Cosmetic or dermatological composition comprising at least one merocyanin and one hydrotrope
Patent Information
- Application Number
- FR2021013867
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-12-17
- Publication Date
- 2025-03-21
- Estimated Expiration
- 2041-12-17
Abstract
Description
Title of the invention: Cosmetic or dermatological composition comprising at least one merocyanine and one hydrotrope Technical field
[0001] The present invention relates to the field of care and / or makeup of keratin materials, in particular the care of keratin materials, in particular the skin.
[0002] In particular, the present invention relates to the field of sun protection and more particularly relates to photoprotective cosmetic or dermatological compositions dedicated to the anti-UV protection of keratin materials which have advantageous properties in terms of sensory experience and stability.
[0003] For the purposes of the present invention, the term "keratin materials" is intended to denote in particular the skin, the lips and / or the eyelashes, in particular the skin and / or the lips, and preferably the skin of the body and / or the face, and more preferably of the face. Prior art
[0004] It is known that radiation with a wavelength between 280 nm and 400 nm allows the tanning of the human epidermis and that radiation with a wavelength between 280 and 320 nm, known as UV-B rays, harms the development of natural tanning. Exposure is also likely to induce an alteration of the biomechanical properties of the epidermis which results in the appearance of wrinkles leading to premature aging of the skin.
[0005] It is also known that UV-A rays with a wavelength between 320 and 400 nm penetrate deeper into the skin than UV-B rays. UV-A rays cause immediate and persistent browning of the skin. Daily exposure to UVA rays, even for short periods, under normal conditions can lead to a degradation of collagen and elastin fibers which results in a change in the micro-relief of the skin, the appearance of wrinkles and irregular pigmentation (brown spots, uneven skin tone).
[0006] Protection against UVA and UVB radiation is therefore necessary. An effective photoprotection product must protect against both UVA and UVB radiation.
[0007] To date, a wide variety of photoprotective compositions have been proposed to remedy the effects induced by UVA and / or UVB radiation. They generally contain organic UV filters and / or inorganic UV filters which function according to their own chemical nature and according to their own properties by absorption, reflection, or diffusion of UV radiation. They generally contain mixtures of liposoluble organic filters and / or hydrosoluble UV filters. solubles associated with metal oxide pigments such as titanium dioxide or zinc oxide.
[0008] Many cosmetic compositions intended to limit the darkening of the skin, improve the color and homogeneity of the complexion have been proposed to date. It is well known in the field of sunscreens that such compositions can be obtained by using UV filters, and in particular UVB filters. Some compositions may also contain UVA filters. This filtering system must cover UVB protection in order to limit and control the neosynthesis of melanin promoting overall pigmentation, but must also cover UVA protection in order to limit and control the oxidation of the already existing melanin leading to the darkening of the skin color.
[0009] However, it is extremely difficult to find a composition containing a particular combination of UV filters which would be specially adapted to the photoprotection of the skin and particularly to an improvement in the quality of the skin both in terms of color and its mechanical properties of elasticity.
[0010] Advantageously, this improvement is particularly sought after on already pigmented skin in order to not increase either the pigment load in melanin or the structure of the melanin already present within the skin.
[0011] The majority of organic UV filters consist of aromatic compounds absorbing in the wavelength range between 280 and 370 nm. In addition to their solar radiation filtering power, the desired photoprotection compounds must also have good cosmetic properties, good solubility in common solvents, as well as good photostability alone or in combination with other UV filters. They must also be colorless or at least have a color that is cosmetically acceptable to the consumer.
[0012] One of the main drawbacks known to date of these compositions is that these filtering systems have insufficient effectiveness against UV radiation and particularly against long UVA radiation with wavelengths beyond 370 nm in order to control photo-induced pigmentation and its development by a system filtering UV over the entire UV spectrum.
[0013] Among all the compounds that have been recommended for this purpose, an interesting family of UV filters has been proposed which consists of carbonaceous merocyanine derivatives.
[0014] In particular, numerous cosmetic compositions comprising merocyanine-type UV filters are known in the state of the art, for example in patent US 4,195,999, application WO 2004 / 006878, document IP COM Journal 4 (4), 16 No. IPCOM000011179D published on March 4, 2004, or in application WO 2014 / 111570.
[0015] These compounds have very good filtration properties in the long UVA radiation. In addition, the use of these filters in cosmetic products is considered safe, does not present acute toxicity, and does not induce eye irritation, skin sensitization or genotoxicity.
[0016] Consequently, there has been a long-standing attempt to formulate merocyanine-type UV filters in the cosmetic and dermatological fields, in different galenic forms, due to its numerous beneficial properties, particularly in large quantities, for example of the order of 0.1% to 3% by weight.
[0017] However, these UV filters have a poorly satisfactory solubility in usual solvents, and an unsatisfactory photo-stability for certain merocyanines.
[0018] In order to search for other merocyanines having better solubility in usual solvents and better photostability, application WO 2013 / 011094 proposed merocyanines comprising polar groups consisting of hydroxyl and ether functions which show good long UVA filtration efficiency. However, the solubility in oils of these particular merocyanines is not yet fully satisfactory, and often requires a tedious formulation process. Furthermore, the large quantities of solvent required to solubilize this type of merocyanine can lead to cosmetic problems such as a sticky and greasy effect on application.
[0019] Furthermore, many cosmetic galenics, such as serums or aqueous gels, are devoid of a fatty phase. Thus, this solution does not address the problem encountered with such compositions.
[0020] It is therefore necessary to be able to formulate merocyanine-type UV filters in an aqueous medium. In particular, for cosmetic and performance benefits, it is advantageous for this aqueous medium to be single-phase. However, these filters prove to be very poorly soluble in such a medium. For example, the merocyanine (C) synthesized in example A4 below only has a solubility in water of the order of 0.5 g / L at 20°C, which proves detrimental to the manifestation of its filtering performance.
[0021] Consequently, it remains very difficult to implement merocyanine-type compounds in aqueous phases, while maintaining satisfactory sensory results, and with the lowest possible environmental impact. Statement of the invention
[0022] The present invention aims to solve the aforementioned technical problems.
[0023] In view of the above, it is thus clear that there remains a need for consumers to provide cosmetic and / or dermatological compositions comprising merocyanine-type UV filters in aqueous phase, while having satisfactory cosmetic properties, in particular with regard to the sensory properties upon application.
[0024] There therefore remains a need to improve the aqueous solubility of these merocyanines in photoprotective formulations, particularly over time.
[0025] In particular, there remains a need to increase the aqueous solubility of merocyanine-type filters by limiting the use of co-solvents having an impact on sensoriality.
[0026] There therefore remains a need for a cosmetic and / or dermatological composition, in particular phytoprotective compositions, containing merocyanine-type filters in the aqueous phase, and which provide a good level of sensory pleasure, whether during application to the skin or after drying.
[0027] Finally, there also remains a need to have compositions compatible with current consumer requirements, particularly from an environmental point of view.
[0028] The present invention aims precisely to meet these needs. Summary of the invention
[0029] Thus, according to a first aspect, the present invention relates to a cosmetic or dermatological composition, in particular for making up and / or caring for keratin materials, comprising at least one aqueous phase and: - at least one merocyanine of the following formula (I), as well as its geometric isomeric forms E / E- or E / Z-:
[0030] [Chem.l]
[0031] in which: - A is -O- or -NH; - R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted by one or more O; and - at least one hydrotrope selected from nicotinamide, caffeine, salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof.
[0032] The Applicant has surprisingly discovered that by using particular hydrotropes, it is possible to improve the solubility of these merocyanines in an aqueous phase over time and at low temperature. This discovery is the basis of the present invention.
[0033] In particular, the specific hydrotropes used in the compositions according to the invention make it possible to increase the aqueous solubility of these merocyanines, and to prevent the phase separation of the composition containing them.
[0034] According to another of its aspects, the present invention also relates to a cosmetic process, in particular non-therapeutic, for caring for keratin materials, in particular of the body and / or the face, comprising at least one step of applying to said keratin materials a composition as defined above.
[0035] Other characteristics, aspects and advantages of the invention will appear on reading the detailed description which follows. Detailed description
[0036] A composition according to the invention is cosmetic and / or dermatological, and preferably is cosmetic.
[0037] A composition according to the invention is generally suitable for topical application to the skin and therefore generally comprises a physiologically acceptable medium, i.e. compatible with the skin.
[0038] It is preferably a cosmetically acceptable medium, that is to say which has a pleasant color, odor and feel and does not generate unacceptable discomfort, that is to say tingling, tightness, redness, likely to discourage the user from applying this composition. Merocyanines
[0039] As mentioned previously, a composition according to the invention comprises at least one merocyanine of the following formula (I), as well as its E / E- or E / Z- isomeric geometric forms:
[0040] [Chem.2]
[0041] in which: - A is -O- or -NH; - R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkinyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted by one or more O.
[0042] As indicated above, the merocyanine compounds of the invention can be in their geometric isomeric forms E / E-, E / Z-:
[0043] [Chem.3]
[0044] Preferably, in the compounds of formula (I), A is -O- and R is a C 1 -C 22 alkyl, which may be interrupted by one or more O.
[0045] Among the compounds of formula (I), at least one compound chosen from the following compounds and their isomeric geometric forms E / E-, E / Z- will be used more particularly:
[0046]
[0047]
[0048] [Tables 1] (A) H 1 t J ethyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} etha noate (E) 1 H 1 ü k J ' 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethan oate (B) S H N- (2Z)-2-cyano-N-(3-methoxypropyl)- 2-{3-[(3-methoxypropyl)amino]cycl ohex-2-en-1 -ylidene} ethanamide (F) (V)xz\,zÔ\ i h 1 ' N 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethan oate (C) H 1 v f ] 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} etha noate (G) 1 H ] " 1 r i 'n 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} ethan oate (D) Cl H 1 k .N, ,x l J N 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)a mino] cyclohex-2-en-1 -ylidene} etha noate According to a more particularly preferred embodiment of the invention, compounds (A) and / or (C) and their mixtures will be used, and even more preferably compound (C) in its geometric configuration E / E and / or E / Z. Thus, preferably, a composition according to the invention comprises 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylidene}ethanoate (C), also called Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate, in its geometric configuration E / E and / or E / Z.
[0049] The E / Z form has the following structure:
[0050] [Chem.4]
[0051] The E / E form has the following structure:
[0052] [Chem.5]
[0053] According to a preferred embodiment, a composition according to the invention comprises at least one merocyanine of formula (I) as defined above, in a content varying from 0.1% to 25% by weight, preferably from 0.2% to 20% by weight, more preferably from 0.5% to 10% by weight, and even better from 1% to 5% by weight, relative to the total weight of the composition.
[0054] Generally speaking, merocyanine-type compounds can be prepared according to known methods, as described for example in J. Org. Chem. USSR (English Translation) 26(8), p. 1562f (1990); J. Heterocycl. Chem. 33(3), p. 763-766 (1996); Khimiya Geterotsiklicheskikh Soedinenii 11, p. 1537-1543 (1984); Khimiya Geterotsiklicheskikh Soedinenii 3, p. 397-404 (1982); Chem. Heterocycl. Comp. (English Translation) 24(8), 914-919 (1988) and in Synthetic Communications Vol. 33, No. 3, 2003, p 367-371.
[0055] As regards the compounds of formula (I) more particularly considered according to the invention, and which have the specificity of possessing a carbocyclic ring containing 6 carbon atoms, they can be prepared according to the protocols described in Pat. Appl. WO 2007 / 071582, in IP.com Journal (2009), 9(5A), 29-30 IPCOM000182396D under the title “Process for producing 3-amino-2-cyclohexan-l-ylidene compounds” and in US-A-4,749,643 on col, 13, line 66 - col. 14, line 57 and the references cited in this regard.
[0056] In particular, compounds of formula (I) of Table 1 above can be synthesized according to the synthesis scheme described in the publication by B. Winkler et al., Te- trahedron Letters, 55 (2014) 1749-1751, which is entitled “A cyclic merocyanine UV-A absorber: mechanism of formation and crystal structure”, and represented below, for compounds of formula (I):
[0057] [Chem.6]
[0058] As for compound (C) of table 1, the following synthesis scheme is preferred.
[0059] [Chem.7]
[0060] The synthesis illustrated by this diagram is detailed in particular in example A4 below. Hydrotrope
[0061] As mentioned previously, a composition according to the invention comprises at least one hydrotrope chosen from nicotinamide, caffeine, salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PC A), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof
[0062] According to a preferred embodiment, a composition according to the invention comprises at least one hydrotrope chosen from nicotinamide, caffeine and their mixtures. In particular, such a composition may further comprise at least one additional hydrotrope selected from salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof, and preferably at least one salt of salicylic acid.
[0063] According to an alternative embodiment, a composition according to the invention comprises at least one hydrotrope chosen from nicotinamide, caffeine and one of their mixtures combined with at least one salicylic acid salt.
[0064] The salts of salicylic acid may in particular be chosen from sodium salicylate, lysine salicylate, arginine salicylate, magnesium salicylate, and mixtures thereof.
[0065] Preferably, the salt of salicylic acid is sodium salicylate.
[0066] According to a preferred embodiment, a composition according to the invention comprises at least nicotinamide, as hydrotope.
[0067] According to a particular embodiment, a composition according to the invention comprises nicotinamide and sodium salicylate.
[0068] The hydrotrope(s) are present in the composition according to the invention, in an amount effective for solubilizing in water, the merocyanine(s) of formula (I) as described above.
[0069] The content of hydrotrope(s) according to the invention present in the compositions according to the invention may vary from 0.1% to 20% by weight, in particular from 0.1% to 10% by weight, preferably from 0.5% to 10% by weight, in particular from 0.5% to 3% by weight relative to the total weight of the composition.
[0070] In particular, the mass ratio of merocyanine(s) of formula (I) / hydrotrope(s) according to the invention, of a composition according to the invention varies from 0.01 to 8, preferably from 0.02 to 5, in particular from 0.05 to 3, and more preferably from 0.1 to 1.5.
[0071] According to a particular embodiment, a composition according to the invention comprises at least two distinct hydrotropes chosen from nicotinamide, caffeine, and sodium salicylate, and the mass ratio of merocyanine(s) of formula (I) / hydrotropes of a composition according to the invention varies from 0.01 to 5, preferably from 0.02 to 3, in particular from 0.05 to 2, and more preferably from 0.1 to 1.5.
[0072] According to a particular embodiment, a composition according to the invention comprises two distinct hydrotropes, preferably nicotinamide and caffeine and the mass ratio between these two hydrotropes varies from 0.2 to 5, in particular from 0.5 to 3, and more preferably from 0.8 to 1.2. Aqueous phase
[0073] A composition according to the invention comprises an aqueous phase, and optionally an oily phase.
[0074] The aqueous phase comprises water and optionally a water-soluble organic solvent and is preferably single-phase.
[0075] According to a preferred embodiment, the composition according to the present invention comprises a water content of between 10% and 98% by weight, preferably between 25% and 90% by weight, and more preferably between 35% and 85%, relative to the total weight of the composition.
[0076] By "water-soluble organic solvent" according to the present invention is meant a compound which is liquid at room temperature and miscible with water (miscibility in water greater than 50% by weight at 25°C and atmospheric pressure).
[0077] The water-soluble solvents that can be used in the composition of the invention can also be volatile. In particular, to obtain compositions with a BC3 content > 0.9%, a water-soluble co-solvent will be used in addition to the hydrotropes.
[0078] Among the water-soluble solvents which can be used in the composition according to the invention, mention may be made in particular of lower monoalcohols having from 1 to 5 carbon atoms such as ethanol and isopropanol, polyols and also alkylene carbonates.
[0079] According to a preferred embodiment, the composition according to the invention further comprises at least one alcohol, in particular a mono-alcohol, and preferably ethanol.
[0080] Preferably, in a composition according to the invention, the alcohol may be present in a content varying from 0.5% to 30% by weight, better still from 2.0% to 25% by weight, preferably from 3.0% to 15% by weight, relative to the total weight of said composition.
[0081] According to an alternative embodiment, the aqueous phase of a composition according to the invention may comprise at least one C2-C32 polyol.
[0082] For the purposes of the present invention, the term “polyol” means any organic molecule comprising at least two free hydroxyl groups.
[0083] Preferably, a polyol according to the present invention is present in liquid form at room temperature.
[0084] A polyol suitable for the invention may be a compound of alkyl type, linear, branched or cyclic, saturated or unsaturated, bearing on the alkyl chain at least two -OH functions, in particular at least three -OH functions, and more particularly at least minus four -OH functions.
[0085] The polyols suitable for the formulation of a composition according to the present invention are in particular those having in particular from 2 to 32 carbon atoms, preferably from 3 to 16 carbon atoms.
[0086] The polyol may be chosen, for example, from ethylene glycol, pentaerythritol, trimethylolpropane, propylene glycol, 1,3-propanediol, butylene glycol, isoprene glycol, pentylene glycol, hexylene glycol, C3 and C4 ketones and C2-C4 aldehydes, caprylyl glycol, glycerol, polyglycerols, such as glycerol oligomers such as diglycerol, polyethylene glycols, and mixtures thereof.
[0087] According to a preferred embodiment of the invention, said polyol is chosen from ethylene glycol, pentaerythritol, trimethylolpropane, pentylene glycol, propylene glycol, dipropylene glycol (DPG), caprylyl glycol, glycerol, polyglycerols, polyethylene glycols (PEG), and mixtures thereof.
[0088] According to a particular embodiment, the composition of the invention may comprise at least one polyol, in particular chosen from glycerin, caprylyl glycol, propylene glycol, pentylene glycol, dipropylene glycol (DPG), PEG-8, and mixtures thereof.
[0089] According to a preferred embodiment, the composition of the invention may comprise at least one polyol, in particular chosen from propylene glycol, pentylene glycol, dipropylene glycol (DPG), and mixtures thereof.
[0090] Preferably, the composition of the invention may comprise at least dipropylene glycol (DPG), as polyol.
[0091] When they are present, the polyol(s) are preferably present in a composition according to the invention in a content ranging from 0.5% to 40% by weight, better still from 3% to 30% by weight, preferably from 5% to 25% by weight, relative to the total weight of said composition.
[0092] According to another particular embodiment, the composition of the invention may comprise at least one alkylene carbonate, in particular chosen from those of the following formula (II):
[0093] [Chem 8]
[0094] 0 (II) ,P
[0095] in which
[0096] R' denotes a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical;
[0097] R” represents a hydrogen atom, a linear or branched C1-C6 alkyl radical, a linear or branched C1-C4 hydroxyalkyl radical; and
[0098] m is 1, 2 or 3.
[0099] Preferably, the radical R' represents a hydrogen atom, a linear or branched C1-C4 alkyl radical, a linear or branched C1-C2 hydroxyalkyl radical.
[0100] R” represents a hydrogen atom, a linear or branched C1-C2 alkyl radical, a linear or branched C1-C2 hydroxyalkyl radical
[0101] Preferably m is 1.
[0102] As particularly advantageous examples of alkylene carbonates, mention may be made of compounds for which the radical R' represents a hydrogen atom (corresponding to ethylene carbonate), a methyl group (corresponding to propylene carbonate), ethyl (corresponding to 1,2-butylene carbonate), hydroxymethyl (R'= -CH2OH; corresponding to glycerin carbonate).
[0103] Preferably, the alkylene carbonate used is propylene carbonate.
[0104] Alkyl or alkylene carbonates may be present in the compositions according to the invention at concentrations preferably ranging from 0.1 to 98% by weight, particularly from 0.5 to 50% by weight, more preferably from 1 to 20% by weight and even more particularly from 1 to 10% by weight, in particular 1 to 6% by weight relative to the total weight of the composition.
[0105] As is apparent from the examples given below, an increase in the solubility of the merocyanines of formula (I) can be observed when one of the abovementioned organic solvents is used in conjunction with at least one hydrotrope. This effect is particularly interesting for solubilizing a significant quantity of merocyanine in an aqueous medium.
[0106] Thus, according to an alternative embodiment, a composition according to the invention may contain, in addition to at least one hydrotrope, at least one organic solvent chosen in particular from alcohols, in particular polyols and alkylene carbonates.
[0107] In addition to the aforementioned solvents, a composition according to the invention may also comprise at least one organic solvent chosen from:
[0108] - ketones which are liquid at room temperature, such as methyl ethyl ketone, methyliso- butyl ketone, diisobutyl ketone, isophorone, cyclohexanone, acetone;
[0109] - cyclic ethers, such as γ-butyrolactone;
[0110] - short-chain esters (having 3 to 8 carbon atoms in total), such as acetate ethyl acetate, butyl acetate, methyl acetate, propyl acetate, isopropyl acetate, isopentyl acetate, methoxypropyl acetate, butyl lactate;
[0111] - ethers which are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether;
[0112] - alkanes which are liquid at room temperature, such as decane, heptane, dodecane, cyclohexane;
[0113] - alkyl sulfoxides, such as dimethyl sulfoxide;
[0114] - aldehydes which are liquid at room temperature, such as benzaldehyde, acetaldehyde;
[0115] - ethyl 3-ethoxypropionate;
[0116] - acetals, such as methylal; and
[0117] - their mixture s.
[0118] The aqueous phase may further comprise any water-soluble or water-dispersible compound compatible with an aqueous phase such as stabilizing agents, gelling agents, film-forming polymers, thickeners, surfactants and mixtures thereof.
[0119] Preferably, the aqueous phase is present in a composition according to the invention in a content ranging from 30% to 100% by weight, preferably from 35% to 99.5% by weight, and more preferably from 45% to 99% by weight, relative to the total weight of said composition. Fat phase
[0120] As mentioned previously, a composition according to the invention may comprise at least one fatty phase.
[0121] For the purposes of the invention, the term “fatty phase” means a phase comprising at least one oil and all of the liposoluble and lipophilic ingredients and fatty substances used for the formulation of the compositions of the invention.
[0122] In particular, a composition according to the invention may comprise varying from 0.5% to 80% by weight, preferably from 1% to 40% by weight, and more preferably from 3% to 20% by weight, of fatty phase, relative to the total weight of the composition.
[0123] The fatty phase of the composition according to the invention may comprise oils, waxes, pasties, and / or silicone compounds, and preferably at least one oil, in particular a cosmetic oil. Oils
[0124] By "oil" is meant a non-aqueous compound, immiscible with water, liquid at room temperature (20°C) and atmospheric pressure (760 mm Hg).
[0125] A fatty phase suitable for the preparation of the compositions, in particular cosmetic compositions, according to the invention may comprise hydrocarbon, silicone, fluorinated or non-fluorinated oils, or mixtures thereof.
[0126] The oils may be volatile or non-volatile.
[0127] They can be of animal, vegetable, mineral or synthetic origin.
[0128] The fatty phase may comprise, in addition to the merocyanine filter(s) and possibly actually lipophilic complementary filters at least one volatile or non-volatile hydrocarbon oil and / or one volatile and / or non-volatile silicone oil and / or one volatile and / or non-volatile fluorinated oil.
[0129] For the purposes of the present invention, the term “hydrocarbon oil” means an oil containing mainly hydrogen and carbon atoms.
[0130] The term “silicone oil” means an oil comprising at least one silicon atom, and in particular at least one Si-O group.
[0131] The term “fluorinated oil” means an oil comprising at least one fluorine atom.
[0132] The oils may optionally comprise oxygen, nitrogen, sulfur and / or phosphorus atoms, for example, in the form of hydroxyl or acid radicals. Volatile oils
[0133] For the purposes of the invention, the term "volatile oil" means any oil capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure. Volatile oil is a volatile cosmetic compound, liquid at room temperature, having in particular a non-zero vapor pressure, at room temperature and atmospheric pressure, in particular having a vapor pressure ranging from 0.13 Pa to 40,000 Pa (103 to 300 mm Hg), in particular ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and more particularly ranging from 1.3 Pa to 1,300 Pa (0.01 to 10 mm Hg).
[0134] Volatile oils can be hydrocarbon or silicone.
[0135] Among the volatile hydrocarbon oils having from 8 to 16 carbon atoms, mention may in particular be made of branched C8-Ci6 alkanes such as C8-Ci6 isoalkanes (also called isoparaffins), isododecane, isodecane, isohexadecane and, for example, oils sold under the trade names Isopars or Permetyls, branched C8-Ci6 esters such as isohexyl neopentanoate, and mixtures thereof.
[0136] Mention may also be made of volatile linear alkanes comprising from 8 to 16 carbon atoms, in particular from 10 to 15 carbon atoms, and more particularly from 11 to 13 carbon atoms, for example such as n-dodecane (Ci2) and n-tetradecane (CM) sold by Sasol respectively under the references Parafol 12-97 and Parafol 14-97, as well as their mixtures, the undecane-tridecane mixture, the mixtures of n-undecane (Cn) and n-tridecane (Cn) obtained in examples 1 and 2 of application WO 2008 / 155059 from Cognis, and their mixtures.
[0137] As volatile silicone oils, mention may be made of linear volatile silicone oils such as hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane and do-decamethylpentasiloxane.
[0138] As cyclic silicone volatile oils, mention may be made of: hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopenta-siloxane, cyclohexasiloxane and dodecamethylcyclohexasiloxane, and in particular cyclohexasiloxane.
[0139] Fluorinated volatile oils, such as nonafluoromethoxybutane, nonafluoromethoxybutane, decafluoropentane, tetradecafluorohexane, dodecafluoropentane and mixtures thereof, may also be used. Non-volatile oils
[0140] By “non-volatile” is meant an oil whose vapor pressure at room temperature and atmospheric pressure is non-zero and less than 103 mm Hg (0.13 Pa).
[0141] The non-volatile oils may, in particular, be chosen from hydrocarbon, fluorinated and / or non-volatile silicone oils.
[0142] As non-volatile hydrocarbon oil, we can notably cite: - hydrocarbon oils of animal origin, - linear or branched hydrocarbons, of mineral or synthetic origin such as petroleum jelly, polydecenes, hydrogenated polyisobutene, such as parleam, squalane, and their mixtures, - non-volatile alkanes, preferably with a viscosity of less than 20 mPa.s at 20°C measured with a Lamy Rheology Rhéomat RM 100® viscometer. “Non-volatile alkane” means a hydrocarbon cosmetic oil, liquid at room temperature, having in particular a vapor pressure at 20°C of less than 0.01 kPa, according to the definition of a Volatile Organic Compound (VOC) in Article 2 of European Council Directive 1999 / 13 / EC of March 11, 1992: “Any organic compound having a vapor pressure of 0.01 kPa or more at a temperature of 293.15 K”. In particular, the non-volatile alkanes comprise from 10 to 30 carbon atoms, in particular from 12 to 26 carbon atoms, and more particularly from 15 to 19 carbon atoms, and preferably a mixture of alkanes of 15 to 19 carbon atoms, for example the products marketed under the references Emogreen L19 and Emosmart L19 from Seppic, - hydrocarbon oils of vegetable origin, such as glyceride triesters which are generally triesters of fatty acids and glycerol whose fatty acids can have chain lengths varying from 4 to 24 carbon atoms, the latter being able to be linear or branched, saturated or unsaturated; These oils include wheat germ, sunflower, grape seed, sesame, corn, apricot, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, and rose oil. muscat; or the triglycerides of caprylic / capric acids such as those sold by the company Stéarineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel,- synthetic ethers having from 10 to 40 carbon atoms, such as dicapryl ether, - synthetic esters, such as oils of formula RiCOOR2, in which Ri represents a residue of a linear or branched fatty acid containing from 1 to 40 carbon atoms and R2 represents a hydrocarbon chain, in particular a branched chain containing from 1 to 40 carbon atoms provided that Ri + R2 is greater than or equal to 10, such as for example Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, alkyl benzoate having between 12 and 15 carbon atoms, such as the product sold under the trade name “Finsolv TN” or “Witconol TN” by the company Witco or “Tegosoft TN” by the company Evonik Goldschmidt, 2-ethylphenyl benzoate such as commercial product sold under the name "X-Tend 226" by the company ISP, isopropyl lanolate, hexyl laurate, diisopropyl adipate, isononyl isononanoate, oleyl erucate,2-ethylhexyl palmitate, isostearyl isostearate, diisopropyl sebacate such as the product sold under the name "Dub Dis" by the company Stearinerie Dubois, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, diisostearyl malate; and pentaerythritol esters; citrates, such as the ester of C3-C22 tricarboxylic acid and C1-C6 alcohols with the INCI name Tiethyl Citrate, for example that sold under the name Citrofol AI Extra by the company Jungbunzlauer; tartrates such as linear dialkyl tartrates having 12 or 13 carbon atoms, for example those sold under the name Cosmacol ETI by the company Enichem Augusta Industriale as well as linear dialkyl tartrates having between 14 and 15 carbon atoms, for example those sold under the name Cosmacol ETL by the same company, and acetates, - fatty amides such as Isopropyl N-lauroyl sarcosinate, for example the product sold under the trade name “Eldew SL205” from Ajinomoto, - polyol esters and pentaerythritol esters, such as dipentaerythritol tetrahydroxystearate / tetraisostearate, - fatty alcohols which are liquid at room temperature with a branched and / or unsaturated carbon chain having from 12 to 26 carbon atoms, such as octyldodecanol, isostearyl alcohol, oleyl alcohol, 2-hexyldecanol, 2-butyloctanol, 2-undecylpentadecanol, - higher fatty acids C12-C22, such as oleic acid, linoleic acid, linolenic acid, and mixtures thereof, - carbonates, such as dicaprylyl carbonate, for example the product sold under the name “Cetiol CC” by the company Cognis; - non-phenylated silicone oils, such as caprylyl methycone, and - phenylated silicone oils, such as, for example, phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenylsiloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, and 2-phenylethyl trimethylsiloxysilicates, dimethicones or phenyl trimethicone with a viscosity of less than or equal to 100 cSt, trimethylpentaphenyltrisiloxane, and mixtures thereof; as well as mixtures of these different oils. Other fatty substances
[0143] A fatty phase according to the invention may further comprise, mixed with or dissolved in an oil, other fatty substances.
[0144] Other fatty substances which may be present in the oily phase are, for example: - fatty acids containing 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; - waxes, other than glyceryl trihydroxystearate, such as lanolin, beeswax, Camauba or Candellila wax, paraffin waxes, lignite waxes or microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes; - silicone resins such as trifluoromethyl-Ci-C4-alkyldimethicone and trifluoropropyldimethicone; - silicone elastomers such as products marketed under the names “KSG” by the company Shin-Etsu, under the names “Trefil” or “BY29” by the company Dow Corning or under the names “Gransil” by the company Grant Industries; - a gum chosen from silicone gums (dimethiconol), - a pasty compound, such as polymeric or non-polymeric silicone compounds, esters of an oligomeric glycerol, arachidyl propionate, fatty acid triglycerides and their derivatives, - and their mixtures.
[0145] As a fatty substance, a composition according to the invention may comprise at least one fatty alcohol wax. Such waxes may be chosen from lauryl or lauryl alcohol, myristyl or myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol, ceryl alcohol, montanyl alcohol, myricyl alcohol and mixtures thereof.
[0146] As a fatty substance, a composition according to the invention may comprise in particular at least one butter, more particularly a vegetable butter.
[0147] The vegetable butter(s) suitable for the invention are preferably chosen from the group comprising avocado butter, cocoa butter, shea butter, butter kokum butter, mango butter, murumuru butter, coconut butter, apricot kernel butter, sal butter, urucum butter and their mixtures, and in particular is shea butter.
[0148] These fatty substances can be chosen in a variety of ways by those skilled in the art in order to prepare a composition having the desired properties, for example consistency or texture.
[0149] According to a preferred embodiment, a composition according to the invention comprises at least one non-volatile oil, preferably at least one non-volatile hydrocarbon oil, in particular chosen from linear or branched hydrocarbons, of mineral or synthetic origin, non-volatile alkanes, hydrocarbon oils of vegetable origin, synthetic esters, fatty amides, carbonates, as well as mixtures of these different oils.
[0150] In particular, such non-volatile hydrocarbon oils may be present in a composition according to the invention in a content ranging from 2.0% to 20.0% by weight, preferably from 2.0% to 15.0% by weight, relative to the total weight of the composition.
[0151] According to a preferred embodiment, a composition according to the invention contains at least one oil chosen from squalane, mixtures of alkanes with 15 to 19 carbon atoms, triglycerides of caprylic / capric acids, alkyl benzoates with between 12 and 15 carbon atoms, diisopropyl adipate, 2-ethylhexyl palmitate, diisopropyl sebacate, C3-C22 tricarboxylic acid ester of C1-C6 alcohols with the INCI name Tiethyl Citrate, Isopropyl N-lauroyl sarcosinate, dicaprylyl carbonate, and mixtures thereof.
[0152] Preferably, a composition according to the invention comprises less than 2.0% by weight of silicone oil(s), in particular less than 1.0% by weight of silicone oil(s), preferably less than 0.5% by weight of silicone oil(s), relative to the total weight of the composition, and more preferably is free of silicone oil(s).
[0153] Preferably, a composition according to the invention comprises a fatty phase containing at least one fatty substance.
[0154] According to a preferred embodiment, a composition according to the invention comprises at least one non-volatile hydrocarbon oil, and preferably at least one non-volatile ester oil.
[0155] According to a preferred embodiment, a composition according to the invention further comprises at least one solid fatty substance, in particular a fatty acid comprising from 8 to 30 carbon atoms, and more preferably stearic acid. Additional UV filters
[0156] A composition according to the invention may comprise at least one complementary UV filter distinct from the merocyanines of formula (I) previously described.
[0157] In particular, a composition according to the invention may comprise at least one compound filtering UVA and / or UVB rays distinct from the merocyanines of formula (I) previously described.
[0158] The compositions according to the invention may thus additionally contain one or more complementary UV filters chosen from hydrophilic, lipophilic or insoluble organic UV filters and / or one or more mineral pigments. Preferably, it will consist of at least one hydrophilic, lipophilic or insoluble organic UV filter.
[0159] By "hydrophilic UV filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation capable of being completely dissolved in the molecular state in a liquid aqueous phase or of being solubilized in colloidal form (for example in micellar form) in a liquid aqueous phase.
[0160] By "lipophilic filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation capable of being completely dissolved in the molecular state in a liquid fatty phase or of being solubilized in colloidal form (for example in micellar form) in a liquid fatty phase.
[0161] By "insoluble UV filter" is meant any organic or inorganic cosmetic or dermatological compound filtering UV radiation having a solubility in water of less than 0.5% by weight and a solubility of less than 0.5% by weight in most organic solvents such as paraffin oil, fatty alcohol benzoates and fatty acid triglycerides, for example Miglyol 812® marketed by the company DYNAMIT NOBEL. This solubility, achieved at 70°C, is defined as the quantity of product in solution in the solvent at equilibrium with an excess of solid in suspension after returning to room temperature. It can easily be evaluated in the laboratory.
[0162] The complementary organic UV filters are in particular chosen from cinnamic compounds; anthranilate compounds; salicylic compounds; dibenzoylmethane compounds; benzylidene camphor compounds; benzophenone compounds; [3,[3-diphenylacrylate] compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds in particular those cited in patent US5624663; benzimidazole derivatives; imidazoline compounds; bis-benzoazolyl compounds as described in patents EP 0 669 323 and US 2,463,264; p-aminobenzoic compounds (PABA); methylene bis-(hydroxyphenyl benzotriazole) compounds as described in applications US 5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP 0 893 119; benzoxazole compounds as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 10162844;filter polymers and filter silicones such as those described in particular in application WO-93 / 04665; dimers derived from α-alkylstyrene such as those; described in patent application DE 19855649; 4,4-diarylbutadiene compounds as described in applications EP 0 967 200, DE 19746654, DE 19755649, EP 1 008 586, EP 1 133 980 and EP 0 133 981 and mixtures thereof.
[0163] Examples of organic photoprotective agents include those designated below by their INCI name.
[0164] Cinnamic compounds: - Ethylhexyl Methoxycinnamate, sold in particular under the trade name Parsol MCX® by DSM Nutritial Products, - Isopropyl Methoxycinnamate, - Isoamyl p-Methoxycinnamate, sold under the trade name Neo Heliopan E 1000® by Symrise, - DEA Methoxycinnamate, - Diisopropyl Methylcinnamate, - Glyceryl Ethylhexanoate Dimethoxycinnamate.
[0165] Dibenzoylmethane compounds: - Butyl Methoxydibenzoylmethane, sold in particular under the trade name Parsol 1789® by DSM Nutritial Products, - Isopropyl Dibenzoylmethane.
[0166] Para-aminobenzoic compounds: - PABA, - Ethyl PABA, - Ethyl Dihydroxypropyl PABA, - Ethylhexyl Dimethyl PABA, sold in particular under the name “Escalol 507®” by ISP, - Glyceryl PABA, - PEG-25 PABA, sold under the name “Uvinul P 25®” by BASF.
[0167] Salicylic compounds: - Homosalate, sold under the name “Eusolex HMS®” by Rona / EM Industries, - Ethylhexyl Salicylate, sold under the name “Neo Heliopan OS®” by Symrise, - Dipropylene glycol Salicylate, sold under the name “Dipsal®” by Scher, - TEA Salicylate, sold under the name “Neo Heliopan TS®” by Symrise.
[0168] Compounds [3.[3-diphenylacrylate: - Octocrylene, sold in particular under the trade name “Uvinul N 539®” by BASF, - Etocrylene, sold in particular under the trade name “Uvinul N 35®” by BASF.
[0169] Benzophenone compounds: - Benzophenone-1, sold under the trade name “Uvinul 400®” by BASF, - Benzophenone-2, sold under the trade name “Uvinul D 50®” by BASF, - Benzophenone-3 or Oxybenzone, sold under the trade name “Uvinul M 40®” by BASF, - Benzophenone-4, sold under the trade name “Uvinul MS 40®” by BASF, - Benzophenone-5, - Benzophenone-6, sold under the trade name “Helisorb 11®” by Norquay, - Benzophenone-8, sold under the trade name “Spectra-Sorb UV-24®” by American Cyanamid, - Benzophenone-9, sold under the trade name* Uvinul DS 49®» by BASF, - Benzophenone-12, - n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate sold under the trade name “Uvinul A Plus ®” or in mixture with octylmethoxycinnamate under the trade name “Uvinul A Plus B®” by the company BASF, 1,1'-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl]phenyl]-methan one (CAS 919803-06-8) as described in application WO2007 / 071584; this compound being advantageously used in micronized form (average size of 0.02 to 2 pm) which can be obtained for example according to the micronization process described in applications GB 2 303 549 and EP 0 893 119 and in particular in the form of an aqueous dispersion.
[0170] Benzvlidene camphor compounds: - 3-Benzylidene camphor, manufactured under the name “Mexoryl SD®” by Chimex, - 4-Methylbenzylidene camphor, sold under the name “Eusolex 6300®” by Merck, - Benzylidene Camphor Sulfonic Acid, manufactured under the name “Mexoryl SL®” by Chimex, - Camphor Benzalkonium Methosulfate, manufactured under the name “Mexoryl SO®” by Chimex, - Terephthalylidene Dicamphor Sulfonic Acid, manufactured under the name “Mexoryl SX®” by Chimex, - Polyacrylamidomethyl Benzylidene Camphor, manufactured under the name “Mexoryl SW ®” by Chimex.
[0171] Phenyl benzimidazole compounds: - Phenylbenzimidazole Sulfonic Acid, sold in particular under the trade name “Eusolex 232®” by Merck.
[0172] Bis-benzoazolyl compounds: - Disodium Phenyl Dibenzimidazole Tetra-sulfonate, sold under the trade name “Neo Heliopan AP®” by Haarmann and Reimer.
[0173] Phenyl benzotriazole compounds: - Drometrizole Trisiloxane, sold under the name “Silatrizole®” by Rhodia Chimie.
[0174] Methylene bis-(hvdroxvphénvl benzotriazole) compounds: - Methylene bis-Benzotriazolyl Tetramethylbutylphenol, in particular in solid form such as the product sold under the trade name “Mixxim BB / 100 ®” by Fairmount Chemical or in the form of an aqueous dispersion of micronized particles having an average particle size which varies from 0.01 to 5 pm and more preferably from 0.01 to 2 pm and more particularly from 0.020 to 2 pm with at least one alkylpolyglycoside surfactant of structure CnH2n+iO(C6Hi0O5)xH in which n is an integer from 8 to 16 and x is the average degree of polymerization of the unit (C6Hi0O5) and varies from 1.4 to 1.6 as described in patent GB 2 303 549 in particular sold under the trade name “Tinosorb M®” by BASF or in the form of an aqueous dispersion of micronized particles having an average particle size which varies from 0.02 to 2 pm and more preferably from 0.01 to 1.5 pm and more particularly from 0.02 to 1 pm in the presence of at least one mono-(C8-C20)alkyl-ester of polyglycerol having a degree of polymerization of glycerol of at least 5 such as the aqueous dispersions described in application WO 2009 / 063392.,
[0175] Triazine compounds: - 3,3'-(l,4-Phenylene)bis(5,6-diphenyl-l,2,4-triazine), with the INCI name Phenylene Bis-Diphenyl triazine, with the following chemical formula:
[0176] [Chem.9]
[0177] - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, sold under the trade name “Tinosorb S®” by BASF, - Ethylhexyl Triazone, sold in particular under the trade name “Uvinul T 150®” by BASF, - Diethylhexyl Butamido Triazone, sold under the trade name “Uvasorb HEB®” by Sigma 3V, - dineopentyl 2,4,6-tris-(4'-amino benzalmalonate)-s-triazine, - diisobutyl 2,4,6-tris-(4'-amino benzalmalonate)-s-triazine, - n-butyl 2,4-bis-(4'-aminobenzoate)-6-(aminopropyltrisiloxane)-s-triazine, - 2,4-bis-(4'-aminobenzalmalonate of dineopentyl)-6-(4'-aminobenzoate of n- butyl)-s-triazine, - symmetrical triazine filters substituted by naphthalenyl groups or polyphenyl groups described in US patent 6,225,467, application WO 2004 / 085412 (see compounds 6 and 9) or the document "Symetrical Triazine Derivatives" IP.COM IPCOM000031257 Journal, INC WEST HENRIETTA, NY, US (September 20, 2004) in particular 2,4,6-tris(di-phenyl)-triazine and 2,4,6-tris(ter-phenyl)-triazine which is included in patent applications WO 06 / 035000, WO 06 / 034982, WO 06 / 034991, WO 06 / 035007, WO 2006 / 034992, WO 2006 / 034985, these compounds being used advantageously in micronized form (average particle size of 0.02 to 3 μm) which can be obtained for example according to the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion form, - triazine silicones substituted by two aminobenzoate groups as described in patent EP 0 841 341, in particular 2,4-bis-(n-butyl 4'-aminobenzalmalonate)-6-[(3-{l,3,3,3-tetramethyl-l-[(trimethylsilyloxy]disiloxanyl}propyl)amino]-s-triazine.
[0178] Anthranilic compounds: - Menthyl anthranilate, sold under the trade name “Neo Heliopan MA®” by Symrise.
[0179] Imidazoline compounds: - Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate.
[0180] Benzalmalonate compounds: - Polyorganosiloxane with benzalmalonate functions, such as Polysilicone-15 sold under the trade name “Parsol SLX®” by Hoffmann La Roche.
[0181] 4.4-diarvlbutadiene compounds: - 1,1-dicarboxy (2,2'-dimethyl-propyl)-4,4-diphenylbutadiene.
[0182] Benzoxazole compounds: 2,4-bis-[5-l(diméthylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imin o-l,3,5-triazine vendu sous le nom d’Uvasorb K2A® par Sigma 3V.
[0183] Les filtres organiques préférentiels sont choisis parmi : - Ethylhexyl Methoxycinnamate, - Ethylhexyl Salicylate, - Homosalate, - Butyl Methoxydibenzoylmethane, - Octocrylene, - Phenylbenzimidazole Sulfonic Acid, - Benzophenone-3, - Benzophenone-4, - Benzophenone-5, - 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle, - 4-Methylbenzylidene camphor, - Terephthalylidene Dicamphor Sulfonic Acid, - Disodium Phenyl Dibenzimidazole Tetra-sulfonate, - Méthylène bis-Benzotriazolyl Tetramethylbutylphénol, - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, - Ethylhexyl Triazone, - Diethylhexyl Butamido Triazone, - 2,4,6-tris-(4’-amino benzalmalonate de dinéopentyle)-s-triazine, - 2,4,6-tris-(4’-amino benzalmalonate de diisobutyle)-s- triazine, - 2,4-bis-(4’-aminobenzoate de n-butyle)-6-(aminopropyltrisiloxane)-s-triazine, - 2,4-bis-(4’-aminobenzalmalonate de dinéopentyle)-6-(4’-aminobenzoate de n-butyle)-s-triazine, - 2,4-bis-(n-butyl 4’-aminobenzalmalonate)-6-[(3-{ l,3,3,3-tetramethyl-l-[(trimethylsilyl-oxy]-disiloxany l}propyl)amino]-s-triazine, - 2,4,6-tris-(di-phenyl)-triazine, - 2,4,6-tris-(ter-phenyl)-triazine, - Drometrizole Trisiloxane, - Polysilicone-15, - 1,1-dicarboxy (2,2’-diméthyl-propyl)-4,4-diphénylbutadiène, 2,4-bis-[5-l(diméthylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2-ethylhexyl)-imin o-l,3,5-triazine, - et leurs mélanges.
[0184] Les filtres organiques particulièrement préférés sont choisis parmi : - Ethylhexyl Salicylate, - Homosalate, - Butyl Methoxydibenzoylmethane, - Octocrylene, - 2-(4-diethylamino-2-hydroxybenzoyl)-benzoate de n-hexyle, - Terephthalylidene Dicamphor Sulfonic Acid, - Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, - Ethylhexyl Triazone, - Diethylhexyl Butamido Triazone, - 2,4-bis-(n-butyl 4’-aminobenzalmalonate)-6-[(3-{ l,3,3,3-tetramethyl-l-[(trimethylsilyl-oxy]-disiloxany l}propyl)amino]-s-triazine, - Drometrizole Trisiloxane, - et leurs mélanges.
[0185] The inorganic UV filters used in accordance with the present invention are metal oxide pigments. More preferably, the inorganic UV filters of the invention are metal oxide particles having an average elementary particle size of less than or equal to 0.5 μm, more preferably between 0.005 and 0.5 μm and even more preferably between 0.01 and 0.2 μm, even better between 0.01 and 0.1 μm, and more particularly between 0.015 and 0.05 μm.
[0186] They can be chosen in particular from titanium, zinc, iron, zirconium, cerium oxides or their mixtures.
[0187] Such coated or uncoated metal oxide pigments are described in particular in patent application EP 0 518 773. As commercial pigments, mention may be made of the products sold by the companies Sachtleben Pigments, Tayca, Merck and Degussa.
[0188] Metal oxide pigments may be coated or uncoated.
[0189] Coated pigments are pigments which have undergone one or more surface treatments of a 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 aluminum salts of fatty acids, metal alkoxides (titanium or aluminum), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate.
[0190] The coated pigments are more particularly titanium oxides coated with: - silica, such as the product “Sunveil®” from the company Ikeda, - silica and iron oxide, such as the product “Sunveil F®” from the Ikeda company, - silica and alumina, such as the products “Microtitanium Dioxide MT 500 SA®” and “Microtitanium Dioxide MT 100 SA” from the company Tayca, “Tioveil” from the company Tioxide, - alumina, such as the products “Tipaque TTO-55 (B)®” and “Tipaque TTO-55 (A) ®” from the company Ishihara, and “UVT 14 / 4” from the company Sachtleben Pigments, - alumina and aluminum stearate, such as the products “Microtitanium Dioxide MT 100 T®, MT 100 TX®, MT 100 Z®, MT-01®” from Tayca, the products “Solaveil CT-10 W®” and “Solaveil CT 100®” from Uniqema and the product “Eusolex T-AVO®” from Merck, - silica, alumina and alginic acid, such as the product “MT-100 AQ®” from the company Tayca, - alumina and aluminum laurate, such as the product “Microtitanium Dioxide MT 100 S®” from the company Tayca, - iron oxide and iron stearate, such as the product “Microtitanium Dioxide MT 100 F®” from the company Tayca, - zinc oxide and zinc stearate, such as the product “BR 351®” from the company Tayca, - silica and alumina and treated with a silicone, such as the products “Microtitanium Dioxide MT 600 SAS®”, “Microtitanium Dioxide MT 500 SAS®” or “Microtitanium Dioxide MT 100 SAS®” from Tayca, - silica, alumina, aluminum stearate and treated with silicone, such as the product “STT-30-DS®” from the company Titan Kogyo, - silica and treated with a silicone, such as the product “UV-Titan X 195®” from the company Sachtleben Pigments, - alumina and treated with a silicone, such as the products "Tipaque TTO-55 (S)®" from the company Ishihara, or "UV Titan M 262®" from the company Sachtleben Pigments, - triethanolamine, such as the product "STT-65-S" from the company Titan Kogyo, - stearic acid, such as the product "Tipaque TTO-55 (C)®" from the company Ishihara, - sodium hexametaphosphate, such as the product "Microtitanium Dioxide MT 150 W®" from the company Tayca, - TiO2 treated with octyl trimethyl silane, sold under the trade name “T 805®” by the company Degussa Silices, - TiO2 treated with a polydimethylsiloxane, sold under the trade name “70250 Cardre UF TiO2SI3®” by the company Cardre, - anatase / rutile TiO2 treated with polydimethylhydrogensiloxane, sold under the trade name “Microtitanium Dioxide USP Grade Hydrophobie®” by the company Color Techniques, - TiO2 coated with triethylhexanoin, aluminum stearate, alumina, sold under the trade name Solaveil CT-200-LQ-(WD) from Croda, - TiO2 coated with aluminum stearate, alumina and silicone, sold under the trade name Solaveil CT-12W-LQ-(WD) from Croda, - TiO2 coated with lauroyl lysine, sold by Daito Kasei Kogyo under the name LL 5 Titanium Dioxide CR 50, - TiO2 coated with G,15 fluoroalcohol phosphate and aluminum hydroxide, sold by Daito Kasei Kogyo under the name PFX-5 TiO2 CR-50.
[0191] Mention may also be made of TiO2 pigments doped with at least one transition metal such as iron, zinc, manganese and more particularly manganese. Preferably, 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 additionally comprise one or more dispersing agents such as, for example, a sorbitan ester such as sorbitan isostearate, a polyoxyalkylenated fatty acid and glycerol ester such as TRLPPG3 Myristylether Citrate and Poly-glyceryl-3 Polyricinoleate. Preferably, the oily dispersion of titanium oxide particles comprises at least one dispersing agent chosen from polyoxyalkylenated fatty acid and glycerol esters.More particularly, mention may be made of the oily dispersion of manganese-doped TiO2 particles in capric / caprylic acid triglyceride in the presence of TRLPPG-3 Myristylether Citrate and Polyglyceryl-3 Polyricinoleate and Sorbitan Isostearate with the INCI name: Titanium Dioxide (and) TRLPPG-3 Myristylether Citrate (and) Polyglyceryl-3 Polyricinoleate (and) Sorbitan Isostearate, such as the product sold under the trade name Optisol TD50® by the company Croda.
[0192] Uncoated titanium oxide pigments are, for example, sold by the company . Tayca under the trade names “Microtitanium Dioxide MT 500 B” or “Microtitanium Dioxide MT600 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”.
[0193] Uncoated zinc oxide pigments are, for example: - those marketed under the name “Z-cote” by the company Sunsmart; - those marketed under the name “Nanox®” by the company Elementis; - those marketed under the name “Nanogard WCD 2025®” by the company Nanophase Technologies.
[0194] Coated zinc oxide pigments are for example: - those marketed under the name “Oxide zinc CS-5®” by the company Toshibi (ZnO coated with polymethylhydrogenesiloxane); - those marketed under the name “Nanogard Zinc Oxide FN®” by the company Nanophase Technologies (in 40% dispersion in Finsolv TN®, benzoate of C12-C15 alcohols); - those marketed under the name “Daitopersion Zn-30®” and “Daitopersion Zn-50®” by Daito (dispersions in cyclopolymethyl-siloxane / oxyethylenated polydimethylsiloxane, containing 30% or 50% of zinc oxides coated with silica and polymethylhydrogensiloxane); - those marketed under the name “NFD Ultrafine ZnO®” by the company Daikin (ZnO coated with perfluoroalkyl phosphate and perfluoroalkylethyl copolymer dispersed in cyclopentasiloxane); - those marketed under the name “SPD-Z1®” by the company Shin-Etsu (ZnO coated with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane); - those marketed under the name “Escalol Z100®” by the company ISP (alumina-treated ZnO dispersed in the mixture of ethylhexyl methoxycinnamate / PVP-hexadecene copolymer / methicone); - those marketed under the name “Fuji ZnO-SMS-10®” by the company Fuji Pigment (ZnO coated with silica and polymethylsilsesquioxane); - those marketed under the name “Nanox Gel TN®” by the company Elementis (ZnO dispersed at 55% in C12-C15 alcohol benzoate with hydroxystearic acid polycondensate).
[0195] Uncoated cerium oxide pigments may be, for example, those sold under the name “Colloidal Cerium Oxide®” by the company Rhône Poulenc.
[0196] Uncoated iron oxide pigments are for example sold by the company Arnaud under the names “Nanogard WCD 2002® (FE 45B®)”, “Nanogard Iron Fe 45 BL AQ”, “Nanogard Fe 45R AQ®”, “Nanogard WCD 2006® (FE 45R® )”, or by the company Mitsubishi under the name “TY-220®”.
[0197] Coated iron oxide pigments are for example sold by the company Arnaud under the names “Nanogard WCD 2008 (FE 45B FN)®”, “Nanogard WCD 2009® (FE 45B 556®)”, “Nanogard FE 45 BL 345®”, “Nanogard FE 45 BL®”, or by the company BASF under the name “Oxyde De Fer Transparent®”.
[0198] Mention may also be made of mixtures of metal oxides, in particular titanium dioxide and 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®”, as well as 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 glycerin such as the product “M 211®” sold by the company Sachtleben Pigments.
[0199] According to the invention, titanium oxide pigments, coated or uncoated, are particularly preferred.
[0200] According to a preferred embodiment, the composition comprises one or more lipophilic UV filters.
[0201] According to a preferred embodiment, the composition comprises one or more UV filters chosen from lipophilic UV-A filters and / or lipophilic UV-B filters.
[0202] More preferably, the composition comprises one or more UV filters chosen from dibenzoylmethane derivatives, salicylic derivatives, [3,[3'-diphenylacrylate derivatives, triazine derivatives and benzylidene camphor derivatives.
[0203] According to a particularly preferred embodiment, the composition comprises one or more UV filters chosen from Terephthalylidene dicamphor sulfonic acid, Butyl Methoxydibenzoylmethane, Homosalate, Ethylhexyl Salicylate, Octocrylene, Ethylhexyl triazone, and mixtures thereof.
[0204] According to one embodiment, the quantity of the organic UV filter(s) present in the composition according to the invention may range from 0.5% to 50% by weight, relative to the total weight of the composition. It ranges for example from 1% to 40% by weight, or for example from 5% to 35% by weight, and for example again ranges from 10% to 35% by weight, relative to the total weight of the composition.
[0205] According to a particular embodiment, the concentration of UV filters in the composition according to the invention ranges from 1% to 50%, preferably from 1% to 40% by weight relative to the total weight of the composition.
[0206] According to a particular embodiment, the composition according to the invention comprises at least one mineral UV filter.
[0207] According to a particular embodiment, the quantity of the mineral UV filter(s) present in the composition according to the invention may range from 0.01% to 20% by weight, relative to the total weight of the composition. It ranges, for example, from 1% to 15% by weight, relative to the total weight of the composition.
[0208] According to a particular embodiment, the composition according to the invention further comprises one or more organic UV filters and one or more mineral UV filters.
[0209] According to a particular embodiment, the composition according to the invention further comprises a combination of UV filters as described in patent FR 2 977 490, application WO 2013 / 004777 or application US 2014 / 0134120. Surfactants
[0210] According to a preferred embodiment, the composition according to the invention may further comprise at least one surfactant.
[0211] The surfactants may be chosen from non-surfactants ionic, anionic, cationic, amphoteric, and mixtures thereof. Reference may be made to the document "Encyclopedia of Chemical Technology, KIRK-OTHMER", volume 22, pp. 333-432, 3rd edition, 1979, WILEY, for the definition of the emulsifying properties and functions of surfactants, in particular pp. 347-377 of this reference, for anionic, amphoteric and nonionic surfactants. Nonionic surfactant
[0212] Preferably, the composition according to the invention comprises at least one non-ionic surfactant.
[0213] The non-ionic surfactants may be chosen in particular from alkyl- and polyalkyl-esters of poly(ethylene oxide), oxyalkylenated alcohols, alkyl- and polyalkyl-ethers of poly(ethylene oxide), alkyl- and polyalkyl-esters of sorbitan, polyoxyethylenated or not, alkyl- and polyalkyl-ethers of sorbitan, polyoxyethylenated or not, alkyl- and polyalkyl-glycosides or polyglycosides, in particular alkyl- and polyalkyl-glucosides or polyglucosides, alkyl- and polyalkyl-esters of sucrose, glycerol esters, alkyl- and polyalkyl-esters of glycerol, polyoxyethylenated or not, alkyl- and polyalkyl-ethers of glycerol, polyoxyethylenated or not, geminal surfactants, cetyl alcohol, stearyl alcohol, and mixtures thereof.
[0214] As glycerol esters, mention may in particular be made of C16-C22 fatty acid esters of glyceryl, in particular glyceryl esters of fatty acids having 18 carbon atoms, and polyglycerol esters of fatty acids containing from 8 to 12 carbon atoms.
[0215] As an ester of glyceryl and C[8] fatty acid, mention may in particular be made of glyceryl stearate (glyceryl mono-, di- and / or tristearate) (CTFA name: glyceryl stearate), glyceryl ricinoleate, or mixtures thereof.
[0216] As ester of glycerol and fatty acid, mention may be made of mixtures based on glyceryl stearate, such as the mixture of glyceryl stearate and polyethylene glycol monostearate 100 EO, and in particular that comprising a 50 / 50 mixture, marketed under the name Arlacel 165® by the company Croda, or the product containing Glyceryl stearate (glyceryl mono-distearate) and potassium stearate, marketed under the name Tegin® by the company Goldschmidt (CTFA name: glyceryl stearate SE).
[0217] Preferably, a composition according to the invention comprises at least one surfactant, in particular a non-ionic surfactant, and preferably a surfactant chosen from glycerol esters. Anionic surfactant
[0218] The anionic surfactants may be chosen from alkyl ether sulfates, carboxylates, amino acid derivatives, sulfonates, isethionates, taurates, sulfosuccinates, alkylsulfoacetates, phosphates and alkylphosphates, polypeptides, metal salts of C10-C25 fatty acids, in particular C16-C25, in particular metal stearates and behenates, alkali metal salts of cetylphosphate, and mixtures thereof.
[0219] As alkaline salts of cetylphosphate, mention may in particular be made of potassium cetylphosphate. In particular, use may be made of the monopotassium salt of monocetyl phosphate (INCI name: potassium cetyl phosphate) sold under the name “Amphisol K” by the company DSM Nutritional products. Cationic surfactant
[0220] The cationic surfactants may be chosen from alkylimidazolidiniums, such as isostearylethylimidonium ethosulfate, ammonium salts, such as (C|2-10 alkyl)-tri(C, 10 alkyl)ammonium halides such as N,N,N-trimethyl-l-docosanaminium (or Behentrimonium chloride). Amphoteric surfactant
[0221] The compositions according to the invention may also contain one or more amphoteric surfactants such as N-acyl-amino acids such as N-alkyl-aminoacetates and disodium cocoamphodiacetate, and amine oxides such as stearamine oxide, or even silicone surfactants such as dimethicone copolyol phosphates such as that sold under the name Pecosil PS 100® by the company Phoenix Chemical. Silicone surfactant
[0222] The composition may also comprise at least one silicone surfactant. By way of example, non-ionic surfactants with an HLB greater than or equal to 8 at 25°C, used alone or as a mixture, may be mentioned, dimethicone copolyol or dimethicone copolyol benzoate, and non-ionic surfactants with an HLB less than 8 at 25°C, used alone or as a mixture, the mixture of cyclomethicone / dimethicone copolyol.
[0223] Preferably, a composition according to the invention comprises less than 2% by weight of silicone surfactant(s), in particular less than 1% by weight of silicone surfactant(s), preferably less than 0.5% by weight of silicone surfactant(s), and more preferably is free of silicone surfactant(s).
[0224] The surfactant(s) may be present in a composition according to the invention, in a proportion ranging from 0.5% to 10% by weight, and preferably from 0.5% to 5% by weight, relative to the total weight of the composition. Gelling agent / Thickener
[0225] Depending on the fluidity of the composition that it is desired to obtain, one or more thickeners and / or gelling agents, in particular hydrophilic ones, i.e. soluble or dispersible in water, can be incorporated into the composition.
[0226] Examples of hydrophilic gelling agents that may be mentioned are modified or unmodified carboxyvinyl polymers, such as the products sold under the names Carbopol (CTFA name: carbomer) and Pemulen (CTFA name: Acrylates / C 10-30 akyl acrylate crosspolymer) by the company Goodrich, polyacrylamides, polymers and copolymers of 2-acrylamido 2-methylpropane sulfonic acid, optionally crosslinked and / or neutralized, such as poly(2-acrylamido 2-methylpropane sulfonic acid) sold by the company Hoechst under the name “Hostacerin AMPS” (CTFA name: Ammonium Polyacryldimethyltauramide), crosslinked anionic copolymers of acrylamide and AMPS, in the form of an E / O emulsion, such as those sold under the name Sepigel 305 (CTFA name: Polyacrylamide / C13-14 Isoparaffin / Laureth-7) and under the name Simulgel 600 (name CTFA: Acrylamide / Sodium acryloyldimethyltaurate copolymer / Isohexadecane / Polysorbate 80) by Seppic, polysaccharide biopolymers such as xanthan gum, guar gum, alginates, modified celluloses, and their mixtures. The amount of gelling agents depends on the desired purpose.
[0227] According to one embodiment, the quantity of gelling agents ranges for example from 0.01 to 10% and for example from 0.05 to 5% by weight, relative to the total weight of the composition. Fillers
[0228] According to a particular embodiment, a composition according to the invention may further comprise one or more fillers, in particular chosen from those conventionally used in care and / or makeup compositions.
[0229] For the purposes of the present invention, the term "fillers" is intended to denote colorless or white, solid particles of all forms, of mineral or organic nature, natural or synthetic, which are in an insoluble form and dispersed in the medium of the composition.
[0230] Of course, these fillers are used in appropriate contents and conditions so as not to be detrimental to the properties of the composition.
[0231] They make it possible to give the composition containing them softness, mattness and uniformity. In addition, these fillers advantageously make it possible to combat various aggressions such as sebum or sweat.
[0232] By way of illustration of these fillers, mention may be made of talc, mica, silica, kaolin, poly-[3-alanine and polyethylene powders, tetrafluoroethylene polymer powders (Teflon®), lauroyl-lysine, starch, boron nitride, hollow polymer microspheres such as those of polyvinylidene chloride / acrylonitrile such as Expancel® (Nobel Industrie), acrylic acid copolymers, silicone resin microbeads (Tospearls® from Toshiba, for example), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, magnesium carbonate and hydrocarbonate, hydroxyapatite, barium sulfate, aluminum oxides, polyurethane powders, composite fillers, hollow silica microspheres, and glass or silicon microcapsules. ceramic.Particles, which have the shape of portions of hollow spheres, as described in patent applications JP-2003 128 788 and JP-2000 191 789, may also be used. Coloring matters
[0233] A composition according to the invention may further comprise at least one particulate or non-particulate, water-soluble or non-water-soluble coloring matter, and preferably in an amount of at least 0.0001% by weight relative to the total weight of the composition.
[0234] For obvious reasons, this quantity is likely to vary significantly with regard to the intensity of the desired color effect and the color intensity provided. by the coloring materials considered and its adjustment clearly falls within the skills of a person skilled in the art.
[0235] As specified above, the coloring materials suitable for the invention can be water-soluble but also fat-soluble. Water-soluble dyes
[0236] For the purposes of the invention, the term "water-soluble coloring matter" means any generally organic, natural or synthetic compound, soluble in an aqueous phase or water-miscible solvents and capable of coloring.
[0237] As water-soluble dyes suitable for the invention, mention may in particular be made of synthetic or natural water-soluble dyes such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocyanin, black carrot, hibiscus, elderberry), caramel, riboflavin.
[0238] Water-soluble colorants are, for example, beetroot juice and caramel.
[0239] According to a preferred embodiment, the composition according to the invention comprises at least minus a water-soluble colorant.
[0240] The water-soluble dyes may be present in an amount of 0.0001% to 2% by weight, relative to the total weight of the composition containing them. Fat-soluble colorants
[0241] By "liposoluble coloring matter", within the meaning of the invention, is meant any generally organic, natural or synthetic compound, soluble in an oily phase or solvents miscible with a fatty substance and capable of coloring.
[0242] As liposoluble dyes suitable for the invention, mention may in particular be made of liposoluble dyes, synthetic or natural, such as, for example, DC Red 17, DC Red 21, DC Red 27, DC Green 6, DC Yellow 11, DC Violet 2, DC Orange 5, Sudan red, carotenes ([3-carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto, curcumin.
[0243] The particulate coloring materials may be present in an amount of 0.0001% to 10% by weight, relative to the total weight of the composition containing them.
[0244] These may in particular be pigments, nacres and / or particles with metallic reflections. Pigments
[0245] By “pigments” is meant white or colored particles, mineral or organic, insoluble in an aqueous solution, intended to color and / or opacify the composition containing them.
[0246] The pigments can be white or colored, mineral and / or organic.
[0247] As mineral pigments, mention may be made of oxides or dioxides of titanium, zirconium or cerium, as well as oxides of zinc, iron or chromium, ferric blue, manganese violet, ultramarine blue and chromium hydrate, and mixtures thereof.
[0248] It may also be a pigment having a structure which may be, for example, of the sericite / brown iron oxide / titanium dioxide / silica type. Such a pigment is marketed, for example, under the reference Coverleaf NS or JS by the company Chemicals And Catalysts and has a contrast ratio of around 30.
[0249] It may also be a question of pigments having a structure which may be, for example, of the silica microsphere type containing iron oxide. An example of a pigment having this structure is that marketed by the company Miyoshi under the reference PC Bail PC-LL-100 P, this pigment being made up of silica microspheres containing yellow iron oxide.
[0250] Advantageously, the pigments may be iron oxides and / or titanium dioxides.
[0251] According to a particular embodiment, a composition according to the invention comprises less than 1% by weight of pigments. Mother-of-pearl
[0252] By “mother-of-pearl” is meant colored particles of any shape, iridescent or not, notably produced by certain molluscs in their shell or synthesized, and which present a color effect by optical interference.
[0253] The nacres may be chosen from pearlescent pigments, such as titanium mica coated with iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye, as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles on the surface of which are superimposed at least two successive layers of metal oxides and / or organic coloring materials.
[0254] Examples of nacres that may also be mentioned include natural mica coated with titanium oxide, iron oxide, natural pigment or bismuth oxychloride.
[0255] Among the mother-of-pearls available on the market, we can cite the Timica, Flamenco and Duochrome mother-of-pearls (based on mica) marketed by the company Engelhard, the Timiron mother-of-pearls marketed by the company Merck, the Prestige mother-of-pearls based on mica marketed by the company Eckart and the Sunshine mother-of-pearls based on synthetic mica marketed by the company Sun Chemical.
[0256] The mother-of-pearls can more particularly have a yellow color or reflection, pink, red, bronze, orange, brown, gold and / or copper.
[0257] Advantageously, the nacres in accordance with the invention are micas covered with titanium dioxide or iron oxide as well as bismuth oxychloride.
[0258] According to a particular embodiment, a composition according to the invention comprises less than 1% by weight of nacres. Metallic sheen particles
[0259] By "metallic reflective particles", within the meaning of the present invention, is meant any compound whose nature, size, structure and surface condition allows it to reflect incident light, in particular in a non-iridescent manner.
[0260] The particles with a metallic sheen that can be used in the invention are in particular chosen from particles of at least one metal and / or at least one metal derivative; particles comprising a substrate, organic or mineral, single-material or multi-material, covered at least partially by at least one layer with a metallic sheen comprising at least one metal and / or at least one metal derivative; and mixtures of said particles.
[0261] Among the metals that may be present in said particles, mention may be made, for example, of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te, Se and their mixtures or alloys. Ag, Au, Cu, Al, Zn, Ni, Mo, Cr, and their mixtures or alloys (for example bronzes and brasses) are preferred metals.
[0262] By “metal derivatives” is meant compounds derived from metals, in particular oxides, fluorides, chlorides and sulfides.
[0263] By way of illustration of these particles, mention may be made of aluminum particles, such as those marketed under the names Starbrite 1200 EAC® by the company Siberline and Metalure® by the company Eckart and glass particles covered with a metallic layer, in particular those described in documents JP-A-09188830, JP-A-10158450, JP-A-10158541, JP-A-07258460 and JP-A-05017710.
[0264] According to a particular embodiment, a composition according to the invention comprises less than 1% by weight of particles with metallic reflections. Hydrophobic treatment of coloring materials
[0265] The powdery coloring materials as described above may be surface-treated, totally or partially, with a hydrophobic agent, to make them more compatible with the oily phase of the composition of the invention, in particular so that they have good wettability with oils. Thus, these treated pigments are well dispersed in the oily phase. Hydrophobic treated pigments are described in particular in document EP-A-1086683.
[0266] The hydrophobic treatment agent may be chosen from silicones such as methicones, dimethicones, perfluoroalkylsilanes; fatty acids such as stearic; metallic soaps such as aluminum dimyristate, aluminum salt of hydrogenated tallow glutamate; perfluoroalkyl phosphates; polyhexafluoropropylene oxides; perfluoropolyethers; amino acids; N-acylated amino acids or their salts; lecithin, isopropyl trisostearyl titanate, isostearyl sebacate, and mixtures thereof.
[0267] The term alkyl mentioned in the compounds cited above designates in particular an alkyl group having from 1 to 30 carbon atoms, preferably having from 5 to 16 carbon atoms. Additives
[0268] The composition in accordance with the present invention may further comprise conventional cosmetic adjuvants, in particular chosen from active ingredients, softeners, humectants, opacifiers, emollients, silicones, anti-foaming agents, perfumes, polar additives, preservatives, in particular phenoxyethanol, polymers, for example film-forming polymers, propellants, dispersing agents, anti-pollution agents, chelating agents, alkalizing or acidifying agents or any other ingredient usually used in the cosmetic and / or dermatological field.
[0269] Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
[0270] Among the alkalizing agents, mention may be made, by way of example, of ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides.
[0271] Preferably, the cosmetic composition comprises one or more alkalizing agents chosen from alkanolamines, in particular triethanolamine, and sodium hydroxide.
[0272] In the case of a direct emulsion, the pH of the composition in accordance with the invention is generally between approximately 3 and 12, preferably between approximately 5 and 11, and even more particularly from 5.5 to 8.
[0273] Among the active agents for the care of keratin materials such as the skin, lips, scalp, hair, eyelashes or nails, mention may be made, for example, of vitamins and their derivatives or precursors, alone or in mixtures; anti-oxidant agents; anti-free radical agents; anti-pollutant agents; self-tanning agents; anti-glycation agents; soothing agents; deodorant agents; essential oils; NO-synthase inhibitors; agents stimulating the synthesis of dermal or epidermal macromolecules and / or preventing their degradation; agents stimulating the proliferation of fibroblasts; agents stimulating the proliferation of keratinocytes; muscle relaxants; cooling agents; tightening agents; matting agents; depigmenting agents; pro-pigmenting agents; keratolytic agents; desquamating agents; moisturizing agents; anti-inflammatory agents; antimicrobial agents; slimming agents; agents acting on the energy metabolism of cells; insect repellents; substance P or CRGP antagonists; anti-hair loss agents; anti-wrinkle agents; anti-aging agents.
[0274] A person skilled in the art will choose the said active ingredient(s) according to the desired effect on the skin, hair, eyelashes, eyebrows, nails.
[0275] Of course, a person skilled in the art will take care to choose this or these possible additional compounds and / or their quantity in such a way that the advantageous properties of a composition according to the invention are not, or not substantially, altered by the envisaged addition. Composition
[0276] A composition according to the invention may be in the form of an emulsion, for example an oil-in-water (O / W) or water-in-oil (W / O) emulsion, a gel, for example an oil-in-water or water-in-oil emulsified gel, an aqueous composition, or even in the form of a gel / gel type composition.
[0277] According to one embodiment, the composition according to the present invention is an emulsion.
[0278] According to one variant, the composition according to the invention is a simple emulsion.
[0279] According to one variant, the composition according to the invention is a multiple emulsion. It may be a triple emulsion.
[0280] According to one variant, the composition according to the invention is a direct simple emulsion. Thus, according to one embodiment, the composition according to the present invention is an oil-in-water (O / W) emulsion.
[0281] According to one variant, the composition according to the invention is a simple inverse emulsion. Thus, according to one embodiment, the composition according to the present invention is a water-in-oil (W / O) emulsion.
[0282] According to one variant, the composition according to the invention is an aqueous formulation of the aqueous solution or gel type.
[0283] Preferably, the composition is an emulsion, in particular a water-in-oil or oil-in-water emulsion.
[0284] In the case of compositions in the form of oil-in-water or water-in-oil emulsions, the emulsification processes that can be used are of the blade or propeller, rotor-stator and HHP type.
[0285] To obtain stable emulsions with a low polymer content (oil / polymer ratio >25), it is possible to make the dispersion in concentrated phase then dilute dispersion with the rest of the aqueous phase.
[0286] It is also possible, by HHP (between 50 and 800 bars), to obtain stable dispersions with drop sizes that can go down to 100 nm.
[0287] The composition according to the invention may be more or less fluid and have the appearance of a white or colored cream, an ointment, a milk, a lotion, a serum, a paste or a mousse. It may optionally be applied to the skin in the form of an aerosol. It may also be in solid form, for example in the form of a stick.
[0288] A composition according to the invention may be in the form of a cosmetic composition for the care and / or makeup of keratin materials, preferably a cosmetic composition for the care of keratin materials, in particular of the body or the face, preferably of the face.
[0289] The compositions according to the invention find their application in a large number of treatments, in particular cosmetic treatments, of the skin, lips and hair, including the scalp, in particular for the protection and / or care of the skin, lips and / or hair, and / or for making up the skin and / or lips.
[0290] Another object of the present invention consists of the use of the compositions according to the invention as defined above for the manufacture of products for the cosmetic treatment of the skin, lips, nails, hair, eyelashes, eyebrows and / or scalp, in particular care products, sun protection products and makeup products.
[0291] The compositions according to the invention may be in the form of skin or semi-mucous membrane care products, such as a protective composition, cosmetic care for the face, for the lips, for the hands, for the feet, for anatomical folds or for the body (for example day creams, night cream, day serum, night serum, make-up remover cream, make-up base, anti-sun composition, protective or care body milk, after-sun milk, lotion, gel or mousse for skin or scalp care, serum, mask or after-shave composition).
[0292] The cosmetic compositions according to the invention can, for example, be used as a care and / or sun protection product for the face and / or body of liquid to semi-liquid consistency, such as lotions, milks, more or less creamy creams, gels, gel-creams. They can optionally be packaged as an aerosol and be in the form of a mousse or spray.
[0293] The compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or 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 include non-aerosol pumps or "atomizers", aerosol containers comprising a propellant as well as aerosol pumps using compressed air as a propellant. These are described in US patents 4,077,441 and 4,850,517.
[0294] The compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants such as, for example, hydrofluorinated compounds dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane, trichlorofluoromethane. They are preferably present in amounts ranging from 15 to 50% by weight relative to the total weight of the composition.
[0295] The composition may be applied to the skin by hand or using an applicator.
[0296] According to another aspect, the invention also relates to a cosmetic assembly comprising: (i) a container delimiting one or more compartments (d), said container being closed by a closing element and possibly being non-watertight; and ii) a makeup and / or care composition in accordance with the invention placed inside said compartment(s).
[0297] The container may for example be in the form of a pot or a box.
[0298] The closing element may be in the form of a cover comprising a mounted hood movable by translation or by pivoting relative to the container housing said makeup and / or care composition(s).
[0299] Such compositions are in particular prepared according to the general knowledge of those skilled in the art.
[0300] Such compositions as defined above can in particular be used for cosmetic use according to the invention.
[0301] Thus, the invention also relates to the use of a composition according to the invention for the care and / or makeup of keratin materials, preferably for the care, in particular of the skin of the body and / or face.
[0302] The invention also relates to a cosmetic process for making up and / or caring for keratin materials, in particular the skin, comprising at least one step of applying to said keratin materials a composition as defined above.
[0303] Preferably, the invention also relates to a cosmetic process for caring for keratin materials, in particular for the body and / or face, comprising at least one step of applying to said keratin materials a composition as defined above.
[0304] Cosmetic processes for making up and / or caring for keratin materials, in particular the skin, are non-therapeutic.
[0305] In particular, the present invention relates to the cosmetic, non-therapeutic use of a composition as described above for the protection of keratin materials, in particular the skin and / or the lips and / or the hair. against solar radiation.
[0306] The invention also relates to the cosmetic, non-therapeutic use of a composition as defined above for combating or preventing the signs of photo-induced premature aging of keratin materials, in particular of the skin and / or lips and / or hair.
[0307] According to one embodiment, the invention also relates to the use of a composition according to the invention for reducing pigmentation induced by UVB, UVA and long UVA rays.
[0308] The present invention also relates to the cosmetic use of a composition as defined above for preventing darkening of the skin, and / or improving the color and / or uniformity of the complexion.
[0309] Furthermore, the present invention relates to the cosmetic use of a composition as defined above for preventing premature aging of keratin materials, in particular of the skin, in particular on the face, décolleté, arms, hands and / or shoulders, in particular the signs of skin aging of actinic origin such as photoaging.
[0310] The present invention also relates to the cosmetic use of a composition as defined above for preventing a loss of firmness and / or elasticity and / or tone and / or suppleness of the skin, the formation of wrinkles and fine lines, a dull appearance of the complexion, and / or a papery appearance of the skin.
[0311] The present invention also relates to a non-therapeutic cosmetic process for the protection of keratin materials, in particular the skin and / or lips and / or hair against solar radiation, comprising the application to the surface of the keratin material of at least one composition according to the invention.
[0312] It also relates to a non-therapeutic cosmetic process for preventing and / or treating the signs of aging of a keratin material comprising the application to the surface of the keratin material of at least one composition according to the invention.
[0313] For the purposes of the present invention, “preventing” means reducing, at least in part, the risk of a given phenomenon occurring.
[0314] Throughout the description, including the claims, the expression "comprising a" must be understood as being synonymous with "comprising at least one", unless otherwise specified.
[0315] The expressions “between ... and ...”, “includes from ... to ...”, “formed from ... to ...”, and “ranging from ... to ...” must be understood inclusively, unless otherwise specified.
[0316] In the description and examples, unless otherwise indicated, the percentages are percentages by weight. The percentages are therefore expressed by weight per
[0317]
[0318]
[0319]
[0320]
[0321]
[0322]
[0323]
[0324]
[0325]
[0326] relative to the total weight of the composition. Temperature is expressed in degrees Celsius unless otherwise stated, and pressure is atmospheric pressure unless otherwise stated. The invention is illustrated in more detail by the non-limiting examples presented below. Examples Example A: Preparation of merocyanines according to the invention Example A1: Preparation of compound (A) (HAS) 122.23 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 75.45 grams of ethyl cyanoacetate in approximately equimolar proportions in the presence of a base and optionally a solvent. The following base / solvent combinations were used: [Tables 2] Example Base Solvent Example ALI DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A 1.2 Triethylamine isopropanol Example A 1.3 3-Methoxypropylamine isopropanol Example A 1.4 3-Methoxypropylamine tert-amylalcohol Example A 1.5 3-Methoxypropylamine toluene Example A 1.6 3-Methoxypropylamine dimethylformamide Example A 1.7 3-Methoxypropylamine solvent-free Example A 1.8 N-Morpholine isopropanol The completion of the alkylation reaction could be monitored, for example, by methods such as TLC, GC, or HPLC. 162.30 grams of compound (14) were obtained as a brown oil. After crystallization, the product was obtained as yellowish crystals. Melting point: 92.7°C. Example A2: Preparation of compound (B)
[0327] (B)
[0328] 101.00 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 86.00 grams of 2-cyano-N-(3-methoxy-propyl)-acetamide in approximately equimolar proportions in the presence of a base and optionally a solvent.
[0329] The following base / solvent combinations were used:
[0330] [Tables3] Example Base Solvent Example A2.1 DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A2.2 Triethylamine isopropanol Example A2.3 3-methoxypropylamine isopropanol Example A2.4 3-methoxypropylamine tert-amylalcohol Example A2.5 3-methoxypropylamine toluene Example A2.6 3-methoxypropylamine dimethylformamide Example A2.7 3-methoxypropylamine solvent-free
[0331] The crude product (B) was obtained in the form of a dark brown oil. After column chromatography on silica gel (eluent: toluene / methanol 99 / 1), 81.8 grams of product were obtained in the form of yellowish crystals.
[0332] Melting point: 84.7-85.3°C.
[0333] Example A3: Preparation of compound (D) (D) 14 £ „,o ] N
[0335] 13.09 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 10.12 grams of isobutyl cyanoacetate in the presence of a base and optionally a solvent.
[0336] The following base / solvent combinations were used: Example Base Solvent Example A3.1 DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A3.2 Triethylamine isopropanol Example A3.3 3-Methoxypropylamine isopropanol Example A3.4 N-Methylmorpholine tert-amylalcohol Example A3.5 3-Methoxypropylamine toluene Example A3.6 3-Methoxypropylamine dimethylformamide Example A3.7 3-Methoxypropylamine solvent-free
[0338]
[0339]
[0340]
[0341]
[0342]
[0343] 15.97 grams of crude product (27) were obtained as a dark brown oil. After column chromatography on silica gel (eluent: toluene / acetone), 13.46 grams of product were obtained as yellowish crystals. Melting point: 96.3°C. Example A4: Preparation of compound (C) (C) H > ] " r 4 148.4 grams of 3-[(3-methoxypropyl)amino]-2-cyclohexen-1-one were alkylated with dimethyl sulfate or alternatively with diethyl sulfate and treated with 130.00 grams of 2-ethoxyethyl cyanoacetate in the presence of an organic base and a solvent. The following base / solvent combinations were used: Example Base Solvent Example A4.1 DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) dimethylacetamide Example A4.2 Triethylamine isopropanol Example A4.3 3-Methoxypropylamine isopropanol Example A4.4 N-methylmorpholine tert-amylalcohol Example A4.5 3-Methoxypropylamine toluene Example A4.6 3-Methoxypropylamine dimethylformamide Example A4.7 3-Methoxypropylamine solvent-free
[0345] Example 1: Solubilization tests of Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate (C) prepared in Example A4 in saturated simplex solutions
[0346] Simplex solutions comprising the filter Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate in excess in different solvents and solvent mixtures are prepared from the weight proportions as detailed in the table below. The values are expressed as a percentage by weight, relative to the total weight of the composition.
[0347] [Tableauxô] Compounds Formula 1 Not of the invention Formula 2 Invention Formula 3 Invention Formula 4 Invention Formula 5 Invention Water 95.24 90.48 93.33 85.72 77.14 Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate (according to Example A) 4.76 4.76 4.76 4.76 4.76 Nicotinamide (DSM Nutritional Products) 4.76 4.76 4.76 Caffeine (BASF) 1.91 4.76 4.76 Dipropylene Glycol (DOW) 8.58
[0348] The filter Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate is assayed to calculate its solubility in different solvents and solvent mixtures. In each of the formulas, the filter is present at 5% excess in order to perform comparative saturation solubility measurements.
[0349] The solutions are filtered through 0.2 µm before dosing. The dosage is carried out 72 hours after preparation of the compositions, at room temperature.
[0350] For formula 4, an additional dosage was carried out 2 months after the preparation of the composition, at room temperature.
[0351] The assay is carried out by HPLC / UV under the following conditions: Acquity UPLC chain, BEH Shield RP 18 1.7 pm column (2.1 x 100 mm) from Waters, eluent gradient elution methanol / acidified water H3PO4 0.1%. The sample is prepared by dilution in methanol.
[0352] The results are detailed in the table below.
[0353] [Tables?] Formula 1 Outside the invention Formula 2 Invention Formula 3 Invention Formula 4 Invention Formula 5 Invention 72 hours at room temperature 0.056% 0.34% 0.26% 0.99% 1.38% 2 months at room temperature / / / 0.91% /
[0354] Solubility measurements show that the aqueous solubility of the filter Methoxypro-pylamino Cyclohexenylidene Ethoxyethylcyanoacetate (C) is increased in the compositions according to the invention which comprise nicotinamide and / or caffeine, compared to formula 1 which does not comprise a hydrotrope.
[0355] This solubility is verified over time because it remains stable two months after preparation of the composition, as demonstrated by the measurement carried out on composition 4 according to the invention.
[0356] The solubility in aqueous medium of compound (C) was also verified in the joint presence of a single hydrotrope and one or more organic solvents, the nature and weight proportions of which are detailed in Table 5 below. The values are expressed as a percentage by weight, relative to the total weight of the composition.
[0357] Formulations IA to G were prepared according to the following procedure:
[0358] - Solubilize compound 25 in propylene carbonate by heating to 65°C until obtain a clear mixture.
[0359] - Leave to cool to approximately 45°C then add the other ingredients in ending with the addition of ethanol.
[0360] - Heat the mixture again to 65°C.
[0361] - In the case where hydrotropes have been added (examples 2, 3, 5, 6 and 7), add a vortex until you get a clear mixture.
[0362] - Leave at 65°C for 1 hour then return to room temperature for 24 hours.
[0363] - Centrifuge the mixture at 4000 rpm for 10 min to accelerate the drying phase separation.
[0364] - The mixture is then stored at room temperature and the phase separation is observed after 2 weeks.
[0365] [Tables8] Ingredients Formula A Outside the invention Formula B Invention Formula C Invention Compound (C) 3 3 3 Propylene carbonate 19.4 14.55 14.55 Nicotinamide 0 4.85 0 Sodium salicylate 0 0 4.85 Water 38.8 38.8 38.8 Miglyol 810 38.8 38.8 38.8 Number of aqueous phases 2 1 1
[0366] [Tables9] Ingredients Formula D Outside the invention Formula E Invention Formula F Invention Formula G Invention Compound (C) 3 3 3 3 Propylene carbonate (Merck) 12.125 12.125 12.125 12.125 Ethanol (Sigma Aldrich) 7.275 4.85 4.85 4.85 Nicotinamide (ThermoFisher GmbH) 2.425 Sodium salicylate (Sigma Aldrich) 2.425 Caffeine (Aliacura) 2.425 Water 38.8 38.8 38.8 38.8 Miglyol 810 (Sasol) 38.8 38.8 38.8 38.8 Number of aqueous phases 2 1 1 1
[0367] It is found that the lack of solubility of compound (C) either in water (Formula A) or in an aqueous mixture containing at least one organic solvent (Formula D) is overcome by the presence of a hydrotrope such as nicotinamide or sodium salicylate or caffeine. Example 2: Composition 6 according to the invention
[0368] Composition 6 according to the invention in gel form is prepared from the weight proportions as detailed in the table below. The values are expressed as a percentage by weight, relative to the total weight of the composition.
[0369] [TableauxlO] Phase Compounds (INCI) Formula 6 Invention A Water 76.4 Dipropylene Glycol (Dow) 10 Niacinamide ((DSM Nutritional Products) 5 Caffeine (BASF) 5 Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate (according to Example A) 1.3 B Phenoxyethanol (Toho Chemicals) 0.7 Caprylyl Glycol (Kolon Life Science) 0.2 Cl Carbomer (Acrypol 980 from Corel Pharma Chem) 0.3 Xanthan Gum (CP Kelco) 0.1 C2 Sodium Hydroxide (PT. Mulia Agung Chemindo) 0 D Water 1
[0370] The composition is prepared according to the following procedure: In a Rayneri-type under-flask beaker, the water from phase A, dipropylene glycol and niacinamide are mixed. When the solution is clear, caffeine is introduced, then Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate is introduced, leaving it stirred and heated to 40 °C. Once the solution is clear, the preservatives are added, then the gelling agents are introduced, and the composition is left to swell. The pH is then measured, and the composition is neutralized with NaOH to obtain a pH equal to 6. The water from phase D is then added.
[0371] The composition obtained is advantageously single-phase. Example 3: Compositions 7 and 8 according to the invention
[0372] Compositions 7 and 8 according to the invention in the form of oil-in-water emulsions are prepared from the weight proportions as detailed in the table below. The values are expressed as a percentage by weight, relative to the weight total composition.
[0373] [Tableauxll] Phase Composés (INCI) Formule 7 Invention A Sucrose Tristearate (Ryoto Sugar Ester S270 de Mitsubishi-Kagaku Foods) 1,08 PEG-40 Stéarate (Tego Acid S40 P MB de Evonik Goldschmidt) 1,57 Glyceryl Stéarate (DUB GMS / MB de Stearinerie Dubois) 2 C15.19 Alkane (Emogreen L19 de Seppic) 7,9 B1 Water 59,65 Dipropylene Glycol (Dow) 8 Niacinamide ((DSM Nutritional Products) 4 Caffeine (BASF) 4 Methoxypropylamino Cyclohexenylidene Ethoxyethyl-cyanoacetate (selon l’Example A) 1 Trisodium Ethylènediamine Disuccinate (Natrlquest E30 de Innospec Active Chemicals) 0,25 Hydroxyacetophenone (Symsave H O de Symrise) 0,5 Pentylene Glycol (A-Leen 5 de Mina solve) 3 B2 Sodium Hyaluronate (Cristalhyal LO de Soliance (Givaudan)) 0,5 Sodium Polyacrylate (Cosmedia SP de BASF) 0,5 B3 Gemini Surfactant (Asahi Kasei) 0,35 C Isododecane (Ineos) 1,7 Ammonium Polyacryloyldimethyl Taurate (Hostacerin AMPS de Clariant) 1,5 E Lauroyl Lysine (Ajinomoto) 2 Boron Nitride 0,5
[0374] Composition 7 is prepared according to the following procedure: The components of phase B1 are mixed and homogenized for 10 minutes at 70°C in a Rayneri-type under-blade emulsifier. The components of phase A at 60 °C are added for emulsification, the composition is left to stir for 10 minutes. The components of phases B2, B3 and C are added at 40 °C for gelation. The composition is left to stir for 15 minutes. The composition is cooled to 30 °C. The fillers of phase E are incorporated and the composition is left to stir for 15 minutes.
[0375] [Tablesl2] Phase Compounds (INCI) Formula 8 Invention A Niacinamide ((DSM Nutritional Products) 4 Dipropylene Glycol (Dow) 8 Phenoxyethanol (Toho Chemicals) 0.4 Water 66.6 Caffeine (BASF) 4 Trisodium Ethylenediamine Disuccinate (Natrlquest E30 from Innospec Active Chemicals) 0.2 Methoxypropylamino Cyclohexenylidene Ethoxyethylcya-noacetate (according to Example A) 1 B1 Glyceryl Stearate (and) PEG-100 Stearate (Tego Care 180 MB from Evonik Goldschmidt) 2.5 Cetyl Alcohol (Lanette 16 from BASF) 2 Caprylyl Glycol (Kolon Life Science) 0.3 Squalane (Neossance Squalane from Amyris) 6 B2 Tocopheryl Acetate (DL Alpha Tocopheryl Acetate from DSM Nutritional Products) 0.5 C
[0376] Composition 8 is prepared according to the following procedure
[0377] In a Rayneri-type beaker under a blade, water, dipropylene glycol, phenoxyethanol and niacinamide are mixed. When the solution is clear, the Caffeine is introduced, then Methoxypropylamino Cyclohexenylidene Ethoxyethyl-cyanoacetate is introduced, leaving it stirred and heated to 40 °C. Once the solution is clear, the compounds of phase B1 previously melted at 55 °C are added for emulsification, then the components of phase B2. The components of phase C are introduced, then the components of phase D, and the composition is left to swell.
[0378] Compositions 7 and 8 are both monophasic. In other words, compound (C) is formulated in the solute state. Example 4: Composition 9
[0379] Composition 9 is prepared from the weight proportions as detailed in the table below. The values are expressed as a percentage by weight, relative to the total weight of the composition.
[0380] [Tablesl3] Phase Al Compounds (INCI) Formula 9 Invention Water 20 Terephthalylidene dicamphor sulfonic acid (Mexoryl SX from Noveal) 0.9 Triethanolamine 0.35 Nicotinamide (ThermoFisher) 2.5 Sodium salycilate (Sigma Aldrich) 0.5 A2 Xanthan gum 0.1 Glycerin 6 Dipropylene glycol (CABB Group GmbH) 5 Acrylates / c 10-30 alkyl acrylate crosspolymer (Pemulen TR-1 Polymer from Lubrizol) 0.25 Water 22 B1 Stearic acid 1.5 Glyceryl stearate (and) peg-100 stearate (Arlacel 165-FP-PA-(SG) from Croda) 1.3 Homosalate 6 Butyl methoxydibenzoylmethane (Parsol 1789 from DSM Nu-trotional Products) 4 Ethylhexyl triazone (Uvinul T150 from BASF) 1,8 Ethylhexyl salicylate (Parsol EHS from DSM Nutritional Products) 5 Isopropyl palmitate (BASF) 7 Diisopropyl sebacate (Dub Dis from Stearinerie Dubois) 1 Caprylyl glycol 0.4 B2 Potassium cetyl phosphate (Amphisol K from DSM Nutritional Products) 1 pH adjuster QS pH 6.3 Cl Propylene carbonate (Merck) 6 Compound C 3 C2 Ethanol 4
[0381] Operating mode:
[0382] - Phases Al, B1 and C are prepared separately by mixing the ingredients which make up each phase, by heating to 65°C with magnetic stirring, until a clear mixture is obtained.
[0383] - The ingredients of phase B2 are introduced with stirring into phase B1 until a fine dispersion of potassium cetyl phosphate is obtained.
[0384] - Phase A2 is prepared by dispersing the gelling agents in the glycols, before add the water and mix with an Ultraturrax at 27000 rpm for 5 min.
[0385] - Phase C is prepared by introducing compound 25 into propylene carbonate with mechanical stirring and heating to 65°C until a clear mixture is obtained. The ethanol is then incorporated once the mixture has returned to room temperature.
[0386] - Phases Al and A2 are introduced into phase B1+B2 by mixing with Ultraturrax at 27000 rpm for 5 min to obtain an emulsion. Phase C is then incorporated by mixing with Ultraturrax at 27000 rpm for 5 min.
[0387] Composition 9 is advantageously an emulsion.
Claims
1. Claims Cosmetic or dermatological composition, in particular for makeup and / or care of keratin materials, comprising at least one aqueous phase, and: - at least one merocyanine of the following formula (I), as well as its geometric isomeric forms E / E- or E / Z-:
2. in which: - A is -O- or -NH; - R is a C1-C22 alkyl group, a C2-C22 alkenyl group, a C2-C22 alkynyl group, a C3-C22 cycloalkyl group or a C3-C22 cycloalkenyl group, said groups possibly being interrupted by one or more O; and - at least one hydrotrope selected from nicotinamide, caffeine, salts of salicylic acid, sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), sodium butyl monoglycolsulfate (NaBMGS), 4-aminobenzoic acid HCl, sodium cumenesulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof. Composition according to the preceding claim, comprising at least as merocyanine of formula (I), at least one compound chosen from the following compounds as well as their geometric isomeric forms E / E-, E / Z-: AH sure! ethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene}ethanoate B Ê H ...0 0^ .. N v T ] (2Z)-2-cyano-N-(3-methoxypropyl)-2-{3-[(3-methoxypropyl)amino]cyclohex-2-en-l-ylide ne}ethanamide CC>CL ^^--x H î ' G JX / \ xxx^x 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene}ethanoate D x..A Jx 1 H î KXxXxXXx r ï 2-methylpropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-l-ylidene}ethanoate E Ox Qx ^Ov xx ,xx xx H § xvyS | | N 2-butoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en-l-ylidene}ethanoate FH 1 A xx«A. . j 3-methoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene}ethanoate G CL CK XL H 1 r 3-ethoxypropyl (2Z)-cyano{3-[(3-methoxypropyl)amino]cycl ohex-2-en- l-ylidene}ethanoate
3. Composition according to any one of the preceding claims, in which the merocyanine of formula (I) is the compound 2-ethoxyethyl (2Z)-cyano{3-[(3-methoxypropyl)-amino]cyclohex-2-en-l-ylidene}etha noate (C) in its geometric E / Z configuration of the following structure: and / or its geometric configuration E / E of the following structure:
4.
5.
6. Composition according to any one of the preceding claims, the content of merocyanine(s) of formula (I) varying from 0.1% to 25% by weight, preferably from 0.2% to 20% by weight, more preferably from 0.5% to 10% by weight, and even better from 1% to 5% by weight, relative to the total weight of the composition. Composition according to any one of the preceding claims, comprising at least one hydrotrope chosen from nicotinamide, caffeine, and mixtures thereof. Composition according to the preceding claim, comprising at least one additional hydrotrope chosen from salts of salicylic acid, the sodium salt of pyroglutamic acid (sodium PCA), sodium 1,3-benzenedisulfonate, sodium benzoate, sodium 4-pyridinecarboxylate, sodium benzenesulfonate, sodium p-toluenesulfonate (NaPTS), butyl monoglycol sulfate sodium (NaBMGS), 4-aminobenzoic acid HCl, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, pyrogallol, N-picolylacetamide, procaine HCl, proline HCl, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylene sulfonate (SXS), ethyl carbamate, pyridoxal hydrochloride, sodium benzoate, N,N-dimethylacetamide, N-methylacetamide, isoniazid, and mixtures thereof and preferably at least one salt of salicylic acid.
7. Composition according to any one of the preceding claims, comprising at least nicotinamide, as hydrotrope.
8. Composition according to any one of the preceding claims, the content of hydrotrope(s) of which varies from 0.1% to 20% by weight, in particular from 0.1% to 10% by weight, preferably from 0.5% to 10% by weight, in particular from 0.5% to 3% by weight relative to the total weight of the composition.
9. Composition according to any one of the preceding claims, the mass ratio of merocyanine(s) of formula (I) / hydrotrope(s) varies from 0.01 to 8, preferably from 0.02 to 5, in particular from 0.05 to 3, and more preferably from 0.1 to 1.
5.
10. Composition according to any one of the preceding claims, comprising at least two distinct hydrotropes chosen from nicotinamide, caffeine, and sodium salicylate, and the mass ratio me-rocyanine(s) of formula (I) / hydrotropes ranging from 0.01 to 5, preferably from 0.02 to 3, in particular from 0.05 to 2, and more preferably from 0.1 to 1.
5.
11. Composition according to any one of the preceding claims, comprising two distinct hydrotropes chosen from nicotinamide and caffeine and the mass ratio between these two hydrotropes varying from 0.2 to 5, in particular from 0.5 to 3, and more preferably from 0.8 to 1.
2.
12. Composition according to any one of the preceding claims, comprising at least one alcohol, in particular a mono-alcohol, and preferably ethanol.
13. Composition according to any one of the preceding claims further comprising at least one alkylene carbonate and preferably propylene carbonate.
14. Composition according to any one of the preceding claims, comprising at least one polyol, in particular chosen from ethylene glycol, pentaerythritol, trimethylolpropane, pentylene glycol, propylene glycol, dipropylene glycol (DPG), caprylyl glycol, glycerol, polyglycerols, polyethylene glycols (PEG), and mixtures thereof, in particular chosen from propylene glycol, pentylene glycol, dipropylene glycol, and mixtures thereof, preferably is dipropylene glycol.
15. Composition according to any one of the preceding claims, comprising at least one fatty phase, preferably varying from 0.5% to 80% by weight, preferably from 1% to 40% by weight, and more preferably from 3% to 20% by weight relative to the total weight of the composition.
16. Composition according to any one of the preceding claims, further comprising at least one complementary UV filter distinct from the merocyanines of formula (I).
17. Composition according to any one of the preceding claims, characterized in that it is a cosmetic composition for the care of keratin materials, in particular of the body or the face, preferably of the face.
18. Cosmetic process for caring for keratin materials, in particular for the body and / or face, comprising at least one step of applying to said keratin materials a composition as defined according to any one of the preceding claims.