Use of silicon compounds to dye human keratin fibres; novel...

Details Use of silicon compounds to dye human keratin fibres; novel... Use of silicon compounds to dye human keratin fibres; novel...

1999-09-29

2001-01-23

Diamond, Alan (Department: 1753)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S425000, C008S404000, C008S609000, C008S611000, C008S647000, C008S662000, C008S663000, C008S673000, C008S675000, C008S676000, C008S677000, C008S916000, C008SDIG001, C008S428000, C008S429000, C008S435000, C008S437000, C534S726000, C534S683000, C556S413000, C556S418000, C556S419000, C556S423000, C556S425000, C556S428000, C556S436000, C556S450000, C556S453000, C556S420000, C548S110000, C544S069000, C544S001000, C552S209000

Reexamination Certificate

active

06176885

ABSTRACT:

The invention relates to the use of linear or cyclic silicon compounds containing at least one chromophoric group of quinone or azo type as direct dyes in a dye composition intended for dyeing human keratin fibres and in particular the hair; the invention also relates to some of these silicon compounds as novel compounds.
Silicon dyes have already been described and proposed for dyeing synthetic fibres; such dyes are described in Belgian patent Nos. 875,160, 875,182 and 875,230, U.S. Pat. No. 2,925,313, German patent No. 2,918,685 and in European patent application No.455,595, the disclosures of which are specifically incorporated by reference herein.
Silicon dyes have also been described and proposed for dyeing silicone resins: see in this respect U.S. Pat. Nos. 3,838,891, 3,981,859 and 4,038,293, the disclosures of which are specifically incorporated by reference herein. Silicon dyes which can be used in the manufacture of photosensitive polymers are also known in the prior art: see German patent application No. 2,040,831, the disclosure of which is specifically incorporated by reference herein.
For most of them, these silicon dyes are reactive on account of hydrolysable groups carried in their structure, and they have never been proposed for use in cosmetics.
Moreover, certain unreactive but physically and chemically inert polysiloxane dyes of high molecular weight have been prepared, in the U.S. Pat. No. 4,381,260, the disclosure of which is specifically incorporated by reference herein, and proposed, on account of their stability, for uses such as the dyeing of natural textiles, of plastics, or for dyeing foodstuffs and pharmaceutical and cosmetic preparations.
However, in the field of hair dyeing, direct dyes are sought, that is to say dyes which, without supplying an oxidizing agent, are capable by themselves of temporarily modifying the natural shade of the hair. In this application, it is desired that the dyes satisfy a certain number of criteria; they will preferably be as inoffensive as possible, that is to say that they have an acceptable level of harmlessness, and they will preferably give rise to colorations that are sufficiently fast, in particular with respect to light, washing, perspiration and bad weather.
Among the direct dyes conventionally used in hair dyeing, quinone dyes such as those of anthraquinone, benzoquinone and naphthoquinone type and azo dyes are known. Not all of these dyes are entirely inoffensive, which is why, in hair cosmetics, dye molecules of this type with increasingly higher levels of performance in terms of harmlessness are sought.
Now, after considerable research conducted in this matter, the inventors have discovered that silicon compounds which contain at least one chromophoric group of quinone or azo type, and some of which are novel, make it possible to dye human keratin fibres such as the hair without an oxidizing agent, with the advantageous property of having an excellent level of harmlessness.
In addition, the hair colorations obtained using these compounds are faster than those produced with non-silicon compounds of quinone or azo type of the prior art.
This discovery forms the basis of the present invention.
The subject of the present invention is thus the use, as direct dyes in a dye composition intended for dyeing human keratin fibres and in particular the hair, of linear or cyclic silicon compounds containing at least one chromophoric group of quinone or azo type, characterized in that they correspond to one of the formulae (1), (2) or (3) 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%, in numerical terms, 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 condition that if s is zero 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,
in which formula (3):
R
1
, R
2
and R
3
, which may be identical or different, are chosen from linear or branched, saturated or unsaturated C
1
-C
8
alkyl and alkenyl radicals, and in which formulae (1), (2) and (3) the symbol A denotes a radical, which may be identical or different, of formula (4a), (4b), (4c) or (4d) below:
in which formulae (4a), (4b), (4c) and (4d):
R
4
, which may be identical or different, represent a linear or branched C
1
-C
6
alkyl radical, OH, C
1
-C
4
alkoxy, hydroxy(C
1
-C
4
)alkyl, COOH, CONH
2
, CN, SO
3
H, a halogen, an NO
2
radical, or a radical NR
5
R
6
in which R
5
and R
6
, which may be identical or different, denote a hydrogen atom, a C
1
-C
8
alkyl or hydroxy(C
1
-C
4
)alkyl or amino(C
1
-C
4
)alkyl radical, or form, together with the nitrogen atom to which they are attached, a 5- or 6-membered heterocycle which may be interrupted by an oxygen or sulphur atom,
m is an integer ranging from 0 to 2,
n is an integer equal to 1 or 2,
D is an —SO
2
NH—, —CONH— or —O— radical or a radical —NR
7
— in which R
7
is H or CH
3
,
W is a divalent radical of formula (5):
or of formula (6):
—HC═CH—(Z)
p
—  (6)
in which formulae (5) and (6):
R
8
denotes a hydrogen atom, a hydroxyl radical or a linear or branched, saturated or unsaturated C
1
-C
8
alkyl radical,
Z is a linear or branched C
1
-C
6
alkylene radical optionally substituted with an OH radical or a linear or branched, saturated or unsaturated C
2
-C
8
alkoxy radical, and
p is an integer equal to 0 or 1.
In formulae (1), (2) and (3) above, A thus represents a quinone (anthraquinone, naphthoquinone or benzoquinone) or azo group which, after attaching to the starting silicon chains, gives the compounds of formulae (1), (2) and (3) dyeing properties.
The alkyl radicals may be 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 alkyl radicals R and B which are preferred according to the invention are the 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 silicon compounds which may be used according to the present invention, random derivatives or derivatives with well-defined blocks having at least one, and even more preferably all, of the following characteristics:
R is alkyl and even more preferably methyl,
B is alkyl and even more preferably methyl,
r ranges from 0 to 3 and is more preferably zero,
s ranges from 1 to 3, more preferably equal to 1,
t+u ranges from 3 to 5,
R
1
, R
2
and R
3
are alkyl and even more preferably methyl,
R
8
is hydrogen, Z is methylene and p is equal to 1, are more particularly preferred.
According to the invention, the compounds more particularly preferred are the following:
4-(4-dimethylaminophenylazo)-N-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]-propyl]benzenesulphonamide [compound (7)]:
4-(4-dimethylaminophenylazo)-N-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]-propyl]benzamide [compound (8)]:
2-(4-methoxy-2-nitrophenylazo)-5-(3-trimethylsilanylpropoxy)phenol [compound (9)]:
2,5-bis[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propylamino]benzoquinone [compound (10)]:
2-chloro-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propylamino]-[1,4]-naphthoquinone [compound (11)]:
2-[3-[(1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propylamino]-[1,4]-naphthoquinone [compound (12)]:
1-hydroxy-4-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl

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