Title:  Stable gelled composition containing lipophilic active agents sensitive to oxygen and/or water

United States Patent:  6,150,422

Assignee:  L'Oreal (Paris, FR)

Filed:  March 11, 1997

Foreign Application Priority Data:  Mar 12, 1996[FR] (96 03096)

A stable gelled composition, containing at least one lipophilic active agent sensitive to oxygen or to water or to both, and a solvent which contains, as gelling agent, at least one polysaccharide alkyl ether formed of units containing at least two different glycoside rings, each unit containing at least one hydroxyl group substituted with a saturated hydrocarbon alkyl group.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention generally relates to a stable gelled composition containing a lipophilic active agent sensitive to oxygen and/or to water, intended, in particular, for use in the cosmetic and/or dermatological fields. The present invention also relates to a use of this composition for treating the skin.

The present stable gelled composition contains at least one lipophilic active agent sensitive to oxygen and/or to water, and a solvent, which composition contains, as a gelling agent, at least one polysaccharide alkyl ether formed of units containing at least two different glycoside rings, each unit containing at least one hydroxyl group substituted with a saturated hydrocarbon alkyl chain.

By virtue of this specific gelling agent, the present composition is particularly stable over time and no significant degradation of the active agent sensitive to oxygen and/or to water, in particular retinol, is observed.

Accordingly, another important aspect of the present invention entails the use of a polysaccharide alkyl ether formed of units containing at least two different glycoside rings, each unit containing at least one hydroxyl group substituted with a saturated hydrocarbon alkyl chain, to stabilize a lipophilic active agent sensitive to oxygen and/or to water.

Active agents sensitive to oxygen and/or to water, which may be used in accordance with the present invention, are, for example, in addition to retinol, retinol derivatives such as .beta.-carotene, retinol palmitate or acetate, flavonoids or polyunsaturated fatty acids.

According to a particular embodiment of the present invention, the polysaccharide alkyl ether has a molecular weight greater than about 100,000, and preferably greater than about 200,000. Each unit preferably contains from one to six, and more preferably, from two to four hydroxyl groups substituted with a saturated hydrocarbon alkyl chain.

The term "saturated hydrocarbon alkyl chain or group" is understood and used herein to mean a chain containing from 1 to about 24, preferably from 1 to about 10, and more preferably from 1 to about 5 carbon atoms. In particular, the alkyl chain or group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl or n-pentyl.

The glycoside rings may be, for example, mannose, galactose, glucose, furanose, rhamnose or arabinose.

According to a preferred embodiment of the present invention, the polysaccharide alkyl ether is an alkyl ether of a gum and more particularly of a gum which is nonionic overall, that is to say which is practically without an ionic group. As appropriate gums, there may be mentioned, for example, guar gum whose unit contains galactose and mannose, carob gum whose unit contains galactose and mannose, karaya gum which is a complex mixture of rhamnose, galactose and galacturonic acid, tragacanth gum which is a complex mixture of arabinose, galactose and galacturonic acid.

According to a preferred embodiment of the present invention, the polysaccharide alkyl ether is a derivative of guar gum, and, more particularly, ethylated guar having a degree of substitution of about 2 to 3, in particular 2.5, as described in RD 95378007 (October 1995).

The composition according to the present invention may contain, for example, a quantity of polysaccharide alkyl ether ranging from about 0.5 to 10%, and preferably from about 2 to 8% of the total weight of the composition.

The lipophilic active agent sensitive to oxygen and/or to water is present in the present composition in a quantity ranging from about 0.001 to 20%, preferably from about 0.01 to 5% and better still from about 0.2 to 1% of the total weight of the composition.

In the composition according to the present invention, there may be used any organic solvent capable of dissolving the lipophilic active agent sensitive-to oxygen and/or to water while preserving its good stability. The term "solvent" is understood and used herein to mean both hydrocarbon solvents and oils. The solvent may be chosen especially from fatty alcohols, fatty esters, oils of plant origin and/or mixtures thereof, as well as mixtures of these solvents with silicone and/or mineral oils. In particular, the solvent is one or more of aliphatic fatty alcohols having a straight or branched C₁₆ -C₂₀ chain, diesters of a C₆ -C₁₄ dicarboxylic acid and of isopropyl alcohol, triglycerides of a C₆ -C₁₈ fatty acid and mixtures thereof.

Among the C₁₆ -C₂₀ aliphatic fatty alcohols which may be used in the present invention, there may be mentioned 2-hexyldecanol such as that sold by the company Condea under the name "Isofol 16", octyl dodecanol such as that sold by the company Henkel under the name "Eutanol G", and isostearyl alcohol such as that sold by the company Sherex under the name "Adol 66".

Among the diesters of C₆ -C₁₄ dicarboxylic acids and of isopropyl alcohol which may be used in the present invention, there may be mentioned diisopropyl adipate such as that sold by the company ISP under the name "Ceraphyl 230".

Among the triglycerides of C₆ -C₁₈ fatty acids, according to the present invention, the use of mixed triglycerides of capric/caprylic acids, such as those sold by the company Hulls France under the name "Miglyol 812", is preferred.

In a specific embodiment of the present invention, it is possible to use the mixture of two or several of these solvents for the lipophilic active agent sensitive to oxygen and/or to water.

The composition according to the present invention may further contain all the ingredients conventionally used in the cosmetic or dermatological field, in usual concentrations. These ingredients are, in particular, one or more fatty substances, preservatives, vitamins and other active agents, gelling agents, perfumes, surfactants, water, antioxidants, fillers, screening agents, moisturizing agents and mixtures thereof.

The present composition may also contain ionic and/or nonionic type lipid vesicles. The quantities of these various adjuvants which may be used are those conventionally used in the cosmetic and/or dermatological fields, and for example about 0.01% to 20% of the total weight of the composition.

Other conventional constituents of cosmetic, pharmaceutical or veterinary compositions may be introduced into the emulsions according to the present invention. The nature of these ingredients and their proportion should, preferably, be compatible with the desired stability of the active agent sensitive to oxygen and/or to water in the compositions according to the invention.

The present composition may be provided in any of the galenic forms normally used for a topical application, especially in the form of an oily gel or an oil-in-water or water-in-oil emulsion. The composition may be fluid to a greater or lesser degree and may be in the form of a cream, an ointment, a paste or a foam, for example.

When the composition of the present invention is an emulsion, the proportion of the fatty phase may range from about 5 to 80% by weight, and preferably from about 5 to 50% by weight relative to the total weight of the composition. The oils, emulsifiers and coemulsifiers used in the composition in emulsion may be those conventionally used in the domain considered. The emulsifier and coemulsifier are present, in the composition, in a proportion ranging from about 0.3 to 30% by weight, and preferably from about 0.5 to 20% by weight relative to the total weight of the composition. The emulsion may, in addition, contain lipid vesicles.

As emulsifiers which can be used in the present invention, there may be mentioned, for example, the silicone emulsifiers, especially the polyoxyethylenated C₁₀ -C₂₂ alkyl dimethicone copolyols such as cetyl dimethicone copolyol or "Abil EM-90", from the company Goldschmidt, or polyoxyethylenated and polyoxypropylenated lauryl dimethicone copolyol such as Q2-5200 from Dow Corning, and a mixture of the two.

Polyoxyethylenated dimethicone copolyols such as SP 1228 from General Electric and also Q2-3225 C from Dow Corning may also be used.

The oily phase of the emulsion may also contain an additional oil which is inert towards the active agent sensitive to oxygen and/or to water, preferably chosen from mineral or silicone oils.

Among the mineral oils which can be used according to the present invention, there may be mentioned, inter alia, isohexadecane, paraffin, isoparaffin and petroleum jelly.

Among the silicone oils which can be used in the present invention, there may be mentioned, inter alia, dimethicones, dimethiconols, cyclomethicones such as cyclopentadimethylsiloxane (or cyclomethicone D5) or cyclohexadimethylsiloxane (or cyclodimethicone D6) or alkyl dimethicones and a mixture of some of these compounds such as "Q2-1401 gum" from Dow Corning.

The present composition may be used especially for the treatment of the skin, in particular for treating acne and the damage induced by age and/or the sun, and more especially normal and/or small wrinkles and/or aging of the skin. Consequently, another object of the present invention is the cosmetic and/or dermatological use of the composition as defined above for treating acne and/or normal and/or small wrinkles and/or aging of the skin. By `aging of the skin` is meant the general deterioration of skin appearance due to the passage of time, such as wrinkling, discoloration or blotching.

Claim 1 of 26 Claims

What is claimed as new and is desired to be secured by Letters: Patent of the United States is:

1. A stable gelled composition, comprising at least one lipophilic active agent sensitive to at least oxygen, and a solvent, which composition comprises, as gelling agent, at least ethylated guar gum.

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