WO2007122802A1 - Composition détergente - Google Patents

Composition détergente Download PDF

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Publication number
WO2007122802A1
WO2007122802A1 PCT/JP2007/000376 JP2007000376W WO2007122802A1 WO 2007122802 A1 WO2007122802 A1 WO 2007122802A1 JP 2007000376 W JP2007000376 W JP 2007000376W WO 2007122802 A1 WO2007122802 A1 WO 2007122802A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
cleaning composition
group
composition according
weight
Prior art date
Application number
PCT/JP2007/000376
Other languages
English (en)
Japanese (ja)
Inventor
Yoshinori Tamura
Ryosuke Fujii
Original Assignee
Kao Corporation
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
Priority claimed from JP2006106941A external-priority patent/JP4705505B2/ja
Application filed by Kao Corporation filed Critical Kao Corporation
Priority to KR1020087024489A priority Critical patent/KR101353160B1/ko
Priority to CN2007800126050A priority patent/CN101415810B/zh
Publication of WO2007122802A1 publication Critical patent/WO2007122802A1/fr

Links

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
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/34—Derivatives of acids of phosphorus
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or 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
    • C11D3/20—Organic compounds containing oxygen

Definitions

  • the present invention relates to a detergent composition that is less irritating to the skin and the like, is excellent in stability and foaming property, has a foamy quality, has a good feeling in use, and has excellent stability.
  • Phosphate-based surfactants are less irritating to the skin and hair than sarcophagus, alkyl ether sulfates, alkyl sulfates, etc., and are widely applied as components of skin cleansing agents. . In addition, due to its characteristics, it has been applied to a wide range of other surfactants mixed with nonionic surfactants.
  • phosphate ester surfactants are obtained as a mixture of monoester and ester, and alkyl phosphate esters contain a mixture of dialkyl phosphates having poor water solubility and poor foaming ability. . If this is used alone as the main component of the cleaning agent, there are generally problems with foaming power and foam quality. Therefore, several methods for combining auxiliary agents have been proposed. Among them, the method of adding a higher fatty acid salt as an auxiliary agent (Patent Document 1) is an excellent method for enhancing foaming power, but this method has a high weight ratio of alkyl phosphate and a low ratio of higher fatty acid salt.
  • Patent Document 2 In comparison with the higher fatty acid salt (Ishizuchi) alone, the foaming power and foam quality were still not satisfactory.
  • Patent Document 3 the method of adding a higher fatty acid salt to polyoxyethylene alkyl ether phosphate (Patent Document 2) is still not satisfactory in terms of foaming power and stability.
  • Patent Document 3 the method using a glyceryl ether having an alkyl group or alkenyl group having 6 to 12 carbon atoms as an auxiliary agent (Patent Document 3) improves foaming power in the case of a monoalkyl phosphate ester salt. However, if the ratio of monoalkyl phosphate ester salt is less than 95 5, the foaming power and foam quality are still higher than when only higher fatty acid salts are used.
  • Patent Document 4 discloses a combination of a phosphoric acid monoester, a higher fatty acid salt, and an alkyl glyceryl ether. However, these combinations with a higher phosphate ester ratio and a lower higher fatty acid salt ratio are also disclosed. It was still not satisfactory in terms of foaming power and foam quality.
  • Patent Document 1 JP-A-57-49698
  • Patent Document 2 JP-A-1-31 6309
  • Patent Document 3 Japanese Patent Laid-Open No. 2001_107079
  • Patent Document 4 JP-A-2005-206804
  • the present invention provides the following components (A), (B) and (C)
  • R 1 , R 2 and R 3 each represent a linear or branched alkyl group or alkenyl group having 8 to 18 carbon atoms
  • X 1 , X 2 and Y are a hydrogen atom and an alkali metal, respectively.
  • An atom, an alkaline earth metal atom, an alkanolamine or an ammonium ⁇ , and the average added mole numbers k, m and n each represent a number from 0 to 10
  • R 4 represents a saturated or unsaturated aliphatic hydrocarbon group having 7 to 17 carbon atoms
  • M represents a hydrogen atom, an alkali metal atom, an alkanolamine, or ammonia
  • a higher fatty acid represented by the formula:
  • (C) (C-1) a linear or branched alkyl group having 6 to 12 carbon atoms, wherein ⁇ is one or more glyceryl ethers having an alkenyl group, and
  • R 5 represents a linear or branched alkyl or alkenyl group having 6 to 10 carbon atoms
  • R 6 represents a hydrogen atom or a methyl group
  • AO represents an alkyleneoxy group having 2 to 4 carbon atoms.
  • the average added mole number q represents a number of 0.5 to 3.
  • a cleaning composition that is less than
  • the present invention also provides a body cleaning method in which the cleaning composition is applied to the body.
  • the present invention provides the use of the cleaning composition for body cleaning.
  • the object of the present invention is a cleansing with low irritation to the skin, etc., excellent foaming properties, foam quality is clear, feel good to use (rinse and wash feeling), and has excellent stability. It is to provide an agent composition.
  • the present inventors have combined a glyceryl ether and an alkoxylate together with a higher fatty acid or a salt thereof and a phosphate ester surfactant for a detergent composition using a phosphate ester surfactant.
  • a detergent composition having a low irritation, excellent stability and foaming property, creamy quality, and good usability was obtained.
  • the cleaning composition of the present invention is less irritating to the skin, etc., has excellent foaming properties, has a creamy quality, and has a good feeling during use (rinseability, feeling after washing) and has excellent stability. .
  • R 1 , R 2, and R 3 are each a carbon number It is preferably an alkyl group of 10 to 16, more preferably 12 to 14 , and X 1 , X 2 and Y are preferably an alkali metal atom such as lithium or sodium, particularly triethanolamine, Potassium is preferable from the viewpoint of solubility in water.
  • the average number of moles of ethylene oxide added k, m and n is preferably 0 to 4 moles, more preferably 0 to 2 and even more preferably 0 to 1 mole from the viewpoint of foaming power.
  • the weight ratio (ai) / (a 2) is inferior foaming is less than 50 50, weight ratio (ai) / (a 2) is 90 1 0 than in the formulation increases the melting point of Al Kirurin ester mixture difficult.
  • the content of the phosphate ester surfactant of component (A) is preferably 1 to 15% by weight of the cleaning composition of the present invention from the viewpoint of foaming, detergency and ease of blending. 3 to 10% by weight is more preferable.
  • Component (A) includes, for example, an ethylene oxide added to a corresponding aliphatic alcohol or a corresponding aliphatic alcohol, and an average addition mole number of 0 to 10; phosphoric anhydride, Phosphoric acid ester obtained by reacting phosphoric acid such as orthophosphoric acid, polyphosphoric acid or oxyphosphoric acid, or the phosphoric acid ester partially or completely with sodium hydroxide, hydroxylated lithium, etc. It is a phosphoric ester salt obtained by neutralization.
  • (a / (a 2 ) is the ratio of aliphatic alcohol to water contained in the phosphorylating agent. It can be controlled by rate.
  • R 4 is preferably an alkyl group having 7 to 17 carbon atoms
  • M is an alkali metal atom
  • an alkenolamine Or, ammonium is preferred, and more preferred is a force lithium or an alkali metal atom such as sodium.
  • the higher fatty acid salt may be prepared by neutralizing the higher fatty acid and the base in a compounding tank for producing the cleaning composition. Further, even if a part of the higher fatty acid salt undergoes salt exchange with the counter ion of the phosphate ester salt, it does not hinder the effect of the present invention.
  • Component (B) provides a foam quality improving effect that is not found in component (C), that is, a creamy foam quality, and also improves foaming properties.
  • the higher fatty acid of component (B) or a salt thereof can be used alone or as a mixture of two or more.
  • the content of component (B) is preferably from 5 to 35% by weight, more preferably from 5 to 30% by weight, and from 10 to 25% by weight from the viewpoint of imparting the cleanability and foaming property of the cleaning composition of the present invention. % Is even more preferred.
  • the cleaning composition of the present invention preferable contents of the component (A) and the component (B) are as described above.
  • Component (B) Component (A) The weight ratio is preferably 2 to 9, more preferably 2 to 5.
  • the glyceryl ether of the component (C-1) has a linear or branched alkyl group or alkenyl group having 6 to 12 carbon atoms.
  • n_hexyl group isohexyl group
  • Those having an alkyl group having 6 to 12 carbon atoms such as xyl group, n_heptyl group, n-octyl group, 2_ethylhexyl group, n_nonyl group, n-decyl group, n-lauryl group and the like are preferable.
  • R 5 is a straight or branched chain having 6 to 10 carbon atoms, preferably 8 to 10 carbon atoms.
  • An alkyl group or an alkenyl group, and an alkyl group having 8 carbon atoms is preferred.
  • AO is an alkyleneoxy group having 2 to 4 carbon atoms, more preferably an alkyleneoxy group having 2 to 3 carbon atoms, and still more preferably an alkyleneoxy group having 3 carbon atoms. Specific examples include an ethyleneoxy group, a propyleneoxy group, and a butyleneoxy group.
  • AO max is 70 % of component (C) overall from the viewpoint of economy that reduces the production cost burden such as purification. It is preferably not more than 50% by weight, more preferably not more than 60% by weight, and still more preferably not more than 50% by weight.
  • AO max is 60% by weight or less, further 50% by weight or less, and further 40% by weight or less of the whole component (C). Is preferred.
  • AO max is 70% by weight or less, further 60% by weight or less, and further 50% by weight of the total component (C). % Or less is preferable.
  • R 6 represents a hydrogen atom or a methyl group, and more preferably a hydrogen atom.
  • One or more components (c) can be used.
  • Component (C) has the effect of maintaining stability and improving foaming power.
  • the blending amount of component (C) is preferably 0.1 to 5% by weight, more preferably 0.1 to 3% by weight, and still more preferably 0.2 to 1% by weight in the cleaning composition of the present invention. That's right.
  • the component (C_1) can be obtained, for example, by hydrolyzing the corresponding glycidyl ether and water at 100 to 230 ° C.
  • the component (C_2) can be obtained by, for example, propylene oxide and / or the corresponding aliphatic alcohol. After the reaction with ethylene oxide, the raw material alcohol can be distilled off.
  • the stimulation of the higher fatty acid salt is changed to low stimulation equivalent to the use of a phosphate ester surfactant alone.
  • Foamability which is a defect of the active agent, is improved as well as higher fatty acids.
  • the foam quality is creamy and preferable.
  • the skin feels unsatisfactory, which is a peculiar feeling of use of phosphoric acid ester surfactants.
  • blending at the time of manufacture is easy without any increase in viscosity.
  • the cleaning composition of the present invention is a cleaning composition useful as a skin cleaning agent such as a facial cleanser, a shampoo, a body shampoo, or a body cleaner such as a hair cleaner. It is preferably used as a skin cleanser such as body shampoo.
  • These cleaning compositions can be blended with optional components according to the purpose.
  • optional components include other anionic surfactants, nonionic surfactants, amphoteric surfactants, cationic surfactants, and conditioning components that are usually blended in these detergents.
  • anionic surfactants include alkyl sulfates, polyoxyalkylene alkyl ether sulfates, sulfosuccinic acid surfactants, sulfosuccinamate surfactants, polyoxyalkylene alkylamide ether sulfates, monoglyceride Dosulfate, olefin sulfonate, alkane sulfonic acid Salts, acylated isethionates, acylated amino acid salts, polyoxyalkylene alkyl ether phosphates other than component (A), etc .; nonionic surfactants include alkyl polydarcosides, sucrose fatty acids Examples include esters, polyglycerol fatty acid esters, polyoxyalkylene alkyl ethers, fatty acid alkanolamides, alkylamine oxides, and fatty acid polyhydric alcohol esters.
  • cationic surfactants include linear or branched mono- or di-long alkyl quaternary ammonium quaternary salts, mono- or di-long alkyl tert-amines, and amphoteric surfactants include amides.
  • conditioning components include higher alcohols, silicone and silicone derivatives, lanolin, squalene, hydrocarbons, protein derivatives, polyethylene glycol fatty acid esters and other oil agents, cationized cellulose, cationized guagam and marcoat. (Naruco Co., Ltd.), Softcare KG-3301 W [manufactured by Kao Corporation], and the like.
  • water-soluble polymers such as polysaccharides such as methylcellulose, hydroxyethylcellulose, carboxyvinyl polymer, xanthan gum; polyoxyalkylene Viscosity modifiers such as sorbitan ester, polyoxyethylene glycol distearate, ethanol, etc .; Ethylenediamine tetraacetic acid (EDTA), phosphonates and other chelating agents; methylparaben, butylparaben and other preservatives; vitamins and their precursors, etc.
  • water-soluble polymers such as polysaccharides such as methylcellulose, hydroxyethylcellulose, carboxyvinyl polymer, xanthan gum
  • polyoxyalkylene Viscosity modifiers such as sorbitan ester, polyoxyethylene glycol distearate, ethanol, etc .
  • Ethylenediamine tetraacetic acid (EDTA), phosphonates and other chelating agents methylparaben, butylparaben
  • the cleaning composition of the present invention preferably has a pH of 7 to 11.
  • the cleaning composition of the present invention is preferably used together with water having a hardness of 1 to 30 ° DH.
  • the water used here preferably has a pH of 4 to 9.
  • the cleaning composition of the present invention can be produced according to a conventional method. There are no particular limitations on the dosage form of the cleaning composition of the present invention, and various conventionally known dosage forms such as liquid body shampoos, cream facial cleansings, and the like can be used.
  • the cleaning composition of the present invention is particularly suitable as a cleaning agent for body such as skin and hair.
  • 1-octanol (Calcoal 0898, manufactured by Kao Corporation) 1 61 5. 0 g (1 2. 35 mo I) and hydroxylated power of 6.9 g (0.12 mo I) were charged into the autoclave. After dehydration at 1 10 ° C and 13.3 kPa, addition reaction was carried out at 120 ° C while injecting 1 434 g (24.69 0 1) of propylene oxide at 0.3 MPa. .
  • 1-octanol was distilled off from 1 000 g of the obtained filtrate under the conditions of 130 ° C. and 1.3 kPa. Further, steam treatment was performed by blowing 100 g of steam under the conditions of 145 ° C., 6. O k Pa, and 5 hours to obtain dipropylene glycol monooctyl ether shown in Table 2.
  • the cleaning composition with the composition shown in Table 1 is manufactured by mixing each component at 70 ° C (pH adjusted to 9), foaming property, foam quality, rinsing property, feel after washing, low irritation And stability were evaluated. The results are shown in Table 1.
  • B 1 or more and 2 or less people felt the stimulus, but it was an acceptable weak stimulus.
  • C 1 or more and 2 or less people felt the stimulus, but it was an unacceptably strong stimulus.
  • the cleaning composition was placed in a glass bottle and stored at 20 ° C for 1 month, and then the appearance was visually evaluated according to the following criteria.
  • Facial cleanser and whole body cleanser were manufactured according to the following formula. Both are hypoallergenic and have good foaming properties in all regions where the pH of the water used is 4-9, and in all regions where the hardness of the water used is 1-30 ° DH In addition, the foam quality was creamy, rinsing properties, good feeling after washing, and good stability.
  • the detergent composition with the composition shown in Table 2 is manufactured by mixing each component at 70 ° C (pH adjusted to 9), foaming property, foam quality, rinsing property, feel after washing, low irritation
  • the properties and stability were evaluated based on the same evaluation criteria as in Examples 1 to 8 and Comparative Examples 1 to 7. The results are shown in Table 2.
  • Laurin® salt 1 0.0 Myristin conversion K salt 7.0 0 Palmitic acid K salt 7.
  • Dipropylene glycol 1 0.0 Dipropylene glycol monooctyl ether 1. 0 Sorbit solution 1 0. 0 Sodium chloride 0.5 Ethylene glycol distearate 2.0 Methyl paraben 0.2 Propropyl paraben 0.1
  • Example 24 body shampoo
  • the face wash or body shampoos of Examples 23 to 25 are all mild, and the water used has a hardness of 1 to 30 ° in all regions where the pH of the water is 4 to 9. Even in all areas of DH, foaming is good, foam quality is creamy, rinsing, good feeling after washing and good stability was

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

Abstract

L'invention concerne une composition détergente qui est peu irritante pour la peau etc., et qui présente des propriétés moussantes, une mousse crémeuse, une sensation à l'utilisation (propriétés de rinçage et toucher de la peau lavée), et une stabilité excellentes. Composition détergente qui comprend (A) un tensioactif à base de phosphate comprenant un mélange de (a1) un tensioactif d'acide phosphorique monoester représenté par la formule générale (1) et (a2) un tensioactif d'acide phosphorique diester représenté par la formule générale (2), le rapport de (a1)/(a2) étant de l'ordre de 90/10 à 50/50 en poids, (B) un acide gras supérieur ou un sel de celui-ci représentés par la formule générale (3), et (C) au moins un élément choisi dans le groupe comprenant des éthers de glycéryle (C-1) présentant des groupes alkyle ou alcényle à chaîne linéaire ou ramifiée comportant 6 à 12 atomes de carbone et des composés (C-2) représentés par la formule générale (4), à condition que si le composant (C-1) est présent, le rapport en poids de (B)/(A) dépasse 1,5 et soit inférieur à 10.
PCT/JP2007/000376 2006-04-07 2007-04-06 Composition détergente WO2007122802A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020087024489A KR101353160B1 (ko) 2006-04-07 2007-04-06 세정제 조성물
CN2007800126050A CN101415810B (zh) 2006-04-07 2007-04-06 洗涤剂组合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2006106941A JP4705505B2 (ja) 2006-04-07 2006-04-07 洗浄剤組成物
JP2006106940 2006-04-07
JP2006-106940 2006-04-07
JP2006-106941 2006-04-07

Publications (1)

Publication Number Publication Date
WO2007122802A1 true WO2007122802A1 (fr) 2007-11-01

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ID=38624721

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/000376 WO2007122802A1 (fr) 2006-04-07 2007-04-06 Composition détergente

Country Status (3)

Country Link
KR (1) KR101353160B1 (fr)
CN (1) CN101415810B (fr)
WO (1) WO2007122802A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011190177A (ja) * 2010-03-11 2011-09-29 Kao Corp 皮膚外用剤組成物
JP2015003930A (ja) * 2014-10-08 2015-01-08 花王株式会社 皮膚外用剤組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08127798A (ja) * 1994-11-01 1996-05-21 Kao Corp 水系洗浄剤組成物
JPH09151399A (ja) * 1995-11-29 1997-06-10 Toho Chem Ind Co Ltd 洗浄剤組成物
JP2001107079A (ja) * 1999-10-12 2001-04-17 Kao Corp 洗浄剤組成物
JP2003313587A (ja) * 2002-04-25 2003-11-06 Kao Corp 洗浄剤組成物
JP2005314614A (ja) * 2004-04-30 2005-11-10 Kao Corp 洗浄剤組成物
JP2005314615A (ja) * 2004-04-30 2005-11-10 Kao Corp 洗浄剤組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR970011347B1 (ko) * 1993-09-24 1997-07-09 가오오, 가부시키가이샤 세정제 조성물
JP3813563B2 (ja) * 2002-03-12 2006-08-23 花王株式会社 洗浄剤組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08127798A (ja) * 1994-11-01 1996-05-21 Kao Corp 水系洗浄剤組成物
JPH09151399A (ja) * 1995-11-29 1997-06-10 Toho Chem Ind Co Ltd 洗浄剤組成物
JP2001107079A (ja) * 1999-10-12 2001-04-17 Kao Corp 洗浄剤組成物
JP2003313587A (ja) * 2002-04-25 2003-11-06 Kao Corp 洗浄剤組成物
JP2005314614A (ja) * 2004-04-30 2005-11-10 Kao Corp 洗浄剤組成物
JP2005314615A (ja) * 2004-04-30 2005-11-10 Kao Corp 洗浄剤組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011190177A (ja) * 2010-03-11 2011-09-29 Kao Corp 皮膚外用剤組成物
JP2015003930A (ja) * 2014-10-08 2015-01-08 花王株式会社 皮膚外用剤組成物

Also Published As

Publication number Publication date
CN101415810A (zh) 2009-04-22
KR20090007312A (ko) 2009-01-16
KR101353160B1 (ko) 2014-01-22
CN101415810B (zh) 2011-06-22

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