Siloxane dyes, compositions containing same and uses thereof

Details Siloxane dyes, compositions containing same and uses thereof Siloxane dyes, compositions containing same and uses thereof

1998-09-17

2001-03-06

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From silicon reactant having at least one...

C528S028000, C528S038000, C008S407000, C008S414000, C514S844000, C424S064000

Reexamination Certificate

active

06197911

ABSTRACT:

The invention relates to compounds of diorganosiloxane type containing nitroaniline functionality, these compounds constituting a novel family of dyes which can be used in the cosmetics field.
Silicon-based dyes have already been described and proposed for coloring natural and synthetic organic fibres or inorganic materials. Such dyes, for instance those described in Belgian patents Nos. 875,160 and 875,230 or U.S. Pat. Nos. 2,925,313 and 2,963,338, are, however, reactive on account of hydrolysable groups which exist on the silicon atom, thereby possibly giving rise to a certain level of instability or undesirable change under certain conditions of use. This drawback is in addition to the molecular weight, which is sometimes difficult to control.
Polysiloxane dyes containing at least two chromophoric aromatic groups of azo or anthrone type in their chain are known from the prior art. Such dyes are described in U.S. Pat. No. 4,381,260.
In the cosmetics field, and in particular, for example, in hair dyeing, or in the manufacture of make-up products for the lips, the face, the eyelashes and the eyebrows, direct dyes are sought, that is to say dyes which modify the natural shade temporarily, which are of suitable harmlessness and which are stable, in particular with respect to light, to washing and to inclement weather.
The present invention is directed towards obtaining the said advantages, by providing novel compounds of the linear or cyclic diorganosiloxane type containing nitroaniline functionality, which are chemically and physically stable and which have a very good affinity for fibres, in particular for human keratin fibres such as the hair.
These novel compounds are also of suitable harmlessness, thereby making them particularly suitable for use as dyes in, or for the preparation of, cosmetic compositions intended for dyeing human keratin fibres and in particular the hair, or intended for make-up.
The subject of the present invention is thus compounds which are characterized in that they correspond to one of formulae (1) and (2) below:
in which formulae (1) and (2):
R, which may be identical or different, are chosen from C
1
-C
10
alkyl, phenyl and 3,3,3-trifluoropropyl radicals, at least 80%, on a number basis, of the radicals R being methyl,
B, which may be identical or different, are chosen from the above radicals R and the radical A defined below,
r is an integer between 0 and 50 inclusive, and s is an integer between 0 and 20 inclusive, with the condition that if s is zero then at least one of the two symbols B denotes A,
u is an integer between 1 and 6 inclusive and t is an integer between 0 and 10 inclusive, it being understood that t+u is equal to or greater than 3, and
the symbol A denotes a monovalent radical linked directly to a silicon atom, and which corresponds to formula (3) below:
in which formula (3):
Z is the divalent radical:
or hydrogen,
x is 1 or 2,
p represents an integer between 0 and 10 inclusive,
R
1
represents hydrogen or a C
1
-C
4
alkyl radical,
R
2
represents hydrogen or a C
1
-C
4
alkyl radical or the divalent radical Z defined above,
R
3
represents hydrogen or a radical NR
5
R
6
in which R
5
and R
6
represent hydrogen or a C
1
-C
4
alkyl radical, a C
2
-C
4
mono- or dihydroxyalkyl radical or the divalent radical Z, it being understood that at least one radical Z denotes a divalent radical:
R
4
represents hydrogen, an OH or halogen radical, a C
1
-C
4
alkyl radical or a C
1
-C
4
alkoxy radical.
In formulae (1) and (2) above, A thus represents the nitroaniline group which, after fixing to the starting silicone chain, imparts dyeing properties to the compounds of linear [formula (1)] or cyclic [formula (2)] diorganosiloxane type. The alkyl radicals may be linear or branched and chosen in particular from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and tert-octyl radicals. The preferred alkyl radicals R and B according to the invention are methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethylhexyl radicals. Even more preferably, the radicals R and B are all methyl radicals.
Among the linear or cyclic diorganosiloxanes falling within the scope of the present invention, random derivatives or derivatives in well-defined blocks having at least one, and even more preferably all, of the following characteristics:
R is alkyl and even more preferably is methyl,
B is alkyl and even more preferably methyl [case of the linear compounds of formula (1)],
r is between 0 and 3 inclusive; s is between 0 and 3 inclusive (case of the linear compounds of formula (1)),
t+u is between 3 and 5 [case of the cyclic compounds of formula (2)],
R
1
is hydrogen or methyl,
p is equal to 1,
x is 1 or 2,
R
2
and R
4
denote hydrogen,
R
3
is hydrogen or a radical NR
5
R
6
in which R
5
and R
6
represent hydrogen or a C
2
-C
4
mono- or dihydroxyalkyl radical,
and even more advantageously, all of the following characteristics:
R is alkyl and even more preferably is methyl,
B is alkyl and even more preferably methyl [case of the linear compounds of formula (1)],
Z is the divalent radical:
R
1
is hydrogen or methyl,
p is equal to 1,
r is zero and s is equal to 1 (case of the linear compounds of formula (1)),
u=1 and t=2 [case of the cyclic compounds of formula (2)],
x is 1 or 2,
R
2
and R
4
denote hydrogen,
R
3
is hydrogen or a radical NR
5
R
6
in which R
5
and R
6
represent hydrogen or a C
2
-C
4
mono- or dihyroxyalkyl radical
are more particularly preferred.
According to the invention, the compounds more particularly preferred are the following:
In order to prepare the siloxane dyes of formulae (1) and (2), the process may be carried out conventionally (route 1) using a hydrosilylation reaction, namely
starting with the corresponding silicone, in which, for example, all the radicals A are hydrogen atoms. This starting silicone is referred to hereinbelow as SiH-containing derivative; the SiH groups may be present in the silicone chain and/or at the ends of the silicone chain. These SiH-containing derivatives are products which are well known in the silicone industry and are generally commercially available. They are described, for example, in U.S. Pat. Nos. U.S. Pat. No. 3,220,972, U.S. Pat. No. 3,697,473 and U.S. Pat. No. 4,340,709.
This SiH-containing derivative may thus be represented either by formula (1b) below:
in which R, r and s have the meaning given above for formula (1) and the radicals B′, which may be identical or different, are chosen from the radicals R and a hydrogen atom,
or by formula (2b) below:
in which R, t and u have the meaning given above for formula (2).
A standard hydrosilylation reaction is thus carried out on this SiH-containing derivative of formula (1b) or (2b), this reaction being performed in the presence of a catalytically effective amount of a platinum catalyst, on a nitroaniline of formula (3b) below:
in which,
Z′ is the radical:
R
2
is hydrogen, C
1
-C
4
alkyl or the radical Z′,
R
3
is hydrogen, a radical NR
5
R
6
in which R
5
and R
6
represent hydrogen or a C
1
-C
4
alkyl radical, a C
2
-C
4
mono- or dihydroxyalkyl radical or the radical Z′,
x, p, R
1
and R
4
have the meaning given above for formula (3),
it being understood that at least one radical Z′ denotes:
Processes which are suitable for the preparation of the products of formula (3b) above are described in particular in patent application DE-42 40 684.
Another possible synthetic route (route 2) which is suitable for the preparation of the polysiloxane dyes of formulae (1) and (2) consists in starting from the derivatives corresponding to formula (1) or to formula (2) respectively in which all the radicals A are replaced by the radical of formula (10) below:
in which R
1
, R
2
and p have the same meaning as in formula (3).
The radicals of formula (10) may be present in the silicone chain and/or at the ends of the silicone chain. These st

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