Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2001-02-07
2003-12-23
Travers, Russell (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S063000, C556S422000
Reexamination Certificate
active
06667343
ABSTRACT:
The invention relates to diorganosiloxane compounds containing at least one nitroaniline function, 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 fibers or inorganic materials. Such dyes, for instance those described in Belgian Patent Nos. 875,160 and 875,230 or U.S. Pat. Nos. 2,925,313 and 2,963,338, may, however, be reactive because 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, 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, i.e., 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 at least one such advantage, by providing novel linear or cyclic diorganosiloxane compounds containing at least one nitroaniline function, which are chemically and physically stable and which have a very good affinity for fibers, in particular for human keratin fibers such as the hair.
These novel compounds may also be 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 fibers 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 ranging from 0 to 50, and s is an integer ranging from 0 to 20, with the proviso that if s=0 then at least one of the two symbols B denotes A,
u is an integer ranging from 1 to 6 and t is an integer ranging from 0 to 10, it being understood that t+u is equal to or greater than 3, and
the symbol A denotes a monovalent radical attached directly to a silicon atom, and which corresponds to formula (3) below:
in which formula (3):
Z is chosen from hydrogen and the divalent radical:
x is 1 or 2,
p is an integer ranging from 0 to 10,
R
1
is chosen from hydrogen and a C
1
-C
4
alkyl radical,
R
2
is chosen from hydrogen, a C
1
-C
4
alkyl radical and the divalent radical Z defined above,
R
3
is chosen from hydrogen and a radical NR
5
R
6
in which R
5
and R
0
, which may be identical or different, are chosen from hydrogen, C
1
-C
4
alkyl radicals, C
2
-C
4
monohydroxyalkyl radicals, C
2
-C
4
dihydroxyalkyl radicals, and the divalent radical Z, it being understood that, in the context of NR
5
R
6
, said at least one radical
as defined above,
R
4
is chosen from hydrogen, a hydroxy radical, a halogen radical, a C
1
-C
4
alkyl radical and 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 linear (formula (1)) or cyclic (formula (2)) diorganosiloxane compounds. A is attached to the starting silicone chain via the substituent Z, which therefore must be attached directly to a silicone atom in the chain of either formula (1) or (2),
The alkyl radicals defined above for R and B 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. In one embodiment of the present invention, the preferred alkyl radicals R and B according to the invention may be chosen from methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethylhexyl radicals. In another embodiment, the radicals R and B are all methyl radicals.
Among the linear or cyclic diorganosiloxanes falling within the scope of the present invention, are random derivatives or derivatives in well-defined blocks having at least one, and in certain embodiments all, of the following characteristics:
R is alkyl such as methyl,
B is alkyl such as methyl (case of the linear compounds of formula (1)),
r ranges from 0 to 3; s ranges from 0 to 3 (case of the linear compounds of formula (1)),
t+u ranges from 3 to 5 (case of the cyclic compounds of formula (2)),
R
1
is chosen from hydrogen and methyl,
p is equal to 1,
x is 1 or 2,
R
2
and R
4
are both hydrogen,
R is chosen from hydrogen and a radical NR
5
R
6
in which R
5
and R
6
, which may be identical or different, are chosen from hydrogen, C
2
-C
4
monohydroxyalkyl radicals, and C
2
-C
4
dihydroxyalkyl radicals, and in one embodiment, all of the following characteristics:
R is alkyl, such as methyl,
B is alkyl, such as methyl (case of the linear compounds of formula (1)),
Z is the divalent radical:
R
1
is chosen from hydrogen and 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
are both hydrogen,
R
3
is is chosen from hydrogen and a radical NR
5
R
6
in which R
5
and R
6
, which may be identical or different, are chosen from hydrogen, C
2
-C
4
monohydroxyalkyl radicals, and C
2
-C
4
dihydroxyalkyl radicals.
According to the invention, the compounds can be chosen from the following:
Other exemplary compounds corresponding to formulae (1) and 2 include the following compounds (12)-(14), which represent compounds of formula (1), wherein the substituent A is represented by formula (3). In Formula (12), R
2
is equal to Z. Accordingly, the nitrogen atom of formula (3) can be linked to two silicone chains via two divalent radicals Z, as can be seen in Formula (12). In Formula (13), R
5
is Z, and in Formula (14), R
5
and R
6
are both Z, illustrating that the nitrogen atom of NR
5
R
6
can be linked to one or two silicone chains via one or two radicals Z.
wherein the silicone polymer is a compound selected form formula (1) and formula (2).
In order to prepare the slioxane 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 a 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. 3,220,972, 3,697,473 and 4,340,709, the disclosures of which are hereby incorporated by reference.
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
Lagrange Alain
Leduc Madeleine
Richard Herve
L'Oreal
Travers Russell
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