EP0673409A1 - Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides - Google Patents

Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides

Info

Publication number
EP0673409A1
EP0673409A1 EP94901921A EP94901921A EP0673409A1 EP 0673409 A1 EP0673409 A1 EP 0673409A1 EP 94901921 A EP94901921 A EP 94901921A EP 94901921 A EP94901921 A EP 94901921A EP 0673409 A1 EP0673409 A1 EP 0673409A1
Authority
EP
European Patent Office
Prior art keywords
fatty alcohol
surfactant mixtures
general formula
mixtures according
weight
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.)
Withdrawn
Application number
EP94901921A
Other languages
German (de)
English (en)
Inventor
Bert Gruber
Dieter Nickel
Hans-Christian Raths
Eric Sung
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 EP0673409A1 publication Critical patent/EP0673409A1/fr
Withdrawn legal-status Critical Current

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
    • C11D1/66—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
    • C11D1/02—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
    • 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

Definitions

  • the invention relates to water-soluble surfactant mixtures containing mixtures of salts of mono- and / or polyunsaturated fatty alcohol sulfates and saturated fatty alcohol sulfates in addition to nonionic surfactants.
  • the invention further relates to liquid detergents which contain the surfactant mixtures mentioned.
  • Liquid detergents can sometimes be exposed to water up to or below the freezing point during distribution or storage. If the detergent suspension / emulsion is not sufficiently stable to cold, phase separations can occur which lead to inaccurate dosing of the detergent during use if the solids settle to the bottom of the container.
  • the object of the invention was to develop water-soluble surfactant mixtures which lead to good low-temperature stability and good water solubility in the liquid detergents produced therewith.
  • the invention relates to water-soluble surfactant mixtures for liquid detergents containing
  • anionic surfactants selected from mixtures of salts of mono- and / or polyunsaturated fatty alcohol sulfates of the general formula (I),
  • R 1 is an aliphatic, straight-chain or branched, mono- and / or polyunsaturated alkenyl radical with 8 to 22 carbon atoms,
  • Y represents a salt-forming cation of an alkali metal, alkaline earth metal, ammonium or organic bases selected from mono-, di- or triethanolamine, and saturated fatty alcohol sulfates of the general formula (II),
  • R 2 represents an aliphatic, straight-chain or branched, saturated alkyl radical having 8 to 22 carbon atoms and
  • nonionic surfactants selected from fatty alcohol polyglycol ethers of the general formula (III),
  • R3 is an aliphatic linear or methyl branched in the 2-position alkyl radical with 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds
  • R 4 represents hydrogen or a methyl group
  • m represents numbers from 1 to 20.
  • Mixtures of salts of saturated and unsaturated fatty alcohol sulfates which can be obtained by sulfating saturated and unsaturated fatty alcohols and subsequent neutralization with aqueous bases, are anionic surfactants with excellent detergent properties.
  • the invention is based on the knowledge of using synergistic effects to lower the temperature of the phase transition from isotropic-liquid to anisotropic-solid / liquid compared to comparable surfactant mixtures of the prior art described at the beginning on the basis of saturated fatty alcohol sulfates in commercially available liquid detergents, thereby improved cold stability can be guaranteed. This is necessary because the liquid detergents are occasionally exposed to very low temperatures, for example around freezing, before use. It is possible and preferred within the meaning of the present invention to provide surfactant mixtures or liquid detergents with very low phase transition temperatures.
  • the phase transition temperatures are preferably less than or equal to 3 ° C., in particular 2 ° C.
  • the invention comprises surfactant mixtures which are characterized in that the molar ratio of the unsaturated fatty alcohol sulfates of the general formula (I) to the saturated fatty alcohol sulfates of the general formula (II) is in the range from 10 to 1 to 1 to 10, in particular is set in the range from 1 to 10 to 4 to 10.
  • Preferred unsaturated fatty alcohol sulfates of the general formula (I) have fatty alcohol residues which are derived from natural and / or synthetic fatty acids which are used as the starting basis for the preparation of the Serve fatty alcohols. Accordingly, the unsaturated fatty alcohol sulfates of the general formula (I) include, in particular, fatty alcohol residues with 18 to 22 carbon atoms; oleyl sulfate is particularly preferred.
  • R 2 in the general formula (II) represents a saturated alkyl radical having 12 to 16 carbon atoms.
  • the use of relatively short-chain saturated alkyl radicals is particularly preferred here, while the unsaturated alkyl radicals of the unsaturated fatty alcohol sulfates tend to have longer chain lengths.
  • the saturated fatty alcohol sulfates contain less than 22% by weight of alkyl radicals with 18 or more carbon atoms.
  • Surfactant mixtures in which the saturated fatty alcohol sulfates have up to 12% by weight of alkyl radicals having 16 or more carbon atoms are very particularly preferred.
  • the salts of the fatty alcohol sulfates of the general formulas (I) and (II) are obtained by reacting the corresponding fatty alcohols R ⁇ OH and R 2 0H alone or their mixtures, which advantageously have an iodine number in the range from 5 to 180, preferably 10 to 50 and in particular 10 to 20, have been prepared with a sulfating agent and subsequent neutralization with aqueous bases.
  • a sulfating agent in addition to pure saturated fatty alcohols and pure unsaturated fatty alcohols, technical mixtures of saturated fatty alcohols can also be used which also contain proportions of unsaturated fatty alcohols.
  • Suitable sulfating agents are sulfuric acid, oleum, chlorosulfonic acid or gaseous sulfur trioxide in a mixture with an intergas.
  • Particularly suitable neutralization bases are aqueous solutions or suspensions of alkali metal and alkaline earth metal hydroxides or ammonia.
  • a preferred embodiment of the invention consists in that the fatty acid sulfate mixtures of the general formulas (I) and (II) in a total amount of 2 to 15 wt .-%, in particular from 3 to 10 wt .-%, contain.
  • Fatty alcohol polyglycol ethers with a possibly narrowed homolog distribution are to be understood as nonionic surfactants which follow the formula (III)
  • R3 represents an aliphatic hydrocarbon radical with 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds
  • R 4 represents hydrogen or a methyl group
  • m represents numbers from 1 to 20.
  • fatty alcohols R ⁇ OH are used, which are reacted with ethylene and / or propylene oxide in the presence of alkoxylation catalysts.
  • alkoxylation catalysts there is no selective addition of a discrete number of alkylene oxide units to one molecule of the alcohol; the reaction rather follows statistical laws and leads to a mixture of homologous addition products whose degrees of alkoxylation encompass a broad spectrum.
  • the index number in formula (III) indicates the average degree of alkoxylation and can therefore assume integer or fractional values - even less than 1.
  • R ⁇ OH Typical examples of R ⁇ OH are capro alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, behenyl alcohol or erucyl alcohol.
  • Fatty alcohol polyglycol ethers with particularly favorable detergent properties are obtained on the basis of saturated C12 to Cig fatty alcohols, which are preferred for these reasons. From J.Am.Oil.Chem.Soc.
  • Typical examples of fatty alcohol polyglycol ethers are addition products of an average of 1 to 20 moles of ethylene and / or propylene oxide with lauryl alcohol, myristyl alcohol, cetyl alcohol and stearyl alcohol or their mixtures.
  • Fatty alcohol polyglycol ethers with a narrow homolog distribution and particularly favorable surfactant properties are obtained if addition products with an average of 3 to 7 mol ethylene oxide onto fatty alcohols with 12 to 18 carbon atoms are used, which are preferred for these reasons.
  • the aforementioned fatty alcohol polyglycol ethers are preferably contained in the surfactant mixtures according to the invention in an amount of 5 to 50% by weight, in particular 8 to 30% by weight, for example up to 20% by weight.
  • the surfactant mixtures further contain alkyl oligoglycosides.
  • Alkyl oligoglycosides are understood to mean nonionic surfactants which follow the formula (IV)
  • alkyl oligoglycosides for example according to DE-A-37 23 826, fatty alcohols R 3 0H and conventional aldoses or ketoses are used.
  • the reducing saccharides are preferably used because of the higher reactivity.
  • glucose in particular comes into consideration.
  • the alkyl oligoglycosides claimed as part of the surfactant mixtures according to the invention are thus preferably alkyl oligoglucosides.
  • Alkyl oligoglucosides with particularly favorable detergent properties are obtained on the basis of lauryl alcohol and myristyl alcohol, which are preferred for this reason.
  • the index number p in the general formula IV indicates the degree of oligomerization, i.e. H. the distribution of mono- and oligoglycosides. While p must always be an integer in a given compound and can in particular take on the values 1 to 6 here, the value for a specific alkyl oligoglycoside process product is an analytically determined mean value, which usually represents a fractional number.
  • the average degree of oligomerization p preferably has a value of 1.1 to 3.0 and in particular less than 1.5. A degree of oligomerization of 1.1 to 1.4 is particularly preferred.
  • the alkyl oligoglycosides, if present, are used in amounts of 1 to 10% by weight, in particular up to 5% by weight.
  • the surfactant mixtures contain 30 to 60% by weight of anionic and nonionic surfactants, the content of nonionic surfactants being 10 to 35% by weight, based on the made-up liquid detergent. Mixtures of surfactants with particularly high solubility in water have a proportion of up to 25% by weight of nonionic surfactants.
  • the known sulfonates and soaps are suitable as further anionic surfactants within the above-mentioned quantitative ranges.
  • Anionic surfactants used are, for example, those of the sulfonate type.
  • Preferred surfactants of the sulfonate type are Cg-Ci3-alkylbenzenesulfonates, olefin sulfonates, ie mixtures of alkene and hydroxyalkanesulfonates and disulfonates. how to make them out, for example trioxide by sulfonation with gaseous sulfuric or internal double bond and subsequent alkaline or acidic hydrolysis of the sulfonation products obtained in consideration - with s.
  • alkanesulfonates which are obtained from Ci2-Ci8 ⁇ Al anen, for example by sulfochlorination or sulfoxidation with subsequent hydrolysis or neutralization.
  • the sulfonate group is statistically distributed over the entire carbon chain, with the secondary alkanesulfonates predominating.
  • esters of ⁇ -sulfo fatty acids which are prepared by ⁇ -sulfonation of the methyl esters of fatty acids of plant and / or animal origin with 8 to 20 C atoms in the fatty acid molecule and subsequent neutralization to form water-soluble mono-salts.
  • esters of ⁇ -sulfo fatty acids which are prepared by ⁇ -sulfonation of the methyl esters of fatty acids of plant and / or animal origin with 8 to 20 C atoms in the fatty acid molecule and subsequent neutralization to form water-soluble mono-salts.
  • ⁇ -sulfofatty acid alkyl esters are preferred which have an alkyl chain with no more than 4 carbon atoms in the ester group, for example methyl esters, ethyl esters, propyl esters and butyl esters.
  • the methyl esters of ⁇ -sulfofatty acids (MES) are used with particular advantage.
  • Further suitable anionic surfactants are the ⁇ -sulfofatty acids obtainable by ester splitting of the ⁇ -sulfofatty acid alkyl esters or their di-salts.
  • the mono-salts of the ⁇ -sulfofatty acid alkyl esters are obtained in their industrial production as an aqueous mixture with limited amounts of di-salts.
  • sulfosuccinic acid which are also referred to as sulfosuccinates or as sulfosuccinic acid esters and which are monoesters and / or diesters of sulfosuccinic acid with alcohols, preferably fatty alcohols and in particular ethoxylated fatty alcohols.
  • Preferred sulfosuccinates contain CQ to Ciss fatty alcohol residues or mixtures thereof.
  • Particularly preferred sulfosuccinates contain a fatty alcohol residue which is derived from ethoxylated fatty alcohols, which are nonionic surfactants in themselves.
  • sulfosuccinates their fatty alcohol residues are derived from ethoxylated fatty alcohols with a narrow homolog distribution, particularly preferred.
  • Suitable anionic surfactants are, in particular, soaps, preferably in amounts of 10 to 20% by weight, based on the made-up liquid detergent.
  • Saturated fatty acid soaps are suitable, such as the salts of lauric acid, myristic acid, palmitic acid or stearic acid, and in particular from natural fatty acids, e.g. Coconut, palm kernel or tallow fatty acids, derived soap mixtures. In particular, such mixtures are preferred which are composed of 50 to 100% by weight of saturated C 1 -C 6 fatty acid soaps and 0 to 50% by weight of oleic acid soap.
  • the anionic surfactants can be present in the form of their sodium, potassium or ammonium salts and as soluble salts of organic bases, such as mono-, di- or triethanolamine.
  • the anionic surfactants are preferably in the form of their sodium or potassium salts, in particular in the form of the sodium salts.
  • the weight ratio of anionic surfactants to nonionic surfactants is set in the range from 5: 1 to 1: 5 and in particular from 3: 1 to 1: 3.
  • Those embodiments of the invention are particularly advantageous in which the weight ratio of the sum of saturated and unsaturated fatty alcohol sulfates to the sum of the nonionic surfactants is 1: 1 to 1:10 and preferably 1: 2 to 1: 5.
  • the surfactant mixtures according to the invention are prepared by mechanical mixing at an optionally elevated temperature of 30 to 40 ° C .; there is no chemical reaction between the components.
  • the invention further relates to liquid detergents containing the surfactant mixtures as defined above.
  • the liquid detergents can contain one or more of the customary water-soluble detergent constituents.
  • the pH of the agents according to the invention is 7 to 10.5, preferably 7 to 9.5. Higher pH values, for example above 9, can be set by using small amounts of sodium hydroxide solution or of alkali salts, such as sodium carbonate or sodium silicate.
  • the liquid detergents are preferably clear, flowable and pourable under the sole action of gravity and without the action of other shear forces.
  • the preferably builder-free agents optionally contain, as organic solvents, advantageously mono- and / or polyfunctional alcohols, for example ethanol, glycerol and 1,2-propanediol and water.
  • organic solvents advantageously mono- and / or polyfunctional alcohols, for example ethanol, glycerol and 1,2-propanediol and water.
  • the proportion of organic solvents is usually 8 to 20% by weight, preferably 10 to 17% by weight.
  • the proportion of water is chosen so that non-gelling solutions are formed which are stable against demixing, for which 45 to 55% by weight of water are generally sufficient.
  • triethanolamine to the detergent in amounts of up to 8% by weight.
  • the agents can contain known additives commonly used in washing and cleaning agents, preferably foam inhibitors, graying inhibitors, fabric softening agents, salts of polycarboxylic acids, in particular citric acid, salts of polyphosphonic acids, optical brighteners, enzymes, enzyme stabilizers Contain neutral salts such as sulfates and chlorides in the form of their sodium or potassium salts as well as colorants and fragrances or opacifiers.
  • foam inhibitors preferably foam inhibitors, graying inhibitors, fabric softening agents, salts of polycarboxylic acids, in particular citric acid, salts of polyphosphonic acids, optical brighteners, enzymes, enzyme stabilizers Contain neutral salts such as sulfates and chlorides in the form of their sodium or potassium salts as well as colorants and fragrances or opacifiers.
  • Suitable ingredients of the agents are water-soluble inorganic salts such as bicarbonates, carbonates, silicates or mixtures of these;
  • alkali carbonate and alkali silicate especially sodium silicate with a molar ratio a2 ⁇ : Si ⁇ 2 of 1: 1 to 1: 4.5, preferably from 1: 2 to 1: 3.5, are used.
  • salts of polyphosphonic acids for example to stabilize
  • Enzymes the neutral reacting sodium salts of, for example, l-hydroxyethane-l, l-diphosphonate and diethylenetriaminepentamethylenephosphonate are preferably used in amounts of 0.1 to 1.5% by weight.
  • Suitable enzymes are those from the class of proteases, lipases, amylases, cellulases or mixtures thereof. Enzymes obtained from bacterial strains or fungi such as Bacillus subtilis, Bacillus licheniform and Strepto yces griseus are particularly suitable. Proteases of the subtilisin type and in particular proteases which are obtained from Bacillus lentus are preferably used. Their proportion can be about 0.2 to about 2% by weight.
  • the agents can contain further enzyme stabilizers.
  • 0.5 to 1% by weight sodium formate can be used.
  • proteases which are stabilized with soluble calcium salts and a calcium content of preferably about 1.2% by weight, based on the enzyme.
  • boron compounds for example boric acid, boron oxide, borax and other alkali metal borates such as the salts of orthoboric acid (H3BO3), metaboric acid (HBO2) and pyroboric acid (tetraboric acid H2B4O7), is particularly advantageous.
  • Suitable foam inhibitors are, for example, soaps of natural or synthetic origin which have a high proportion of Ci8-C24 ⁇ f : fatty acids.
  • Suitable non-surfactant-like foam inhibitors are, for example, organopolysiloxanes and their mixtures with microfine, optionally silanized silica, and paraffins, waxes, microcrystalline waxes and their mixtures with silanized silica. Mixtures of different foam inhibitors are also advantageously used, for example those made of silicones, paraffins or waxes. Examples
  • the formulation examined in the examples contained the following constituents: Oleic acid: 6% by weight,
  • Citric acid (calculated as free acid): 1.0% by weight
  • the water solubility and the cold resistance of liquid detergents can be determined in accordance with DIN 53 9118 by measuring the force point.
  • turbidity measurements were carried out using the method described by Schwarz and Strand [Tens.Surf.Det. , 24, 143 (1987)].
  • Tab. 1 contains phase transition temperatures (Tp) of the respective surfactant mixtures in the above recipe. Table 1
  • Tp Phase transition temperature
  • phase transition temperatures (Tp) in Examples 1 to 6 according to the invention are all below the phase transition temperatures (Tp) in Comparative Examples 1 to 6. Even if a slight increase in the phase transition temperatures (Tp) occurs due to the addition of alkyl glycosides, Examples 2, 3 and 5 and 6 are nevertheless superior to the corresponding comparative examples 3 to 6 with regard to the low temperatures.

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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

Des mélanges d'agents tensio-actifs solubles dans l'eau contiennent (a) des agents tensio-actifs anioniques sélectionnés parmi des mélanges de sels de sulfates d'alcools gras monoinsaturés et/ou polyinsaturés et de sulfates d'alcools gras saturés et (b) des agents tensio-actifs non-ioniques sélectionnés. Ces mélanges d'agents tensio-actifs, ainsi que les lessives liquides qui les contiennent, présentent une stabilité au froid améliorée par rapport aux mélanges d'agents tensio-actifs ou lessives liquides qui contiennent uniquement des sulfates d'alcools gras saturés comme sulfates d'alcools gras tensio-actifs anioniques.
EP94901921A 1992-12-09 1993-12-01 Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides Withdrawn EP0673409A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19924241473 DE4241473A1 (de) 1992-12-09 1992-12-09 Wasserlösliche Tensidgemische für Flüssigwaschmittel
DE4241473 1992-12-09
PCT/EP1993/003356 WO1994013770A1 (fr) 1992-12-09 1993-12-01 Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides

Publications (1)

Publication Number Publication Date
EP0673409A1 true EP0673409A1 (fr) 1995-09-27

Family

ID=6474790

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94901921A Withdrawn EP0673409A1 (fr) 1992-12-09 1993-12-01 Melanges d'agents tensio-actifs solubles dans l'eau pour lessives liquides

Country Status (3)

Country Link
EP (1) EP0673409A1 (fr)
DE (1) DE4241473A1 (fr)
WO (1) WO1994013770A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2967033B1 (fr) * 2013-03-13 2019-10-02 Stepan Company Tensioactifs a base de dérives alcool gras mono-insaturés

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0107946B1 (fr) * 1982-10-28 1987-03-11 THE PROCTER & GAMBLE COMPANY Compositions détergentes liquides
GB8811672D0 (en) * 1988-05-17 1988-06-22 Unilever Plc Detergent composition
DE4105851A1 (de) * 1991-02-25 1992-08-27 Henkel Kgaa Verfahren zur herstellung von alkyl- und/oder alkenylsulfat-pasten mit verbesserter fliessfaehigkeit
DE4123820A1 (de) * 1991-07-18 1993-01-21 Henkel Kgaa Fliess- und pumpfaehige tensidmischungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9413770A1 *

Also Published As

Publication number Publication date
WO1994013770A1 (fr) 1994-06-23
DE4241473A1 (de) 1994-06-16

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