Use of a volatile polyfluorinated solvent as an antitransfer...

Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations

Reexamination Certificate

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C424S063000, C424S064000, C424S069000, C424S070700, C424S401000, C514S747000, C514S759000, C514S845000, C514S938000

Reexamination Certificate

active

06224851

ABSTRACT:

The present invention relates to the use of a certain class of volatile polyorganohalogen compounds, in which the halogen atom is a fluorine, in antisun or make-up or sun-screen cosmetic compositions in order to avoid so-called transfer phenomena.
In cosmetic compositions of this type, the term transfer means the displacement of a fraction of the composition by contact with another support, whether of the same nature or of different nature. Thus, when they are intended for make-up, such as eyeshadows, eyeliners or mascaras, they can be transferred onto the hands by rubbing or by contact of the hands with the eyes. When these compositions are lipsticks, they can be transferred onto the teeth, the hands or onto the cheeks of another person.
Irrespective of the type of composition they are, they can also, by transfer, stain napkins and leave imprints on glasses, cups and other containers.
In addition, when the compositions are foundations, the foundation can also transfer onto shirt collars and thus stain them.
In addition to this transfer problem, make-up compositions can also exhibit migration phenomena, i.e. the compositions have a tendency to travel inside the wrinkles and/or fine lines on the skin, in particular in the case of foundations, in the fine lines around the lips in the case of lipsticks, and in the folds of the eyelids in the case of eyeshadows.
These transfer and migration phenomena are particularly detrimental since they give rise to an aesthetically unappealing effect and to a certain number of drawbacks as mentioned above.
In order to overcome this, it has already been proposed, in particular in U.S. Pat. No. 5,505,937, to use volatile oils, in particular cyclic silicones, as well as hydrocarbon-based products such as C
8
-C
20
-iso-paraffins combined with a silicone resin and with waxes.
Although this type of make-up composition makes it possible to avoid the transfer phenomena, there is nevertheless formation of a dry film on the skin, this film consisting of waxes and pigments with a matt appearance, which is associated with a surface state of the heterogeneous film.
It has also been proposed to make transfer-resistant make-up products, by using aqueous dispersions of hydrophobic polymers or latices, which, after drying on the skin, give a dry film which can have a certain level of sheen.
Nevertheless, the drawback of these aqueous dispersions of hydrophobic polymers is associated with a level of discomfort and a difficulty in applying them to the skin, in particular to the lips in the case of lipsticks.
After many studies on various types of compounds, it has been observed, surprisingly and unexpectedly, that by using a certain class of volatile polyorganohalogen solvents in which the halogen atom is fluorine, it is possible to overcome, in a particularly satisfactory and effective manner, the drawbacks arising due to the transfer and migration problems.
Another particularly appreciable advantage is to be able to obtain the compositions in total safety, since these solvents, referred to hereinbelow as volatile polyfluorinated solvents, have no flash point, which allows the compositions to be prepared at high temperature, and thus has a certain advantage when substances with a melting point above room temperature are used.
Lastly, the use of volatile polyfluorinated solvents makes it easier to incorporate high concentrations of non-volatile fluorinated derivatives into the compositions, these derivatives being entirely miscible with the volatile polyfluorinated solvents. A highly fluorinated, shiny or satin residual film which is water-resistant and fat-resistant can thus be obtained.
The subject of the present invention is thus the use, in a make-up or sun-screen cosmetic composition containing particles of pigment and/or of filler, of at least one volatile polyorganohalogen solvent, as anti-transfer agent, the halogen atom being fluorine and the said solvent having a vapour pressure of greater than 20 mba (2000 Pa) at 25° C. and preferably greater than 40 mba (4000 Pa).
Among the volatile polyfluorinated solvents which can be used according to the invention and which satisfy the vapour pressure criterion mentioned above, mention may be made in particular of:
1) the perfluorocycloalkyl compounds corresponding to the formula (I) below:
in which:
n is 3, 4 or 5,
m is 1 or 2, and
p is 1, 2 or 3
with the proviso that when m=2, the groups are not necessarily alpha to each other,
2) the fluoroalkyl or heterofluoroalkyl compounds corresponding to formula (II) below:
CH
3
—(CH
2
)
n
—[Z]
t
-
X
—CF
3
  (II)
in which:
t is 0 or 1,
n is 0, 1, 2 or 3
X is a linear or branched divalent perfluoroalkyl radical containing from 2 to 5 carbon atoms, and
Z represents O, S or NR, R being hydrogen, a radical —(CH
2
)
n
-CH
3
or —(CF
2
)
m
—CF
3
, m being 2, 3, 4 or 5,
3) the perfluoroalkane compounds corresponding to formula (III) below:
CF
3
—(CF
2
)
n
—CF
3
  (III)
in which:
n is 2 to 6, and
4) the perfluoromorpholine derivatives corresponding to formula (IV) below:
in which:
R represents a C
1
-C
4
perfluoroalkyl radical.
Among the perfluorocycloalkyl compounds of formula (I), mention may be made in particular of perfluoromethylcyclopentane and perfluorodimethylcyclohexane, which are respectively sold under the names Flutec PC1® and Flutec PC3® by the company BNFL Fluorochemicals Ltd., and perfluorodimethylcyclobutane.
Among the fluoroalkyl or heterofluoroalkyl compounds of formula (II) mention may be made in particular of methoxynonafluorobutane, sold under the name HFE7100 by the Company 3M, and ethoxynonafluorobutane sold under the name HFE-7200® by the company 3M.
Among the perfluoroalkane compounds of formula (III), mention may be made in particular of dodecafluoropentane and tetradecafluorohexane.
Among the perfluoromorpholine derivatives of formula (IV), mention may be made in particular of 4-trifluoromethylperfluoromorpholine and 4-pentafluoroethylperfluoromorpholine.
The volatile polyfluorinated solvents as defined above must also satisfy the criterion of the boiling point, which needs to be between 20 and 75° C. and preferably between 25 and 65° C.
In the make-up or sun-screen compositions, the proportion of volatile polyfluorinated solvent is generally between 2 and 98% by weight, but preferably between 5 and 70% by weight, relative to the total weight of the composition.
The pigments in the make-up or sun-screen compositions and the fillers are in the form of very fine particles with an average particle size of between about 0.02 and about 50 &mgr;m.
The pigments in the compositions can be inorganic or organic or alternatively in the form of metal lakes. Among these pigments, mention may be made of titanium dioxide, zinc oxide, D&C Red No. 36 and D&C Orange No. 17, the D&C Red Nos. 7, 11, 31 and 34 calcium lakes, the D&C Red No. 12 barium lake, the D&C Red No. 13 strontium lake, the FD&C Yellow No. 5, FD&C Yellow No. 6, D&C Red No. 27, D&C Red No. 21 and FD&C Blue No. 1 aluminum lakes, iron oxides, manganese violet, chromium oxide and ultramarine blue.
The fillers can be of natural or synthetic origin. Among these, mention may be made in particular of:
a) inorganic powders such as talc, kaolin, mica, silica, silicates, alumina, zeolites, hydroxyapatite, sericite, titanium micas, barium sulphate, bismuth oxychloride, boron nitride and metal powders such as aluminium powder;
b) plant powders such as cereal starch powder, corn powder, potato starch powder or rice powder;
c) organic powders such as nylon powder, polyamide powder, polyester powder, polytetrafluoroethylene powder or polyethylene powder.
These various powders can also be coated, for example, with metal salts of fatty acids, amino acids, lecithin, collagen, silicone compounds or fluoro compounds, or with any other common coating agent.
In addition to the pigments as defined above, the compositions also contain at least one dye, and, among these, mention may be made of eosin derivatives such as D&C Red No. 21 and halogenated fluoroscein derivatives such as D&C Re

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