WO2005090535A1 - Preparation de detergent a base d’huile - Google Patents

Preparation de detergent a base d’huile Download PDF

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Publication number
WO2005090535A1
WO2005090535A1 PCT/JP2005/005624 JP2005005624W WO2005090535A1 WO 2005090535 A1 WO2005090535 A1 WO 2005090535A1 JP 2005005624 W JP2005005624 W JP 2005005624W WO 2005090535 A1 WO2005090535 A1 WO 2005090535A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
pop
polyoxypropylene
mass
hlb
Prior art date
Application number
PCT/JP2005/005624
Other languages
English (en)
Japanese (ja)
Inventor
Hiroki Inoue
Akira Matsuo
Kei Watanabe
Original Assignee
Shiseido Company, Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shiseido Company, Ltd. filed Critical Shiseido Company, Ltd.
Publication of WO2005090535A1 publication Critical patent/WO2005090535A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; 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
    • A61K8/39—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
    • A61K8/72—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
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/18—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • Oil-based cleaning agent oil-based cleaning agent
  • the present invention relates to an oil-based detergent, and more specifically, does not cause turbidity or thickening even when water is mixed, and irritates the mucous membranes such as eyes.
  • Cleansing compositions for make-up can be broadly classified into aqueous cleansing and oily cleansing.
  • the aqueous cleansing is a lotion type consisting of an aqueous ethanol solution of a surfactant, and an aqueous gel type thickening a surfactant with a polymer. Etc. are known.
  • oil-based cleansing there are known a cream type in which an oZw emulsion is inverted by massage to exhibit a cleaning function, and an oil type comprising a surfactant oil solution.
  • the oil type is particularly known to have a high cleaning effect.
  • the type of makeup has become the mainstream, with types that prevent secondary adhesion such as foundations and lipsticks, and types that include high molecular weight silicone such as mascara. Its value in the market is very high.
  • the oil-type cleansing composition is composed of a nonionic surfactant, an oil and a small amount of water, and the surfactant forms a reverse micelle oil solution in which a hydrophilic group is formed inside the oil to form a conjugate. Water is solubilized in the vicinity of the aggregation of the hydrophilic groups to form one phase, and is completely transparent. It is in a state. '
  • the Oinole type Due to its microstructure, the Oinole type has a limited ability to completely and completely take in water, the so-called solubilization amount. If water is mixed in beyond the solubilized amount, it will be in a coexisting state with other phases (two-phase state), so it will be white and cloudy as a whole due to the refractive index difference between the two phases. It becomes. Depending on the type of coexisting phase, the desired cleaning performance as a cleaning agent cannot be exhibited, or the user is strongly impressed with the deterioration of cleansing performance, which is not desirable. Also, if water is mixed in beyond the amount of solubilization, the composition thickens and cannot be applied smoothly, making it difficult to blend in with makeup and failing to exert good massage properties. There was a point.
  • Japanese Patent Application Laid-Open No. 2000-32,729 / 29 discloses that the use of a polyglycerin fatty acid ester of HLB 10 or more in combination with a polyhydric alcohol of 3 or more causes skin Easy to fit into makeup even when wet. ⁇ Cleansing fee is described. However, this method could not prevent the appearance from becoming cloudy, and the composition thickened, making it difficult to blend in with makeup, and in some cases the massage properties were not sufficient.
  • JP-A-6-165224 and JP-A-2001-270809 disclose a combination of a nonionic surfactant and an amphoteric surfactant, and a nonionic surfactant.
  • a cleansing agent that has high detergency even with hands wet with water is described as a combination of a surfactant and a glyceryl ether derivative. There was a problem with irritation to the mucous membranes. Disclosure of the invention
  • the present invention has been made in view of the above-described conventional circumstances, and its purpose is to make the film become cloudy, increase in viscosity and increase the spread of water, and become familiar even if water is mixed in during use. According to the present invention, it is an object of the present invention to provide a liquid oil-based cleaning agent which does not deteriorate and does not deteriorate massage performance, has a good makeup removing effect, and has no irritation to mucous membranes such as eyes.
  • An oil-based detergent comprising a compound having a polyoxypropylene (POP) group having 5 to 35 addition moles in the molecule is provided.
  • POP polyoxypropylene
  • POP sorbitol POP diglycerin, POP glycerin, POP butynoleatene or POP POE (polyoxyethylene) It is preferable that at least one selected from random copolymers, and it is particularly preferable that P ⁇ P sorbite be used.
  • the compounding amount of the nonionic surfactant having a carbon number of 14 or more in the component (b) and an HLB of 9 to 16 relative to the total amount of the detergent is 5 to 40% by mass
  • the higher fatty acid and Z or higher alcohol of the component (c) are It is preferably a branched higher fatty acid or higher alcohol. According to the present invention, due to the above configuration, even when water is mixed, high cleaning performance is maintained, there is no cloudiness or thickening on the appearance, no reduction in massage performance, and an excellent feeling of use. It can provide an oil-based cleaning agent that is less irritating to the eyes.
  • the present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a liquid oil, a specific / dione surfactant, a higher fatty acid and / or a higher alcohol, and a compound having a polyoxypropylene group in the molecule.
  • the present inventor has found that an oil-based cleaning agent that combines and solves the above-mentioned problems, and has completed the present invention.
  • the liquid oil used in the present invention is not particularly limited as long as it is a liquid oil normally used in cosmetics, and any liquid oil can be used.
  • hydrocarbon oils such as liquid paraffin, squalane, orefin oil, light isoparaffin, etc .
  • the compounding amount of the liquid oil is 50 to 95% by mass, and preferably 60 to 80% by mass, based on the whole oil-based cleaning agent. If the amount of the liquid oil is less than 50% by mass, it is difficult to obtain a sufficient cleaning effect, and if it exceeds 95% by mass, the water-washing property is impaired.
  • Nonionic surfactant having an alkyl chain of 14 or more carbon atoms and an HLB of 9 to 6
  • the alkyl chain has 14 or more carbon atoms and HLB is 9
  • nonionic surfactants of No. 1 to No. 16 are not particularly limited as long as they are commonly used in cosmetics, and any surfactant can be used.
  • P O E (10) Reinoreethenore (HLB 10)
  • ⁇ HLB 10
  • HLB is from 9 to 16, preferably from 9 to 14. If HLB is less than 9, it becomes cloudy when water is mixed, and if it exceeds 16, it is difficult to obtain a uniform composition, which is not preferable.
  • the amount of the nonionic surfactant described above is preferably 5 to 40% by mass, more preferably 20 to 40% by mass, based on the whole oil-based detergent. If the amount of the nonionic surfactant is small, the mixture may become cloudy when mixed with water, and if it is too large, the viscosity may be increased when mixed with water and the spread may be increased.
  • the higher fatty acid used in the present invention all higher fatty acids usually used for cosmetic bases and the like can be applied.
  • higher fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, araquinic acid, behenic acid, and other saturated fatty acids; 2-palmitoleic acid, petroserin Acids, unsaturated fatty acids such as oleic acid, elaidic acid, ricinoleic acid, linoleic acid, linoleic acid, linolenic acid, and arachidonic acid; and branched fatty acids such as isostearic acid.
  • Higher alcohols include saturated higher alcohols such as laurine alcohol, myristolenorecole, cetinoleanolecole, stealinelenorecole and behenyl alcohol; and unsaturated higher alcohols such as oleyl alcohol. Branched higher alcohols such as alcohol, otatyl dodecanol, hexyldecanol, and sostearyl alcohol. The .
  • the component (C) is preferably a branched higher fatty acid or a higher alcohol from the viewpoint of system stability. It is particularly preferable to use isostearic acid and isostearyl alcohol, and it is particularly preferable to use isostearic acid.
  • the blending amount of these higher fatty acids or higher alcohols is preferably 1 to 10% by mass, and more preferably 1 to 5% by mass. When the amount is small, it may be difficult to obtain a uniform composition. On the other hand, when the amount is large, the washing property may be impaired.
  • Examples of the compound having a propylene oxide group used as the component (d) in the present invention include, for example, 2-chain polyalkylene glycols, multi-chain polyalkylene glycols, and 2-chain polyalkylene glycol.
  • Polyoxyalkylene groups containing a POP group such as kill ethers, multi-chain polyoxyalkylene alkyl ethers, two-chain polyoxyalkylene esters, and multi-chain polyoxyalkylene esters, are particularly preferred.
  • Polypropylene sorbitol Is preferred. When the number of moles of added polyoxypropylene is 2 or less or 40 or more, the stability of the system is impaired, which is not preferable.
  • the POP / POE random copolymer has the following general formula (I) It is represented by ⁇
  • R 1 and R 2 is a hydrocarbon group or a hydrogen atom having 1 to 4 carbon atoms which may be the same or different, and the ratio of the number of hydrogen atoms to the number of hydrocarbon groups of R 1 and R 2 is 0.15 or less.
  • the compounding amount of the compound having a POP group of the component (d) is preferably 1 to 10 mass 0 /.
  • the good Ri preferably from 1 to 5 weight 0/0. If the amount is less than 1% by mass, there is a risk that the effect of suppressing turbidity when water is mixed during use and an increase in viscosity to increase the spread may not be sufficiently exhibited. If it is added in excess of mass%, the stability of the system may be impaired.
  • the oil-based cleaning agent of the present invention is usually compounded in the fields of cosmetics and pharmaceuticals in addition to the above-mentioned components (a) to (d), which are essential components of the present invention, as long as the effects of the present invention are not impaired.
  • Various additional components can be blended.
  • water-soluble active substances such as vitamin B group, vitamin C and derivatives thereof, tranexamic acid, pantothenic acid and derivatives thereof, and vitamins such as bition, water-soluble polymers such as guar gum, xanthan gum, and polyvinyl alcohol, Thickeners, buffers such as arginine, aspartic acid, citric acid, tartaric acid, and lactic acid; chelating agents such as EDTA Agents, preservatives, etc., ultraviolet absorbers, various powders, various dyes, and the like.
  • the dosage form of the oil-based cleaning agent of the present invention is not particularly limited, and can be used as a liquid preparation, a gel preparation, an aerosol preparation, a sheet impregnated preparation, etc. Therefore, a liquid preparation is more preferable.
  • the oil-based cleansing agent of the present invention can be used as a skin cleansing agent in, for example, the cosmetics field, the quasi-drug field, and the pharmaceutical field. In particular, it is preferable to use it as a makeup cleaning agent.
  • An oil-based cleaning agent having the composition shown in Tables I to V below is prepared by a conventional method, and the stability of the composition, the transparency when mixed with water, and the Evaluation of skin extension and eye irritation was performed, and the results are shown in the respective tables.
  • the unit of the compounding amount is mass%.
  • the polyoxyethylene polyoxypropylene dimethyl ether is obtained by randomly adding a polyoxypropylene group and an oxyethylene group, and is described in JP-A-2003-113203. Manufactured in the manner described.
  • the stability of the composition was evaluated by placing the test samples of Examples and Comparative Examples in 50 ml transparent glass bottles with screw caps, at 0 ° C, 25 ° C, and 50 ° C. The test was performed by leaving it at a temperature and observing its appearance for one month, and evaluated according to the following criteria. (Evaluation criteria) ⁇
  • a small amount of precipitate is formed at 0 ° C, but when returned to 25 ° C and allowed to stand, the precipitate disappears and returns to a uniform and normal appearance.
  • the professional evaluation panel evaluated the state of the sample according to the following criteria when 2 g of the sample of the example and the comparative example were used with a hand wetted with 1.5 g of water.
  • the expert evaluation panel evaluated the elongation to the skin when applying 2 g of the sample of the example and the comparative example to the face with a hand wetted with 1.5 g of water according to the following criteria.
  • G Out of 10 people, 1 or less reported irritation to eyes.
  • F 2 or 3 out of 10 people report eye irritation
  • Example 1 Example 7
  • Example 8 Example 9
  • Example 10 Liquid paraffin 40 40 40 40 40 40 Cetyl octoate 20 20 20 20 20 20 20 20
  • Polyoxypropylene (25) sorbit-5---Polyoxypropylene (20) butyl ether-5--Polyoxypropylene (9) diglyceryl ether-1-5-Polyoxypropylene (16) glycol--1-5 Polyoxypropylene (40) butyl ether---1-Polyoxyethylene (10) sorbitol 1-1--Polyoxyethylene (11) methyl glucoside-1---Polyoxyethylene polyoxypropylene 1 1---Dimethyl ester Tell (25E0) (40P0)
  • Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Liquid paraffin 40 40 40 40 45 Cetyl octoate 20 20 20 20 20 20 20 20
  • Polyoxypropylene (25) sorbit---1-1 Polyoxypropylene (20) butyl ether---1-1 Polyoxypropylene (9) diglyceryl ether-1-1-Polyoxypropylene (16) dalicol---1-1 Polyoxypropylene (40) butyl ether 5--11 Polyoxyethylene (10) sorbit-5-11 Polyoxyethylene (11) methyl darcoside--5-11 Polyoxyethylene polyoxypropylene---5-Dimethyl ether (25E0) (40P0)
  • Sostearic acid 1 Polyoxyprev pyrene (25) Sorbit 5 Tocopherol acetate 0 Water 0 Alcohol 1

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

Il est prévu une préparation de détergent à base d'huile liquide comprenant (a) 50 à 95 % en masse de matière huileuse liquide, (b) un tensioactif non ionique ayant une chaîne alkyle supérieure ou égale à C14 et un HLB de 9 à 16, (c) un acide gras supérieur et/ou un alcool supérieur, et (d) un composé ayant dans la molécule un groupe polyoxypropylène ayant un nombre de moles d’oxypropylène ajoutés de 5 à 35.
PCT/JP2005/005624 2004-03-22 2005-03-18 Preparation de detergent a base d’huile WO2005090535A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004082568A JP4429053B2 (ja) 2004-03-22 2004-03-22 油性洗浄料
JP2004-082568 2004-03-22

Publications (1)

Publication Number Publication Date
WO2005090535A1 true WO2005090535A1 (fr) 2005-09-29

Family

ID=34993691

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/005624 WO2005090535A1 (fr) 2004-03-22 2005-03-18 Preparation de detergent a base d’huile

Country Status (5)

Country Link
JP (1) JP4429053B2 (fr)
KR (1) KR100997503B1 (fr)
CN (1) CN100475940C (fr)
TW (1) TWI353255B (fr)
WO (1) WO2005090535A1 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4814662B2 (ja) * 2006-03-20 2011-11-16 資生堂ホネケーキ工業株式会社 洗浄剤組成物および洗浄剤
JP5236336B2 (ja) * 2008-04-04 2013-07-17 日本メナード化粧品株式会社 オイル状クレンジング料
JP5995453B2 (ja) * 2012-01-31 2016-09-21 アサヌマ コーポレーション株式会社 化粧料及びその製造方法
JP6239822B2 (ja) * 2012-12-27 2017-11-29 ポーラ化成工業株式会社 逆ベシクル組成物
JP6540101B2 (ja) * 2014-04-17 2019-07-10 日油株式会社 クレンジング料
JP2016034914A (ja) * 2014-08-01 2016-03-17 花王株式会社 清拭シート
JP6439923B2 (ja) * 2014-10-31 2018-12-19 ポーラ化成工業株式会社 被膜除去用組成物
JP6639176B2 (ja) * 2015-10-02 2020-02-05 花王株式会社 毛髪洗浄剤組成物
JP6887841B2 (ja) * 2016-03-29 2021-06-16 株式会社コーセー 化粧料
JP2016199600A (ja) * 2016-09-07 2016-12-01 ロート製薬株式会社 油性クレンジング化粧料
JP6805947B2 (ja) * 2017-04-20 2020-12-23 日油株式会社 固形石けん組成物
JP7222897B2 (ja) * 2017-09-13 2023-02-15 株式会社 資生堂 油性洗浄料
JP6954009B2 (ja) * 2017-11-02 2021-10-27 日油株式会社 油性化粧料
WO2019240067A1 (fr) * 2018-06-12 2019-12-19 花王株式会社 Composition de nettoyage de la peau solubilisée

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0826929A (ja) * 1994-07-22 1996-01-30 Pilot Ink Co Ltd 化粧料除去剤組成物
JPH09255520A (ja) * 1996-03-22 1997-09-30 Pola Chem Ind Inc 非水化粧料
JPH1135421A (ja) * 1997-07-17 1999-02-09 Shiseido Co Ltd 液状油性皮膚洗浄料
JP2003221310A (ja) * 2001-11-21 2003-08-05 Shiseido Co Ltd 皮膚洗浄料

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0826929A (ja) * 1994-07-22 1996-01-30 Pilot Ink Co Ltd 化粧料除去剤組成物
JPH09255520A (ja) * 1996-03-22 1997-09-30 Pola Chem Ind Inc 非水化粧料
JPH1135421A (ja) * 1997-07-17 1999-02-09 Shiseido Co Ltd 液状油性皮膚洗浄料
JP2003221310A (ja) * 2001-11-21 2003-08-05 Shiseido Co Ltd 皮膚洗浄料

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CN1934234A (zh) 2007-03-21
KR20070019973A (ko) 2007-02-16
CN100475940C (zh) 2009-04-08
KR100997503B1 (ko) 2010-12-01
JP2005264110A (ja) 2005-09-29
TWI353255B (en) 2011-12-01
JP4429053B2 (ja) 2010-03-10
TW200534871A (en) 2005-11-01

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