专利汇可以提供COSMETIC OR DERMATOLOGICAL EMULSION COMPRISING A MEROCYANINE AND AN EMULSIFYING SYSTEM CONTAINING AN AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE 2-ACRYLAMIDOMETHYLPROPANESULFONIC ACID UNIT专利检索,专利查询,专利分析的服务。并且,下面是COSMETIC OR DERMATOLOGICAL EMULSION COMPRISING A MEROCYANINE AND AN EMULSIFYING SYSTEM CONTAINING AN AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE 2-ACRYLAMIDOMETHYLPROPANESULFONIC ACID UNIT专利的具体信息内容。
The present invention relates to a cosmetic or dermatological composition in emulsion form, comprising, in a physiologically acceptable support:
Another subject of the present invention consists of a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of the said keratin material, of at least one composition according to the invention as defined above.
The invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
The invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
It is known that radiation with wavelengths of between 280 nm and 400 nm permits tanning of the human epidermis and that radiation with wavelengths of between 280 and 320 nm, known as UVB rays, harms the development of a natural tan. Exposure is also liable to bring about a detrimental change in the biomechanical properties of the epidermis, which is reflected by the appearance of wrinkles, leading to premature ageing of the skin.
It is also known that UVA rays with wavelengths of between 320 and 400 nm penetrate more deeply into the skin than UVB rays. UVA rays cause immediate and persistent browning of the skin. Daily exposure to UVA rays, even of short duration, under normal conditions can result in damage to the collagen fibres and the elastin, which is reflected by a modification in the microrelief of the skin, the appearance of wrinkles and uneven pigmentation (liver spots, lack of uniformity of the complexion).
Protection against UVA and UVB rays is thus necessary. An efficient photoprotective product should protect against both UVA and UVB rays.
Many photoprotective compositions have been proposed to date to overcome the effects induced by UVA and/or UVB rays. They generally contain organic and/or mineral UV-screening agents, which function according to their own chemical nature and according to their own properties by absorption, reflection or scattering of the UV rays. They generally comprise mixtures of liposoluble organic screening agents and/or water-soluble UV-screening agents in combination with metal oxide pigments, such as titanium dioxide or zinc oxide.
Many cosmetic compositions for limiting the darkening of the skin and improving the colour and uniformity of the complexion have been proposed to date. It is well known in the field of antisun products that such compositions may be obtained by using UV-screening agents, and in particular UVB-screening agents. Certain compositions may also contain UVA-screening agents. This screening system should cover UVB protection for the purpose of limiting and controlling the neosynthesis of melanin, which promotes the overall pigmentation, but should also cover UVA protection so as to limit and control the oxidation of the already-existing melanin leading to darkening of the skin colour.
However, no composition contains a particular combination of UV-screening agents that would be especially suited to photoprotecting the skin and particularly to improving the quality of the skin as regards both the colour and its mechanical elasticity properties.
Advantageously, this improvement is particularly visible on already-pigmented skin so as not to increase the melanin pigmentary load or the structure of the melanin already present in the skin.
In point of fact, the majority of the organic UV-screening agents consist of aromatic compounds which absorb in the wavelength range between 280 and 370 nm. In addition to their power for screening out sunlight, the desired photoprotective compounds should also have good cosmetic properties, good solubility in the usual solvents and in particular in fatty substances such as oils, and also good chemical stability and good photostability alone or in combination with other UV-screening agents. They should also be colourless or at least have a colour that is cosmetically acceptable to the consumer.
One of the main drawbacks known to date of these compositions is that these screening systems are insufficiently effective against UV rays and in particular against long UVA rays with wavelengths beyond 370 nm, for the purpose of controlling photo-induced pigmentation and its evolution by means of a system for screening out UV over the entire UV spectrum.
Among all the compounds that have been recommended for this purpose an advantageous family of UV-screening agents has been proposed, which consists of carbon-bearing merocyanine derivatives, which is described in patent
Antisun compositions are quite often in the form of an emulsion of oil-in-water type (i.e. a cosmetically acceptable support consisting of a continuous aqueous dispersing phase and of a discontinuous oily dispersed phase) or of the water-in-oil type (i.e. a cosmetically acceptable support consisting of a continuous oily dispersing phase and of a discontinuous aqueous dispersed phase) which contains, in varying concentrations, one or more conventional lipophilic and/or hydrophilic organic screening agents which are capable of selectively absorbing harmful UV rays, these screening agents (and the amounts thereof) being selected as a function of the desired sun protection factor.
There is thus still a need to select other families of emulsifiers which guarantee a good chemical stability of the merocyanines without the drawbacks as previously defined.
The Applicant has discovered, surprisingly, that the use of one emulsifying system containing at least one amphiphilic polymer comprising at least one 2-acrylamidomethylpropanesulfonic acid unit and one merocyanine compound of formula (1) make it possible to achieve this objective.
Furthermore, the merocyanine compounds of formula (1) herein below, present surprinsingly the advantage to be significantly less colored than the merocyanine compounds as disclosed in the application
Those discoveries form the basis of the present invention.
Thus, in accordance with one of the objects of the present invention, a cosmetic or dermatological composition in emulsion form is now proposed, comprising, in a physiologically acceptable support:
Another subject of the present invention consists of a non-therapeutic cosmetic process for caring for and/or making up a keratin material, comprising the application, to the surface of the said keratin material, of at least one composition according to the invention as defined above.
The invention also relates to a non-therapeutic cosmetic process for limiting the darkening of the skin and/or improving the colour and/or uniformity of the complexion, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
The invention also relates to a non-therapeutic cosmetic process for preventing and/or treating the signs of ageing of a keratin material, comprising the application, to the surface of the keratin material, of at least one composition as defined previously.
Other characteristics, aspects and advantages of the invention will emerge on reading the detailed description that follows.
The expression "human keratin materials" means the skin (body, face, area around the eyes), hair, eyelashes, eyebrows, body hair, nails, lips or mucous membranes.
The term "physiologically acceptable" means compatible with the skin and/or its integuments, having a pleasant colour, odour and feel and not causing any unacceptable discomfort (stinging, tautness or redness) liable to discourage the consumer from using this composition.
The term "between X and Y" means the range of values also including the limits X and Y.
According to the invention, the term "preventing" or "prevention" means reducing the risk of occurrence or slowing down the occurrence of a given phenomenon, namely, according to the present invention, the signs of ageing of a keratin material.
The term "emulsion" means any macroscopically homogeneous, kinetically stable composition comprising at least two mutually immiscible phases; one being a dispersing continuous phase and the other being dispersed in the said continuous phase in the form of droplets. The two phases are kinetically stabilized by at least one emulsifying system generally comprising at least one emulsifying surfactant.
Emulsions are distinguished as being of the oil-in-water type, known as "direct" emulsions, consisting of an aqueous dispersing continuous phase and of an oily dispersed discontinuous phase, and emulsions of the water-in-oil type, known as inverse emulsions, consisting of an oily dispersing continuous phase and of an aqueous dispersed discontinuous phase. There are also multiple emulsions, for instance water-in-oil-in-water or oil-in-water-in-oil emulsions.
The term "emulsifying system" refers to any compound or mixture of compounds that is capable of increasing the kinetic stability of an emulsion. These compounds are generally amphiphilic and are surfactants characterized by their more or less hydrophilic or more or less lipophilic nature which will determine their ability to stabilize direct emulsions or inverse emulsions. They are especially classified by their HLB according to the calculation method of
According to the present invention, the merocyanine compounds in accordance with the invention correspond to formula (1) below, and also the E/E- or E/Z-geometrical isomer forms thereof:
in which:
The merocyanine compounds of the invention may be in their E/E- or E/Z-geometrical isomer forms.
The preferential compounds of formula (1) are those in which:
Among the compounds of formula (1), use will be made more particularly of those chosen from the following compounds, and also the E/E- or E/Z- geometrical isomer forms thereof:
According to a more particularly preferred mode of the invention, use will be made of the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (2) in its E/Z geometrical configuration having the following structure:
and/or in its E/E geometrical configuration having the following structure:
The merocyanines of formula (1) according to the invention are preferably present in the compositions according to the invention in a concentration ranging from 0.1 % to 10% by weight and preferentially from 0.2% to 5% by weight relative to the total weight of the composition.
The compounds of formula (1) may be prepared according to the protocols described in Pat. Appl.
For the purposes of the invention, the term "amphiphilic polymer" is intended to denote a polymer having amphiphilic properties, i.e. having at least one hydrophilic part and at least one hydrophobic part. Hydrophilic groups and hydrophobic groups are well known to those skilled in the art.
For the purposes of the present invention, the term "polymer" is intended to denote a compound comprising at least two repeating units and in particular at least five repeating units.
The amphiphilic polymers under consideration according to the invention are amphiphilic polymers comprising at least one 2-acrylamidomethylpropanesulfonic acid (AMPS®) unit.
The amphiphilic polymers comprising at least one 2-acrylamidomethylpropanesulfonic acid (AMPS®) unit that may be used in the present invention, which are also known more simply as "amphiphilic AMPS® polymers" hereinbelow, comprise both a hydrophilic part and a hydrophobic part comprising at least one fatty chain.
The fatty chain present in the said amphiphilic AMPS® polymers according to the invention may preferably comprise from 7 to 30 carbon atoms and more preferentially from 7 to 22 carbon atoms.
The amphiphilic AMPS® polymers according to the invention are especially chosen from amphiphilic polymers of at least one 2-acrylamidomethylpropanesulfonic acid (AMPS®) monomer and of at least one ethylenically unsaturated hydrophobic comonomer comprising at least one hydrophobic part containing from 7 to 30 carbon atoms and in particular from 7 to 22 carbon atoms or even from 12 to 22 carbon atoms.
The amphiphilic AMPS® polymers according to the invention generally have a weight-average molecular weight ranging from 50 000 to 10 000 000 g/mol, in particular from 100 000 to 8 000 000 g/mol and even more particularly from 100 000 to 7 000 000 g/mol.
They may be crosslinked or non-crosslinked.
When the amphiphilic AMPS® polymers according to the invention are crosslinked, the crosslinking agents may be chosen from the polyolefinically unsaturated compounds commonly used for the crosslinking of polymers obtained by free-radical polymerization.
Examples of crosslinking agents that may be mentioned include divinylbenzene, diallyl ether, dipropylene glycol diallyl ether, polyglycol diallyl ethers, triethylene glycol divinyl ether, hydroquinone diallyl ether, ethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, trimethylolpropane triacrylate, methylenebis(acrylamide), methylenebis(methacrylamide), triallylamine, triallyl cyanurate, diallyl maleate, tetraallylethylenediamine, tetraallyloxyethane, trimethylolpropane diallyl ether, allyl (meth)acrylate, allylic ethers of alcohols of the sugar series, or other allylic or vinyl ethers of polyfunctional alcohols, and also allylic esters of phosphoric and/or vinylphosphonic acid derivatives, or mixtures of these compounds.
The crosslinking agents may be chosen especially from methylenebis(acrylamide), allyl methacrylate and trimethylolpropane triacrylate (TMPTA).
The degree of crosslinking may range, for example, from 0.01 mol% to 10 mol% and preferably from 0.2 mol% to 2 mol% relative to the polymer.
The amphiphilic AMPS® polymers according to the invention may be chosen especially from random amphiphilic AMPS® polymers modified by reaction with a C6-C22 n-monoalkylamine or di-n-alkylamine, such as those described in patent application
An amphiphilic polymer that is suitable for use in the invention may comprise at least one ethylenically unsaturated hydrophilic comonomer chosen, for example, from acrylic acid, methacrylic acid or substituted alkyl derivatives thereof or esters thereof obtained with monoalkylene or polyalkylene glycols, acrylamide, methacrylamide, vinylpyrrolidone, vinylformamide, maleic anhydride, itaconic acid or maleic acid, or mixtures thereof.
An amphiphilic polymer according to the invention may comprise at least one ethylenically unsaturated hydrophobic comonomer.
An amphiphilic polymer that is suitable for use in the invention may comprise at least one hydrophobic part chosen from saturated or unsaturated, linear alkyl radicals, for instance n-octyl, n-decyl, n-hexadecyl, n-dodecyl and oleyl, branched alkyl radicals, for instance isostearyl, or cyclic alkyl radicals, for instance cyclododecane or adamantane.
An amphiphilic AMPS® polymer may also contain at least one ethylenically unsaturated hydrophobic comonomer comprising, for example:
These copolymers are especially described in document
They are also described in documents
An ethylenically unsaturated hydrophobic comonomer of the invention may preferably be chosen from the acrylates or acrylamides of formula (I) below:
in which:
The hydrophobic radical Rb is chosen from saturated or unsaturated linear C7-C22 alkyl radicals (for example n-octyl, n-decyl, n-hexadecyl, n-dodecyl or oleyl), branched alkyl radicals (for example isostearic) or cyclic alkyl radicals (for example cyclododecane or adamantane); C7-C18 alkylperfluoro radicals (for example the group of formula -(CH2)2(CF2)9-CF3); the cholesteryl radical or a cholesterol ester, for instance cholesteryl hexanoate; aromatic polycyclic groups, for instance naphthalene or pyrene.
Among these radicals, linear and branched alkyl radicals are more particularly preferred.
According to a preferred embodiment of the invention, the hydrophobic radical Rb may also comprise at least one alkylene oxide unit and preferably a polyoxyalkylene chain.
The polyoxyalkylene chain may preferentially consist of ethylene oxide units and/or propylene oxide units and even more particularly consists solely of ethylene oxide units.
The number of moles of oxyalkylene units may generally range from 1 to 30 mol, more preferentially from 1 to 25 mol and even more preferentially from 3 to 20 mol.
Among these polymers, mention may be made of:
Amphiphilic AMPS® polymers that may also be mentioned include copolymers of totally neutralized AMPS® and of n-dodecyl, n-hexadecyl and/or n-octadecyl methacrylate, and also non-crosslinked and crosslinked copolymers of AMPS® and of n-dodecylmethacrylamide.
Mention will be made more particularly of crosslinked or non-crosslinked amphiphilic AMPS® copolymers consisting of:
in which X is a proton, an alkali metal cation, an alkaline-earth metal cation or an ammonium ion;
and units of formula (III) below:
in which n and p, independently of one another, denote a number of moles and range from 0 to 30, preferentially from 1 to 25 and more preferentially from 3 to 20, with the proviso that n + p is less than or equal to 30, preferably less than 25 and better still less than 20; Ra denotes a hydrogen atom or a linear or branched C1-C6 alkyl radical, preferably methyl, and Rc denotes a linear or branched alkyl containing from 7 to 22 carbon atoms and preferably from 12 to 22 carbon atoms.
In formula (II), the cation X more particularly denotes sodium or ammonium.
Among the monomers of formula (III), mention may be made of:
The products that will be chosen more particularly are:
These polymers are described and synthesized in patent application
These particular amphiphilic AMPS® polymers may be obtained according to the standard processes of free-radical polymerization in the presence of one or more initiators, for instance azobisisobutyronitrile (AIBN), azobisdimethylvaleronitrile, 2,2-azobis(2-amidinopropane) hydrochloride (ABAH), organic peroxides such as dilauryl peroxide, benzoyl peroxide, tert-butyl hydroperoxide, mineral peroxide compounds such as potassium or ammonium persulfate, or H2O2 optionally in the presence of reducing agents.
These amphiphilic AMPS® polymers may be obtained especially by free-radical polymerization in tert-butanol medium, in which they precipitate. By using precipitation polymerization in tert-butanol, it is possible to obtain a size distribution of the polymer particles that is particularly favourable for its uses.
The reaction may be performed at a temperature of between 0 and 150°C and preferably between 10 and 100°C, either at atmospheric pressure or under reduced pressure.
It may also be performed under inert atmosphere, and preferably under nitrogen.
The amphiphilic AMPS® polymers according to the invention may preferably be partially or totally neutralized with a mineral base such as sodium hydroxide, potassium hydroxide, aqueous ammonia or an organic base such as monoethanolamine, diethanolamine, triethanolamine, an aminomethylpropanediol, N-methylglucamine, basic amino acids, for instance arginine and lysine, and mixtures of these compounds. They may especially be totally or almost totally neutralized, i.e. at least 80% neutralized.
The molar percentage concentration of the units of formula (II) and of the units of formula (III) in the amphiphilic AMPS® polymers according to the invention may vary as a function of the desired cosmetic application, for example the nature of the emulsion (oil-in-water or water-in-oil emulsion) and the desired rheological properties of the formulation. It may range, for example, between 0.1 mol% and 99.9 mol%.
Preferably, for the most hydrophobic polymers, the molar proportion of units of formula (I) or (III) ranges from 50.1% to 99.9%, more particularly from 70% to 95% and even more particularly from 80% to 90%.
Preferably, for the sparingly hydrophobic polymers, the molar proportion of units of formula (I) or (III) ranges from 0.1% to 50%, more particularly from 5% to 25% and even more particularly from 10% to 20%.
The distribution of the monomers in the AMPS® polymers according to the invention may be, for example, alternate, block (including multiblock) or random.
As a guide, and without this being limiting, mention may be made especially of:
According to a preferred embodiment, the polymer used according to the invention is a copolymer of AMPS and of a C16-C18 alkyl methacrylate comprising from 6 to 25 mol of ethylene oxide, this copolymer being obtained from AMPS and methacrylic acid or a methacrylic acid salt and from a polyoxyethylenated C16-C18 alcohol comprising 6 to 25 mol of ethylene oxide.
According to an even more preferred embodiment of the invention, the polymer used according to the invention is a copolymer of AMPS and of a C16-C18 alkyl methacrylate comprising from 6 to 10 mol of ethylene oxide, for which the mole proportion of C16-C18 alkyl methacrylate units (units (II)) ranges from 2% to 15% and better still from 5% to 10%. It is more particularly a copolymer of AMPS and of methacrylic acid or a methacrylic acid salt and of oxyethylenated stearyl alcohol (Genapol T-080) comprising a mole proportion of alkyl methacrylate units of 7.35%.
A preferred polymer according to the invention that may be mentioned in particular is the copolymer of AMPS and of the ammonium salt of methacrylic acid and of oxyethylenated stearyl alcohol comprising 8 mol of ethylene oxide (Genapol T-080 methacrylate) and comprising a mole proportion of alkyl methacrylate units of 7.35%, sold under the name Aristoflex SNC by the company Clariant (INCI name: Ammonium acryloyldimethyltaurate/steareth-8 methacrylate copolymer).
The amphiphilic polymers in accordance with the invention are present in the compositions in active material concentrations preferably ranging from 0.01% to 2% by weight, more preferentially from 0.01% to 1% by weight and better still from 0.1 % to 0.5% by weight, relative to the total weight of the composition.
The compositions according to the invention may be in the form of an oil-in-water emulsion or a water-in-oil emulsion as a function of the nature of the relative proportion of the hydrophobic and hydrophilic parts and/or of the chemical nature of the amphiphilic polymer thereof comprising at least one 2-acrylamidomethylpropanesulfonic acid unit.
They may contain other emulsifying surfactants that are suited to the type of emulsion.
For the O/W emulsions, examples of emulsifiers that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) esters of fatty acids and of glycerol; oxyalkylenated esters of fatty acids and of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) esters of fatty acids, such as the PEG-100 stearate/glyceryl stearate mixture sold, for example, by ICI under the name Arlacel 165; oxyalkylenated (oxyethylenated and/or oxypropylenated) ethers of fatty alcohols; esters of sugars, such as sucrose stearate; or ethers of fatty alcohol and of sugar, in particular alkyl polyglucosides (APGs), such as decyl glucoside and lauryl glucoside, sold, for example, by the company Henkel under the respective names Plantaren 2000 and Plantaren 1200, cetostearyl glucoside, optionally as a mixture with cetostearyl alcohol, sold, for example, under the name Montanov 68 by the company SEPPIC, under the name Tegocare CG90 by the company Goldschmidt and under the name Emulgade KE3302 by the company Henkel, and also arachidyl glucoside, for example in the form of a mixture of arachidyl alcohol, behenyl alcohol and arachidyl glucoside, sold under the name Montanov 202 by the company SEPPIC. According to a particular embodiment of the invention, the mixture of the alkyl polyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, for example as described in document
According to a particular form of the invention, use will also be made of C11-C18 fatty acids such as undecanoic acid or lauric acid, such as the products sold under the trade name Acide Laurique 98® by the company Stéarineries Dubois, or Edenor C12-99 MY® by the company Emery Oleochemicals, palmitic acid, such as the products sold under the trade name Palmera A9516® or Palmera A9816® by the company KLK Oleo, or Acide Palmitique 95% - Pastilles by the company Stéarineries Dubois, or the stearic acid sold under the trade name Palmera B1802CG by the company KLK Oleo, Stéarine TP 1200 Pastilles® (DUB 50P®) by the company Stéarineries Dubois, or Kortacid PH 05.02® by the company Pacific Oleochemicals, or mixtures thereof, for instance the mixture of stearic and palmitic acid sold under the trade name Dub Microlub 50® by the company Stéarineries Dubois, and more particularly stearic acid. The fatty acids may be present in the compositions of the invention preferably between 0.1% and 5% and more particularly between 0.5% and 3%.
As emulsifying surfactants that may be used for the preparation of the W/O emulsions, examples that may be mentioned include sorbitan, glycerol or sugar alkyl esters or ethers; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name DC 5225 C by the company Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning; cetyldimethicone copolyol, such as the product sold under the name Abil EM 90R by the company Goldschmidt, and the mixture of cetyldimethicone copolyol, of polyglyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE 09 by the company Goldschmidt. One or more coemulsifiers may also be added thereto, which may be chosen advantageously from the group consisting of polyol alkyl esters.
Polyol alkyl esters that may especially be mentioned include polyethylene glycol esters, for instance PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by the company ICI.
Esters of glycerol and/or of sorbitan that may be mentioned include, for example, polyglyceryl isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt, sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI, sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.
According to a particular mode of the invention, the composition will not contain any emulsifying agents other than the amphiphilic polymer comprising at least one 2-acrylamidomethylpropanesulfonic acid unit.
The term "not containing" means "containing less than 0.5%" or even "free of" emulsifying agents other than the polymer of the invention.
The compositions in accordance with the invention comprise at least one oily phase.
For the purposes of the invention, the term "oily phase" means a phase comprising at least one oil and all of the liposoluble and lipophilic ingredients and the fatty substances used for the formulation of the compositions of the invention.
The term "oil" means any fatty substance that is in liquid form at room temperature (20 - 25°C) and at atmospheric pressure (760 mmHg).
An oil that is suitable for use in the invention may be volatile or non-volatile.
An oil that is suitable for use in the invention may be chosen from hydrocarbon-based oils, silicone oils and fluoro oils, and mixtures thereof.
A hydrocarbon-based oil that is suitable for use in the invention may be an animal hydrocarbon-based oil, a plant hydrocarbon-based oil, a mineral hydrocarbon-based oil or a synthetic hydrocarbon-based oil.
An oil that is suitable for use in the invention may be advantageously chosen from mineral hydrocarbon-based oils, plant hydrocarbon-based oils, synthetic hydrocarbon-based oils and silicone oils, and mixtures thereof.
For the purposes of the present invention, the term "silicone oil" means an oil comprising at least one silicon atom, and especially at least one Si-O group.
The term "hydrocarbon-based oil" means an oil comprising mainly hydrogen and carbon atoms.
The term "fluoro oil" means an oil comprising at least one fluorine atom.
A hydrocarbon-based oil that is suitable for use in the invention may also optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl, amine, amide, ester, ether or acid groups, and in particular in the form of hydroxyl, ester, ether or acid groups.
The oily phase generally comprises, in addition to the lipophilic UV-screening agent or agents, at least one volatile or non-volatile hydrocarbon-based oil and/or one volatile and/or non-volatile silicone oil.
For the purposes of the invention, the term "volatile oil" means an oil that is capable of evaporating on contact with the skin or the keratin fibre in less than one hour, at room temperature and atmospheric pressure. The volatile oil(s) of the invention are volatile cosmetic oils which are liquid at room temperature and which have a non-zero vapour pressure, at room temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10-3 to 300 mmHg), in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg).
The term "non-volatile oil" means an oil that remains on the skin or the keratin fibre at room temperature and atmospheric pressure for at least several hours, and that especially has a vapour pressure of less than 10-3 mmHg (0.13 Pa).
As non-volatile hydrocarbon-based oils that may be used according to the invention, mention may be made especially of:
and mixtures thereof.
Among the non-volatile hydrocarbon-based oils that may be used according to the invention, preference will be given more particularly to glyceride triesters and in particular to caprylic/capric acid triglycerides, synthetic esters and in particular isononyl isononanoate, oleyl erucate, C12-C15 alkyl benzoate, 2-ethylphenyl benzoate and fatty alcohols, in particular octyldodecanol.
As volatile hydrocarbon-based oils that may be used according to the invention, mention may be made especially of hydrocarbon-based oils having from 8 to 16 carbon atoms and in particular of branched C8-C16 alkanes, such as C8-C16 isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane or isohexadecane, the oils sold under the Isopar or Permethyl trade names, branched C8-C16 esters, isohexyl neopentanoate, and mixtures thereof.
Mention may also be made of the alkanes described in the Cognis patent applications
Other volatile hydrocarbon-based oils, for instance petroleum distillates, especially those sold under the name Shell Solt® by the company Shell, may also be used. According to one embodiment, the volatile solvent is chosen from volatile hydrocarbon-based oils containing from 8 to 16 carbon atoms, and mixtures thereof.
The non-volatile silicone oils may be chosen in particular from non-volatile polydimethylsiloxanes (PDMSs), polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, which groups each contain from 2 to 24 carbon atoms, or phenyl silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl(trimethylsiloxy)diphenylsiloxanes, diphenyl dimethicones, diphenyl(methyldiphenyl)trisiloxanes or (2-phenylethyl)trimethylsiloxysilicates.
Examples of volatile silicone oils that may be mentioned include volatile linear or cyclic silicones, especially those with a viscosity ≤ 8 centistokes (8 × 10-6 m2/s) and especially containing from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups containing from 1 to 10 carbon atoms. As volatile silicone oils that may be used in the invention, mention may be made especially of octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane and dodecamethylpentasiloxane, and mixtures thereof.
Mention may also be made of the volatile linear alkyltrisiloxane oils of general formula (I):
where R represents an alkyl group comprising from 2 to 4 carbon atoms, one or more hydrogen atoms of which may be replaced with a fluorine or chlorine atom.
Among the oils of general formula (I), mention may be made of:
Use may also be made of volatile fluoro oils, such as nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane, and mixtures thereof.
An oily phase according to the invention may also comprise other fatty substances, mixed with or dissolved in the oil.
Another fatty substance that may be present in the oily phase may be, for example:
Preferably, the overall oily phase, including all the lipophilic substances of the composition capable of being dissolved in this same phase, represents from 5% to 95% by weight and preferably from 10% to 80% by weight, with respect to the total weight of the composition.
The compositions according to the invention comprise at least one aqueous phase.
The aqueous phase comprises water and optionally other water-soluble or water-miscible organic solvents.
An aqueous phase that is suitable for use in the invention may comprise, for example, a water chosen from a natural spring water, such as water from La Roche-Posay, water from Vittel or waters from Vichy, or a floral water.
The water-soluble or water-miscible solvents that are suitable for use in the invention comprise short-chain monoalcohols, for example C1-C4 monoalcohols, such as ethanol or isopropanol; diols or polyols, such as ethylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, 2-ethoxyethanol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, glycerol and sorbitol, and mixtures thereof.
According to a preferred embodiment, use may more particularly be made of ethanol, propylene glycol, glycerol, and mixtures thereof.
According to a particular form of the invention, the overall aqueous phase, including all the hydrophilic substances of the composition capable of being dissolved in this same phase, represents from 5% to 95% by weight and preferably from 10% to 80% by weight, relative to the total weight of the composition.
The compositions according to the invention may also contain one or more additional UV-screening agents chosen from hydrophilic, lipophilic or insoluble organic UV-screening agents and/or one or more mineral pigments. It will preferentially consist of at least one hydrophilic, lipophilic or insoluble organic UV-screening agent.
The additional organic UV-screening agents are chosen in particular from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidenecamphor compounds; benzophenone compounds; β,β-diphenylacrylate compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds, in particular those cited in patent
As examples of organic photoprotective agents, mention may be made of those denoted hereinbelow under their INCI name:
Ethylhexyl methoxycinnamate sold especially under the trade name Parsol MCX® by DSM Nutritional Products,
Butylmethoxydibenzoylmethane sold in particular under the trade name Parsol 1789® by DSM Nutritional Products, Inc.;
Isopropyldibenzoylmethane.
Phenylbenzimidazolesulfonic acid, sold in particular under the trade name Eusolex 232® by Merck.
Disodium phenyl dibenzimidazole tetrasulfonate, sold under the trade name Neo Heliopan AP® by Haarmann and Reimer.
Drometrizole trisiloxane, sold under the name Silatrizole® by Rhodia Chimie.
Methylenebis(hydroxyphenylbenzotriazole) compounds:
Methylenebis(benzotriazolyl)tetramethylbutylphenol especially in solid form, for instance the product sold under the trade name Mixxim BB/100® by Fairmount Chemical, or in the form of an aqueous dispersion of micronized particles with a mean particle size ranging from 0.01 to 5 µm, more preferentially from 0.01 to 2 µm and more particularly from 0.020 to 2 µm, with at least one alkylpolyglycoside surfactant having the structure CnH2n+1O(C6H10O5)xH, in which n is an integer from 8 to 16 and x is the mean degree of polymerization of the (C6H10O5) unit and ranges from 1.4 to 1.6, as described in patent
Menthyl anthranilate, sold under the trade name Neo Heliopan MA® by Symrise.
Ethylhexyl dimethoxybenzylidene dioxoimidazoline propionate.
Polyorganosiloxane comprising benzalmalonate functional groups, such as Polysilicone-15, sold under the trade name Parsol SLX® by Hoffmann-LaRoche.
1,1-Dicarboxy(2,2'-dimethylpropyl)-4,4-diphenylbutadiene.
2,4-Bis[4-[5-(1,1-dimethylpropyl)benzoxazol-2-yl]phenylimino]-6-[(2-ethylhexyl)imino]-1,3,5-triazine, sold under the name of Uvasorb K2A® by Sigma 3V.
The preferred organic screening agents are chosen from:
The particularly preferred organic screening agents are chosen from:
The mineral UV-screening agents used in accordance with the present invention are metal oxide pigments. More preferentially, the mineral UV-screening agents of the invention are metal oxide particles with a mean elementary particle size of less than or equal to 0.5 µm, more preferentially between 0.005 and 0.5 µm, even more preferentially between 0.01 and 0.2 µm, better still between 0.01 and 0.1 µm and more particularly between 0.015 and 0.05 µm.
They may be selected in particular from titanium oxide, zinc oxide, iron oxide, zirconium oxide and cerium oxide, or mixtures thereof.
Such coated or uncoated metal oxide pigments are described in particular in patent application
The metal oxide pigments may be coated or uncoated.
The coated pigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal alkoxides (of titanium or aluminium), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
The coated pigments are more particularly titanium oxides that have been coated:
Mention may also be made of TiO2 pigments doped with at least one transition metal such as iron, zinc or manganese and more particularly manganese. Preferably, the said doped pigments are in the form of an oily dispersion. The oil present in the oily dispersion is preferably chosen from triglycerides including those of capric/caprylic acids. The oily dispersion of titanium oxide particles may also comprise one or more dispersants, for instance a sorbitan ester, for instance sorbitan isostearate, or a polyoxyalkylenated fatty acid ester of glycerol, for instance TRI-PPG3 myristyl ether citrate and polyglyceryl-3 polyricinoleate. Preferably, the oily dispersion of titanium oxide particles comprises at least one dispersant chosen from polyoxyalkylenated fatty acid esters of glycerol. Mention may be made more particularly of the oily dispersion of TiO2 particles doped with manganese in capric/caprylic acid triglycerides in the presence of TRI-PPG-3 myristyl ether citrate and polyglyceryl-3 polyricinoleate and sorbitan isostearate having the INCI name: titanium dioxide (and) TRI-PPG-3 myristyl ether citrate (and) polyglyceryl-3 ricinoleate (and) sorbitan isostearate, for instance the product sold under the trade name Optisol TD50® by the company Croda.
The uncoated titanium oxide pigments are sold, for example, by the company Tayca under the trade names Microtitanium Dioxide MT 500 B or Microtitanium Dioxide MT 600 B®, by the company Degussa under the name P 25, by the company Wackher under the name Transparent Titanium Oxide PW®, by the company Miyoshi Kasei under the name UFTR®, by the company Tomen under the name ITS® and by the company Tioxide under the name Tioveil AQ®.
The uncoated zinc oxide pigments are for example:
The coated zinc oxide pigments are for example:
The uncoated cerium oxide pigments may be, for example, those sold under the name Colloidal Cerium Oxide® by the company Rhone-Poulenc.
The uncoated iron oxide pigments are sold, for example, by the company Arnaud under the names Nanogard WCD 2002® (FE 45B®), Nanogard Iron FE 45 BL AQ®, Nanogard FE 45R AQ® and Nanogard WCD 2006® (FE 45R®) or by the company Mitsubishi under the name TY-220®.
The coated iron oxide pigments are sold, for example, by the company Arnaud under the names Nanogard WCD 2008 (FE 45B FN)®, Nanogard WCD 2009® (FE 45B 556®), Nanogard FE 45 BL 345® and Nanogard FE 45 BL® or by the company BASF under the name Transparent Iron Oxide®.
Mention may also be made of mixtures of metal oxides, in particular of titanium dioxide and of cerium dioxide, including the equal-weight mixture of titanium dioxide and cerium dioxide coated with silica, sold by the company Ikeda under the name Sunveil A®, and also the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone, such as the product M 261® sold by the company Sachtleben Pigments, or coated with alumina, silica and glycerol, such as the product M 211® sold by the company Sachtleben Pigments.
According to the invention, coated or uncoated titanium oxide pigments are particularly preferred.
The additional UV-screening agents according to the invention are preferably present in the compositions according to the invention in a content ranging from 0.1 % to 45% by weight and in particular from 5% to 30% by weight relative to the total weight of the composition.
The aqueous compositions in accordance with the present invention may also comprise conventional cosmetic adjuvants chosen in particular from organic solvents, ionic or nonionic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, basifying or acidifying agents or any other ingredient commonly used in the cosmetic and/or dermatological field.
Among the organic solvents that may be mentioned are lower alcohols and polyols. These polyols may be chosen from glycols and glycol ethers, for instance ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.
Thickeners that may be mentioned include carboxyvinyl polymers such as the Carbopol products (carbomers) and the Pemulen products (acrylate/C10-C30-alkyl acrylate copolymer) (PemulenTR1® or PemulenTR2®); polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305® (CTFA name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyl taurate copolymer/isohexadecane/polysorbate 80) by the company SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, such as the poly(2-acrylamido-2-methylpropanesulfonic acid) sold by the company Hoechst under the trade name Hostacerin AMPS® (CTFA name: ammonium polyacryloyldimethyl taurate) or Simulgel 800®, sold by the company SEPPIC (CTFA name: sodium polyacryloyldimethyl taurate/polysorbate 80/sorbitan oleate); copolymers of 2-acrylamido-2-methylpropanesulfonic acid and of hydroxyethyl acrylate, such as Simulgel NS® and Sepinov EMT 10®, sold by the company SEPPIC; cellulose derivatives, such as hydroxyethylcellulose; polysaccharides and in particular gums, such as xanthan gum; water-soluble or water-dispersible silicone derivatives, such as acrylic silicones, polyether silicones and cationic silicones, and mixtures thereof.
Among the acidifying agents, examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid or lactic acid, and sulfonic acids.
Among the basifying agents, examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines, such as mono-, di- and triethanolamines and derivatives thereof, sodium hydroxide or potassium hydroxide.
Preferably, the cosmetic composition comprises one or more basifying agents selected from alkanolamines, in particular triethanolamine, and sodium hydroxide.
In the case of a direct emulsion, the pH of the composition in accordance with the invention is generally between 3 and 12 approximately, preferably between 5 and 11 approximately and even more particularly from 6 to 8.5.
Among the active agents for caring for keratin materials such as the skin, the lips, the scalp, the hair, the eyelashes or the nails, examples that may be mentioned include:
A person skilled in the art will select the said active agent(s) as a function of the effect desired on the skin, the hair, the eyelashes, the eyebrows and the nails.
Needless to say, a person skilled in the art will take care to select the abovementioned optional additional compound(s) and/or the amounts thereof such that the advantageous properties intrinsically associated with the compositions in accordance with the invention are not, or are not substantially, adversely affected by the envisaged addition(s).
The compositions according to the invention may be prepared according to the techniques that are well known to those skilled in the art for manufacturing oil-in-water emulsions or water-in-oil emulsions, and in particular oil-in-water emulsions. They may be in the form of a cream, a milk or a cream gel. They may optionally be in the form of a mousse or a spray.
The compositions according to the invention are preferably in the form of an oil-in-water emulsion.
The emulsification processes that may be used are of the paddle or propeller, rotor-stator and HPH type.
In order to obtain stable emulsions with a low content of polymer (oil/polymer ratio > 25), it is possible to prepare the dispersion in concentrated phase and then to dilute the dispersion with the remainder of the aqueous phase.
It is also possible, by means of an HPH (between 50 and 800 bar), to obtain stable dispersions with drop sizes that may be as low as 100 nm.
The aqueous phase of the emulsions may comprise a nonionic vesicular dispersion prepared according to known processes (
The compositions according to the invention find their application in a large number of treatments, especially cosmetic treatments, of the skin, the lips and the hair, including the scalp, especially for protecting and/or caring for the skin, the lips and/or the hair, and/or for making up the skin and/or the lips.
Another subject of the present invention consists of the use of the compositions according to the invention as defined above for the manufacture of products for cosmetic treatment of the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and/or the scalp, especially care products, antisun products and makeup products.
The cosmetic compositions according to the invention may be used, for example, as makeup products.
Another subject of the present invention consists of a non-therapeutic cosmetic process for caring for and/or making up a keratin material, which consists in applying, to the surface of the said keratin material, at least one composition according to the invention as defined above.
The cosmetic compositions according to the invention may be used, for example, as care products and/or antisun products for the face and/or body with a liquid to semi-liquid consistency, such as milks, more or less smooth creams, cream gels or pastes. They may optionally be packaged in aerosol form and may be in the form of a mousse or a spray.
The compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or the hair in the form of fine particles by means of pressurization devices. The devices in accordance with the invention are well known to those skilled in the art and comprise non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and aerosol pumps using compressed air as propellant. These devices are described in patents
The compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants, for instance hydrofluoro compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane. They are preferably present in amounts ranging from 15% to 50% by weight relative to the total weight of the composition.
According to another aspect, the invention also relates to a cosmetic assembly comprising:
The container may be, for example, in the form of a jar or a box.
The closing member may be in the form of a lid comprising a cap mounted so as to be able to move by translation or by pivoting relative to the container housing the said makeup and/or care composition(s).
The examples that follow serve to illustrate the invention without, however, being limiting in nature. In these examples, the amounts of the composition ingredients are given as weight percentages relative to the total weight of the composition.
122.23 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 g of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally of a solvent. The following base/solvent combinations were used:
The completion of the alkylation reaction was monitored, for example, via methods such as TLC, GC or HPLC. 162.30 g of compound (14) were obtained in the form of a brown oil. After crystallization, the product was obtained in the form of yellowish crystals. Melting point: 92.7°C.
148.4 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 g of 2-ethoxyethyl cyanoacetate in the presence of an organic base and a solvent. The following base/solvent combinations were used:
101.00 g of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 g of 2-cyano-N-(3-methoxypropyl)acetamide in approximately equimolar proportions in the presence of a base and optionally of a solvent.
The following base/solvent combinations were used:
The crude product (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide was obtained in the form of a dark brown oil. After chromatography on a column of silica gel (eluent: 99/1 toluene/methanol), 81.8 g of product were obtained in the form of yellowish crystals.
Melting point: 84.7-85.3°C.
Formulations 1 to 4 were prepared.
The aqueous phase A and oily phase B were prepared by mixing the starting materials with mechanical stirring at 80°C. Once the aqueous solution A and oily solution B were macroscopically homogeneous, the emulsion was prepared by introducing phase B into phase A with stirring using a rotor-stator homogenizer at a stirring speed of 4500 rpm for 20 minutes. The emulsion was cooled to room temperature. The final emulsion was characterized by drops of between 1 µm and 20 µm in size.
The stability of the merocyanines in formulation was evaluated after storage of the formulations for 2 months. It was established by UPLC assay of the residual merocyanine content after 2 months at 45°C relative to the residual content after 2 months at 4°C. The percentage of merocyanine degradation is expressed as:
The chemical stability results for the merocyanine compounds in formulations 1 and 2 of the invention are better than those measured for formulations 3 and 4. This results demonstrates that the emulsifying systems comprising at least one amphiphilic polymer comprising at least one 2-acrylamidomethylpropanesulfonic acid unit ensure better chemical stability of the merocyanines of the invention.
The following formulations were prepared:
The compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate (2) of the invention was compared with: the compound (2Z)-2-cyano-N-(3-methoxy-propyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide according to Example A3 (outside the invention) the compound octyl-5-N,N-diethylamino-2-phenysulfonyl-2,4-pentadienoate (outside the invention).
The in vitro SPF and the in vitro UVAPPD index of each formulation were also measured.
The aqueous phase A and oily phase B were prepared by mixing the starting materials with mechanical stirring at 80°C. Once the aqueous solution A and oily solution B were macroscopically homogeneous, the emulsion was prepared by introducing phase B into phase A with stirring using a rotor-stator homogenizer at a stirring speed of 4500 rpm for 20 minutes. The emulsion was cooled to room temperature before adding, one by one, the ingredients of phase C. The final emulsion was characterized by drops between 1 µm and 20 µm in size.
The stability of the merocyanines in formulation was evaluated after storage of the formulations for 2 months. It was established by UPLC assay of the residual merocyanine content after 2 months at 45°C relative to the residual content after 2 months at 4°C. The percentage of merocyanine degradation is expressed as:
The sun protection factor (SPF) was determined according to the in vitro method described by
The stability results show that the merocyanine of the invention (compound (2)), formulated in the emulsified compositions 5 and 7 of the invention, is chemically more stable than the merocyanine outside the invention (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanamide in the emulsified compositions 6 and 8.
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