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WO2012137940A1 - Composition d'émulsion huile dans l'eau - Google Patents

Composition d'émulsion huile dans l'eau Download PDF

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Publication number
WO2012137940A1
WO2012137940A1 PCT/JP2012/059568 JP2012059568W WO2012137940A1 WO 2012137940 A1 WO2012137940 A1 WO 2012137940A1 JP 2012059568 W JP2012059568 W JP 2012059568W WO 2012137940 A1 WO2012137940 A1 WO 2012137940A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
emulsion composition
component
water emulsion
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/059568
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English (en)
Japanese (ja)
Inventor
武司 村田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of WO2012137940A1 publication Critical patent/WO2012137940A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • 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
    • A61K8/347—Phenols
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention relates to an oil-in-water emulsion composition containing rhododendrol and / or a derivative thereof.
  • rhododendrol and its derivatives are known as ingredients for preventing and improving skin pigmentation such as spots and freckles (see Patent Documents 1 to 3). It has been pointed out that these rhododendrol or derivatives thereof are amphiphilic substances having low solubility in both aqueous bases and oil bases. For this reason, when the emulsion composition is used, rhododendrol or a derivative thereof tends to collect near the interface of the emulsified particles and easily precipitate, so that there is a problem that problems are likely to occur in stability and usability.
  • An object of the present invention is to provide an oil-in-water emulsion composition
  • an oil-in-water emulsion composition comprising the following components (A) to (C).
  • (A) Rhodendrol or a derivative thereof represented by the following general formula (1)
  • R 1 represents a hydrogen atom, an acyl group having 2 to 20 carbon atoms, or a sugar residue of a monosaccharide or a disaccharide.
  • B Propylene glycol mono C 10 -C 26 fatty acid ester
  • C Water-swellable clay mineral
  • the present invention also relates to a method for improving the low temperature stability of an oil-in-water emulsion composition comprising the component (B) and the component (C) in the oil-in-water emulsion composition containing the component (A). Is to provide.
  • the present invention relates to an oil-in-water emulsion composition containing rhododendrol or a derivative thereof, having good low-temperature stability, high skin safety, and excellent whitening effect and feeling of use.
  • the oil-in-water emulsion composition of the present invention contains rhododendrol or a derivative thereof having a melanin production inhibitory effect in a sufficient amount, but has excellent low-temperature stability, high skin safety, whitening effect, It has excellent usability.
  • Rhododendrol or a derivative thereof used in the present invention is represented by the following general formula (1).
  • R 1 represents a hydrogen atom, an acyl group having 2 to 20 carbon atoms, or a sugar residue of a monosaccharide or a disaccharide.
  • Lod Den Dror R 1 is a hydrogen atom [4-(p-hydroxyphenyl) -2-butanol] is a known compound, Acer Maximowiczianum (Acer nikoence Maxim.) It is known that they are included in As the rhododendrol, one synthesized by a conventionally known method may be used, or a megsurinoki extract may be used.
  • a rhododendrol derivative (hereinafter also referred to as acylated rhododendrol) in which R 1 is an acyl group having 2 to 20 carbon atoms is a known compound such as acylation of a phenol compound.
  • R 1 is an acyl group having 2 to 20 carbon atoms
  • acylated rhododendrol a known compound such as acylation of a phenol compound.
  • a saturated or unsaturated aliphatic acyl group is preferable, and an alkanoyl group is more preferable.
  • Specific examples include an acetyl group, a propionyl group, a butyroyl group, an isobutyroyl group, a valeryl group, a hexanoyl group, an octanoyl group, a lauroyl group, a palmitoyl group, and a stearoyl group.
  • an alkanoyl group having 2 to 18 carbon atoms is preferable, an alkanoyl group having 2 to 8 carbon atoms is more preferable, and an alkanoyl group having 2 to 4 carbon atoms is preferable.
  • the group is more preferable, and specific examples of the more preferable acyl group include an acetyl group, a propionyl group, a butyroyl group, and an isobutyroyl group.
  • acylated rhododendrol in the component (A) of the present invention include acetyl rhododendrol, butyroyl rhododendrol, hexanoyl rhododendrol, octanoyl rhododendrol, dodecanoyl rhododendrol, tetradecadolol.
  • Examples include noyl rhododendrol, hexadecanoyl rhododendrol, and octadecanoyl rhododendrol.
  • a rhododendrol derivative (hereinafter also referred to as rhododendrol glycoside) in which R 1 is a sugar residue of a monosaccharide or a disaccharide is a known method (US Patent No. 1). 3201385).
  • rhododendrol glycoside in which R 1 is a sugar residue of a monosaccharide or a disaccharide is a known method (US Patent No. 1). 3201385).
  • the desired glycoside is eliminated by eliminating the acetyl group in the presence of alkali. Can be easily obtained as white powder crystals. It can also be obtained by reducing raspberry ketone glycosides. It is also possible to isolate from natural products.
  • the sugar residue is a reducing monosaccharide or disaccharide, and specific examples include monosaccharides such as glucose, galactose, xylose, mannose, N-acetylglucosamine, and disaccharides such as maltose, cellobiose, and gentibiose. Can do.
  • monosaccharides such as glucose, galactose, xylose, mannose, N-acetylglucosamine
  • disaccharides such as maltose, cellobiose, and gentibiose.
  • isomers having an ⁇ bond and a ⁇ bond there are isomers having an ⁇ bond and a ⁇ bond, and a single or a mixture thereof can also be used.
  • rhododendrol glycosides in the component (A) of the present invention include rhododendrol-D-glucoside ( ⁇ or ⁇ form), rhododendrol-D-galactoside ( ⁇ or ⁇ form), rhododendrol. -D-xyloside ( ⁇ or ⁇ form), rhododendrol-D-maltoside ( ⁇ or ⁇ form) and the like can be mentioned.
  • the component (A) of the present invention has an optical isomer, but the (+) isomer, the ( ⁇ ) isomer alone, or a mixture ( ⁇ ) thereof can also be used.
  • the content of the component (A) in the composition of the present invention is preferably 0.5 to 20% by mass from the viewpoint of obtaining a sufficient effect as a melanin production inhibitor, skin irritation and low temperature stability.
  • the content is 0.5 to 15% by mass, and more preferably 0.5 to 10% by mass.
  • the content in the composition is preferably 0 because the melanin production inhibitory effect is high.
  • the content in the composition is preferably 0.5 to 20% by mass, more preferably 0.5 to 15% by mass, and still more preferably 0.5 to 10% by mass.
  • the (B) propylene glycol monofatty acid ester used in the present invention is a monofatty acid ester having 10 to 26 carbon atoms of fatty acid from the viewpoint of low-temperature stability and feeling of use of rhododendrol or a derivative thereof. Even when a difatty acid ester of propylene glycol or a mono-C 8 fatty acid ester of propylene glycol is blended, an oil-in-water emulsion composition having good stability cannot be obtained.
  • the (B) propylene glycol mono C 10 -C 26 fatty acid ester those represented by the following general formula (2) are preferable.
  • R 2 represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 9 to 25 carbon atoms.
  • the more preferable component (B) used in the present invention a low temperature in view of stability and usability, a straight chain or branched chain of R 2 is a carbon number of 11-23, saturated or unsaturated aliphatic
  • hydrocarbon groups include propylene glycol laurate, propylene glycol myristate, propylene glycol palmitate, propylene glycol stearate, propylene glycol isostearate, propylene glycol oleate, propylene glycol linoleate, linolenic acid
  • Examples include propylene glycol, propylene glycol palmitooleate, and propylene glycol behenate.
  • these 1 type (s) or 2 or more types can be combined suitably and can be used suitably.
  • (B) component used by this invention is a well-known substance, for example, can manufacture easily by esterification of a fatty acid and propylene glycol.
  • it is also commercially available, and as propylene glycol laurate, Sunsoft 25BD sold by Taiyo Kagaku Co., Ltd., as propylene glycol isostearate, cislol PGMIS, propylene glycol oleate sold by Croda.
  • Sunsoft 25 ODV sold by Taiyo Kagaku Co., Ltd. and propylene glycol behenate include Schercemol PGML Ester sold by Novenon.
  • the content of the component (B) in the composition of the present invention is preferably 0.05 to 30% by mass, more preferably 0.05 to 20% from the viewpoints of low-temperature stability, usability, and skin irritation.
  • the mass is more preferably 0.05 to 15 mass%, still more preferably 0.1 to 10 mass%.
  • the content mass ratio (A / B) of the component (A) and the component (B) of the present invention is preferably 0.1 to 10 from the viewpoint of feeling of use (no stickiness, familiar skin) and skin irritation. More preferably, it is from 0.1 to 5, more preferably from 0.2 to 5, even more preferably from 0.2 to 3, and even more preferably from 0.5 to 5.
  • the (C) water-swellable clay mineral used in the present invention is a clay mineral that swells when mixed with water to form a gel, and may be any clay mineral that can be blended in an external preparation for skin, montmorillonite, Smectite clay minerals such as beidellite, nontronite, saponite, hectorite, sauconite, stevensite, clay minerals such as talc and mica, layered silicates such as disilicate, Eilerite, macatite, magadiite, and Kenyaite. These may be used singly or in combination of two or more. These water-swellable clay minerals are preferably used in the form of a dispersion (for example, sol or gel) or a suspension.
  • a dispersion for example, sol or gel
  • a suspension for example, sol or gel
  • smectite clay minerals are preferred, and those having alkali metal or alkaline earth metal ions in the crystal lattice structure can be mentioned.
  • hectorite montmorillonite, nontronite, saponite, beidellite, soconite, and mixtures thereof, and particularly preferred are hectorite, montmorillonite, saponite, and mixtures thereof.
  • These components (C) are generally commercially available, and products containing montmorillonite include Kunipia G, Kunipia F (manufactured by Kunimine Industries), Bentonite W, Bengel (manufactured by Hojun Co.); Veegum T, Veegum HV, Veegum F, Veegum K (manufactured by Vanderbilt); as products containing hectorite, Benton EW, Benton LT (manufactured by Elementis Japan), Hectablite AW, Hectablite 200, Hectablite EW (manufactured by American Colloid) and the like can be mentioned.
  • the content of the component (C) in the composition of the present invention is 0.01 to 10% by mass, more preferably 0.02 to 5% by mass, and still more preferably, from the viewpoint of low-temperature stability, usability, and skin irritation. Is from 0.05 to 5% by weight, even more preferably from 0.05 to 2% by weight, and most preferably from 0.1 to 3% by weight.
  • the content ratio (B / C) of the component (B) and the component (C) of the present invention is preferably 0.03 to 35 from the viewpoints of stability, feeling of use (stickiness, familiarity with skin) and skin irritation. More preferably, it is 0.4 to 35, more preferably 0.5 to 15, more preferably 0.5 to 10, still more preferably 0.5 to 8, and further preferably 1 to 5. is there.
  • (D) monohydric to trihydric alcohol in order to adjust the feeling of use, (D) monohydric to trihydric alcohol can be further contained.
  • the component (D) include monohydric alcohols such as ethanol, propanol, isopropanol, butyl alcohol and the like, and monovalent alcohols such as ethanol, propanol, isopropanol, and butyl alcohol.
  • Divalent alcohols include propylene glycol, 1, Examples of the dihydric alcohol having 2 to 6 carbon atoms such as 2-pentanediol, 1,3-butylene glycol, dipropylene glycol and the like, and examples of the trivalent alcohol include 3 to 6 carbon atoms such as glycerin and isoprene glycol.
  • monohydric alcohols in the present invention, one or more selected from these monovalent to trivalent alcohols can be used in appropriate combination.
  • one or more selected from the group consisting of ethanol, dipropylene glycol, 1,3-butylene glycol and glycerin can be preferably used.
  • the oil-in-water emulsion composition contains about 10% by mass of component (D).
  • the content of the component (D) in the composition of the present invention can be 10% by mass or less from the viewpoints of skin irritation mitigation and feeling of use (tackiness, familiarity with skin). Is preferably 10 to 10% by mass, more preferably 0.1 to 8% by mass, and still more preferably 0.5 to 6% by mass.
  • oil-in-water emulsion composition of the present invention in addition to the above essential components, other components usually blended in pharmaceuticals, quasi-drugs, cosmetics and the like, for example, oil agents, within the range not impairing the effects of the present invention.
  • Oil agents within the range not impairing the effects of the present invention.
  • Moisturizers, thickeners, preservatives, pH adjusters, water, alcohols, drugs, ultraviolet absorbers, ultraviolet scattering agents, dyes, fragrances, and the like can be appropriately blended as necessary.
  • the use of the oil-in-water emulsion composition of the present invention is arbitrary, it can be suitably used for cosmetics, pharmaceuticals, quasi drugs and the like.
  • skin cosmetics such as lotions, milky lotions, beauty creams, base cosmetics, sunscreen cosmetics, packs, massage cosmetics, etc .; can be suitably used as external medicines such as creams containing various drugs.
  • the oil-in-water emulsion composition of the present invention does not have a sticky feeling or a slimy feeling, and therefore can be suitably used as a skin cosmetic.
  • the dosage form of the oil-in-water emulsion composition of the present invention is arbitrary and is prepared as a liquid, emulsion, gel, spray, mousse or the like.
  • An oil-in-water emulsion composition comprising the following components (A) to (C): (A) Rhodendrol or a derivative thereof represented by the following general formula (1)
  • R 1 represents a hydrogen atom, an acyl group having 2 to 20 carbon atoms, or a sugar residue of a monosaccharide or a disaccharide.
  • B Propylene glycol mono C 10 -C 26 fatty acid ester
  • C Water-swellable clay mineral ⁇ 2>
  • R 1 in the general formula (1) is a hydrogen atom, a saturated or unsaturated fat having 2 to 20 carbon atoms ⁇ 1> in water, which is a group acyl group, or a sugar residue of a monosaccharide or a disaccharide, preferably a hydrogen atom, an alkanoyl group having 2 to 18 carbon atoms, or a sugar residue of a monosaccharide or a disaccharide.
  • Oil-type emulsion composition is preferably a hydrogen atom, an alkanoyl group having 2 to 8 carbon atoms, or a sugar residue of glucose, galactose, xylose, mannose, N-acetylglucosamine, maltose, cellobiose or gentaviose.
  • R 1 in the general formula (1) is preferably a hydrogen atom, an alkanoyl group having 2 to 8 carbon atoms, or a sugar residue of glucose, galactose, xylose, mannose, N-acetylglucosamine, maltose, cellobiose or gentaviose.
  • ⁇ 1> or ⁇ 2> of the oil-in-water type more preferably a hydrogen atom, an alkanoyl group having 2 to 4 carbon atoms, or a sugar residue of glucose, galactose, xylose, mannose, N-acetylglucosamine Emulsified composition.
  • the content of the component (A) is 0.5 to 20% by mass, preferably 0.5 to 15% by mass, more preferably 0.5 to 10% by mass, and further preferably 0.5 to 5% by mass.
  • the component (B) is represented by the general formula (2)
  • R 2 represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group having 9 to 25 carbon atoms.
  • Component (B) is propylene glycol laurate, propylene glycol myristate, propylene glycol palmitate, propylene glycol stearate, propylene glycol isostearate, propylene glycol oleate, propylene glycol linoleate, propylene glycol linolenate, palmitate
  • the oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 6>, wherein the emulsion composition is one or more selected from the group consisting of propylene glycol tooleate and propylene glycol behenate.
  • the content of the component (B) is 0.05 to 30% by mass, preferably 0.05 to 20% by mass, more preferably 0.05 to 15% by mass, and further preferably 0.1 to 10% by mass. %, More preferably 0.1 to 5% by mass, the oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 7>.
  • the mass ratio (A / B) of the component (A) to the component (B) is 0.1 to 10, preferably 0.1 to 5, more preferably 0.2 to 5, and still more preferably 0.8.
  • the oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 8> which is 2 to 3, more preferably 0.5 to 5.
  • Component (C) is at least one selected from hectorite, montmorillonite, nontronite, saponite, beidellite and soconite, preferably at least one selected from hectorite, montmorillonite and saponite ⁇ 1
  • the content of ⁇ 11> component (C) is 0.01 to 10% by mass, preferably 0.02 to 5% by mass, more preferably 0.05 to 5% by mass, and still more preferably 0.05 to 2% by mass. %, More preferably 0.1 to 3% by mass, the oil-in-water emulsion composition according to any one of ⁇ 1> to ⁇ 10>.
  • the mass ratio (B / C) of the component (B) to the component (C) is 0.03 to 35, preferably 0.4 to 35, more preferably 0.5 to 15, and still more preferably 0.
  • Oil-in-water emulsion compositions were prepared according to the formulations shown in Table 1-1, 1-2, and Table 2, and the evaluation test was performed. The results are shown in Tables 1-1, 1-2, and Table 2.
  • B Components 10 to 13 and 21 to 22 are mixed, heated to 80 ° C., and mixed with stirring.
  • D After cooling, component 14 is added to C, and further stirred and mixed.
  • Comparative Example 1 containing no component (B) could not maintain room temperature and low temperature stability.
  • Comparative Examples 2 and 5 using propylene glycol caprylate having less than 9 carbon atoms instead of component, and Comparative Examples 3 and 6 using propylene glycol dicaprylate that is not a mono-body are also sufficient in room temperature and low temperature stability.
  • Comparative Examples 4, 7, and 8 containing no component (C) no precipitation was observed, but it was not satisfactory in terms of use such as non-stickiness, moist feeling, and good skin familiarity.
  • the Example of this invention it was excellent in normal temperature and low temperature stability. Since no precipitation occurs, it is expected that a high whitening effect can be obtained even if the amount of component (A) is small.
  • the skin irritation and the feeling in use were evaluated well by using the components (A) to (C) in combination.
  • formulation examples of the oil-in-water emulsion composition of the present invention will be shown. All are expected to have excellent low-temperature stability, high skin safety, and excellent whitening effect and feeling of use.
  • Formulation example 2 (milky lotion) Ingredient Mass% Rhododendrol 1.0 Butyroyl rhododendrol 1.0 Propylene glycol isostearate (trade name: Cisrol PGMIS: manufactured by Croda) 1.0 Montmorillonite 0.4 Dipropylene glycol 3.5 Xanthan gum 0.05 Dimethicone 1.0 1.3-Butylene glycol 3.0 Stearic acid 0.4 Glycerol monostearate 1.2 Behenyl alcohol 0.1 Cholesterol 0.3 Olefin oligomer 8.0 N-stearoyl-L-glutamate sodium 0.5 Soymilk fermentation broth (trade name: Soymilk fermentation broth manufactured by Sansho Pharmaceutical Co., Ltd.) 0.1 Dutch mustard extract 0.1 (Product name: WaterCress-KB made by Silab) Ghetto leaf extract 0.1 (Product name: Moon peach leaf extract BG manufactured by Maruzen Pharmaceutical Co., Ltd.) Seaweed extract (trade name: Seaweed Extract M, manufactured by Maruzen Pharmaceutical

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

Abstract

L'invention concerne un produit cosmétique émulsifié huile dans l'eau contenant du rhododendrol ou un dérivé de celui-ci, qui possède une stabilité élevée à basse température, un degré élevé de sécurité pour la peau et offre une sensation agréable après son utilisation. Ce produit cosmétique émulsifié huile dans l'eau est caractérisé en ce qu'il contient les composants suivants (A-C): (A) du rhododendrol ou un dérivé de celui-ci représenté par la formule générale (1) (dans la formule, R1 représente un atome d'hydrogène, un groupe acyle C2-20, ou une fraction sucre d'un monosaccharide ou d'un disaccharide); (B) ester d'acide gras d'un propylène glycol mono- C10-C26; et (C) un minéral argileux gonflant à l'eau.
PCT/JP2012/059568 2011-04-08 2012-04-06 Composition d'émulsion huile dans l'eau Ceased WO2012137940A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011086672 2011-04-08
JP2011-086672 2011-04-08

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WO2012137940A1 true WO2012137940A1 (fr) 2012-10-11

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TW (1) TW201244745A (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3266442A1 (fr) * 2016-07-04 2018-01-10 Clariant International Ltd Émulsion stabilisée par l'argile

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008031144A (ja) * 2006-06-27 2008-02-14 Kao Corp 美白化粧料
JP2008081491A (ja) * 2006-09-01 2008-04-10 Kao Corp 皮膚外用剤
JP2008273851A (ja) * 2007-04-26 2008-11-13 Kao Corp 皮膚外用剤
WO2009081587A1 (fr) * 2007-12-25 2009-07-02 Kao Corporation Préparation externe pour la peau
JP2010111613A (ja) * 2008-11-05 2010-05-20 Kao Corp 水性美白化粧料
JP2010143848A (ja) * 2008-12-18 2010-07-01 Kao Corp 化粧料

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008031144A (ja) * 2006-06-27 2008-02-14 Kao Corp 美白化粧料
JP2008081491A (ja) * 2006-09-01 2008-04-10 Kao Corp 皮膚外用剤
JP2008273851A (ja) * 2007-04-26 2008-11-13 Kao Corp 皮膚外用剤
WO2009081587A1 (fr) * 2007-12-25 2009-07-02 Kao Corporation Préparation externe pour la peau
JP2010111613A (ja) * 2008-11-05 2010-05-20 Kao Corp 水性美白化粧料
JP2010143848A (ja) * 2008-12-18 2010-07-01 Kao Corp 化粧料

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3266442A1 (fr) * 2016-07-04 2018-01-10 Clariant International Ltd Émulsion stabilisée par l'argile
WO2018007261A1 (fr) * 2016-07-04 2018-01-11 Clariant International Ltd Émulsion stabilisée par de l'argile

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JP2012224624A (ja) 2012-11-15

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