Use of a screening silicone for protecting the color of...

Details Use of a screening silicone for protecting the color of... Use of a screening silicone for protecting the color of...

1997-10-15

2002-04-23

Dudash, Diana (Department: 1619)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Hair coloring

C424S070600, C424S070900, C424S070110, C424S070120, C424S070121, C424S059000, C424S401000, C008S406000

Reexamination Certificate

active

06375940

ABSTRACT:

The present application relates to the use of an organosiloxane bearing at least one ultraviolet-absorbing group in, and for the preparation of, a cosmetic or dermatological composition as an agent for protecting the colour of artificially coloured keratin fibres against the effects of UV radiation, in particular solar radiation.
It has been known for a long time that washing agents and light in particular have a tendency to attack the artificial colour of dyed hair. The hair colour thus obtained after a dyeing treatment gradually fades or turns to less attractive or desirable shades.
It has thus been found necessary to protect the colour of keratin fibres which have undergone a dyeing treatment, and in particular the colour of hair, and to substantially reduce the degradations associated with the action of external agents, in particular UV radiation and more particularly solar radiation.
The inventors have discovered, and this forms the subject of the invention, that screening silicones bearing ultraviolet-absorbing groups preserve, surprisingly, the colour of artificially coloured keratin fibres and in particular the hair, by substantially reducing the degradations associated with the action of UV radiation, in particular the action of solar radiation.
The subject of the invention is therefore the use of an organosiloxane bearing at least one ultraviolet-absorbing group in, and for the preparation of, a cosmetic or dermatological composition as an agent for protecting the colour of artificially coloured keratin fibres against the harmful effects of UV radiation, in particular solar radiation.
Other subjects will become apparent on reading the description and the examples which follow.
The organosiloxanes bearing ultraviolet-absorbing groups, which are used according to the invention, preferably contain in their molecule at least one unit of formula:
in which:
R′ denotes a saturated or unsaturated C
1
-C
30
hydrocarbon group, a C
1
-C
8
halogenated hydrocarbon group, an aromatic hydrocarbon group or a trimethylsiloxy group;
a=1 or 2;
T=—E—U where E represents a saturated or unsaturated, linear or branched aliphatic divalent hydrocarbon radical having at least 2 carbon atoms and optionally containing one or more oxygen atoms, or alternatively an aromatic group, and U represents the residue of a molecule which screens ultraviolet radiation.
In addition to the units of formula (I), the polyorganosiloxane may contain units of formula (II) and/or units of formula (III):
in which:
R′ and a have the same meanings as in formula (I);
b=1,2 or 3;
Z=—O—U, U having the same meaning as in formula (I).
As hydrocarbon group, mention may be made of C
1
-C
30
alkyl, C
2
-C
30
alkenyl or cycloalkyl radicals or aromatic radicals such as phenyl or toluyl.
As halogenated hydrocarbon group, mention may be made of the 3,3,3-trifluoropropyl radical.
In the organopolysiloxanes in accordance with the invention, comprising units of formula (I) and optionally units of formula (II) and/or of formula (III), preferably, at least 40%, in numerical terms, of the radicals R′ are methyl radicals. The total number of units (I), (II) and (III) is preferably less than or equal to 250 and ranges in particular from 2 to 50.
U preferably represents one of the following residues:
benzylidenecamphor optionally substituted on the benzene ring with hydroxyl or C
1
-C
8
alkyl or alkoxy radicals;
di(C
1
-C
8
)alkyl benzalmalonate optionally substituted on the benzene ring with hydroxyl or C
1
-C
8
alkyl or alkoxy radicals;
2-(2′-hydroxyphenyl)benzotriazole optionally bearing, on one of the aromatic rings, C
1
-C
8
alkyl or C
2
-C
8
alkenyl, halogen, alkoxy, carboxyl, hydroxyl, amino or tetraalkylpiperidyl substituents;
dibenzoylmethane optionally bearing C
1
-C
8
alkyl or alkoxy or hydroxyl radicals;
benzophenone optionally bearing C
1
-C
8
alkyl or alkoxy or hydroxyl radicals;
benzoate substituted with hydroxyl, C
1
-C
6
alkoxy, amino or mono- or di(C
1
-C
6
alkyl)amino radicals;
cinnamate optionally bearing hydroxyl, C
1
-C
6
alkyl or alkoxy, amino or mono- or di(C
1
-C
6
alkyl)amino radicals;
bis- or tris(phenylacrylate) optionally substituted with hydroxyl or C
1
-C
4
alkoxy radicals.
These organopolysiloxanes bearing ultraviolet-absorbing groups are described in particular in European patent applications Nos. 0,335,777, 0,305,059, 0,392,882, 0,392,883, 0,388,218, 0,350,314, 0,383,655, 0,389,337, 0,709,080 and 0,538,431, in International patent application WO 92/20690, in French patent applications Nos. 2,550,787 and 2,657,351 and in American patents U.S. Pat. Nos. 4,696,969, 4,554,369, 4,562,278, 3,513,184 and 4,859,759, the disclosures of which are specifically incorporated by reference herein.
Particularly preferred screening silicones of the invention are chosen from those containing a benzotriazole function, which correspond to the following formulae:
in which in 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 radicals R and the radical A,
r is an integer ranging from 0 to 50, and s is an integer ranging from 0 to 20, and if s=0, 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 linked directly to a silicon atom and corresponding to formula (3) below:
in which
Y, which may be identical or different, are chosen from C
1
-C
8
alkyl radicals, halogens and C
1
-C
4
alkoxy radicals, it being understood that, in the latter case, two adjacent Y groups of the same aromatic ring may together form an alkylidenedioxy group in which the alkylidene group contains from 1 to 2 carbon atoms,
X represents O or NH,
Z′ represents hydrogen or a C
1
-C
4
alkyl radical,
n is an integer ranging from 0 to 3,
m is 0 or 1,
p represents an integer ranging from 1 to 10.
As emerges from formula (3), given above, attachment of the chain unit —(X)
m
—(CH
2
)
p
—CH(Z′)—CH
2
— to the benzotriazole moiety, which thus ensures connection of the said benzotriazole moiety to the silicon atom of the silicon-containing chain, may, according to the present invention, take place in any of the available positions of the two aromatic rings of the benzotriazole:
This attachment preferably takes place in position 3, 4, 5 (aromatic ring bearing the hydroxyl function) or 4′ (benzene ring adjacent to the triazole ring) and, even more preferably, in position 3, 4 or 5. In a preferred embodiment of the invention, the attachment takes place in position 3.
Similarly, the substituent moiety or moieties Y may be attached in any of the other available positions on the benzotriazole. However, this attachment preferably takes place in position 3,4,4′,5 and/or 6. In a preferred embodiment of the invention, attachment of the moiety Y takes place in position 5.
In the above formulae (1) and (2), 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 according to the invention are methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethyhexyl radicals. Even more preferably, the radicals R are all methyl radicals.
These screening silicones are described, along with the process for their synthesis, in application EP-A-0,392,883 and in application WO 94/06404, the disclosures of which are specifically incorporated by reference herein.
Among the compounds of formula (1) or (2) above, it is preferred to use those corresponding to formula (1), that is to say diorganosiloxanes with a short linear chain.
Among the compounds of formula (1) above, it is preferred to use those in which th

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