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WO2018012557A1 - Composition de soins solaires e/h comprenant des particules organiques poreuses - Google Patents

Composition de soins solaires e/h comprenant des particules organiques poreuses Download PDF

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Publication number
WO2018012557A1
WO2018012557A1 PCT/JP2017/025465 JP2017025465W WO2018012557A1 WO 2018012557 A1 WO2018012557 A1 WO 2018012557A1 JP 2017025465 W JP2017025465 W JP 2017025465W WO 2018012557 A1 WO2018012557 A1 WO 2018012557A1
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Prior art keywords
oil
composition according
composition
weight
filter
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English (en)
Inventor
Rui Niimi
Ritesh Sinha
Momoko Shimizu
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LOreal SA
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LOreal SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0279—Porous; Hollow
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • the present invention relates to a cosmetic composition, in particular a skin cosmetic composition including organic porous particles, as well as a process for preparing the same and a cosmetic process using the same.
  • UV protecting effect is important for cosmetic compositions, in particular sun care cosmetic compositions for keratinous materials, such as skin.
  • WO 2009/102649 discloses a photoprotective composition comprising one or more photoactive agents, one or more optimizing agents, and a copolymer booster, such as styrene/acrylate copolymer particles having hollow spheres.
  • WO 2010/118415 discloses a UV protecting composition comprising (a) at least one organic UV sunscreen active, (b) at least one semi- crystalline polymer, (c) hollow latex particles, and (d) at least one additional ingredient.
  • WO2014/135360 discloses a photoprotective personal care composition comprising (i) 0.1 to 15% organic sunscreen, (ii) 0.1 to 5% non-ionic surfactant, (iii) 0.1 to 6% hollow
  • WO 2014/203913 discloses a composition comprising, in a physiologically acceptable medium, (a) at least one UV filter, (b) at least one particle having a refractive index of 1.5 or more, and (c) at least one SPF booster selected from hollow particles.
  • sun care compositions comprising porous particles have been reported.
  • WO 2005/016303 discloses an emulsion composition-Tor skin. application comprising an aqueous component, one or more oil ⁇ soluble organic ingredients totalling at least about 15 percent by weight of the composition, and about 1 to about 10 percent by weight of porous silica microspheres.
  • WO 2015/003987 discloses a topical composition comprising a hydrophilic benzimidazole type UVB filter, an organopolysiloxane
  • organic UV filters or inorganic UV filters are formulated in sun care compositions.
  • use of excess amount of organic UV filters in sun care compositions may cause sticky or greasy texture and may increase a concern about skin irritation.
  • use of excess amount of inorganic UV filters in sun care compositions may cause creaky texture and an unnatural whitish effect.
  • the inorganic UV filters are nano particles, there may be concern that these nano particles could penetrate into the skin due to their small size.
  • An objective of the present invention is to provide a composition, preferably a cosmetic composition for a keratin substance, such as skin, which exhibits good UV protecting effects.
  • a composition comprising:
  • the (c) organic porous filler may have an average primary particle size of less than 100 ⁇ , preferably less than 20 ⁇ , and more preferably less than 5 ⁇ .
  • the (c) organic porous filler may have a bulk density of 0.01 g/ml to 0.2 g/ml, preferably about 0.03 g/ml to about 0.15 g/ml, and more preferably about 0.05 g/ml to about 0.1 g/ml.
  • the (c) organic porous filler may be comprised of organic polymer, preferably homopolymer or copolymer having a monomer unit selected from (meth)acrylate, styrene, acrylamide, acrylonitrile, vinyl acetate, ethylene, butadiene, tetrafluoroethylene and divinylbenzene, more preferably organic polymer selected from polystyrene, polyethylene, poly-2-alanine, polytetrafluoroethylene, poly(vinyl acetate), poly(methyl styrene), poly(acrylamide), poly(acrylonitrile), poly( vinyl chloride), polymethacrylate, polyacrylate, polyurethane, silicone resin, nylon, polyorganosiloxane, polysaccharides such as cellulose, copolymer of styrene and Q-C 1 alkyl(meth)acrylate, copolymer of styrene and acrylamide, copolymer of styrene and
  • the (c) organic porous filler may be comprised of organic crosspolymer comprising a monomer unit of Q-C ⁇ alkyl (meth)acrylate and/or bifunctional (meth)acrylate.
  • the amount of the (c) organic porous filler in the composition may be from 0.01 to 20% by weight, preferably from 0.05 to 10% by weight, more preferably from 0.1 to 7% by weight, and even more preferably from 0.5 to 5% by weight relative to the total weight of the.
  • the (a) lipophilic or oil-soluble organic UV filter may be selected from butyl methoxydibenzoylmethane, ethylhexyl methoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene, benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2-(4- diethylamino-2-hydroxybenzoyl)benzoate, 1 , ⁇ -( 1 ,4-piperazinediyl)bis [ 1 - [2- [4- (diethylamino)-2-hydroxybenzoyl]phenyl]-methanone 4-methylbenzylidene camphor, ethylhexyl triazone, bis-ethylhexyloxyphenol methoxyphenyl triazine, diethylhexyl butamido triazone, 2,4,6-tris(dineopen
  • the amount of the (a) lipophilic or oil-soluble organic UV filter in the composition may be from 0.001 to 30% by weight, preferably from 0.01 to 20% by weight, and more preferably from 0.1 to 15% by weight, relative to the total weight of the composition. It is preferable that the (b) hydrophilic or water-soluble organic UV filter may have at least one acid group selected from a carboxylic group, a sulfuric acid, a sulfonic group, a phosphonic group, a phenolic hydroxyl group, and a mixture thereof.
  • the (b) hydrophilic or water-soluble organic UV filter may be selected from terephthalylidene dicamphor sulfonic acid and salts thereof, phenylbenzimidazole sulfonic acid and salts thereof; (+)-10-camphorsulfonic acid and salts thereof, 2-hydroxy-4-methoxybenzophenone- 5 -sulfonic acid and salts thereof, disodium phenyl dibenzimidazole tetrasulfonate and salts thereof, and a mixture thereof.
  • the amount of the (b) hydrophilic or water-soluble organic UV filter in the composition may be from 0.001 to 30% by weight, preferably from 0.01 to 20% by weight, and more preferably from 0.1 to 15% by weight, relative to the total weight of the composition.
  • the composition is a cosmetic composition, preferably a skin cosmetic composition.
  • the composition further comprising at least one oil and is in a form of an W/O emulsion.
  • the present invention also relates to a process for preparing the composition according to the present invention, comprising mixing the (a) at least one lipophilic or oil-soluble organic UV filter, the (b) at least one hydrophilic or water-soluble organic UV filter, and the (c) at least one organic porous filler having an oil absorption capacity equal to or more than 300 mL/lOOg.
  • the present invention also relates to a cosmetic process for a keratinous substance such as skin, comprising applying to the keratin substrate the composition according to the present invention.
  • composition according to the present invention comprises:
  • composition according to the present invention can exhibit improved UV protecting effects.
  • composition according to the present invention includes (a) at least one lipophilic or oil- soluble organic UV filter, (b) at least one hydrophilic or water-soluble organic UV filter, and (c) at least one organic porous filler having an oil absorption capacity equal to or more than 300 mL/lOOg, preferably equal to or more than 400 mL/lOOg, and more preferably equal to or more than 500 mL/1 OOg.
  • composition according to the present invention may be in any form such as a solution, a dispersion, an emulsion, a gel, and a paste.
  • the composition according to the present invention is in the form of an emulsion such as W/O, O/W, W/O/W and 0/W/O, preferably an W/O emulsion.
  • composition according to the present invention is a cosmetic
  • composition in particular a cosmetic sun care composition for a keratin substance such as skin, i.e. skin cosmetic composition.
  • composition according to the present invention comprises (a) at least one lipophilic or oil-soluble organic UV filter. If two or more lipophilic or oil-soluble, organic UV filters are used, they may be the same or different, preferably the same.
  • lipophilic or oil-soluble organic UV filter used herein is understood to mean any agent which screens out UV radiation and which is capable of being completely dissolved in the molecular state in an oil phase or of being dispersed in the colloidal form (for example in the micelle form) in the oil phase.
  • the "lipophilic or oil-soluble organic UV filter” has an oil solubility equal to or more than 0.5g /100 ml isododecane.
  • the (a) lipophilic or oil-soluble organic UV filter used for the present invention may be active in the UV-A and/or UV-B region.
  • the lipophilic or oil-soluble organic UV filter may be hydrophobic or water-insoluble.
  • the (a) lipophilic or oil-soluble organic UV filter may be solid or liquid.
  • the terms “solid” and “liquid” mean solid and liquid, respectively, at 25°C under 1 atm. All kind of lipophilic or oil-soluble organic UV filters can be used in the composition according to the present invention.
  • the (a) lipophilic or oil-soluble organic UV filter can be selected from the group consisting of anthranilic compounds; dibenzoylmethane compounds; cinnamic compounds; salicylic compounds; camphor compounds; benzophenone compounds; ⁇ , ⁇ -diphenylacrylate compounds; triazine compounds; benzotriazole compounds; benzalmalonate compounds; benzimidazole compounds; imidazoline compounds; bis- benzoazolyl compounds; p-aminobenzoic acid (PABA) compounds;
  • PABA p-aminobenzoic acid
  • methylenebis(hydroxyphenylbenzotriazole) compounds methylenebis(hydroxyphenylbenzotriazole) compounds
  • benzoxazole compounds screening polymers and screening silicones
  • dimers derived from a-alkylstyrene 4,4-diarylbutadiene compounds
  • guaiazulene and derivatives thereof rutin and derivatives thereof; and mixtures thereof.
  • Mention may be made, as examples of the (a) lipophilic or oil-soluble organic UV filter(s), of those denoted below under their INCI names, and mixtures thereof.
  • - Anthranilic compounds Menthyl anthranilate, marketed under the trademark "Neo Heliopan MA” by Haarmann and Reimer.
  • Cinnamic compounds Ethylhexyl methoxycinnamate, marketed in particular under the trademark "Parsol MCX" by BASF; isopropyl methoxycinnamate; isopropoxy
  • methoxycinnamate isoamyl methoxycinnamate, marketed under the trademark "Neo
  • Heliopan E 1000 by Haarmann and Reimer; cinoxate (2-ethoxyethyl-4-methoxy cinnamate); DEA methoxycinnamate; diisopropyl methylcinnamate; and glyceryl ethylhexanoate dimethoxycinnamate.
  • - Salicylic compounds Homosalate (homomentyl salicylate), marketed under the trademark “Eusolex HMS” by Rona/EM Industries; ethylhexyl salicylate, marketed under the trademark “Neo Heliopan OS” by Haarmann and Reimer; glycol salicylate; butyloctyl salicylate; phenyl salicylate; dipropyleneglycol salicylate, marketed under the trademark “Dipsal” by Scher; and TEA salicylate, marketed under the trademark "Neo Heliopan TS” by Haarmann and Reimer.
  • benzylidenecamphor derivatives 3-benzylidene camphor, manufactured under the trademark “Mexoryl SD” by Chimex; 4-methylbenzylidene camphor, marketed under the trademark “Eusolex 6300” by Merck; benzylidene camphor sulfonic acid, manufactured under the trademark “Mexoryl SL” by Chimex; camphor benzalkonium methosulfate, manufactured under the trademark "Mexoryl SO” by Chimex; and polyacrylamidomethyl benzylidene camphor, manufactured under the trademark
  • Benzophenone- 1 (2,4-dihydroxybenzophenone), marketed under the trademark "Uvinul 400" by BASF; benzophenone-2 (Tetrahydroxybenzophenone), marketed under the trademark “Uvinul D50” by BASF; Benzophenone-3 (2-hydroxy-4- methoxybenzophenone) or oxybenzone, marketed under the trademark "Uvinul M40" by
  • benzophenone Sulfonate benzophenone-6 (dihydroxy dimethoxy benzophenone); marketed under the trademark "Helisorb 1 1” by Norquay; benzophenone-8, marketed under the trademark "Spectra-Sorb UV-24” by American Cyanamid; benzophenone-9 (Disodium dihydroxy dimethoxy benzophenonedisulfonate), marketed under the trademark "Uvinul DS- 49" by BASF; benzophenone- 12, and n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (UVINUL A+ by BASF).
  • Octocrylene marketed in particular under the trademark "Uvinul N539” by BASF
  • Etocrylene marketed in particular under the trademark "Uvinul
  • Triazine compounds Diethylhexyl butamido triazone, marketed under the trademark “Uvasorb HEB” by Sigma 3V; 2,4,6-tris(dineopentyl 4'-aminobenzalmalonate)-s-triazine, bis- ethylhexyloxyphenol methoxyphenyl triazine marketed under the trademark «TINOSORB S » by CIBA GEIGY, and ethylhexyl triazone marketed under the trademark «UVINUL T150 » by BASF.
  • Benzotriazole compounds in particular, phenylbenzotriazole derivatives: 2-(2H- benzotriazole-2-yl)-6-dodecyl-4-methylpheno, branched and linear; and those described in USP 5240975.
  • polyorganosiloxane comprising benzalmalonate functional groups, such as polysilicone-15, marketed under the trademark "Parsol SLX” by Hoffmann-LaRoche.
  • Benzimidazole compounds in particular, phenylbenzimidazole derivatives.
  • PABA p-aminobenzoic acid
  • ethyl PABA Ethyl dihydroxypropyl PABA
  • pentyl dimethyl PABA ethylhexyl dimethyl PABA
  • glyceryl PABA glyceryl PABA
  • PEG-25 PABA marketed under the trademark "Uvinul P25” by BASF.
  • Drometrizole trisiloxane marketed under the trademark "Silatrizole” by Rhodia Chimie or "Mexoryl XL” by L'Oreal, as represented below.
  • Dimers derived from a-alkylstyrene The dimers described in DE- 19855649.
  • the (a) lipophilic or oil-soluble organic UV filter(s) be selected from the group consisting of:
  • butyl methoxydibenzoylmethane ethylhexyl methoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene, benzophenone-3, benzophenone-4, benzophenone-5, n-hexyl 2-(4- diethylamino-2-hydroxybenzoyl)benzoate, l,l'-(l,4-piperazinediyl)bis[l-[2-[4- (diethylamino)-2-hydroxybenzoyl]phenyl]-methanone 4-methylbenzylidene camphor, ethylhexyl triazone, bis-ethylhexyloxyphenol methoxyphenyl triazine, diethylhexyl butamido triazone, 2,4,6-tris(dineopentyl 4'-aminobenzalmalonate)-s-triazine, 2,4,
  • the amount of the (a) lipophilic or oil-soluble organic UV filter in the composition according to the present invention may be from 0.001 to 30% by weight, preferably from 0.01 to 20% by weight, and more preferably from 0.1 to 15% by weight, relative to the total weight of the composition.
  • composition according to the present invention includes at least one (b) hydrophilic or water-soluble organic UV filter.
  • hydrophilic or water-soluble organic UV filter used herein is understood to mean any agent which screens out UV radiation and which is capable of being completely dissolved in the molecular state in the aqueous phase or of being dispersed in the colloidal form (for example in the micelle form) in the aqueous phase.
  • the "hydrophilic or water-soluble organic UV filter” has an oil solubility equal to or more than 0.5g /100 ml water.
  • the (b) hydrophilic or water-soluble organic UV filter used for the present invention may be active in the UV-A and/or UV-B region.
  • the (b) hydrophilic or water-soluble organic UV filter may be solid or liquid.
  • solid and liquid mean solid and liquid, respectively, at 25°C under 1 atm.
  • hydrophilic or water-soluble organic UV filter There is no limit to the type of the (b) hydrophilic or water-soluble organic UV filter. All kind of hydrophilic or water-soluble organic UV filters can be used in the composition. Two or more different types of hydrophilic or water-soluble organic UV filter may be used in combination. Thus, a single type of hydrophilic or water-soluble organic UV filter or a combination of different types of hydrophilic or water-soluble organic UV filters may be used.
  • the (b) hydrophilic or water-soluble organic UV filter be a non-polymeric acid having two or more pKa values or salt(s) thereof, i.e., a non-polymeric acid having two or more acid dissociation constants or salt(s) thereof.
  • the pKa value is well known to those skilled in the art, and should be determined at a constant temperature such as 25°C.
  • non-polymeric here means that the (b) hydrophilic or water-soluble organic UV filter is not obtained by polymerizing two or more monomers.
  • the hydrophilic or water-soluble organic UV filter does not correspond to an acid obtained by polymerizing two or more monomers such as polycarboxylic acid.
  • the molecular weight of the non-polymeric acid having two or more pKa values or salt(s) thereof be 1000 or less, preferably 800 or less, and more preferably 600 or less.
  • the (b) hydrophilic or water-soluble organic UV filter may be a hydrophilic or water-soluble organic acid or salt(s) thereof.
  • the term "salt” in the present specification means a salt formed by addition of suitable base(s) to the hydrophilic or water-soluble organic UV filter, which may be obtained from a reaction with the hydrophilic or water-soluble organic UV filter with the base(s) according to the methods known to those skilled in the art.
  • the salt mention may be made of metal salts, for example salts with alkaline metal such as Na and a, and salts with alkaline earth metal such as Mg and Ca, and ammonium salts.
  • the (b) hydrophilic or water-soluble organic UV filter may be a monovalent or polyvalent organic acid or salt(s) thereof.
  • the (b) hydrophilic or water-soluble organic UV filter may have at least one acid group selected from the group consisting of a carboxylic group, a sulfuric group, a sulfonic group, a phosphonic group, a phenolic hydroxyl group, and a mixture thereof.
  • the (b) hydrophilic or water-soluble organic UV filter may be selected from the group consisting of dicarboxylic acids, disulfonic acids, and diphosphonic acids, and a mixture thereof.
  • the (b) hydrophilic or water-soluble organic UV filter includes, but is not limited to:
  • terephthalylidene dicamphor sulfonic acid and salts thereof such as manufactured under the name "Mexoryl SX" by Chimex,
  • PABA p-aminobenzoic
  • camphor benzalkonium methosulfate and salts thereof such as manufactured under the name "Mexoryl SO" by Chimex.
  • the (b) hydrophilic or water-soluble organic UV filter may be selected from the group consisting of terephthalylidene dicamphor sulfonic acid and salts thereof,
  • the (b) hydrophilic or water-soluble organic UV filter be selected from the group consisting of terephthalylidene dicamphor sulfonic acid and salts thereof (Mexoryl SX), phenylbenzimidazole sulfonic acid and salts thereof (Eusolex 232), and a mixture thereof.
  • the amount of the (b) hydrophilic or water-soluble organic UV filter in the composition according to the present invention may be from 0.001 to 30% by weight, preferably from 0.01 to 20% by weight, and more preferably from 0.1 to 15% by weight, relative to the total weight of the composition.
  • composition according to the present invention includes (c) at least one organic porous filler.
  • Two or more (c) organic porous fillers may be used in combination.
  • a single type of organic porous filler or a combination of different types of organic porous filler may be used.
  • the (c) organic porous filler of the present invention can have varied shapes, for example the (c) organic porous filler has an oval sphere shape, a nearly sphere shape, a bead shape, or a sphere shape.
  • the (c) organic porous particle of the present invention has a function that absorbs high levels of lipophilic materials, such as oil.
  • the (c) organic porous particle has an oil absorption capacity equal to or more than 300 mL/lOOg, preferably equal to or more than 400 mL/lOOg, and more preferably equal to or more than 500 mL/lOOg.
  • the oil absorption capacity can be measured by a test conforming to "Oil absorption" defined in JIS K 5101.
  • the (c) organic porous filler may have an average primary particle size of less than 100 ⁇ , preferably less than 20 ⁇ , and more preferably less than 5 ⁇ , and even more preferably less than 1 ⁇ .
  • the average primary particle size of the (c) organic porous filler may be generally 0.001 ⁇ or more.
  • the average primary particle size here means a number-average size mean diameter which is given by the statistical particle size distribution to half of the population, referred to as D50.
  • a number-average size mean diameter of the perlite can be measured by a laser diffraction particle size distribution analyzer, such as Mastersizer 2000 by Malvern Corp.
  • the primary particles of the (c) organic porous filler can be associated into agglomerates of sizes in the range of 20 ⁇ to 80 ⁇ in average diameter. These agglomerates are typically called as secondary particles.
  • the (c) organic porous filler may have an average particle size from about 100 ⁇ to 600 ⁇ , preferably from about 200 to 400 ⁇ in a mass.
  • the (c) organic porous filler may have a low bulk density of about 0.01 g/ml to about 0.2 g/ml, preferably about 0.03 g/ml to about 0.15 g/ml, and more preferably about 0.05 g/ml to about 0.1 g/ml.
  • Bulk density can be determined with any methods known in the art. For example, the bulk density can be determined by dividing a weight of filler with its volume (g/ml) after filling the filler in a certain volume of a container.
  • the (c) organic porous filler is typically comprised of organic polymer.
  • the organic polymer may be selected from homopolymer or copolymer having a monomer unit selected from, for example, (meth)acrylate, styrene, acrylamide, acrylonitrile, vinyl acetate, ethylene, butadiene, tetrafluoroethylene, and divinylbenzene.
  • the organic polymer may include, but is not limited to, polystyrene, polyethylene, poly-2-alanine, polytetrafluoroethylene, poly( vinyl acetate), poly(methyl styrene), poly(acrylamide), poly(acrylonitrile), poly(vinyl chloride),
  • the (c) organic porous filler is preferably made of crosspolymer.
  • the crosspolymer is made of two or more different types of monomers.
  • the monomers may be acrylate and/or methacrylate monomers.
  • the (c) organic porous filler is preferably comprised of organic polymer comprising a monomer unit of C
  • the Q- Ci 6 alkyl (meth)acrylate monomer may be preferably a C 8 -C 14 alkyl (meth)acrylate monomer, and more preferably a lauryl (meth)acrylate monomer.
  • the polyfunctional (meth)acrylate is preferably bifunctional (meth)acrylate, and more preferably glycol dimethacrylate, such as ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, and triethyleneglycol dimethacrylate.
  • glycol dimethacrylate such as ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, and triethyleneglycol dimethacrylate.
  • the (c) organic porous filler is composed of lauryl
  • methacrylate/glycol dimethacrylate crosspolymer which is sold under the name "Polytrap® 6603 Adsorber” by AMCOL International Corporation.
  • This filler has an oil absorption capacity of 700 mL/100, an average primary particle size of less than 1 ⁇ , and a bulk density of 0.075 g/ml.
  • the (c) organic porous filler provides a homogeneous oil layer comprising the (a) lipophilic or oil-soluble organic UV filter and a homogeneous, water layer comprising the (b) hydrophilic or water soluble organic UV filter on the keratinous substance(s) after application. It can be assumed that these homogeneous oil and water layers can contribute to improvements of the UV protecting effects of the present composition.
  • composition according to the present invention may comprise the (c) organic porous filler in an amount of from 0.01 to 20% by weight, preferably from 0.05 to 10% by weight, more preferably from 0.1 to 7% by weight, and even more preferably from 0.5 to 5% by weight relative to the total weight of the composition.
  • composition according to the present invention may comprise at least one oil other than the organic UV filter. If two or more oils are used, they may be the same or different.
  • oils means a fatty compound or substance which is in the form of a liquid or a paste (non-solid) 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 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 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 mention may be made of, for example, linseed oil, camellia oil, macadamia nut oil, corn 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.
  • alkane oils such as isododecane and isohexadecane
  • ester oils preferably liquid esters of saturated or unsaturated, linear or branched C ⁇ - C 26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched Q- C 26 aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • the esters of monoalcohols at least one from among the alcohol and the acid from which the esters of the present invention are derived is branched.
  • ethyl palmitate 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 Q-C22 alcohols, and esters of monocarboxylic, dicarboxylic, or tricarboxylic acids and of non-sugar C 4 -C 2 6 dihydroxy, trihydroxy, tetrahydroxy, or pentahydroxy alcohols may also be used.
  • diisopropyl sebacate bis(2-ethylhexyl) sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; bis(2-ethylhexyl) adipate; diisostearyl adipate; bis(2-ethylhexyl) maleate; triisopropyl citrate; triisocetyl citrate; triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sucrose 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.
  • sugars examples 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 -C 30 and preferably C 12 -C 22 fatty acids. If they are unsaturated, these
  • 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 An example that may be mentioned is the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.
  • preferable 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
  • isononanoate ethylhexyl palmitate, isohexyl laurate, hexyl laurate, isocetyl stearate, isopropyl isostearate, isopropyl myristate, isodecyl oleate, glyceryl tri(2-ethylhexanoate),
  • 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).
  • silicone oils mention may be made of, for example, linear
  • organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane,
  • cyclohexasiloxane octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.
  • 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.
  • 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.
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm /s;
  • polydimethylsiloxanes containing dimethylsilanol end groups known under the name dimethiconol (CTFA), such as the oils of the 48 series from the company Rhodia.
  • CTFA dimethiconol
  • silicones containing aryl groups mention may be made of polydiarylsiloxanes, especially polydiphenylsiloxanes and polyalkylarylsiloxanes such as phenyl silicone oil.
  • silicones of the PK series from Bayer such as the product PK20;
  • oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250, and SF 1265.
  • phenyl silicone oil phenyl trimethicone is preferable.
  • 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.
  • Hydrocarbon oils may be chosen from:
  • linear or branched, optionally cyclic, C 6 -C 16 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 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
  • fatty alcohol 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. In at least one embodiment, 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 alcoholj 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 C 6 - C 30 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 C 6 -C 30 fatty alcohols, linear or branched, saturated C 12 -C2o 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 -C 20 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 oil be chosen from hydrocarbon oils, ester oils, silicone oils, and mixtures thereof.
  • the oil be selected from the group consisting of mineral oil, octyldodecanol, petrolatum, isododecane, hydrogenated polyisobutene, isopropyl myristate, isononyl isononanoate, dimethicone, cyclohexasiloxane, C 20-22 alcohol, cetyl palmitate, oleyl alcohol, cetyl alcohol, and mixtures thereof.
  • the amount of the oil in the composition according to the present invention may range from 1 to 50% by weight, preferably from 2 to 40% by weight, and more preferably from 5 to 30% by weight, relative to the total weight of the composition.
  • the oil can form an oil phase of the composition according to the present invention.
  • the oil phase may include the organic UV filter.
  • the amount of the oil phase in the composition according to the present invention may range from 10 to 80% by weight, preferably from 20 to 60% by weight, and more preferably from 30 to 50% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise, in addition to the aforementioned components, components typically employed in cosmetics, specifically, such:, as water, surfactants or emulsifiers, thickeners, cosmetically acceptable hydrophilic organic solvents, inorganic UV filters, silicones and silicone derivatives, natural extracts derived from animals or vegetables, waxes, dyes, swelling agents, penetrating agents, acidifying agents, neutralizing agents, antioxidants, powders, preservatives, fragrances, and the like, within a range which does not impair the effects of the present invention.
  • components typically employed in cosmetics specifically, such:, as water, surfactants or emulsifiers, thickeners, cosmetically acceptable hydrophilic organic solvents, inorganic UV filters, silicones and silicone derivatives, natural extracts derived from animals or vegetables, waxes, dyes, swelling agents, penetrating agents, acidifying agents, neutralizing agents, antioxidants, powders, preservatives, fragrances, and the like, within a range which does not impair
  • the surfactant(s) or emulsifier(s) may be selected from nonionic, anionic, amphoteric, zwitterionic, cationic emulsifiers, and mixtures thereof.
  • emulsifiers include also natural or synthetic polymeric emulsifiers.
  • the surfactant(s) or emulsifier(s) may be selected from nonionic surfactants, especially silicone surfactants, such as PEG- 10 dimethicone and bis-PEG/PPG-14/14 dimethicone.
  • the amount of the surfactant(s) or emulsifier(s) in the composition according to the present invention may be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • the thickener(s) may be preferably selected from silicone elastomers, in particular silicone elastomers in gel form, such as products dimethicone crosspolymers, for example dimethicone crosslinked with C 3 -C 20 alkyl group, and dimethicone/vinyldimethicone crosspolymer and dimethicone (dimethicone/vinyldimethicone crosspolymer swelled with dimethicone).
  • the amount of the thickener(s) in the composition according to the present invention may be from 0.01 to 20% by weight, preferably from 0.1 to 15% by weight, and more preferably from 1 to 10% by weight, relative to the total weight of the composition.
  • the cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower mono-alcohols having from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol, and isobutanol; aromatic alcohols, such asbenzyl alcohol and phenylethyl alcohol; polyols or polyol ethers, such as propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, glycerol, sorbitol, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol ethers, such as propylene glycol monomethylether, diethylene glycol alkyl ethers, such as diethylene glycol
  • monoethylether or monobutylether polyethylene glycols, such as PEG-4, PEG-6, and PEG-8, and their derivatives.
  • the amount of the hydrophilic organic solvent(s) in the composition according to the present invention may be from 1 to 50% by weight, preferably from 2 to 40% by weight, and more preferably from 5 to 30% by weight, relative to the total weight of the composition.
  • the composition according to the present invention may comprise water.
  • the amount of water in the composition according to the present invention may be from 1 to 70% by weight, preferably from 10 to 60% by weight, and more preferably from 25 to 50% by weight, relative to the total weight of the composition.
  • the neutralizing agent(s) may be selected from inorganic or organic alkaline agents, preferably organic alkaline agents, such as basic amino acids, monoethanolamine,
  • the amount of the neutralizing agent(s) in the composition according to the present invention may be from 0.01 to 10% by weight, preferably from 0.05 to 8% by weight, and more preferably from 0.1 to 5% by weight, relative to the total weight of the composition.
  • the preservative(s) may be selected from, for example, phenoxyethanol, phenoxypropanol, caprylyl glycol, resorcinol, and the like.
  • the amount of the preservative(s) in the composition according to the present invention may be from 0.001 to 10% by weight, preferably from 0.01 to 5% 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 may comprise the above optional additive(s) in an amount of from 0.01 to 80% by weight, preferably from 0.05 to 70% by weight, and more preferably from 0.1 to 60% by weight, relative to the total weight of the composition.
  • the composition can be formulated in a lotion, a milky lotion, a cream, a gel, a paste, a serum, foam, or spray.
  • the composition preferably exhibits a pH which respects the skin and which generally ranges from 3 to 9 and preferably from 4 to 8, and more preferably from 5 to 8.
  • the composition according to the present invention may be intended to be used as a cosmetic topical composition.
  • the composition according to the present invention may be intended for application onto a keratin substance.
  • Keratin substance here means a material containing keratin as a main constituent element, and examples thereof include the skin, scalp, nails, lips, hair, and the like.
  • the composition according to the present invention be used for a cosmetic process for the keratin substance, in particular skin.
  • the cosmetic composition according to the present invention may be a skin cosmetic composition, preferably a skin sun care composition for protecting skin from UV rays.
  • composition according to the present invention can be prepared by mixing the above essential and optional ingredients at appropriate temperature in accordance with any of the processes which are well known to those skilled in the art.
  • the processes which are well known to those skilled in the art.
  • composition in a form of an W/O emulsion of the present invention can be manufactured the following protocol: (1) mixing an oily ingredients comprising the (a) lipophilic or oil-soluble organic UV filter with the (c) organic porous filler and then stirring them until the (c) organic porous filler becomes well dispersed to prepare an oil phase, (2) preparing a water phase by mixing aqueous ingredients comprising the (b) hydrophilic or water-soluble organic UV filter, and (3) adding or pouring the water phase into the oil phase while stirring the oil phase.
  • the composition according to the present invention may preferably be used as a cosmetic composition, in particular a sun care cosmetic composition for a keratinous substance such as skin to protect the keratinous substance from UV rays.
  • the cosmetic process here means non-therapeutic cosmetic method for protecting the surface of a keratin substrate such as skin from UV rays.
  • the composition according to the present invention may be intended for application onto a keratin substance such as the skin, the scalp and/or the lips, preferably the skin.
  • the composition according to the present invention can be used for a cosmetic process for the skin.
  • the present invention relates to a process, preferably a cosmetic process for protecting the skin from UV rays, comprising the step of applying onto the skin the composition according to the present invention. Since the composition according to the present invention has improved UV protecting effect, the cosmetic process according to the present invention can protect keratin substrate such as skin from UV rays, thereby limiting the darkening of the skin, improving the color and uniformity of the complexion, and/or treating aging of the skin.
  • Example 1 and Comparative Examples 1 to 8 The compositions according to Example 1 and Comparative Examples 1 to 8 were prepared in accordance with the following preparation protocol:
  • terephthalylidene dicamphor sulfonic acid (“Mexoryl SX" from Chimex) triethanolamine, butylene glycol, glycerine, phenoxy ethanol, caprylyl glycol, and ethanol
  • Methyl Metacrylate Crosspolymer an organic porous filler, 140 mL/lOOg of an oil absorption capacity
  • Silica Silylate an inorganic porous filler, 1040 mL/lOOg of an oil absorption capacity
  • Silica an inorganic porous filler, 200 mL/lOOg of an oil absorption capacity
  • In-vitro SPF measurements for all samples were carried out as below.
  • the sample for SPF value measurement was prepared by placing 30 mg of each of the compositions on a plate (Helio plate HD 6, PMMA, 50 mm x 50 mm) like dots, then spreading evenly with a finger over the plate. After drying it for 20 minutes, the in vitro SPF value was calculated from the UV absorbance data, which was measured with a UV spectrophotometer (UV-2000S,
  • composition according to Example 1 showed good UV protecting properties.
  • composition according to Comparative Example 1 which did not include any organic porous filler, showed poor UV protecting properties.
  • composition according to Comparative Example 2 which did not include any hydrophilic or water-soluble organic UV filter, also showed poor UV protecting properties.
  • compositions according to Comparative Examples 4 to 8 which includes the organic porous filler having 250 mL/1 OOg of the oil absorption capacity (Comparative Example 4), the organic porous filler having 140 mL/1 OOg of the oil absorption capacity (Comparative Example 5), the inorganic porous fillers (Comparative Examples 6 and 7), or the hollow organic filler (Comparative Example 8), instead of the organic porous filler of the present invention, exhibit poor UV protecting effects.
  • the combination of the lipophilic or oil-soluble organic UV filter, the hydrophilic or water-soluble organic UV filter, and the organic porous filler of the present invention enables to provide improved UV protecting effects. Therefore, the composition according to the present invention can be used in a sun care cosmetic composition for a keratinous substance such as skin to protect the keratinous substance from UV rays, even if a large amount of organic UV filters and/or in organic UV filters is not formulated.

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Abstract

La présente invention concerne une préparation comprenant : (a) au moins un filtre UV organique lipophile ou oléosoluble, (b) au moins un filtre UV organique hydrophile ou hydrosoluble, et (c) au moins une charge poreuse organique ayant une capacité d'absorption d'huile égale ou supérieure à 300 mL/100 g, de préférence égale ou supérieure à 400 mL/100 g, et idéalement supérieure ou égale à 500 mL/100 g. La composition selon la présente invention présente des effets améliorés de protection UV.
PCT/JP2017/025465 2016-07-14 2017-07-05 Composition de soins solaires e/h comprenant des particules organiques poreuses Ceased WO2018012557A1 (fr)

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EP3946642A4 (fr) * 2019-02-15 2023-05-17 ISP Investments LLC Compositions d'écran solaire et procédé d'utilisation de celui-ci
WO2023094277A1 (fr) * 2021-11-26 2023-06-01 L'oreal Émulsion cosmétique eau-dans-huile comprenant un filtre uv spécifique soluble dans l'eau, une base, une huile volatile, un polymère filmogène hydrophobe, un polydiméthylméthylsiloxane linéaire polyoxyalkyléné et une vitamine b3
US20240366484A1 (en) * 2021-09-02 2024-11-07 Conopeo, Inc, d/b/a UNILEVER A photoprotective personal care composition

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JP7624869B2 (ja) * 2020-04-30 2025-01-31 株式会社ファンケル 油中水型乳化化粧料
JP2022061048A (ja) * 2020-09-25 2022-04-18 ロレアル 非ポリマー性化合物を含む液滴を使用する方法
JP2025109698A (ja) * 2024-01-12 2025-07-25 花王株式会社 皮膚化粧料

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