EP0712436B1 - Produits de lavage ou de nettoyage faiblement moussants - Google Patents

Produits de lavage ou de nettoyage faiblement moussants Download PDF

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Publication number
EP0712436B1
EP0712436B1 EP94925395A EP94925395A EP0712436B1 EP 0712436 B1 EP0712436 B1 EP 0712436B1 EP 94925395 A EP94925395 A EP 94925395A EP 94925395 A EP94925395 A EP 94925395A EP 0712436 B1 EP0712436 B1 EP 0712436B1
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EP
European Patent Office
Prior art keywords
alkyl
weight
fatty acid
detergent
cleaning formulation
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.)
Expired - Lifetime
Application number
EP94925395A
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German (de)
English (en)
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EP0712436A1 (fr
Inventor
Udo Hees
Eva Kiewert
Ansgar Behler
Astrid Haferkamp
Kerstin Link
Amerigo Pastura
Nada Volf
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication date
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Publication of EP0712436A1 publication Critical patent/EP0712436A1/fr
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Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—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
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • the invention relates to low-foaming detergents or cleaning agents, with liquid detergents and cleaning agents for hard surfaces being preferred. All non-textile surfaces occurring in the household and commercial sector, with the exception of dishes, are to be understood as cleaning agents for hard surfaces.
  • the term general-purpose cleaner has become established for this type of cleaning agent. Low-foaming all-purpose cleaners are those that develop a low volume of foam when used manually, which significantly reduces within a few minutes.
  • All-purpose cleaners have been known for a long time. These are essentially aqueous surfactant solutions of various types with or without the addition of builders and with or without the addition of water-soluble solvents or solubilizers.
  • a disadvantage of manual application in practice has been its high foaming power. Although the consumer wants to perceive a certain amount of foam in the application solution at the beginning of his cleaning work to prove its effectiveness, the foam should then collapse as quickly as possible, so that once cleaned surfaces do not have to be wiped down.
  • Liquid detergents also tend to have a high foaming capacity, which affects their applicability in washing machines.
  • alkyl polyglycosides are known to be highly foaming surfactants; They are therefore used for products with the desired high foaming capacity, So recommended for manual dishwashing detergents or for washing hair.
  • EP 0 070 074 B1 and 0 070 076 B2 describe such high-foaming washing and cleaning agents based on various APG-containing surfactant combinations. Consequently, these combinations are not recommended for the area of all-purpose cleaners.
  • German published patent application DE 42 27 046 describes detergent mixtures based on fatty acid alkyl ester alkoxylates.
  • WO-A-91 14 760 discloses low-foaming surfactant mixtures consisting of alkyl polyglycosides and fatty alcohol alkoxylates etherified with alkyl radicals.
  • the object of the present invention was to provide washing or cleaning agents which at the same time have good cleaning properties, good biodegradability and a pronouncedly low foaming power.
  • the criterion should be that initially formed foam visibly reduces within 2 minutes.
  • the invention relates to water-containing washing or cleaning agents containing 0.1 to 50% by weight, preferably 1 to 20% by weight, of at least one alkyl polyglycoside of the formula I, R 1 -O- [Z] x (I), where R 1 is a branched or straight-chain, saturated or unsaturated alkyl group having 8 to 18 carbon atoms, Z is a sugar residue, preferably a glucose or Xylose radical and x represents integers from 1 to 10, and 0.05 to 50% by weight, preferably 1 to 20% by weight, of at least one fatty acid alkyl ester alkoxylate of the formula II, R 2 -CO 2 - (AO) y -R 3 (II), where R 2 is a branched or straight-chain, saturated or unsaturated alkyl group having 5 to 21 C atoms, AO is a C 2 -C 4 alkylene oxide unit, y is a number from 1 to 30 and R 3 represents a straight-chain or branched alkyl group
  • the alkyl polyglycosides used in the agents according to the invention are known substances which can be obtained by the relevant methods of preparative organic chemistry; as a representative, reference is made to the documents EP 0 301 298 A1 and WO 90/3977.
  • the alkyl polyglycosides can be from sugars or sugar residues, i.e. Derive aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose and xylose.
  • the preferred alkyl polyglycosides are thus alkyl polyglucosides and alkyl polyxylosides.
  • the alkyl radical R 1 in the formula (I) can be derived from primary branched and unbranched alcohols having 8 to 18 carbon atoms. Typical examples are myristyl alcohol, cetyl alcohol and their technical mixtures. However, preference is given to using alkylpolyglycosides of the formula (I) in which R 1 represents a carbon radical having 8 to 12, in particular 8 to 10, carbon atoms. In addition to lauryl alcohol, typical examples are, in particular, caprylic alcohol and capric alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the fatty acid alkyl ester alkoxylates of the formula (II) used in the agents according to the invention can be prepared by conventional methods, such as, for example, by esterification of fatty acid derivatives with alkoxylated methanol.
  • this process has some disadvantages, it has two stages, the esterification takes a very long time and the products are colored by the high reaction temperatures.
  • fatty acid methyl ester alkoxylates produced in this way often have relatively high OH numbers after the esterification, which can be problematic for some applications.
  • the fatty acid alkyl ester alkoxylates of the formula (II) are preferably prepared by heterogeneously catalyzed direct alkoxylation of fatty acid alkyl esters with alkylene oxide, in particular ethylene oxide. This synthesis method is described in detail in WO 90/13533 and WO 91/15441. The resulting products are characterized by a low OH number, the reaction is carried out in one step and light-colored products are obtained. Those fatty acid alkyl ester alkoxylates of the formula (II) which are formed by ethoxylation of fatty acid methyl esters, ie in which A0 in the formula (II) is an ethylene oxide unit and R 3 is a methyl group, are preferably used.
  • the fatty acid methyl esters used as starting materials can be obtained from natural oils and fats as well as produced synthetically.
  • Fatty acid alkyl ester alkoxylates are preferably used in the all-purpose cleaners according to the invention, where y is a number from 5 to 25, in particular from 9 to 18.
  • fatty acid alkyl ester alkoxylates are preferably used in the liquid detergents according to the invention, where R 2 is a branched or straight-chain, saturated alkyl group having 12 to 18 carbon atoms and y is a number from 3 to 15.
  • liquid detergents and general-purpose cleaners according to the invention are to be used to remove lipophilic soiling, fatty acid alkyl ester alkoxylates with a low degree of ethoxylation in the range according to the invention are selected; if hydrophilic soiling is to be removed, the use of fatty acid alkyl ester ethoxylates with a higher degree of ethoxylation in the range according to the invention is expedient.
  • the above-mentioned liquid detergents and all-purpose cleaners additionally contain an anionic surfactant selected from the group of the C 6 -C 18 alkylbenzenesulfonates, C 6 -C 18 alkanesulfonates, C 6 -C 18 alkyl sulfates, C 6 -C 18 - Alkyl polyglycol ether sulfates, ⁇ -olefin sulfonates, C 6 -C 18 alkyl polyglycol ether sulfonates, glycerol ether sulfonates, glycerin ether sulfates, hydroxymixed ether sulfates, monoglyceride sulfates, sulfosuccinates, sulfotriglycerides, soaps, amide soaps, C 6 -C 6 fatty acid alkamides, C 6 -C 18 carboxylate alkoxide s
  • an anionic surfactant
  • liquid detergent or all-purpose cleaners additionally contain a further nonionic surfactant selected from the group of C 6 -C 18 -alkyl polyglycol ether, Zuckerester, C 6 -C 18 -Fettklarepolyglykolether, sorbitan fatty acid esters, C 6 -C 18 fatty acid partial glycerides as well as their Mixtures in a total amount of up to 30 wt .-%, based on the total amount of liquid detergent or all-purpose cleaner.
  • a further nonionic surfactant selected from the group of C 6 -C 18 -alkyl polyglycol ether, Zuckerester, C 6 -C 18 -Fettkladilicates, sorbitan fatty acid esters, C 6 -C 18 fatty acid partial glycerides as well as their Mixtures in a total amount of up to 30 wt .-%, based on the total amount of liquid detergent or all-purpose cleaner.
  • Particularly preferred embodiments contain anionic surfactants selected from the group of the C 6 -C 18 alkyl sulfates, the C 6 -C 18 alkyl polyglycol ether sulfates, the soaps and the C 6 -C 18 alkane sulfonates and their mixtures or nonionic surfactants selected from the group of the C 6 -C 18 alkyl polyglycol ether.
  • the soaps to be used according to the invention are alkali, ammonium or alkanolammonium salts of saturated or unsaturated fatty acids with 8-22, preferably 10-18, carbon atoms.
  • the soaps can either be added as such or, after the addition of appropriate fatty acids, can be formed by salt formation with bases such as NaOH, KOH, NH 3 , amines or alkanolamines.
  • bases such as NaOH, KOH, NH 3 , amines or alkanolamines.
  • the soaps are either completely neutralized or partly also in free form as fatty acids.
  • the C 6 -C 18 alkyl ether sulfates are primarily addition products of 2-15 moles of ethylene oxide with C 6 -C 18 fatty alcohols, which are then sulfated.
  • the C 6 -C 18 alkyl polyglycol ethers used as nonionic surfactants are primarily adducts of 2-10 mol ethylene oxide with C 6 -C 18 fatty alcohols.
  • Auxiliaries customary in liquid detergents or all-purpose cleaners can optionally be added; these substances are builders, e.g. Glutaric acid, succinic acid, adipic acid, tartaric acid, benzene hexacarboxylic acid, gluconic acid, trisodium citrate; Solvents, e.g. Acetone, ethanol or glycerin, hydrotropes e.g. Cumene sulfonate, octyl sulfate, butyl glucoside, butylene glycol; Cleaning booster; Viscosity regulators, e.g. synthetic polymers such as polyacrylates; pH regulators, e.g. Citric acid, triethanolamine or NaOH; Preservatives, e.g. Glutaraldehyde; Dyes, fragrances and opacifiers.
  • builders e.g. Glutaric acid, succinic acid, adipic acid, tartaric acid, benzene
  • the pH of the all-purpose cleaners according to the invention is usually between 4 and 8.5, preferably between 6 and 8. However, a range between 7.0 and 7.5 is particularly preferred.
  • the pH value at an application concentration of 10 g / l is preferably 7.3-7.8.
  • the agents according to the invention are particularly suitable for cleaning hard surfaces such as e.g. Enamel, glass, PVC, linoleum, stone floors, e.g. Marble, terrazzo, unglazed clinker, ceramic tiles or sealed wooden floors, e.g. Parquet or floorboards.
  • hard surfaces such as e.g. Enamel, glass, PVC, linoleum, stone floors, e.g. Marble, terrazzo, unglazed clinker, ceramic tiles or sealed wooden floors, e.g. Parquet or floorboards.
  • the pH of the liquid detergents according to the invention is usually between 6.0 and 10.0, preferably between 7.0 and 9.0.
  • the liquid detergents are suitable both for use in washing machines and for use in hand basins for washing high-quality textiles made of wool or silk.
  • the test method described below according to "Seifen- ⁇ le-Fette-Wwachs", 112 , 371, (1986) was used to test the cleaning ability and provides very reproducible results.
  • the cleaning agent to be tested was then placed in the form of a 1% by weight aqueous solution (10 g / l) on an artificially soiled plastic surface.
  • a mixture of carbon black, machine oil, triglyceride, saturated fatty acids and low-boiling aliphatic hydrocarbon was used as artificial soiling for the dilute use of the cleaning agent.
  • the test area of 26 x 28 cm was evenly coated with 2 g of the artificial soiling with the aid of a surface coater.
  • a plastic sponge was impregnated with 10 ml of the 1% detergent solution to be tested and moved mechanically on the dirt-coated test surface, to which 10 ml of the 1% detergent solution to be tested was also applied. After 10 wiping movements, the cleaned test area was kept under running water and the loose dirt was removed.
  • the cleaning effect of the plastic surface cleaned in this way was determined with the aid of a "Microcolor" remission color measuring device (Dr. B. Lange).
  • the measurand is the degree of whiteness.
  • the clean white plastic surface served as the white standard; the whiteness of the clean, white plastic surface corresponds to 100% RV (cleaning ability).
  • the whiteness of a soiled and then cleaned plastic surface corresponds to a value between 0% and 100% RV.
  • The% RV values represent mean values from triplicate determinations.
  • the foaming behavior of the all-purpose cleaners according to the invention was tested as follows: The test product was placed in a large-volume serving glass. Then the amount of tap water was allowed to flow in freely from a height of 30 cm, which, together with the amount of product presented, gave an application concentration of the product of 10 g / l. The foam height in the beaker was read off immediately after the addition of water had ended.
  • compositions were prepared by mixing the components together and then adjusting the desired pH. All percentages relate to percent by weight of active substance.
  • Compositions 1 to 9 are shown in Table 1.
  • Composition 1 (V) is not according to the invention and is used for comparison.
  • the fatty acid alkyl ester alkoxylates are given in Table 1 in the following notation:
  • Example: C 12 FSEO 15 Me stands for C 11 H 23 CO 2 (CH 2 CH 2 O) 15 CH 3 , methyl ester of C 12 fatty acid ethoxylated with 15 ethylene oxide units.
  • EO stands for ethylene oxide
  • PO stands for propylene oxide.
  • the degrees of alkoxylation represent mean values.
  • compositions 2 to 9 according to the invention are clearly superior to comparative composition 1 (V) in terms of cleaning ability and foam disintegration.
  • Example 10 represents an all-purpose cleaner high concentrate, which is used in 0.1% solution.
  • the agent had excellent foam properties (low foam values).
  • an agent V was tested which had a C 13 -C 15 alcohol x 5 E0 instead of the fatty acid methyl ester.

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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 a pour objet des produits liquides de lavage et des produits de nettoyage pour tous usages faiblement moussants qui contiennent des C8-C18-alkylpolyglucosides et des alkylesteralcoxylates d'acides gras, en particulier des méthylesteréthoxylates d'acides gras.

Claims (8)

  1. Produit de lavage et de nettoyage aqueux contenant : de 0,1 à 50 % en poids, de préférence de 1 à 20 % en poids d'au moins un alcoylpolyglycoside de formule I,

            R1-O-[Z]x     (I)

    dans laquelle R1 représente un radical alcoyle ramifié ou linéaire, saturé ou non saturé, ayant de 8 à 18 atomes de carbone,
    Z représente un radical de sucre, de préférence un radical de glucose ou de xylose, et
    x représente des nombres entiers allant de 1 à 10, et
    de 0,05 à 50 % en poids, de préférence de 1 à 20 % en poids, d'au moins un alcoxylate d'ester d'alcoyle d'acide gras de formule II,

            R2-CO2-(AO)y-R3     (II)

    dans laquelle R2 représente un radical alcoyle ramifié ou linéaire, saturé ou non saturé, ayant de 5 à 21 atomes de carbone,
    AO représente une unité d'oxyde d'alcoylène en C2-C4,
    y représente un nombre allant de 1 à 30 et,
    R3 représente un radical alcoyle linéaire ou ramifié ayant de 1 à 6 atomes de carbone.
  2. Produit selon la revendication 1,
    caractérisé en ce que
    dans alcoylpolyglycoside de formule I R1 représente un radical alcoyle ayant de 8 à 12 atomes de carbone et,
    dans l'alcoxylate d'ester d'alcoyle d'acide gras de formule II, AO représente une unité d'oxyde d'éthylène et R3 un radial méthyle.
  3. Produit selon la revendication 1 et la revendication 2,
    caractérisé en ce qu'
    un agent tensioactif anionique choisi dans le groupe des (alcoyle en C6-C18) benzènesulfonates, des (alcane en C6-C18) sulfonates, des (alcoyle en C6-C18) sulfates, des (alcoyle en C6-C18) polyglycoléthersulfates, des α-oléfinesulfonates, des (alcoyle en C6-C18) polyglycoléthersulfonates, des glycéroléther sulfonates, des glycéroléthersulfates, des éther sulfates mixtes hydroxylés, des monoglycéride sulfates, des sulfosuccinates, des sulfotriglycérides, des savons, des savons amides, des éthersulfates d'amides d'acide gras en C6-C18, des (alcoyle en C6-C18) carboxylates, des isethionates d'acide gras, des saccosinates N-acylés en C6-C18, des taurides N-acylés en C6-C18, des (alcoyle en C6-C18) oligoglucoside sulfates, des (alcoyle en C6-C18) phosphates ainsi que de leurs mélanges en une quantité totale allant jusqu'à 40 % en poids rapporté au produit global, y est contenu.
  4. Produit selon la revendication 1 à 3,
    caractérisé en ce qu'
    un autre agent tensioactif non ionique choisi dans le groupe des (alcoyle en C6-C18) polyglycoléthers, des esters de sucre, des éthers d'acide gras en C6-C18 polyglycol, des esters d'acide gras de sorbitanne, des glycérides partiels d'acide gras en C6-C18, ainsi que leurs mélanges en une quantité totale allant jusqu'à 30 % en poids, rapporté au produit global, y est contenu.
  5. Produit selon la revendication 3,
    caractérisé en ce que
    l'agent tensioactif anionique est choisi dans le groupe des (alcoyle en C6-C18) sulfates, des (alcoyle en C6-C18) polyglycoléthersulfates, des savons et des (alcane en C6-C18) sulfonates ainsi que de leurs mélanges.
  6. Produit selon la revendication 4,
    caractérisé en ce que
    l'agent tensioactif non ionique est choisi dans le groupe des (alcoyle en C6-C18) polyglycoléthers.
  7. Utilisation d'un produit selon l'une des revendications 1 à 6 comme produit de nettoyage pour tous usages en vue du nettoyage de surfaces dures, dans lequel on utilise de préférence un alcoxylate d'ester d'alcoyle d'acide gras dans lequel y représente un nombre allant de 5 à 25 et en particulier de 9 à 18.
  8. Utilisation d'un produit selon l'une des revendications 1 à 6 comme produit de lavage liquide, dans lequel on utilise de préférence un alcoxylate d'ester d'alcoyle d'acide gras, dans lequel R2 représente un radical alcoyle, ramifié ou linéaire, saturé, ayant de 12 à 18 atomes de carbone et y représente un nombre allant de 3 à 15.
EP94925395A 1993-08-04 1994-07-26 Produits de lavage ou de nettoyage faiblement moussants Expired - Lifetime EP0712436B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4326112A DE4326112A1 (de) 1993-08-04 1993-08-04 Reinigungsmittel für harte Oberflächen
DE4326112 1993-08-04
PCT/EP1994/002466 WO1995004803A1 (fr) 1993-08-04 1994-07-26 Produits de lavage ou de nettoyage faiblement moussants

Publications (2)

Publication Number Publication Date
EP0712436A1 EP0712436A1 (fr) 1996-05-22
EP0712436B1 true EP0712436B1 (fr) 1997-03-19

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EP94925395A Expired - Lifetime EP0712436B1 (fr) 1993-08-04 1994-07-26 Produits de lavage ou de nettoyage faiblement moussants

Country Status (6)

Country Link
US (1) US5753606A (fr)
EP (1) EP0712436B1 (fr)
JP (1) JPH09501195A (fr)
DE (2) DE4326112A1 (fr)
ES (1) ES2099628T3 (fr)
WO (1) WO1995004803A1 (fr)

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JPH09501195A (ja) 1997-02-04
DE4326112A1 (de) 1995-02-09
EP0712436A1 (fr) 1996-05-22
WO1995004803A1 (fr) 1995-02-16
ES2099628T3 (es) 1997-05-16
US5753606A (en) 1998-05-19
DE59402172D1 (de) 1997-04-24

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