JPH02247273A - Heat resistant adhesive composition - Google Patents
Heat resistant adhesive compositionInfo
- Publication number
- JPH02247273A JPH02247273A JP6846689A JP6846689A JPH02247273A JP H02247273 A JPH02247273 A JP H02247273A JP 6846689 A JP6846689 A JP 6846689A JP 6846689 A JP6846689 A JP 6846689A JP H02247273 A JPH02247273 A JP H02247273A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive composition
- tables
- formulas
- resistant adhesive
- component
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 30
- 239000000853 adhesive Substances 0.000 title claims abstract description 29
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000004962 Polyamide-imide Substances 0.000 claims abstract description 13
- 229920002312 polyamide-imide Polymers 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 9
- -1 maleimide compound Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000009719 polyimide resin Substances 0.000 description 3
- JTEZZFXJLBVVAI-UHFFFAOYSA-N 1-[3-[2-[3-(2,5-dioxopyrrol-1-yl)-2-phenoxyphenyl]propan-2-yl]-2-phenoxyphenyl]pyrrole-2,5-dione Chemical compound C=1C=CC(N2C(C=CC2=O)=O)=C(OC=2C=CC=CC=2)C=1C(C)(C)C(C=1OC=2C=CC=CC=2)=CC=CC=1N1C(=O)C=CC1=O JTEZZFXJLBVVAI-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- MMUXFMRRAYNNQW-UHFFFAOYSA-N C1(C=CC(N1C=1C(=C(C=CC=1)S(=O)(=O)C1=C(C(=CC=C1)N1C(C=CC1=O)=O)OC1=CC=CC=C1)OC1=CC=CC=C1)=O)=O Chemical compound C1(C=CC(N1C=1C(=C(C=CC=1)S(=O)(=O)C1=C(C(=CC=C1)N1C(C=CC1=O)=O)OC1=CC=CC=C1)OC1=CC=CC=C1)=O)=O MMUXFMRRAYNNQW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229920006259 thermoplastic polyimide Polymers 0.000 description 2
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- MNNRYIOVAFZDAL-UHFFFAOYSA-N 1-[2-[2-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1OC1=CC=CC=C1N1C(=O)C=CC1=O MNNRYIOVAFZDAL-UHFFFAOYSA-N 0.000 description 1
- JRGFYXSJDUIGAY-UHFFFAOYSA-N 1-[2-[2-(2,5-dioxopyrrol-1-yl)phenyl]sulfonylphenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1N1C(=O)C=CC1=O JRGFYXSJDUIGAY-UHFFFAOYSA-N 0.000 description 1
- UOHPQARQAWHBTA-UHFFFAOYSA-N 1-[2-[2-[2-(2,5-dioxopyrrol-1-yl)phenoxy]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N1C(=O)C=CC1=O UOHPQARQAWHBTA-UHFFFAOYSA-N 0.000 description 1
- BLRGXMRCGGCMQG-UHFFFAOYSA-N 1-[2-[[2-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1CC1=CC=CC=C1N1C(=O)C=CC1=O BLRGXMRCGGCMQG-UHFFFAOYSA-N 0.000 description 1
- XAZPKEBWNIUCKF-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XAZPKEBWNIUCKF-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- HHVCCCZZVQMAMT-UHFFFAOYSA-N 1-hydroxy-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(O)C(=O)C=C1C1=CC=CC=C1 HHVCCCZZVQMAMT-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- WAXBZQUSTLNLPU-UHFFFAOYSA-N 2,5-dioxo-3-phenylpyrrole-1-carboxylic acid Chemical compound O=C1N(C(=O)O)C(=O)C=C1C1=CC=CC=C1 WAXBZQUSTLNLPU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QHDSBTKCTUXBEG-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N QHDSBTKCTUXBEG-UHFFFAOYSA-N 0.000 description 1
- NQOBNHOXRSNQAH-UHFFFAOYSA-N 2-[2-[2-(2-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1N NQOBNHOXRSNQAH-UHFFFAOYSA-N 0.000 description 1
- MQZCBPWIFIEALZ-UHFFFAOYSA-N 2-[2-[2-[2-(2-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1OC1=CC=CC=C1N MQZCBPWIFIEALZ-UHFFFAOYSA-N 0.000 description 1
- GNQHLRFTGRZHLH-UHFFFAOYSA-N 2-[2-[2-[2-(2-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)N)C=1C(C)(C)C1=CC=CC=C1OC1=CC=CC=C1N GNQHLRFTGRZHLH-UHFFFAOYSA-N 0.000 description 1
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- FWWJBOQTDWLANB-UHFFFAOYSA-N C1(C=CC(N1CCC[Si](O[Si](C)(C)C)(C)CCCN1C(C=CC1=O)=O)=O)=O Chemical compound C1(C=CC(N1CCC[Si](O[Si](C)(C)C)(C)CCCN1C(C=CC1=O)=O)=O)=O FWWJBOQTDWLANB-UHFFFAOYSA-N 0.000 description 1
- 101100326920 Caenorhabditis elegans ctl-1 gene Proteins 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000004963 Torlon Substances 0.000 description 1
- 229920003997 Torlon® Polymers 0.000 description 1
- SXEHKFHPFVVDIR-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=C(NN)C=C1 SXEHKFHPFVVDIR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical class CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- RUDCBGCNXOSCTI-UHFFFAOYSA-N n-methoxy-4-[4-(methoxyamino)phenyl]aniline Chemical compound C1=CC(NOC)=CC=C1C1=CC=C(NOC)C=C1 RUDCBGCNXOSCTI-UHFFFAOYSA-N 0.000 description 1
- JGGQWILNAAODRS-UHFFFAOYSA-N n-methyl-4-[4-(methylamino)phenyl]aniline Chemical compound C1=CC(NC)=CC=C1C1=CC=C(NC)C=C1 JGGQWILNAAODRS-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical class CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Graft Or Block Polymers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は高温特性に優れた耐熱性接着剤組成物に関する
ものである。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a heat-resistant adhesive composition with excellent high-temperature properties.
接着剤組成物は近年エレクトロニクス関連分野において
飛躍的に適用範囲を拡げつつある。その主な用途はプリ
ント配線板の基板と導体回路の接着、表面実装部品の固
定、半導体チップの接着、電子部品の組み立て等であり
、今後も多様な応用展開が期待されている。しかし、こ
れらエレクトロニクス製品の多くはその製造工程や使用
条件により耐熱性、耐薬品性等優れた特性を有する接着
剤を必要とする。Adhesive compositions have been rapidly expanding their scope of application in electronics-related fields in recent years. Its main uses include bonding printed wiring board substrates and conductor circuits, fixing surface mount components, bonding semiconductor chips, and assembling electronic components, and it is expected to continue to be used in a variety of applications in the future. However, many of these electronic products require adhesives with excellent properties such as heat resistance and chemical resistance, depending on their manufacturing process and usage conditions.
これらの要求に対して多くの接着剤組成物及びその応用
製品が上布されているが、その主流であるゴム系、エポ
キシ系、アクリル系、ポリアミド系等は十分な耐熱性や
耐薬品性、特に高温時の接着強度について、求められる
特性を保持しているとは言い難い。一方、近年ポリイミ
ド系やポリベンズイミダゾール系の便れた耐熱性を有す
る接着剤が開発されているが、これらは特殊な高沸点溶
剤を含んでいるため、またその物理的性質により高温高
圧の過酷な接着条件が必要であり、用途が限定される。Many adhesive compositions and their applied products have been developed to meet these demands, but the mainstream ones, such as rubber-based, epoxy-based, acrylic-based, polyamide-based, etc., do not have sufficient heat resistance, chemical resistance, In particular, it cannot be said that the adhesive strength required at high temperatures is maintained. On the other hand, polyimide-based and polybenzimidazole-based adhesives with excellent heat resistance have been developed in recent years, but because they contain special high-boiling point solvents and because of their physical properties, Requires specific adhesion conditions, which limits its uses.
そこで、現在穏やかな条件で接着でき、且つ優れた高温
特性を有する接着剤が強く求められてし）る。この問題
を解決するために、例えば特開昭５７−１４３３２８号
公報や特開昭６１−１０８６２７号公報には、ポリアミ
ドをエポキシ樹脂Ｇこより変性して耐熱性を高めたもの
が、また特開昭６１−９５０２９号公報には、特殊な構
造を持つ熱可塑性ポリイミド樹脂を用いたものが、さら
にあるいは特開昭６２−３０１２２号公報には、２７５
°Ｃという比較的低い温度で接着可能なポリイミド樹脂
に熱硬化性のビスマレイミド化合物を添加して、高温下
の接着特性を高めたものが記載されている。しかし実際
の生産に供し得る接着条件の穏やかさ（低温、低圧、短
時間）と高耐熱性、耐薬品性を両立させるまでには至っ
ていない。Therefore, there is currently a strong demand for adhesives that can be bonded under mild conditions and have excellent high-temperature properties. In order to solve this problem, for example, JP-A-57-143328 and JP-A-61-108627 disclose polyamides modified with epoxy resin G to improve heat resistance. 61-95029 discloses a method using a thermoplastic polyimide resin having a special structure, and JP-A No. 62-30122 discloses a method using a thermoplastic polyimide resin having a special structure.
It is described that a thermosetting bismaleimide compound is added to a polyimide resin that can be bonded at a relatively low temperature of .degree. C. to improve adhesive properties at high temperatures. However, it has not yet been possible to achieve both mild bonding conditions (low temperature, low pressure, short time) and high heat resistance and chemical resistance that can be used in actual production.
本発明は、温和な条件下で接着でき、なおかつ耐熱性や
耐薬品性、特に高温下の接着強度に優れた耐熱性接着剤
組成物を提供することを目的とする。An object of the present invention is to provide a heat-resistant adhesive composition that can be bonded under mild conditions and has excellent heat resistance and chemical resistance, particularly adhesive strength at high temperatures.
すなわち、本発明は、
一般式（Ｉ）
（Ｒ１は１種又は２種以上の２価の有機基を、ｎは整数
を示す。）で示されるポリアミドイミド化合物、熱硬化
性プレポリマー、該熱硬化性プレポリマーの重合開始剤
及び溶剤の少なくとも４成分より成る耐熱性接着剤組成
物を提供するものである。That is, the present invention provides a polyamideimide compound represented by the general formula (I) (R1 represents one or more divalent organic groups, and n represents an integer), a thermosetting prepolymer, and the thermosetting prepolymer. The present invention provides a heat-resistant adhesive composition comprising at least four components: a polymerization initiator for a curable prepolymer and a solvent.
弐（１）においてＲ８が
を示し、ＹｌはＣＨｘ−、ＣＨ３ＣＨｚ−、Ｃ）＋３０
− 、Ｎ）Ｉｚ−１ＣＩ−、Ｂｒ−、Ｆ−又は水素を示
す。またｍは３０以下の整数を示す。）のうちの１種又
は２種以上の化合物が好適に用いられる。In 2 (1), R8 represents, Yl is CHx-, CH3CHz-, C)+30
-, N) Iz-1CI-, Br-, F- or hydrogen. Further, m represents an integer of 30 or less. ) are preferably used.
このポリアミドイミド化合物としては、１市されている
樹脂ｆＨＹＭＡＬＪ （日立化成工業■商品名）やｒＴ
ＯＲＬＯＮＪ （へｍｏｃｏ社商品名）の他、無水ト
リメリット酸クロライドとジアミン類から公知の方法に
よって種々のものを合成することができる。具体的には
このジアミンとして、ジアミノジフェニルエーテル、ジ
アミノジフェニルスルフィド、ジアミノジフェニルスル
ホン、ジアミノジフェニルメタン、ジメチルベンジジン
、ジアミノベンジジン、ジメトキシベンジジン、フェニ
レンジアミン、トルイレンジアミン、１．３−ビス（ア
ミノプロピル）テトラメチルジシロキサン、２．２−ビ
ス〔（アミノフェノキシ）フェニル〕プロパン、２，２
−ビス〔（アミノフェノキシ）フェニル〕へキサフルオ
ロプロパン、ビス（アミノフェノキシ）ベンゼン、ビス
〔（アミノフェノキシ）フェニル〕スルホン等を用いる
ことができる。Examples of this polyamide-imide compound include the resin fHYMALJ (trade name of Hitachi Chemical Co., Ltd.) and rT.
In addition to ORLONJ (trade name of Hemoco), various other products can be synthesized from trimellitic anhydride chloride and diamines by known methods. Specifically, the diamines include diaminodiphenyl ether, diaminodiphenyl sulfide, diaminodiphenylsulfone, diaminodiphenylmethane, dimethylbenzidine, diaminobenzidine, dimethoxybenzidine, phenylenediamine, tolylenediamine, 1,3-bis(aminopropyl)tetramethyldiamine. Siloxane, 2,2-bis[(aminophenoxy)phenyl]propane, 2,2
-Bis[(aminophenoxy)phenyl]hexafluoropropane, bis(aminophenoxy)benzene, bis[(aminophenoxy)phenyl]sulfone, etc. can be used.
また、熱硬化性プレポリマーとしては、アクリルモノマ
ー、メタクリルモノマー、マレイミド、ポリマレイミド
、フェノールノボラック、エボキ？等を用いることがで
きるが、組成物の硬化後の物性、特に電子材料として求
められる耐熱性や耐溶剤性を確保するために、
機基を示し、■は２以上の整数・を示す。）で示される
マレイミド化合物あるいはポリマレイミドが望ましい、
ここで、Ｒ７は前記Ｒ１と同様（ＸＩ、Ｙ−１をＸ２、
Ｙｌに置き換えたもの）である。In addition, thermosetting prepolymers include acrylic monomer, methacrylic monomer, maleimide, polymaleimide, phenol novolak, and epoxy. However, in order to ensure the physical properties of the composition after curing, especially the heat resistance and solvent resistance required for electronic materials, it represents a mechanical group, and ■ represents an integer of 2 or more. ) Maleimide compounds or polymaleimides are desirable.
Here, R7 is the same as R1 (XI, Y-1 is replaced by X2,
(replaced with Yl).
このマレイミド又はポリマレイミドとして具体的には、
Ｎ−フェニルマレイミド、Ｎ−シクロへキシルマレイミ
ド、Ｎ−カルボキシフェニルマレイミド、Ｎ−ヒドロキ
シフェニルマレイミド、ビス（マレイミドフェニル）エ
ーテル、ビス（マレイミドフェニル）メタン、ビス（マ
レイミドフェニル）スルフィド、ビス（マレイミドフェ
ニル）スルホン、ビス（マレイミドフェノキシフェニル
）プロパン、ビス（マレイミドフェノキシフェニル）ス
ルホン、ビス（マレイミドフェノキシフェニル）へキサ
フルオロプロパン、ビス（マレイミドフェノキシ）ベン
ゼン、ビス（マレイミドプロピル）テトラメチルジシロ
キサン、ＢＭＩ−Ｍ−２０（三井東圧化学工業■商品名
）等を用いることができるが、溶剤に対する溶解度の点
で、またマレイミド類の欠点である脆弱さを補・う点で
、特にビス（マレイミドフェノキシフェニル）プロパン
、ビス（マレイミドフェノキシフェニル）スルホンが好
ましい。Specifically, as this maleimide or polymaleimide,
N-phenylmaleimide, N-cyclohexylmaleimide, N-carboxyphenylmaleimide, N-hydroxyphenylmaleimide, bis(maleimidophenyl) ether, bis(maleimidophenyl)methane, bis(maleimidophenyl) sulfide, bis(maleimidophenyl) Sulfone, bis(maleimidophenoxyphenyl)propane, bis(maleimidophenoxyphenyl)sulfone, bis(maleimidophenoxyphenyl)hexafluoropropane, bis(maleimidophenoxy)benzene, bis(maleimidopropyl)tetramethyldisiloxane, BMI-M- 20 (trade name of Mitsui Toatsu Chemical Industry Co., Ltd.) etc. can be used, but in terms of solubility in solvents and in terms of compensating for the fragility, which is a drawback of maleimides, bis(maleimidophenoxyphenyl)propane is particularly useful. , bis(maleimidophenoxyphenyl)sulfone is preferred.
重合開始剤としては、上記の熱硬化性プレポリマーの硬
化を促進するものはすべて用いることができるが、組成
物を低温、短時間の温和な条件で硬化し得るものとして
有機過酸化物類が好ましい。As the polymerization initiator, any substance that accelerates the curing of the above-mentioned thermosetting prepolymer can be used, but organic peroxides can be used as initiators that can cure the composition under mild conditions at low temperatures and in a short period of time. preferable.
具体的には、ベンゾイルパーオキシド類、ｔ−ブチルバ
ーオキシド類、クミルパーオキシド類、ｔ−ブチルパー
オキシシクロヘキサン類、ｔ−ブチルパーオキシヘキシ
ン類等が用いられる。Specifically, benzoyl peroxides, t-butyl peroxides, cumyl peroxides, t-butylperoxycyclohexanes, t-butylperoxyhexines, etc. are used.
組成物の溶剤としては、ポリアミドイミド化合物及び熱
硬化性プレポリマーを十分に溶解し、接着温度以下の温
度域で揮発し得ることが必要であり、この要求を満たす
ものとして、メチルセロソルブやエチルセロソルブ等セ
ロソルブ系溶剤、ジメチルホルムアミド等のアミド系溶
剤、クロロホルムやトリクロロエタン等のハロゲン系溶
剤等が用いられる。The solvent for the composition needs to be able to sufficiently dissolve the polyamide-imide compound and the thermosetting prepolymer and be able to volatilize at a temperature below the bonding temperature.Methyl cellosolve and ethyl cellosolve meet this requirement. Examples of suitable solvents include cellosolve solvents, amide solvents such as dimethylformamide, and halogen solvents such as chloroform and trichloroethane.
また、この組成物成分の組成比は、ポリアミドイミド化
合物と熱硬化性プレポリマーについては、柔軟性と耐熱
、耐薬品性の両立のため、ポリアミドイミド化合物／熱
硬化性プレポリマー＝３ｏ／７０ないし９９／１（重量
部比、以下間）、特に６０／４０ないし９０／１０が望
ましい。また、熱硬化性プレポリマー／重合開始剤＝９
０／１０ないし９９．９９９１０．００１とすることが
好ましく、硬化物特性の面から、特に９９．９５１０．
０５ないし９９．９９９１０．００１が好ましい。また
、固形分の溶剤に対する割合は、組成物の粘性及び溶解
性の点から固形分／溶剤＝５／９５ないし７０／３０．
好ましＮｉｌ ５／８５ないし５ｏ１５０が適当である
。In addition, for the polyamide-imide compound and the thermosetting prepolymer, the composition ratio of the composition components is polyamide-imide compound/thermosetting prepolymer = 3o/70 to achieve both flexibility, heat resistance, and chemical resistance. A ratio of 99/1 (parts by weight, between the following), particularly 60/40 to 90/10, is desirable. In addition, thermosetting prepolymer/polymerization initiator = 9
It is preferably 0/10 to 99.99910.001, and in particular 99.9510.00 from the viewpoint of cured product properties.
05 to 99.99910.001 is preferred. In addition, the ratio of solid content to solvent is 5/95 to 70/30 from the viewpoint of viscosity and solubility of the composition.
Preferably Nil 5/85 to 5o150 is suitable.
また、これら４成分の他に必要に応じてさらに添加物を
加えることもできる。具体的には顔料、充填剤、レベリ
ング剤、カップリング剤、硬化促進助剤等が用いること
ができる。Moreover, other than these four components, further additives can be added as necessary. Specifically, pigments, fillers, leveling agents, coupling agents, curing accelerators, etc. can be used.
本発明の接着剤組成物は、ロールコータやグラビアコー
ター等を用いて、あるいは印刷法によってそれぞれ所望
の厚さに均一に塗布することができる。しかる後に溶剤
を飛散させ、プレスあるいはロールラミネーター等によ
り被着体に接着させ５る。この時、組成物中の熱硬化性
プレポリマーの三次元架橋が起こり、網目状にポリアミ
ドイミド分子鎖を包み込み、所謂ＪＰＮ構造が形成され
る。The adhesive composition of the present invention can be uniformly applied to a desired thickness using a roll coater, a gravure coater, or the like, or by a printing method. Thereafter, a solvent is scattered, and the adhesive is adhered to an adherend using a press or a roll laminator. At this time, three-dimensional crosslinking of the thermosetting prepolymer in the composition occurs, wrapping the polyamide-imide molecular chains in a network, forming a so-called JPN structure.
このようにして、温和な接着条件で、耐熱性、耐薬品性
に優れた接着層が形成できる。In this way, an adhesive layer with excellent heat resistance and chemical resistance can be formed under mild bonding conditions.
次に本発明の実施例を具体的に示すが、本発明はこれら
に限定されるものではない。なお、以下ｒＭ重量部を単
に’ ｆ！Ａ Ｊと略記する。Next, examples of the present invention will be specifically shown, but the present invention is not limited thereto. In addition, below rM weight part is simply 'f! Abbreviated as AJ.
実施例１
ポリアミドイミド樹脂ｒＨＹＭＡＬａ （日立化成側
商品名）１０部、２．２−ビス（４−（４マレイミドフ
エノキシ）フェニル〕プロパン６部、バーヘキシン２５
Ｂ（日本油脂■商品名）０．０６部、クロロホルム４０
部を混合し接着剤組成物を得た。Example 1 10 parts of polyamideimide resin rHYMALa (trade name of Hitachi Chemical), 6 parts of 2,2-bis(4-(4maleimidophenoxy)phenyl)propane, 25 parts of verhexin
B (NOF ■Product name) 0.06 part, chloroform 40
The components were mixed to obtain an adhesive composition.
これをアルミ板上に塗布し１００ ’Ｃで１０分乾燥さ
せ、銅Ｍ（厚さ３５μｍ）と重ね合わせ２００°Ｃ２０
ｋｇ／ｃ１ｉＩで１０分間プレスした。硬化物の特性を
表に示す。This was applied onto an aluminum plate, dried at 100'C for 10 minutes, and layered with copper M (35 μm thick) at 200°C.
kg/c1iI for 10 minutes. The properties of the cured product are shown in the table.
実施例２
実施例１においてプレス後、さらに２００°Ｃで３０分
間アフターキュアを行った。Example 2 After pressing in Example 1, after-curing was further performed at 200°C for 30 minutes.
実施例３
実施例１において、２，２−ビス（４−（１−マレイミ
ドフェノキシ）フェニル〕プロパンをビス（４〜マレイ
ミドフエニル）メタンに、クロロホルムをＮ、Ｎ−ジメ
チルホルムアミドに換えて、同様に接着剤組成物及び硬
化物を得た。Example 3 The same procedure as in Example 1 was carried out except that 2,2-bis(4-(1-maleimidophenoxy)phenyl)propane was replaced with bis(4-maleimidophenyl)methane and chloroform was replaced with N,N-dimethylformamide. An adhesive composition and a cured product were obtained.
実施例４
実施例１においてＨＹＭＡＬをＴＯＲＬＯＮ（Ａｍｏｃ
ｏ社商品名）に、クロロホルムをＮ Ｎ−ジメチルホ
ルムアミドに換えて同様に接着剤組成物及び硬化物を得
た。Example 4 In Example 1, HYMAL is changed to TORLON (Amoc
An adhesive composition and a cured product were obtained in the same manner as in Example 1 (trade name of Company O) except that chloroform was replaced with N N-dimethylformamide.
実施例５
ポリアミドイミド化合物として、無水トリメリット酸ク
ロライド、２，２−ビス（４−（４−アミノフェノキシ
）フェニル〕プロパン、１．３−ビス（３−アミノプロ
ピル）テトラメチルジシロキサン（モル比１０：８：２
）より公知の方法によって合成したものを１０部、２．
２−ビス〔４（４−マレイミドフェノキシ）フェニル〕
プロパン８部、バーへキシ７２５ Ｂ ０．０８部、り
０口ホルム４０部を混合し接着剤組成物を得た。これを
ポリイミドフィルム上に塗布し１００°Ｃで１０分間乾
燥し、銅箔（厚さ３５μｍ）と重ね合わせて熱ロールを
用い１８０°Ｃ−１５ｋｇ／ｃｔｌ−１ｍ／分の条件で
接着した。次いでこれを２００ ’Ｃで３０分間アフタ
ーキュアを行った。Example 5 As a polyamideimide compound, trimellitic anhydride chloride, 2,2-bis(4-(4-aminophenoxy)phenyl]propane, 1,3-bis(3-aminopropyl)tetramethyldisiloxane (molar ratio 10:8:2
), 10 parts of which were synthesized by a known method; 2.
2-bis[4(4-maleimidophenoxy)phenyl]
An adhesive composition was obtained by mixing 8 parts of propane, 0.08 parts of Verhexy 725 B, and 40 parts of RI0-form. This was applied onto a polyimide film, dried at 100°C for 10 minutes, overlapped with copper foil (thickness 35 μm), and bonded using a hot roll at 180°C and 15 kg/ctl-1 m/min. This was then subjected to after-cure at 200'C for 30 minutes.
部、クロロホルム４０部を混合し実施例１と同条件で塗
布、接着した。and 40 parts of chloroform were mixed together and coated and bonded under the same conditions as in Example 1.
比較例２
実施例Ｉにおいて、２．２−ビス〔４−（４〜マレイミ
ドフエノキシ）フェニル〕プロパンを０゜５部、パーヘ
キシン２５Ｂを０．００５部用いて同様に塗布、接着を
行った。Comparative Example 2 Coating and adhesion were performed in the same manner as in Example I using 0.5 parts of 2.2-bis[4-(4-maleimidophenoxy)phenyl]propane and 0.005 parts of Perhexine 25B. .
（以下余白）
比較例Ｉ
ＨＹＭＡＬ １０部、ビスフェノールＡ型エポキシ樹脂
（エポキシ当量１９０）６部、エポキシ樹脂硬化剤２Ｅ
４ＭＺ （四国化成■商品名） ０．１２〔発明の効果
〕
本発明の接着剤組成物は従来の高温用接着剤と比較して
非常に温和な条件下で接着でき、なお且つ接着硬化物は
優れた耐熱性、耐溶剤性を保持している。そのため要求
特性の厳しいエレクトロニクス関連分野において広（適
用するとかできる。(Left below) Comparative Example I 10 parts of HYMAL, 6 parts of bisphenol A type epoxy resin (epoxy equivalent: 190), epoxy resin curing agent 2E
4MZ (Brand name of Shikoku Kasei) 0.12 [Effects of the invention] The adhesive composition of the present invention can be bonded under very mild conditions compared to conventional high-temperature adhesives, and the adhesive cured product is It maintains excellent heat resistance and solvent resistance. Therefore, it can be widely applied in electronics-related fields with strict required characteristics.
特にプリント配線板の基材と回路間の接着や半導体チッ
プの実装部品への接着等に有効である。It is particularly effective for adhesion between the base material of a printed wiring board and a circuit, and for adhesion of a semiconductor chip to a mounted component.
手続 補正 書（自発） 平成 １年９月 ７日procedure correction calligraphy (spontaneous) September 7, 1999
Claims (1)
数を示す。）で示されるポリアミドイミド化合物、熱硬
化性プレポリマー、該熱硬化性プレポリマーの重合開始
剤及び溶剤の少なくとも４成分より成る耐熱性接着剤組
成物。 ２、式（ I ）においてＲ＿１が ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼ 及び ▲数式、化学式、表等があります▼ （Ｘ＿１は−ＣＨ＿２−、−Ｏ−、−Ｓ−、−ＳＯ＿２
−、▲数式、化学式、表等があります▼、▲数式、化学
式、表等があります▼ を示し、Ｙ＿１はＣＨ＿３−、ＣＨ＿３Ｃｒ＿２−、Ｃ
Ｈ＿３Ｏ−、ＮＨ＿２−、Ｃｌ−、Ｂｒ−、Ｆ−又は水
素を示す。またｍは３０以下の整数を示す。） のうちの１種又は２種以上である請求項１の耐熱性接着
剤組成物。 ３、熱硬化性プレポリマーが式（II） ▲数式、化学式、表等があります▼（II） （Ｒ＿２は１種又は２種以上の１価又は２価以上の有機
基を示し、１は２以上の整数を示す。 ）で示されるマレイミド化合物である請求項１記載の耐
熱性接着剤組成物。 ４、式（II）において１＝２でＲ＿２が ▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼ 及び ▲数式、化学式、表等があります▼ （Ｘ＿２は−ＣＨ＿２−、−Ｏ−、−Ｓ−、−ＳＯ＿２
−、▲数式、化学式、表等があります▼、▲数式、化学
式、表等があります▼ を示し、Ｙ＿２はＣＨ＿３−、ＣＨ＿３ＣＨ＿２−、Ｃ
Ｈ＿３Ｏ−、ＮＨ＿２−、Ｃｌ−、Ｂｒ−、Ｆ−又は水
素を示す）のうちの１種又は２種以上である請求項３記
載の耐熱性接着剤組成物。 ５、重合開始剤が有機過酸化物である請求項１記載の耐
熱性接着剤組成物。 ６、組成物の組成比（重量部比）がポリアミドイミド化
合物／熱硬化性プレポリマー＝３０／７０ないし９９／
１で且つ熱硬化性プレポリマー／重合開始剤＝９０／１
０ないし９９．９９９／０．００１で且つポリアミドイ
ミド化合物＋熱硬化性プレポリマー＋重合開始剤／溶剤
＝５／９５ないし７０／３０である請求項１記載の耐熱
性接着剤組成物。[Claims] 1. The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (R_1 represents one or more divalent organic groups, and n represents an integer. A heat-resistant adhesive composition comprising at least four components: a polyamide-imide compound represented by the following formula, a thermosetting prepolymer, a polymerization initiator for the thermosetting prepolymer, and a solvent. 2. In formula (I), R_1 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (X_1 is -CH_2-, -O -, -S-, -SO_2
-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and Y_1 is CH_3-, CH_3Cr_2-, C
Indicates H_3O-, NH_2-, Cl-, Br-, F- or hydrogen. Further, m represents an integer of 30 or less. ) The heat-resistant adhesive composition according to claim 1, wherein the heat-resistant adhesive composition is one or more of the following. 3. The thermosetting prepolymer has the formula (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (R_2 represents one or more monovalent or divalent or more organic groups, and 1 is 2 The heat-resistant adhesive composition according to claim 1, which is a maleimide compound represented by the following integer. 4. In formula (II), 1 = 2 and R_2 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ and ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (X_2 is -CH_2 -, -O-, -S-, -SO_2
-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and Y_2 is CH_3-, CH_3CH_2-, C
The heat-resistant adhesive composition according to claim 3, wherein the adhesive composition is one or more of the following: H_3O-, NH_2-, Cl-, Br-, F-, or hydrogen. 5. The heat-resistant adhesive composition according to claim 1, wherein the polymerization initiator is an organic peroxide. 6. The composition ratio (parts by weight) of polyamideimide compound/thermosetting prepolymer = 30/70 to 99/
1 and thermosetting prepolymer/polymerization initiator = 90/1
2. The heat-resistant adhesive composition according to claim 1, wherein the ratio is 0 to 99.999/0.001, and the polyamide-imide compound+thermosetting prepolymer+polymerization initiator/solvent=5/95 to 70/30.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1068466A JP2718156B2 (en) | 1989-03-20 | 1989-03-20 | Heat resistant adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1068466A JP2718156B2 (en) | 1989-03-20 | 1989-03-20 | Heat resistant adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02247273A true JPH02247273A (en) | 1990-10-03 |
| JP2718156B2 JP2718156B2 (en) | 1998-02-25 |
Family
ID=13374492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1068466A Expired - Lifetime JP2718156B2 (en) | 1989-03-20 | 1989-03-20 | Heat resistant adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2718156B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0969061A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Underfill encapsulants prepared from allylated amide compounds |
| EP0969063A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Package encapsulant compositions for use in electronic devices |
| EP0969066A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Package encapsulants prepared from allyated amide compounds |
| EP0969059A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Compositions for use in the fabrication of circuit components and printed wire boards |
| EP0969062A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Method of making electronic components using reworkable adhesives |
| EP0969064A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Method of making an electronic component using reworkable underfill encapsulants |
| EP0969065A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Die attach adhesives for use in microelectronic |
| EP0969060A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Underfill encapsulant compositions for use in electronic devices |
| JP2002161261A (en) * | 2000-11-28 | 2002-06-04 | Hitachi Chem Co Ltd | Thermosetting heat-resistant adhesive film |
| EP1453087A1 (en) * | 1994-09-02 | 2004-09-01 | Henkel Corporation | Microelectronic assembly |
-
1989
- 1989-03-20 JP JP1068466A patent/JP2718156B2/en not_active Expired - Lifetime
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1453087A1 (en) * | 1994-09-02 | 2004-09-01 | Henkel Corporation | Microelectronic assembly |
| EP0969060A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Underfill encapsulant compositions for use in electronic devices |
| EP0969062A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Method of making electronic components using reworkable adhesives |
| EP0969059A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Compositions for use in the fabrication of circuit components and printed wire boards |
| EP0969062A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Method of making electronic components using reworkable adhesives |
| EP0969059A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Compositions for use in the fabrication of circuit components and printed wire boards |
| EP0969064A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Method of making an electronic component using reworkable underfill encapsulants |
| EP0969066A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Package encapsulants prepared from allyated amide compounds |
| EP0969061A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Underfill encapsulants prepared from allylated amide compounds |
| EP0969065A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Die attach adhesives for use in microelectronic |
| EP0969066A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Package encapsulants prepared from allyated amide compounds |
| EP0969061A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Underfill encapsulants prepared from allylated amide compounds |
| EP0969063A3 (en) * | 1998-07-02 | 2000-02-23 | National Starch and Chemical Investment Holding Corporation | Package encapsulant compositions for use in electronic devices |
| EP0969063A2 (en) * | 1998-07-02 | 2000-01-05 | National Starch and Chemical Investment Holding Corporation | Package encapsulant compositions for use in electronic devices |
| JP2002161261A (en) * | 2000-11-28 | 2002-06-04 | Hitachi Chem Co Ltd | Thermosetting heat-resistant adhesive film |
| JP4671083B2 (en) * | 2000-11-28 | 2011-04-13 | 日立化成工業株式会社 | Thermosetting heat resistant adhesive film |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2718156B2 (en) | 1998-02-25 |
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