WO2023052587A1 - Composition cosmétique comprenant au moins une huile polaire, un polyol et de l'acide ascorbique - Google Patents

Composition cosmétique comprenant au moins une huile polaire, un polyol et de l'acide ascorbique Download PDF

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Publication number
WO2023052587A1
WO2023052587A1 PCT/EP2022/077290 EP2022077290W WO2023052587A1 WO 2023052587 A1 WO2023052587 A1 WO 2023052587A1 EP 2022077290 W EP2022077290 W EP 2022077290W WO 2023052587 A1 WO2023052587 A1 WO 2023052587A1
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weight
composition
respect
total
composition according
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PCT/EP2022/077290
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English (en)
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Sabine VRIGNAUD-BARRETEAU
Pamella WANG
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L'oreal
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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
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • 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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • 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
    • A61Q19/08—Anti-ageing 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

Definitions

  • Cosmetic composition comprising at least one polar oil, a polyol and ascorbic acid
  • the present invention relates to a transparent single-phase cosmetic composition, comprising: a) a maximum content of 6% by weight with respect to the total composition weight of ascorbic acid or one of the derivatives thereof, b) at least one polar oil comprising at least one compound chosen from di-alkyl carbonates, the 2 alkyl chains optionally being identical or different, and mixtures thereof; c) at least one non-volatile additional polar oil, and d) at least one water-miscible organic solvent chosen from polyols having 2 to 20 carbon atoms optionally in a mixture with at least one C2-C6 aliphatic monoalcohol, said composition comprising less than 4% by weight of water with respect to the total weight of the composition, and on the first condition that when the content of ascorbic acid or one of the derivatives thereof is strictly less than 4% by weight with respect to the total composition weight, then the quantity of polar oil b) is less than or equal to the quantity of non-volatile additional polar oil c), and on the
  • the present invention also relates to the cosmetic use of such a composition, as well as a non-therapeutic cosmetic keratin material care method using such a composition.
  • Care effect denotes for example an effect countering the drying or aging of keratin materials and particularly the skin, this care effect being provided by active agents.
  • active agents hydrophilic active agents, and particularly ascorbic acid (vitamin C)
  • vitamin C hydrophilic active agents, and particularly ascorbic acid (vitamin C)
  • this active agent is skin regenerating thanks to stimulation of collagen synthesis responsible for skin firmness, or depigmenting, as this vitamin lowers the production of melanin responsible for brown spots.
  • Ascorbic acid is also known for the antioxidant properties thereof.
  • oily dosage forms are of interest for enhancing the delivery of an active agent for application on keratin materials, preferably the skin, and thus the efficacy thereof, in particular the efficacy thereof for treating skin aging problems. Oily dosage forms are also increasingly sought in the cosmetic field and more specifically in the field of skin care, particularly as they provide nourishment after application.
  • an oily cosmetic composition comprising ascorbic acid or one of the derivatives thereof in a medium comprising specific polar oils and polyols at defined contents, makes it possible to reduce the absorption time thereof after application, while being stable.
  • This composition is rich in oily phase and transparent single-phase.
  • the present invention relates to a transparent single-phase cosmetic composition
  • a transparent single-phase cosmetic composition comprising: a) a maximum content of 6% by weight with respect to the total composition weight of ascorbic acid or one of the derivatives thereof, b) at least one polar oil comprising at least one compound chosen from di-alkyl carbonates, the 2 alkyl chains optionally being identical or different, and mixtures thereof; c) at least one non-volatile additional polar oil, and d) at least one water-miscible organic solvent chosen from polyols having 2 to 20 carbon atoms optionally in a mixture with at least one C2-C6 aliphatic monoalcohol, said composition comprising less than 4% by weight of water with respect to the total weight of the composition, and on the first condition that when the content of ascorbic acid or one of the derivatives thereof is strictly less than 4% by weight with respect to the total composition weight, then the quantity of polar oil b) is less than or equal to the quantity of non-volatile additional
  • composition according to the invention is stable.
  • a composition is referred to as stable when the macroscopic appearance (clearness and homogeneity) does not change after at least 24 hours.
  • the composition according to the invention has a clear and homogeneous appearance.
  • the term "clear” denotes a composition having a transparent appearance.
  • homogeneous denotes a composition consisting of a single phase, in other words single-phase.
  • composition according to the invention is preferably intended for a topical application, particularly on keratin materials, in particular the skin. It particularly comprises a physiologically acceptable medium, i.e., a medium compatible with all keratin materials, in particular the skin.
  • keratin materials denotes the skin and the appendages thereof.
  • skin denotes facial skin and/or body skin, and the scalp.
  • appendages denotes eyelashes, eyebrows, nails and hair, and particularly eyelashes and hair.
  • the present invention also relates to a method of cosmetic treatment of keratin materials, comprising application of a composition according to the invention on said keratin materials. Moreover, the invention also relates to the use of said composition in the cosmetic field, in particular for body or facial skin care.
  • the composition according to the invention comprises less than 5% by weight of surfactant, preferably less than 3% by weight of surfactant, more preferentially less than 2% by weight of surfactant, preferably less than 1% by weight of surfactant with respect to the total weight of the composition.
  • the composition is free from surfactant.
  • surfactant denotes an amphiphilic molecule, i.e., it has two parts of different polarity, in general one is lipophilic (soluble dispersible in an oily phase), the other is hydrophilic (soluble or dispersible in water).
  • surfactants are characterized by the value of the HLB (Hydrophilic Lipophilic Balance) thereof, the HLB being the ratio between the hydrophilic part and the lipophilic part in the molecule.
  • HLB Hydrophilic Lipophilic Balance
  • the term HLB is well known to those skilled in the art and is described for example in "The HLB system. A time-saving guide to Emulsifier Selection” (published by ICI Americas Inc; 1984).
  • the HLB generally ranges from 3 to 8 for the preparation of W/O emulsions and from 8 to 18 for the preparation of O/W emulsions.
  • the HLB of the surfactant(s) used according to the invention can be determined using the GRIFFIN method or the DAVIES method.
  • the composition according to the invention does not comprise emulsifying surfactants such as polyoxyethylenated castor oil, fatty acid and sorbitol and/or sorbitan esters optionally oxyethylenated such as polysorbates, phospholipids, polyethylene glycol and fatty acid esters such as PEG-15 stearate, as well as lecithin.
  • emulsifying surfactants such as polyoxyethylenated castor oil, fatty acid and sorbitol and/or sorbitan esters optionally oxyethylenated such as polysorbates, phospholipids, polyethylene glycol and fatty acid esters such as PEG-15 stearate, as well as lecithin.
  • the composition according to the invention comprises less than 4% by weight of water with respect to the total weight of the composition, preferably less than 3% by weight of water with respect to the total weight of the composition, preferably less than 2% by weight of water with respect to the total weight of the composition, preferably less than 1 .5% by weight of water with respect to the total weight of the composition, preferably less than 1.1 % by weight of water with respect to the total weight of the composition.
  • composition according to the invention differs in particular from emulsions in that it is not presented in the form of a dispersion of two mutually non-miscible liquids at ambient temperature (20-25°C).
  • the composition according to the invention is indeed transparent single-phase. It is single-phase as it has no dispersed phase (also known as discontinuous phase) in droplet form in a dispersing phase (also known as continuous phase).
  • transparent composition denotes according to the present invention a composition with a turbidity value of less than 20 NTU, preferably less than 15 NTU, and preferably less than 10 NTU.
  • the turbidity of the compositions is equal to at least 1 NTU.
  • NTUs are units for measurement of the turbidity of a composition.
  • the turbidity measurement is made, for example, with a model 21 OOP turbidity meter made by the Hach Company, the tubes used for the measurement being references AR397A cat 24347-06.
  • the measurements are made at ambient temperature (from 20°C to 25°C).
  • the composition is transparent and has a turbidity value between 1 and 20 NTU, preferably between 1 and 15 NTU, and preferably less than 10 NTU.
  • composition according to the invention is therefore neither opalescent, turbid, opaque, nor bi-phase.
  • the macroscopic analysis (with the naked eye) of the composition according to the invention shows a transparent and single-phase appearance stable over time at ambient temperature, 4°C and 45°C.
  • composition according to the invention comprises ascorbic acid or one of the derivatives thereof, at a maximum content of 6% by weight with respect to the total composition weight.
  • the ascorbic acid according to the invention corresponds preferably to L-ascorbic acid, or vitamin C. Its structure is as in formula (I): [Chem 1]
  • corbic acid derivative preferably denotes a compound chosen from 5,6-di-O-dimethylsilylascorbate (particularly sold by Exsymol under the reference PRO-AA), DL-alpha-tocopheryl-DL-ascorbyl-phosphate potassium salt also referred to as Potassium Ascorbyl Tocopheryl Phosphate (sold by Senju Pharmaceutical under the reference SEPIVITAL EPC), magnesium ascorbyl phosphate, sodium ascorbyl phosphate (sold by Roche under the reference Stay-C 50), disodium ascorbyl sulfate, sulfinyl-L-ascorbic acid, glucopyranosyl-L-ascorbic acid and ascorbyl glucoside.
  • ascorbyl glucoside denotes the condensation product of glucose, in D form, i.e., in the form of a or p glucopyrannose or a or furanose, or in L form, with ascorbic acid, preferably in L form.
  • the ascorbyl glucoside is L-ascorbic acid 2-O-a-D- glucopyranoside, particularly available from HAYASHIBARA.
  • the ascorbic acid derivative is different from ascorbyl palmitate, and different from ascorbyl tetraisopalmitiate.
  • composition according to the invention comprises ascorbic acid, preferably L-ascorbic acid.
  • the composition preferably comprises at least 0.5% by weight of ascorbic acid or one of the derivatives thereof with respect to the total weight of the composition, preferably at least 1% by weight, more preferably at least 2% by weight.
  • the composition comprises from 0.5% to 6% by weight of ascorbic acid or one of the derivatives thereof, with respect to the total weight of the composition, more preferably from 1% to 6% by weight, even more preferably from 2% to 6% by weight.
  • the quantity of polar oil b) is less than or equal to the quantity of non-volatile additional polar oil c).
  • the quantity of polar oil b) is at most 8% by weight with respect to the total composition weight.
  • the quantity of polar oil b) is between 1 % and 8% by weight with respect to the total composition weight, preferably between 3% and 8% by weight, preferably between 5% and 8% by weight,
  • the composition comprises, as additional polar oil c), at least one fatty alcohol that is liquid at ambient temperature with an unsaturated carbon chain having 12 to 26 carbon atoms, preferably oleic alcohol, in a quantity of at least 3% by weight with respect to the total composition weight.
  • the quantity of additional polar oil c), preferably oleic alcohol is between 3% and 20% by weight with respect to the total composition weight, preferably between 3% and 17% by weight, preferably between 3% and 15% by weight, and
  • the total quantity of polar oils of the composition is less than or equal to 28% by weight with respect to the total composition weight, preferably less than or equal to 27% by weight, preferably less than or equal to 26% by weight.
  • the composition according to the invention preferably comprises a total quantity of polar oils ranging from 5% to 40% by weight, preferably from 7% to 35% by weight, preferably from 8% to 32% by weight with respect to the total weight of the composition.
  • Said polar oil comprises at least one compound chosen from di-alkyl carbonates, the 2 alkyl chains optionally being identical or different, and mixtures thereof (oil b), and at least one non-volatile additional polar oil (oil c).
  • silicon oif' denotes an oil comprising at least one silicon atom, and in particular at least one Si-0 group.
  • hydrocarbon oif' denotes an oil containing essentially hydrogen and carbon atoms and optionally oxygen, nitrogen, sulfur and/or phosphorus atoms.
  • polar oif' for the purposes of this invention, denotes an oil wherein the solubility parameter 8 a at 25°C is different to 0 (J/cm 3 ) 1/2 .
  • polar oif' denotes an oil wherein the chemical structure is essentially formed from, or consists of, carbon and hydrogen atoms, and comprising at least one highly electronegative heteroatom such as an oxygen, nitrogen, silicon or phosphorus atom.
  • - 5D characterizes the LONDON dispersion forces derived from the formation of dipoles induced during molecular shocks
  • - 8 P characterizes the DEBYE interaction forces between permanent dipoles and the KEESOM interaction forces between induced dipoles and permanent dipoles
  • the parameters 8 P , 8 h , 8 D and 8 a are expressed in (MPa) 1/2 , a unit equivalent to (J/cm 3 ) 1/2 .
  • the Hansen solubility parameters are calculated using HSPiP software version V4.1 based on a chemical structure; the method selected in the software is Y-MB or Yamamoto- Molecular Break.
  • the polar oils used according to the present invention have a 8 a between 4 and 9.1 , preferably a 8 a between 4.5 and 9.1 , more preferably between 5 and 8.
  • the polar oil according to the invention comprises at least one compound chosen from di-alkyl carbonates, the 2 alkyl chains optionally being identical or different, and mixtures thereof.
  • the di-alkyl carbonate, the 2 alkyl chains optionally being identical or different is dicaprylyl carbonate, It is particularly marketed under the name Cetiol CC® by Cognis.
  • the composition according to the invention comprises at least dicaprylyl carbonate.
  • composition according to the invention also comprises at least one non-volatile additional polar oil c).
  • non-volatile oil denotes an oil having a vapor pressure less than 0.13 Pa (0.01 mm Hg), at ambient temperature and atmospheric pressure.
  • the non-volatile additional oils can particularly be selected from non-volatile hydrocarbon oils, where applicable fluorinated, and/or silicone oils.
  • non-volatile hydrocarbon additional polar oils suitable for the implementation of the invention, mention can particularly be made of:
  • oils of plant origin such as phytostearyl esters, such as phytostearyl oleate, phytostearyl isostearate and lauroyl/octyldodecyl/phytostearyl glutamate, for example sold under the name ELDEW PS203® by AJINOMOTO, triglycerides consisting of esters of fatty acids and glycerol for which the fatty acids can have chain lengths ranging from CUo C24, with the latter able to be linear or branched, saturated or unsaturated; these oils are particularly heptanoic or octanoic oils, wheat germ, sunflower, grape seed, sesame, corn, apricot, castor, camelina, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy seed, pumpkin, squash, blackcurrant, evening primrose, millet, barley,
  • oils of formula R1COOR2 wherein R1 represents a linear or branched fatty acid residue including 1 to 40 carbon atoms, and R2 represents a hydrocarbon-based chain, particularly a branched chain, including 1 to 40 carbon atoms provided that the sum of R1 and R2 is greater than or equal to 10.
  • the esters can particularly be chosen from esters, particularly fatty acid esters, such as for example cetostearyl octanoate, isopropyl alcohol and C8-C18, preferably C12-C16, fatty acid esters, such as isopropyl palmitate, ethyl palmitate, 2-ethylhexyl palmitate, isopropyl myristate, isopropyl stearate or isostearate, isostearyl isostearate, octyl stearate, hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, diisopropyl adipate, heptanoates, and particularly isostearyl heptanoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, such as propylene glycol dioctanoate, cetyl octanoate, tridec
  • - fatty alcohols that are liquid at ambient temperature, with a branched and/or unsaturated carbon chain having 12 to 26 carbon atoms, preferably 16 to 22 carbon atoms, more preferably 18 to 20 carbon atoms, such as 2-octyldodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, and 2-undecylpentadecanol,
  • - higher fatty acids such as oleic acid, linoleic acid, linolenic acid, and mixtures thereof,
  • non-volatile silicone oils for example non-volatile polydimethylsiloxanes (PDMS), polydimethylsiloxanes comprising alkyl or alkoxy groups which are pendant and/or at the end of the silicone chain, groups each having 2 to 24 carbon atoms, phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes, and (2-phenylethyl)trimethylsiloxysilicates, dimethicones or phenyltrimethicone of viscosity less than or equal to 100 Cst, and
  • PDMS non-volatile polydimethylsiloxanes
  • phenylated silicones such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsil
  • composition according to the invention can also comprise at least one nonvolatile additional polar oil.
  • volatile oil denotes an oil (or nonaqueous medium) liable to evaporate on contact with the skin in less than one hour, at ambient temperature and atmospheric pressure.
  • the volatile oil is a volatile cosmetic oil, liquid at ambient temperature, particularly having a vapor pressure different to zero, at ambient temperature and atmospheric pressure, particularly having a vapor pressure ranging from 0.13 Pa to 40,000 Pa (10 -3 at 300 mm Hg), in particular ranging from 1.3 Pa to 13,000 Pa (0.01 to 100 mm Hg), and preferentially ranging from 1.3 Pa to 1300 Pa (0.01 at 10 mm Hg).
  • volatile silicones such as, for example, volatile linear or cyclic silicone oils, in particular those having a viscosity below or equal to 8 centistokes (8.10 -6 m 2 /s), and having particularly from 2 to 10 silicon atoms, and in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxyl groups having from 1 to 10 carbon atoms.
  • volatile silicone oil that can be used in the invention, mention can be made particularly of dimethicones with a viscosity of 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.
  • Volatile fluorinated oils such as nonafluoromethoxybutane or perfluoromethylcyclopentane and mixtures thereof can also be used. A mixture of the oils cited above can also be used.
  • the non-volatile additional polar oil(s) c) is(are) chosen from fatty alcohols that are liquid at ambient temperature with a branched and/or unsaturated carbon chain having 12 to 26 carbon atoms, preferably 16 to 22 carbon atoms, preferably 18 to 20 carbon atoms, and mixtures thereof.
  • the composition according to the invention comprises at least one nonvolatile additional polar oil c) chosen from fatty alcohols that are liquid at ambient temperature with a branched carbon chain having 12 to 26 carbon atoms, preferably 16 to 22 carbon atoms, preferably 18 to 20 carbon atoms, and at least one non-volatile additional polar oil chosen from fatty alcohols that are liquid at ambient temperature with an unsaturated carbon chain having 12 to 26 carbon atoms, preferably 16 to 22 carbon atoms, preferably 18 to 20 carbon atoms.
  • the composition according to the invention comprises at least one nonvolatile additional polar oil c) chosen from octyldodecanol, oleic alcohol and mixtures thereof.
  • the composition according to the invention comprises dicaprylyl carbonate, and at least one non-volatile additional polar oil c) chosen from fatty alcohols that are liquid at ambient temperature with a branched and/or unsaturated carbon chain having 12 to 26 carbon atoms and mixtures thereof, preferably chosen from octyldodecanol, oleic alcohol and mixtures thereof.
  • the composition according to the invention comprises at least octyldodecanol, and at least oleic alcohol.
  • dicaprylyl carbonate is present at a content of at least 3% by weight, preferably at least 5% by weight with respect to the total composition weight.
  • the additional polar oil(s) chosen from fatty alcohols that are liquid at ambient temperature, with a branched and/or unsaturated carbon chain having 12 to 26 carbon atoms is(are) present in the composition at a concentration between 3% and 40% by weight, preferably between 4% and 35% by weight, preferably between 5% and 30% by weight with respect to the total weight of the composition.
  • composition according to the invention comprises:
  • composition according to the invention can comprise additional fatty substances different from the polar oils cited above, and particularly one or more non-polar oils and/or one or more solid and/or pasty fats.
  • non-polar oil denotes an oil wherein the solubility parameter 8 a at 25 °C as defined above is equal to 0 (J/cm 3 ) 1/2 .
  • non-polar oils mention can be made for example of:
  • Hydrocarbon oils of mineral or synthetic origin such as for example: linear or branched hydrocarbons of mineral or synthetic origin, such as petroleum jelly, polydecenes, hydrogenated polyisobutene such as Parleam, squalane, and mixtures thereof, and in particular hydrogenated polyisobutene.
  • Volatile hydrocarbon oils can be chosen from hydrocarbon oils having 8 to 16 carbon atoms, and particularly branched Cs-C alkanes (also known as isoparaffins) such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane, and for example the oils sold under the trade names Isopars® or Permethyls®; linear alkanes, for example n-dodecane (C12) and n-tetradecane (C14) sold by Sasol respectively under the references PARAFOL 12-97 and PARAFOL 14-97, as well as the mixtures thereof, the undecane-tridecane mixture (Cetiol UT®), the mixtures of n-undecane (C1 1 ) and n-tridecane (C13) obtained in examples 1 and 2 of application W02008/155059 of Cognis and mixtures thereof.
  • the non-polar oil is selected from non-volatile non-polar oils, more preferably the non-polar oil is chosen from hydrocarbon oils of mineral or synthetic origin, in particular linear or branched hydrocarbons, of mineral or synthetic origin.
  • the non-polar oil is squalane or hemisqualane.
  • the composition according to the invention comprises less than 10% by weight of non-polar oil with respect to the total weight of the composition, preferentially less than 6% by weight of non-polar oil, more preferably less than 5% by weight of non-polar oil with respect to the total weight of the composition, or the composition is free from non-polar oil.
  • the other fats which can be present in the composition according to the invention are particularly solid and/or pasty fats.
  • solid fat denotes any fatty substance in solid form at ambient temperature (25°C) and at atmospheric pressure.
  • pasty faf' denotes a lipophilic fat compound having a reversible solid/liquid change of state, having in the solid state, an anisotropic crystalline organization, and comprising at a temperature of 23°C a liquid fraction and a solid fraction.
  • the initial melting point of the pasty fat can be less than 23°C.
  • the liquid fraction of the pasty fat measured at 23°C can represent 9 to 97% by weight of the pasty fat. This liquid fraction at 23°C preferably represents between 15 and 85%, more preferably between 40 and 85% by weight.
  • the melting point is equivalent to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in the standard ISO 11357-3; 1999.
  • the melting point of a pasty fat can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name "MDSC 2920" by TA Instruments.
  • the composition according to the invention comprises less than 3% by weight of solid and/or pasty fats, preferentially less than 2% by weight of solid and/or pasty fats, more preferably less than 1% by weight of solid and/or pasty fats with respect to the total weight of the composition.
  • the composition is free from solid and/or pasty fats.
  • the composition according to the invention also comprises preferably at least 50% by weight with respect to the total weight of the composition of water-miscible organic solvent(s) chosen from polyols having 2 to 20 carbon atoms optionally in a mixture with at least one C2-C6 aliphatic monoalcohol.
  • composition according to the invention comprises at least one polyol having 2 to 20 carbon atoms, said polyol optionally being present with at least one C2-C6 aliphatic monoalcohol.
  • composition according to the invention comprises at least one polyol having 2 to 20 carbon atoms.
  • Said polyol is, preferably, chosen from polyols having 2 to 6 carbon atoms, such as glycerol, diglycerol, propyleneglycol, isoprene glycol, dipropyleneglycol, butylene glycol, hexylene glycol, 1 ,2-propanediol, 1 ,3-propanediol, pentylene glycol, polyethyleneglycols having 2 to 200 ethylene oxide units and mixtures thereof.
  • polyols having 2 to 6 carbon atoms such as glycerol, diglycerol, propyleneglycol, isoprene glycol, dipropyleneglycol, butylene glycol, hexylene glycol, 1 ,2-propanediol, 1 ,3-propanediol, pentylene glycol, polyethyleneglycols having 2 to 200 ethylene oxide units and mixtures thereof.
  • the polyol having 2 to 20 carbon atoms is chosen from 1 ,2-propanediol, dipropylene glycol and mixtures thereof.
  • the composition according to the invention comprises a mixture of polyols having 2 to 20 carbon atoms, and preferably a mixture of 1 ,2-propanediol and dipropylene glycol.
  • the composition comprises from 20% to 95% by weight of polyol(s) having 2 to 20 carbon atoms, with respect to the total weight of the composition, more preferably from 52% to 88% by weight, even more preferably from 53% to 86% by weight.
  • composition according to the invention can comprise at least one C2-C6 aliphatic monoalcohol.
  • said aliphatic monoalcohol comprises 2 to 4 carbon atoms.
  • aliphatic monoalcohol denotes any saturated, linear or branched alkane compound having a single hydroxyl (OH) function.
  • the aliphatic monoalcohol(s) present in the compositions according to the invention can be chosen from ethanol, propanol, butanol, isopropanol, isobutanol or mixtures thereof.
  • the composition according to the invention comprises from 0% to 17% by weight of at least one C2-C6 aliphatic monoalcohol, preferably ethanol, preferably from 0.1 % to 15% by weight.
  • the composition according to the invention comprises at least one polyol having 2 to 20 carbon atoms chosen from dipropylene glycol, 1 ,2-propanediol and mixtures thereof, and optionally at least ethanol.
  • the composition according to the invention has a weight ratio between the oily phase and the hydrophilic phase between 0.1 and 0.9, preferably between 0.1 and 0.7, preferably between 0.1 and 0.6.
  • the oily phase according to the invention comprises the polar oils b) and c) according to the invention, and optionally the other lipophilic compounds.
  • the hydrophilic phase according to the invention comprises the polyol(s) having 2 to 20 carbon atoms, optionally the C2-C6 aliphatic monoalcohol, ascorbic acid, and optionally water.
  • composition can comprise at least one additional hydrophilic active agent different from ascorbic acid and derivatives thereof.
  • hydrophilic active agent denotes a water-soluble or water-dispersible active agent capable of forming hydrogen bonds.
  • composition according to the invention can comprise at least one additional hydrophilic active agent chosen from C-glycoside derivatives of the following general formula (II):
  • - R designates a non-substituted C1-C4, particularly C1-C2, linear alkyl radial, in particular methyl;
  • - S represents a monosaccharide chosen from D-glucose, D-xylose, N-acetyl-D- glucosamine or L-fucose, and in particular D-xylose;
  • - X represents a group chosen from -CO-, -CH(OH)-, -CH(NH 2 )-, and preferentially a -CH(OH)- group; as well the cosmetically acceptable salts thereof, solvates thereof such as hydrates and the optical isomers thereof.
  • C-beta-D-xylopyranoside-2-hydroxy-propane Preferably, C-beta-D-xylopyranoside-2-hydroxy-propane or
  • C-alpha-D-xylopyranoside-2-hydroxy-propane is used, and more preferably C-beta-D-xylopyranoside-2-hydroxy-propane.
  • a C-glycoside of formula (I) suitable for the invention can be advantageously C-beta-D-xylopyranoside-2-hydroxy- propane, of which the INCI name is HYDROXYPROPYL TETRAHYDROPYRANTRIOL particularly sold under the name MEXORYL SBB® or MEXORYL SCN® by CHIMEX.
  • such a C-glycoside is present in concentrated form, i.e., in a hydrophilic dispersion concentrated to 70% with active substance; such a C-glycoside is marketed under the name MEXORYL SCS by NOVEAL.
  • the salts of the C-glycosides of formula (II) suitable for the invention can comprise conventional physiologically acceptable salts of these compounds such as those formed from organic or inorganic acids.
  • mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acids, hydroiodic acid, phosphoric acid and boric acid.
  • the acceptable solvates for the compounds described above comprise conventional solvates such as those formed during the final preparation step of said compounds due to the presence of solvents. By way of example, mention can be made of solvates due to the presence of water or linear or branched alcohols such as ethanol or isopropanol.
  • the C-glycosides (II) are known from the document WO 02/051828.
  • the composition according to the invention comprises a C-glycoside in a quantity between 0.5% and 15% by weight of active substance (C- glycoside) with respect to the total weight of the composition, in particular between 1% and 10% by weight of active substance with respect to the total weight of the composition, more specifically between 2% and 5% by weight of active substance with respect to the total weight of the composition.
  • active substance C- glycoside
  • compositions according to the invention can contain one or more of the usual adjuvants in the cosmetic and dermatological fields, gelling agents and/or lipophilic thickeners; moisturizing agents; emollients; lipophilic active agents; anti-free radical agents; sequestrants; fillers; antioxidants, such as pentaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate; essential oils; perfumes; film-forming agents; soluble dyes; and mixtures thereof.
  • the quantities of these different adjuvants are those conventionally used in the fields in question. In particular, these quantities vary according to the sought purpose and can for example range from 0.01% to 20%, and preferably from 0.1% to 10% by weight of the total weight of the composition.
  • the composition comprises less than 3% by weight of gelling agent and/or lipophilic thickener, preferably less than 2% by weight of gelling agent and/or lipophilic thickener with respect to the total weight of the composition, more preferably, less than 1 % by weight of gelling agent and/or lipophilic thickener with respect to the total weight of the composition.
  • the composition is free from gelling agent and/or lipophilic thickener.
  • composition can further comprise one or more LIV filters, in particular organic filters, particularly liposoluble organic filters.
  • the invention also relates to the cosmetic use of a composition according to the invention for the care of keratin materials, in particular for body and/or facial skin care.
  • the present invention further relates to a non-therapeutic cosmetic care method of keratin materials such as the skin, in particular body and/or facial skin, wherein a composition according to the invention is applied on said keratin materials.
  • composition according to the invention can be obtained conventionally by those skilled in the art.
  • compositions were prepared according to the following method: a) Prepare a pre-dispersion of ascorbic acid (present at 20% active substance in propane- 1 ,2-diol), in polyol and optionally the monoalcohol under magnetic stirring or in a deflocculator until a perfectly homogeneous and clear mixture is obtained and under heating at 85°C; then b) Add the oily phase until a perfectly homogeneous and clear mixture is obtained.
  • compositions according to the invention are in italics, the others are comparative:
  • Formulas 1 , 2, 4, 9, 10, 14, 16, 18, 26, 27, 38, 41 , 52, 53 and 58 comprise 2% by weight of vitamin C.
  • These formulas fulfil the first condition according to the invention (i.e., when the content of ascorbic acid or one of the derivatives thereof is strictly less than 4% by weight with respect to the total composition weight, then the quality of dicaprylyl carbonate (oil b) is less than or equal to the quantity of oleic acid and octyldodecanol (non-volatile additional polar oils c)).
  • Formulas 1 1 , 10067, 10068, 31 and 33 respectively comprise 4%, 4.2%, 4.2%, 6% and 6% by weight of vitamin C.
  • These formulas fulfil the second condition according to the invention (i.e., when the content of ascorbic acid or one of the derivatives thereof is between 4% and 6% by weight with respect to the total composition weight, then (i) the quantity of dicaprylyl carbonate is at most 8% by weight with respect to the total composition weight, (ii) the composition comprises oleic alcohol in a quantity of at least 3% by weight with respect to the total composition weight, and (iii) the total quantity of polar oils of the composition is less than or equal to 28% by weight with respect to the total composition weight).
  • Comparative formula 3 contains no oil c).
  • Comparative formulas 5 to 8, 12, 13, 15, 17, 20, 22 to 25, 28, 29, 39, 40, 43 to 45, 48, 51 , 54, 59 to 64, 10065, 10066, 64-1 , 64-2 and 64-3 comprise a quantity strictly greater than 6% by weight of ascorbic acid.
  • Comparative formulas 19, 30, 32, 35 and 36 comprises 2% by weight of vitamin C. These formulas do not fulfil the first condition according to the invention: the quantity of dicaprylyl carbonate is strictly greater than the quantity of oleic acid and octyldodecanol.
  • Comparative formulas 34, 37, 42, 46, 47, 49, 50, 55, 56, 57 and 10069 comprise a quantity of 4% to 6% of ascorbic acid. These formulas do not fulfil the second condition according to the invention:
  • the quantity of dicaprylyl carbonate is greater than 8% by weight with respect to the total composition weight (formulas 34, 46, 47, 49, 50, 57 and 10069),
  • the composition does not comprise oleic acid (formulas 34, 37, 49, 50, 56 and 57), and/or (i) the total quantity of polar oils of the composition is greater than or equal to 30% by weight with respect to the total composition weight (formulas 42, 46, 47, 49, 50 and 55).
  • compositions obtained was evaluated under stirring, at TO and after 24h, 48h and 1 week, according to the following score:
  • compositions according to the invention are single-phase and transparent at all the times observed.
  • Example 2 Composition according to the invention
  • composition according to the invention was prepared according to the protocol in example 1 : [Table 3]

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Abstract

La présente invention concerne une composition cosmétique à phase unique transparente, comprenant : a) une teneur maximale de 6 % en poids par rapport au poids total de la composition de l'acide ascorbique ou de l'un de ses dérivés, b) au moins une huile polaire comprenant au moins un composé choisi parmi les carbonates de dialkyle, les 2 chaînes alkyle étant éventuellement identiques ou différentes, et leurs mélanges ; c) au moins une huile polaire supplémentaire non volatile, et d) au moins un solvant organique miscible dans l'eau choisi parmi les polyols ayant 2 à 20 atomes de carbone éventuellement en mélange avec au moins un monoalcool aliphatique en C2-C6, dans des conditions spécifiques. La présente invention concerne également l'utilisation cosmétique d'une telle composition, ainsi qu'un procédé cosmétique non thérapeutique de soins des matières kératiniques mettant en œuvre une telle composition.
PCT/EP2022/077290 2021-09-30 2022-09-30 Composition cosmétique comprenant au moins une huile polaire, un polyol et de l'acide ascorbique WO2023052587A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002051828A2 (fr) 2000-12-22 2002-07-04 L'oreal Nouveau derives c-glycosides et utilisation
WO2008155059A2 (fr) 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
CN107233220A (zh) * 2017-07-20 2017-10-10 广州环亚化妆品科技有限公司 一种醇基防晒油及其制备方法
EP3263092A1 (fr) * 2016-07-02 2018-01-03 Estelle Piron Formulation cosmetique comprenant un precurseur liposoluble de silanol et un un ester d'acide gras de vitamine c
WO2021123170A1 (fr) * 2019-12-20 2021-06-24 L'oreal Composition cosmétique comprenant au moins une huile polaire, un monoalcool aliphatique, un mélange de polyols et au moins un principe actif hydrophile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002051828A2 (fr) 2000-12-22 2002-07-04 L'oreal Nouveau derives c-glycosides et utilisation
WO2008155059A2 (fr) 2007-06-19 2008-12-24 Cognis Ip Management Gmbh Mélanges d'hydrocarbures et leur utilisation
EP3263092A1 (fr) * 2016-07-02 2018-01-03 Estelle Piron Formulation cosmetique comprenant un precurseur liposoluble de silanol et un un ester d'acide gras de vitamine c
CN107233220A (zh) * 2017-07-20 2017-10-10 广州环亚化妆品科技有限公司 一种醇基防晒油及其制备方法
WO2021123170A1 (fr) * 2019-12-20 2021-06-24 L'oreal Composition cosmétique comprenant au moins une huile polaire, un monoalcool aliphatique, un mélange de polyols et au moins un principe actif hydrophile

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* Cited by examiner, † Cited by third party
Title
"The HLB system. A time-saving guide to Emulsifier Selection", 1984, ICI AMERICAS INC
C. M. HANSEN: "The three dimensional solubility parameters", J. PAINT TECHNO!, vol. 39, 1967, pages 105

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