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EP0533728A1 - Utilisation de composés d'hydroxyde à deux couches pour la coagulation - Google Patents

Utilisation de composés d'hydroxyde à deux couches pour la coagulation

Info

Publication number
EP0533728A1
EP0533728A1 EP19910910614 EP91910614A EP0533728A1 EP 0533728 A1 EP0533728 A1 EP 0533728A1 EP 19910910614 EP19910910614 EP 19910910614 EP 91910614 A EP91910614 A EP 91910614A EP 0533728 A1 EP0533728 A1 EP 0533728A1
Authority
EP
European Patent Office
Prior art keywords
formula
waxes
coagulation
coagulant
coagulant according
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Withdrawn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
EP19910910614
Other languages
German (de)
English (en)
Inventor
Wolfang Breuer
Helmut Endres
Thomas Molz
Hans-Toni Vogt
Ragnar Margeit
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 EP0533728A1 publication Critical patent/EP0533728A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
    • C02F1/5236—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using inorganic agents
    • C02F1/5245—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using inorganic agents using basic salts, e.g. of aluminium and iron
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium, with or without oxygen or hydrogen, and containing two or more other elements
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F7/00—Compounds of aluminium
    • C01F7/78—Compounds containing aluminium, with or without oxygen or hydrogen, and containing two or more other elements
    • C01F7/784—Layered double hydroxide, e.g. comprising nitrate, sulfate or carbonate ions as intercalating anions
    • C01F7/785—Hydrotalcite
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
    • C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/71—Paint detackifiers or coagulants, e.g. for the treatment of oversprays in paint spraying installations
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/20—Two-dimensional structures
    • C01P2002/22—Two-dimensional structures layered hydroxide-type, e.g. of the hydrotalcite-type

Definitions

  • the invention relates to coagulants for lacquers, waxes and / or coating compositions containing double-layer hydroxide compounds, aqueous slurries containing the coagulants, a process for the preparation of the coagulants and the use of the coagulants and / or the aqueous slurry.
  • the agents known hitherto had a number of disadvantages when used for the coagulation of conventional lacquers: they took a relatively long time to coagulate the lacquer particles and to satisfactorily dispose of the water used to remove excess lacquer mist. In unfavorable cases, defective detackification led to the deposition of paint particles that were sticking together in the entire system area. Many of the coagulants known up to that time contained substances (for example inorganic anions such as chloride or sulfate) which accumulated in the circulating water and had a corrosive effect on the parts of the plant. The frequent bath changes that this forced were increasingly regarded as disadvantageous. Since an extension of the service life of the disposal baths is desirable for water technology reasons, the use of substances which accumulate rapidly in the disposal baths and thus impair the functionality of the system for various reasons is undesirable.
  • substances for example inorganic anions such as chloride or sulfate
  • EP-A 0 193 668 discloses the use of Hectorite ⁇ in connection with defoamers for detackifying and clarifying waste water containing overspray. For example, paint adsorption was able to be carried out on the surface of bentonites, thus ensuring that the paint particles were detached.
  • DE-PS 3421 289 discloses agents for detackifying and coagulating synthetic resin lacquer components in wet separators of spray painting systems which contain 5 to 20% by weight of a wax, 10 to 30% by weight of an alkanolamine, 0.5 to 5% by weight .-% contain a defoamer and water.
  • these agents represent an advance over the prior art described above, they have not been able to disperse paints which are difficult to detack, such as so-called "high-solid paints" with a "high solids content” or polyurethane stone chip protection primer filler paints hold and thus enable continuous coagulum withdrawal. They also contain alkanolamines, the use of which is not desirable due to the known disadvantages associated therewith.
  • the object of the present invention was to provide coagulants for paints and bleaching agents which remedy the disadvantages of the prior art mentioned.
  • the new coagulants should not only enable the paints and coating compositions to be detackified well to form agglomerates, but should also promote good discharge of the agglomerates formed by keeping the solids evenly in the dispersion. This was intended to ensure continuous removal of the coagulates from the circulating water without settling in critical system parts, both in the above-mentioned systems with continuous coagulum removal and in conventional flotation or sedimentation systems.
  • the invention relates to coagulants for lacquers, waxes and / or coating compositions containing double-layer hydroxide compounds of the general formula (I)
  • M 11 for at least one divalent metal cation
  • Vm for at least one trivalent metal cation
  • A for the equivalent of an anion of a mono- or polybasic
  • double vision hydroxides are known in the literature, for example from R. Allmann, Chimia 24 (1977), page 99. Chemically they are mixed basic hydroxy salts of divalent and trivalent metal cations.
  • Natural and synthetic double-layer hydroxides continuously release water when heated or calcined.
  • the water of crystallization is completely removed at 200 ° C., higher temperatures lead to the elimination of water from the hydroxide structure and of carbon dioxide from the carbonate contained as the usual anion.
  • the structures of the double-layer hydroxides are broken down in this process.
  • the coagulants are characterized in that the anion A of the formula (I) is selected from carbonate, sulfate, chloride, Ni ⁇ trate and phosphate ions. Because of the extraordinarily large distribution of carbonate ions, even with naturally occurring double-layer hydroxides, carbonate ions are particularly preferred.
  • the divalent metal cation of the formula (I) is preferably selected from
  • the trivalent metal cation of the formula (I) is preferably selected from iron and aluminum. If - in connection with the explanation of the general formula (I) - there is talk of at least one divalent and trivalent metal cation, this means that in such double-layer hydroxide compounds if necessary, several divalent or trivalent metal cations can be present side by side.
  • a prototype of preferred cationic double layer hydroxide compounds is the mineral hydrotalcite, which has the following ideal formula:
  • Hydrotalcite is structurally derived from brucite [Mg (0H) 2 ]. Brucite crystallizes in a layer structure with the metal ions in octahedral gaps between two layers of densely packed hydroxide ions, but only every second layer of the octahedral gaps is occupied. In hydrotalcite, the layer package receives a positive charge in that some magnesium ions are substituted by aluminum ions. This positive charge is compensated for by anions which are located in the interlayers together with crystal water.
  • the layer structure is clear from X-ray diffraction diagrams, which can also be used for characterization (JCPDS file: 22-700).
  • Synthetically produced hydrotalcites are generally known, among others they are described in DE-OS 15 92 126, DE-PS 33 06 822, DE-OS 3346 943 and EP-A 0 207811.
  • EP-A 0 207811 describes a particularly finely divided product described that arises during a Conti precipitation (flash precipitation) when one looks at the starting solutions (Metal salt solution and alkaline carbonate solution) can flow together continuously, then filtered, washed and the product left in the moist state.
  • the agents according to the invention for the coagulation of lacquers, waxes and / or coating agents may optionally also contain one or more active substances and / or auxiliaries known per se from the prior art for coagulation and / or confectioning, in particular flocculation aids, defoamers Contain corrosion inhibitors, hardness formers, waxes and / or biocides. These must be such that they do not interact with the previously mentioned components in a way that adversely affects the coagulation result. Examples include cyanamides and / or dicyandiamide and / or calcium cyanamide. These compounds are known from DE-OS 3412763.1 for use in coating coagulation. Other components can be calcium and / or aluminum and / or magnesium compounds.
  • flocculants such as Polyethyleni ine and / or Polyacryla ide can be added. Their molecular masses are preferably in the range from about 5 ⁇ 10 4 to 5 ⁇ 10 7 D. Waxes, such as are described, for example, in DE-PS 27 58873 or DE-PS 34 21 289, can be used as further active ingredients which may be added.
  • Special requirements such as B. the setting of a certain pH value or the antimicrobial treatment of the coagulation agents can be taken into account in that the agents contain special additives.
  • boric acid the has antimicrobial effect and may also contribute to pH adjustment, as well as biocides, e.g. B. formaldehyde, isothiazolines and their derivatives and pyridine-N-oxide and its derivatives.
  • Phosphoric acid, organic acids such as citric acid and other non-corrosive acids or their acid salts may also be used to adjust the pH.
  • Corrosion inhibitors and defoamers are also possible as further possible constituents of the coagulants according to the invention.
  • the product Dehydran R F from Henkel KGaA
  • the product Dehydran R F has proven itself as a defoamer.
  • the invention also includes aqueous slurries of the coagulants mentioned.
  • these slurries contain 2 to 30% by weight of coagulants and, if appropriate, of the other active substances and / or auxiliaries mentioned above. The rest of it then consists of water.
  • the formulation of the coagulants according to the invention as aqueous slurries has the advantage that the double-layer hydroxide compounds are already in the dispersed state immediately before use in the coagulation and their detackifying and coagulating effect immediately after addition to the circulating water and / or settling basin can unfold.
  • Another embodiment of the present invention is the "in situ" precipitation of double-sighted hydroxide compounds in the presence of paints, waxes and / or coating agents.
  • a water-soluble salt of the divalent metal cations is reacted with hydroxyl complexes of trivalent metal cations. So that salting-up of the bath liquid is kept as low as possible, the production of hydrotalcite is preferably carried out by reaction of soluble magnesium salts and aluminate lye.
  • the " aluminate solution" can be metered in. After the stoichiometric addition has ended, the mixture is left to stir for some time, after which a medium-disperse precipitate with a a clear and colorless solution.
  • the pH of the aqueous phase is preferably in the range from 8 to 9. If solutions are still cloudy, a further treatment with one of the abovementioned flocculants may be necessary.
  • the coagulants according to the invention or their aqueous slurries (slurries) are used for the coagulation of paints, waxes and / or coating agents in circulating water and sedimentation tanks in paint disposal systems.
  • the aqueous slurries according to the invention preferably contain the coagulants in an amount of 2 to 30% by weight. They are continuously mixed with the circulating water and / or the settling basin of the plants by means of known, suitable metering devices, for which the aqueous slurries described are particularly suitable. It is also possible to add the agents discontinuously, for example once or several times a day.
  • the amounts used are such that the amount of coagulant is in the range from 1 to 100% by weight, preferably 2 to 10% by weight, based on the paint overspray. This can be achieved, for example, with a basic approach of 0.1 to 0.3% based on the total amount of circulating water.
  • the agents for coagulating paints, waxes and coating agents in accordance with the above description show excellent properties when used: for example, the paint particles are not only completely detacked, but also with the circulating water in the form of a readily removable coagulum from the were carried out without disturbing the system parts due to sticking or blockages.
  • the paint particles are kept floating in the dispersion and can thus be easily separated from the circulating water even in continuously operating disposal systems. Even in conventional plants, there are no problems with separating the coagulum. They are just as suitable for use in conventional systems that float or sediment the detackified paint coagulate as in the recently used, continuously operating disposal systems that keep the coagulate in the dispersion and continuously dispose of it.
  • paints that are difficult to dispose of can be detacked without any problems and removed from the systems.
  • the agents can be formulated in liquid form, that is to say as aqueous slurries, and are automatically added to the circulating water and calming basin without a premixing system, that is to say with pumps to be continuously monitored and controlled can. There is no odor nuisance due to strong smelling ingredients.
  • the first method (Examples 1.1 to 6.2) is based on a hydro basecoat.
  • the coagulation experiments were carried out on a 1/2 1 scale. Conditions that were as real as possible were simulated:
  • the coating of overspray from typical spray booths in the automotive industry is about 25 kg / h.
  • a concentration of paint of 6 to 7 g / 1 builds up in the circulating water within one day.
  • a lacquer concentration of 5 g / l was therefore set and used for the subsequent coagulation and precipitation experiments.
  • tests were carried out with a 90 1 pilot plant. Different Ford hoe (red and white topcoat, primer and clearcoat) were used.
  • a polyurethane / polyester lacquer was used as the hydro base lacquer, which corresponds to the type of binder PU7 PE melamine. This has a solids content of approximately 24% by weight and a binder content of approximately 19.5% by weight. This varnish has a solvent content (Water and mono- and dihydric alcohols) of about 76% by weight.
  • Example 1.1 1 g of calcined hydrotalcite (prepared by heating hydrotalcite to 500 ° C. in the course of 2 hours, loss in mass approx. 40% by weight) was used. A medium-sized precipitate with a moderately cloudy, protruding solution was observed.
  • Example 1.1 5 g of flash-precipitated hydrotalcite with 20% solids content 1 were used. A coarse reverse flocculation (slowly sedifying) with a slightly cloudy, protruding solution was observed; aftertreatment with an ultra-stirrer (approx. 15000 revolutions / min) resulted in a fast flotation of the solids content and a clear solution.
  • Example 1.1 5 g of flash-precipitated pyroaurite with 25% solids content was used. The observations correspond to those of Example 1.3, but a slightly cloudy solution was obtained.
  • the hydrobase lacquer suspension according to Example 1.1 500 ml of the hydrobase lacquer suspension according to Example 1.1 with a concentration of 5 g / 1, 1 g of commercially available hydrotalcite and 10 ml of a cationic flocculant were added. Approximately 1 min after the addition of the double layer hydroxide phase, the flocculant was added as a 0.1% solution and stirring was continued for 2 min. The solution above was clear and discolored.
  • a flocculant used was a polyacrylamide-based one which was commercially available as a 0.1% solution, for example under the designation P-3-ferrocryl 8767 from the applicant.
  • Example 2.1 500 mg of calcined hydrotalcite and 10 ml of cationic flocculant were used.
  • reaction was carried out with 2 g of calcined hydrotalcite and 5 ml of the cationic floating aid. In all three cases there were medium to coarse flakes, the protruding solutions were clear and discolored.
  • Example 2.1 In accordance with Example 2.1, 2.5 g of flash-precipitated hydrotalcite (20% solids content) and 25 ml of cationic flocculation aid were used. Alternatively, 5 g of flash-precipitated hydrotalcite and 10 and 25 ml of cationic flocculation aid were used.
  • Example 2.1 5 g of flash-precipitated pyroaurite (25% solids content) and 10 ml of flocculant were used.
  • Example 2.1 5.1 g of Mg (N ⁇ 3) was dissolved in 1 l of a lacquer suspension in water. 6 H 0 and mixed with stirring with an amount equivalent to the hydrotalcite formula of an aluminate which contained 11.1% Al 2 03 and 19.1% Na 0. Subsequently 40 ml of the flocculant were added. The suspension had a pH of 8 to 9.
  • hydrotalcite (X) in g according to the following Table 1 was suspended in 300 ml of water and a certain amount of an undiluted hydro-based lacquer (Y) in g according to Table 1 was added with stirring.
  • Example 3.1 10 ml of the neutral flocculant was added. Here too, coarse-fluffy precipitates and almost clear, protruding solutions were obtained.
  • Example 3.1 5 g of commercially available hydrotalcite and 6 ml of the neutral flocculant were used. A flaky precipitate with a practically clear solution was also observed here.
  • Example 1.1 1.25 g of magaldrate was added to 500 ml of the lacquer suspension with a concentration of 5 g / l while stirring. The mixture was stirred for a further 5 min, after which a finely dispersed precipitate was observed in the suspension with a highly cloudy, protruding solution.
  • Example 4.2 1.25 g of magaldrate was added to 500 ml of the lacquer suspension with a concentration of 5 g / l while stirring. The mixture was stirred for a further 5 min, after which a finely dispersed precipitate was observed in the suspension with a highly cloudy, protruding solution.
  • Example 4.2 1.25 g of magaldrate was added to 500 ml of the lacquer suspension with a concentration of 5 g / l while stirring. The mixture was stirred for a further 5 min, after which a finely dispersed precipitate was observed in the suspension with a highly cloudy, protruding solution.
  • Example 4.1 2.5 g of magaldrate were used. A finely dispersed precipitate with cloudy supernatant solution was observed in the suspension.
  • magaldrate or calcined magaldrate was added under the abovementioned conditions. After stirring for 5 min, 10 ml of the 0.1% cationic flocculant solution were added. When using 1.25 g of magaldrate, medium-dispersed, -dedicated coagulates with a clear, protruding solution were obtained. When using 2.5 g of magaldrate, a slight clouding of the supernatant solution was observed. In the Using calcined magaldrate gave flaky precipitates, but with strongly cloudy solutions.
  • Example 1.1 500 g of the paint suspension with a content of 5 g / 1 was 3.4 g of the flash-precipitated Zn / Al product [ZnöAl (0H) i6] CO3. mH 2 0 (flash-precipitated laboratory product, solids content 36.4%) and stirred vigorously. Vuminous, slowly sedimenting precipitates with medium-cloudy, supernatant solutions were obtained. Aftertreatment with an ultrasonic stirrer (approx. 15000 revolutions / min) resulted in a fast flotation of the solids content with a medium cloudy solution.
  • Example 7 Using 6.7 g of the flash-precipitated Zn-Al product according to Example 6.1, the procedure was as in Example 1.1. A voluminous, slowly sedimenting precipitate with a slightly cloudy, protruding solution was obtained. Aftertreatment with an ultra-stirrer resulted in rapid flotation of the solids content with a medium-cloudy solution. When the neutral flocculant was added, the coarsely dispersed precipitates remained. The solution above was clear. Example 7
  • topcoat red, topcoat white, primer and the clearcoat could each be detacked, with the precipitation occurring in finely dispersed form.
  • the coagulated products were partly sedimenting and partly floating.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Geology (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)

Abstract

L'invention concerne des coagulants de laques, cires et/ou enduits, contenant des composés d'hydroxyde à deux couches, des suspensions aqueuses contenant les coagulants, un procédé de production des coagulants et l'utilisation des coagulants et/ou de la suspension aqueuse. L'invention concerne notamment l'utilisation d'hydrotalcite, de pyroaurite et de magaldrate comme coagulants nouveaux dans des installations d'élimination de laques.
EP19910910614 1990-06-11 1991-06-03 Utilisation de composés d'hydroxyde à deux couches pour la coagulation Withdrawn EP0533728A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4018628 1990-06-11
DE4018628A DE4018628A1 (de) 1990-06-11 1990-06-11 Koagulationsmittel auf der basis von doppelschichthydroxid-verbindungen

Publications (1)

Publication Number Publication Date
EP0533728A1 true EP0533728A1 (fr) 1993-03-31

Family

ID=6408180

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910910614 Withdrawn EP0533728A1 (fr) 1990-06-11 1991-06-03 Utilisation de composés d'hydroxyde à deux couches pour la coagulation

Country Status (4)

Country Link
EP (1) EP0533728A1 (fr)
JP (1) JPH05507649A (fr)
DE (1) DE4018628A1 (fr)
WO (1) WO1991019679A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9203806D0 (en) * 1992-02-21 1992-04-08 Unilever Plc Sunscreen agents
US5474762A (en) * 1992-02-21 1995-12-12 Chesebrough-Pond's Usa Co. Division Of Conopco, Inc. Sunscreen agents
GB9316901D0 (en) * 1993-08-13 1993-09-29 Unilever Plc Sunscreen agents
DE19511016A1 (de) 1995-03-25 1996-09-26 Henkel Kgaa Kationische Schichtverbindungen, deren Herstellung und deren Verwendung als PVC-Stabilisatoren
US5976401A (en) * 1996-08-07 1999-11-02 Tomita Pharmaceutical Co., Ltd. Agent for removing phosphates, nitrates and nitrites from wastewater
EP1351887B1 (fr) * 2000-11-08 2008-10-01 Nycomed GmbH R hydratation de la poudre de magaldrate

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4504395A (en) * 1984-02-07 1985-03-12 Betz Laboratories, Inc. Paint spray booth detackification composition and method
DE3421270C2 (de) * 1984-06-07 1986-07-10 Zeller + Gmelin GmbH & Co, 7332 Eislingen Einkomponentenformulierung zur Ausfällung, Entklebung und Koagulierung von Unterbodenschutz auf Basis von Wachsen, wachsähnlichen Kunststoffen und Kunststoffdispersionen sowie von Kunstharzlacken in Naßabscheidern von Spritzlackieranlagen unter Erzielung eines sedimentierenden Lackschlamms und deren Verwendung
US4564464A (en) * 1984-12-27 1986-01-14 Betz Laboratories, Inc. Hectorite based paint spray booth detackifying slurries and methods of use thereof
EP0280440A1 (fr) * 1987-02-11 1988-08-31 Betz Europe, Inc. Procédé pour la dénaturation des peintures dans les cabines de peinture

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9119679A1 *

Also Published As

Publication number Publication date
JPH05507649A (ja) 1993-11-04
WO1991019679A1 (fr) 1991-12-26
DE4018628A1 (de) 1991-12-12

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