EP0489777B1 - Agents antimousse resistant aux alcalis - Google Patents

Agents antimousse resistant aux alcalis Download PDF

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Publication number
EP0489777B1
EP0489777B1 EP90912683A EP90912683A EP0489777B1 EP 0489777 B1 EP0489777 B1 EP 0489777B1 EP 90912683 A EP90912683 A EP 90912683A EP 90912683 A EP90912683 A EP 90912683A EP 0489777 B1 EP0489777 B1 EP 0489777B1
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EP
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Prior art keywords
weight
mol
general formula
decanol
hexyl
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Expired - Lifetime
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EP90912683A
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German (de)
English (en)
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EP0489777A1 (fr
Inventor
Karl-Heinz Schmid
Karin Koren
Detlev Stanislowski
Michael Langen
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • C11D1/721—End blocked 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
    • C11D1/66—Non-ionic compounds
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • 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
    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates

Definitions

  • the invention relates to the use of selected mixtures of end-capped and on the other hand not end-capped polyethylene glycol ethers as alkali-stable and homogeneously formulated foam-suppressing additives in low-foam detergents in aqueous, highly concentrated alkali solutions.
  • the active substance mixtures according to the invention are particularly suitable as anti-foaming agents for bottle cleaning and for so-called cleaning-in-place (CIP) cleaning.
  • CIP cleaning-in-place
  • the invention aims to provide tools of the type mentioned which combine high effectiveness with physiological harmlessness and biodegradability.
  • the invention is also based on the object to enable optimization of the performance profile of the auxiliaries used in practical use, on the one hand, but on the other hand to provide selected polyethylene glycol ethers of the type mentioned, which ensures improved formulation of these auxiliaries in commercially available concentrate form.
  • foam-suppressing aids is mostly due to the fact that the detached from the substrates and in the cleaning baths accumulating impurities act as foaming agents.
  • the cleaning agents themselves can also contain constituents which give rise to undesirable foaming under the given working conditions.
  • anionic surfactants are widely used anionic surfactants.
  • DE-OS 38 00 493 (D 8113) describes the use of polyethylene glycol ethers of the general formula (I) given above, but now in this formula R 1 is a straight-chain or branched alkyl or alkenyl radical having 20 to 28 carbon atoms, R2 is an alkyl radical with 4 to 8 carbon atoms and n is a number from 6 to 20.
  • R 1 is a straight-chain or branched alkyl or alkenyl radical having 20 to 28 carbon atoms
  • R2 is an alkyl radical with 4 to 8 carbon atoms
  • n is a number from 6 to 20.
  • the crucial modification here is the use of longer chain residues R 1.
  • These end group-capped polyglycol ethers are also characterized by high alkali and acid stability. Their foam-preventing effect in alkaline and neutral cleaning liquors is specified in the Strengthens the senses, moreover they also meet the legal requirements for biodegradability.
  • nonionic surfactants based on polyglycol ether compounds cannot easily be incorporated into aqueous, strongly alkaline formulations. They easily form a separate phase from the aqueous phase and therefore require the use of solubilizers.
  • Known effective solubilizers, especially especially for strongly alkaline cleaning formulations, are alkyl mono- and / or oligoglucosides, which must also be a preferred class of substances in the given context for ecological reasons.
  • EP-A2-0 202 638 describes a liquid cleaning concentrate for strongly alkaline cleaning formulations consisting of end group-capped fatty alcohol glycol ether compounds with mixed oligoalkoxide residues together with a combination of three solubilizers which are intended to ensure homogeneous formulation in strongly alkaline aqueous solutions.
  • One of these solubilizers used is alkyl mono- and / or alkyl polyglucosides with 8 to 12 carbon atoms in the alkyl radical and 1 to 6 glucose units. Also in US Pat. No.
  • an alkaline detergent concentrate for washing bottles is an aqueous concentrate containing 10 to 35% by weight of alkali metal hydroxide, 10 to 50% by weight of a mixture of a polyoxypropylene-polyoxyethylene condensate, an etherified ethoxylated alcohol and one Alkylglucosids described. It is a disadvantage, particularly in the context of this last-mentioned teaching, that these preparations foam too much during practical use, in particular through the use of the alkylglucoside. In addition, phase separations occur at high alkali contents.
  • the teaching of the present invention is based on the task, by fine tuning and optimizing the selection of the polyethylene glycol ether compounds used, to obtain mixtures which are distinguished by particularly high-quality effects when used as anti-foaming agents, and this effect optimization both at comparatively low temperatures - So, for example, in the range of about 20 ° C - as well as at the elevated temperatures usually used in practice in the range of about 60 to 70 ° C.
  • the invention further aims to enable the formulation of these auxiliaries in strongly alkaline, highly concentrated aqueous solutions to form single-phase systems. This single-phase formulability should be ensured over the temperature range that is essential in practice, for example from about 20 to 70 ° C.
  • the teaching of the invention is based on the knowledge that the joint use of two structurally similar but not structurally identical polyethylene glycol compounds in cooperation with the alkyl glucosides leads to the desired optimization if at the same time the constitutional features defined below for the construction of the respective type of polyethylene glycol ether -Connections are observed.
  • compounds of the general formula (II) in which the R5O- radical is derived from alkanols or alkanol mixtures which, for determining the R1O- radical, are derived from the general formula ( I) have previously been defined as subclasses (2a), (2b), (2c) and / or (2d).
  • compounds of the general formula (II) can also be used here which are derived from 2-butyloctanol-1, 2-butyldecanol-1 and / or 2-hexyloctanol-1 with respect to their radical R5O-.
  • the active ingredients or active ingredient mixtures for (2) and (3) of the general formulas (I) and (II) are present together with the alkylglucosides. If desired, the active ingredient components to numbers (4) - d. H. the end group-capped polyethylene glycol ether compounds of the general formula (III) -, alkali metal salts of cumene sulfonate and / or xylene sulfonate and also deionized water.
  • the reaction takes place, for example, at temperatures from 200 to 300 ° C. and leads to branched Guerbet alcohols which have branching in the 2 position to the hydroxyl group.
  • the invention predominantly or preferably exclusively uses straight-chain fatty alcohols for the preparation of the 2-branched Guerbet alcohols and ultimately for the synthesis of the compounds of the general formula (I). It is known that fatty alcohols of natural origin have at least largely predominantly even chain lengths, so that their 2-branched Guerbet alcohol with 18 C atoms cannot be obtained as a uniform condensation product of only one selected fatty alcohol via their dimerization.
  • the necessary dimerization of a mixture of the two fatty alcohols with 8 and 10 C atoms leads to the isomer mixture of the 18 C Guerbet alcohol from 2-hexyldodecanol-1 and 2-octyldecanol-1.
  • the condensation products of the two alcohols used arise with themselves, ie the 2-hexyldecanol-1 from the octanol used and the 2-octyldodecanol-1 from the decanol used.
  • end group-capped - but also those not capped with end groups - fatty alcohol polyglycol ethers of the formula (I) or of the formula (II) are prepared in accordance with the specifications of DE-OS 33 15 951. This is advantageously done the fatty alcohols of higher carbon number described above with ethylene oxide in a molar ratio of 1: 5 to 1: 9 or 1: 2 to 1: 5 ⁇ m and, if desired, then etherify the hydroxyl groups present in the reaction product obtained.
  • the reaction with ethylene oxide takes place under the known alkoxylation conditions, preferably in the presence of suitable alkaline catalysts.
  • the etherification of the free hydroxyl groups is preferably carried out under the known conditions of Williamson's ether synthesis using straight-chain or branched C4- to C8-alkyl halides.
  • the n-butyl radical for the radical R2 from the general formula (I) is of particular importance in the course of the inventive action. Examples of such a final etherification are accordingly n-butyl halides such as n-butyl chloride.
  • the invention is not limited to this. Further examples are amyl halides, hexyl halides and the higher alkyl halides in the range mentioned.
  • Compounds of the general formula (III) are prepared analogously.
  • alkyl halide and alkali in a stoichiometric excess, for example from 10 to 50%, over the hydroxyl groups to be etherified.
  • the cleaning agents in which the partially end-capped polyglycol ether mixtures of the invention are used can contain the constituents customary in such agents, such as wetting agents, builders and complexing agents, alkalis or acids, corrosion inhibitors and optionally also organic solvents.
  • the surfactants used are non-ionic surface-active compounds of the polyglycol ether type which are obtained by adding ethylene oxide to alcohols, in particular fatty alcohols, alkylphenols, fatty amines and carboxamides, and anionic surfactants such as alkali metal, amine and alkylolamine salts of fatty acids, alkylsulfuric acids, alkylsulfonic acids and alkylbenzenesulfonic acids Consideration.
  • alcohols in particular fatty alcohols, alkylphenols, fatty amines and carboxamides
  • anionic surfactants such as alkali metal, amine and alkylolamine salts of fatty acids, alkylsulfuric acids, alkylsulfonic acids and alkylbenzenesulfonic acids Consideration.
  • the cleaning agents can be builders and complexing agents, in particular alkali metal orthophosphates, polymer phosphates, silicates, borates, carbonates, polyacrylates and gluconates, as well as citric acid, nitrilotriacetic acid, ethylenediaminetetraacetic acid, 1-hydroxyalkane-1,1-diphosphonic acid and ethylenediphosphonic acid and ethylene Phosphonoalkane polycarboxylic acids, e.g. B. phosphonobutane tricarboxylic acid and alkali metal salts of these acids.
  • Highly alkaline cleaning agents especially those for bottle cleaning, contain considerable amounts of caustic alkali in the form of sodium and / or potassium hydroxide.
  • the cleaning agents can contain organic solvents, for example alcohols, gasoline fractions and chlorinated hydrocarbons as well as free alkylolamines.
  • storage-stable active ingredient mixtures which are foamable and preferably liquid in the temperature range from about 20 to 60 ° C. and which, for example, contain 5 to 30% by weight of the active ingredient concentrates from the components ( 1) to (3) and, if desired, additionally (4) to (6) together with 70 to 95% by weight of concentrated aqueous alkali metal hydroxide solutions.
  • These alkali hydroxide solutions can be aqueous sodium and / or potassium hydroxide solutions with an alkali hydroxide content of at least 30% by weight, in particular at least 40% by weight.
  • Suitable is, for example, aqueous approximately 50% sodium hydroxide solution as the main part of a formulation according to the invention, which is stable in storage up to approximately 70 ° C. as a homogeneously clear aqueous solution.
  • polyglycol ether mixtures to be used according to the invention give effective effects even in low concentrations.
  • Such detergents are preferred in such quantities added that their concentration in the ready-to-use solutions is approximately in the range of 50 to 500 ppm.
  • the foam attenuation of the additives selected according to the invention - and, in comparison, structurally similar additives but not within the scope of the invention - is determined using a test method which is described as follows:
  • the defoaming effect is tested under the following conditions: 300 ml of a 1% strength by weight aqueous sodium hydroxide solution are heated to 20 ° C. or 65 ° C. in a double-walled 2 liter measuring cylinder. 0.1 ml of the defoaming surfactant to be determined is added to this solution. With the help of a peristaltic pump, the liquid is circulated at a rate of 4 l / min. pumped around. The test liquor is approx.
  • a 1% by weight aqueous solution of the triethanolamine salt of tetrapropylene benzene sulfonate is used as the test foam. This is metered in at intervals of one minute in amounts of 1 ml each of the liquor in circulation. The resulting total volume of foam and liquid is determined.
  • the foam-inhibiting effect of the surfactant material used in each case is all the better the longer the period of time required to reach the 2000 ml mark in the measuring cylinder due to the total volume of the liquid and foam phases.
  • the respective are corresponding Numerical values for this time are given in minutes or in ml of test foamers.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne l'utilisation d'un mélange de substances actives contenant éventuellement de l'eau en quantités limitées et composées de (en % en poids relativement au mélange): 1) 5 à 30 % en poids d'alkylglglucosides à base d'alcools gras avec 6 à 12 atomes de C avec un degré de glucosidation de 1 à 2 environ; 2) 5 à 70 % en poids de composés de polyéthylèneglycol-éthers fermés dans les groupes terminaux, de formule générale (I): R1O-(CH2CH2O)n-R2, dans laquelle le résidu R1O- provient d'alcanols pairs ramifiés en position 2 avec 16 à 20 atomes de C, le résidu R2 désigne un résidu alkyle avec 4 à 8 atomes de C et n un nombre de 5 à 9; 3) 5 à 70 % en poids de composés de polyéthylèneglycol-éthers non fermés dans les groupes terminaux, de formule générale (II) R5O-(CH2CH2O)z-H, dans laquelle le résidu R5O- provient d'alcanols pairs ramifiés en position 2 avec 12 à 20 atomes de C et z désigne un nombre de 2 à 5 et éventuellement; 4) 0 à 70 % en poids de composés de polyéthylèneglycol-éthers fermés dans les groupes terminaux, de formule générale (III): R3O-(CH2CH2O)m-R4, dans laquelle R3 désigne un résidu alkyle linéaire avec 8 à 18 atomes de C ou un résidu alkyle ramifié avec 8 à 14 atomes de C, R4 un résidu alkyle avec 4 à 10 atomes de C et m un nombre de 5 à 15; 5) 0 à 5 % en poids de sulfonate de cumène alcalin et/ou de sulfonate de xylène alcalin; 0 à 70 % en poids d'eau déminéralisée, comme concentré de substance active antimousse formulable, résistant aux alcalis et aqueux pour des produits de lavage peu moussants.

Claims (5)

  1. Utilisation d'un mélange de principes actifs contenant en quantités limitées éventuellement de l'eau, à base (% en poids rapporté respectivement au mélange de principes actifs) de :
    1) 5 à 30 % en poids d'alcoylglucoside à base d'alcools gras en C₆ à C₁₂ avec un degré de glucosidation d'environ 1 à 2.
    2) 5 à 70 % en poids de composés d'éthers de polyéthylèneglycol bloqués sur les groupes terminaux de formule générale (I).



            R₁O-(CH₂CH₂O)n-R₂   (I)



    dans laquelle le reste R₁O dérive d'alcanols ramifiés en position 2 en nombre pair ayant de 16 à 20 atomes de C, le reste R₂ signifie un radical alcoyle ayant de 4 à 8 atomes de C et n signifie un nombre allant de 5 à 9.
    3) 5 à 70 % en poids de composés d'éthers de polyéthylèneglycols non bloqués sur les groupes terminaux, de formule générale (II)



            R₅O-(CH₂CH₂O)z-H   (II)



    dans laquelle le reste R₅O dérive d'alcanols ramifiés en 2 en nombre pair, ayant de 12 à 20 atomes de C, et z est un nombre allant de 2 à 5.
    4) 0 à 70 % en poids de composés d'éthers de polyéthylèneglycol bloqués aux groupes terminaux de formule générale (III).



            R₃O-(CH₂CH₂O)m-R₄   (III)



    dans laquelle R₃ signifie un radical alcoyle linéaire ayant de 8 à 18 atomes de C, ou un radical alcoyle ramifié ayant de 8 à 14 atomes de C R₄ signifie un radical alcoyle ayant de 4 à 10 atomes de carbone et m est un nombre allant de 5 à 15.
    5) 0 à 5 % en poids de cumène sulfonate alcalin et/ou de xylène sulfonate alcalin ainsi que :
    6) 0 à 70 % d'eau déminéralisée
    en tant que concentré de substances actives qui réprime la mousse, que l'on peut formuler d'une manière stable en milieu aqueux alcalin pour des agents de nettoyage pauvres en mousse.
  2. Mode d'exécution selon la revendication 1, caractérisé en ce que des composés d'éther de polyéthylèneglycol de formule générale I sont mis en jeu, dans lesquels le reste R₁O- dérive des mélanges d'alcools suivants (a) ou (b) :
    a) 10 à 100 % molaire d'un mélange équimolaire d'isomères à base de 2-hexyldodécanol-1 et de 2-octyldécanol-1
    0 à 90 % molaire de 2-hexyldécanol-1
    0 à 50 % molaire de 2-octyldodécanol-1
    ou
    b) 40 à 70 % molaire de 2-hexyldécanol-1
    60 à 30 % molaire de 2-octyldodécanol-1
    et n signifie un nombre allant de 5 à 9.
  3. Mode d'exécution selon les revendications 1 et 2, caractérisé en ce que les mélanges d'éther de polyéthylèneglycol de formule générale (I) sont mis en jeu, leurs restes R₁O- dérivent de mélanges d'alcools de composition suivante :
       au moins 45 % molaire du mélange d'isomères à base
       de 2-hexyldodécanol-1 et de 2-octyldécanol-1
       0 à 55 % molaire de 2-hexyldécanol-1 pas plus de 30 % molaire de 2-octyldodécanol.
  4. Mode d'exécution selon les revendications 1 à 3, caractérisé en ce que l'on met en jeu des composés d'éthers de polyéthylèneglycol de formule générale (II), dans lesquels le reste R₅O-, dérive d'au moins un des alcanols suivants :
    2-butyloctanol-1, 2-butyldécanol-1, 2-hexyloctanol-1, 2-hexyldécanol-1, 2-hexyldodécanol-1, 2-octyldécanol-1 et/ou 2-octyldodécanol-1.
  5. Compositions stables au stockage, aqueuses-alcalines, liquides clairs de préférence dans la zone de températures allant d'environ 20 à 60°C, de mélanges de principes actifs réprimant la mousse qui contiennent :
    5 à 30 % en poids de concentré de principe actif selon les revendications 1 à 4 et
    70 à 95 % en poids de solution d'hydroxyde alcalin, aqueuse concentrée ayant des teneurs en MeOH (Me=sodium et/ou potassium) préférées d'au moins 30 % en poids, en particulier d'au moins 40 % en poids.
EP90912683A 1989-08-30 1990-08-21 Agents antimousse resistant aux alcalis Expired - Lifetime EP0489777B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3928602A DE3928602A1 (de) 1989-08-30 1989-08-30 Alkalistabile und stark alkalisch formulierbare antischaummittel fuer die gewerbliche reinigung, insbesondere fuer die flaschen- und cip-reinigung
DE3928602 1989-08-30
PCT/EP1990/001382 WO1991003538A1 (fr) 1989-08-30 1990-08-21 Agents antimousse resistant aux alcalis

Publications (2)

Publication Number Publication Date
EP0489777A1 EP0489777A1 (fr) 1992-06-17
EP0489777B1 true EP0489777B1 (fr) 1994-04-27

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EP90912683A Expired - Lifetime EP0489777B1 (fr) 1989-08-30 1990-08-21 Agents antimousse resistant aux alcalis

Country Status (7)

Country Link
US (1) US5205959A (fr)
EP (1) EP0489777B1 (fr)
JP (1) JPH05500074A (fr)
CA (1) CA2065334A1 (fr)
DE (2) DE3928602A1 (fr)
ES (1) ES2052268T3 (fr)
WO (1) WO1991003538A1 (fr)

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DE3723323C2 (de) * 1987-07-15 1998-03-12 Henkel Kgaa Hydroxy-Mischether, Verfahren zu deren Herstellung sowie deren Verwendung
DE3727378A1 (de) * 1987-08-17 1989-03-02 Henkel Kgaa Schaumdrueckende zusaetze in schaumarmen reinigungsmitteln
DE3800490A1 (de) * 1988-01-11 1989-07-20 Henkel Kgaa Verwendung ausgewaehlter endgruppenverschlossener fettalkoholethoxylate fuer schaumarme, kalt spritzbare reinigungsmittel
DE3800493A1 (de) * 1988-01-11 1989-07-20 Henkel Kgaa Verwendung von polyglykolethern als schaumdrueckende zusaetze in schaumarmen reinigungsmitteln, die insbesondere auch fuer die kaltreinigung geeignet sind
JPH01213564A (ja) * 1988-02-23 1989-08-28 Japan Gore Tex Inc 感湿素子およびその製造法
DE3818062A1 (de) * 1988-05-27 1989-12-07 Henkel Kgaa Schaumdrueckende alkylpolyglykolether fuer reinigungsmittel (i)
DE3818014A1 (de) * 1988-05-27 1989-11-30 Henkel Kgaa Schaumdrueckende alkylpolyglykolether fuer reinigungsmittel (ii)

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DE3928602A1 (de) 1991-03-07
CA2065334A1 (fr) 1991-03-01
EP0489777A1 (fr) 1992-06-17
JPH05500074A (ja) 1993-01-14
WO1991003538A1 (fr) 1991-03-21
US5205959A (en) 1993-04-27
DE59005551D1 (de) 1994-06-01
ES2052268T3 (es) 1994-07-01

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