EP0670878A1 - Preparations tensio-actives visqueuses aqueuses - Google Patents

Preparations tensio-actives visqueuses aqueuses

Info

Publication number
EP0670878A1
EP0670878A1 EP93923556A EP93923556A EP0670878A1 EP 0670878 A1 EP0670878 A1 EP 0670878A1 EP 93923556 A EP93923556 A EP 93923556A EP 93923556 A EP93923556 A EP 93923556A EP 0670878 A1 EP0670878 A1 EP 0670878A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
weight
formula
atoms
radical
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
EP93923556A
Other languages
German (de)
English (en)
Inventor
Dieter Nickel
Rainer Hofmann
Hermann Hensen
Claudia Panzer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0670878A1 publication Critical patent/EP0670878A1/fr
Ceased legal-status Critical Current

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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/92—Sulfobetaines ; Sulfitobetaines

Definitions

  • the invention relates to low-concentration and highly viscous aqueous surfactant preparations which contain alkyl glycosides and certain amphoteric surfactants and / or cationic surfactants, a process for their preparation and the use of such preparations as detergents or cleaning agents.
  • alkyl glycosides with long-chain alkyl groups belong to the nonionic surfactants.
  • the person skilled in the art also knows, for example in A.M. Schwartz, J.W. Perry, Surface Active Agents, Vol. I, Interscience Publishers, 1949, page 372, describe that surfactant mixtures generally have synergistic effects and often have better cleaning properties than would result from the sum of the values of the individual components .
  • Aqueous liquid detergents which contain alkyl glycosides and 12 to 30% of a surface-active betaine in combination with a customary anionic surfactant are described in European patent application EP 341 071.
  • Liquid detergents which contain water, 1 to 50% by weight of an organic solvent and 5 to 50% by weight of a mixture of alkyl glycoside and anionic surfactant or optionally zwitterionic surfactant in a weight ratio of 1:10 to 10: 1 known from European patent application EP 070 074.
  • European patent application EP 094 118 detergents are known which contain alkyl glycosides together with optionally further nonionic surfactants and cationic surfactants in a weight ratio of 2: 1 to 12: 1.
  • the detergent or cleaning agent precursors based on alkyl glycoside mentioned in these documents are relatively highly concentrated aqueous solutions or pastes, since the components intended for mixing into finished agents should have the highest possible active substance content. At the same time, they must be easy to handle, which means that they should have the lowest possible viscosity, flow and be easy to pump.
  • aqueous liquid products used by the consumer which include in particular liquid detergents, dishwashing detergents and universal cleaners, but also cosmetic products, for example hair shampoos or body cleaning lotions, are subject to a certain minimum viscosity, although the active substance content of such products is generally relative is low.
  • Such products therefore normally contain thickeners, which generally have the disadvantage of not contributing to the cleaning performance of the surfactant component contained in the agents themselves.
  • Typical thickeners are inorganic water-soluble salts, in particular sodium chloride, and salts of non-surface-active aromatic sulfonic acids, for example sodium cumene sulfonate.
  • Organic thickeners are usually fatty acid alkanolamides, such as coconut fatty acid monoethanolamide, lauric acid monoethanol amide, oleic acid diethanolamide and coconut fatty acid diethanolamide, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • fatty acid alkanolamides such as coconut fatty acid monoethanolamide, lauric acid monoethanol amide, oleic acid diethanolamide and coconut fatty acid diethanolamide, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • the surfactant preparations according to the invention are accordingly gel-like aqueous
  • R * is an alkyl radical having 8 to 22 carbon atoms
  • G is a glycose unit
  • n is a number between 1 and 10, 0.05% by weight to 6% by weight of a thickener in the form of a cationic surfactant of the formula II
  • R2 is an alkyl or alkenyl radical with 10 to 22 carbon atoms and up to 3 CC double bonds
  • R ⁇ is an alkyl radical with 1 to 3 carbon atoms
  • X is an anion, preferably a halide anion, and / or an amphoteric surfactant of the formula III,
  • R 4 is hydrogen or an alkyl or hydroxyalkyl radical with 1 to
  • R ⁇ is an alkyl radical having 1 to 3 carbon atoms or the part (R ⁇ N is an optionally C-alkylated imidazoline radical, n is a number from 1 to
  • 22 and Y represent a carboxylate or sulfonate group, the weight ratio of alkyl glycoside according to formula I to thickener being 35: 1 to 1: 1, preferably 15: 1 to 8: 1, and to 100% by weight of water or a mixture consist of water with a water-miscible organic solvent.
  • gel-like preparations are understood to mean structured, isotropic, viscoelastic solutions with a visco-elastic network structure which is composed of rod micelles. They preferably have a viscosity, measured at a temperature in the range from 20 ° C. to 25 ° C. at a shear rate of 30 s "*, from 400 mPa-s to 10000 mPa-s, in particular from 500 mPa-s to 8000 mPa-s, on.
  • the alkyl glycoside preparations according to the invention preferably contain 3% by weight to 11% by weight, in particular 4% by weight to 8% by weight, of alkyl glycoside according to formula I, 0.075% by weight to 2.5% by weight, in particular 0.1% to 2% by weight of thickener according to formula II and / or III and per 100% by weight of water.
  • Some of the water, in particular not more than 5% by weight, based on the preparation according to the invention, can be mixed with a water-miscible organic solvent, preferably from the group comprising alcohols with 1 to 4 carbon atoms, glycols with 2 to 4 carbon atoms and the di- and triglycols derived therefrom and the corresponding glycol ethers and mixtures of these substances.
  • Another object of the invention is a process for the preparation of storage-stable, gel-like surfactant preparations on an aqueous basis which have a viscosity in the range of 400 mPa at a temperature in the range from 20 ° C. to 25 ° C. at a shear rate of 30 s -1 . s to 10,000 mPa.s by mixing an alkyl glycoside of the formula I which is optionally present in aqueous solution,
  • R 1 is an alkyl radical having 8 to 22 carbon atoms
  • G is a glycose unit and n is a number between 1 and 10
  • a thickener in the form of a cationic surfactant of the formula II
  • R 2 is an alkyl or alkenyl radical with 10 to 22 C atoms and up to 3 CC double bonds
  • R 3 is an alkyl radical with 1 to 3 C atoms
  • X is an anion, preferably a halide anion, and / or an amphoteric surfactant of formula III
  • R ⁇ is hydrogen or an alkyl or hydroxyalkyl radical having 1 to 3 C atoms
  • R ⁇ is an alkyl radical with 1 to 3 C atoms or the part (R5)
  • N is an optionally C-alkylated imidazoline radical
  • n is a number of 1 to 22
  • Y represent a carboxylate or sulfonate group, in the weight ratio of alkyl glycoside according to formula I to thickening agent from 35: 1 to 1: 1, and with so much water or a mixture of water with a water-miscible organic solvent that the Total surfactant content in the preparation is 2.2% to 22% by weight.
  • the procedure is preferably such that an aqueous paste which contains alkyl glycoside according to formula I in a concentration of 30% by weight to 60% by weight in such an amount with the cationic and / or a photosidic thickener or whose aqueous solution mixes, that the sum of the surfactants in the resulting aqueous preparation is in the range mentioned and in particular is 2.5% by weight to 10% by weight and the resulting gel is 88% by weight to 97.8 % By weight, in particular 90% by weight to 97.5% by weight of water.
  • the water can be admixed at any point in the preparation of the agents according to the invention if the starting materials used do not already contain sufficient such solvent.
  • the components are preferably heated to temperatures of 60 ° C. to 80 ° C. and mixed with conventional mixers, which are preferably heatable and are kept during the entire mixing process, in particular at temperatures in the range mentioned.
  • alkyl glycosides suitable for the surfactant preparations according to the invention and their preparation are described, for example, in European patent applications EP 92355, EP 301 298, EP 357 969 and EP 362 671 or the US Pat. No. 3547828.
  • the glycoside components ((G) n in formula I) of such alkyl glycosides are oligomers or polymers from naturally occurring aldose or ketose monomers, in particular glucose, mannose, fructose, galactose, talose, gulose, altrose , Allose, Idose, Ribose, Arabinose, Xylose and Lyxose.
  • the oligomers consisting of such glycosidically linked monomers are characterized not only by the type of sugar they contain, but also by their number, the so-called degree of oligomerization.
  • the degree of oligomerization (n in formula I) can also take non-integer numerical values as the quantity to be determined analytically; it is generally between 1 and 10, for the alkyl glycosides which are preferably used below 3, in particular between 1.2 and 1.4.
  • the preferred monomer building block is glucose because of its good availability.
  • the alkyl part (R * in formula I) of the alkyl glycosides contained in the surfactant preparations according to the invention preferably also originates from easily accessible derivatives of renewable raw materials, in particular from fatty alcohols.
  • alcohols although their branched chain isomers, in particular so-called oxo alcohols, can also be used for the preparation of alkyl glycosides which can be used.
  • the primary alcohols with linear octyl, decyl, dodecyl, tetradecyl, hexadecyl or octa-decyl radicals and mixtures thereof are particularly useful.
  • the alkyl glycosides can contain small amounts, for example 1 to 2%, of unreacted free fatty alcohol due to the production process, which generally " does not have a disadvantageous effect on the properties of the preparations produced therewith.
  • the cationic surfactants of the formula (II) which can be used in the context of the invention preferably have a long-chain alkyl radical R 2 having 10 to 24 C atoms, in particular 12 to 18 C atoms. This can be branched or straight-chain, the linear primary alkyl radicals, in particular the primary decyl, dodecyl, tetradecyl, hexadecyl or ⁇ octadecyl radicals and mixtures thereof, being preferred.
  • the short-chain radical R 3 is preferably a propyl, ethyl or methyl group, compounds with the latter being particularly preferred.
  • the anion X can be a sulfate, methosulfate or ethosulfate or a halide. It is preferably a chloride or bro id.
  • amphoteric surfactants according to formula (III) are derivatives of tertiary or quaternary amines which have at least one straight-chain or branched aliphatic radical, one of which carries a carboxyl or sulfato group.
  • amphoteric surfactants are N, N-dimethyl-N-tetradecyl-glycine, N, N-dimethyl-N-hexadecyl-glycine, N, N-dimethyl-N-octadecyl-glycine, 3- (dimethyl-dodecylammonio) -l-propanesulfonate and the amphoteric surfactants sold under the names Dehyton (R) AB, CB and G (manufacturer Hen ⁇ kel).
  • imidazoline derivatives derived formally from aminocarboxylic acids, for example 4-aminobutyric acid or glycine, for example the 2 -Alkyl-N-carboxymethyl-N-hydroxyalkyl-imidazoline betaines, in which the alkyl group has 7 to 18 carbon atoms and the hydroxyalkyl group is a hydroxyethyl or hydroxypropyl group.
  • aminocarboxylic acids for example 4-aminobutyric acid or glycine
  • 2 -Alkyl-N-carboxymethyl-N-hydroxyalkyl-imidazoline betaines in which the alkyl group has 7 to 18 carbon atoms and the hydroxyalkyl group is a hydroxyethyl or hydroxypropyl group.
  • amphoteric surfactants which can be used according to the invention.
  • the amphoteric surfactants preferably contain as little as possible, in particular not more than 5% by weight, based on amphoteric surfactant, of inorganic salt.
  • amphoteric surfactants include the alkali metal chlorides and in particular the alkali metal sulfates. If salt contents in such low amounts are not already obtained during the production of the amphoteric surfactants, the ether sulfate can be reduced to contents not exceeding 5% by weight, in particular from 0.1% by weight to 1, by known methods, for example by recrystallization. 5 parts by weight, based on amphoteric surfactant, of inorganic salt.
  • the surfactant preparations according to the invention have excellent cleaning properties and high solubility in cold water. They are therefore preferably used as washing, rinsing or cleaning agents and in particular in hair and body care or serve as storage-stable, easy-to-use premixes for the production of such agents.
  • builder substances such as zeolites and layered silicates, corrosion inhibitors, bleaching agents, bleach activators, optical brighteners, enzymes, graying inhibitors, antimicrobial active substances, abrasive agents, foam stabilizers, Preservatives, pH regulators, opacifiers and pearlescent agents, colorants and fragrances and additional surfactants are possible among the preparations according to the invention.
  • Table 1 Properties of 5% by weight preparations (25 ° C)
  • Viscosity [% by weight] [mPa.s]
  • Viscosity [% by weight] [mPa.s]
  • Viscosity [% by weight] [mPa.s]

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

Abstract

Pour des formulations aqueuses faiblement concentrées contenant 2 à 20 % en poids d'un alkylglucoside de formule R1-O(G)n, dans laquelle R1 désigne un reste alkyle avec 8 à 22 atomes de C, G une unité glucose et n un nombre de 1 à 10, on se propose d'améliorer la facilité de manipulation dans certaines conditions d'utilisation et on se fixe comme objectif que la formulation contienne des quantités aussi faibles que possible d'une substance active ne comportant pas d'alkylglucoside. Cet objectif a été atteint essentiellement par l'addition, en vue d'accroître la viscosité, de 0,05 à 6 % en poids d'un tensioactif cationique de formule R2-N(R33X, dans laquelle R2 désigne un reste alkyle ou un reste alcényle avec 10 à 22 atomes de C et jusqu'à trois liaisons doubles C-C, R3 désigne un reste alkyle avec 1 à 3 atomes de C et X désigne un anion, et/ou par l'addition d'un tensioactif ampholyle de formule R4(R5)2N-(CH2)n-Y, dans laquelle R4 désigne hydrogène ou un reste alkyle ou hydroxyalkyle avec 1 à 3 atomes de C, R5 désigne un reste alkyle avec 1 à 3 atomes de C, ou la partie (R5)2N désigne un reste imidazoline éventuellement carboalkylé, n représente un nombre de 1 à 22 et Y désigne un groupe carboxylate ou sulfonate, le rapport en poids de l'alkylglucoside à l'épaissisant étant de 35:1 à 1:1.
EP93923556A 1992-11-26 1993-10-26 Preparations tensio-actives visqueuses aqueuses Ceased EP0670878A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19924239677 DE4239677A1 (de) 1992-11-26 1992-11-26 Viskose wäßrige Tensidzubereitungen
DE4239677 1992-11-26
PCT/EP1993/002962 WO1994012602A1 (fr) 1992-11-26 1993-10-26 Preparations tensio-actives visqueuses aqueuses

Publications (1)

Publication Number Publication Date
EP0670878A1 true EP0670878A1 (fr) 1995-09-13

Family

ID=6473648

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93923556A Ceased EP0670878A1 (fr) 1992-11-26 1993-10-26 Preparations tensio-actives visqueuses aqueuses

Country Status (4)

Country Link
EP (1) EP0670878A1 (fr)
JP (1) JPH08503719A (fr)
DE (1) DE4239677A1 (fr)
WO (1) WO1994012602A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6071429A (en) * 1992-09-21 2000-06-06 Henkel Corporation Viscosity-stabilized amide composition, methods of preparing and using same
DE19933404A1 (de) * 1999-07-21 2001-01-25 Henkel Kgaa Reinigungsmittel für harte Oberflächen
EP1894989A1 (fr) * 2006-09-01 2008-03-05 The Procter and Gamble Company Composition pâteuse pour articles sanitaires

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USH269H (en) * 1985-03-11 1987-05-05 A. E. Staley Manufacturing Company Disinfectant and/or sanitizing cleaner compositions
US4668422A (en) * 1985-05-31 1987-05-26 A. E. Staley Manufacturing Company Liquid hand-soap or bubble bath composition
US4804497A (en) * 1985-09-26 1989-02-14 A. E. Staley Manufacturing Company Fine fabric detergent composition
DE4009616A1 (de) * 1990-03-26 1991-10-02 Henkel Kgaa Fluessige koerperreinigungsmittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9412602A1 *

Also Published As

Publication number Publication date
WO1994012602A1 (fr) 1994-06-09
JPH08503719A (ja) 1996-04-23
DE4239677A1 (de) 1994-06-01

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