WO2022224918A1 - Composition comprenant deux esters d'acide gras de polyglycéryle avec de l'acide hyaluronique - Google Patents

Composition comprenant deux esters d'acide gras de polyglycéryle avec de l'acide hyaluronique Download PDF

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Publication number
WO2022224918A1
WO2022224918A1 PCT/JP2022/017975 JP2022017975W WO2022224918A1 WO 2022224918 A1 WO2022224918 A1 WO 2022224918A1 JP 2022017975 W JP2022017975 W JP 2022017975W WO 2022224918 A1 WO2022224918 A1 WO 2022224918A1
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Prior art keywords
fatty acid
weight
composition
less
acid ester
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PCT/JP2022/017975
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English (en)
Inventor
Rui Niimi
Yusuke IIMA
Yukinori Yamada
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L'oreal
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Priority claimed from JP2021073311A external-priority patent/JP2022167493A/ja
Priority claimed from FR2105572A external-priority patent/FR3123209B1/fr
Application filed by L'oreal filed Critical L'oreal
Publication of WO2022224918A1 publication Critical patent/WO2022224918A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron
    • 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
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent

Definitions

  • the present invention relates to a composition, preferably a cosmetic or dermatological composition, which comprises at least two different types of polyglyceryl fatty acid esters.
  • Oil-in- water (O/W) or water-in-oil (W/O) emulsions are well known in the field of cosmetics and dermatology, in particular for the preparation of cosmetic products, such as milks, creams, tonics, serums or toilet waters.
  • a fine emulsion such as an O/W nano- or micro-emulsion is particularly interesting in cosmetic products due to its transparent or slightly translucent aspect.
  • compositions including a polyglyceryl fatty acid ester have been known in the fields of cosmetics and dermatology.
  • Polyglyceryl fatty acid esters can function as surfactants, and therefore, they may be used to prepare, typically, emulsions such as oil-in- water (O/W) or water-in-oil (W/O) emulsions.
  • emulsions such as oil-in- water (O/W) or water-in-oil (W/O) emulsions.
  • Polyglyceryl fatty acid esters are preferable for environmental reasons, such as low environmental load, as compared to polyoxyethylene-based surfactants.
  • WO 2020/110716 discloses a composition in the form of a nano- or micro-emulsion including two polyglyceryl fatty acid esters, with a transparent or slightly translucent aspect.
  • hyaluronic acid ingredients such as sodium hyaluronate are known to provide moisturizing effects.
  • compositions including two classes of polyglyceryl fatty acid esters such as that disclosed in WO 2020/110716, has difficulty in including a hyaluronic acid ingredient, because it tends not to be transparent or slightly translucent.
  • An objective of the present invention is to provide a transparent or slightly translucent composition, even if the composition includes a combination of a hyaluronic acid ingredient and of the two classes of polyglyceryl fatty acid esters.
  • composition comprising:
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof;
  • the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second poly glyceryl fatty acid ester is from 0.01% to 5% by weight, relative to the total weight of the composition, the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is less than 0.3, the weight ratio of (the amount of the (c) second polyglyceryl fatty acid ester)/(the amount of the (b) first polyglyceiyl fatty acid ester) is more than 0.01 and less than 0.2, the weight ratio of (the amount of the (e) polyol with 5 or more carbon atoms)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is more than 0.1 and less than 5, and the composition comprises
  • the (a) oil may be selected from polar oils.
  • the amount of the (a) oil in the composition according to the present invention may be less than 0.7% by weight, preferably less than 0.6% by weight, and more preferably less than 0.5% by weight, relative to the total weight of the composition.
  • the (b) first polyglyceiyl fatty acid ester may comprise 2 to 4 glycerol units, preferably 3 or 4 glycerol units, and more preferably 4 glycerol units.
  • the fatty acid moiety of the (b) first polyglyceryl fatty acid ester may comprise 12 or fewer carbon atoms, preferably 11 or fewer carbon atoms, and more preferably 10 or fewer carbon atoms.
  • the amount of the (b) first polyglyceiyl fatty acid ester in the composition according to the present invention may be from 0.01% to 5% by weight, preferably from 0.1% to 4% by weight, and more preferably from 1% to 3% by weight, relative to the total weight of the composition.
  • the (c) second polyglyceiyl fatty acid ester may comprise 2 to 4 glycerol units, preferably 2 or 3 glycerol units, and more preferably 2 glycerol units.
  • the fatty acid moiety of the (c) second polyglyceiyl fatty acid ester may comprise 14 or more carbon atoms, preferably 16 or more carbon atoms, and more preferably 18 or more carbon atoms.
  • the amount of the (c) second polyglyceiyl fatty acid ester in the composition according to the present invention may be from 0.001% to 0.5% by weight, preferably from 0.01% to 0.4% by weight, and more preferably from 0.1 % to 0.3% by weight, relative to the total weight of the composition.
  • the (d) hyaluronic acid ingredient may be selected from hyaluronic acid, hydrolyzed hyaluronic acid, acetylated hyaluronic acid, cationic hyaluronic acid, salts thereof, and mixtures thereof.
  • the amount of the (d) hyaluronic acid ingredients) in the composition according to the present invention may be from 0.001% to 5% by weight, preferably from 0.01% to 4% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
  • the amount of the (e) polyol with 5 or more carbon atoms may be selected from diols with 5 or more carbon atoms, preferably C5-C10 diols, and more preferably pentyleleglycol, hexyleneglycol, and mixtures thereof.
  • the amount of the (e) polyol having 5 or more carbon atoms in the composition according to the present invention may range from 0.01% to 7% by weight, preferably from 0.1% to 6% by weight, more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • the present invention also relates to a cosmetic process for treating a keratin substance, comprising the step of applying the composition according to the present invention to the keratin substance.
  • composition includes a combination of hyaluronic acid or a salt thereof and of two classes of polyglyceryl fatty acid esters.
  • one aspect of the present invention is a composition comprising:
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof;
  • the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester is from 0.01% to 5% by weight, relative to the total weight of the composition, the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is less than 0.3, the weight ratio of (the amount of the (c) second polyglyceiyl fatty acid ester)/(the amount of the (b) first polyglyceryl fatty acid ester) is more than 0.01 and less than 0.2, the weight ratio of (the amount of the (e) polyol with 5 or more carbon atoms)/(the total amount of the (b) first polyglyceiyl fatty acid ester and the (c) second polyglyceiyl fatty acid ester) is more than 0.1 and less than 5, and the
  • composition according to the present invention can be transparent or slightly translucent because it has dispersed phases with a small size.
  • the composition according to the present invention may have a turbidity of 50 NTU or less, preferably 30 NTU or less, and more preferably 10 NTU or less.
  • composition according to the present invention can be in the form of a nano- or microemulsion, if it includes oil(s), although it includes hyaluronic acid(s) or salt(s) thereof.
  • the surfactant system used in the composition according to the present invention may be characterized by a combination of: at least one first polyglyceryl fatty acid ester having a higher HLB value; and at least one second polyglyceryl fatty acid ester having a lower HLB value.
  • the higher HLB value of the first polyglyceryl fatty acid ester may belong to a higher HLB numerical range
  • the lower HLB value of the second polyglyceryl fatty acid ester may belong to a lower HLB numerical range
  • the higher HLB numerical range and the lower HLB numerical range do not overlap each other.
  • composition according to the present invention may be less sticky, and therefore, it may provide a reduced sticky feeling to the touch. Therefore, the composition according to the present invention may provide an excellent feeling during use, in particular, feeling of the skin after application of the composition.
  • the term “sticky” here means a property which provides a tacky feeling to the skin.
  • composition according to the present invention may be prepared without a large amount of energy such as required by a homogenizer.
  • the composition according to the present invention may be prepared by using a small amount of energy such as gently stirring the ingredients of the composition. Therefore, the composition according to the present invention may be environmentally friendly in view of the preparation approach thereof.
  • composition according to the present invention will be explained in a more detailed manner.
  • composition according to the present invention may comprise (a) at least one oil. If two or more oils are used, they may be the same or different.
  • oil means a fatty compound or substance which is in the form of a liquid or a paste (nonsolid) at room temperature (25°C) under atmospheric pressure (760 mmHg).
  • oils those generally used in cosmetics can be used alone or in combination thereof. These oils may be volatile or non-volatile.
  • the (a) oil may be a non-polar oil such as a hydrocarbon oil, a silicone oil, or the like; a polar oil such as a plant or animal oil and an ester oil or an ether oil; or a mixture thereof.
  • the (a) oil may be selected from the group consisting of oils of plant or animal origin, synthetic oils, silicone oils, hydrocarbon oils, and fatty alcohols.
  • plant oils examples include, for example, linseed oil, camellia oil, macadamia nut oil, com oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil, and mixtures thereof.
  • animal oils mention may be made of, for example, squalene and squalane.
  • synthetic oils mention may be made of alkane oils such as isododecane and isohexadecane, ester oils, ether oils, and artificial triglycerides.
  • the ester oils are preferably liquid esters of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic monoalcohols or poly alcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • At least one from among the alcohol and the acid from which the esters of the present invention are derived is branched.
  • ethyl pabnitate ethyl hexyl palmitate
  • isopropyl palmitate dicaprylyl carbonate
  • alkyl myristates such as isopropyl myristate or ethyl myristate
  • isocetyl stearate 2-ethylhexyl isononanoate
  • isononyl isononanoate isodecyl neopentanoate
  • isostearyl neopentanoate isostearyl neopentanoate.
  • Esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C 1 -C 22 alcohols, and esters of monocarboxylic, dicarboxylic, or tricarboxylic acids and of non-sugar C4-C26 dihydroxy, trihydroxy, tetrahydroxy, or pentahydroxy alcohols may also be used.
  • ester oils one can use sugar esters and diesters of C6-C30 and preferably C 12 -C22 fatty acids.
  • sugar means oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides, or polysaccharides.
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 and preferably C 12 -C 22 fatty acids. If they are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters, and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates, and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate, and palmitostearate mixed esters, as well as pentaerythrityl tetraethyl hexanoate.
  • monoesters and diesters and especially sucrose, glucose, or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates, and oleostearates.
  • ester oils mention may be made of, for example, diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanoate, 2-ethylhexyl caprylate/caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicaprylyl carbonate, isopropyl lauroyl sarcosinate, isononyl isononanoate, ethylhexyl palmitate, isohexyl laurate, hex
  • artificial triglycerides mention may be made of, for example, capryl caprylyl glycerides, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate), and glyceryl tri(caprate/caprylate/linolenate).
  • capryl caprylyl glycerides glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, glyceryl tri(caprate/caprylate), and glyceryl tri(caprate/caprylate/linolenate).
  • silicone oils mention may be made of, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like; cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.
  • linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like
  • cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodeca
  • the silicone oil is chosen from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group.
  • PDMS liquid polydimethylsiloxanes
  • silicone oils may also be organomodified.
  • organomodified silicones that can be used in accordance with the present invention are silicone oils as defined above and comprise in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those having a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone® 7158 by Union Carbide, Silbione® 70045 V5 by Rhodia, and dodecamethylcyclopentasiloxane sold under the name Silsoft 1217 by Momentive Performance Materials, and mixtures thereof. Mention may also be made of cyclocopolymers of the type such as dimethylsiloxane/methylalkylsiloxane, such as Silicone Volatile® FZ 3109 sold by the company Union Carbide, of the formula:
  • organosilicon compounds such as the mixture of octamethylcyclotetrasiloxane and tefratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcycl
  • decamethyltetrasiloxane sold in particular under the name SH 200 by the company Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, pp. 27-32, Todd & Byers, Volatile Silicone Fluids for Cosmetics. The viscosity of the silicones is measured at 25°C according to ASTM standard 445 Appendix C.
  • Non-volatile polydialkylsiloxanes may also be used. These non-volatile silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups.
  • polydialkylsiloxanes mention may be made, in a non-limiting manner, of the following commercial products: the Silbione ® oils of the 47 and 70047 series or the Mirasil ® oils sold by Rhodia, for instance the oil 70047 V 500000; the oils of the Mirasil ® series sold by the company Rhodia; the oils of the 200 series from the company Dow Coming, such as DC200 with a viscosity of 60000 mm 2 /s; and the Viscasil ® oils from General Electric and certain oils of the SF series (SF 96, SF 18) from General Electric.
  • the Silbione ® oils of the 47 and 70047 series or the Mirasil ® oils sold by Rhodia for instance the oil 70047 V 500000
  • the oils of the Mirasil ® series sold by the company Rhodia the oils of the 200 series from the company Dow Coming, such as DC200 with a viscosity of 60000 mm 2 /s
  • CTFA dimethiconol
  • silicones containing aryl groups mention may be made of polydiarylsiloxanes, especially polydiphenylsiloxanes and polyalkylarylsiloxanes such as phenyl silicone oil.
  • the phenyl silicone oil may be chosen from the phenyl silicones of the following formula:
  • Ci- C30 hydrocarbon-based radicals preferably C1-C12 hydrocarbon-based radicals, and more preferably C1-C6 hydrocarbon-based radicals, in particular methyl, ethyl, propyl, or butyl radicals
  • m, n, p, and q are, independently of each other, integers of 0 to 900 inclusive, preferably 0 to 500 inclusive, and more preferably 0 to 100 inclusive, with the proviso that the sum n+m+q is other than 0.
  • oils of the 70641 series from Rhodia examples include the products sold under the following names: the Silbione® oils of the 70641 series from Rhodia; the oils of the Rhodorsil® 70633 and 763 series from Rhodia; the oil Dow Coming 556 Cosmetic Grade Fluid from Dow Coming; the silicones of the PK series from Bayer, such as the product PK20; certain oils of the SF series from General Electric, such as SF 1023, SF 1154, SF 1250, and SF 1265.
  • the organomodified liquid silicones may especially contain polyethyleneoxy and/or polypropyleneoxy groups . Mention may thus be made of the silicone KF-6017 proposed by Shin-Etsu, and the oils Silwet® L722 and L77 from the company Union Carbide.
  • the hydrocarbon oils may be chosen from: linear or branched, optionally cyclic, C6-C16 lower alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane, and isoparaffins, for instance isohexadecane, isododecane, and isodecane; and linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffins, liquid petroleum jelly, polydecenes and hydrogenated polyisobutenes such as Parleam®, and squalane.
  • hydrocarbon oils As preferable examples of hydrocarbon oils, mention may be made of, for example, linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymer; and mixtures thereof.
  • linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymer; and mixtures thereof.
  • fatty in the fatty alcohol means the inclusion of a relatively large number of carbon atoms. Thus, alcohols which have 4 or more, preferably 6 or more, and more preferably 12 or more carbon atoms are encompassed within the scope of fatty alcohols.
  • the fatty alcohol may be saturated or unsaturated.
  • the fatty alcohol may be linear or branched.
  • the fatty alcohol may have the structure R-OH wherein R is chosen from saturated and unsaturated, linear and branched radicals containing from 4 to 40 carbon atoms, preferably from 6 to 30 carbon atoms, and more preferably from 12 to 20 carbon atoms.
  • R may be chosen from C 12 -C 20 alkyl and C 12 -C 20 alkenyl groups. R may or may not be substituted with at least one hydroxyl group.
  • fatty alcohol examples include lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, undecylenyl alcohol, myristyl alcohol, octyldodecanol, hexyldecanol, oleyl alcohol, linoleyl alcohol, palmitoleyl alcohol, arachidonyl alcohol, erucyl alcohol, and mixtures thereof.
  • the fatty alcohol be a saturated fatty alcohol.
  • the fatty alcohol may be selected from straight or branched, saturated or unsaturated C6-C30 alcohols, preferably straight or branched, saturated C 6 -C 30 alcohols, and more preferably straight or branched, saturated C 12 -C 20 alcohols.
  • saturated fatty alcohol here means an alcohol having a long aliphatic saturated carbon chain. It is preferable that the saturated fatty alcohol be selected from any linear or branched, saturated C 6 -C 30 fatty alcohols. Among the linear or. branched, saturated C6-C30 fatty alcohols, linear or branched, saturated C 12 -C 20 fatty alcohols may preferably be used. Any linear or branched, saturated C 16 -C 20 fatty alcohols may be more preferably used. Branched C 16 -C20 fatty alcohols may be even more preferably used.
  • saturated fatty alcohols mention may be made of lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, undecylenyl alcohol, myristyl alcohol, octyldodecanol, hexyldecanol, and mixtures thereof.
  • cetyl alcohol, stearyl alcohol, octyldodecanol, hexyldecanol, or a mixture thereof (e.g., cetearyl alcohol) as well as behenyl alcohol can be used as a saturated fatty alcohol.
  • the fatty alcohol used in the composition according to the present invention is preferably chosen from cetyl alcohol, octyldodecanol, hexyldecanol, and mixtures thereof.
  • the (a) oil be chosen from oils with a molecular weight below 600 g/mol.
  • the (a) oil has a low molecular weight such as below 600 g/mol, chosen among ester oils with a short hydrocarbon chain or chains (C 1 -C 12 ) (e.g., isopropyl lauroyl sarcosinate, isopropyl myristate, isopropyl palmitate, isononyl isononanoate, and ethyl hexyl palmitate), silicone oils (e.g., volatile silicones such as cyclohexasiloxane), hydrocarbon oils (e.g., isododecane, isohexadecane, and squalane), branched and/or unsaturated fatty alcohol (C12-C30) type oils such as octyldodecanol and oleyl alcohol, and ether oils such as dicaprylyl ether.
  • C 1 -C 12 e.g., isopropyl lauroyl sarcosinate,
  • the (a) oil may be chosen from polar oils, preferably from ester oils, and more preferably isopropyl myristate, and from non-polar oils, preferably ether oils, and more preferably dicaprylyl ether.
  • the amount of the (a) oil(s) in the composition according to the present invention may be 0.001% by weight or more, preferably 0.01% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the (a) oil(s) in the composition according to the present invention may be less than 0.7% by weight, preferably less than 0.6% by weight, and more preferably less than 0.5% by weight, relative to the total weight of the composition.
  • the amount of the (a) oil(s) in the composition according to the present invention may be from 0.001% to less than 0.7% by weight, preferably from 0.01% to less than 0.6% by weight, and more preferably from 0.1% to less than 0.5% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (b) at least one first polyglyceryl fatty acid ester having an HLB value of more than 11.0, preferably more than 12.0, and more preferably more than 13.0.
  • a single type of (b) first polyglyceryl fatty acid ester may be used, but two or more different types of (b) first polyglyceiyl fatty acid ester may be used in combination.
  • the (b) first polyglyceryl fatty acid ester can function as a surfactant, in particular a nonionic surfactant.
  • the (b) first polyglyceiyl fatty acid ester may have an HLB value of from more than 11.0 to 17.0, preferably from more than 12.0 to 16.0, and more preferably from more than 13.0 to 15.0.
  • HLB hydrophilic-lipophilic balance
  • the HLB value is determined by the weighted average of the HLB values of all the (b) first polyglyceiyl fatty acid esters.
  • the (b) first polyglyceryl fatty acid ester may be chosen from mono, di, tri and more esters of saturated or unsaturated fatty acid(s).
  • the (b) first polyglyceiyl fatty acid ester comprises 2 to 4 glycerol units, preferably 3 or 4 glycerol units, and more preferably 4 glycerol units.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (b) first polyglyceiyl fatty acid ester may comprise 12 or fewer carbon atoms, preferably 11 or fewer carbon atoms, and more preferably 10 or fewer carbon atoms.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (b) first polyglyceryl fatty acid ester may comprise 4 or more carbon atoms, preferably 6 or more carbon atoms, and more preferably 8 or more carbon atoms.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (b) first polyglyceryl fatty acid ester may have carbon atoms of from 4 to 12, preferably from 6 to 11, and more preferably from 8 to 10 carbon atoms.
  • the fatty acid for the fatty acid moiety of the (b) first polyglyceryl fatty acid ester may be saturated or unsaturated, and may be selected from caprylic acid, capric acid, and lauric acid.
  • the (b) first polyglyceryl fatty acid ester(s) may be selected from the group consisting of PG3 caprate (HLB: about 14), PG4 caprylate (HLB: 14), PG4 laurate (HLB: about 14), PG4 caprate (HLB:
  • PG5 myristate HLB: 15.4
  • PG5 stearate HLB: 15
  • PG6 caprylate HLB: 14.6
  • PG6 caprate HLB: 13.1
  • PG6 laurate HLB: 14.1
  • PG10 laurate HLB: 15.2
  • PG10 myristate HLB: 14.9
  • PG10 stearate HLB: 14.1
  • PG10 isostearate HB: 13.7
  • PG10 oleate HB: 13.0
  • PG10 cocoate HLB: 16
  • the (b) first polyglyceryl fatty acid ester(s) be selected from the group consisting of PG3 caprate (HLB: about 14), PG4 capiylate (HLB: 14), PG4 laurate (HLB: about 14), PG4 caprate (HLB: 14), and mixtures thereof.
  • the amount of the (b) first polyglyceryl fatty acid ester(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (b) first polyglyceryl fatty acid ester(s) in the composition according to the present invention may be 5% by weight or less, preferably 4% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.
  • the amount of the (b) first polyglyceryl fatty acid ester(s) in the composition according to the present invention may range from 0.01% to 5% by weight, preferably from 0.1% to 4% by weight, and more preferably from 1% to 3% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (c) at least one second polyglyceiyl fatty acid ester having an HLB value of less than 11.0, preferably less than 10.0, and more preferably less than 9.0.
  • a single type of (c) second polyglyceiyl fatty acid ester may be used, but two or more different types of (c) second polyglyceiyl fatty acid ester may be used in combination.
  • the (c) second polyglyceryl fatty acid ester can function as a surfactant, in particular a nonionic surfactant.
  • the (c) second polyglyceryl fatty acid ester may have an HLB value of from 5.0 to less than 11.0, preferably from 6.0 to less than 10.0, and more preferably from 7.0 to less than 9.0.
  • the HLB value is determined by the weighted average of the HLB values of all the (c) second polyglyceiyl fatty acid esters.
  • the (c) second polyglyceiyl fatty acid ester may be chosen from mono, di, tri and more esters of saturated or unsaturated fatty acid(s).
  • the (c) second polyglyceiyl fatty acid ester comprises 2 to 4 glycerol units, preferably 2 or 3 glycerol units, and more preferably 2 glycerol units.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (c) second polyglyceiyl fatty acid ester may comprise 14 or more carbon atoms, preferably 16 or more carbon atoms, and more preferably 18 or more carbon atoms.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (c) second polyglyceiyl fatty acid ester may comprise 30 or fewer carbon atoms, preferably 24 or fewer carbon atoms, and more preferably 20 or fewer carbon atoms.
  • the fatty acid for the fatty acid moiety or the fatty acid moiety of the (c) second polyglyceryl fatty acid ester may have from 14 to 30, preferably from 16 to 24, and more preferably from 18 to 20 carbon atoms.
  • the fatty acid for the fatty acid moiety of the (c) second polyglyceryl fatty acid ester may be saturated or unsaturated, and may be selected from myristic acid, stearic acid, isostearic acid, and oleic acid.
  • the (c) second polyglyceryl fatty acid ester(s) may be selected from the group consisting of PG2 stearate (HLB: 5.0), PG2 distearate (HLB: 4), PG2 isostearate (HLB: 8), PG2 diisostearate (HLB: 3.2), PG2 triisostearate (HLB: 3), PG2 sesquiisostearate (HLB: about 4), PG2 oleate (HLB: 8), PG2 sesquioleate (HLB: 5.3), PG3 distearate (HLB: 5), PG3 diisostearate (HLB: 5), PG3 dicocoate (HLB: 7), PG5 hexastearate (HLB: 4.0), PG5 trioleate (HLB: 7.0), PG10 pentaoleate (HLB: 6.4), PG2 sesquicaprylate (HLB: about 8), PG2 caprate (HLB: 9.5), PG
  • the (c) second polyglyceryl fatty acid ester be selected from the group consisting of PG2 stearate (HLB: 5.0), PG2 distearate (HLB: 4), PG2 isostearate (HLB: 8), PG2 diisostearate (HLB: 3.2), PG2 triisostearate (HLB: 3), PG2 sesquiisostearate (HLB: about 4), PG2 oleate (HLB: 8), PG2 sesquioleate (HLB: 5.3), PG3 distearate (HLB: 5), PG3 diisostearate (HLB: 5), PG3 dicocoate (HLB: 7), PG2 sesquicaprylate (HLB: about 8), PG2 caprate (HLB: 9.5), PG2 laurate (HLB: 8.5), PG2 myristate (HLB: 10), PG2 isopalmitate (HLB: 9), PG4 ole
  • the amount of the (c) second polyglyceryl fatty acid ester(s) in the composition according to the present invention may be 0.001% by weight or more, preferably 0.01% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the (c) second poly glyceryl fatty acid ester(s) in the composition according to the present invention may be 0.5% by weight or less, preferably 0.4% by weight or less, and more preferably 0.3% by weight or less, relative to the total weight of the composition.
  • the amount of the (c) second polyglyceryl fatty acid ester(s) in the composition according to the present invention may range from 0.001% to 0.5% by weight, preferably from 0.01% to 0.4% by weight, more preferably from 0.1% to 0.3% by weight, relative to the total weight of the composition.
  • the composition according to the present invention comprises (d) at least one hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof.
  • a single type of hyaluronic acid ingredient may be used, but two or more different types of hyaluronic acid ingredients may be used in combination.
  • Hyaluronic acid is a predominant glucosaminoglycan found in the skin. Thus, the fibroblasts synthesize predominantly collagens, matrix glycoproteins other than collagens (fibronectin, laminin), proteoglycans and elastin. The keratinocytes, for their part, synthesize predominantly sulfated glycosaminoglycans and hyaluronic acid.
  • Hyaluronic acid is also called hyaluronan.
  • Hyaluronic acid is present in the free state in the epidermis and in the dermis and is responsible for turgescence of the skin. This polysaccharide can in fact retain a large volume of water, corresponding to up to 1000 times its weight. In this sense, hyaluronic acid plays an important role in increasing the amounts of water bound in the tissue, and also in the mechanical properties of the skin and in wrinkle formation.
  • Hyaluronic acid can be represented by the following chemical formula.
  • hyaluronic acid covers in particular the basic unit of hyaluronic acid of formula:
  • hyaluronic acid comprising a disaccharide dimer, namely D- glucuronic acid and N-acetylglucosamine.
  • Hyaluronic acid derivatives may be selected from the group consisting of hydrolyzed hyaluronic acid, acetylated hyaluronic acid, cationic hyaluronic acid, and mixtures thereof.
  • the cationic hyaluronic acid comprises at least one cationic moiety.
  • the cationic moiety may be a trialkyl ammonium group such as -N + (CH3)3.
  • the cationic moiety may include at least one hydroxyl group.
  • the examples of the cationic group include -CH2-CH(OH)-CH2-N + (CH3)3 ⁇
  • Examples of the cationic hyaluronic acid includes hydroxypropyl trimonium hyaluronate.
  • hyaluronic acid salts or hyaluronic acid derivative salts mention may be made of alkaline metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as magnesium salts, ammonium salts, and mixtures thereof.
  • the molecular weight of hyaluronic acid ingredient is not limited.
  • the molecular weight of hyaluronic acid ingredient may be 5 kDa or more, preferably 20 kDa or more, and more preferably 100 kDa or more.
  • the molecular weight of hyaluronic acid ingredient may be 20 MDa or less, preferably 10 MDa or less, and more preferably 2,000 kDa or less.
  • the molecular weight of hyaluronic acid ingredient may be from 5 kDa to 20 MDa, preferably from
  • molecular weight may mean a number average molecular weight.
  • Hyaluronic acid ingredient may in particular be hyaluronic acid supplied by the company Hyactive under the trade name CPN (MW: 10 to 150 kDa), by the company Soliance under the trade name Cristalhyal (MW: 1 to 1.4 MDa), by the company Bioland under the name Nutra HA (MW: 820000 Da), by the company Bioland under the name Nutra AF (MW: 69000 Da), or by the company Bioland under the name Oligo HA (MW : 6100 Da).
  • CPN MW: 10 to 150 kDa
  • Cristalhyal MW: 1 to 1.4 MDa
  • Nutra HA MW: 820000 Da
  • Nutra AF MW: 69000 Da
  • Oligo HA MW : 6100 Da
  • a single hyaluronic acid ingredient with a single molecular weight, or a combination of two or more hyaluronic acid ingredients with different molecular weights may be used.
  • the amount of the (d) hyaluronic acid ingredient(s) in the composition according to the present invention may be 0.001% by weight or more, preferably 0.01% by weight or more, and more preferably 0.1% by weight or more, relative to the total weight of the composition.
  • the amount of the (d) hyaluronic acid ingredient(s) in the composition according to the present invention may be 5% by weight or less, preferably 4% by weight or less, and more preferably 3% by weight or less, relative to the total weight of the composition.
  • the amount of the (d) hyaluronic acid ingredient(s) in the composition according to the present invention may range from 0.001% to 5% by weight, preferably from 0.01% to 4% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (e) at least one polyol with 5 or more carbon atoms.
  • a single type of such polyol may be used, but two or more different types of such polyol may be used in combination.
  • the polyol with 5 or more carbon atoms may be selected from diols with 5 or more carbon atoms, preferably C 5 -C 10 diols, and more preferably pentyleleglycol, hexyleneglycol, and mixtures thereof.
  • Pentyleneglycol encompasses isomers thereof.
  • pentyleneglycol may be 1,2- pentyleneglycol, 1,3-pentyleneglycol, 1,4-pentyleneglycol, 1,5-pentyleneglycol, 2,3- pentyleneglycol, and 2,4-penyleneglycol.
  • 1 ,2-pentyleneglycol may be preferable.
  • Hexyleneglycol encompasses isomers thereof.
  • hexyleneglycol may be 1,2- hexyleneglycol, 1,3-hexyleneglucol, 1,4-hexyleneglycol, 1,5-hexyleneglycol, 1,6-hexyleneglycol, 2,3-hexyleneglycol, 2,4-hexyleneglycol, 2,5-hexyleneglycol, and 2-methyl-2,4-pentanediol. 2- methyl-2, 4-pentanediol may be preferable.
  • the amount of the (e) polyol(s) with 5 or more carbon atoms in the composition according to the present invention may be 0:01 % by weight or more, preferably 0.1 % by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the (e) polyol(s) with 5 or more carbon atoms in the composition according to the present invention may be 7% by weight or less, preferably 6% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the (e) polyol(s) with 5 or more carbon atoms in the composition according to the present invention may range from 0.01% to 7% by weight, preferably from 0.1% to 6% by weight, and more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises (f) water.
  • the amount of the (f) water in the composition according to the present invention may be 50% by weight or more, preferably 60% by weight or more, and more preferably 70% by weight or more, relative to the total weight of the composition.
  • the amount of the (f) water in the composition according to the present invention may be 95% by weight or less, preferably 90% by weight or less, and more preferably 85% by weight or less, relative to the total weight of the composition.
  • the amount of (f) water in the composition according to the present invention may range from 50% to 95% by weight, preferably from 60% to 90% by weight, more preferably from 70% to 85% by weight, relative to the total weight of the composition.
  • the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester in the composition according to the present invention is from 0.01% to 5% by weight, preferably from 0.02% to 4.5% by weight, and more preferably from 1% to 4% by weight, relative to the total weight of the composition.
  • the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) in the composition according to the present invention is less than 0.3, preferably less than 0.2, and more preferably less than 0.1.
  • composition according to the present invention may not include any (a) oil.
  • the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester may form micelles, which can form dispersed phases in the composition according to the present invention, including no (a) oil.
  • the composition according to the present invention may include (a) oil.
  • the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester may form micelles, which can form dispersed phases in the composition according to the present invention, including the (a) oil.
  • the micelle including (a) oil can be regarded as an “oil” droplet.
  • the weight ratio of (the amount of the (c) second polyglyceryl fatty acid ester)/(the amount of the (b) first polyglyceryl fatty acid ester) in the composition according to the present invention is more than 0.01 and less than 0.2, preferably more than 0.02 and less than 0.19, and more preferably more than 0.03 and less than 0.18.
  • the weight ratio of (the amount of the (e) polyol with 5 or more carbon atoms)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) in the composition according to the present invention is more than 0.1 and less than 5, preferably more than 0.15 and less than 4.5, and more preferably more than 0.2 and less than 4.0.
  • composition according to the present invention may comprise at least one additional polyol other than the (e) polyol with 5 or more carbon atoms.
  • additional polyol other than the (e) polyol with 5 or more carbon atoms.
  • a single type of such additional polyol may be used, but two or more different types of such additional polyol may be used in combination.
  • polyol here means an alcohol having two or more hydroxy groups, and does not encompass a saccharide or a derivative thereof.
  • the derivative of a saccharide includes a sugar alcohol which is obtained by reducing one or more carbonyl groups of a saccharide, as well as a saccharide or a sugar alcohol in which the hydrogen atom or atoms in one or more hydroxy groups thereof has or have been replaced with at least one substituent such as an alkyl group, a hydroxyalkyl group, an alkoxy group, an acylgroup or a carbonyl group.
  • the polyol may be a C 2-C4 polyol, preferably a C 2-C4 polyol, comprising at least 2 hydroxy groups, and preferably 2 to 5 hydroxy groups.
  • the polyol may be a natural or synthetic polyol.
  • the polyol may have a linear, branched or cyclic molecular structure.
  • the polyol may be selected from glycerins and derivatives thereof, and glycols and derivatives thereof.
  • the polyol may be selected from the group consisting of glycerin, ethyleneglycol, propyleneglycol, and butyleneglycol.
  • the amount of the additional polyol(s) in the composition according to the present invention may be 20% by weight or less, preferably 15% by weight or less, and more preferably 10% by weight or less, relative to the total weight of the composition.
  • the amount of the additional polyol(s) in the composition according to the present invention may be from 1% to 20% by weight, preferably from 3% to 15% by weight, and more preferably from 5% to 10% by weight, relative to the total weight of the composition.
  • composition according to the present invention includes no butyleneglycol.
  • composition according to the present invention may contain one or more monoalcohols which are in the form of a liquid at room temperature (25 °C), such as for example linear or branched monoalcohols comprising from 1 to 6 carbon atoms, such as ethanol, propanol, butanol, isopropanol, isobutanol, pentanol, and hexanol.
  • monoalcohols which are in the form of a liquid at room temperature (25 °C)
  • monoalcohols comprising from 1 to 6 carbon atoms, such as ethanol, propanol, butanol, isopropanol, isobutanol, pentanol, and hexanol.
  • the amount of the monoalcohol(s) in the composition according to the present invention may be 0.01% by weight or more, preferably 0.1% by weight or more, and more preferably 1% by weight or more, relative to the total weight of the composition.
  • the amount of the monoalcohol(s) in the composition according to the present invention may be 15% by weight or less, preferably 10% by weight or less, and more preferably 5% by weight or less, relative to the total weight of the composition.
  • the amount of the monoalcohol(s) in the composition according to the present invention may range from 0.01 % to 15% by weight, preferably from 0.1 % to 10% by weight, and more preferably from 1% to 5% by weight, relative to the total weight of the composition.
  • composition according to the present invention may also include various adjuvants conventionally used in cosmetic and dermatological compositions, such as thickeners, anionic, non-ionic, cationic, and amphoteric or zwitterionic polymers, anionic, additional non-ionic, cationic, and amphoteric surfactants, antioxidants, coloring agents, chelating agents, sequestering agents, fragrances, dispersing agents, conditioning agents, film-forming agents, preservatives, co-preservatives, and mixtures thereof, except for the ingredients as explained above.
  • adjuvants conventionally used in cosmetic and dermatological compositions, such as thickeners, anionic, non-ionic, cationic, and amphoteric or zwitterionic polymers, anionic, additional non-ionic, cationic, and amphoteric surfactants, antioxidants, coloring agents, chelating agents, sequestering agents, fragrances, dispersing agents, conditioning agents, film-forming agents, preservatives, co-preservatives, and
  • the composition according to the present invention is free from a polyglyceryl fatty acid ester comprising 5 or more glycerol units such as PG5 laurate.
  • the term “free from” here means that the composition according to the present invention may contain a limited amount of a polyglyceryl fatty acid ester comprising 5 or more glycerol units.
  • the amount of the polyglyceryl fatty acid ester comprising 5 or more glycerol units be limited such that it is less than 1% by weight, more preferably less than 0.1% by weight, and even more preferably less than 0.01% by weight, relative to the total weight of the composition. It is most preferable that the composition according to the present invention comprise no polyglyceryl fatty acid ester comprising 5 or more glycerol units.
  • the composition according to the present invention is free from a polyoxyethylene-based nonionic surfactant.
  • the term “free from” here means that the composition according to the present invention may contain a limited amount of a polyoxyethylene-based nonionic surfactant.
  • the amount of the polyoxyethylene-based nonionic surfactant be limited such that it is less than 1% by weight, more preferably less than 0.1% by weight, and even more preferably less than 0.01% by weight, relative to the total weight of the composition. It is most preferable that the composition according to the present invention comprises no polyoxyethylene-based nonionic surfactant.
  • composition according to the present invention can be prepared by mixing the essential ingredient(s) as explained above, and optional ingredient(s), if necessary, as explained above.
  • the method and means to mix the above essential and optional ingredients are not limited. Any conventional method and means can be used to mix the above essential and optional ingredients to prepare the composition according to the present invention.
  • the composition according to the present invention may be prepared without a large amount of energy such as required by a homogenizer. Thus, the composition according to the present invention may be prepared by using a small amount of energy such as gently stirring the ingredients of the composition. Therefore, the composition according to the present invention is environmentally friendly in view of the preparation approach thereof.
  • composition according to the present invention comprises a continuous phase and dispersed phases.
  • the dispersed phases are dispersed in the continuous phase.
  • the dispersed phase may be in the form of a particle.
  • the continuous phase can comprise (f) water.
  • the dispersed phase can comprise, at least, the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester.
  • the dispersed phase can also comprise the (a) oil, if the composition comprises the (a) oil. If the dispersed phase comprises the (a) oil, the dispersed phase may be recognized as an oil droplet. If the dispersed phase does not comprises the (a) oil, the dispersed phase comprises the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester, wherein the two polyglyceryl fatty acid esters may form a micelle.
  • the size of the dispersed phase is 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less.
  • the size can be measured as a volume-based average size.
  • the size can be measured by dynamic light scattering with, for example, a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • ELSZ-2000 Otsuka Electronics Co.Ltd.
  • the minimum size of the dispersed phase is not limited, but it may be 1 nm or more, 5 nm or more, or 10 nm or more.
  • composition according to the present invention may be in the form of a nano- or microemulsion, if the composition comprises (a) oil.
  • micro-emulsion may be defined in two ways, namely, in a broad sense and in a narrow sense. That is to say, there is the one case (“micro-emulsion in the narrow sense”) in which the micro-emulsion refers to a thermodynamically stable isotropic single liquid phase containing a ternary system having three ingredients of an oily component, an aqueous component and a surfactant, and there is the second case (“micro-emulsion in the broad sense”) in which among thermodynamically unstable typical emulsion systems the micro-emulsion additionally includes those such emulsions presenting transparent or slightly translucent appearances due to their smaller particle sizes (Satoshi Tomomasa, et al., Oil Chemistry, Vol. 37, No. 11 (1988), pp. 48-53).
  • the "micro-emulsion” as used herein refers to a "micro-emulsion in the narrow sense", i.e., a thermodynamically stable isotropic single liquid phase.
  • the micro-emulsion refers to either one state of an O/W (oil-in- water) type microemulsion in which oil is solubilized by micelles, a W/O (water-in-oil) type microemulsion in which water is solubilized by reverse micelles, or a bicontinuous microemulsion in which the number of associations of surfactant molecules are rendered infinite so that both the aqueous phase and oil phase have a continuous structure.
  • O/W oil-in- water
  • W/O water-in-oil
  • the micro-emulsion may have a dispersed phase with a particle size of 100 nm or less, preferably 80 nm or less, and more preferably 60 nm or less, measured by laser granulometry.
  • nano-emulsion here means an emulsion characterized by a dispersed phase with a size of less than 350 ran, the dispersed phase being stabilized by a crown of the nonionic surfactants (b) and (c) that may optionally form a liquid crystal phase of lamellar type, at the dispersed phase/continuous phase interface.
  • the transparency of the nano-emulsions arises from the small size of the dispersed phase, this small size being obtained by virtue of the use of mechanical energy.
  • Nanoemulsions can be distinguished from microemulsions by their structure.
  • micro-emulsions are thermodynamically stable dispersions formed from, for example, micelles which are formed by the ingredients (b) and (c) and swollen with the ingredient (a).
  • microemulsions do not require substantial mechanical energy in order to be prepared.
  • the nano-emulsion may have a dispersed phase with a particle size of 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less, measured by laser granulometry.
  • composition according to the present invention be in the form of an O/W emulsion which comprises oil phases dispersed in a continuous aqueous phase.
  • the dispersed oil phases can be oil droplets in the aqueous phase.
  • the O/W architecture or structure which consists of oil phases dispersed in an aqueous phase, has an external aqueous phase, and therefore if the composition according to the present invention has the O/W architecture or structure, it can provide a pleasant feeling during use because of the feeling of immediate freshness that the aqueous phase can provide.
  • the particle size of the (a) oil may be 100 nm or less, preferably 75 nm or less, and more preferably 50 nm or less.
  • the particle size can be measured by a dynamic light scattering method.
  • the particle size measurement can be performed by, for example, the Particle Size Analyzer ELSZ-2000 series, marketed by Otsuka Electronics Co., Ltd.
  • the particle size can be a volume-average particle diameter or a number-average particle diameter, preferably a volume-average particle diameter.
  • composition according to the present invention can be transparent or slightly translucent.
  • the transparency may be measured by measuring the turbidity (for example, turbidity can be measured with a 2100Q (marketed by Hach Company) having a round cell (25 mm in diameter and 60 mm height) and a tungsten filament lamp which can emit visible light (between 400 and 800 nm, preferably from 400 to 500 nm).
  • the measurement can be performed on the undiluted composition.
  • the blank may be determined with distilled water.
  • composition according to the present invention may have a turbidity of 50 NTU or less, preferably 30 NTU or less and more preferably 10 NTU or less.
  • composition according to the present invention be a cosmetic or dermatological composition, preferably a cosmetic composition, and more preferably a cosmetic composition for a keratin substance such as skin.
  • composition according to the present invention can be used for a non-therapeutic process, such as a cosmetic process, for treating a keratin substance such as skin, hair, mucous membranes, nails, eyelashes, eyebrows and/or scalp, by being applied to the keratin substance.
  • a non-therapeutic process such as a cosmetic process
  • a keratin substance such as skin, hair, mucous membranes, nails, eyelashes, eyebrows and/or scalp
  • the present invention also relates to a cosmetic process for treating a keratin substance, comprising the step of applying the composition according to the present invention to the keratin substance.
  • the present invention may also relate to a use of the composition according to the present invention as a cosmetic product or in a cosmetic product such as care products, washing products, make-up products, make-up-removing products, for body and/or facial skin and/or mucous membranes and/or the scalp and/or the hair and/or the nails and/or the eyelashes and/or the eyebrows.
  • composition according to the present invention can be used, as it is, as a cosmetic product.
  • the composition according to the present invention can be used as an element of a cosmetic product.
  • the composition according to the present invention can be added to or combined with any other elements to form a cosmetic product.
  • the care product may be a lotion, a cream, a hair tonic, a hair conditioner, a sun screening agent, and the like.
  • the washing product may be a shampoo, a face wash, a hand wash and the like.
  • the makeup product may be a foundation, a mascara, a lipstick, a lip gloss, a blusher, an eye shadow, a nail varnish, and the like.
  • the make-up-removing product may be a make-up cleansing agent and the like.
  • composition according to the present invention includes at least one hyaluronic acid or a salt thereof
  • the composition according to the present invention may preferably be used for moisturizing keratin substance such as skin.
  • Another aspect of the present invention may relate to a use of:
  • composition comprising a continuous phase and dispersed phases wherein the dispersed phase has a size of 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less, the composition comprising
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof, and
  • the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is less than 0.3
  • the weight ratio of (the amount of the (c) second polyglyceryl fatty acid ester)/(the amount of the (b) first polyglyceryl fatty acid ester) is more than 0.01 and less than 0.2
  • the weight ratio of (the amount of the (e) polyol)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second poly glyceryl fatty acid ester) is more than 0.1 and less than 5.
  • Another aspect of the present invention may also relate to a process for preparing a composition comprising a continuous phase and dispersed phases wherein the dispersed phase has a size of 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less, comprising a step of mixing:
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof;
  • the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is less than 0.3
  • the weight ratio of (the amount of the (c) second polyglyceryl fatty acid ester)/(the amount of the (b) first polyglyceryl fatty acid ester) is more than 0.01 and less than 0.2
  • the weight ratio of (the amount of the (e) polyol)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is more than 0.1 and less than 5.
  • the mixing step be performed by a so-called low energy process without a special mechanical stirrer, such as a homogenizer which uses a large amount of energy.
  • the low energy process can be performed by simply gently stirring the ingredients (a) to (f).
  • the above composition in the use and process according to the present invention be in the form of an O/W nano- or micro-emulsion, if the above composition comprises (a) oil.
  • the present invention may also relate to a use of:
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof, and
  • the weight ratio of (the amount of the (a) oil)/(the total amount of the (b) first poly glyceryl fatty acid ester and the (c) second polyglyceiyl fatty acid ester) is less than 0.3
  • the weight ratio of (the amount of the (c) second polyglyceryl fatty acid ester)/(the amount of the (b) first polyglyceryl fatty acid ester) is more than 0.01 and less than 0.2
  • the weight ratio of (the amount of the (e) polyol)/(the total amount of the (b) first polyglyceryl fatty acid ester and the (c) second polyglyceryl fatty acid ester) is more than 0.1 and less than 5, in order to make oil droplets of
  • the present invention may also relate to a process for making oil droplets in an O/W nano- or micro-emulsion comprising
  • hyaluronic acid ingredient selected from the group consisting of hyaluronic acid, hyaluronic acid salts, hyaluronic acid derivatives, hyaluronic acid derivative salts, and mixtures thereof, and
  • water have a particle size of 300 nm or less, preferably 200 nm or less, and more preferably 100 nm or less, comprising a step of adding to the O/W nano- or micro-emulsion or using in the O/W nano- or micro-emulsion
  • compositions according to Example 1 and Comparative Examples 1-3, shown in Table 1 were prepared by mixing the components shown in Table 1.
  • the numerical values for the amounts of the components shown in Table 1 are all based on “% by weight” as raw materials.
  • compositions according to Example 1 and Comparative Examples 1-3 were in the form of an O/W emulsion.
  • AM Active Material NT: Not Tested * 20 kDa to 50 kDa
  • the turbidity of the compositions according to Example 1 and Comparative Example 2 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • composition according to Example 1 was transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Example 1 and Comparative Example 2 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Example 1 show that the use of polyol with 5 or more carbon atoms can provide a transparent composition even if the composition comprises hyaluronic acid or a salt thereof.
  • Comparative Example 1 shows that the use of polyol with less than 5 carbon atoms cannot provide a transparent composition if the composition comprises hyaluronic acid or a salt thereof.
  • Comparative Example 2 corresponds to the formulation according to Example 1 disclosed in WO 2020/110716.
  • Comparative Example 3 shows that the addition of hyaluronic acid or a salt thereof to the formulation according to Example 1 disclosed in WO 2020/110716 cannot provide a transparent composition.
  • compositions according to Examples 2-5 and Comparative Example 4, shown in Table 2 were prepared by mixing the components shown in Table 2.
  • the numerical values for the amounts of the components shown in Table 2 are all based on “% by weight” as raw materials.
  • compositions according to Examples 2-5 and Comparative Example 4 were in the form of an O/W emulsion.
  • AM Active Material NT: Not Tested * 20 kDa to 50 kDa
  • the turbidity of the compositions according to Examples 2-5 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 2-5 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 2-5 and Comparative Example 4 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Examples 2-5 show that the total amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0 and a second polyglyceryl fatty acid ester having an HLB value of less than 11.0 in a composition should be from 0.01% to 5% by weight, relative to the total weight of the composition.
  • Comparative Example 4 shows that if the total amount of the first and second polyglyceryl fatty acid esters in a composition is more than 5% by weight relative to the total weight of the composition, the composition cannot be transparent or slightly translucent.
  • compositions according to Examples 6-7 and Comparative Example 5, shown in Table 3 were prepared by mixing the components shown in Table 3.
  • the numerical values for the amounts of the components shown in Table 3 are all based on “% by weight” as raw materials.
  • composition according to Examples 6 was a composition comprising micelles formed by PG- 4 Caprate and PG-2 Oleate.
  • compositions according to Example 7 and Comparative Example 5 were in the form of an O/W emulsion.
  • Table 3 The compositions according to Example 7 and Comparative Example 5 were in the form of an O/W emulsion.
  • AM Active Material NT: Not Tested * 20 kDa to 50 kDa
  • the turbidity of the compositions according to Examples 6-7 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 6 and 7 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 6-7 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • the droplet size for the composition according to Example 6 means the average size of micelles including no oil in the composition.
  • the droplet size for the composition according to Example 7 means the average size of oil droplets which can be regarded as micelles including the oil in the composition.
  • the droplet size of dispersed phase in the composition according to Comparative Example 5 was not tested because it was opaque.
  • Examples 6-7 show that the weight ratio of (the amount of oil)/(the total amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0 and a second polyglyceryl fatty acid ester having an HLB value of less than 11.0) in a composition should be less than 0.3.
  • Comparative Example 5 shows that if the total amount of the weight ratio of (the amount of oil)/(the total amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0 and a second polyglyceiyl fatty acid ester having an HLB value of less than 11.0) in a composition is 0.3 or more, the composition cannot be transparent or slightly translucent.
  • compositions according to Examples 8-9 and Comparative Examples 6-7, shown in Table 4 were prepared by mixing the components shown in Table 4.
  • the numerical values for the amounts of the components shown in Table 4 are all based on “% by weight” as raw materials.
  • compositions according to Examples 8-9 and Comparative Example 6-7 were in the form of an O/W emulsion.
  • AM Active Material NT: Not Tested * 20 kDa to 50 kDa
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 8 and 9 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 8-9 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Examples 8-9 show that the weight ratio of (the amount of a second polyglyceryl fatty acid ester having an HLB value of less than 11.0)/(the amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0) in a composition should be more than 0.01 and less than 0.2.
  • Comparative Examples 6-7 show that if the weight ratio of (the amount of a second polyglyceryl fatty acid ester having an HLB value of less than 11 ,0)/(the amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0) in a composition is 0.01 or less or 0.2 or more, the composition cannot be transparent or slightly translucent.
  • compositions according to Examples 10-11 and Comparative Examples 8-9, shown in Table 5 were prepared by mixing the components shown in Table 5.
  • the numerical values for the amounts of the components shown in Table 5 are all based on “% by weight” as raw materials.
  • compositions according to Examples 10-11 and Comparative Example 8-9 were in the form of an O/W emulsion.
  • AM Active Material NT: Not Tested * 20 kDa to 50 kDa
  • the turbidity of the compositions according to Examples 10-11 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 10 and 11 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 10-11 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Examples 10-11 show that the weight ratio of (the amount of polyol with 5 or more carbon atoms)/ (the total amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0 and a second polyglyceryl fatty acid ester having an HLB value of less than 11.0) in a composition should be more than 0.1 and less than 5.
  • Comparative Examples 8-9 show that if the weight ratio of (the amount of polyol with 5 or more carbon atoms)/(the total amount of a first polyglyceryl fatty acid ester having an HLB value of more than 11.0 and a second polyglyceryl fatty acid ester having an HLB value of less than 11.0) in a composition is 0.1 or less or 5 or more, the composition cannot be transparent or slightly translucent.
  • compositions according to Examples 12-15 shown in Table 6, were prepared by mixing the components shown in Table 6.
  • the numerical values for the amounts of the components shown in Table 6 are all based on “% by weight” as raw materials.
  • compositions according to Examples 12-15 were in the form of an O/W emulsion.
  • AM Active Material * 20 kDa to 50 kDa ** 1100 kDa
  • the turbidity of the compositions according to Examples 12-15 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The results are shown in Table 6 as “NTU”. The smaller the NTU value is, the more transparent the composition is. The compositions according to Examples 12-14 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 12-15 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Examples 12-15 show that the composition according to the present invention can be transparent or slightly translucent even though it includes a variety of amount of hyaluronic acid or a salt thereof, regardless of the molecular weight of the hyaluronic acid.
  • compositions according to Examples 16-18 and Comparative Example 10, shown in Table 7, were prepared by mixing the components shown in Table 7.
  • the numerical values for the amounts of the components shown in Table 7 are all based on “% by weight” as raw materials.
  • compositions according to Examples 16-18 and Comparative Example 10 were in the form of an O/W emulsion.
  • the turbidity of the compositions according to Examples 16-18 was measured at room temperature by using a turbidimeter (2100Q portable, Hach Company).
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 16-18 were transparent or slightly translucent.
  • the size of dispersed phase in the compositions according to Examples 16-18 was measured with a dynamic light scattering particle size analyzer ELSZ-2000 (Otsuka Electronics Co.Ltd.).
  • Example 16 shows that the type of a polyglyceryl fatty acid ester is not limited.
  • Example 17 shows that the type of polyol with 5 or more carbon atoms is not limited.
  • Example 18 shows that the type of oil is not limited.
  • Comparative Example 10 shows that if polyol with carbon atoms of less than 5 is used in a composition, the composition cannot be transparent or slightly translucent.
  • compositions according to Examples 19-25, shown in Table 8 were prepared by mixing the components shown in Table 8.
  • the numerical values for the amounts of the components shown in Table 8 are all based on “% by weight” as raw materials.
  • compositions according to Examples 19-25 were in the form of an O/W emulsion.
  • NTU The smaller the NTU value is, the more transparent the composition is.
  • compositions according to Examples 19-25 were transparent or slightly translucent.

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Abstract

La présente invention se rapporte à une composition comprenant : (a) au moins une huile facultative; (b) au moins un premier ester d'acide gras de polyglycéryle présentant une valeur HLB supérieure à 11,0; (c) au moins un second ester d'acide gras de polyglycéryle présentant une valeur HLB inférieure à 11,0; (d) au moins un ingrédient formé d'acide hyaluronique, (e) au moins un polyol comportant 5 atomes de carbone ou plus; et (f) de l'eau, dans certaines conditions spécifiques, la composition comprenant une phase continue et des phases dispersées et la phase dispersée présentant une taille inférieure ou égale à 300 nm, de préférence inférieure ou égale à 200 nm et de préférence encore inférieure ou égale à 100 nm. La composition selon la présente invention peut présenter une turbidité inférieure ou égale à 50 uTN, de préférence inférieure ou égale à 30 uTN et de préférence encore inférieure ou égale à 10 uTN.
PCT/JP2022/017975 2021-04-23 2022-04-08 Composition comprenant deux esters d'acide gras de polyglycéryle avec de l'acide hyaluronique WO2022224918A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2021-073311 2021-04-23
JP2021073311A JP2022167493A (ja) 2021-04-23 2021-04-23 ２種のポリグリセリル脂肪酸エステルとヒアルロン酸とを含む組成物
FRFR2105572 2021-05-28
FR2105572A FR3123209B1 (fr) 2021-05-28 2021-05-28 Composition comprenant deux esters de polyglycéryle d’acides gras avec de l’acide hyaluronique

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8242169B2 (en) * 2006-07-04 2012-08-14 Showa Denko K.K. Emulsion composition
FR3029781A1 (fr) * 2014-12-12 2016-06-17 Oreal Composition comprenant de l'hesperetine, une huile, au moins un ester d'acide gras et de (poly)glycerol, un polyol
WO2020110716A1 (fr) 2018-11-27 2020-06-04 L'oreal Composition comprenant deux esters d'acide gras de polyglycéryle
EP3532022B1 (fr) * 2016-10-28 2020-11-25 L'Oreal Composition comprenant au moins deux esters d'acide gras de (poly)glycérol et son utilisation en cosmétique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8242169B2 (en) * 2006-07-04 2012-08-14 Showa Denko K.K. Emulsion composition
FR3029781A1 (fr) * 2014-12-12 2016-06-17 Oreal Composition comprenant de l'hesperetine, une huile, au moins un ester d'acide gras et de (poly)glycerol, un polyol
EP3532022B1 (fr) * 2016-10-28 2020-11-25 L'Oreal Composition comprenant au moins deux esters d'acide gras de (poly)glycérol et son utilisation en cosmétique
WO2020110716A1 (fr) 2018-11-27 2020-06-04 L'oreal Composition comprenant deux esters d'acide gras de polyglycéryle

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Title
SATOSHI TOMOMASA ET AL., OIL CHEMISTRY, vol. 37, no. 11, 1988, pages 48 - 53
WALTER NOLL'S: "Chemistry and Technology of Silicones", 1968, ACADEMIC PRESS

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