TWI288773B - Polyimide hybrid adhesives - Google Patents
Polyimide hybrid adhesives Download PDFInfo
- Publication number
- TWI288773B TWI288773B TW090115459A TW90115459A TWI288773B TW I288773 B TWI288773 B TW I288773B TW 090115459 A TW090115459 A TW 090115459A TW 90115459 A TW90115459 A TW 90115459A TW I288773 B TWI288773 B TW I288773B
- Authority
- TW
- Taiwan
- Prior art keywords
- epoxy
- mixture
- group
- curing agent
- binder composition
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 31
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 31
- 229920001721 polyimide Polymers 0.000 title abstract description 8
- 239000004642 Polyimide Substances 0.000 title abstract description 7
- 239000004593 Epoxy Substances 0.000 claims abstract description 56
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims description 100
- 229920000647 polyepoxide Polymers 0.000 claims description 43
- 239000003822 epoxy resin Substances 0.000 claims description 42
- 239000011230 binding agent Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000011941 photocatalyst Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 239000011952 anionic catalyst Substances 0.000 claims 2
- 239000011951 cationic catalyst Substances 0.000 claims 2
- 125000004018 acid anhydride group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 235000015097 nutrients Nutrition 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 49
- 239000011347 resin Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 33
- 238000011160 research Methods 0.000 description 32
- 229920004738 ULTEM® Polymers 0.000 description 29
- 238000001723 curing Methods 0.000 description 21
- 239000000126 substance Substances 0.000 description 18
- -1 ether anhydrides Chemical class 0.000 description 17
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 15
- 150000008064 anhydrides Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- 239000012780 transparent material Substances 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000011151 fibre-reinforced plastic Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000010128 melt processing Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 2
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 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
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002312 polyamide-imide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000004060 quinone imines Chemical class 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- SEOSQKLNXIGNSV-UHFFFAOYSA-N 1-aminopropane-2,2-dithiol Chemical compound CC(S)(S)CN SEOSQKLNXIGNSV-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- BUGIFNPYQVKODR-UHFFFAOYSA-N 2-methylhexane-1,6-diamine Chemical compound NCC(C)CCCCN BUGIFNPYQVKODR-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QPIOXOJERGNNMX-UHFFFAOYSA-N 3-(3-aminopropylsulfanyl)propan-1-amine Chemical compound NCCCSCCCN QPIOXOJERGNNMX-UHFFFAOYSA-N 0.000 description 1
- PDEDMAOWFXYLBB-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,3,5,6-tetramethyl-1,4-dioxan-2-yl]propan-1-amine Chemical compound NCCCC1(C(OC(C(O1)C)C)(C)CCCN)C PDEDMAOWFXYLBB-UHFFFAOYSA-N 0.000 description 1
- XZWYIEAOALEANP-UHFFFAOYSA-N 3-[4-[2-[4-(2,3-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O XZWYIEAOALEANP-UHFFFAOYSA-N 0.000 description 1
- BUIUJLKLPHVOAM-UHFFFAOYSA-N 3-[[7a-(2,3-dicarboxyphenoxy)-1,3-dioxo-3aH-2-benzofuran-4-yl]oxy]phthalic acid Chemical compound C(=O)(O)C1=C(OC23C(=O)OC(C2C(=CC=C3)OC2=C(C(=CC=C2)C(=O)O)C(=O)O)=O)C=CC=C1C(=O)O BUIUJLKLPHVOAM-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- YEEIWUUBRYZFEH-UHFFFAOYSA-N 3-methoxyhexane-1,6-diamine Chemical compound NCCC(OC)CCCN YEEIWUUBRYZFEH-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
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- KJLPSBMDOIVXSN-UHFFFAOYSA-N 4-[4-[2-[4-(3,4-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 KJLPSBMDOIVXSN-UHFFFAOYSA-N 0.000 description 1
- MRTAEHMRKDVKMS-UHFFFAOYSA-N 4-[4-[4-(3,4-dicarboxyphenoxy)phenyl]sulfanylphenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 MRTAEHMRKDVKMS-UHFFFAOYSA-N 0.000 description 1
- MQJUIYIQEUTKRS-UHFFFAOYSA-N 4-[[7a-(3,4-dicarboxyphenoxy)-1,3-dioxo-3aH-2-benzofuran-4-yl]oxy]phthalic acid Chemical compound C(=O)(O)C=1C=C(C=CC=1C(=O)O)OC12C(=O)OC(C1C(=CC=C2)OC1=CC(=C(C=C1)C(=O)O)C(=O)O)=O MQJUIYIQEUTKRS-UHFFFAOYSA-N 0.000 description 1
- LLQZYWNVPSWWIK-UHFFFAOYSA-N 4-[[7a-(3,4-dicarboxyphenoxy)-1,3-dioxo-3aH-2-benzofuran-5-yl]oxy]phthalic acid Chemical compound C(=O)(O)C=1C=C(C=CC=1C(=O)O)OC12C(=O)OC(C1C=C(C=C2)OC1=CC(=C(C=C1)C(=O)O)C(=O)O)=O LLQZYWNVPSWWIK-UHFFFAOYSA-N 0.000 description 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- IYHRSVWVKBRFHS-UHFFFAOYSA-N CCCC(C)(C)CCCC(N)N Chemical compound CCCC(C)(C)CCCC(N)N IYHRSVWVKBRFHS-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VVWYWLMUOQBEKL-UHFFFAOYSA-N FC=1C(=C(C(=C(C1)F)F)F)F.NN Chemical compound FC=1C(=C(C(=C(C1)F)F)F)F.NN VVWYWLMUOQBEKL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LWZXVXBKJLPXPF-UHFFFAOYSA-N N,N-bis(3-aminopropyl)thiohydroxylamine Chemical compound SN(CCCN)CCCN LWZXVXBKJLPXPF-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- YOSWQBTXYJJTHV-UHFFFAOYSA-N [amino(phenyl)phosphanyl]benzene Chemical compound C=1C=CC=CC=1P(N)C1=CC=CC=C1 YOSWQBTXYJJTHV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- SCNCIXKLOBXDQB-UHFFFAOYSA-K cobalt(3+);2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Co+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O SCNCIXKLOBXDQB-UHFFFAOYSA-K 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- ZUGPRXZCSHTXTE-UHFFFAOYSA-N diphenyl sulfate Chemical compound C=1C=CC=CC=1OS(=O)(=O)OC1=CC=CC=C1 ZUGPRXZCSHTXTE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
Classifications
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
-
- 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
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of 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 C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- C09J179/00—Adhesives 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 C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/611,450 US6294259B1 (en) | 2000-07-06 | 2000-07-06 | Polyimide hybrid adhesives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI288773B true TWI288773B (en) | 2007-10-21 |
Family
ID=24449066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090115459A TWI288773B (en) | 2000-07-06 | 2001-06-26 | Polyimide hybrid adhesives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6294259B1 (enExample) |
| EP (1) | EP1303571B1 (enExample) |
| JP (1) | JP2004502859A (enExample) |
| KR (1) | KR100676331B1 (enExample) |
| AT (1) | ATE267858T1 (enExample) |
| AU (1) | AU2001217593A1 (enExample) |
| DE (1) | DE60011150T2 (enExample) |
| TW (1) | TWI288773B (enExample) |
| WO (1) | WO2002004572A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108865047A (zh) * | 2018-06-12 | 2018-11-23 | 山东科思姆特种材料技术开发有限公司 | 耐高温抗辐射胶黏剂及其制备方法 |
| TWI823848B (zh) * | 2017-01-27 | 2023-12-01 | 日商積水化學工業股份有限公司 | 硬化性樹脂組成物、硬化物、接著劑、接著膜、覆蓋膜、可撓性覆銅積層板、及電路基板 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004109403A1 (ja) * | 2003-06-02 | 2004-12-16 | Toray Industries, Inc. | 感光性樹脂組成物およびそれを用いた電子部品ならびに表示装置 |
| WO2005100433A1 (ja) * | 2004-04-19 | 2005-10-27 | Kaneka Corporation | 熱硬化性樹脂組成物、及びそれを用いてなる積層体、回路基板 |
| US7816487B2 (en) * | 2004-09-30 | 2010-10-19 | Intel Corporation | Die-attach films for chip-scale packaging, packages made therewith, and methods of assembling same |
| US20060116476A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Hybrid thermosetting composition |
| US20060116492A1 (en) * | 2004-12-01 | 2006-06-01 | 3M Innovative Properties Company | Branched polymer |
| JP5014587B2 (ja) * | 2005-04-28 | 2012-08-29 | 株式会社カネカ | 活性エステル化合物およびその利用 |
| TWI416671B (zh) * | 2005-05-31 | 2013-11-21 | 住友電木股份有限公司 | A pre-coated encapsulated resin composition, a semiconductor device using the same, and a method for manufacturing the same |
| SG177608A1 (en) * | 2009-07-10 | 2012-02-28 | Toray Industries | Adhesive composition, adhesive sheet, circuit board and semiconductor device both produced using these, and processes for producing these |
| CN109415509A (zh) * | 2017-01-27 | 2019-03-01 | 积水化学工业株式会社 | 固化性树脂组合物、粘接剂、酰亚胺低聚物、酰亚胺低聚物组合物以及固化剂 |
| JP7207863B2 (ja) * | 2017-05-31 | 2023-01-18 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム |
| WO2018221217A1 (ja) * | 2017-05-31 | 2018-12-06 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、接着フィルム、カバーレイフィルム、及び、プリント配線板 |
| JP7144182B2 (ja) * | 2017-05-31 | 2022-09-29 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム |
| JP7211715B2 (ja) * | 2017-05-31 | 2023-01-24 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、接着フィルム、カバーレイフィルム、及び、プリント配線板 |
| CN110691805A (zh) * | 2017-05-31 | 2020-01-14 | 积水化学工业株式会社 | 固化性树脂组合物、固化物、粘接剂、粘接膜、覆盖层膜和印制电路布线板 |
| TWI770178B (zh) * | 2017-05-31 | 2022-07-11 | 日商積水化學工業股份有限公司 | 硬化性樹脂組成物、硬化物、接著劑、接著膜、覆蓋膜及印刷配線板 |
| CN111263782A (zh) * | 2017-10-27 | 2020-06-09 | 积水化学工业株式会社 | 固化性树脂组合物、固化物、粘接剂和粘接膜 |
| CN111417683B (zh) * | 2018-03-20 | 2023-07-25 | 积水化学工业株式会社 | 固化性树脂组合物、粘接剂、粘接膜、覆盖膜及柔性覆铜层叠板 |
| JP7018942B2 (ja) | 2018-03-28 | 2022-02-14 | 積水化学工業株式会社 | 硬化性樹脂組成物、接着剤、接着フィルム、回路基板、層間絶縁材料、及び、プリント配線板 |
| TW202233794A (zh) * | 2020-12-23 | 2022-09-01 | 日商積水化學工業股份有限公司 | 硬化性樹脂組成物、硬化物、接著劑、及接著膜 |
| CN114276654B (zh) * | 2021-11-24 | 2023-10-17 | 久耀电子科技（江苏）有限公司 | 一种树脂组合物、半固化片以及高cti覆铜板 |
| CN115536816B (zh) * | 2022-10-28 | 2024-02-20 | 中国科学院兰州化学物理研究所 | 一种热固性环氧树脂形状记忆聚合物及其制备方法 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217389A (en) | 1969-05-08 | 1980-08-12 | General Electric Company | Curable mixture of water soluble polyester and polyimide precursor, process of coating and products |
| FR2094607A5 (enExample) | 1970-06-26 | 1972-02-04 | Rhone Poulenc Sa | |
| US3989670A (en) | 1972-12-29 | 1976-11-02 | General Electric Company | Method for making polyetherimides |
| GB1422396A (en) | 1973-01-26 | 1976-01-28 | Ciba Geigy Ag | Film adhesives |
| US4073773A (en) | 1976-12-30 | 1978-02-14 | General Electric Company | Melt polymerization method for making polyetherimides |
| JPS5923330B2 (ja) | 1977-11-01 | 1984-06-01 | 三菱電機株式会社 | 耐熱性エポキシ樹脂組成物 |
| JPS5815948B2 (ja) | 1979-11-28 | 1983-03-28 | 日東電工株式会社 | 回路基板用絶縁材料 |
| FR2514772B1 (fr) | 1981-10-19 | 1985-09-06 | Inst Francais Du Petrole | Compositions reactives de polyimides thermostables presentant une solubilite elevee et leurs utilisations |
| US4416973A (en) | 1982-01-04 | 1983-11-22 | E. I. Du Pont De Nemours & Co. | Radiation-sensitive polyimide precursor composition derived from a diaryl fluoro compound |
| JPS58223149A (ja) | 1982-06-22 | 1983-12-24 | Toray Ind Inc | 感光性ポリイミド用現像液 |
| US4410664A (en) | 1982-09-20 | 1983-10-18 | Plastics Engineering Company | Polyimide-epoxy thermoset resins |
| US4443592A (en) | 1983-01-21 | 1984-04-17 | General Electric Company | Method for making polyetherimide |
| US4443591A (en) | 1983-01-21 | 1984-04-17 | General Electric Company | Method for making polyetherimide |
| US4604230A (en) | 1984-10-15 | 1986-08-05 | Stauffer Chemical Company | Thermally stable adhesive |
| US4585852A (en) | 1984-11-20 | 1986-04-29 | General Electric Company | Two-step process for producing polyetherimides |
| JPS61270852A (ja) | 1985-05-24 | 1986-12-01 | Nitto Electric Ind Co Ltd | 半導体装置 |
| US4769476A (en) | 1985-09-27 | 1988-09-06 | General Electric Company | Bis(dialkyl aromatic ether anhydride) and polymers obtained therefrom |
| US4611048A (en) | 1985-10-04 | 1986-09-09 | General Electric Company | Hydroxy terminated polyetherimide oligomers |
| US4996268A (en) | 1986-07-01 | 1991-02-26 | National Starch And Chemical Investment Holding Corporation | Carbinol-containing polyimide oligomers terminated with epoxide-reactive groups |
| US4820779A (en) | 1986-07-01 | 1989-04-11 | National Starch And Chemical Corporation | Adduct of a carbinol-containing polyimide oligomer terminated with epoxide-reactive groups and a polyepoxide |
| US4757150A (en) | 1986-07-31 | 1988-07-12 | General Electric Company | Polyetherimide bisphenol compositions |
| JPS6375034A (ja) | 1986-09-18 | 1988-04-05 | Agency Of Ind Science & Technol | 付加硬化型可溶性イミドオリゴマ及びそれを用いた繊維強化複合材料用中間素材 |
| US5028681A (en) | 1986-12-31 | 1991-07-02 | Peters Edward N | Novel poly(imide-siloxane) block copolymers and process for their preparation |
| US4835249A (en) | 1986-12-31 | 1989-05-30 | General Electric Company | Process for preparing polyimides |
| EP0309190A3 (en) | 1987-09-22 | 1990-10-17 | National Starch And Chemical Investment Holding Corporation | Polyimide coating compositions |
| JP2708191B2 (ja) | 1988-09-20 | 1998-02-04 | 株式会社日立製作所 | 半導体装置 |
| ES2069052T3 (es) | 1989-01-20 | 1995-05-01 | Ciba Geigy Ag | Mezclas reticulables de sustancias-resina epoxi que contienen un termoplastico con grupos terminales fenolicos. |
| JP2678934B2 (ja) | 1989-01-20 | 1997-11-19 | 宇部興産株式会社 | 熱硬化性樹脂組成物およびその硬化物 |
| EP0379467A3 (de) | 1989-01-20 | 1991-07-10 | Ciba-Geigy Ag | Hydroxylgruppen-endständige stickstoffhaltige Polymere |
| JP2643518B2 (ja) | 1989-02-10 | 1997-08-20 | 東レ株式会社 | プリプレグ |
| US5108825A (en) | 1989-12-21 | 1992-04-28 | General Electric Company | Epoxy/polyimide copolymer blend dielectric and layered circuits incorporating it |
| EP0441047B1 (en) | 1990-01-19 | 1996-06-05 | Minnesota Mining And Manufacturing Company | Thermosettable composition |
| US5135990A (en) | 1990-10-05 | 1992-08-04 | General Electric Company | Polyetherimide-liquid crystalline polymer blends |
| FR2674860B1 (fr) | 1991-04-04 | 1994-02-18 | Ciba Geigy | Solutions d'impregnation a base d'au moins un oligomere poly(imide-amide) thermoplastique reactif et d'un co-reactif, utilisables notamment pour la realisation d'articles intermediaires pre-impregnes. |
| US5252700A (en) | 1991-04-30 | 1993-10-12 | Mitsui Toatsu Chemicals, Inc. | Heat-resistant adhesive and method of adhesion by using adhesive |
| US5250228A (en) | 1991-11-06 | 1993-10-05 | Raychem Corporation | Conductive polymer composition |
| US5169911A (en) | 1992-02-18 | 1992-12-08 | General Electric Company | Heat curable blends of silicone polymide and epoxy resin |
| US5800575A (en) | 1992-04-06 | 1998-09-01 | Zycon Corporation | In situ method of forming a bypass capacitor element internally within a capacitive PCB |
| JPH0660230A (ja) | 1992-08-07 | 1994-03-04 | Omron Corp | 非接触パスゲートシステム |
| JP3288439B2 (ja) | 1992-08-19 | 2002-06-04 | 株式会社お茶の玉露園 | 粉茶の製造方法 |
| US5412065A (en) | 1993-04-09 | 1995-05-02 | Ciba-Geigy Corporation | Polyimide oligomers |
| US5606014A (en) | 1995-08-04 | 1997-02-25 | The United States Of America As Represented By The United States National Aeronautics And Space Administration | Imide oligomers and co-oligomers containing pendent phenylethynyl groups and polymers therefrom |
| GB9612523D0 (en) | 1996-06-14 | 1996-08-14 | Fiberite Inc | Improvements relating to resin compositions |
| US5883182A (en) | 1997-01-06 | 1999-03-16 | A Creative Research & Testing Co. | Coating compositions and coatings thereof |
-
2000
- 2000-07-06 US US09/611,450 patent/US6294259B1/en not_active Expired - Fee Related
- 2000-11-10 EP EP00980313A patent/EP1303571B1/en not_active Expired - Lifetime
- 2000-11-10 AU AU2001217593A patent/AU2001217593A1/en not_active Abandoned
- 2000-11-10 KR KR1020037000107A patent/KR100676331B1/ko not_active Expired - Fee Related
- 2000-11-10 DE DE60011150T patent/DE60011150T2/de not_active Expired - Fee Related
- 2000-11-10 AT AT00980313T patent/ATE267858T1/de not_active IP Right Cessation
- 2000-11-10 WO PCT/US2000/030829 patent/WO2002004572A1/en not_active Ceased
- 2000-11-10 JP JP2002509429A patent/JP2004502859A/ja not_active Withdrawn
-
2001
- 2001-06-26 TW TW090115459A patent/TWI288773B/zh not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI823848B (zh) * | 2017-01-27 | 2023-12-01 | 日商積水化學工業股份有限公司 | 硬化性樹脂組成物、硬化物、接著劑、接著膜、覆蓋膜、可撓性覆銅積層板、及電路基板 |
| CN108865047A (zh) * | 2018-06-12 | 2018-11-23 | 山东科思姆特种材料技术开发有限公司 | 耐高温抗辐射胶黏剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040030387A (ko) | 2004-04-09 |
| EP1303571B1 (en) | 2004-05-26 |
| WO2002004572A1 (en) | 2002-01-17 |
| US6294259B1 (en) | 2001-09-25 |
| AU2001217593A1 (en) | 2002-01-21 |
| EP1303571A1 (en) | 2003-04-23 |
| KR100676331B1 (ko) | 2007-02-05 |
| DE60011150D1 (de) | 2004-07-01 |
| DE60011150T2 (de) | 2005-06-16 |
| JP2004502859A (ja) | 2004-01-29 |
| ATE267858T1 (de) | 2004-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI288773B (en) | Polyimide hybrid adhesives | |
| TWI821171B (zh) | 硬化性樹脂組成物、接著劑、醯亞胺寡聚物、醯亞胺寡聚物組成物、及硬化劑 | |
| JP4535245B2 (ja) | 部分ブロックポリイミド−ポリシロキサン共重合体及びその製造方法並びに該共重合体を含む樹脂組成物 | |
| JP2998858B2 (ja) | 耐熱性樹脂接着剤 | |
| TWI823848B (zh) | 硬化性樹脂組成物、硬化物、接著劑、接著膜、覆蓋膜、可撓性覆銅積層板、及電路基板 | |
| JP7171365B2 (ja) | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム | |
| TWI797117B (zh) | 醯亞胺寡聚物、硬化劑、接著劑、及醯亞胺寡聚物之製造方法 | |
| WO2021193437A1 (ja) | 硬化性樹脂組成物、接着剤、及び、接着フィルム | |
| WO2021241548A1 (ja) | 硬化性樹脂組成物、接着剤、接着剤ワニス、接着フィルム、及び、硬化物 | |
| JP7168326B2 (ja) | 硬化性樹脂組成物、硬化物、接着剤、接着フィルム、及び、回路基板 | |
| WO2019181721A1 (ja) | 硬化性樹脂組成物、接着剤、接着フィルム、カバーレイフィルム、及び、フレキシブル銅張積層板 | |
| JP2023118258A (ja) | 硬化性樹脂組成物及び層間絶縁材料 | |
| WO2023032723A1 (ja) | 硬化性樹脂組成物及び層間絶縁材料 | |
| JP7207863B2 (ja) | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム | |
| JP2019127551A (ja) | 硬化性樹脂組成物、硬化物、接着剤、接着フィルム、カバーレイフィルム、フレキシブル銅張積層板、及び、回路基板 | |
| KR20230169938A (ko) | 경화성 수지 조성물, 경화물, 접착제, 및 접착 필름 | |
| JPH1171457A (ja) | ポリイミドシロキサン | |
| JP2021155493A (ja) | 熱硬化性接着フィルム | |
| WO2023136098A1 (ja) | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム | |
| JP2012241052A (ja) | 耐熱樹脂組成物及びこれを用いたアルミニウム基材 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |