WO2008023610A1 - Préparation externe à usage cutané - Google Patents

Préparation externe à usage cutané Download PDF

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Publication number
WO2008023610A1
WO2008023610A1 PCT/JP2007/065851 JP2007065851W WO2008023610A1 WO 2008023610 A1 WO2008023610 A1 WO 2008023610A1 JP 2007065851 W JP2007065851 W JP 2007065851W WO 2008023610 A1 WO2008023610 A1 WO 2008023610A1
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WO
WIPO (PCT)
Prior art keywords
skin
group
mass
external preparation
water
Prior art date
Application number
PCT/JP2007/065851
Other languages
English (en)
Japanese (ja)
Inventor
Satoru Takayama
Noriko Mori
Makoto Takeuchi
Original Assignee
Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
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 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo filed Critical Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority to JP2008530869A priority Critical patent/JPWO2008023610A1/ja
Publication of WO2008023610A1 publication Critical patent/WO2008023610A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the present invention relates to a skin external preparation, and more particularly, to a water based skin external preparation containing dissolved cyanine pigments.
  • Photosensitive Element No. 101 and Photosensitive Element No. 201 are well known which have bactericidal and antiseptic properties. Although these are compounds that have been used for many years, they exhibit remarkable bactericidal and antiseptic action at low concentrations, and also have side effects and disorders that should be noted at normal concentrations.
  • the benefits that have not been invited have been changed and are still frequently used in a wide variety of external preparations for skin (for example, JP 9-291021, JP 2002-356414, JP 5-36404, No. 2772445, No. 2881333 and supervision by Masaaki Hayami, “Photosensitive dye”, pages 135 to 172, published on October 17, 1997, published by Sangyo Tosho Co., Ltd.).
  • cyanine dyes such as Photosensitive Element 101 and Photosensitive Element 201 are that they are difficult to dissolve in water and that they are easily decomposed, discolored, and precipitated in an aqueous solution. Therefore, when such cyanine dye is applied to a water-based skin external preparation such as lotion, for example, the ability to combine an organic solvent such as ethanol with the substrate, and in some cases In some cases, the application of the dye itself had to be abandoned.
  • an object of the present invention is to provide an external preparation for skin containing water as a base material and containing a cyanine dye in a stable manner over a long period of time.
  • HLB value hydrophilic / lipophilic balance value
  • the present invention relates to water as a base material, a cyanine dye represented by the general formula 1 or 2 dissolved in water as the base material, and a nonionic property having an HLB value of 12 or more.
  • the problem is solved by providing an external preparation for skin comprising a surfactant.
  • R and R represent the same or different aliphatic hydrocarbon groups
  • Those aliphatic hydrocarbon groups may have a substituent.
  • X— represents an appropriate anion.
  • R to R represent the same or different aliphatic hydrocarbon groups
  • Those aliphatic hydrocarbon groups may have a substituent.
  • the present invention provides the above skin external preparation, with respect to 1 part by mass of cyanine dye.
  • the problem is solved by providing an external preparation for skin containing 0.1 part by mass or more of a nonionic surfactant dissolved therein.
  • the present invention solves the above-mentioned problems by providing a skin external preparation comprising one or a plurality of moisturizing agents dissolved in the skin external preparation.
  • a nonionic surfactant having an HLB value of 12 or more
  • the cyanine dye represented by the general formula 1 or 2 promotes the dissolution of the cyanine dye in the base water and stabilizes the cyanine dye in the aqueous solution. It is desirable to mix the desired amount of the cyanine dye represented by the general formula 1 or 2 with the water-based skin external preparation that is undesirable due to decomposition of the water! There are real benefits that can be made Furthermore, since the skin external preparation of the present invention is essentially based on water, for example, there is concern about the sensitive reaction of the skin to organic solvents frequently used in cosmetics such as ethanol. There is a profit that can be used continuously for a long time.
  • the present invention provides water as a base material, a cyanine dye represented by the general formula 1 or 2 dissolved in water as the base material, and an HLB value of 12
  • the present invention relates to an external preparation for skin comprising the above nonionic surfactant.
  • R to R are the same or different aliphatic hydrocarbon groups.
  • the aliphatic hydrocarbon group in 1 5 is linear or branched having up to 20 carbon atoms, usually having up to 12 carbon atoms, such as methyl, ethyl, propyl, isopropyl, isopropenyl Group, 1 propenyl group, 2-propenyl group, 2-propynyl group, butyl group, isobutyl group, sec butyl group, tert butyl group, 2-buturyl group, 1,3-butadienyl group, pentyl group, Isopentyl group, neopentyl group, tert pentyl group, 1-methylpentyl group, 2 methylpentyl group, 2 pentyl group, 2 pentene-4-linole group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group Octyl group, noel group, decyl group, undecyl group, dodecyl
  • one or more of its hydrogen atoms are in a hydroxy group, or, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group without departing from the object of the present invention.
  • cyanine dyes represented by the general formulas 1 and 2 those having two or more similar cyclic groups in the molecule and each of these cyclic groups each having an aliphatic hydrocarbon group In terms of ease of preparation, these aliphatic hydrocarbon groups are conveniently the same as each other.
  • X— or X— in the general formulas 1 and 2 are the same or different appropriate anions.
  • Examples of the individual anions include fluorine ion, chlorine ion, bromine ion, iodine ion, perchlorate ion, perbromate ion, periodate ion, nitrate ion, sulfate ion, phosphate ion, borate ion, etc.
  • iodine ion is particularly preferable because it has a self-sterilizing / preserving ability.
  • Examples of such cyanine dyes include those represented by chemical formulas 1 to 10. All of these are microorganisms that should be eliminated to keep the skin healthy without causing substantial damage to the skin, such as Aspergillus, Escherichia, Candida, Corynebacterium, and Syudomonas. Demonstrates remarkable bactericidal ability against microorganisms of the genera, Staphylococcus and Bacillus.
  • the cyanine dyes represented by the chemical formulas 1 to 10 those represented by the chemical formulas 2 and 7 have a particularly strong bactericidal and antiseptic ability, and when a nonionic surfactant described later is present together, This is particularly preferable because it exhibits practically no problem!
  • the cyanine dyes represented by the chemical formulas 2 and 7 are products named “Capionin” (Photosensitive Element 201) and “Platinin” (Photosensitive Element 101), which are compatible with cosmetics and quasi-drugs, respectively. Sold by name!
  • the nonionic surfactant referred to in the present invention means an atomic group that does not ionically dissociate in water and forms an oxonium bond with a water molecule, such as a hydroxy group, an oxy group, a force rubamoyl group, an alkoxy group. Or the like in the molecule, and the HLB value is 12 or more, preferably 14 or more.
  • nonionic surfactants include propylene glycol monofatty acid ester, ethylene glycol monofatty acid ester, glycerin monofatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, and trehalose fatty acid ester.
  • Polyhydric alcohol fatty acid esters and polyhydric alcohol alkyl ethers such as methyl dalcoside fatty acid ester and alkyl polydarcoside, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene phytosterol, Polyoxyethylene phytostanol, polyoxyethylene cholesterol, polyoxyethylene cholestanol, polyoxyethylene polyoxypropylene alkyl ester Ether, polyoxyethylene such as polyoxyethylene polyoxypropylene glycol Ethers, polyoxyethylene mono fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene methyl dalcoside fatty acid esters, poly Oxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyoxyethylene animal and vegetable oils, ether esters such as polyoxyethylene alkyl ether fatty acid esters, polyoxyethylene
  • the proportion of the nonionic surfactant dissolved in the base water together with the cyanine dyes represented by the general formulas 1 and 2 is based on 1 part by mass of the cyanine dye. 0.1 to 1 part by mass, preferably 1 to 1,000 parts by mass, more preferably 5 to 500 parts by mass. If the ratio of the nonionic surfactant to 1 part by mass of cyanine dye is less than 0.1 part by mass, when added to water together with cyanine dye, the desired dissolution promotion and stabilization cannot be achieved, and 1, If the amount exceeds 000 parts by mass, the effect will reach its peak, so it is usually desirable to adjust it within the above range.
  • the proportion of nonionic surfactant should be reduced. It is preferable to set it high, and the use of the topical skin preparation moisturizes the skin, suppresses rough skin, and keeps the skin fresh and smooth. In the case of an astringent lotion to prevent makeup loss, it is preferable to set the ratio of the nonionic surfactant conservatively.
  • concentration of the cyanine dye represented by the general formulas 1 and 2 in the external preparation for skin according to the present invention is usually 0.002% by mass or less for cosmetics, and for quasi-drugs. Over 0.002% by mass and up to 0.005% by mass.
  • the external preparation for skin according to the present invention is, within the range not departing from the object of the present invention, depending on the use of the external preparation for skin, other disinfecting and preservatives that are substantially soluble in water as a base material, , Moisturizers such as glycerin, propylene glycolanol, dipropylene glycol, 1,3-butylene glycol, polyethylene glycolole, sonorebitole, manoletithonole, trenosulose, sodium hyanorelonate, sodium chondroitin sulfate, carboxybutyl polymer, xanthan gum, Water-soluble polymers such as pullulan, pullulan derivatives, cellulose derivatives, sodium hyaluronate, ⁇ -glycyrrhetinic acid, dipotassium glycyrrhizinate, allantoin, azulene, ⁇ - aminocaproic acid, oxidized lysozyme and
  • Melanin production inhibitors melanin reducing agents, melanin excretion promoters, cooling agents, hormonal agents, antihistamines, plant extracts, animal extracts, UV inhibitors, antioxidants, cell activators, blood flow, commonly used in the field It does not interfere with the appropriate blending of accelerators, sebum suppressants, stratum corneum peeling / dissolving agents, antiperspirants, deodorants, propellants, masking agents, coloring agents, and fragrances.
  • the external preparation for skin of the present invention which contains one or more moisturizers such as 1,3-butylene glycol, maltitol, trehalose, sodium hyaluronate, sodium chondroitin sulfate and the like. Is extremely useful as a skin lotion to keep the skin clean and healthy.
  • the external preparation for skin according to the present invention is used in combination with the cyanine dye and the nonionic surfactant as described above with respect to water as a base material, depending on the use, if necessary. It can be obtained by adding one or more ingredients other than the above, and dissolving and adding them with appropriate heating and stirring.
  • the obtained aqueous solution may be used as it is.
  • insoluble materials are usually removed by filtration, etc., sterilized by heating or microfiltration, filled into containers such as cans, bottles, etc. To do.
  • the external preparation for skin according to the present invention can be used for general lotions such as soft lotions, cleansing lotions, astringent lotions and the like for cleansing and keeping the skin healthy.
  • aqueous raw material with antibacterial and antiseptic properties for the preparation of quasi-drugs such as cosmetics such as basic cosmetics, acne skin cosmetics, hair cosmetics, shampoos, rinses, and mouthwashes other than water Useful.
  • a nonionic surfactant having an HLB value of 12 or more Based on experimental examples, the agent promotes the dissolution of the cyanine dyes represented by the general formulas 1 and 2 in the base water and stabilizes the cyanine dyes in the aqueous solution. To do.
  • photosensitizers 201 and 101 which are cyanine dyes represented by the chemical formulas 2 and 7, are named Hayashibara Biochemical Research Co., Ltd. under the product names Pionin and Platonin, respectively.
  • polyoxyethylene (20) cetyl ether polyoxyethylene (20) sorbitan monostearate
  • polyoxyethylene which are non-ionic surfactants with an HLB value of 12 or more.
  • control test samples 1 and 9 in which the nonionic surfactant was omitted and replaced with the same mass of purified water, and polyoxyethylene (nonionic surfactant with an HLB value of 10.5) ( 5.5) Reference test samples 6 and 14 prepared using cetyl ether, and dipolyoxy, which is an anionic surfactant having an HLB value of 17.0 instead of a nonionic surfactant. Control test samples prepared with either ethylene (10) lauryl ether phosphate or polyoxyethylene (15) stearamide, a cationic surfactant with an HLB value of 18.0 7, 8, 15 and 16 were prepared.
  • test samples 1 to 16 were left in an environment with a relative humidity of 75% at 40 ° C for 3 months, during which time each test sample was near the absorption maximum of cyanine dye immediately before the start and after the end of the test.
  • the absorbance of each test sample was measured, and the absorbance obtained immediately after the standing was divided by the absorbance obtained immediately before the standing was obtained to obtain the residual ratio of cyanine dye (%).
  • the solubility of the cyanine dye, discoloration, and the presence of precipitation were determined by observing each test sample with the naked eye immediately before the start and after the end of the leave.
  • the light blue aqueous solution of the present invention 99 Good solubility
  • the HLB value is the same as Photosensitive Element 101 or Photosensitive Element 201
  • polyoxyethylene (5.5) cetyl ether which is a nonionic surfactant having an HLB value of 10.5
  • dipolyethylene (10) lauryl ether phosphoric acid which is an anionic surfactant having an HLB value of 17.0
  • test samples having the same composition as in test samples 1 and 9 were prepared except that a mixture of purified water and ethanol (volume ratio 3: 1) was used. As a result, the solubility was extremely good, and at the end of 3 months, no discoloration of the cyanine dye was observed, but the residual ratio of cyanine dye was slightly low at about 80%.
  • the topical skin preparation of this example which contains a cyanine dye having a disinfecting and antiseptic ability stably dissolved over a long period of time, is a lotion other than a lotion to cleanse and keep the skin healthy and other than the lotion.
  • a lotion other than a lotion to cleanse and keep the skin healthy and other than the lotion.
  • it is useful as an aqueous raw material with antibacterial and antiseptic properties for preparing quasi-drugs such as basic cosmetics, cosmetics for acne skin, and cosmetics for hair, shampoos, rinses, and mouthwashes. It is.
  • any of the cyanine dyes represented by Chemical Formulas 1 to 10 is dissolved to a concentration of 0.002% by mass. It was. Thereafter, the obtained clear aqueous solution was sterilized by membrane filtration according to a conventional method, thereby obtaining 10 types of external preparations for skin.
  • the topical skin preparations of the present example which exhibit a significant moisturizing action on the skin and stably dissolve and contain a cyanine dye having antibacterial and antiseptic properties over a long period of time, It is useful as a skin lotion that keeps the skin healthy while keeping it healthy, moisturizing the skin, suppressing rough skin.
  • the following components were dissolved with heating and stirring, and then one of the cyanine dyes represented by the chemical formulas 1 and 10 was dissolved in the aqueous solution so as to have a concentration of 0.002% by mass. Thereafter, the obtained clear aqueous solution was sterilized by membrane filtration according to a conventional method to obtain 10 types of external preparations for skin.
  • the topical skin preparation of this example which exhibits a significant moisturizing effect on the skin and stably dissolves and contains a cyanine dye having antibacterial and antiseptic properties over a long period of time, A skin lotion that keeps the skin healthy while keeping it healthy, moisturizing the skin, reducing rough skin And useful.
  • the topical skin preparation of the present invention is used in the field of cosmetics and quasi-drugs to cleanse and keep the skin healthy, for example, lotions such as soft lotion, cleansing lotion, and astringent lotion.
  • Aqueous raw materials with antibacterial and antiseptic properties for the preparation of quasi-drugs such as basic cosmetics, acne skin cosmetics, hair cosmetics, shampoos, rinses, mouthwashes, etc. Useful as.

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention porte sur une préparation externe à usage cutané pouvant contenir un colorant cyanine à l'état dissous pendant une durée importante en dépit de l'inclusion d'eau au titre de matériau de base. La préparation externe comprend de l'eau au titre de matériau de base, un colorant cyanine spécifique dissous dans l'eau (matériau de base) et un tensioactif nonionique d'indice d'équilibre hydrophile/hydrophobe supérieur ou égal à 12.
PCT/JP2007/065851 2006-08-24 2007-08-14 Préparation externe à usage cutané WO2008023610A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008530869A JPWO2008023610A1 (ja) 2006-08-24 2007-08-14 皮膚外用剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-228232 2006-08-24
JP2006228232 2006-08-24

Publications (1)

Publication Number Publication Date
WO2008023610A1 true WO2008023610A1 (fr) 2008-02-28

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ID=39106696

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Application Number Title Priority Date Filing Date
PCT/JP2007/065851 WO2008023610A1 (fr) 2006-08-24 2007-08-14 Préparation externe à usage cutané

Country Status (3)

Country Link
JP (1) JPWO2008023610A1 (fr)
TW (1) TW200817043A (fr)
WO (1) WO2008023610A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013057608A (ja) * 2011-09-09 2013-03-28 Shimadzu Corp 粒子径測定装置
CN103910693A (zh) * 2014-03-31 2014-07-09 上海鲁冠生物科技有限公司 双噻唑季铵盐的合成方法
JP2015030667A (ja) * 2013-07-31 2015-02-16 株式会社ノエビア 感光素２０１号含有弱酸性水性外用組成物
JP2015151379A (ja) * 2014-02-18 2015-08-24 株式会社ノエビア 水性クレンジング料

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60179431A (ja) * 1983-11-14 1985-09-13 Shiseido Co Ltd 感光素２０１号含有組成物
JPS63130520A (ja) * 1986-11-18 1988-06-02 Lion Corp 口腔用組成物
JPH03148208A (ja) * 1989-11-02 1991-06-25 Mikimoto Seiyaku Kk 皮膚外用剤
JPH049317A (ja) * 1990-04-27 1992-01-14 Sunstar Inc 美白化粧料
JPH06321734A (ja) * 1993-05-18 1994-11-22 Shiseido Co Ltd メーキャップ化粧料
JPH1045563A (ja) * 1996-08-08 1998-02-17 Noevir Co Ltd 抗菌性低刺激化粧料
JPH10182335A (ja) * 1996-12-20 1998-07-07 Noevir Co Ltd 抗菌性低刺激化粧料
JPH10203954A (ja) * 1997-01-20 1998-08-04 Noevir Co Ltd 抗菌性低刺激化粧料
JP2002114670A (ja) * 2000-10-02 2002-04-16 Noevir Co Ltd 抗菌性皮膚外用剤
JP2003335621A (ja) * 2002-05-16 2003-11-25 Noevir Co Ltd 抗菌性低刺激化粧料

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60179431A (ja) * 1983-11-14 1985-09-13 Shiseido Co Ltd 感光素２０１号含有組成物
JPS63130520A (ja) * 1986-11-18 1988-06-02 Lion Corp 口腔用組成物
JPH03148208A (ja) * 1989-11-02 1991-06-25 Mikimoto Seiyaku Kk 皮膚外用剤
JPH049317A (ja) * 1990-04-27 1992-01-14 Sunstar Inc 美白化粧料
JPH06321734A (ja) * 1993-05-18 1994-11-22 Shiseido Co Ltd メーキャップ化粧料
JPH1045563A (ja) * 1996-08-08 1998-02-17 Noevir Co Ltd 抗菌性低刺激化粧料
JPH10182335A (ja) * 1996-12-20 1998-07-07 Noevir Co Ltd 抗菌性低刺激化粧料
JPH10203954A (ja) * 1997-01-20 1998-08-04 Noevir Co Ltd 抗菌性低刺激化粧料
JP2002114670A (ja) * 2000-10-02 2002-04-16 Noevir Co Ltd 抗菌性皮膚外用剤
JP2003335621A (ja) * 2002-05-16 2003-11-25 Noevir Co Ltd 抗菌性低刺激化粧料

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013057608A (ja) * 2011-09-09 2013-03-28 Shimadzu Corp 粒子径測定装置
JP2015030667A (ja) * 2013-07-31 2015-02-16 株式会社ノエビア 感光素２０１号含有弱酸性水性外用組成物
JP2015151379A (ja) * 2014-02-18 2015-08-24 株式会社ノエビア 水性クレンジング料
CN103910693A (zh) * 2014-03-31 2014-07-09 上海鲁冠生物科技有限公司 双噻唑季铵盐的合成方法

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JPWO2008023610A1 (ja) 2010-01-07
TW200817043A (en) 2008-04-16

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