WO2011129291A2 - Composition d'émulsion huile dans l'eau - Google Patents

Composition d'émulsion huile dans l'eau Download PDF

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Publication number
WO2011129291A2
WO2011129291A2 PCT/JP2011/058981 JP2011058981W WO2011129291A2 WO 2011129291 A2 WO2011129291 A2 WO 2011129291A2 JP 2011058981 W JP2011058981 W JP 2011058981W WO 2011129291 A2 WO2011129291 A2 WO 2011129291A2
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WO
WIPO (PCT)
Prior art keywords
oil
mass
ultraviolet absorber
water
polyether
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PCT/JP2011/058981
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English (en)
Japanese (ja)
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WO2011129291A3 (fr
Inventor
由布子 永禮
和弘 山口
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株式会社 資生堂
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Publication of WO2011129291A2 publication Critical patent/WO2011129291A2/fr
Publication of WO2011129291A3 publication Critical patent/WO2011129291A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4966—Triazines or their condensed derivatives
    • 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
    • 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

Definitions

  • the present invention relates to an oil-in-water emulsion composition that has a fresh feel at the time of application, is excellent in water resistance after application, and has an oil-soluble ultraviolet absorber blended in an outer phase (water phase) and has a stable and high UV protection ability. .
  • Sunscreen cosmetics are intended to cut the UV rays in the sun and protect the skin from the harmful effects of UV rays.
  • Examples of the base include emulsification type, lotion type, oil type, etc.
  • the oil-in-water emulsification type has a fresh feeling of use and can be formulated from low SPF to high SPF products. Widely used (Non-Patent Document 1).
  • oil-in-water emulsion is excellent in the feeling of use that gives a fresh feel, but has the disadvantage that few water-satisfying products are satisfactory.
  • the oil-in-water type emulsifying base has a problem that when the alcohol is highly blended, the emulsified particles are destroyed, and it is difficult to obtain a sufficiently stable base.
  • Lower alcohol 50% by weight or more, water the following general formula as an emulsifier: (Wherein m is 50 to 1000, n is 1 to 40, a is an integer of 5 to 50, and b is an integer of 5 to 50).
  • An alcohol / oil-in-water emulsified composition characterized by substantially not containing other surfactant as an emulsifier is disclosed, and has the effect of giving gloss, softness and moisture to the hair and improving combing. It is described.
  • the composition described in Patent Document 1 contains a large amount of lower alcohol, it is difficult to apply it to a general skin care base.
  • the ultraviolet-ray scattering agent may be mix
  • the problem in the present invention is an oil-in-water emulsion composition which is stable even when ethanol is highly blended (however, 50% by mass or less) and exhibits excellent water resistance after being applied to the skin, etc. It is an object to provide an oil-in-water emulsified composition containing an oil-soluble ultraviolet absorber having a low viscosity and excellent in feeling of use and ultraviolet protective ability.
  • HLB (Si) 5 to 10 polyether-modified silicone is used as a surfactant, and 5 to 50% by mass of ethanol is blended. Furthermore, by blending a specific amount of a hydrophilic thickener and a polyol into an oil-in-water emulsion, the above problem can be solved by blending an aqueous dispersion of an oil-soluble UV absorber in the aqueous phase.
  • the headline and the present invention were completed.
  • HLB (Si) here is a value obtained by the following calculation formula.
  • the present invention (A) containing an aqueous dispersion of an oil-soluble ultraviolet absorber in an aqueous phase (outer phase); (B) 0.1 to 10% by mass of a polyether-modified silicone having 5 to 10 HLB (Si), (C) 5-50% by weight of ethanol,
  • An oil-in-water emulsion composition comprising (d) 0.01 to 3% by mass of a hydrophilic thickener and (e) 0.1 to 15% by mass of a polyol is provided.
  • the emulsion composition of the present invention is an oil-in-water emulsion containing a large amount of ethanol, a fresh feeling of use can be obtained.
  • the phase is changed to a water-in-oil type as the ethanol evaporates, so that excellent water resistance can be exhibited.
  • the oil-in-water emulsified composition of the present invention was able to improve the stability of the system by blending an ultraviolet absorber that is sparingly soluble in oil into the aqueous phase (outer phase). Further, there is an advantageous effect that the ultraviolet protection ability is improved as compared with the case where the same ultraviolet absorber is blended in the oil phase (inner phase). Therefore, the oil-in-water emulsified composition of the present invention is particularly suitable for use as a sunscreen cosmetic having a fresh feeling of use and excellent UV protection.
  • the oil-in-water emulsion composition of the present invention is characterized by containing an aqueous dispersion (component a) of an oil-soluble ultraviolet absorber in an aqueous phase (outer phase).
  • the oil-soluble UV absorber is not particularly limited, but is preferably selected from UV absorbers that are insoluble in water and hardly soluble in oil. However, substantially insoluble oils such as methylenebisbenzotriazole tetramethylbutylphenol are not included.
  • Examples of the poorly soluble ultraviolet absorber include those described in, for example, JP-A-2009-91307, and specific examples include benzophenone derivatives and triazine derivatives.
  • Oxyphenol methoxyphenyl triazine is preferred.
  • This bisethylhexyloxyphenol methoxyphenyl triazine is commercially available under the trade name of Tinosorb S from BASF, and the commercially available product can be used.
  • the aqueous dispersion of the oil-soluble ultraviolet absorber in the present invention is particularly preferably an aqueous dispersion of composite particles of the oil-soluble ultraviolet absorber and the organic polymer.
  • the oil-soluble ultraviolet absorber is prevented from eluting from the aqueous phase to the oil phase when the water phase containing the water dispersion and the oil coexist.
  • An aqueous dispersion of composite particles of an oil-soluble ultraviolet absorber and an organic polymer can be prepared, for example, according to a method described in WO2009 / 007264.
  • aqueous dispersion in which composite particles of an ultraviolet absorber and an organic polymer are dispersed by emulsion polymerization in a state where the mixture of the ultraviolet absorber and the organic monomer is dispersed in water.
  • organic monomer monomers having an ethylenically unsaturated bond, for example, acrylic acid, methacrylic acid, alkyl acrylate, alkyl methacrylate, styrene monomer, nylon monomer and the like are preferably used.
  • Tinosorb S Aqua includes composite particles of bisethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S) and polymethyl methacrylate (PMMA) dispersed in water, and bisethylhexyloxyphenol methoxyphenyl triazine and PMMA.
  • the content of is 20% by mass and 19% by mass, respectively.
  • the blending amount of the oil-soluble UV absorber in the composition of the present invention is 5% by mass or less, preferably 3% by mass or less, more preferably 0.01 to 3% by mass as a dry mass. If the blending amount is less than 0.01% by mass, sufficient ultraviolet light absorption ability cannot be obtained, and if it exceeds 5% by mass, there is a tendency to cause problems in stickiness. For example, when converted as the amount of the aqueous dispersion (component a) containing 20% by mass of the ultraviolet absorber, the dispersion is 25% by mass or less, preferably 15% by mass or less, more preferably 0.05. It is blended at ⁇ 15% by mass.
  • the polyether-modified silicone (component b) in the oil-in-water emulsion cosmetic of the present invention is selected from those having an HLB (Si) of 5 to 10, preferably 5 to 9.
  • a polyether-modified silicone having a molecular weight of 50,000 or more and a hydrophilic group selected from polyoxyethylene (POE) or polyoxypropylene (POP) is preferably used.
  • a polyether-modified silicone represented by the following formula is preferable.
  • m is 50 to 1000, preferably 150 to 1000, and n is 1 to 40.
  • n is 1 to 40.
  • m: n is preferably 200: 1 to 5: 1, and particularly preferably 60: 1 to 15: 1.
  • a is 5 to 50 and b is 5 to 50, and the content of these polyoxyalkylene groups in the molecule is not particularly limited, but the content of polyoxyalkylene groups exceeds 20% by weight in the total molecular weight. Things are desirable.
  • the polyether-modified silicone represented by the above formula is conventionally used as a surfactant in an oil-in-water emulsion or a water-in-oil emulsion containing 50% or more of ethanol (for example, international Publication No. WO97 / 002888 pamphlet and JP-A-10-306020), and no examples of using this in an oil-in-water emulsion with less alcohol are known.
  • the present invention is the first use of a polyether-modified silicone having an HLB (Si) of 10 or less, preferably 9 or less as a surfactant in an oil-in-water emulsion, and adjusting the blending amount of ethanol to increase the hydrophilic viscosity.
  • the blending amount of the polyether-modified silicone (component b) in the present invention is 0.1 to 10% by mass, preferably 0.1 to 5% by mass, more preferably 0.1 to 3% by mass.
  • the blending amount is less than 0.1% by mass, when it exceeds 10% by mass, a stable oil-in-water emulsion may not be obtained.
  • the emulsified cosmetic of the present invention contains 5% by mass or more of ethanol (component c) as an essential component.
  • the blending amount of ethanol is 5 to 50% by mass, preferably 8 to 50% by mass, more preferably 8 to 40% by mass. If the blending amount is less than 5% by mass or exceeds 50% by mass, a stable oil-in-water emulsion may not be obtained.
  • the emulsified cosmetic of the present invention further contains a hydrophilic thickener (component d) as an essential component.
  • a hydrophilic thickener component d
  • a polyether-modified silicone having an HLB (Si) of 10 or less which has been used in water-in-oil emulsions in the past, is stable by simply changing to a general surfactant for oil-in-water emulsions. It was found that a stable oil-in-water emulsion was formed only by blending 5% by mass or more of ethanol and a hydrophilic thickener.
  • the hydrophilic thickener used in the present invention is not particularly limited as long as it is used in cosmetics. Examples thereof include natural water-soluble polymers, semi-synthetic water-soluble polymers, synthetic water-soluble polymers, and inorganic water-soluble polymers.
  • examples of natural water-soluble polymers include arabia gum, tragacanth gum, galactan, guar gum, carob gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), alge colloid (guckweed extract), starch (rice, corn) , Potato, wheat), plant polymers such as glycyrrhizic acid; microbial polymers such as xanthan gum, dextran, succinoglucan, and bullulan; animal polymers such as collagen, casein, albumin, and gelatin.
  • semi-synthetic water-soluble polymers include starch polymers such as carboxymethyl starch and methylhydroxypropyl starch; methylcellulose, nitrocellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose, carboxy Cellulose polymers such as sodium methylcellulose (CMC), crystalline cellulose and cellulose powder; and alginic acid polymers such as sodium alginate and propylene glycol alginate.
  • starch polymers such as carboxymethyl starch and methylhydroxypropyl starch
  • Cellulose polymers such as sodium methylcellulose (CMC), crystalline cellulose and cellulose powder
  • alginic acid polymers such as sodium alginate and propylene glycol alginate.
  • Examples of synthetic water-soluble polymers include vinyl polymers such as polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, and carboxyvinyl polymer (carbomer); polyoxyethylene polymers such as polyethylene glycol (molecular weight 1500, 4000, 6000). Molecule: Polyoxyethylene polyoxypropylene copolymer copolymer polymer; sodium polyacrylate, polyethyl acrylate, polyacrylamide, acrylic acid / alkyl methacrylate copolymer (trade name “Pemulene TR-1”), etc. Acrylic polymer; polyethyleneimine, cationic polymer and the like.
  • inorganic water-soluble polymer examples include bentonite, AlMg silicate (trade name “Begum”), laponite, hectorite, and silicic anhydride.
  • acrylic polymers such as polyacrylamide (trade name “SEPIGEL 305, SEPPIC”, acrylic acid / alkyl methacrylate copolymer (trade name “Pemulene TR-1, NOVEON”), etc. provide water resistance while giving a fresh feel. It is preferable at the point which is excellent in property.
  • the blending amount of the hydrophilic thickener (component d) in the emulsified cosmetic of the present invention is 0.01 to 3% by mass, preferably 0.05 to 3% by mass, more preferably 0.2 to 1% by mass. is there. When the blending amount is less than 0.01% by mass, a stable emulsion may not be obtained. When the blending amount exceeds 3% by mass, a heavy touch may be caused during application.
  • the emulsified cosmetic of the present invention further contains a polyol (component e) as an essential component.
  • a polyol component e
  • the transparency and stability of the oil-in-water emulsion can be further improved.
  • the stability is maintained even if the amount of alcohol to be blended is reduced, and the alcohol odor of the resulting preparation can be suppressed.
  • the polyol used in the present invention is not particularly limited as long as it is usually used in cosmetics, and examples thereof include dynamite glycerin, 1,3-butylene glycol, dipropylene glycol, and propylene glycol.
  • 1,3-butylene glycol improves stability most effectively.
  • the blending amount of the polyol (component e) in the emulsified cosmetic of the present invention is 0.1 to 15% by mass, preferably 1 to 10% by mass, more preferably 3 to 7% by mass.
  • the blending amount is less than 0.1% by mass, a stable emulsion may not be obtained.
  • the blending amount exceeds 15% by mass, a heavy touch may be caused during application.
  • composition of the present invention may further contain other ultraviolet absorbers in addition to the oil-soluble ultraviolet absorber aqueous dispersion (component a) blended in the aqueous phase.
  • Other ultraviolet absorbers are preferably oil-soluble and soluble in the oil phase (inner phase), and those that absorb ultraviolet rays synergistically with the ultraviolet absorber (component a) present in the aqueous phase are preferred.
  • Such an ultraviolet absorber is not particularly limited, for example, methoxycinnamic acid derivatives, diphenylacrylic acid derivatives, salicylic acid derivatives, paraaminobenzoic acid derivatives, triazine derivatives, benzophenone derivatives, benzalmalonate derivatives, anthranilic derivatives, Examples include imidazoline derivatives, 4,4-diarylbutadiene derivatives, and phenylbenzimidazole derivative systems.
  • 2-ethylhexyl paramethoxycinnamate homosalate
  • octyl salicylate oxybenzone
  • 4-t-butyl-4′-methoxydibenzoylmethane 4-t-butyl-4′-methoxydibenzoylmethane
  • octyl triazone bisethylhexylphenol methoxyphenyl triazine
  • methylene bisbenzotria 2-ethylhexyl paramethoxycinnamate, homosalate, octyl salicylate, oxybenzone, 4-t-butyl-4′-methoxydibenzoylmethane
  • octyl triazone bisethylhexylphenol methoxyphenyl triazine
  • methylene bisbenzotria 2-ethylhexyl paramethoxycinnamate, homosalate, octyl salicylate,
  • the emulsified composition of the present invention contains other components conventionally used in cosmetics in addition to the above-described essential components a to e and optionally other ultraviolet absorbers, as long as the effects of the present invention are not impaired. You may do it. Specific examples include humectants, oils, buffers, chelating agents, preservatives, and the like.
  • the emulsion composition of the present invention can be produced according to a method conventionally used for producing an emulsion. For example, an oil component and HLB (Si) 5 to 10 are added to an aqueous phase component including an aqueous dispersion of an ultraviolet absorber (component a), ethanol (component c), a hydrophilic thickener (component d), and a polyol (component e).
  • the oil-in-water emulsion composition of the present invention can be obtained by adding the oil phase mixed with the polyether-modified silicone (component b) to the aqueous phase while stirring with a homomixer or the like.
  • the oil-in-water emulsified composition of the present invention is fresh and fresh when used, and has a characteristic of forming a film having excellent water resistance after application. Further, a hardly soluble ultraviolet absorber is stably blended in the aqueous phase, and optionally other ultraviolet absorbers are blended. Accordingly, when applied to the skin, a fresh and refreshing feel is obtained, and after application, a water-resistant film is formed on the skin, so that a certain UV protection power is maintained.
  • Example 1 An oil-in-water emulsion composition having the composition listed in Table 1 below was prepared. About the feeling of use of the obtained composition, each female sample was actually applied to the skin by 10 female professional panels, and the feeling of use (no squeaking) was evaluated according to the following criteria. The results are also shown in Table 1. ⁇ : Eight or more people evaluated that there was no squeak. ⁇ : 3 to 7 people evaluated that there was no squeak. ⁇ : Two or less people evaluated that there was no squeak.
  • Example 1 A sample of 18.87 ⁇ L of each composition of Example 1 and Comparative Example 1 was uniformly applied to the surface of a PMMA film (5 cm ⁇ 5 cm) at a rate of 0.75 mg / cm 2 . After leaving for 15 minutes, the absorbance of each sample was measured using a spectrophotometer (U-4100: manufactured by Hitachi, Ltd.). The results are shown in FIG.
  • the liquid oils of Examples 1 and 2 cyclopentasiloxane, ethylhexyl methoxycinnamate, octocrylene
  • a cosmetic comprising an oil-in-water emulsion composition was prepared according to the following formulation.
  • Formulation Example 1 Sunscreen emulsion ion-exchanged water Residual ethyl alcohol 20 Dipropylene glycol 3 Carbomer 0.1 Acrylic acid / alkyl acrylate (C10-30) copolymer 0.1 Polyacrylamide-containing liquid * 1) 0.5 Aminomethylpropanediol appropriate amount polyoxybutylene polyoxypropylene glycol 2 PEG / PPG-19 / 19 Dimethicone 2 Cyclopentasiloxane 2 Hydrogenated polyisobutene 2 Caprylyl methicone 3 Triethylhexanoin 2 2-Ethylhexyl paramethoxycinnamate 3 2-Cyano-3,3-diphenylacrylic acid-2'- Ethylhexyl ester 3 Bisethylhexyloxyphenol methoxyphenyl triazine aqueous
  • Formulation Example 2 Sunscreen emulsion ion-exchanged water Residual ethyl alcohol 20 1,3-butylene glycol 3 Carbomer 0.15 Acrylic acid / alkyl acrylate (C10-30) copolymer 0.15 Aminomethylpropanol appropriate amount polypropylene glycol 3 PEG / PPG-19 / 19 Dimethicone 1.5 Dimethicone 1.5 Cyclopentasiloxane 2 Dimethylpolysiloxane 2 Isododecane 2 Pentaerythrityl tetraethylhexanoate 3 Bisethylhexyloxyphenol methoxyphenyl triazine aqueous dispersion 15 2-methoxyhexyl paramethoxycinnamate 5 4-tert-butyl-4'-methoxydibenzoylmethane 2 Phenylbenzimidazolesulfonic acid 2 2-Hydroxy-4-methoxybenzophenone

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition d'émulsion huile dans l'eau (O/W) qui est stable même lorsqu'elle contient une grande quantité (au plus 50% en masse) d'éthanol, présente d'excellentes propriétés de résistance à l'eau après application sur la peau et analogues, d'excellentes propriétés de protection contre la lumière ultraviolette, et procure une sensation de fraîcheur à l'utilisation. La composition d'émulsion huile dans l'eau se caractérise en ce qu'elle contient: a) une dispersion aqueuse d'un absorbeur de rayons ultraviolets soluble dans l'huile présente dans la phase aqueuse (phase externe); b) entre 0,1 et 10% en masse d'un silicone modifié par polyéther ayant une valeur de la HLB (Si) comprise entre 5 et 10; c) entre 5 et 50% en masse d'éthanol; d) entre 0,01 et 3% en masse d'un agent épaississant hydrophile; et e) entre 0,1 et 15% en masse d'un polyol. Le constituant a) est, de préférence, une dispersion aqueuse d'une particule complexe d'un absorbeur de rayons ultraviolets soluble dans l'huile et d'un polymère organique.
PCT/JP2011/058981 2010-04-13 2011-04-11 Composition d'émulsion huile dans l'eau WO2011129291A2 (fr)

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JP2010092262 2010-04-13
JP2010-092262 2010-04-13
JP2011-086013 2011-04-08
JP2011086013A JP5058353B2 (ja) 2010-04-13 2011-04-08 水中油型乳化組成物

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WO2013081073A1 (fr) * 2011-11-30 2013-06-06 花王株式会社 Cosmétique d'émulsion de type huile dans l'eau
WO2015089035A1 (fr) * 2013-12-09 2015-06-18 Momentive Performance Materials Inc. Compositions pour émulsions et leurs utilisations
JP2018197210A (ja) * 2017-05-24 2018-12-13 キユーピー株式会社 水中油型乳化組成物
CN111050746A (zh) * 2017-09-29 2020-04-21 株式会社资生堂 水包油型乳化化妆品
WO2021177400A1 (fr) * 2020-03-04 2021-09-10 株式会社 資生堂 Composition d'émulsion huile dans eau

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JP2012072085A (ja) * 2010-09-29 2012-04-12 Shiseido Co Ltd 水中油型乳化化粧料
JP2015113297A (ja) * 2013-12-10 2015-06-22 花王株式会社 化粧料組成物
CN106456512B (zh) * 2014-06-30 2019-08-06 株式会社资生堂 水包油型乳化组合物
CN115444785A (zh) * 2014-06-30 2022-12-09 株式会社资生堂 水性化妆品
US9907735B2 (en) 2014-10-21 2018-03-06 Rohto Pharmaceutical Co., Ltd. External composition for skin
JP6602719B2 (ja) * 2016-03-31 2019-11-06 花王株式会社 スキンケア方法
TW202210057A (zh) * 2020-05-25 2022-03-16 日商樂敦製藥股份有限公司 水中油型化妝料
CN115772343B (zh) * 2022-12-02 2024-04-12 江苏德威涂料有限公司 一种水溶性紫外吸收剂及其制备方法和应用

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