Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-11-10
2002-10-15
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S409000, C008S410000, C008S416000, C008S421000, C008S423000, C008S573000
Reexamination Certificate
active
06464732
ABSTRACT:
The present invention relates to a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, comprising at least one pyrazoline-4,5-dione and at least one aromatic or heteroaromatic primary amine, and to dyeing processes and devices using this composition.
For the dyeing of keratin fibres, and in particular human keratin fibres such as the hair, it is known practice to use dye compositions containing oxidation dye precursors, generally known as oxidation bases, which are colourless or faintly coloured compounds which, when combined with oxidizing products, give rise to coloured compounds and dyes by means of an oxidative condensation process.
It is also known how to vary the shades obtained with these oxidation bases, by combining them with couplers or coloration modifiers. The variety of molecules used as regards the oxidation bases and couplers makes it possible to obtain a wide variety of colours. The colourations obtained are generally intense with good properties in terms of resistance over time (fastness) in the face of external agents (light, bad weather, washing, permanent-waving, perspiration, friction). However, the development of the colour requires the presence of an oxidizing agent, most generally aqueous hydrogen peroxide solution, the consequences of which are more or less pronounced deterioration of the state of the fibre.
It is also known practice to dye keratin fibres with direct dyes which are applied under mild conditions and which, consequently, generally respect the state of the fibre. However, the shades obtained with these direct dyes are not particularly intense and often need to be enhanced. In addition, their resistance to external agents is not as good, in particular their resistance to washing, and it is often considered to be insufficient.
To overcome these various drawbacks, it has already been proposed to dye the hair without an oxidizing agent, with dye compositions comprising either (a) 2,3-indolinedione, also known as “isatin” or one of its derivatives, or (b) a 1,2-ethanedione derivative, or (c) a 1,3-propanedione derivative, or (d) an indolinone derivative, with one or more aromatic amines and/or amino acids and/or oligopeptides and/or amino sugars and/or phenolic derivatives.
Such dye compositions have been described in the following documents:
for 2,3-indolinedione and its derivatives: patents and patent applications US-4,750,408, EP-0,359,465, EP-0,497,697, EP-0,502,783, EP-0,502,784, EP-0,634,923, EP-0,750,490, DE-4,314,317, DE-4,314,318, DE-4,409,143,
for the 1,2-ethanedione derivatives: patent applications DE-4,317,855, DE-4,318,742, DE-4,335,625,
for the 1,3-propanedione derivatives: patent applications DE-4,335,626, DE-4,335,627, DE-4,335,628,
for the indolinone derivatives: patent application DE-4,335,623.
However, the colourations obtained using the said combinations are not always satisfactory, in particular as regards certain properties such as the sheen, the strength, the fastness and the selectivity. As regards selectivity, a good hair dye should be as homogeneous as possible from the root to the tip of the hair, in which case it is said to be unselective or relatively unselective.
However, hair colourations not comprising an oxidizing agent, such as direct colourations or the colourations obtained using the abovementioned combinations of isatin, 1,2-ethanedione, 1,3-propanedione or indolinone, generally have the drawback of being highly selective. There is thus a real need to have available hair dye compositions which contain no oxidizing agent, in order to respect the state of the fibre, and which give strong shades while being relatively unselective.
After considerable research conducted in this matter, the Applicant has now discovered, entirely surprisingly and unexpectedly, that varied shades which are both shiny, strong, fast and relatively unselective can be obtained by applying a dye composition containing at least one pyrazoline-4,5-dione of formula (I) and at least one aromatic or heteroaromatic amine of formula (II), which are defined below, to keratin fibres, in the absence of an oxidizing agent.
This discovery forms the basis of the presentinvention.
The present invention relates to a composition for dyeing keratin fibres, in particular human keratin fibres such as the hair, containing, in a medium which is suitable for dyeing, (i) at least one pyrazoline-4,5-dione of formula (I) and (ii) at least one aromatic or heteroaromatic amine of formula (II), which are defined below.
Another subject of the invention is a two-component composition for which, in a medium which is suitable for dyeing, one component contains at least one pyrazoline-4,5-dione of formula (I), the other component contains an aromatic or heteroaromatic amine of formula (II), formulae (I) and (II) being defined below, and which, being stored separately, are (i) mixed together at the time of use for application to the keratin fibres or (ii) applied sequentially to the said fibres.
A subject of the invention is also dyeing processes using these compositions.
Another subject of the invention relates to a multi-compartment device, or “kits”, for dyeing keratin fibres, characterized in that it comprises at least two compartments, one of which contains a composition containing, in a medium which is suitable for dyeing, at least one pyrazoline-4,5-dione of formula (I), and the other contains a composition containing, in a medium which is suitable for dyeing, at least one aromatic or heteroaromatic amine of formula (II) which can react without an oxidizing agent with the pyrazoline-4,5-dione of formula (I) to form a dye (formulae (I) and (II) being defined below.) However, other characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description which follows, as well as the various concrete, but in no way limiting, examples intended to illustrate it.
(i) The pyrazoline-4,5-diones according to the present invention are compounds of formula (I) below:
in which R
1
represents:
a hydrogen atom or a linear or branched C
1
-C6 alkyl radical optionally substituted with an OH, COOH, C
1
-C
4
alkoxy, C
1
-C
4
hydroxyalkyl or C
1
-C
4
dialkylamino radical,
a radical:
in which m =1, 2 or 3; n =1, 2 or 3; R
3
=hydrogen or methyl; R
4
=methyl, hydroxyl, linear or branched C
1
-C
5
alkoxy or linear or branched C
1
-C
5
hydroxyalkyl,
—a radical
in which p =1 or 2 and R
5
represents a substituted or unsubstituted phenyl radical,
a radical
in which q=1 or 2 and R
6
represents a thienyl, furyl, pyridyl or piperidyl radical or a phenyl radical which is unsubstituted or substituted with a maximum of 2 radicals chosen from methyl, trifluoromethyl, sulphonyl and methoxy radicals,
a phenyl radical which is unsubstituted or substituted with one to five radicals chosen from: —COOH, —CH
2
COOH, —NO2, —OH, —SO
3
H, —CH
2
OH, —OCF
3
, —CF
3
, —SO
2
CH
3
, —SO
2
NH
2
, —SO
2
NHC
2
H
5
, —SO
2
NHCH
2
CH
2
OH, —CON(CH
3
)2, —CON(C
2
H
5
)2, —CH
2
N(CH
3
)2, —CH
2
N(C
2
HS)2, —NHCOCH
3
, —NHCOC
2
H5, a halogen atom such as Cl, Br or F, a linear or branched C
1
-C
3
alkyl radical, a radical —Z—R
7
in which Z denotes O or S and R7 denotes H, and a linear or branched C
1
-C
3
alkyl radical,
a benzyl radical which is unsubstituted or substituted with a —COOH, —OCH
3
or —SO
3
H radical,
a pyridyl, pyrimidinyl, pyrazinyl, thiazinyl, benzothiazolyl, benzimidazolyl, thienyl, imidazolyl, thiazolyl, 1,2,4-triazolyl, indazolyl, indolyl, quinolyl or isoquinolyl radical, and R
2
represents:
a hydrogen atom or a linear or branched C
1
-C
6
alkyl radical optionally substituted with a hydroxyl or C
1
-C
4
alkoxy radical,
a phenyl radical which is unsubstituted or substituted with a halogen atom (Cl, Br or F), a nitro radical or a trifluoromethyl radical,
a phenyl radical substituted with a maximum of 3 radicals chosen from C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
dialkylamino and C
1
-C
2
alkylthio radicals,
a radical
in which r =1, 2 or 3 and R
8
Malle Gerard
Maubru Mireille
Vidal Laurent
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
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