C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical, a di[(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radical (it being possible for the dialkyls to form a 5- or 6-membered aliphatic or heterocyclic ring), a hydroxy(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl radical, a di[hydroxy(C
1
-C
4
)alkyl]amino(C
1
-C
4
)alkyl radical, an amino radical, a (C
1
-C
4
)alkylamino radical, a di[(C
1
-C
4
)alkyl]amino radical, a halogen atom, a carboxylic acid group or a sulphonic acid group;
i has the value 0, 1, 2 or 3;
p has the value 0 or 1;
q has the value 0 or 1;
n has the value 0 or 1;
with the proviso that:
(i) the sum p+q is other than 0;
(ii) when p+q is equal to 2, then n has the value 0 and the NR
1
R
2
and NR
3
R
4
groups occupy the (2,3), (5,6), (6,7), (3,5) or (3,7) positions;
(iii) when p+q is equal to 1, then n has the value 1 and the NR
1
R
2
(or NR
3
R
4
) group and the OH group occupy the (2,3), (5,6), (6,7), (3,5) or (3,7) positions;
and at least one coupler chosen from pyridines of following formula (II) and their addition salts with an acid:
in which:
R
5
represents a hydrogen atom or a hydroxyl, amino, (C
1
-C
4
)alkoxy, mono- or di(C
1
-C
4
)alkylamino, monohydroxy(C
1
-C
4
)alkylamino, polyhydroxy(C
2
-C
4
)alkylamino, monohydroxy(C
1
-C
4
)alkoxy, polyhydroxy(C
2
-C
4
)alkoxy or monohydroxy(C
1
-C
4
)alkoxy(C
1
-C
4
)alkoxy radical;
R
6
represents a hydrogen atom or a hydroxyl, amino or (C
1
-C
4
)alkyl radical;
R
7
represents a hydrogen atom or a (C
1
-C
4
)alkyl radical;
R
8
represents a hydrogen or halogen atom, such as chlorine, bromine, iodine or fluorine, or an amino radical;
R
9
represents a hydrogen atom or a hydroxyl, amino, (C
1
-C
4
)alkoxy, monohydroxy(C
1
-C
4
)alkoxy or polyhydroxy(C
2
-C
4
)alkoxy radical; at least two of the R
5
to R
9
radicals being other than a hydrogen atom, and the said composition being devoid of any enzymatic system capable of bringing about oxidation of the compounds of formula (I) and/or (II).
As indicated above, the dyeing composition in accordance with the invention results in powerful colourings which furthermore exhibit excellent properties of resistance with respect to the action of various external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
Another subject-matter of the invention is a process for the oxidation dyeing of keratinous fibres employing this dyeing composition.
The pyrazolo[1,5-a]pyrimidies of formula (I) which can be used as oxidation base in the dyeing composition in accordance with the invention are known compounds which are disclosed in Patent Application FR-A-2,750,048.
Mention may in particular be made, among the pyrazolo[1,5-a]pyrimidines of formula (I) which can be used as oxidation base in the dyeing compositions in accordance with the invention, of:
pyrazolo[1,5-a]pyrimidine-3,7-diamine;
2-methylpyrazolo[1,5-a]pyrimidine-3,7-diamine;
2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;
pyrazolo[1,5-a]pyrimidine-3,5-diamine;
2,7-dimethylpyrazolo[4,5-a]pyrimidine-3,5-diamine;
3-aminopyrazolo[1,5-a]pyrimidin-7-ol;
3-amino-5-methylpyrazolo[1,5-a]pyrimidin-7-ol;
3-aminopyrazolo[1,5-a]pyrimidin-5-ol;
2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol;
3-amino-7-(&bgr;-hydroxyethylamino)-5-methylpyrazolo[1,5-a]pyrimidine;
2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol;
2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol;
2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol;
5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;
2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;
2,5,N-7,N-7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine;
an
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner LLP
L'Oreal (S.A.)
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