Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
• • 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
  • C11D9/00—Compositions of detergents based essentially on soap
  • C11D9/005—Synthetic soaps
• • 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
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • 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
  • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
  • C11D1/29—Sulfates of polyoxyalkylene ethers
• • 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
  • C11D1/88—Ampholytes; Electroneutral compounds
  • C11D1/90—Betaines
• • 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
  • C11D10/00—Compositions of detergents, not provided for by one single preceding group
  • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
• • 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
  • C11D10/00—Compositions of detergents, not provided for by one single preceding group
  • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
  • C11D10/042—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
• • 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
  • C11D9/00—Compositions of detergents based essentially on soap
  • C11D9/002—Non alkali-metal soaps
• • 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
• • 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
  • A61K2800/74—Biological properties of particular ingredients
  • A61K2800/75—Anti-irritant
• • 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
  • C11D1/667—Neutral esters, e.g. sorbitan esters
• • 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
  • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

• the present invention relates to a body soap composition containing fatty acid soap and polyoxyethylene alkyl ether sulfate, in particular to a liquid soap excellent in use feeling at rinse and after washing owing to containing fatty acid soap and polyoxyethylene alkyl ether sulfate in a specific ratio, and especially relates to a facial cleanser.
• Polyoxyethylene alkyl ether sulfates anionic surface active agents, are widely used for body soaps because they show excellent foamability, cleansing power and comparatively low skin irritation.
• polyoxyethylene alkyl ether sulfate as a main component is that it is not easy to rinse after cleansing and that one who uses the soap feels slimy after rinse especially after washing one' s face.
• body soaps having an excellent use feeling during and after cleansing can be made by compounding fatty acid soap and polyoxyethylene alkyl ether sulfate in a specific ratio, and further excellent irritation reducing effect, foam stabilizing effect and cleansing power improving effect can be attained by adding thereto either amphoteric surface active agents such as betaine type amphoteric surface active agents or surface active agents selected from the group consisting of sorbitan type and polyethylene glycol type or both.
• amphoteric surface active agents such as betaine type amphoteric surface active agents or surface active agents selected from the group consisting of sorbitan type and polyethylene glycol type or both.
• the present invention relates to a body soap composition
• a body soap composition comprising 1 to 30% fatty acid soap and 1 to 30% polyoxyethylene alkyl ether sulfate by weight and the weight ratio of the fatty acid soap to the polyoxyethylene alkyl ether sulfate in the body soap composition is 8:2 to 3:7, and preferably 8:2 to 6:4.
• the higher fatty acid soaps are preferably prepared by neutralizing a mixture containing as main components lauric acid, myristic acid, palmitic acid and isostearic acid with triethanolamine, and the polyoxyethylene alkyl ether sulfates are preferably polyoxyethylene lauryl ether sulfate.
• amphoteric surface active agent in the body soap composition of the present invention, it is preferred to contain further 0.5 to 20% amphoteric surface active agent by weight.
• amphoteric surface active agents can be a betaine-type amphoteric surface active agents.
• the body soap composition is preferred to contain 0.1 to 5% nonionic surface active agent by weight.
• the nonionic surface active agents can be either sorbitan type or polyethylene glycol type nonionic surface active agents or both.
• the body soap compositions of the present invention can be used in a variety of forms and not restricted particularly but liquid type is preferable. A preferable application thereof is a facial cleanser.
• the fatty acid soap of the present invention is an alkaline salt of higher fatty acid represented by the general formula as follows:
• R 1 is an alkyl group having more than six carbon atoms
• M 1 is an alkaline group
• j and k are independently integers of 1 to 3.
• Examples of the higher fatty acids in the present invention can be caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, 12-hydroxystearic acid, undecylenic acid, lanolin fatty acid, linoleic acid, licinoleic acid and isostearic acid and so forth. They can be used as a mixture thereof having proper properties. Fats used for raw materials for preparation of the higher fatty acids are, for example, beef tallow, mutton tallow, palm oil, olive oil, castor oil, coconut oil, palm kernel oil and so forth, though the raw materials are not limited thereto.
• Said alkaline group can be sodium, potassium, ammonium (NH 4 ) cation and so forth, and in the present invention ammonium cation is preferred.
• the content of the fatty acid soap in the body soap composition of the present invention is 1 to 30% by weight. If no more than 1% by weight, cleansing power and foamability will not be enough. If exceeding 30% by weight, it is not preferred because of decrease in use feeling, increase in skin irritation and crystallization at low temperature in the case of liquid body soaps.
• Polyoxyethylene alkyl ether sulfates of the present invention are compounds shown by the general formula as follows:
• R 2 is an alkyl group having more than six carbon atoms
• M 2 is an alkaline group
• 1 is an integer from 1 to 30
• m and n are independently integers from 1 to 3.
• Polyoxyethylene alkyl ether sulfates anionic surface active agents, are generally prepared by sulfating polyoxyethylene derivatives of higher alcohols and then neutralizing with alkaline compound to form alkaline salts, but the preparation method in the present invention is not limited thereto.
• alkaline salts can be sodium salt, potassium salt, ammonium salt and so forth.
• Polyoxyethylene alkyl ether sulfates are widely used because they irritate skin less than alkyl ether sulfates .
• the content of the polyoxyethylene alkyl ether sulfates is 1 to 30% of the body soap composition by weight. If no more than 1% by weight, cleansing power and foamability are not enough. If exceeding 30% by weight, it is not preferable because of decrease in rinsing quality after use and remaining slimy feeling after rinse.
• polyoxyethylene alkyl ether sulfates can be polyoxyethylene octyl ether sulfate, polyoxyethylene lauryl ether sulfate, polyoxyethylene palmityl ether sulfate, polyoxyethylene stearyl ether sulfate, and so forth, especially polyoxyethylene lauryl ether sulfate such as sodium polyoxyethylene lauryl ether sulfate is preferred because of its low skin irritation.
• the form of the body soap of the present invention can be, for example, solids, semi-solids, foam or solutions, in particular solutions are preferred.
• amphoteric surface active agents can be a carbonic acid type such as aminoacid type and betaine type, sulfate type, sulfonic acid type, phosphate type, and so forth.
• betaine type amphoteric surface active agents are preferred.
• the betaine type amphoteric surface active agents can be, for example, N-alkyl-N- carboxymethyl ammonium betaine, sodium 2-alkyl-l-hydroxyethyl imidazoline betaine, alkyldimethylamino acetic acid betaine, alkylimidazolinium betaine and coconut oil fatty acid amide propyl betaine.
• amphoteric surface active agents other than the betaine type listed above are, for example, N- alkylaminoethyl glycine such as N-lauryl diamino ethyl glycine and N-myristyl diaminoethyl glycine, N-alkyl #-alanine, N,N,N- trimethyl amino propionic acid, N-hydroxyethyl N,N- dihydroxyethyl amino propionic acid, N-alkyl-N,N-dihydroxyethyl amino propionic acid, N,N,N-trihydroxyethyl amino propionic acid, N-alkyl N,N-dimethyl amino propionic acid, N-alkyl N,N- dihydroxyethylamino acetic acid, N-alkyl N,N-dimethyl amino acetic acid, N-alkyl N,N-dimethyl amino lactic acid, N-alkyl N,N- dimethyl amino propi
• amphoteric surface active agents can be contained independently or jointly.
• the contents of the amphoteric surface active agents are preferably from 0.5 to 20% of the body soap composition by weight. If no more than 0.5% by weight, preferred low irritation that should be realized by addition of an amphoteric surface active agent will not be attained. It is not preferable to exceed 20% by weight because of decrease in foamability of the body soap.
• nonionic surface active agents can be sugar fatty acid esters such as sucrose fatty acid ester, maltol fatty acid ester and lactose fatty acid ester; sugar alcohol fatty acid esters such as maltitol fatty acid ester and lactitol fatty acid ester; fatty acid polyglycerin esters such as decaglyceryl monolaurate and diglyceryl monostearate; fatty acid diethanol amides such as lauric acid mono- or di-ethanolamide and ⁇ tyristic acid mono- or di- ethanolamide; fatty acid monoglyceride.
• sugar fatty acid esters such as sucrose fatty acid ester, maltol fatty acid ester and lactose fatty acid ester
• sugar alcohol fatty acid esters such as maltitol fatty acid ester and lactitol fatty acid ester
• fatty acid polyglycerin esters such as decaglyceryl monolaurate and diglyceryl monostearate
• sorbitan type and polyethylene glycol type are particularly preferred.
• sorbitan type surface active agents polyoxyethylene coconut oil fatty acid sorbitan, sesguioleic acid sorbitan, trioleic acid sorbitan, monooleic acid sorbitan, onostearic acid sorbitan, monopalmitic acid sorbitan, monolauric acid sorbitan; and polyoxyethylene sorbitan fatty acid ester such as polyoxyethylene sorbitan monolaurate and polyoxyethylene sorbitan monostearate, and so forth, especially polyoxyethylene coconut oil fatty acid sorbitan is preferred.
• Preferred polyethylene glycol type nonionic surface active agents can be monooleic acid polyethylene glycol, monostearic acid polyethylene glycol, monolauric acid polyethylene glycol, distearic acid polyethylene glycol; polyoxyethylene fatty acid ester such as polyoxyethylene hydrogenated castor oil, polyoxyethylene polyoxypropylene copolymer, polyoxyethylene polyoxypropylene fatty acid esters and so forth. Distearic acid polyethylene glycol is especially preferred.
• the nonionic surface active agents can be used independently or jointly. The contents of the nonionic surface active agents are preferably from 0.1 to 5% of the body soap by weight. When no more than 0.1% by weight, sufficient foam stabilizing effect and cleansing power may not be attained. When exceeding 5% by weight, foamability may decrease.
• surface active agents can be sodium alkylsulfate such as sodium lauryl sulfate and sodium myristyl sulfate; sodium N-acyl zarcosinate such as sodium N-lauroil zarcosinate and sodium N-myristoil zarcosinate; sodium dodecylbenzene sulfonate, sodium hydrogenated coconut fatty acid monoglyceride monosulfate, sodium lauroilsulfoacetate, N- acylglutamate such as sodium N-palmitoil glutamate, sodium N- methyl-N-acyl taurine, sodium N-methyl-N-acylalanine, sodium a - olefine sulfonate and sodium dioctylsulfosuccinate.
• the above surface active agents can be contained either independently or jointly.
• the body soap of the present invention can further contain additives such as tackifiers, stabilizers, emulsifiers, moisturizers, antimicrobial agents, chelating agents, fragrances and so forth if not impairing the effects of the present invention.
• additives such as tackifiers, stabilizers, emulsifiers, moisturizers, antimicrobial agents, chelating agents, fragrances and so forth if not impairing the effects of the present invention.
• tackifiers can be electrolytes such as sodium chloride, potassium chloride and sodium sulfate; fatty acid polyethylene glycol esters such as monostearic acid polyethylene glycol and distearic acid polyethylene glycol; alkylol amides such as coconut oil fatty acid diethanol amide and polyoxyethylene coconut oil fatty acid monoethanol amide; cellulose derivatives such as methyl cellulose and hydroxyethyl cellulose.
• the tackifiers can be contained either independently or jointly.
• Stabilizers can be included in order to improve solution stability at low temperatures especially in the case of transparent body soaps.
• the stabilizers can be alcohols such as ethanol, propylene glycol and glycerine, sodium benzenesulfonate, sodium xylenesulfonate, urea, etc.
• the stabilizers can be contained either independently or jointly.
• emulsifiers can be opalizers such as styrene polymer and polyvinylacetate, magnesium stearate, ethylene glycol monostearate, ethylene glycol distearate, stearyl alcohol, pearly brighteners such as fish scales, titanium mica and oxychlorobismus treated mica. Those emulsifiers can be contained either independently or jointly.
• moisturizers can be higher alcohols such as cetanol and stearyl alcohol, lanoline derivatives, glycerine sorbit, propylene glycol, ethylene glycol, 1,3-butylene glycol, polyethylene glycol, polypropylene glycol. These moisturizers can be contained either independently or jointly.
• the germicides are often compounded not only for sterilization, disinfection and deodorization but also in order to prevent dermatitis such as pimple as well as skin cleaning. Some of them can be contained for medically effective ingredients or antiseptic agents.
• the examples of the germicides can be cresols such as meta-cresol and para-chloro-meta-cresol, chlorhexidine, isopropyl methyl phenol, photosensitizer 101, chloroxylenol, trichlorocarbanilide, halocarban, phenol, trichrosan, phenoxyethanol, etc. Above germicides can be contained either independently or jointly.
• Chelating agents are often used to improve clearness of transparent liquid body soaps or to prevent decrease in transparency caused by formation of metallic soap.
• Examples of the chelating agents can be ethylene diamine tetraacetate derivatives, tripolyphosphates, hexametaphosphates, dihydroxy ethylglycine, citric acid, tartaric acid, gluconic acid and saccharic acid.
• the chelating agents can be contained either independently or jointly.
• fragrances can be menthol, anethole, carvone, eugenol, limonene, ocimene, n-decylalcohol,citronellol, alpha-terpineol, methyl salicylate, methyl acetate, citronellyl acetate, cineole, linalool, ethyl linalool, vanillin, thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon leaf oil, perilla oil, wintergreen oil, clove oil, eucalyptus oil, etc. They can be contained either singly or in combination.
• Subjects cleanse their face using test samples and evaluate foamability and slimy feeling after rinse according to below criteria.
• the test results are average values of the evaluations of all the subjects.
• Results of the above two tests are scored as X:0, ⁇ :l, 0:2, and ®:3, the scores of the two tests for each sample are added and the sums are the combined evaluations. Samples whose combined evaluations are more than 4 are regarded as "good” and less than 3 "defective".
• Examples 1 to 3 Comparative Examples l and 2: As shown in Table 1, five samples were prepared by mixing fatty acid soap (prepared by neutralizing a mixture of fatty acids comprising lauric acid, myristic acid, palmitic acid and isostearic acid with triethanol amine) and sodium polyoxyethylene lauryl ether sulfate so that the ratios of the fatty acid soap to sodium polyethylene lauryl ether sulfate in the samples were 0:10, 3:7, 5:5, 7:3 and 10:0 respectively.
• fatty acid soap prepared by neutralizing a mixture of fatty acids comprising lauric acid, myristic acid, palmitic acid and isostearic acid with triethanol amine
• 154g purified water in a glass beaker of 500ml was heated up to about 70 ° C in a water bath. Except for comparative examples 1 and 2, fatty acid soaps were prepared by adding fatty acid and triethanolamine directly to the glass beaker so that the weight of formed soap became equivalent to the composition ratio shown in Table 1, and then sodium polyoxyethylene lauryl ether sulfate corresponding to the composition ratio shown in Table 1 was added to the aqueous solution.
• comparative example 1 46g sodium polyoxyethylene lauryl ether sulfate was charged to a 154 g purified water, the mixed aqueous solutions were agitated with a stirrer while cooling until the solutions became uniform, then stopped agitation, cooled the solutions to a room temperature and stored as the test samples.
• Sensual evaluation tests were performed for twenty subjects using five test samples shown in Table 1. The results showed that, in the test of foamability at use, samples of composition weight ratios in the range from 3:7 to 7:3 were evaluated as good. In the test of slimy feeling after rinse, the composition ratios in the range from 3:10 to 10:0 were evaluated as good, in particular the ratio 7:3 was considered as ⁇ , the best evaluation in Table 1. Consequently samples of ratios in the range from 3:7 to 7:3 were evaluated as good in both tests of foamability and slimy feeling as well as the combined evaluations, and were found that they had good use feeling.
• Facial cleanser having compositions shown in Table 3 were prepared according to the following procedures:
• 260g purified water was poured into a one litter glass beaker, heated up to 70 C, while agitating ingredients shown in Table 3 were charged sequentially to the glass beaker, the solution was agitated for more than ten minutes with a stirrer till the solution became uniform, agitation was stopped, and the solution was stood and cooled to the room temperature.
• samples for facial cleanser compositions were prepared in a similar process to the samples in Table 3 in compositions shown in below Table 4 whose ratios of fatty acid soap to sodium polyoxyethylene lauryl ether sulfate were 6:4, 7:3, 8,2 and 9:1.
• a body soap in the present invention containing 1 to 30% fatty acid soap and 1 to 30% polyoxyethylene alkyl ether sulfate by weight whose weight ratio of the fatty acid soap to the polyoxyethylene alkyl ether sulfate being in the range of 8:2 to 3:7 has an excellent use feeling such as foamability at use and slimy feeling after rinse.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
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• Animal Behavior & Ethology (AREA)
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• Detergent Compositions (AREA)
• Cosmetics (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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• 1996
  • 1996-01-25 JP JP8030130A patent/JPH09202898A/ja active Pending
• 1997
  • 1997-01-22 NZ NZ325938A patent/NZ325938A/en unknown
  • 1997-01-22 AU AU13194/97A patent/AU716758B2/en not_active Ceased
  • 1997-01-22 CN CN97193058A patent/CN1117848C/zh not_active Expired - Fee Related
  • 1997-01-22 WO PCT/JP1997/000121 patent/WO1997027279A1/en not_active Application Discontinuation
  • 1997-01-22 CA CA002244670A patent/CA2244670C/en not_active Expired - Fee Related
  • 1997-01-22 KR KR1019980705732A patent/KR19990082012A/ko not_active Application Discontinuation
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  • 1997-01-22 EP EP97900743A patent/EP0885288A1/en not_active Ceased

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