WO2020262152A1 - Agent de pulvérisation pour nettoyer la peau - Google Patents

Agent de pulvérisation pour nettoyer la peau Download PDF

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Publication number
WO2020262152A1
WO2020262152A1 PCT/JP2020/023779 JP2020023779W WO2020262152A1 WO 2020262152 A1 WO2020262152 A1 WO 2020262152A1 JP 2020023779 W JP2020023779 W JP 2020023779W WO 2020262152 A1 WO2020262152 A1 WO 2020262152A1
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Prior art keywords
skin
acid
spray
skin cleansing
spray agent
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PCT/JP2020/023779
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English (en)
Japanese (ja)
Inventor
航平 山本
翔子 伊庭
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小林製薬株式会社
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Priority to CN202080003386.5A priority Critical patent/CN112449590A/zh
Publication of WO2020262152A1 publication Critical patent/WO2020262152A1/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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/55—Phosphorus compounds
    • 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
    • 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
    • A61K8/86—Polyethers
    • 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
    • A61Q19/004—Aftersun preparations
    • 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
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the present invention relates to a skin cleansing spray agent used by directly spraying it on the skin.
  • Various skin cleansing compositions such as facial cleansers, body soaps, and shampoos are provided as products aimed at cleaning the skin and keeping the skin clean.
  • the surfactant adsorbs to the dirt to reduce the surface tension between the dirt and water, and the mechanical force due to friction causes the dirt to float in the water.
  • it is necessary to add a surfactant at a critical micelle concentration or higher.
  • Patent Document 1 describes a liquid skin cleaning agent product comprising a former container and a liquid skin cleaning agent composition filled in the former container, wherein the liquid skin cleaning agent composition is (1).
  • Liquid skin containing the copolymer of (C) and (C) sugar alcohol, and the mass ratio (A) / (B) of the content of the component (A) to the content of the component (B) is 20 to 250.
  • Cleaning agent products are disclosed.
  • Patent Document 2 states that (a) fatty acid salt is 2 to 9% by mass, (b) betaine lauryldimethylaminoacetate is 0.5 to 4% by mass, and (c) one or more dihydric alcohols.
  • a skin cleaning agent composition which comprises filling a former container with a cleaning agent having a / (a) of 0.1 to 0.5.
  • Patent Document 3 describes a former container containing (a) betaine lauryldimethylaminoacetate and (b) 4 to 15% by mass of a higher fatty acid soap having a specific composition and formed from a fatty acid having 5 to 25 carbon atoms. The cleaning agent composition discharged in the above is disclosed.
  • the skin after sunburn is inflamed, which can be said to be a kind of burn, and the barrier function and water retention ability are lower than those of normal skin.
  • the affected area is cooled with water or ice, and an anti-inflammatory agent is applied.
  • Patent Document 4 describes that a composition containing a coolant dissolved in a solvent containing (R) -1,2-propanediol is used for treating the skin after sunburn.
  • 5 describes the use of certain hydrated hemitatelate benzimidazol-2-ylpyrimidine compounds for the treatment of post-tanned skin.
  • the pumpformer-type skin cleansing composition contains a relatively small amount of surfactant, and in that respect, irritation to the skin is reduced as compared with the solid or semi-solid skin cleansing composition. It is thought that there is a tendency to be. On the other hand, since it is a major premise that the pump former type skin cleansing composition is discharged in the form of foam, the minimum amount of surfactant necessary for exerting the foaming force is blended. That is inevitable due to its composition.
  • an object of the present invention is to provide a skin cleansing composition that can be used in a method different from the conventional method and can impart a comfortable cooling sensation.
  • the present inventor has come up with the idea of a novel application in which the skin cleansing composition is directly sprayed onto the skin without foaming in advance when applied to the skin in order to further reduce irritation to the skin. .. It was also found that by coexisting an amphipathic ester with a surfactant, detergency can be effectively obtained without foaming in advance, and a comfortable cooling sensation can be imparted by further blending a cooling sensation component. The present invention has been completed by further studies based on this finding.
  • Item 1 A skin cleansing spray agent containing (A) a surfactant, (B) an amphipathic ester, and (C) a cooling sensation component, and contained in a spray container.
  • Item 2. Item 2. The spray agent for skin cleaning according to Item 1, wherein the spray container is a pump type spray container.
  • Item 3. Item 2. The spray agent for skin cleaning according to Item 1, wherein the spray container is an aerosol spray container.
  • the skin cleaning spray agent according to any one of. Item 5.
  • Item 7. Item 2. The skin cleansing spray agent according to any one of Items 1 to 6, wherein the content of the component (A) is 0.025 to 0.9% by weight.
  • Item 8. Item 2. The skin cleansing spray agent according to any one of Items 1 to 7, wherein the component (C) is menthol and / or menthol succinate.
  • Item 9. Item 2. The skin cleansing spray agent according to any one of Items 1 to 8, wherein the content of the component (C) is 0.001 to 0.5% by weight.
  • Item 10. Item 2. The skin cleansing spray agent according to any one of Items 1 to 9, which is applied to the skin after sunburn.
  • the skin cleansing composition can exhibit excellent cleansing power while reducing the skin irritation, it is different from the conventional use of foaming in advance when applied to the skin, and directly on the skin. It is possible to provide a new application of spraying and applying a cleansing composition onto the skin. Since it can be washed without foaming in advance, the blending amount of the surfactant in the skin cleansing liquid composition can be significantly reduced as compared with the blending amount contained in the conventional skin cleansing liquid composition. It is also possible to further reduce skin irritation. In addition, since it is possible to give a comfortable cooling sensation while reducing skin irritation, inflammation causes a decrease in barrier function and water retention ability, resulting in hypersensitivity and burning, as in the case of sunburned skin. It can be suitably used for cleaning the skin.
  • the skin cleansing spray agent of the present invention may be referred to as (A) surfactant (hereinafter, may be referred to as (A) component) and (B) amphipathic ester (hereinafter, may be referred to as (B) component). It is characterized in that it contains (a) and (C) a cooling sensation component (hereinafter, may be referred to as (C) component) and is housed in a spray-type container.
  • A surfactant
  • B amphipathic ester
  • the skin cleansing spray agent of the present invention contains a surfactant as the component (A).
  • the surfactant is not particularly limited, but preferably an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a natural surfactant and the like can be mentioned from the viewpoint of suppressing irritation to the skin.
  • the surfactant one of anionic surfactant, nonionic surfactant, amphoteric surfactant, and natural surfactant may be used alone, or two or more thereof may be arbitrarily combined. May be used.
  • anionic surfactant used in the present invention examples include carboxylic acid type, sulfonic acid type, sulfate ester type, and phosphoric acid ester type surfactants.
  • carboxylic acid type surfactant examples include saturated or unsaturated amino acids having 6 to 22 carbon atoms such as octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, and stearic acid; octanoyl groups and decanoyles.
  • Examples include N-acylamino acids (carboxylic acid type amino acid-based anionic surfactants) having saturated or unsaturated N-acyl groups having 8 to 24 carbon atoms such as groups, lauroyl groups, myristic groups, palmitoyl groups, and cocoyl groups. Be done.
  • N-acyl amino acid in the carboxylic acid type amino acid-based anionic surfactant examples include N-acylsarcosine, N-acylaspartic acid, N-acylglutamic acid, lauroylmethyl- ⁇ -alanine and the like. More specific carboxylic acid-type amino acid-based anionic surfactants include N-lauroyl sarcosine, N-lauroyl aspartic acid, cocoyl glutamic acid, and lauroyl methyl- ⁇ -alanine sodium.
  • sulfonic acid type surfactant examples include an ester of a fatty acid having 6 to 22 carbon atoms such as cocoyl isethionic acid and isethionic acid; hexanesulfonic acid, octanesulfonic acid, decanesulfonic acid, dodecanesulfonic acid and the like.
  • Examples thereof include N-acyl-N-methyltaurin (sulfonic acid type amino acid-based anionic surfactant) having a saturated or unsaturated N-acyl group of No. 8 to 24. More specific sulfonic acid-type amino acid-based anionic surfactants include N-myristoyl-N-methyltaurine, N-lauroylmethyltaurine, cocoylmethyltaurine and the like.
  • sulfuric acid ester-type surfactant examples include esters of saturated or unsaturated fatty acids having 10 to 22 carbon atoms such as lauryl sulfate and myristyl sulfate and sulfuric acid.
  • phosphoric acid ester-type surfactant examples include esters of saturated or unsaturated fatty acids having 8 to 24 carbon atoms such as lauryl phosphate and phosphoric acid.
  • anionic surfactants may be in the form of salts, for example, alkali metal salts such as sodium salt and potassium salt; triethanolamine (TEA) salt; ammonium salt and the like. it can.
  • alkali metal salts such as sodium salt and potassium salt
  • TAA triethanolamine
  • ammonium salt and the like it can.
  • a carboxylic acid type surfactant and a sulfonic acid type surfactant are preferably mentioned, and more preferably, from the viewpoint of obtaining better skin irritation reducing property and detergency.
  • Lauric acid, N-lauroyl aspartic acid, cocoyl glutamic acid, cocoyl methyl taurine and salts thereof are mentioned, and more preferably, sodium laurate, sodium N-lauroyl aspartate, cocoyl glutamate triethanolamine, sodium cocoyl methyl taurine are mentioned. Be done.
  • These salts are mentioned, more preferably cocoyl glutamic acid, cocoyl methyl taurine and salts thereof, further preferably cocoyl glutamic acid triethanolamine, cocoyl methyl taurine sodium, and even better detergency is obtained.
  • N-acylaspartic acid having a saturated or unsaturated acyl group having 8 to 24 carbon atoms is preferable, N-lauroyl aspartic acid is more preferable, and sodium N-lauroyl aspartate is more preferable.
  • N-acylaspartic acid having a saturated or unsaturated acyl group having 8 to 24 carbon atoms is preferable, N-lauroyl aspartic acid is more preferable, and sodium N-lauroyl aspartate is more preferable.
  • anionic surfactants may be used alone or in combination of two or more.
  • nonionic surfactant used in the present invention examples include ester-type, ether-type, ester-ether-type, alkanolamide-type, alkylglycoside-type, and alcohol-type surfactants.
  • ester-type surfactant examples include glycols dilaurate, glycol monostearate, glycol distearate, glyceryl monolaurate, glyceryl dilaurate, glyceryl monostearate, and glyceryl distearate, which have 8 to 20 carbon atoms.
  • ether-type surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene polyoxypropylene glycol.
  • ester-ether type surfactant examples include polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene hexitan fatty acid ester, and sorbitan fatty acid ester polyethylene glycol.
  • alkanolamide type surfactant examples include cocamide DEA (coconut oil fatty acid diethanolamide), lauric acid diethanolamide, oleic acid diethanolamide, stearic acid diethanolamide and the like.
  • alkyl glucoside type surfactant examples include octyl glucoside, decyl glucoside, and lauryl glucoside.
  • alcohol-type surfactants examples include cetanol, stearyl alcohol, and oleyl alcohol.
  • ester-ether type surfactants and alkanolamide type surfactants are preferable from the viewpoint of obtaining better skin irritation reducing property and detergency.
  • Preferred are polyoxyethylene cured castor oil and cocamide DEA, and more preferably polyoxyethylene cured castor oil.
  • nonionic surfactants may be used alone or in combination of two or more.
  • amphoteric surfactant used in the present invention examples include alkyl betaine type, fatty acid amide propyl betaine type, amine oxide type and other surfactants.
  • alkyl betaine type surfactant examples include lauryldimethylaminoacetic acid betaine, stearyldimethylaminoacetic acid betaine, octadecylaminomethyldimethylsulfopropyl betaine and the like.
  • fatty acid amide propyl betaine type amphoteric tenside agent examples include amide betaine (amino acid-based amphoteric tenside agent) such as cocamidopropyl betaine, and sulfobetaine such as cocamidopropyl hydroxysultaine.
  • amine oxide type amphoteric surfactant examples include lauryldimethylamine N-oxide and oleyldimethylamine N-oxide.
  • amphoteric tenside agents may be in the form of salts, for example, alkali metal salts such as sodium salt and potassium salt; triethanolamine (TEA) salt; ammonium salt and the like. ..
  • amphoteric surfactants fatty acid amide propyl betaine type surfactants are preferable, and amide betaines such as cocamidopropyl betaine are more preferable, from the viewpoint of obtaining better skin irritation reduction property and detergency.
  • Amino acid-based amphoteric surfactant and more preferably cocamidopropyl betaine.
  • amphoteric surfactants may be used alone or in combination of two or more.
  • Natural surfactants used in the present invention include lecithin and lysolecithin; saponins such as Kiraya saponin, soybean saponin, yukka saponin, enju saponin, beet saponin, azuxaponin, carrot saponin, tea species saponin, hechimasaponin, and tsubokusaponin. And so on.
  • saponins such as Kiraya saponin, soybean saponin, yukka saponin, enju saponin, beet saponin, azuxaponin, carrot saponin, tea species saponin, hechimasaponin, and tsubokusaponin.
  • Lecithin is a mixture of phospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, and phosphatidylinositol with components such as triglycerides, fatty acids, and carbohydrates from vegetable oils, and is a known component in pharmaceuticals, quasi-drugs, and cosmetics. is there.
  • the lecithin may be natural lecithin derived from animals and plants (for example, soybean lecithin, egg yolk lecithin, etc.) itself, a chemically treated product of natural lecithin, or a purified product of natural lecithin. ..
  • the chemically treated product of natural lecithin include hydrogenated lecithin obtained by hydrogenation treatment (for example, fully hydrogenated lecithin and partially hydrogenated lecithin), hydroxylated lecithin obtained by hydroxylation treatment, and the like.
  • the purified product of natural lecithin include lecithin in which the content of phosphatidylcholine is increased by a solvent such as acetone.
  • lysolecithin examples include lyso-forms of the above-mentioned lecithin (natural lecithin, chemically treated natural lecithin, purified natural lecithin). Lysolecithin has a structure in which the fatty acid at the 2-position of phosphatidylcholine is removed by hydrolysis (dissolution) of lecithin by an enzyme such as phospholipase A2.
  • lecithin, lysolecithin and saponin are preferably mentioned, more preferably lecithin and lysolecithin, and further preferably lysolecithin, from the viewpoint of obtaining better skin irritation reducing property and detergency. Can be mentioned.
  • These natural surfactants may be used alone or in combination of two or more.
  • the content of the component (A) in the skin cleansing spray agent of the present invention is not particularly limited and can be appropriately determined according to the cleansing power to be imparted. Since the skin cleansing spray agent of the present invention can be washed without applying physical friction to the skin, the blending amount of the surfactant in the skin cleansing spray agent can be adjusted to the conventional liquid composition for skin cleansing. It is possible to significantly reduce the amount of the compounding amount contained in the above, and it is possible to effectively exert the detergency even with a small amount of the surfactant which originally cannot exert the effective detergency. From this point of view, the content of the component (A) in the skin cleansing spray agent of the present invention is preferably 0.025 to 2% by weight.
  • the upper limit of the range of the content of the component (A) is 1.5% by weight or less, preferably 1% by weight or less, more preferably. 0.9% by weight or less, more preferably 0.6% by weight or less, still more preferably 0.2% by weight or less.
  • the lower limit of the range of the content of the component (A) is preferably 0.1% by weight or more, more preferably 0.5% by weight or more, still more preferably. Is 1.5% by weight or more, particularly preferably 1.8% by weight or more.
  • the skin cleansing spray agent of the present invention contains an amphipathic ester as a component (B).
  • the component (B) does not show a cleansing action by itself, but by coexisting with the component (A), the cleansing power of the skin cleansing spray can be improved while maintaining low irritation.
  • the amphipathic ester is dissolved in ion-exchanged water adjusted to a conductivity of 70 to 110 ⁇ s / m in an amount of 2% by mass or more at room temperature by the method specified in the General Test Method of the Japanese Pharmacopoeia. , Isotridecyl isononanoate (manufactured by Nisshin Oillio Group, Saracos 913), which is an oil agent, also dissolves in 10% by mass or more at room temperature (25 ° C.), and ester-based surfactants are excluded.
  • the amphoteric ester is not particularly limited, but from the viewpoint of obtaining better skin irritation reduction property and detergency, a dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester, a dicarboxylic acid dialkoxyalkyl ester, and (eicosandic acid) are used. / Tetradecanedioic acid) It is preferable that it is selected from the group consisting of polyglyceryl-10.
  • amphoteric ester any one of dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester, dicarboxylic acid dialkoxyalkyl ester, and (eicosandioic acid / tetradecanedioic acid) polyglyceryl-10 is used alone. Also, two or more kinds may be used in combination. Among these amphipathic esters, the dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester is more preferable from the viewpoint of obtaining better skin irritation reducing property and detergency.
  • the dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester used in the present invention is a diester compound of a dicarboxylic acid and a polyoxyalkylene alkyl ether.
  • Specific examples of the dicarboxylic acid constituting the diester compound of the dicarboxylic acid bis (polyoxyalkylene alkyl ether) ester include oxalic acid, malonic acid, succinic acid, tartaric acid, malic acid, glutaric acid, adipic acid, pemeric acid, and the like.
  • Examples thereof include suberic acid, azelaic acid, sebacic acid, aspartic acid, glutamic acid, acetonedicarboxylic acid, phthalic acid, cyclohexane-1,4-dicarboxylic acid and the like.
  • Examples of the polyoxyalkylene alkyl ether constituting the diester compound include polyoxyethylene monoalkyl ether, and more specifically, diethylene glycol monoethyl ether and triethylene glycol monoethyl ether. Be done.
  • dicarboxylic acid bis (polyoxyalkylene alkyl ether) esters a diester of cyclohexane-1,4-dicarboxylic acid and diethylene glycol monoethyl ether is preferable from the viewpoint of obtaining better skin irritation reduction property and detergency.
  • compound, specifically, INCI name International Cosmetic DiGLYCOL AND Handbook, 13th edition, Vol.
  • cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol examples include, for example, "Neosolue-Aqulio (trade name)” manufactured by Nippon Fine Chemical Co., Ltd.
  • specific examples of the bisethoxydiglycol succinate include "High Aquos Star DCS (trade name)” manufactured by Higher Alcohol Industry Co., Ltd.
  • dicarboxylic acid bis (polyoxyalkylene alkyl ether) esters may be used alone or in combination of two or more.
  • the dicarboxylic acid dialkoxyalkyl ester used in the present invention is a diester compound of a dicarboxylic acid and an alkoxy alcohol.
  • Specific examples of the dicarboxylic acid constituting the diester compound of the dicarboxylic acid dialkoxyalkyl include oxalic acid, malonic acid, succinic acid, tartaric acid, malic acid, glutaric acid, adipic acid, pemeric acid, suberic acid, and azelaic acid. Examples thereof include sebacic acid, aspartic acid, glutamic acid, acetone dicarboxylic acid, phthalic acid, cyclohexane-1,4-dicarboxylic acid and the like.
  • Examples of the alkoxy alcohol constituting the diester compound include 2-methoxyethanol and 2-ethoxyethanol.
  • a diester compound of succinic acid and 2-ethoxyethanol is preferable, specifically, diethoxyethyl succinate, from the viewpoint of obtaining better skin irritation reduction property and detergency. Can be mentioned.
  • dicarboxylic acid dialkoxyalkyl esters may be used alone or in combination of two or more.
  • the polyglyceryl-10 (eicosanedioic acid / tetradecanedioic acid) used in the present invention is not particularly limited, but for example, "Neosolue-Aqua (trade name)" and “Neosolue-AquaS” manufactured by Nippon Seika Co., Ltd. Product name) ”and the like.
  • the content of the component (B) in the skin cleansing spray agent of the present invention is not particularly limited, and examples thereof include 0.1% by weight or more. From the viewpoint of obtaining better detergency and / or further reducing the feeling of tension due to insufficient moisturizing, the content of the component (B) is preferably 0.5% by weight or more, more preferably 1. 5% by weight or more, more preferably 3% by weight or more.
  • the upper limit of the content of the component (B) is not particularly limited, but from the viewpoint of stability such as suppressing precipitation of the skin cleansing spray after high temperature storage, for example, 5% by weight or less, preferably 4% by weight. % Or less, more preferably 2% by weight or less, still more preferably 1.2% by weight or less, still more preferably 1% by weight or less.
  • the ratio of the component (A) to the component (B) is not particularly limited and is determined by each of the above-mentioned contents, but from the viewpoint of obtaining better skin irritation reduction property and cleansing power. Therefore, for example, 0.1 to 100 parts by weight of the component (B) is mentioned with respect to 1 part by weight of the component (A). Further, from the viewpoint of obtaining better detergency when the component (A) is in a small amount of about 0.5 to 1.5% by weight, the component (B) is preferable with respect to 1 part by weight of the component (A). Examples thereof include 2 to 100 parts by weight, preferably 2.5 to 50 parts by weight, and more preferably 3 to 10 parts by weight.
  • the component (B) is preferably 2 to 100 parts by weight, more preferably 2.5 to 90 parts by weight, and further, with respect to 1 part by weight of the component (A). Preferably, it is 3 to 80 parts by weight.
  • the skin cleaning spray agent of the present invention contains a cooling sensation component as the component (C).
  • the cold sensation component is not particularly limited as long as it is a component that provides a cool sensation.
  • Examples thereof include timol, eugenol, anetol, methyl salicylate, camphor, spiranthol, trimethylcyclohexanol, 3-mentoxy-2-methylpropane-1,2-diol and the like.
  • One of these cooling sensation components may be used alone, or two or more thereof may be used in any combination.
  • menthol and menthol succinate are preferably mentioned from the viewpoint of more effectively obtaining a comfortable cooling sensation, and a combination of menthol and menthol succinate is preferable from the viewpoint of sustaining the cooling sensation. Can be mentioned.
  • the menthol may be any of d-form, l-form, and dl-form, but l-form and dl-form are preferable, and l-form is more preferable. Further, as the menthol, an essential oil containing menthol may be used.
  • Monomentyl succinate is an ester of succinic acid and menthol, and the menthol may be any of d-form, l-form, and dl-form, but l-form and dl-form are preferable, and more preferable. Is l-body.
  • the content of the component (C) in the skin cleansing spray agent of the present invention may be appropriately determined according to the cooling sensation to be imparted, and is not particularly limited, but is cold while imparting a comfortable cooling sensation.
  • the content of the component (C) is preferably 0.01 to 0.5% by weight, more preferably 0.1 to 0.5% by weight, and the cooling sensation.
  • the viewpoint of further suppressing skin irritation caused by the ingredients or obtaining better stability after high temperature storage preferably 0.001 to 0.3% by weight, more preferably 0.001 to 0.2% by weight. Can be mentioned.
  • the skin cleansing spray agent of the present invention contains other bases and additives required for formulation and the like as long as the effects of the present invention are not impaired. May be good.
  • Such additives are not particularly limited as long as they are pharmaceutically acceptable, but for example, water, lower alcohols having 1 to 5 carbon atoms (ethanol, isopropanol, etc.), and polyhydric alcohols (ethylene glycol, Aqueous bases such as 1,3-butylene glycol (1,3-BG), propylene glycol, isoprene glycol, diethylene glycol, dipropylene glycol, polypropylene glycol, glycerin, etc.; preservatives (phenoxyethanol, methylparaben, propylparaben, benzoic acid, etc.) , Sodium citrate, sorbic acid, etc.), flavoring agents (citral, citroneral, farnesol, etc.), colorants (tar pigments (brown 201, blue 201, yellow 4, yellow 403, etc
  • Viscous agent hydroxypropyl cellulose, hydroxyethyl cellulose, crosslinked acrylic acid polymer, carboxyvinyl polymer, hypromerose, polyvinylpyrrolidone, sodium alginate, ethyl cellulose, sodium carboxymethyl cellulose, xanthan gum, carrageenan, etc.
  • pH adjustment Agents phosphate, hydrochloric acid, citric acid, sodium citrate (trisodium citrate), succinic acid, tartrate, sodium hydroxide, potassium hydroxide, triethanolamine, triisopropanolamine, etc.
  • wetting agents dl-pyrrolidone carboxylic
  • stabilizers dibutylhydroxytoluene, butylhydroxyanisole, sodium edetate, sodium metaphosphate, L-arginine, L-aspartic acid, DL-alanine, glycine, eryth
  • the skin cleansing spray agent of the present invention may contain, if necessary, other pharmacological components in addition to the above-mentioned components as long as the effects of the present invention are not impaired.
  • pharmacological components include vitamins (vitamin A, vitamin B1, vitamin B2, vitamin B5, vitamin B6, vitamin B12, vitamin C, vitamin D, vitamin K, niacin).
  • the form of the skin cleansing spray agent of the present invention is liquid or gel at room temperature.
  • the viscosity of the skin cleansing spray agent of the present invention is 10,000 mPa ⁇ s or less, preferably 5000 mPa ⁇ s or less at 20 ° C.
  • the viscosity is a value measured by a BL viscometer (rotor No. 3, 6 rpm, 20 ° C.).
  • the container for accommodating the skin cleansing spray agent of the present invention is not particularly limited as long as it is a spray type container.
  • the spray container in the present invention discharges the contents in a mist state, and is different from the pump former container that discharges the skin cleansing composition in a foam state.
  • the skin cleansing spray agent is directly applied to the skin by spraying without foaming before application to the skin. .. Therefore, it is easy to apply to the skin, and physical friction by hands or the like at the time of application can be avoided.
  • the spray type container include a pump type spray container which is a non-aerosol type spray container and an aerosol type spray container.
  • the diameter (nozzle inner diameter) of the spray container include 0.01 to 3 mm ⁇ , preferably 0.1 to 1 mm ⁇ .
  • the injection amount per push is, for example, 0.05 to 1.2 g, preferably 0.1 to 0.3 g.
  • the skin cleansing spray of the present invention is used to remove body fluids such as oils and sweats on the skin, stains, etc., and is not used as a makeup remover (cleansing).
  • the skin cleansing spray agent of the present invention is used by applying it to the skin as it is without foaming without diluting with water.
  • the amount used at one time depends on the concentration of the surfactant, the degree of stain, etc., but for example, when used for face washing, 0.5 to 3 g, preferably 1 to 2 g can be mentioned.
  • the spray agent for skin cleansing of the present invention is a formulation having excellent cleansing power, it is possible to cleanse the skin by using the mechanical force of the liquid flow without giving physical friction in this way. The burden is significantly reduced and an extremely gentle cleaning method becomes possible.
  • the skin cleansing spray agent of the present invention is particularly suitable for the above-mentioned cleaning method that does not give physical friction to the skin, but after applying the skin cleansing spray agent to the site to be cleaned, a hand or the like is used. It does not exclude the usage of scrubbing.
  • the site to be cleaned of the skin cleansing spray agent of the present invention is not particularly limited because it can clean any body part, and examples thereof include hands, hair, scalp, body, and face. Since the spray agent for skin cleaning of the present invention is applied to the site to be cleaned by spraying, it is suitable for use on hair, scalp, and body from the viewpoint of ease of application. In addition, the skin cleansing spray agent of the present invention can exert excellent cleansing power without foaming in advance, and is therefore suitable for use on the face sensitive to irritation. Further, the skin cleansing spray agent of the present invention is particularly suitable for the skin condition of the part to be cleaned, such as skin having a reduced barrier function, skin having a reduced ability to retain water, and skin exhibiting hot spots. Is. Preferred examples of skin exhibiting reduced barrier function, reduced ability to retain water, and burning are inflamed skin, and more preferred examples are skin after sunburn.
  • the skin cleansing spray can be washed away with water.
  • it may be performed in the same manner as a normal face wash, but from the viewpoint of reducing the burden on the skin, it is preferable to wash off using the mechanical force of the water stream so as not to give friction by hand.
  • the skin cleansing spray agent of the present invention is also suitable for cleaning in hospitals, skin cleansing treatments such as face washing in beauty salons and beauty salons, and disaster supplies. If it is not washed away, a water-absorbent base material such as a towel or tissue may be used to absorb and remove the skin-cleaning spray agent remaining on the washed area.
  • the skin cleansing spray agent of the present invention has a predetermined form by mixing the above-mentioned components (A), (B), and (C), and other components to be blended as necessary. After being prepared in, it is manufactured by being housed in a spray container. When it is housed in an aerosol spray container as a spray container, it is manufactured by being housed together with a spray agent such as gas.
  • a skin cleansing spray having the compositions shown in Tables 1 to 4 was prepared. Details of each component shown in Tables 1 to 4 are as follows.
  • the skin cleansing sprays shown in Tables 1 to 4 are liquid, and their viscosities at 20 ° C. (measured by BL viscometer (Brookfield B-type viscometer) rotor No. 3 and 6 rpm) are all 5000 mPa. ⁇ It was in the range of s or less.
  • ⁇ Cocoyl glutamic acid TEA (Ajinomoto Co., Inc.
  • Amisoft CT-12S (trade name)" ⁇ Cocoyl methyl taurine Na (“Diapon K-SF (trade name)” manufactured by NOF CORPORATION) -N-Lauroyl aspartate sodium solution (20% by weight) (“Aminoformer FLDS-L (trade name)” manufactured by Asahi Kasei Fine Chemicals Co., Ltd.) -Polyoxyethylene lauryl ether acetic acid (“Kao Akipo RLM-45 (trade name)” manufactured by Kao Corporation) ⁇ Cocamide DEA (“Amisol CDE-G (trade name)” manufactured by Kawaken Fine Chemicals Co., Ltd.) -PEG-60 hydrogenated castor oil (polyoxyethylene hydrogenated castor oil; Nikko Chemicals Co., Ltd.
  • NIKKOL HCO-60 (trade name)" -Polyoxyethylene sorbitan monostearate (Leodol TW-S120V manufactured by Kao Corporation) -Glycerin mono-2-ethylhexyl ether (SEPPIC "sensivaSC 50 JP (trade name)”) ⁇ Cocamidopropyl betaine ("Softazoline CPB (trade name)” manufactured by Kawaken Fine Chemicals Co., Ltd.) -Lauryl hydroxysulfobetaine solution (30% by weight) (Kao Corporation “Anhitor 20HD (trade name)”) ⁇ Lysolecithin (“Resolecithin Kyowa (trade name)” manufactured by Kyowa Hakko Bio Co., Ltd.) ⁇ Kiraya extract (“Kiraya extract BG” manufactured by Maruzen Pharmaceuticals Co., Ltd., saponin content 5% by weight) -Cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol ("Ne
  • each skin cleansing spray agent is contained in a pump-type spray container (injection amount per push of "Z-155-C110 (trade name)" manufactured by Takemoto Yohki Co., Ltd. is 0.15 g). It was applied by spraying 5 g directly onto the face. It was left for about 5 seconds, and then rinsed with water so that the hands did not touch the face. After holding the face with a towel and absorbing water, the feeling of dirt removal on the skin was scored by sensory evaluation based on the following indexes.
  • each skin cleansing spray agent is contained in a pump-type spray container (Takemoto Yohki Co., Ltd. "Z-155-C110 (trade name)" (injection amount per push is 0.15 g), and 1 .5 g was applied by spraying directly on the face. Leave it for about 5 seconds, then rinse with water so that the hands do not touch the face. Hold the face with a towel and absorb the water, then feel taut. Was scored by sensory evaluation based on the following indexes. The stronger the degree of tension, the less moisturizing.
  • each skin cleansing spray agent is contained in a pump-type spray container (Takemoto Yohki Co., Ltd. "Z-155-C110 (trade name)" (injection amount per push is 0.15 g), and 5 g. Was applied by spraying directly onto the entire body. It was left for about 5 seconds, and then rinsed with water so that the hands did not touch the skin. After holding the skin with a towel and absorbing the water, a feeling of coldness was felt. Scored by sensory evaluation based on the following indicators.
  • ⁇ Cultured epidermal skin irritation test (in vitro evaluation of skin irritation)> The prepared skin cleansing spray was subjected to a cultured epidermal skin irritation test as follows. 1. 1. Preparation of Cultured Epidermis Model LabCite EPI-MODEL24 The assay medium was warmed and 0.5 mL each was added to a 24-well assay plate. Cultured epidermis model LabCite EPI-MODEL24 (lot number: LCE24-180226-A) was transferred to a 24-well assay plate supplemented with assay medium. After confirming that there were no bubbles on the bottom surface of the culture cup, the cells were placed in a CO 2 incubator and allowed to stand for 1 hour or more until exposure to the test substance.
  • test substance Twelve of the 24 epidermis models were used (the rest were pre-cultured until this test). A 24-well assay plate was removed from the CO 2 incubator. The assay medium was warmed and 1.0 mL each was added to the third row of the 24-well assay plate. 25 ⁇ L of the test substance (spray agent for cleaning each skin) was added dropwise to the culture epidermis of the culture cup without using a pump-type spray container, and the whole was exposed. After 1 minute, 5 minutes and 10 minutes after exposure, the test substance was aspirated and removed, and the cultured epidermis model in the cup was washed with phosphate buffer (PBS) and transferred to the third row of the 24-well assay plate.
  • PBS phosphate buffer
  • MTT test occurs when MTT [3- (4,5-dimethylthiazol-2-yl) -2,5-diphenyltrazolium bromide] taken up into cells is reduced by intracellular mitochondrial dehydrogenase. This is a method of measuring the viable cell ratio by extracting a formazan dye with an organic solvent and measuring the absorbance at 570 nm.
  • MTT medium 10 mL was prepared at a final concentration of 0.5 mg / mL.
  • the MTT medium was warmed and 0.5 mL each was added to row 4 of the 24-well assay plate.
  • the cultured epidermis model was transferred to row 4 of the 24-well assay plate and placed in a CO2 incubator for 3 hours MTT reaction. After completion of the MTT reaction, the cultured skin was picked up with tweezers and taken out, and transferred to a 1.5 mL microtube. 300 ⁇ L of isopropanol was placed in a microtube and the cultured epidermis model was completely immersed. After that, it was allowed to stand for 2 hours, and the microtube was vortexed to extract the pigment.
  • Extract 200 mL was placed in each well of a 96-well plate. Further, as a blank (negative control), 200 ⁇ L of isopropanol was added to A1. Absorbance at 570 nm and 650 nm was measured with a microplate reader. The value obtained by subtracting the absorbance at 650 nm from the absorbance at 570 nm was used as the measured value, and the viable cell ratio of the test substance was calculated from the following formula.
  • the viable cell rate was classified based on the following criteria, and skin irritation was evaluated. The results are shown in Tables 3-4. ⁇ : 90% or more ⁇ : 75% or more and less than 90% ⁇ : 65% or more and less than 75% ⁇ : 50% or more and less than 65% ⁇ ⁇ : less than 50%
  • a skin cleansing spray agent containing more than 2% by weight of a surfactant alone can also obtain excellent cleansing power simply by applying it directly to the skin by spraying.
  • the surfactant concentration shown in Reference Examples 1 to 3 when the surfactant concentration is 2% by weight or less as shown in Reference Examples 9 to 20, not only the detergency but also the detergency is obtained. Excellent hypoallergenicity was also achieved. That is, by setting the surfactant concentration of the skin cleaning spray agent applied directly to the skin by spraying to 0.025 to 2% by weight, it is possible to perform cleaning that is physically and chemically gentle on the skin. Shown. On the other hand, none of the skin cleansing composition of Reference Examples 1 to 20, Reference Comparative Examples 1 to 15 and Reference Examples 1 to 3 was comfortable due to a feeling of coldness.
  • a skin cleansing spray having the compositions shown in Tables 5 to 7 was prepared. Details of each component shown in Tables 5 to 7 are as shown in the reference test example. Further, l-menthol was used as the menthol, and an ester of succinic acid and l-menthol was used as the menthol succinate.
  • the skin cleansing sprays shown in Tables 5 to 7 are liquids, and their viscosities at 20 ° C. (measured by BL viscometer (Brookfield B-type viscometer) rotor No. 3, 6 rpm) are all 5000 mPa. ⁇ It was in the range of s or less.
  • each skin cleansing spray agent is contained in a pump-type spray container (“Z-155-C110 (trade name)” manufactured by Takemoto Yohki Co., Ltd., the injection amount per push is 0.15 g), and 5 g is stored. It was applied by spraying directly on the entire body. It was left for about 5 seconds, and then rinsed with water so that the hands did not touch the skin. After holding down the skin with a towel and absorbing water, the feeling of dirt removal on the skin was scored by sensory evaluation based on the following indexes. 3 points: Dirt removal was felt firmly 2 points: Dirt removal was felt 1 point: Dirt removal was slightly felt 0 points: Dirt removal was not felt at all
  • each skin cleansing spray agent is contained in a pump-type spray container (Takemoto Yohki Co., Ltd. "Z-155-C110 (trade name)" (injection amount per push is 0.15 g), and 5 g. Was applied by spraying directly onto the entire body. It was left for about 5 seconds, and then rinsed with water so that the hands did not touch the skin. After holding the skin with a towel and absorbing the water, a feeling of irritation was felt. Scored by sensory evaluation based on the following indicators.
  • each skin cleansing spray agent is contained in a pump-type spray container (Takemoto Yohki Co., Ltd. "Z-155-C110 (trade name)" (injection amount per push is 0.15 g), and 5 g. Was applied by spraying directly onto the entire body. It was left for about 5 seconds, and then rinsed with water so that the hands did not touch the skin. After holding the skin with a towel and absorbing the water, a feeling of tension was felt. It was scored by sensory evaluation based on the following indicators. The stronger the degree of tension, the less moisturizing.
  • the prepared skin cleansing spray was stored at room temperature or under 50 ° C. conditions for 1 week. After storage, the difference in appearance and odor between the skin cleansing spray stored at room temperature and the skin cleansing spray stored under 50 ° C conditions is visually observed, and the high temperature stability is evaluated based on the following indexes. did.
  • the difference in appearance and odor is the precipitation (specifically, precipitation of cyclohexane-1,4-dicarboxylic acid bisethoxydiglycol) and offensive odor (specifically, precipitation) in the skin cleaning spray agent stored under 50 ° C. conditions. Is evaluating the offensive odor caused by menthol and menthyl succinate).
  • the skin cleansing spray agent (Comparative Example 1) containing the surfactant alone did not have detergency because the concentration of the surfactant was too low.
  • the skin cleaning spray agent (Comparative Example 2) containing an amphipathic ester (Comparative Example 3) that does not show detergency by itself together with a surfactant even if the concentration of the surfactant is low, the spray container can be used.
  • excellent detergency was obtained by using the mechanical power of the liquid flow without giving any physical friction, but the skin was tanned in terms of cooling sensation. It wasn't very comfortable.
  • the skin cleaning sprays (Examples 1 to 20), which contain an amphoteric ester which does not show detergency by itself together with the surfactant and also contain a cooling sensation component, even if the concentration of the surfactant is low. It is possible to perform skin-friendly cleaning by simply applying it directly to the skin by spraying from a spray-type container, without giving any physical friction, and by using the mechanical force of the liquid flow to obtain excellent cleaning power. At the same time, it was able to give a pleasant cold feeling to the sunburned and hot skin.
  • Liquid skin cleansing sprays with the formulations shown in Table 8 were prepared. All of the prescription skin cleansing sprays had low skin irritation and had excellent cleansing power, were able to provide a comfortable cooling sensation, and were also excellent in formulation stability at room temperature and high temperature.

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Abstract

[Problème] L'objectif de la présente invention est de fournir une composition de nettoyage de la peau utilisée d'une façon différente de l'état de la technique. [Solution] La présente invention concerne un agent de pulvérisation pour nettoyer la peau qui contient (A) un tensioactif, (B) un ester amphiphile, et (C) un composant rafraichissant et qui est logé dans un récipient de pulvérisation qui est capable de réduire les propriétés d'irritation de la peau d'une composition de nettoyage de la peau tout en présentant un excellent pouvoir nettoyant. En conséquence, il est possible de fournir une nouvelle façon d'utiliser une composition de nettoyage de la peau dans laquelle, lorsqu'elle est appliquée sur la peau, ladite composition de nettoyage de la peau est appliquée en étant pulvérisée directement sur la peau au lieu de la faire mousser à l'avance comme dans une utilisation conventionnelle.
PCT/JP2020/023779 2019-06-26 2020-06-17 Agent de pulvérisation pour nettoyer la peau WO2020262152A1 (fr)

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JP2009035498A (ja) * 2007-07-31 2009-02-19 Nippon Fine Chem Co Ltd メイクアップ除去剤
JP2016044180A (ja) * 2014-08-20 2016-04-04 ホシケミカルズ株式会社 化粧料
JP2016069320A (ja) * 2014-09-30 2016-05-09 株式会社マンダム 皮膚外用剤
JP2020002049A (ja) * 2018-06-27 2020-01-09 小林製薬株式会社 外用組成物

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JP2009035498A (ja) * 2007-07-31 2009-02-19 Nippon Fine Chem Co Ltd メイクアップ除去剤
JP2016044180A (ja) * 2014-08-20 2016-04-04 ホシケミカルズ株式会社 化粧料
JP2016069320A (ja) * 2014-09-30 2016-05-09 株式会社マンダム 皮膚外用剤
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