Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
1999-01-06
2001-11-27
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S070100, C514S404000, C514S406000, C514S407000, C548S366400, C548S369400, C548S371100
Reexamination Certificate
active
06322775
ABSTRACT:
The present invention relates to novel cosmetic compositions, in particular for colouring the skin and/or the hair, these compositions comprising, in a cosmetically acceptable support, at least one 4,5-pyrazolinedione.
The invention also relates to novel 4,5-pyrazolinediones, to processes for their preparation and to their use in the cosmetics field, in particular for colouring the skin and more particularly in order to give the skin a tanned appearance.
It is known that dihydroxyacetone, or DHA, is a particularly advantageous product commonly used in cosmetics as an agent for artificially tanning the skin; when applied to the skin, in particular to the face, it affords a tanning or browning effect which is very similar in appearance to that which can result from prolonged exposure to the sun (a natural tan) or under a UV lamp. Such a use also has the advantage of entirely avoiding the risks of skin reaction generally associated with the above mentioned prolonged exposures (erythema, burning, loss of elasticity, appearance of wrinkles, premature ageing of the skin, and the like).
However, the use of DHA has certain drawbacks.
For instance, although the colour produced on the skin by applying a composition containing DHA is very close to that obtained in a natural tan, certain users may still consider it to be too yellow.
Other drawbacks also appear during the storage of compositions containing DHA. Thus, DHA has an annoying tendency, which may be more or less pronounced depending on the nature of the medium in which it is formulated, to degrade over time, this degradation generally leading in the long term to an undesirable yellowing of the compositions containing it. It also occurs that over time such compositions have a nauseating odour. Lastly, the pH of compositions containing DHA decreases over time, making them in the long run incompatible with use by topical application. These various phenomena have the effect of greatly reducing the activity of DHA, and in particular its ability to colour the skin, when these compositions are applied to the skin.
Moreover, the intensity of the coloration obtained on the skin, and especially the speed with which this coloration develops, are often considered to be insufficient by users of DHA-based self-tanning products, since the time required for the desired intensity to appear on the skin is generally several hours.
In order to increase the speed of appearance of the colour due to DHA, it has been sought to combine it with other substances. Thus, patent application EP-A-547,864 proposes to provide DHA in the presence of an amino acid and a silicone, the DHA and the amino acid being stored in separate compartments before they are applied to the skin. Mention may also be made of patent application WO-A-94/04130 which describes a device for supplying DHA at the same time as a primary amine, these two compounds also being stored in separate compartments.
However, these devices have the drawback of being complicated and of not giving any real improvement as regards the waiting time required in order to obtain satisfactory coloration of the skin. Lastly, in addition, they do not totally solve the problems due to the storage of compositions containing DHA.
In conclusion, it appears that DHA as an agent for artificially colouring the skin is not completely satisfactory and that there is thus a need for other agents which, preferably, do not have any of the disadvantages mentioned above.
To this end, novel compositions are now proposed containing, in a cosmetically acceptable support, at least one 4,5-pyrazolinedione. The time required to develop the colour after these compositions are applied to the skin is remarkably short. These compositions also have excellent stability and give the skin a colour very close to that present in a natural tan. Lastly, the staying power of the coloration on the skin is also noteworthy.
Moreover, these compositions find an advantageous application in dyeing hair.
A first subject of the invention is thus a novel composition comprising, in a cosmetically acceptable support, at least one 4,5-pyrazolinedione corresponding to formula (I) below:
in which R
1
is chosen from:
a hydrogen atom; a linear or branched C
1
-C
18
alkyl radical optionally substituted with a hydroxyl (OH), sulphonyl (SO
3
H), carboxyl (COOH) or C
2
-C
4
hydroxyalkyl radical; a cyclohexyl or cyclopentyl radical;
in which m is equal to 1, 2 or 3, n is equal to 1, 2 or 3, X is a hydrogen atom or a methyl radical, and Y is a methyl, hydroxyl or linear or branched C
1
-C
5
alkoxy radical;
a radical —(CH
2
)
p
—OR′ in which R′ represents a substituted or unsubstituted phenyl or naphthyl radical and p is equal to 1 or 2;
a radical —(CH
2
)
q
—R″ in which q is equal to 1, 2 or 3 and R″ is chosen from:
a phenyl radical which is unsubstituted or substituted with not more than 2 radicals chosen from methyl, trifluoromethyl, methoxy and sulphonyl radicals;
a naphthyl radical, a thienyl radical, a furyl radical, a pyridyl radical or a piperidyl radical;
a phenyl radical; a phenyl radical substituted with a nitro radical; a phenyl radical substituted with one to three radicals chosen from: —COOH, —CH
2
COOH, —Cl, —Br, —F, —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
H
5
)
2
, —NHCOCH
3
, —NHCOC
2
H
5
, a C
1
-C
8
alkyl radical or a radical —ZR
3
in which z is an oxygen or sulphur atom and R
3
is a hydrogen atom or a linear or branched C
1
-C
18
alkyl radical;
a naphthyl radical optionally substituted with an —SO
3
H radical;
a benzyl radical; a benzyl radical substituted with a —COOH, —OCH
3
or —SO
3
H radical;
a pyridyl radical, a pyrimidinyl radical, a pyrazinyl radical, a triazinyl radical, a benzotriazolyl radical, a benzimidazolyl radical, a thienyl radical, an imidazolyl radical, a thiazolyl radical, a 1,2,4-triazolyl radical, an indazolyl radical, an indolyl radical, a quinolyl radical or an isoquinolyl radical;
and R
2
is chosen from:
a hydrogen atom; a linear or branched C
1
-C
6
alkyl radical; a C
1
-C
4
hydroxy alkyl radical; a methoxymethyl radical;
a phenyl radical; a phenyl radical substituted with a halogen atom, a nitro radical or a trifluoromethyl radical; a phenyl radical substituted with not more than three radicals chosen from C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C-C
4
dialkylamino and C
1
-C
2
alkylthio radicals;
a benzyl radical; a benzyl radical substituted with a halogen atom, a C
1
-C
4
alkyl radical, a C
1
-C
4
alkoxy radical, a trifluoromethyl radical or a C
1
-C
4
dialkylamino radical;
a radical —(CH
2
)
r
—R
4
in which r is equal to 1, 2 or 3 and R
4
is chosen from:
an —SO
3
H radical, a C
1
-C
2
alkylthio radical or a benzylthio radical;
a methoxycarbonyl or ethoxycarbonyl radical;
a phenyl radical;
a C
1
-C
4
alkoxy radical or a phenoxy radical optionally substituted with one or more halogen atoms;
a C
1
-C
4
alkoxy radical; a trifluoromethyl radical; an acetamido radical; a C
1
-C
4
dialkylamino radical; a carboxyl radical; a methoxycarbonyl radical; an ethoxycarbonyl radical;
a thienyl radical, a furyl radical, a pyridyl radical or a pyrazolyl radical.
In a preferred embodiment of the invention, these compositions are intended to artificially tan the skin.
These novel compositions have the advantage of giving the skin a tan which is very close to a natural tan, and doing so in an extremely short time. Indeed, a few minutes are sufficient to obtain a tanned complexion.
The subject of the present invention is also a cosmetic treatment process for the skin which is intended to artificially tan and/or brown it, this process consisting in applying an effective amount of a cosmetic composition in accordance with the invention or a 4,5-pyrazolinedione as mentioned above to the skin.
The subject of the present invention is also the use of a 4,5-pyrazolinedione as mentioned above in, or for the manufacture of, compositions intended to artificially tan and/or b
Malle Gerard
Vidal Laurent
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
Patel Sudhaker B.
Shah Mukund J.
LandOfFree
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