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WO1996020242A1 - Compositions de resine durcissable - Google Patents

Compositions de resine durcissable Download PDF

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Publication number
WO1996020242A1
WO1996020242A1 PCT/EP1995/004878 EP9504878W WO9620242A1 WO 1996020242 A1 WO1996020242 A1 WO 1996020242A1 EP 9504878 W EP9504878 W EP 9504878W WO 9620242 A1 WO9620242 A1 WO 9620242A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyanate ester
cyanate
represented
resin
formula
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.)
Ceased
Application number
PCT/EP1995/004878
Other languages
English (en)
Inventor
Kanichi Yokota
Yasunori Shimizu
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.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaeten Chemie AG
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
Priority claimed from JP33661594A external-priority patent/JPH08176299A/ja
Priority claimed from JP3184195A external-priority patent/JPH08208808A/ja
Application filed by Ciba Geigy AG, Ciba Spezialitaeten Chemie AG filed Critical Ciba Geigy AG
Publication of WO1996020242A1 publication Critical patent/WO1996020242A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065—Preparatory processes
    • C08G73/0655—Preparatory processes from polycyanurates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • 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
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
    • H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0393—Flexible materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
    • H05K2201/03—Conductive materials
    • H05K2201/0332—Structure of the conductor
    • H05K2201/0335—Layered conductors or foils
    • H05K2201/0355—Metal foils

Definitions

  • the present invention relates to a method for bonding a copper foil to a substrate comprising a polymeric compound, a copper-lined laminate and a TAB film carrier tape produced by using this method.
  • the method for bonding the copper foil to the substrate according to the present invention comprises the use of a resin composition as adhesive which composition is based on a dicyanate ester and/or a derivative thereof as main ingredient, and further comprises a curing catalyst, and as optional ingredient an epoxy resin.
  • TAB carrier films are a special embodiment of such flexible copper-lined laminate boards.
  • TAB carrier films are used for connecting the electrical contact pads of a chip (bumps) with a circuit board in order to meet the modern requirements of dense packaging and fine pitch, the three layer type mainly (but not exclusively) for mounting LCD drivers.
  • the TAB technology is, for instance, described in the U.S. Patents (US-A-) 3,689,991 and 3,706,409.
  • the copper foil is then structured to provide the required lines for contacting the chip. These lines are usually metal plated and then connected with the bumps of the chip, usually by thermo- compression ("inner lead bonding"). For protection of the electrical contacts the contact area is casted with a resin.
  • a resin composition to be used as an adhesive for producing a three layer type TAB film carrier tape must provide a high heat resistance and a high flexibility, as detailed in the known papers cited above.
  • a known adhesive composition for TAB carrier tapes comprises a bisphenol A type epoxy resin as main ingredient and dicyandiamide as a curing agent.
  • a thermoplastic resin must additionally be used in order to get a suitable flexibility.
  • a reactive liquid rubber such as a liquid acrylonitrile- butadiene copolymer rubber having reactive groups such as carboxyl group or the like at both molecular terminals, or the like is used in addition to the above-mentioned ingredients.
  • A represents a direct single bond or a group >CR 5 R 6 and
  • R T to R 6 each independently represents a hydrogen atom, methyl group
  • R. to R 3 each independently represents a hydrogen atom, methyl group or halogen atom, and n represents an integer of 0 to 6;
  • cyanate ester or prepolymer thereof [A] is selected from the group consisting of: a phenol novolac polycyanate represented by the following formula (3):
  • n an integer of 0 to 6
  • hexafluorobisphenol A dicyanate represented by formula (4):
  • R, to R 4 each and independently represents a hydrogen atom, a methyl group, a CF 3 group or a halogen atom
  • a cyanate ester resin obtained by polymerizing 0-50 % of the cyanate groups of the said cyanate ester resins
  • the curing catalyst [B] used in the method according to the instant invention is preferably at least one compound selected from a metal compound represented by formula (7): Y-Z (7) wherein Y represents a metallic ion selected from Mn 2 ⁇ Mn 3+ , Co 2 ⁇ Co 3 ⁇ Cu 2+ , Zn 2+ , Ni 2+ , Al 3+ , and Fe 3 ⁇ and Z represents an organic anion, a phenol compound, a tertiary amine compound or a mixture thereof.
  • Y represents a metallic ion selected from Mn 2 ⁇ Mn 3+ , Co 2 ⁇ Co 3 ⁇ Cu 2+ , Zn 2+ , Ni 2+ , Al 3+ , and Fe 3 ⁇
  • Z represents an organic anion, a phenol compound, a tertiary amine compound or a mixture thereof.
  • the said organic anion may, for instance, be selected from the naphthenic acid anion, octylic acid anion and the acetylacetonate anion.
  • Examples of said metal compound include manganese octylate, manganese naphthenate, cobalt octylate, cobalt naphthenate, copper octylate, copper naphthenate and the like.
  • phenol compound phenol, cresol, Bisphe ⁇ ol A, nonylphenol, dinonylphenol, salicylic acid and the like can be referred to.
  • tertiary amine compound imidazole, 2- methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole and the like can be referred to. Combined mixtures of more than one of these compounds are also usable, if desired.
  • the curing catalyst is preferably used in an amount of 0.001 -10, preferably from 0.01 -10 parts by weight per 100 parts by weight of the cyanate ester component [A].
  • an epoxy resin may optionally be mixed, too.
  • Said epoxy resin may be any epoxy resin so far as it has at least two glycidyl groups.
  • a bisphenol A type epoxy resin having, for instance, the epoxy equivalent 189 and obtained in a known manner by reacting Bisphenol A and epichlorohydrin can be referred to.
  • bisphenol A type epoxy resin a variety of ones different in the degree of polymerisation can also be used.
  • epoxy resins into which halogen atoms have been introduced for the purpose of giving the resin a flame retardance are also usable.
  • epoxy resin the polycondensates formed by reaction between tetrabromobisphenol A and epichlorohydrin may be mentioned.
  • a specific example of such epoxy resin has a bromine content 49 % by weight and epoxy equivalent 460 g/eq.
  • novolac type epoxy resins may be used.
  • the epoxy resin forming the component [C] of the used resin composition comprises at least one epoxy resin selected from: a bisphenol A epoxy resin having an epoxy equivalent of 170 to 1000 grams per equivalent and a bromine content of 0 to 60% by weight,
  • R. to R 3 each independently represents a hydrogen atom, methyl group or halogen group and n represents an integer of 0 to 6, and
  • the epoxy resins are used in an amount ranging from 0 to 400 parts by weight per 100 parts by weight of the cyanate ester compound [A].
  • the amount of epoxy resin is 0 part by weight, that is when no epoxy resin is used at all, the cyanate ester compound [A] cures alone forming triazine rings.
  • an epoxy resin is used in combination with the cyanate ester compound [A]
  • a reaction between cyanate groups and glycidyl groups also progresses in parallel while forming oxazolidone rings.
  • the reaction between glycidyl group and cyanate group can take place so long as any quantity of unreacted glycidyl group remains in the reaction system.
  • a curing agent for the epoxy resin may additonally be used.
  • said curing agent for epoxy resin include organic acid anhydrides, amines, phenols, and the like. Nevertheless, the amount of epoxy resin should be at most 400 parts by weight per 100 parts by weight of the cyanate ester compound [A].
  • the resin composition used as adhesive for the purposes of the present invention may also contain a solvent (diluent) such as methyl ethyl ketone, acetone or the like for the purpose of regulating viscosity of the resin composition, and further components, like a curing agent or an additional flexibilizer such as reactive liquid rubber (for example, liquid acrylonitrile-butadiene copolymer rubber having reactive groups such as carboxyl groups or the like at both molecular terminals), thermoplastic resin or the like.
  • a solvent such as methyl ethyl ketone, acetone or the like
  • an additional flexibilizer such as reactive liquid rubber (for example, liquid acrylonitrile-butadiene copolymer rubber having reactive groups such as carboxyl groups or the like at both molecular terminals), thermoplastic resin or the like.
  • the resin compositions used in the instant invention are usually mixed together in the state of liquid substances. The temperature should not exceed 150°C at this stage in order to avoid premature curing.
  • a solvent such as methyl ethyl ketone, acetone or the like can be used.
  • a solvent is necessary for regulating viscosity. It is preferable from the practical point of view to adjust viscosity of the composition so as to fall in a range of from 100 centipoises to 50,000 centipoises by adding the solvent.
  • the resin compositions used in the present invention are relatively easy to produce industrially, by the use of an agitating apparatus equipped with an appropriate heater.
  • the resin compositions are cured by heating them to a temperature of more than 150°C, preferably of more than 170°C, to 300°C, either in one step or stepwise.
  • the compositions may firstly be heated to a temperature ranging from 150°C to 230°C.
  • a post-cure at temperatures from 200°C to 300°C may follow, is however optional.
  • the total curing time may range from a few minutes to about 10 hours. It is preferred to press the substrate and the copper-foil on one another while curing the adhesive composition, using a pressure of, for instance, about 15 kg/cm 2 .
  • a cured product obtained from the resin composition used in the method of the present invention is excellent not only in heat resistance but also in adhesiveness, particularly to polyimide film and copper foil, as well as in its electrical properties, and therefore very suitable for use in the manufacture of high-performance copper-lined laminate boards and particularly flexible copper-lined laminate board and TAB film carrier tapes.
  • the invention therefore also relates to a, preferably flexible, copper-lined laminate board produced by using the method for bonding a copper foil to a substrate comprising a polymeric compound which has been described above, and to a corresponding TAB film carrier tape of the three layer type.
  • Example 1 A resin composition is prepared by charging a reactor equipped with a stirrer with 100 parts by weight of a cyanate resin of the following formula (3)
  • the mixture thus obtained is formed into a coating film having a final thickness of 35 ⁇ m by means of a bar coater on a polyimide film (Capton 200H, manufactured by Toray Co.) and preliminarily cured at 170°C for 5 minutes. Then, a copper foil (CF T-8, manufactured by Fakuta Metallic Foil and Powder Co.) is superposed on the polyimide film, and pressed at 177°C for one hour under a pressure of 15 kg cm 2 . Then, it is post-cured at 230°C for 5 hours to obtain a flexible copper-lined laminate board.
  • CF T-8 manufactured by Fakuta Metallic Foil and Powder Co.
  • a resin composition containing no methyl ethyl ketone is prepared by adding 1 part by weight of nonylphenol and 0.1 125 part by weight of a solution of manganese octylate in mineral spirit (content of manganese ion 8 %) to 100 parts by weight of the same cyanate ester resin as above, and stirring the resulting mixture at 90°C for one hour.
  • the composition thus obtained is cast in a die having a length of 10 cm, a width of 10 cm and a thickness of 2 mm, and heated at 177°C for one hour and subsequently post- cured at 230°C for 5 hours. On the cured product thus obtained, dielectric constant, dielectric loss and glass transition point are measured.
  • Example 2 The procedure of Example 1 is repeated, except that the cyanate ester resin used in Example 1 is replaced with a cyanate ester resin represented by the following formula (4):
  • Example 3 The procedure of Example 1 is repeated, except that the cyanate ester resin used in Example 1 is replaced with a cyanate ester resin represented by the following formula (5):
  • Example 4 The procedure of Example 1 is repeated, except that the cyanate ester resin used in Example 1 is replaced with a cyanate ester resin represented by the following formula (6):
  • Example 5 To a reactor equipped with a stirrer are charged 55 parts by weight of a cyanate resin of the following formula (3)
  • the mixture thus obtained is applied to a polyimide film (Capton 200H, manufactured by Toray Co.) by means of a bar coater to form a coating film having a final thickness of 35 ⁇ m and then precured at 170°C for 5 minutes. Then, a copper foil (CF T-8, manufactured by Fakuta Metallic Foil and Powder Co.) is superposed on the polyimide film, and pressed at 177°C for one hour under a pressure of 15 kg/cm 2 . Then, it is post-cured at 210°C for 5 hours to obtain a flexible copper-lined laminate board.
  • CF T-8 manufactured by Fakuta Metallic Foil and Powder Co.
  • a resin composition containing no methyl ethyl ketone is obtained by charging 55 parts by weight of the same cyanate ester resin as above, bisphenol A type epoxy resin (epoxy equivalent: 189), 0.018 part by weight of a solution of manganese octylate in mineral spirit (content of manganese ion 8 %) and 0.012 part by weight of 2-methylimidazole, and stirring the resulting mixture at 90°C for one hour.
  • the composition thus obtained is poured into a mold having a length of 10 cm, a width of 10 cm and a thickness of 2 mm, and heated at 177°C for one hour and subsequently post-cured at 210°C for one hour.
  • Dielectric constant, dielectric loss and glass transition temperature of the resulting cured product are measured.
  • Example 6 The procedure of Example 5 is repeated analogously , except that the cyanate ester resin used in Example 5 is replaced with a cyanate ester resin represented by the following formula (4):
  • Example 7 The procedure of Example 5 is repeated analogously, except that the cyanate ester resin used in Example 5 is replaced with a cyanate ester resin represented by the following formula (5):
  • Example 8 The procedure of Example 5 is repeated, except that the cyanate ester resin used in Example 5 is replaced with a cyanate ester resin represented by the following formula (6):
  • Example 9 The procedure of Example 5 is repeated, except that the cyanate ester resin used in Example 5 is replaced with a cyanate ester resin represented by the above- mentioned formula (6) in which 30 % of the cyanate groups have previously been reacted.
  • a resin composition is prepared by charging a reactor equipped with a stirrer with 100 parts by weight of a brominated Bisphenol A type epoxy resin (epoxy equivalent 480, bromine content 20.5 %, 2.68 parts by weight of dicyandiamide, 0.1 part by weight of 2- methylimidazole, 33.33 parts by weight of methyl ethyl ketone and 34 parts by weight of methyl cellosolve, and stirring the mixture at 80°C for one hour under a reflux condenser.
  • a brominated Bisphenol A type epoxy resin epoxy equivalent 480, bromine content 20.5 %, 2.68 parts by weight of dicyandiamide, 0.1 part by weight of 2- methylimidazole, 33.33 parts by weight of methyl ethyl ketone and 34 parts by weight of methyl cellosolve
  • the mixture thus obtained is formed into a coating film having a final thickness of 35 ⁇ m by means of a bar coater on a polyimide film (Capton 200H, manufactured by Toray Co.) and preliminarily cured at 170°C for 5 minutes. Then, a copper foil (CF T-8, manufactured by Fukuta Metallic Foil and Powder Co.) is superposed on the polyimide film, and pressed at 170°C for one hour under a pressure of 15 kg/cm 2 .
  • CF T-8 manufactured by Fukuta Metallic Foil and Powder Co.
  • the resin composition is introduced into an evaporator and stirred at 100°C for 2 hours to remove the solvent therefrom.
  • the solvent- free resin composition thus obtained is cast into a die having a length of 10 cm, a width of 10 cm and a thickness of 2 mm and cured at 170°C for one hour.
  • Adhesive strength Measured according to the procedure mentioned in JIS-C6481.
  • Comparative Example In Table 1 and Table 2, comparison of the Examples of the present invention with Comparative Example demonstrates an effectiveness of the present invention.
  • the formulation shown in Comparative Example corresponds to that of a resin composition used in a copper-lined laminate board generally called FR-4. It is understandable from Table 1 and Table 2 that the flexible copper-lined laminate boards and cured products formed from the resin compositions of the present invention are superior in adhesiveness, heat resistance and electrical properties.
  • the resin composition used in the method according the present invention contains a cyanate ester compound of specified structure, it exhibits excellent heat resistance, electrical properties, flexibility and adhesiveness simultaneously which are contradictory to one another.
  • the cured product obtained from the resin composition of the present invention is superior not only in heat resistance but also in the adhesive strength of polyimide film and copper foil and in electrical properties, which makes the cured product of the present invention suitable for use in the production of flexible copper-lined laminate board and TAB film carrier tape.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Procédé de fixation d'une feuille de cuivre sur un support comprenant un composé polymère. Ce procédé consiste à enduire le support d'une composition de résine comprenant un composé spécifique d'ester de cyanate [A], par exemple un polycyanate de novolaque phénolique, un dicyanate d'hexafluoro-bisphénol A, un dicyanate d'éthylidène bis-4,1-phénylène, un dicyanate de 4,4'-(1,3-phénylène-diisopropylidène)diphényle, ou des résines d'esters de cyanate obtenues par polymérisation de 0 à 50 % des groupes cyanate de celles-ci, et des mélanges de plus d'un de ces composés d'esters de cyanate, un catalyseur chimique [B] (composé métallique, composé phénolique, composé imidazolique), et éventuellement une résine époxyde [C]. Le procédé consiste ensuite à mettre la face enduite du support en contact avec la feuille de cuivre et à faire subir un traitement thermique à la composition de résine. Ce procédé est particulièrement adapté à la production de stratifiés recouverts de cuivre et de rubans porteurs de montage (TAB), qui font également l'objet de la présente invention.
PCT/EP1995/004878 1994-12-26 1995-12-11 Compositions de resine durcissable Ceased WO1996020242A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP33661594A JPH08176299A (ja) 1994-12-26 1994-12-26 樹脂組成物
JP6/336615 1994-12-26
JP3184195A JPH08208808A (ja) 1995-01-30 1995-01-30 硬化性樹脂組成物
JP7/31841 1995-01-30

Publications (1)

Publication Number Publication Date
WO1996020242A1 true WO1996020242A1 (fr) 1996-07-04

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WO (1) WO1996020242A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5969036A (en) * 1997-06-20 1999-10-19 The Dexter Corporation Epoxy-containing die-attach compositions
WO2001081492A1 (fr) * 2000-04-19 2001-11-01 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Adhesif a base de cyanate, destine a, et en combinaison avec des revetements d'adherence, ainsi que procede de realisation de revetements d'adherence adherant a un support
US6342577B1 (en) * 1997-07-24 2002-01-29 Loctite Corporation Thermosetting resin compositions useful as underfill sealants
US6372861B1 (en) * 1999-02-09 2002-04-16 Bakelite A.G. Cyanate resin, polyepoxide and metal complex curing agent
US6632893B2 (en) 1999-05-28 2003-10-14 Henkel Loctite Corporation Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners
WO2014210236A1 (fr) * 2013-06-28 2014-12-31 Saint-Gobain Performance Plastics Corporation Mélanges de résines de cyanate et radomes les comprenant
US9879163B2 (en) 2014-06-06 2018-01-30 General Electric Company Composition for bonding windings or core laminates in an electrical machine, and associated method
US9911521B2 (en) 2014-06-06 2018-03-06 General Electric Company Curable composition for electrical machine, and associated method
CN108264763A (zh) * 2016-12-30 2018-07-10 比亚迪股份有限公司 氰酸酯树脂原料组合物和氰酸酯树脂以及氰酸酯树脂金属复合材料和其制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3658623A (en) * 1969-07-14 1972-04-25 Bayer Ag Process for bonding non-porous materials by means of polyfunctional aromatic cyanic acid esters
DE2947112A1 (de) * 1978-11-22 1980-05-29 Mitsubishi Gas Chemical Co Vernetzbare ueberzogene platten oder boegen und hieraus gebildete schichtgebilde
JPS5863439A (ja) * 1981-10-13 1983-04-15 三菱瓦斯化学株式会社 キヤリアテ−プ用連続シ−ト
DE4125420A1 (de) * 1991-07-29 1993-02-04 Inst Polymerenchemie Erich Cor Elektrisch hochwertige bindemittel zur herstellung von basismaterial fuer leiterplatten
DE4224835A1 (de) * 1992-07-28 1994-02-03 Fraunhofer Ges Forschung Elektrisch hochwertiges Basismaterial für Leiterplatten
US5319244A (en) * 1991-12-13 1994-06-07 International Business Machines Corporation Triazine thin film adhesives
EP0612782A1 (fr) * 1993-02-23 1994-08-31 Sumitomo Chemical Company, Limited Composition de résine cyanate et laminé revêtu de cuivre utilisant cette composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3658623A (en) * 1969-07-14 1972-04-25 Bayer Ag Process for bonding non-porous materials by means of polyfunctional aromatic cyanic acid esters
DE2947112A1 (de) * 1978-11-22 1980-05-29 Mitsubishi Gas Chemical Co Vernetzbare ueberzogene platten oder boegen und hieraus gebildete schichtgebilde
JPS5863439A (ja) * 1981-10-13 1983-04-15 三菱瓦斯化学株式会社 キヤリアテ−プ用連続シ−ト
DE4125420A1 (de) * 1991-07-29 1993-02-04 Inst Polymerenchemie Erich Cor Elektrisch hochwertige bindemittel zur herstellung von basismaterial fuer leiterplatten
US5319244A (en) * 1991-12-13 1994-06-07 International Business Machines Corporation Triazine thin film adhesives
DE4224835A1 (de) * 1992-07-28 1994-02-03 Fraunhofer Ges Forschung Elektrisch hochwertiges Basismaterial für Leiterplatten
EP0612782A1 (fr) * 1993-02-23 1994-08-31 Sumitomo Chemical Company, Limited Composition de résine cyanate et laminé revêtu de cuivre utilisant cette composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 83-50129K[21], XP002003178 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5969036A (en) * 1997-06-20 1999-10-19 The Dexter Corporation Epoxy-containing die-attach compositions
US6342577B1 (en) * 1997-07-24 2002-01-29 Loctite Corporation Thermosetting resin compositions useful as underfill sealants
US6372861B1 (en) * 1999-02-09 2002-04-16 Bakelite A.G. Cyanate resin, polyepoxide and metal complex curing agent
US6632893B2 (en) 1999-05-28 2003-10-14 Henkel Loctite Corporation Composition of epoxy resin, cyanate ester, imidazole and polysulfide tougheners
WO2001081492A1 (fr) * 2000-04-19 2001-11-01 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Adhesif a base de cyanate, destine a, et en combinaison avec des revetements d'adherence, ainsi que procede de realisation de revetements d'adherence adherant a un support
CN105339407A (zh) * 2013-06-28 2016-02-17 美国圣戈班性能塑料公司 氰酸酯树脂共混物及包含它们的天线罩
WO2014210236A1 (fr) * 2013-06-28 2014-12-31 Saint-Gobain Performance Plastics Corporation Mélanges de résines de cyanate et radomes les comprenant
US9914803B2 (en) 2013-06-28 2018-03-13 Saint-Gobain Performance Plastics Corporation Cyanate resin blends and radomes including them
US10329383B2 (en) 2013-06-28 2019-06-25 Saint-Gobain Performance Plastics Corporation Cyanate resin blends and radomes including them
US9879163B2 (en) 2014-06-06 2018-01-30 General Electric Company Composition for bonding windings or core laminates in an electrical machine, and associated method
US9911521B2 (en) 2014-06-06 2018-03-06 General Electric Company Curable composition for electrical machine, and associated method
CN108264763A (zh) * 2016-12-30 2018-07-10 比亚迪股份有限公司 氰酸酯树脂原料组合物和氰酸酯树脂以及氰酸酯树脂金属复合材料和其制备方法
CN108264763B (zh) * 2016-12-30 2020-03-20 比亚迪股份有限公司 氰酸酯树脂原料组合物和氰酸酯树脂以及氰酸酯树脂金属复合材料和其制备方法

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