Patent Application
20200405604
The present invention relates to a cosmetic composition containing 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone and a particular organic solvent.
4-(3-Ethoxy-4-hydroxyphenyl)-2-butanone is a useful substance as a preserving agent for cosmetic compositions, for protecting the compositions against microbial contamination.
However, this compound, which is in solid form at room temperature, is very sparingly soluble in water or glycerol.
Now, it is necessary for this compound to be formulated in a solubilized form in order to fully exploit its activity, and it is also preferable for its solubilization to be maintained over time in order to avoid any recrystallization during storage of compositions comprising such a compound.
The object of the present invention is, precisely, to propose a novel galenical formulation of 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone that overcomes the abovementioned drawbacks, and thus enables this compound to be incorporated in a long-lasting solubilized form.
Specifically, the inventors have discovered, unexpectedly, that the combination of 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone with at least one particular organic solvent enables this compound to be solubilized while avoiding its recrystallization, especially after storage for two months at room temperature (25° C.).
More precisely, a subject of the invention is a composition, especially a cosmetic composition, comprising, in a physiologically acceptable aqueous medium, 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone and an organic solvent with solubility parameters in the Hansen solubility space such that 14.5<δa<30 and 15<δd<20 as defined below.
A further subject of the invention is a process for the non-therapeutic cosmetic treatment of keratin materials, comprising the application to the keratin materials of a composition as described previously. The process may be a cosmetic process for caring for, making up or cleansing keratin materials.
As specified hereinbelow, 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone is advantageously present in the compositions in accordance with the invention in a solubilized form.
4-(3-Ethoxy-4-hydroxyphenyl)-2-butanone is a compound of formula:
The compound 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone may be present in the composition according to the invention in a content ranging from 0.01% to 10% by weight, better still from 0.1% to 7% by weight, from 0.5% to 7% by weight, from 0.75% to 5% by weight and preferably ranging from 1% to 5% by weight, relative to the total weight of the composition.
The composition according to the invention comprises an effective amount of at least one solvent with solubility parameters in the Hansen solubility space such that:
14.5<δa<30 and 15<δd<22
The global solubility parameter δ according to the Hansen solubility space is defined in the article “Solubility parameter values” by Eric A. Grulke in the book “Polymer Handbook”, 3rd Edition, Chapter VII, pp. 519-559, by the relationship:
δ=(δ2=δd2+δp2+δh2)1/2
in which:
The parameter δa is defined by the following relationship: δa2=δp2+δh2=δ2−δd2
The parameters δd, δp, δh and δa are expressed in (J/cm3)1/2.
Preferably, the organic solvent has solubility parameters such that
14.5<δa<28 and 15<δd<20
The organic solvent used according to the invention may be chosen from ethanol (δa=20.20; δd=15.10), 1,2-propylene glycol (δa=25.00; δd=16.00), 1,3-propanediol (δa=26.32; δd=18.00), PEG-8 (polyethylene glycol containing 8 ethylene glycol units) (δa=14.80; δd=17.90), propylene carbonate (δa=18.46; δd=20.00); dipropylene glycol (δa=19.48; δd=16.20), 1,2-hexylene glycol (δa=19.20; δd=16.40), PEG-4 polyethylene glycol containing 4 ethylene glycol units) (δa=18.60; δd=18.00).
Preferably, the organic solvent is chosen from ethanol, 1,2-propylene glycol, 1,3-propanediol, PEG-8 and propylene carbonate.
The solvent may be present in the composition according to the invention in a content ranging from 0.05% to 30% by weight, better still from 0.05% to 10% by weight, preferably ranging from 0.1% to 5% by weight and preferentially ranging from 0.1% to 2.5% by weight, relative to the total weight of the composition.
According to one embodiment, the organic solvent in accordance with the invention and the 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone (referred to as the compound) may be present in a solvent/compound mass ratio of less than or equal to 10, especially less than or equal to 5, better still less than or equal to 4, especially ranging from 0.5 to 4 and preferably ranging from 0.5 to 1.5.
The compositions used according to the invention contain a physiologically acceptable medium, i.e. a medium that is compatible with human keratin materials such as the skin, the scalp, the hair and the nails.
The compositions according to the invention may be in the form of aqueous solutions, aqueous-alcoholic solutions, oil-in-water (O/W) emulsions, water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W or O/W/O), or aqueous gels. These compositions are prepared according to the usual methods.
The composition may comprise at least one oil. As oils that may be used, examples that may be mentioned include:
In the list of oils mentioned above, the term “hydrocarbon-based oil” means any oil mainly comprising carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups.
The composition according to the invention may comprise substances that are solid at room temperature (25° C.), for instance fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba wax or candelilla wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, and synthetic waxes such as polyethylene waxes and Fischer-Tropsch waxes.
These fatty substances may be chosen in a varied manner by a person skilled in the art so as to prepare a composition having the desired properties, for example in terms of consistency or texture.
According to one particular embodiment of the invention, the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion.
The proportion of the oily phase of the emulsion may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.
The emulsions generally contain at least one emulsifier chosen especially from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are appropriately chosen according to the emulsion to be obtained (W/O or O/W). The emulsifier and the co-emulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition.
For W/O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols, such as the mixture of cyclomethicone and dimethicone copolyol sold under the trade name DC 5225 C by the company Dow Corning, and alkyl dimethicone copolyols such as the lauryl dimethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning, and the cetyl dimethicone copolyol sold under the name Abil EM 90® by the company Goldschmidt. A crosslinked elastomeric solid organopolysiloxane comprising at least one oxyalkylene group, such as those obtained according to the procedure of Examples 3, 4 and 8 of U.S. Pat. No. 5,412,004 and of the examples of U.S. Pat. No. 5,811,487, especially the product of Example 3 (synthesis example) of U.S. Pat. No. 5,412,004, such as the product sold under the reference KSG 21 by the company Shin-Etsu, may also be used as surfactants for W/O emulsions.
For O/W emulsions, examples of emulsifiers that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alkyl ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-40 stearate (polyethylene glycol stearate containing 40 ethylene glycol units).
The composition may be an aqueous gel, and may especially comprise common aqueous gelling agents.
In a known manner, the composition according to the invention may also contain adjuvants that are common in cosmetics or dermatology, such as gelling agents, film-forming polymers, preserving agents, fragrances, fillers, UV-screening agents, bactericides, odour absorbers, dyestuffs, plant extracts, cosmetic and dermatological active agents, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.01% to 20% of the total weight of the composition.
The invention is illustrated in greater detail in the example that follows. The amounts of the ingredients are expressed as weight percentages.
The test solvent was poured into a beaker, an amount of the compound 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone was added with magnetic stirring and the mixture was left to stand for between 1 hour and 24 hours. The mixture was then heated to 50° C. and then cooled to room temperature (25° C.) over 24 hours. The system was then observed to see if the amount of compound introduced recrystallized or remained dissolved.
The amount of compound that can be dissolved in the test solvent was determined in this manner. The maximum value corresponds to the amount at and above which the ester compound stops dissolving in the evaluated solvent.
The following results were obtained in several evaluated solvents:
It was thus found that 4-(3-ethoxy-4-hydroxyphenyl)-2-butanone is very satisfactorily dissolved with ethanol, 1,2-propylene glycol, 1,3-propanediol, PEG-8 and propylene carbonate, and is very sparingly dissolved with glycerol.
A facial care cream (oil-in-water emulsion) having the following composition was prepared:
The composition is stable and homogeneous after storage for 2 months at 45° C.
A sun cream having the following composition was prepared:
Phase A was heated to between 80° C. and 85° C.
Phase B was heated until all the fatty substances had fully melted (about 85° C.).
Phase A was rapidly added to phase B with very vigorous stirring. The emulsion was then subjected to high-pressure homogenization. Phases C to F were finally added.
The emulsion obtained is in the form of oleosomes. After storage for 2 months at 45° C., the formulation is stable and homogeneous.
A shower gel having the following composition was prepared:
After storage for 2 months at 45° C., the formulation is stable and homogeneous.
| Number | Date | Country | Kind |
|---|---|---|---|
| 1152787 | Apr 2011 | FR | national |
This application is a Divisional of application Ser. No. 14/007,520 filed on Mar. 29, 2012, which is the National Phase filing under 35 U.S.C. § 371 of PCT/EP2012/055657 filed on Mar. 29, 2012; which application in turn claims priority to Application No. 1152787 filed in France on Apr. 1, 2011; and claims the benefit of U.S. Provisional Application No. 61/499,708 filed on Jun. 22, 2011; the entire contents of all are hereby incorporated by reference.
| Number | Date | Country | |
|---|---|---|---|
| 61499708 | Jun 2011 | US |
| Number | Date | Country | |
|---|---|---|---|
| Parent | 14007520 | Nov 2013 | US |
| Child | 15931988 | US |
