Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
  • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/85—Polyesters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
  • A61K2800/30—Characterized by the absence of a particular group of ingredients
  • A61K2800/31—Anhydrous
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
  • A61Q1/02—Preparations containing skin colorants, e.g. pigments
  • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
  • A61Q1/06—Lipsticks

Definitions

• the present invention relates to a photoprotective composition containing, in a physiologically acceptable medium, a karanja oil and at least one polyester resulting from the reaction between (i) a C20-C44 carboxylic acid dimer, (ii) at least one polyol and (iii) optionally at least one C8-C32 monoalcohol and/or at least one C 8 -C 3 6 monocarboxylic acid. It also relates to the use of this composition for preventing skin and/or hair damage caused by UV radiation. Finally, it relates to a mixture consisting of karanja oil and of the abovementioned polyester, intended for the production of a photoprotective composition.
• Karanja is a leguminous plant which originates from Asia. Karanja oil, which is extracted from the seeds, is used, in the Ayurvedic pharmacopea, for skin and haircare, in particular for its antiseptic and antiparasitic properties, and also in the treatment of eczema, psoriasis and scalp diseases. It is also used as an insecticide.
• karanja oil is indicated in application FR 2 762 008, in particular its use in moisturizing or antiwrinkle creams. It is thus found in the composition of various cosmetic products on the market, including antisun products.
• the inventors have discovered, unexpectedly, that the combination of karanja oil with a particular polyester makes it possible to increase the SPF or sun protection factor of compositions containing this oil. They have demonstrated that it is thus possible to formulate a photoprotect ive composition based on karanja oil which has an SPF of greater than 30, including anhydrous formulations of suntan oil type which are particularly desired owing to their easy and pleasant application on the skin and their water resistance, but which do not generally make it possible to achieve SPFs of greater than 20.
• the subject of the present invention is thus a photoprotect ive composition containing, in a physiologically acceptable medium, a karanja oil and at least one polyester resulting from the reaction between (i) a C 20 -C44 carboxylic acid dimer, (ii) at least one polyol and (iii) optionally at least one C 8 -C 32 monoalcohol and/or at least one C8-C36 monocarboxylic acid .
• the subject of the present invention is also a mixture consisting of karanja oil and of the abovement ioned polyester, and also the use thereof for producing a photoprotect ive composition.
• composition according to the invention makes it possibler to confer on the skin good protection against UV rays, in particular to obtain an SPF of at least 20, better still of at least 30, or even of at least 50, including effective protection against UVA rays, by means of cosmetic ingredients which can be at least 90% by weight of plant origin. It also advantageously exhibits good persistence with respect to water, a transparent or translucent appearance, an emollient nature and a gliding feel without being tacky.
• karanja oil is intended to mean a water-insoluble fraction, extracted from karanja seeds, which contains predominantly fatty acid triglycerides. Usually, it also contains free fatty acids in amounts such that the acidity of the oil (expressed in grams of free oleic acid per 100 g of oil) is between 5% and 10% and generally from 0.5% to 4% by weight of unsaponifiable substances, such as karanjin and pongamol which are furanoflavones .
• Karanja oil contains essentially oleic and linoleic acid triglycerides and, in smaller amounts, palmitic acid, stearic acid, linolenic acid, arachidic acid and behenic acid.
• This oil can be obtained by cold pressing of karanja seeds, according to processes well known to those skilled in the art and conventionally implemented for obtaining other plant oils. It is used as it is after deodorization according to a steam treatment process under vacuum and under nitrogen (such as that described in document FR 2 762 008), without subjecting it to one or more extractions using polar and/or nonpolar organic solvents.
• the karanja oil used according to the invention thus differs from alcoholic and aqueous-alcoholic extracts of karanja seeds.
• karanja is intended to mean in this description the plant also known under the following botanical names: Pongamia pinnata, Pongamia glabra, Millettia pinnata, Derris indica and Gadelupa pinnata .
• the composition according to the invention may, for example, contain from 1% to 60% by weight, preferably from 5% to 50% by weight and better still from 15% to 30% by weight of karanja oil, relative to the total weight of the composition.
• the mixture used for the production of this composition may, for example, contain from 50% to 80% by weight and preferably from 60% to 70% by weight of karanj a oil .
• the polyester used according to the invention results from the reaction between (i) a C 20 -C44 carboxylic acid dimer, (ii) at least one polyol and (iii) optionally at least one C 8 -C 32 monoalcohol and/or at least one C 8 -C 3 6 monocarboxylic acid.
• the C 20 -C44 carboxylic acid dimers are oligomers of two identical or different monomers, which are obtained from two linear or cyclic, unsaturated C 1 0-C 22 monocarboxylic acids, according to a reaction well known to those skilled in the art.
• unsaturated fatty acids are usually contained in pin oil (Tall oil), rapeseed oil, corn oil, sunflower oil, soybean oil, grapeseed oil and linseed oil, and are also eicosapentaenoic acid and docosahexaenoic acid which are found in fish oils.
• Cis fatty acids derived from pine oil, soybean oil or rapeseed oil are preferably used.
• dimers are often present as a mixture with trimers and possibly monomers of these fatty acids.
• fatty acid dimer/trimer mixtures mention may be made of the products sold by the company Croda under the trade name Pripol ® , by the company Cognis under the trade name Empol ® , by the company Oleon under the trade name Radiacid ® and by the company Arizona Chemicals under the trade name Unidyme ® .
• mixtures of oligomers comprising:
• these oligomers prefferably be present in hydrogenated form, in order to provide better stability with respect to oxidation and less coloration of the cosmetic composition.
• examples of such products include those sold by the company Croda under the trade names Pripol ® 1006 and 1009, by the company Cognis under the trade name Empol ® 1008 and by the company Oleon under the trade name Radiacid ® 0976.
• the acid dimer is copolymerized with at least one polyol, preferably an alkanediol. It may be a C 2 -C 10 alkanediol comprising a hydroxyl function at each end of its linear or branched alkylene chain.
• the polyol may be chosen from 1, 3-propanediol, 2-methyl- 1 , 3-propanediol , 1 , 4-butanediol , neopentyl glycol (or 2 , 2-dimethyl-l , 3-propanediol ) , 1 , 6-hexanediol and 12- hydroxystearyl alcohol.
• 1 , 3-Propanediol is preferably used according to the invention.
• the polyol may be chosen from a dimer diol such as dilinoleyl alcohol, (poly ) glycerols such as diglycerol and (poly ) alkylene glycols such as diethylene glycol.
• the polyester used according to the invention may be obtained solely from the abovementioned acid dimer (or the mixture of oligomers containing it) and from the abovementioned polyol.
• a polyester based on an alkanediol 1 , 3-propanediol or 1 , 4-butanediol in particular
• Viscoplast Green 3000 and Viscoplast 14436H are examples of alkanediol
• Another polyol-based polyester obtained from a dimer diol, such as the product of hydrogenation of the dilinoleic acid dimer, is the one sold in particular by the company Biosynthis under the trade name Viscoplast ® Green 3636.
• the polyester according to the invention can be obtained from the abovementioned compositions and also from a C8-C32 monoalcohol, preferably chosen from C 12 -C30 saturated linear alcohols, and more preferentially C16-C24 saturated linear alcohols, such as octyldodecanol .
• a C8-C32 monoalcohol preferably chosen from C 12 -C30 saturated linear alcohols, and more preferentially C16-C24 saturated linear alcohols, such as octyldodecanol .
• An example of such a polyester is sold by the company Biosynthis under the trade name Viscoplast ® Green 20000.
• the polyester according to the invention can be obtained from the carboxylic acid dimmer and the polyol mentioned above and also from at least one optionally hydroxylated and/or alkoxylated, C8-C36 monocarboxylic acid chosen from linear or branched, saturated C 8 -C 2 o acids such as hydroxystearic acid, isostearic acid and isononanoic acid or from the cinnamic acid derivatives such as ferulic acid.
• Polyesters of this type are in particular the products Viscoplast ® Green 1836G and 1836TG from the company Biosynthis. Mention can also be made of a copolyester obtained by copolymerizing dilinoleic acid, ferulic acid and propanediol.
• the polyester according to the invention generally does not contain any monomer other than those previously described .
• the composition according to the invention can, for example, contain from 5% to 30% by weight, and preferably from 8% to 15% by weight, of polyester, relative to the total weight of the composition.
• the mixture used for the production of this composition can contain from 20% to 50% by weight, and preferably from 30% to 40% by weight, of the polyester previously described.
• the composition according to the invention contains a physiologically acceptable medium, i.e. a medium which is compatible with the skin or the mucous membranes and optionally the skin appendages, more particularly a cosmetically acceptable medium, i.e. a medium which has a pleasant color, odor and feel and which does not cause any unacceptable discomfort for the user after application, such as tingling, tautness or red blotches.
• a physiologically acceptable medium i.e. a medium which is compatible with the skin or the mucous membranes and optionally the skin appendages
• a cosmetically acceptable medium i.e. a medium which has a pleasant color, odor and feel and which does not cause any unacceptable discomfort for the user after application, such as tingling, tautness or red blotches.
• this medium preferably does not contain alcohol.
• this composition generally comprises at least one other oil.
• oil is intended to mean a compound which is liquid at ambient temperature (25°C) and which, when it is introduced at at least 1% by weight into water at 25°C, is not at all soluble in the water, or is soluble in an amount of less than 10% by weight, relative to the weight of oil introduced into the water.
• oils include: hydrocarbons, (poly) esters and (poly) ethers and in particular (poly) esters of C 2 -C 2 4 (preferably C 6 -C 2 o) acids or hydroxy acids and of advantageously branched, C 2 -C 2 4 (preferably C 6 -C 20 ) alcohols or polyols and the plant oils containing same, dialkyl carbonates such as dicaprylyl carbonate, branched and/or unsaturated fatty acids (such as linoleic acid and linolenic acid), branched and/or unsaturated fatty alcohols (such as octyldodecanol and hexyldodecanol), silicone oils, fluorosilicone oils, fluoro oils, and also mixtures thereof.
• dialkyl carbonates such as dicaprylyl carbonate
• branched and/or unsaturated fatty acids such as linoleic acid and linolenic acid
• hydrocarbons examples include branched volatile hydrocarbons, such as isododecane or isohexadecane, and also non-volatile hydrocarbons such as polybutene, hydrogenated polyisobutene, polydecenes, hydrogenated polydecene, liquid paraffins and squalane.
• branched volatile hydrocarbons such as isododecane or isohexadecane
• non-volatile hydrocarbons such as polybutene, hydrogenated polyisobutene, polydecenes, hydrogenated polydecene, liquid paraffins and squalane.
• Cs-Ci 4 linear volatile alkanes derived in particular from plant sources, used alone or as mixtures of two alkanes differing by one or two carbon atoms, and in particular a mixture consisting: (i) of from 70% to 99% by weight of at least one linear alkane chosen from Cs, Cio and C 12 alkanes and mixtures thereof, preferably a C 12 alkane, and (ii) of from 1% to 30% by weight of at least one Ci 4 to C24 linear alkane, preferably a C14 alkane.
• a mixture is described more specifically in patent application WO 2010/115973 to which reference may be made for further details. It is also available from the company Biosynthis (INCI name: Coconut Alkanes) under the trade name Vegelight ® 1214.
• emollient mono-, di-, tri- and tetraesters such as ethyl acetate, isopropyl acetate, oleyl acetate, isononyl isononanoate, ethylhexyl isononanoate, hexyl neopentanoate, ethylhexyl neopentanoate, isodecyl neopentanoate, isostearyl neopentanoate, heptyl undecylenate, neopentyl glycol diheptanoate, neopentyl glycol diethyl hexanoate, pentaerythrityl tetraethylhexanoate, pentaerythrityl tetraisostearate, propanediol dicaprylate, neopen
• plant oils are, in particular, wheatgerm oil, sunflower oil, grapeseed oil, sesame oil, corn oil, apricot oil, castor oil, shea oil, avocado oil, olive oil, soybean oil, sweet almond oil, palm oil, rapeseed oil, cottonseed oil, hazelnut oil, macadamia oil, jojoba oil, alfalfa oil, poppy oil, pumpkin oil, sesame oil, marrow oil, rapeseed oil, blackcurrant oil, evening primrose oil, millet oil, barley oil, quinoa oil, rye oil, safflower oil, candlenut oil, passionflower oil, musk rose oil or camellia oil.
• silicone oil is intended to mean an oil comprising at least one silicon atom, and in particular at least one Si-0 group.
• non-volatile silicone oil mention may in particular be made of polydimethyl- siloxanes containing at least 8 silicon atoms, polyalkylmethylsiloxanes, the alkyl chain of which contains from 8 to 20 carbon atoms, and the oils identified by the INCI name phenyl trimethicone .
• volatile silicone oils mention may be made of cyclomethicones or cyclopolysiloxanes.
• Volatile linear alkanes having a flashpoint below 100°C
• plant oils such as coco caprylate/caprate and mixtures thereof (such as the product Vegelight ® 1214LC from Biosynthis, which is a mixture of C12 and C14 linear alkanes and of coco caprylate/caprate) are preferred for use in the present invention, owing to their plant origin .
• These oils can represent from 20% to 80% by weight, preferably from 30% to 70% by weight and better still from 40% to 60% by weight, relative to the total weight of the composition.
• composition according to the invention can also contain at least one of the following constituents: a fatty-phase gelling or structuring agent other than the abovementioned polyester, in particular at least one constituent chosen from: a plant, animal or hydrocarbon- based wax or else a linear fatty alcohol such as cetyl alcohol or a linear fatty acid such as stearic acid, a silicone gum, an olefin copolymer, in particular of Kraton ® type, a silicone elastomer, a polyamide resin or a polyester of a polyol of high molecular weight; a film- forming agent, such as a silicone resin or a hydrocarbon- based resin; an active agent; an organic or inorganic photoprotective agent or UV-screening agent other than karanja oil; a filler; an organic or inorganic pigment of spherical and/or lamellar structure (such as silica, talc, mica, etc) , which is optionally hydrophobically treated; a dye
• the composition according to the invention may contain at least one inorganic UV-screening agent, such as micronized titanium dioxide and micronized zinc oxide, and/or at least one organic UV-screening agent, such as octyl methoxy- cinnamate .
• This composition is preferably anhydrous, i.e. it contains less than 5% by weight of water, or even less than 1% by weight of water, and better still less than 0.5% by weight of water, the water not being added during the preparation of the composition, but corresponding to the residual water introduced by the ingredients that it contains. It may be in fluid form (solution or dispersion) , optionally packaged in a spray or impregnated in a wipe, in the form of a gel or in solid form, in particular in the form of a stick or of a bar.
• the composition according to the invention may contain at least 5% by weight of water and may, in this case, constitute a milk, a cream or a foam.
• the photoprotective properties of the composition according to the invention can be taken advantage of both in the cosmetics field, for preventing or limiting the effects on the skin of photoaging, in particular the formation of wrinkles and of pigmentary marks and slackening of the skin, and in the pharmaceutical field, in particular for preventing or limiting erythema, immunosuppression, photodermatosis and skin cancers.
• the subject of the present invention is therefore the cosmetic use of the composition previously described, for preventing aesthetic damage to the skin and/or hair caused by UV radiation, in particular for preventing or limiting the formation of wrinkles and of pigmentary marks and slackening of the skin.
• the subject of the present invention is also a composition as previously described, for use in the prevention of skin damage caused by UV radiation, in particular for preventing or limiting erythema, immunosuppression, photodermatosis and skin cancers.
• composition according to the invention may contain various ingredients which enable it to be used, in the cosmetics field, as a care (in particular anti-aging and/or depigmenting and/or slimming) and/or makeup product for facial and/or body skin and/or the lips or else as a hair product such as a shampoo, a leave-on or rinse-off hair conditioning product, or a hair dyeing product .
• a care in particular anti-aging and/or depigmenting and/or slimming
• makeup product for facial and/or body skin and/or the lips or else as a hair product such as a shampoo, a leave-on or rinse-off hair conditioning product, or a hair dyeing product .
• Example 1 Cosmetic compositions
• compositions containing the constituents identified in upper case letters below by their INCI name were prepared in a manner conventional for those skilled in the art.
• PROPANEDIOL COPOLYMER Viscoplast ® Green 20000 from BIOSYNTHIS 20.0%
• This gel has an SPF of 30, measured in vitro according to the HelioTest No. 1 protocol (Helioscience) and also provides effective protection against UVA radiation (PA+++) , evaluated according to HelioTest No. 2.
• the protocol of these tests is described in
• COCOS NUCIFERA OIL 1.0% COCONUT ALKANES AND COCO CAPRYLATE / CAPRATE
• DIBUTYL LAUROYL GLUTAMIDE 3.0% DIBUTYL ETHYLHEXANOYL GLUTAMIDE 2.0%
• This composition has an SPF of 20, measured in vitro, leaves a very soft and water-resistant film on the skin
• This oil can be applied to dry and damaged hair in order to repair the fibers thereof and to protect them against the sun.
• Example 2 Evaluation of the SPF-promoting effect of the polyester according to the invention
• composition A composition A
• composition B composition B
• composition B was also measured in vivo on 3 volunteers and was 30.
• This test demonstrates that the polyester according to the invention makes it possible to significantly increase the SPF and the UVA protection conferred by the karanja oil, since it makes it possible to obtain an SPF and a UVA protection index which are identical to a composition comprising 50% more karanja oil. It is thus possible to take advantage of the photoprotect ive properties of karanja oil while using a smaller amount thereof, and to obtain a composition which has better cosmetic properties.
• Example 3 Comparison of various fatty-phase structuring agents
• Each of these structuring agents was formulated in combination with 30% by weight of karanja oil, 25% by weight of a dispersion of titanium oxide and zinc oxide (at 33% of active material) and 10% by weight of gelled plant oils (Bioshine ® from Biosynthis), in a medium consisting of a mixture of C 12 and C14 linear alkanes and of coco caprylate/caprate (Vegelight ® 1214LC from Biosynthis), the amount of the medium being adjusted so as to obtain a total ingredient content of the composition of 100% by weight .
• the tests were carried out in a manner similar to example 1, on a PMMA plate.

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Citations (6)

• 2012
  • 2012-07-24 FR FR1257186A patent/FR2993777B1/fr active Active
• 2013
  • 2013-07-24 WO PCT/EP2013/065640 patent/WO2014016349A1/fr not_active Ceased

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