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WO1986006738A1 - Composition et procede d'inhibition du durcissement d'adhesifs en cyanoacrylate et compositions adhesives en cyanoacrylate a durcissement inhibe - Google Patents

Composition et procede d'inhibition du durcissement d'adhesifs en cyanoacrylate et compositions adhesives en cyanoacrylate a durcissement inhibe Download PDF

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Publication number
WO1986006738A1
WO1986006738A1 PCT/US1986/001047 US8601047W WO8606738A1 WO 1986006738 A1 WO1986006738 A1 WO 1986006738A1 US 8601047 W US8601047 W US 8601047W WO 8606738 A1 WO8606738 A1 WO 8606738A1
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mixtures
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PCT/US1986/001047
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Warren Gregory Lazar
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Priority to KR1019870700035A priority Critical patent/KR910001027B1/ko
Publication of WO1986006738A1 publication Critical patent/WO1986006738A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/30—Nitriles
    • C08F22/32—Alpha-cyano-acrylic acid; Esters thereof

Definitions

  • This invention relates to compositions containing cyanoacrylate adhesives that are temporarily inhibited from polymerizing and curing even in the presence of activating substances, such as metals, which normally catalyse polymer ⁇ ization of cyanocrylate adhesive compositions.
  • This invention also relates to compositions and methods for inhibiting polymerization and curing of cyanoacrylate adhesives.
  • cyanoacrylate compounds A major drawback of cyanoacrylate compounds is their tendency to polymerize rapidly and often uncontroll ⁇ ably when contacted or mixed with various activating sub- stances, especially substances that form ions in solution. Even trace quantities of such activators as organic salts, inorganic salts, metals, water, urea, oxides, etc., sub ⁇ stantially increase the rate of cyanoacrylate polymeriza ⁇ tion. This tendency has limited the usefulness of cyano- acrylate compounds to ordinary adhesive applications. If cyanoacrylate compounds could be mixed with sufficient quantities of various activating substances without polymerizing immediately, they would be useful in a wide variety of additional applications.
  • cyanoacrylates such as methyl-2-cyanoacrylate, ethyl-2-cyanoacrylate, pro ⁇ yl-2- cyanoacrylate, 2-ethylhexyl-2-cyanoacrylate, isobutyl-2- cyanoacrylate, n-butyl-cyanoacrylate, hexyl-, heptyl-, and octyl-cyanoacrylate, etc., represented a major technological advance in the bonding and adhesive art.
  • U.S. Patent No. 4,460,759 of Robins issued July 17, 1984 discloses a two-part cyanocrylate adhesive compo ⁇ sition.
  • One part of this composition contains weakly acidic or weakly ionic compounds as accelerators for polymerization, particularly when these compositions are used on wood substrates.
  • Such accelerators are said to include metal halides.
  • the first part contains acid gases and free-radical compounds as inhibitors.
  • Another object is to provide novel inhibiting- stabilizing compositions for cyanoacrylates that effective ⁇ ly delay onset and propagation of polymerization reations even in the presence of activators for such reactions.
  • Another object is to provide cyanoacrylate compo ⁇ sitions that are temporarily or permanently rendered non- reactive to activating substances.
  • Another object is to provide cyanoacrylate compositions that are electrically or thermally conductive and have such polymerization and stability characteristics or mechanical properties as make them suitable for use in the manufacture of electronic and microelectronic components
  • Another object is to expand the uses to which cyanoacrylate adhesive compositionis can be put by provid ⁇ ing compositions comprising cyanoacrylate monomers that are controllably inhibited towards polymerization and at the same time yield polymers with the desired degree of cure and stability.
  • a further object is to prepare cyanoacrylate adhesive compositions that can be spray-coated in place using inter alia on artists' air brush.
  • Yet another object is to provide methods for inhibiting the polymerization of cyanoacrylate compounds and for preparing polymerization-inhibited and stabilized compositions containing cyanoacrylate compounds and activa ⁇ tors.
  • Summary of the Invention One aspect of this invention is directed to a composition comprising at least one organic acid and at least one hydrated or anhydrous base metal fluoride, chloride, bromide or iodide. The composition is useful in inhibiting-stabilizing cyanoacrylates.
  • Another aspect of the invention is directed to a cyanoacrylate composition temporarily or permanently inhibited from polymerizing, the composition including an organic acid and at least one hydrated or anhydrous metal fluoride, chloride, bromide or iodide.
  • the composition may include a filler that is ordinarily an activator of cyano ⁇ acrylate polymerization.
  • a filler that is ordinarily an activator of cyano ⁇ acrylate polymerization.
  • Yet another aspect of the invention relates to a method for inhibiting cyanoacrylates against polyme ization by incorporating either to said cyanoacrylates or to an activator additive thereof an inhibitor comprising a liquid organic acid and an anhydrous or hydrated metal fluoride, 0 chloride, bromide or iodide, prior to mixing said cyanocry- late with said activator-additive, or simultaneously therewith.
  • unpo- 5 lymerized (or partially polymerized) cyanoacrylate composi ⁇ tions can be temporarily (or permanently) inhibited from reacting with polymerization-activating materials (activa ⁇ tors) and at the same time stabilized against incomplete cure and/or premature decomposition.
  • This inhibition-stabilization of the cyanoacryl ⁇ ate is accomplished by incorporating an inhibitor-stabilizer either in the unpolymerized (or partially polymerized) cyanoacrylate or in an activator that will serve as an additive or filler of the final composition, said inhibitor- 5 stabilizer comprising:
  • the inhibitor-stabilizer is preferably incorpo- Q rated in the cyanoacrylate adhesive (monomer or prepolymer) prior to exposure of the latter to an activator, such as a metal, oxide, ionic solvent, salt, water or urea. However, it can also be incorporated to the activator prior to mixing it with the cyanoacrylate.
  • the ingredients of the - inhibitor-stabilizer must be premixed and may not be separately incorporated in the cyanoacrylate or activator.
  • the inhibitor-stabilizer also in ⁇ cludes a polar solvent to facilitate mixing with and solubility in the cyanoacrylate (or activator additive).
  • a solvent is particularly desirable. Additional solvent may be used when the in ⁇ hibitor-stabilizer is mixed with the cyanoacrylate to facilitate mixing. This additional solvent may but need not be a polar solvent; it can be any suitable organic solvent.
  • Suitable solvents for the inhibitor include polar organic and inorganic solvents, such as water, lower aliphatic alcohols, lower aliphatic ketones, lower aliphatic ethers of carboxylic acids, lower alkylene glycols, lower alkylene glycol ethers, lower aliphatic esters of carboxylic acids, carboxylic acid nitriles, and mixtures thereof.
  • polar organic and inorganic solvents such as water, lower aliphatic alcohols, lower aliphatic ketones, lower aliphatic ethers of carboxylic acids, lower alkylene glycols, lower alkylene glycol ethers, lower aliphatic esters of carboxylic acids, carboxylic acid nitriles, and mixtures thereof.
  • Methyl chloride, formaldehyde and dimethyl sulfoxide are also useful as solvents in the present invention.
  • Preferred solvents are: water; acetone, methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, ethyl butyl ketone, acetyl acetone; methanol, ethanol, propanol, isopropanol, butanol, isobutanol, and hexanol, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and methyl-CELLOSOLVE R -acetate (methyl-2-ethoxy- ethanol acetate; CELLOSOLVE R is a trademark of Union Carbide Corporation); ethyl ether, dimethyl ether, and diethylene glycol ethyl ether (diethyl-CARBITOL R ; a trade ⁇ mark of Union Carbide Corporation); methyl-CELLOSOLVE, butyl CELLOSOLVE, methyl glycol ether
  • Preferred acids for the inhibitor-stabilizer are formic acid, acetic acid, propionic acid, butanoic acid, lactic acid, pentenoic acid, carbonic acid, etc. Most preferred is formic acid.
  • Preferred metal halide salts are: FeCl_; FeCl 3 .6H 2 0; LiF; CdCl 2 ; CdCl 2 .2-1/2H 2 0; MgBr.6H H 0; SnBr 4 ; GeCl 4 ; MgCl 2 ; ZnCl 2 ; ZnBr; MnCl 2 .4H 2 0;
  • Non-polar solvents that can be added to the in- hibited cyanoacrylate composition include without limita ⁇ tion plasticizers, such as dibutyl phthalate, tricresyl phosphate, dimethyl phthalate, etc.
  • suitable relative proportions of the ingredients of the inhibitor-stabilizer i.e. the acid, salt and solvent (if any) are: acid — about 0.002 - 55%; salt — about 0.002 - 50%; and solvent — about 0 - 75% by weight.
  • the inhibitor-stabilizer can be about 0.10-55%.
  • the above proporltions are given by way of guide ⁇ lines.
  • the actual amount of the inhibiting-stabilizing composition will depend on how long it is desired to delay the onset of polymerization for the final cyanoacrylate mixture (i.e. after addition of the activating substance) and, to a lesser extent, on the ability of the activator to catalyze cyanoacrylate polymerization. It should be noted that as the percentage compositive of acid and salt is increased, the cure time of the adhesive composition increases. The duration of the stabilization or inhibition provided by a given stabilizer/acrylate formulatin is also dependent upon the ambient temperature to which the material is exposed.
  • the incorporation of the inhibitor-stabilizer renders the cyanoacrylate non-reactive to activating substances for a period of time at least long enough to permit mixing of the cyanocrylate with the activator and any processing, storage, or fabrication necessary for the particular end application envisioned.
  • Metal-filled cyanoacrylate polymers can be used in die and wire bonding of microelectronic circuits instead of solder. In addition, they can be used as conductive terminals for resistors, as electrodes for capacitors and for a variety of functions in thick-film hybrid microelectronic circuits.
  • the metal-filled cyano ⁇ acrylate compositions can be applied to circuit boards by conventional screening methods. Electrically conductive cyanoacrylate compositions preferably contain about 0.5 - 7.0% of inhibitor, 0.05 - 0.4% acid, 0.08 to 0.8% salt and about 0.4% to 10.0% solvent by weight of the cyanoacrylate monomer.
  • conductive cyanoacrylates are in high-conductivity metallization films and coatings for plastics, paper, mica, ceramics and other non-conductive materials.
  • the metallized films and coatings allow direct soft-soldering without the use of flux and may be further metal-coated by electroplating.
  • Such films and coatings are useful in electronic and microwave applications as connectors, contacts, magnetic shields, especially in metal shields that are used to protect from Radio Frequency Interference (RFI) and Electro Magnetic Interference (EMI) and capacitor terminals. They can be applied by brushing, dipping, or spraying, or by conventional screening tech ⁇ niques using standard 180 to 200 mesh screens.
  • These conductive, film-forming cyanoacrylate compositions preferably contain about 1.0 - 7.0% inhibitor- stabilizer (0.07 to 0.6 acid, 0.2 to 1.3% salt) and about 1.0 - 10.0% solvent.
  • Suitable metal fillers for electrically conduc ⁇ tive cyanoacrylates include one or more of palladium, silver, copper, tin, gold, and platinum and other high-conductivity metals.
  • the metal filler may first be combined with the inhibitor composition and the metal- containing inhibitor may subsequently be introduced into the cyanocrylate. This makes it possible to package these constituents separately for mixing by the consumer just prior to use (as an A&B component system).
  • thermo- conductive materials can be used as heat sinks for the base and mounting stud of transistors, diodes, and rectifiers; and as coupling agents to reduce thermal contact resistance.
  • Suitable fillers for this purpose include base metals, such as iron, aluminum, tin, and metal oxides that are not electrically conductive, etc.
  • thermally conductive cyanoacryl ⁇ ates is for application between, e.g., semiconductor power devices and heat sinks; power resistors and chassis mounts; thermostats and mounting surfaces; and anywhere else where
  • thermoelectric devices e.g. in transformers as anti-static layers and heat sinks
  • heat dissipaters for electronic devices.
  • Suitable fillers for this purpose are base metal oxides
  • Thermally conductive cyanoacrylate compositions according to this invention preferably contain about 1.0 to 7.0% inhibitor 0.07 to 0.6% acid, 0.2 to 1.3% salt and
  • thermally conductive cyanocrylates of the present invention can be used in place of other thermocon- ductive plastic materials including thermoconductive expoxies containing alumina or other metals.
  • cyanoacrylates may be employed to join heat sinks and other components to printed circuit boards and in like applica ⁇ tions.
  • compositions that can be used in the manufacture of photocells used for light sensors, light-controlled relay operations, exposure meters, fire detectors, photo ⁇ meters, lamp controls, liquid level indicators and a
  • Suitable fillers include cadmium sulfide, cadmium selenide and cadmium-sulfoselenide.
  • Compositions used in these applications preferably contain about 0.5 - 0.2% acid about 0.08 - 0.24% salt and about 1 - 11% solvent.
  • fillers can be incorporated to the inhibited-stabilized cyanoacryl ⁇ ates contemplated herein.
  • these include one or more of plasticizers, silicones, silica, polymeric fillers, fibers, magnetic resins, pharmaceuticals, dyes, water, non-polar solvents, radioactive materials, viscosity modifiers, human and animal skin, etc.
  • This invention is for use with any cyanoacrylate monomer (or prepolymer) including but not limited to those set forth in the Background of the Invention, or mixtures thereof.
  • a stabilizing-inhibiting composition with or without a solvent is formed by mixing the following ingredients:
  • Formula (C) Formula (D) 23.5% FeCl 3 .6H 2 0 50.0% SnCl 2 .6H 2 0 23.5 Acetone 53.0% Formic Acid 50.0% Acetic Acid
  • An inhibited-stabilized methyl-2-cyanoacrylate composition is made by mixing one of the stabilizing- inhibiting compositions according to Example 1 with methyl- 2-cyanoacrylate monomer and a solvent to improve mixing.
  • the resulting compositions in weight percent are shown in the table below: Inhibited Cy.anoacrylate I II III IV
  • thermoconductive cyanoacrylate composition is formed from the inhibited-stabilized cyanoacrylate composi ⁇ tions No. Ill of Example 2 and the following ingredients: Inhibited-stabilized CA. 50.0 (III) 49.0 (III) 54.0 (III)
  • thermoconductive compositions will not polymerize for about 24 hours from incorporation of the metal powders.
  • a fiber-filled cyanoacrylate composition is prepared as outlined above, except that the cyanoacrylate compositions No. IV and II were used.
  • compositions will not polymerize for about 24 hours after incorporation of the fibers. They can be used as 0 adhesives, especially in high impact resistant applications and in joining sheet and cloth materials (e.g. textile fabrics, leather and vinyl sheets).
  • sheet and cloth materials e.g. textile fabrics, leather and vinyl sheets.
  • a flexible plasticized cyanoacrylate composition 5 for use as a caulking material is prepared by mixing the inhibitor-stabilized cyanoacrylate of Example 2 with the following ingredients:
  • a sprayable cyanoacrylate composition containing 5 finely divided silver particles was prepared by admixing a stabilized-inhibited cyanoacrylate composition (Formula I of Example 2 prepared with inhibitor Formula E of Example 1 ) with 30 percent by weight of the stabilized inhibited cyanocrylate composition of finely divided metallic silver 0 particles (average size 200-300 mesh).
  • the siler powder is stirred in with a single blade electric laboratory mixer until an essentially homogeneous silver dispersion is obtained.
  • the silver containing cyanoacrylate mixture is loaded into the reservoir of a Badger brand artists' air _ brush.
  • the brush is connected to a source of pressurized air (30-40 psi).
  • Plastic sheets (each approximately 2" x 2" x 1/4") of Styrene, ABS and acrylic (plexiglass) were laid on a flat surface. A solution of 5% toluidine was coated on the upper surface of the ABS plastic sheet and allowed to dry at room temperature (15 * C).
  • the silver-containing cyanoacrylate composition was sprayed across the entire upper surface of the three plastic sheets (with the nozzle of the air brush held approximately eight inches from the surface of each sheet) using broad sweeping strokes.
  • the cyanocrylate on the ABS sheet cured in approximately 3 minutes.
  • the cyanoacrylate joining the styrene sheets cured to working condition (i.e. to a condition in which the sheets could not be pulled apart by hand) in approxi ⁇ mately fifteen minutes.
  • the cyanoacrylate on the acrylic sheet cured within one hour.
  • compositions of the present invention employed in the specific embodiments described above is basically the same regardless of the particular cyanoacrylate, activator-filler and inhibitor- stabilizer used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Sealing Material Composition (AREA)
  • Polymerisation Methods In General (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne des compositions et des procédés d'inhibition du durcissement d'adhésifs en cyanoacrylate et des compositions adhésives en cyanoacrylate à durcissement inhibé. Les compositions à durcissement inhibé comprennent un acide carboxylique organique et un chlorure, fluorure, bromure ou iodure métallique hydraté ou anhydre.
PCT/US1986/001047 1985-05-17 1986-05-14 Composition et procede d'inhibition du durcissement d'adhesifs en cyanoacrylate et compositions adhesives en cyanoacrylate a durcissement inhibe Ceased WO1986006738A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019870700035A KR910001027B1 (ko) 1985-05-17 1986-05-14 시아노아크릴레이트 중합 억제 조성물

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US73544085A 1985-05-17 1985-05-17
US735,440 1985-05-17

Publications (1)

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WO1986006738A1 true WO1986006738A1 (fr) 1986-11-20

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PCT/US1986/001047 Ceased WO1986006738A1 (fr) 1985-05-17 1986-05-14 Composition et procede d'inhibition du durcissement d'adhesifs en cyanoacrylate et compositions adhesives en cyanoacrylate a durcissement inhibe

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EP (1) EP0222888A4 (fr)
JP (1) JPS63500247A (fr)
KR (1) KR910001027B1 (fr)
WO (1) WO1986006738A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0585949A3 (fr) * 1992-09-04 1994-04-13 Tomas Meinen Procédé et dispositif pour le traitement et l'application d'adhesifs cyanoacryliques
WO2004045664A1 (fr) * 2002-11-20 2004-06-03 Smith & Nephew Plc Adhesif medical angiogenique a base de cyanoacrylate
CN103945961A (zh) * 2011-09-06 2014-07-23 汉高知识产权控股有限责任公司 用于焊膏的涂覆有二官能或多官能缺电子烯烃的金属粉末
US8808620B1 (en) 2012-02-22 2014-08-19 Sapheon, Inc. Sterilization process design for a medical adhesive
US9561023B2 (en) 2009-02-20 2017-02-07 Covidien Lp Enhanced ultrasound visualization of intravascular devices
US9592037B2 (en) 2009-02-20 2017-03-14 Covidien Lp Systems for venous occlusion for the treatment of venous insufficiency
US20170369967A1 (en) * 2016-06-24 2017-12-28 Enviroleach Technologies Inc. Methods, Materials and Techniques for Precious Metal Recovery
US10526682B2 (en) 2017-07-17 2020-01-07 Enviroleach Technologies Inc. Methods, materials and techniques for precious metal recovery

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7463684B2 (ja) * 2019-10-03 2024-04-09 株式会社リコー 液体組成物セット、収容容器セット、硬化物形成装置、硬化物形成方法、及び液体組成物
JP7746633B1 (ja) * 2023-11-13 2025-09-30 株式会社クラレ １，１－ジシアノエチレン含有組成物、硬化物、積層体及び１，１－ジシアノエチレン含有組成物の製造方法

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US4556700A (en) * 1984-01-30 1985-12-03 Loctite Limited Instant adhesive composition utilizing calixarene accelerators

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Title
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0585949A3 (fr) * 1992-09-04 1994-04-13 Tomas Meinen Procédé et dispositif pour le traitement et l'application d'adhesifs cyanoacryliques
WO2004045664A1 (fr) * 2002-11-20 2004-06-03 Smith & Nephew Plc Adhesif medical angiogenique a base de cyanoacrylate
US11369384B2 (en) 2009-02-20 2022-06-28 Covidien Lp Systems for venous occlusion for the treatment of venous insufficiency
US10702276B2 (en) 2009-02-20 2020-07-07 Covidien Lp Systems for venous occlusion for the treatment of venous insufficiency
US9561023B2 (en) 2009-02-20 2017-02-07 Covidien Lp Enhanced ultrasound visualization of intravascular devices
US9592037B2 (en) 2009-02-20 2017-03-14 Covidien Lp Systems for venous occlusion for the treatment of venous insufficiency
US10143455B2 (en) 2011-07-20 2018-12-04 Covidien LLP Enhanced ultrasound visualization of intravascular devices
CN103945961A (zh) * 2011-09-06 2014-07-23 汉高知识产权控股有限责任公司 用于焊膏的涂覆有二官能或多官能缺电子烯烃的金属粉末
US9427829B2 (en) 2011-09-06 2016-08-30 Henkel IP & Holding GmbH Di- or poly-functional electron deficient olefins coated metal powders for solder paste
US8808620B1 (en) 2012-02-22 2014-08-19 Sapheon, Inc. Sterilization process design for a medical adhesive
US9339575B2 (en) 2012-02-22 2016-05-17 Covidien Lp Sterilization process design for a medical adhesive
US9084835B2 (en) 2012-02-22 2015-07-21 Covidien Lp Sterilization process design for a medical adhesive
US20170369967A1 (en) * 2016-06-24 2017-12-28 Enviroleach Technologies Inc. Methods, Materials and Techniques for Precious Metal Recovery
US10563283B2 (en) * 2016-06-24 2020-02-18 Enviroleach Technologies Inc. Methods, materials and techniques for precious metal recovery
US10526682B2 (en) 2017-07-17 2020-01-07 Enviroleach Technologies Inc. Methods, materials and techniques for precious metal recovery

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KR880700040A (ko) 1988-02-15
EP0222888A1 (fr) 1987-05-27
KR910001027B1 (ko) 1991-02-19
JPS63500247A (ja) 1988-01-28
EP0222888A4 (fr) 1989-02-16

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