WO1992014809A1 - Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree - Google Patents

Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree Download PDF

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Publication number
WO1992014809A1
WO1992014809A1 PCT/EP1992/000330 EP9200330W WO9214809A1 WO 1992014809 A1 WO1992014809 A1 WO 1992014809A1 EP 9200330 W EP9200330 W EP 9200330W WO 9214809 A1 WO9214809 A1 WO 9214809A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkenyl
carbon atoms
radical
formula
Prior art date
Application number
PCT/EP1992/000330
Other languages
German (de)
English (en)
Inventor
Andreas Syldath
Karl Schmid
Ditmar Kischkel
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP92903962A priority Critical patent/EP0573448B1/fr
Priority to JP4503988A priority patent/JPH06505042A/ja
Priority to DE59202552T priority patent/DE59202552D1/de
Publication of WO1992014809A1 publication Critical patent/WO1992014809A1/fr

Links

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
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/66—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
    • 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
    • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups

Definitions

  • the invention relates to a process for the preparation of alkyl and / or alkenyl sulfate pastes with improved flowability by adding nonionic surfactants as viscosity reducers.
  • Anionic surfactants of the alkyl and alkenyl sulfate type especially those containing alkyl or alkenyl radicals with 16 to 18 carbon atoms, show excellent detergent properties and are suitable for the production of detergents, dishwashing detergents and cleaning agents.
  • alkyl and / or alkenyl sulfates in particular for the production of powder detergents, has hitherto been limited since the storage and transport of aqueous alkyl and / or alkenyl sulfate pastes is associated with serious problems.
  • alkyl and / or alkenyl sulfate pastes with solids contents of 30 to 70% by weight at ambient temperature have such a high viscosity and such a strong flow anomaly (rheopexy) that transferring or pumping around is practically impossible.
  • Mixing the pastes with other detergent ingredients also leads to largely inhomogeneous slurries that cannot be processed without problems.
  • the viscosity of alkyl aryl sulfate, alpha sulfofatty acid ester and alkyl sulfate pastes can be increased by adding 1 to 15% by weight, based on the surfactant content, of an adduct of 1 to 15 mol of ethylene - And / or propylene oxide on alcohols with 8 to 40 carbon atoms can be reduced to values below 10,000 mPa.s at 70 ° C.
  • This publication is primarily concerned with the viscosity control of alpha-sulfofatty acid ester salt pastes.
  • the object of the invention was therefore to provide a process for the preparation of alkyl and / or alkenyl sulfate pastes with improved flow properties which is free from the disadvantages described.
  • the invention relates to a process for the preparation of alkyl and / or alkenyl sulfate pastes with improved flow properties, which is characterized in that aqueous pastes of alkyl and / or alkenyl sulfates of the formula (I),
  • RI-O-SO3X in which R 1 is an alkyl and / or alkenyl radical having 10 to 22 carbon atoms and X is an alkali or alkaline earth metal which has a solids content of 30 to 70% by weight, at least one nonionic surfactant selected from the group formed by a) alkyl and / or alkenyl polyethylene glycol ether,
  • the selected nonionic surfactants to be used by the process according to the invention not only reduce the viscosity of alkyl and / or alkenyl sulfate pastes so much even at low temperatures that pumping around is possible without the risk of chemical decomposition, but also that Eliminate flow anomaly, which is a significant relief for the design of delivery pumps and delivery routes for the alkyl and / or alkenyl sulfate pastes.
  • the invention includes the knowledge that the addition of the nonionic surfactants makes it possible to produce homogeneous detergent slurries.
  • the washing, rinsing and cleaning ability of the alkyl and / or alkenyl sulfate pastes is not negatively influenced in the sense of the process according to the invention by the addition of the nonionic surfactants.
  • the pastes can be sprayed without pluming problems.
  • polyethylene glycol ethers with a narrow homolog distribution have proven to be particularly advantageous.
  • Alkyl and alkenyl sulfates are known anionic surfactants which can be obtained by the usual methods of preparative organic chemistry. As a rule, they are produced by reacting saturated and / or unsaturated, aliphatic primary alcohols with sulfur trioxide. Alkyl and / or alkenyl sulfates to which the process according to the invention extends are derived from fatty alcohols having 10 to 22 carbon atoms.
  • Typical examples are carpinal alcohol, Lauryl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol or erucyl alcohol.
  • alkyl sulfates which are derived from saturated fatty alcohols having 12 to 18, in particular 16 to 18, carbon atoms.
  • alkyl and / or alkenyl sulfates can also be derived from technical alcohol cuts, such as z. B. natural in the hydrogenation of technical fatty acid methyl esters
  • nonionic surfactants include a) alkyl and or alkenyl polyethylene glycol ethers,
  • Non-ionic surfactants which correspond to the formula (II) can be used as alkyl and / or alkenyl polyethylene glycol ethers (component a) in the process according to the invention:
  • R 2 -O- (CH 2 -CH 2 -O) n H (II) follow, in which R 2 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and n represents numbers from 2 to 7.
  • R 2 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and n represents numbers from 2 to 7.
  • alkyl and / or alkenyl polyethylene glycol ethers of the formula (II) can be used, the residual alcohol content of which, for example by distillation, has been reduced to a content of less than 1% by weight, based on the nonionic surfactant.
  • Component b) includes alkyl and / or alkenyl polypropylene glycol ethers of the formula (III)
  • R 3 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and m represents numbers from 1 to 4.
  • R 3 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and m represents numbers from 1 to 4.
  • R 3 represents a linear alkyl radical having 10 to 18 carbon atoms and m represents numbers from 1 to 3.
  • component c) come alkyl and / or alkenyl polypropylene glycol ethylene glycol ethers of the formula (IV)
  • R 4 represents a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms
  • p stands for numbers from 1 to 4
  • q stands for numbers from 1 to 10.
  • R 4 represents a linear alkyl radical having 10 to 18 carbon atoms
  • p represents 1 or 2
  • q represents numbers from 1 to 7.
  • the alkyl polyglycol ethers which form components a), b) and c), are addition products of ethylene and / or propylene oxide onto native fatty alcohols or synthetic oxo alcohols. Since the alkoxylation is a statistical reaction, the technical alkyl polyglycol ethers can homologs of different degrees of alkoxylation and unreacted Contain fatty alcohol. In the sense of the process according to the invention, both homologue-pure alkyl polyglycol ethers and technical mixtures, both with broad and narrow homolog distribution, can be used.
  • Component d) includes alkyl and / or alkenyl glycosides of the formula (V)
  • R 5 -O- (G) x (V) into consideration, in which R 5 represents an alkyl or alkenyl radical having 6 to 22 carbon atoms, G represents a glycose unit derived from a sugar having 5 or 6 carbon atoms and x stands for a number between 1 and 10.
  • the alkyl and / or alkenyl glycosides can moreover contain small amounts, depending on the production, but not more than 10% by weight, based on the alkyl and / or alkenyl glycoside, of alcohol.
  • alkyl glycosides of the formula (V) in which R 5 is is an alkyl radical having 10 to 18 carbon atoms, G is a glucose radical and x is a number from 1 to 3, in particular 1.1 to 1.6.
  • R 5 is an alkyl radical having 10 to 18 carbon atoms
  • G is a glucose radical
  • x is a number from 1 to 3, in particular 1.1 to 1.6.
  • R 6 represents an alkyl or alkenyl radical having 6 to 22 carbon atoms
  • R 7 represents an alkyl radical having 1 to 4 carbon atoms or a benzyl radical
  • R 8 represents hydrogen or a methyl group
  • y represents numbers from 1 to 10.
  • Preference is given to using mixed ethers of the formula (VI) in which R 6 is an alkyl radical having 12 to 18 carbon atoms, R 7 is a butyl or benzyl radical, R 8 is hydrogen and y is a number from 4 to 10.
  • R 9 represents an alkyl radical having 6 to 16 carbon atoms
  • R 10 represents an alkyl radical having 1 to 4 carbon atoms or a benzyl radical
  • R 11 represents hydrogen or a methyl group
  • z represents numbers from 1 to 10.
  • R 9 is an alkyl radical with 8 to 10 carbon atoms
  • R 10 represents a butyl or benzyl radical
  • R 11 represents hydrogen and z represents numbers from 4 to 10.
  • the nonionic surfactants can be added to the alkyl and / or alkenyl sulfate pastes individually or in combinations, the mixing ratio being able to vary over a wide range.
  • the use of a mixture containing polyglycol ethers, in particular alkyl polyethylene glycol ether, and alkyl glucosides in a weight ratio of 10:90 to 90:10, whose free alcohol content is less than 1% by weight, based on the mixture has proven particularly advantageous.
  • the nonionic surfactants can the alkyl and / or alkenyl sulfates in amounts of 1 to 15, preferably 5 to 12 wt .-% - based on the solids content of the Pastes - either added during or after neutralization.
  • the alkyl and / or alkenyl polyethylene glycol ether component a
  • alkyl and / or alkenyl sulfates can be mixed with the nonionic surfactants by mechanical means, for example by stirring or pumping, if appropriate at temperatures from 55 to 70 ° C .; there is no chemical reaction between the components.
  • mechanical means for example by stirring or pumping, if appropriate at temperatures from 55 to 70 ° C .; there is no chemical reaction between the components.
  • the anionic surfactant content and the unsulfonated contents were determined according to the DGF standard methods, Stuttgart, 1950-1984, H-III-10 and G-II-6b.
  • the sulfate content was calculated as sodium sulfate, the water content was determined according to the Fischer method. II. Viscosity of tallow alkyl sulfate / fatty alcohol polyethylene glycol ether mixture
  • V1 TA5 5.0 2,750 3,000 3,500 5,000 19,250
  • V3 TA14 5.0 3,000 3,000 4,000 6,000 41,000
  • V4 TA20 5.0 3,000 3,500 4,500 8,000 47,500
  • LS3 / LT5 mixture of an adduct of an average of 5 moles ethylene oxide with a C 12/14 - fatty alcohol un of an adduct of an average of 5 moles ethylene oxide with a C 12/18 fatty alcohol in a weight ratio 80: 20
  • TA5 adduct of 5 mol on average
  • TA20 adduct of 20 mol on average

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)

Abstract

On peut produire des pâtes de sulfate d'alkyle et/ou d'alcényle à fluidité améliorée par adjonction d'au moins un agent tensio-actif non ionique sélectionné dans le groupe formé par: (a) glycoléther de polyéthyle d'alkyle et/ou d'alcényle; (b) glycoléther de polypropylène d'alkyle et/ou d'alcényle; (c) éthylène glycoléther de polypropylèneglycol d'alkyle et/ou d'alcényle; (d) glucosides d'alkyle et/ou d'alcényle; (e) éthers mélangés et/ou (f) hydroxyéthers mélangés. La viscosité des pâtes de sulfate d'alkyle et/ou d'alcényle s'élève au maximum à 15 000 mPa.s à 55 °C.
PCT/EP1992/000330 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree WO1992014809A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP92903962A EP0573448B1 (fr) 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree
JP4503988A JPH06505042A (ja) 1991-02-25 1992-02-17 流動性を改良したアルキルおよび／またはアルケニルスルフェートペーストの製造方法
DE59202552T DE59202552D1 (de) 1991-02-25 1992-02-17 Verfahren zur herstellung von alkyl- und/oder alkenylsulfat-pasten mit verbesserter fliessfähigkeit.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4105851A DE4105851A1 (de) 1991-02-25 1991-02-25 Verfahren zur herstellung von alkyl- und/oder alkenylsulfat-pasten mit verbesserter fliessfaehigkeit
DEP4105851.8 1991-02-25

Publications (1)

Publication Number Publication Date
WO1992014809A1 true WO1992014809A1 (fr) 1992-09-03

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PCT/EP1992/000330 WO1992014809A1 (fr) 1991-02-25 1992-02-17 Procede de production de pates de sulfate d'alkyle et/ou d'alcenyle a fluidite amelioree

Country Status (7)

Country Link
EP (1) EP0573448B1 (fr)
JP (1) JPH06505042A (fr)
AT (1) ATE123801T1 (fr)
DE (2) DE4105851A1 (fr)
DK (1) DK0573448T3 (fr)
ES (1) ES2073288T3 (fr)
WO (1) WO1992014809A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007975A1 (fr) * 1992-09-25 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Pates de sulfate d'alkyle aqueuses coulantes
WO1994013770A1 (fr) * 1992-12-09 1994-06-23 Henkel Kommanditgesellschaft Auf Aktien Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides
WO1995008616A1 (fr) * 1993-09-23 1995-03-30 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents et produits de lavage ou de nettoyage a proprietes ameliorees de dissolution
WO1997004058A1 (fr) * 1995-07-20 1997-02-06 Henkel Kommanditgesellschaft Auf Aktien Melanges tensioactifs a solubilite amelioree de tensioactifs anioniques a base de sels sulfates d'alkyle a chaine longue, meme a de basses temperatures de bain
EP1191091A1 (fr) * 2000-09-20 2002-03-27 Cognis Deutschland GmbH Pâtes fluides et aqueuses contenant des sulfate d'alcools gras
EP0828748B2 (fr) † 1995-05-31 2003-09-03 Cognis Deutschland GmbH & Co. KG Procede de preparation d'alkyloligoglucosides peu visqueux de couleur claire

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6389884B1 (en) 1998-10-08 2002-05-21 Claas Selbstfahrende Erntemaschinen Gmbh Device and method for measuring the moisture of crop material in agricultural machines
DE19908563C2 (de) * 1999-02-27 2002-11-14 Cognis Deutschland Gmbh Reinigungsmittel für harte Oberflächen
DE102004015392A1 (de) * 2004-03-26 2005-10-20 Henkel Kgaa Maschinelles Geschirrspülmittel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084154A1 (fr) * 1981-12-28 1983-07-27 Henkel Kommanditgesellschaft auf Aktien Utilisation de régulateurs de viscosité pour concentrats tensio-actifs
EP0116905A2 (fr) * 1983-02-17 1984-08-29 Henkel Kommanditgesellschaft auf Aktien Utilisation de dérivés d'alcools comme régleurs de la viscosité pour des concentrés de tensio-actifs techniques hautement visqueux
WO1986002943A1 (fr) * 1984-11-06 1986-05-22 A.E. Staley Manufacturing Company Monoglycosides utilises en tant que modificateurs de viscosite dans des detergents
EP0259741A2 (fr) * 1986-09-08 1988-03-16 Henkel Kommanditgesellschaft auf Aktien Mélanges tensio-actifs et leur utilisation
WO1991004313A1 (fr) * 1989-09-14 1991-04-04 Henkel Corporation Compositions tensio-actives anioniques et amphoteres a viscosite reduite

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0084154A1 (fr) * 1981-12-28 1983-07-27 Henkel Kommanditgesellschaft auf Aktien Utilisation de régulateurs de viscosité pour concentrats tensio-actifs
EP0116905A2 (fr) * 1983-02-17 1984-08-29 Henkel Kommanditgesellschaft auf Aktien Utilisation de dérivés d'alcools comme régleurs de la viscosité pour des concentrés de tensio-actifs techniques hautement visqueux
WO1986002943A1 (fr) * 1984-11-06 1986-05-22 A.E. Staley Manufacturing Company Monoglycosides utilises en tant que modificateurs de viscosite dans des detergents
EP0259741A2 (fr) * 1986-09-08 1988-03-16 Henkel Kommanditgesellschaft auf Aktien Mélanges tensio-actifs et leur utilisation
WO1991004313A1 (fr) * 1989-09-14 1991-04-04 Henkel Corporation Compositions tensio-actives anioniques et amphoteres a viscosite reduite

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 98, no. 20, Mai 1983, Columbus, Ohio, US; abstract no. 162827, *
WORLD PATENTS INDEX LATEST Derwent Publications Ltd., London, GB; AN 86-097588 & JP,A,61 042 597 (KAO CORP.) 1. März 1986 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007975A1 (fr) * 1992-09-25 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Pates de sulfate d'alkyle aqueuses coulantes
WO1994013770A1 (fr) * 1992-12-09 1994-06-23 Henkel Kommanditgesellschaft Auf Aktien Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides
WO1995008616A1 (fr) * 1993-09-23 1995-03-30 Henkel Kommanditgesellschaft Auf Aktien Melanges detergents et produits de lavage ou de nettoyage a proprietes ameliorees de dissolution
US5668100A (en) * 1993-09-23 1997-09-16 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures and detergents or cleaning formulations with improved dissolving properties
EP0828748B2 (fr) † 1995-05-31 2003-09-03 Cognis Deutschland GmbH & Co. KG Procede de preparation d'alkyloligoglucosides peu visqueux de couleur claire
WO1997004058A1 (fr) * 1995-07-20 1997-02-06 Henkel Kommanditgesellschaft Auf Aktien Melanges tensioactifs a solubilite amelioree de tensioactifs anioniques a base de sels sulfates d'alkyle a chaine longue, meme a de basses temperatures de bain
EP1191091A1 (fr) * 2000-09-20 2002-03-27 Cognis Deutschland GmbH Pâtes fluides et aqueuses contenant des sulfate d'alcools gras

Also Published As

Publication number Publication date
DE4105851A1 (de) 1992-08-27
JPH06505042A (ja) 1994-06-09
DK0573448T3 (da) 1995-10-16
EP0573448B1 (fr) 1995-06-14
EP0573448A1 (fr) 1993-12-15
DE59202552D1 (de) 1995-07-20
ES2073288T3 (es) 1995-08-01
ATE123801T1 (de) 1995-06-15

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