Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
1999-07-23
2001-11-27
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S062000, C424S070100, C514S937000, C514S938000, C514S759000
Reexamination Certificate
active
06322800
ABSTRACT:
The present invention relates to the use of a fluorohydrocarbon compound in an emulsion, in particular as a stabilizing agent or as an essential compound of the fatty phase. The invention also relates to a composition comprising the emulsion, in particular a cosmetic, hygiene or pharmaceutical composition.
The use of perfluoropolyethers is known, in particular in the field of cleansing, protecting and making up the skin or hair. These compounds are known for their low surface tension and their ease of spreading, but they have a greatly reduced solubility in the majority of fluids, except in fluorinated fluids, which makes their formulation in cosmetics very difficult. Some of these compounds, particularly perfluoro(methyl isopropyl ether)s, are known under the name of FOMBLIN HC and are marketed by Montefluo.
Fluorohydrocarbon compounds exhibiting good solubility, in particular in conventional solvents, are known, for example, from the document FR 2,684,668. They make it possible to obtain stable and homogeneous emulsions. The thermodynamic stability of the emulsions comprising these compounds, in particular when they make up the whole of the fatty phase, could especially be improved.
The Inventors were faced with the problem of further improving the quality and the stability of the emulsions, whatever the nature of the oils employed.
The aim of the present invention is to provide fluorohydrocarbon compounds for the preparation of an emulsion of improved quality and stability with respect to those known in the state of the art. The fluorohydrocarbon compounds of the invention can indeed be incorporated as a stabilizing agent for an emulsion containing at least one fatty phase and one aqueous phase. They can in addition be used as an essential constituent of the fatty phase of an emulsion.
The subject of the invention is the use of at least one compound of formula (I):
R
F
—C
2
H
4
—O—CO—R
H
(I)
in which: R
F
represents a linear or branched perfluorinated alkyl-group having from 4 to 20 carbon atoms, and
R
H
represents a linear or branched alkyl group having from 1 to 29 carbon atoms,
in and/or for the preparation of a stable emulsion containing at least one fatty phase and one aqueous phase.
A further subject of the invention is the use of at least one fluorohydrocarbon compound of formula (I) as a stabilizing agent in an emulsion containing at least one fatty phase and one aqueous phase.
It has in fact been observed that the presence of at least one compound of formula (I) or of a mixture of these compounds when more than one compound of formula (I) is used, in an emulsion, and in particular in the fatty phase of the emulsion, can make it possible to improve the stability of the said emulsion, whatever the chemical nature of the fatty phase employed.
For the compounds of formula (I), the R
F
radical can preferably represent a perfluorinated alkyl group having from 4 to 10 carbon atoms and the R
H
radical a linear or branched alkyl group having from 1 to 15 carbon atoms.
Mention may be made, among the compounds of formula (I) which can be used in the emulsion according to the invention, of 2-(F-octyl)ethyl hexanoate, 2′-(F-hexyl)ethyl 2-butyloctanoate, 2′-(F-hexyl)ethyl 2-ethylhexanoate, 2-(F-octyl)ethyl 2-decyltetradecanoate, 2-(F-hexyl)ethyl octanoate, 2-(F-octyl)ethyl octanoate, 2-(F-octyl)ethyl octadecanoate, 2-(F-octyl)ethyl docosanoate, and 2-(F-octyl)ethyl decanoate.
When the compound of formula (I) is used as stabilizing agent, it can be present in the emulsion, preferably in the fatty phase, in the proportion generally ranging from 0.1 to 30% by weight, and preferably ranging from 0.5-20% by weight.
The fatty phase of the emulsion can additionally comprise at least one oil that can be chosen in particular from hydrocarbon oils that are optionally fluorinated, silicone oils and perfluorinated oils, alone or as a mixture.
The compound of formula (I) can be present in the composition in an amount generally ranging from 0.01 to 60% by weight, and preferably from 0.1 to 20% by weight, with respect to the total weight of the composition.
Another subject of the invention is the use of at least one compound of formula (I) as an essential constituent of the fatty phase of an emulsion.
It has indeed been surprisingly observed that the fact that the fatty phase comprises essentially at least one compound of formula (I), or a mixture of compounds of formula (I), can make it possible to thermodynamically stabilize the emulsion with time.
Another subject of the invention is an emulsion comprising at least one fatty phase and one aqueous phase, the fatty phase being composed essentially of at least one fluorohydrocarbon compound of formula (I).
The present invention also relates to a cosmetic, hygiene or pharmaceutical, including food, composition comprising an emulsion containing at least one aqueous phase and one fatty phase composed essentially of at least one compound of formula (I). “Composed essentially of” is understood to mean in the present description that the fatty phase comprises the compound of formula (I), or a mixture of compounds of formula (I), as the sole liquid oil, the compound preferably representing at least 50% by weight of the fatty phase; the fatty phase can then comprise 0-50% of conventional lipophilic additives other than oils. The compound of formula (I), or a mixture of these compounds, preferably represents at least 75% by weight of the fatty phase.
Whatever the use of the compound of formula (I), the fatty phase of the emulsion can comprise fat-soluble additives conventionally used in the field of application, such as vitamins, fragrances, fatty acids, waxy lipids, and in particular, ceramides.
The aqueous phase of the emulsions of the invention can also comprise conventionally-used hydrophilic additives, such as glycerol and urea.
The aqueous phase/oily phase ratio in the emulsions can range from 9 to 0.1 and preferably from 5 to 1.5. The emulsion can thus be provided in the water-in-oil or oil-in-water form or indeed in the form of a multiple emulsion.
The emulsions according to the invention can be used as a composition, or in a composition, in particular in the cosmetic, hygiene and pharmaceutical or indeed food fields. The composition can be provided in particular in the form of a gel, a milk or a cream.
In particular, the composition can be provided in the form of a product intended for making up and/or for caring for the skin or keratinous substances or alternatively in the form of a product for dyeing the hair or of a product for protecting the skin and/or keratinous substances from the sun.
The compositions in accordance with the invention can comprise any additive commonly used in the field under consideration, such as surfactants, moisturizing agents, organic solvents, silicones, thickeners, emollients, sunscreens, treating agents, anti-foaming agents, fragrances, preservatives, antioxidizing agents, sequestrants, flavouring agents, basifying or acidifying agents, fillers and pigments, emulsifiers or coemulsifiers.
The compound of formula (I) can be prepared according to a conventional esterification process that comprises mixing, in acid medium, preferably in the presence of a solvent, an acid of formula R
H
—COOH with an alcohol of formula R
F
—C
2
H
4
—OH in which the R
H
and R
F
radicals have the same meanings as above.
Another esterification process for preparing the compound of formula (I) comprises reacting an alcohol of formula R
F
—C
2
H
4
—OH with an activated acid derivative of formula R
H
—CO—Y in which R
H
has the same meaning as above and Y represents an activating group, in particular of halogen, mixed or symmetrical anhydride residue or imidazole type.
The invention will now be described in greater detail by means of the following examples, which are given solely by way of illustration and in no way limit the invention. Examples 1 to 7 describe a process for the preparation of compounds used in the context of the present invention.
REFERENCES:
patent: 3993744 (1976-11-01), Cella et al.
paten
Bollens Eric
Dardenne Agnés
Henrion Jean-Christophe
Nicolas-Morgantini Luc
Philippe Michel
Channavajjala Lakshmi
Finnegan Henderson Farabow Garrett & Dunner LLP
L'Oreal (S.A.)
Page Thurman K.
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