JP2004502859A - ポリイミドハイブリッド接着剤 - Google Patents
ポリイミドハイブリッド接着剤 Download PDFInfo
- Publication number
- JP2004502859A JP2004502859A JP2002509429A JP2002509429A JP2004502859A JP 2004502859 A JP2004502859 A JP 2004502859A JP 2002509429 A JP2002509429 A JP 2002509429A JP 2002509429 A JP2002509429 A JP 2002509429A JP 2004502859 A JP2004502859 A JP 2004502859A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy
- adhesive composition
- curing agent
- hybrid adhesive
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 83
- 239000004642 Polyimide Substances 0.000 title claims abstract description 82
- 239000000853 adhesive Substances 0.000 title claims abstract description 62
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 81
- 239000004593 Epoxy Substances 0.000 claims abstract description 54
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 28
- 229920000647 polyepoxide Polymers 0.000 claims description 53
- 239000003822 epoxy resin Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 25
- 150000008064 anhydrides Chemical group 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000011941 photocatalyst Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000004913 activation Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000011952 anionic catalyst Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229920004738 ULTEM® Polymers 0.000 description 34
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 24
- 239000000463 material Substances 0.000 description 22
- 238000011160 research Methods 0.000 description 21
- 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 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000376 reactant Substances 0.000 description 18
- -1 ether anhydride Chemical class 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000011521 glass Substances 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 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
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 239000011151 fibre-reinforced plastic Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
- 229920006332 epoxy adhesive Polymers 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 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
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 238000010128 melt processing Methods 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-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
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- NJWZAJNQKJUEKC-UHFFFAOYSA-N 4-[4-[2-[4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C=1C=C(OC=2C=3C(=O)OC(=O)C=3C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC2=C1C(=O)OC2=O NJWZAJNQKJUEKC-UHFFFAOYSA-N 0.000 description 2
- DGQOZCNCJKEVOA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1CC(=O)OC1=O DGQOZCNCJKEVOA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- 239000002313 adhesive film Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-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
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- 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 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
- XGKKWUNSNDTGDS-UHFFFAOYSA-N 2,5-dimethylheptane-1,7-diamine Chemical compound NCC(C)CCC(C)CCN XGKKWUNSNDTGDS-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-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
- 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
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-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
- XQGMTFGZVRBDPQ-UHFFFAOYSA-N 3-(4-propylphenoxy)phthalic acid Chemical compound C1=CC(CCC)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O XQGMTFGZVRBDPQ-UHFFFAOYSA-N 0.000 description 1
- HPIXFUTWHVJYBG-UHFFFAOYSA-N 3-[1-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOC(C)OCCCN HPIXFUTWHVJYBG-UHFFFAOYSA-N 0.000 description 1
- FUJGQJMITCJTFA-UHFFFAOYSA-N 3-[3-(2,3-dicarboxyphenoxy)phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)C=CC=2)=C1C(O)=O FUJGQJMITCJTFA-UHFFFAOYSA-N 0.000 description 1
- KHDSXXRHWXXXBY-UHFFFAOYSA-N 3-[4-(2,3-dicarboxyphenoxy)phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O KHDSXXRHWXXXBY-UHFFFAOYSA-N 0.000 description 1
- WQYOBFRCLOZCRC-UHFFFAOYSA-N 3-[4-[4-(2,3-dicarboxyphenoxy)benzoyl]phenoxy]phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C(=C(C(O)=O)C=CC=3)C(O)=O)=CC=2)=C1C(O)=O WQYOBFRCLOZCRC-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
- YEEIWUUBRYZFEH-UHFFFAOYSA-N 3-methoxyhexane-1,6-diamine Chemical compound NCCC(OC)CCCN YEEIWUUBRYZFEH-UHFFFAOYSA-N 0.000 description 1
- SGEWZUYVXQESSB-UHFFFAOYSA-N 3-methylheptane-1,7-diamine Chemical compound NCCC(C)CCCCN SGEWZUYVXQESSB-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- JQGUWEUKOQRRJU-UHFFFAOYSA-N 4-(4-aminobutyl-methyl-trimethylsilyloxysilyl)butan-1-amine Chemical compound NCCCC[Si](C)(O[Si](C)(C)C)CCCCN JQGUWEUKOQRRJU-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
- GQUSLIBGUTZKJZ-UHFFFAOYSA-N 4-[3-(3,4-dicarboxyphenoxy)phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 GQUSLIBGUTZKJZ-UHFFFAOYSA-N 0.000 description 1
- PEHWKKLPRVXJNU-UHFFFAOYSA-N 4-[4-benzoyl-1-(3,4-dicarboxyphenoxy)cyclohexa-2,4-dien-1-yl]oxyphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC(C(=O)C=2C=CC=CC=2)=CC1 PEHWKKLPRVXJNU-UHFFFAOYSA-N 0.000 description 1
- BBTGUNMUUYNPLH-UHFFFAOYSA-N 5-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 BBTGUNMUUYNPLH-UHFFFAOYSA-N 0.000 description 1
- ZOXBWJMCXHTKNU-UHFFFAOYSA-N 5-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C2C(=O)OC(=O)C2=C1 ZOXBWJMCXHTKNU-UHFFFAOYSA-N 0.000 description 1
- MBRGOFWKNLPACT-UHFFFAOYSA-N 5-methylnonane-1,9-diamine Chemical compound NCCCCC(C)CCCCN MBRGOFWKNLPACT-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OCROGAXNSVAYBT-UHFFFAOYSA-L C1(=CC=CC2=CC=CC=C12)[O-].[Co+2].C1(=CC=CC2=CC=CC=C12)[O-] Chemical compound C1(=CC=CC2=CC=CC=C12)[O-].[Co+2].C1(=CC=CC2=CC=CC=C12)[O-] OCROGAXNSVAYBT-UHFFFAOYSA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- OQXSSPQKPIRZFQ-UHFFFAOYSA-N NCCC(CCCCN)C.NCCCC(CCCN)(C)C Chemical compound NCCC(CCCCN)C.NCCCC(CCCN)(C)C OQXSSPQKPIRZFQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 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
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-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
- 239000003973 paint Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000012745 toughening agent 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/611,450 US6294259B1 (en) | 2000-07-06 | 2000-07-06 | Polyimide hybrid adhesives |
| PCT/US2000/030829 WO2002004572A1 (en) | 2000-07-06 | 2000-11-10 | Polyimide hybrid adhesives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004502859A true JP2004502859A (ja) | 2004-01-29 |
| JP2004502859A5 JP2004502859A5 (enExample) | 2007-12-13 |
Family
ID=24449066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002509429A Withdrawn JP2004502859A (ja) | 2000-07-06 | 2000-11-10 | ポリイミドハイブリッド接着剤 |
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 (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2006307091A (ja) * | 2005-04-28 | 2006-11-09 | Kaneka Corp | 活性エステル化合物およびその利用 |
| WO2018139559A1 (ja) * | 2017-01-27 | 2018-08-02 | 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、フレキシブル銅張積層板、及び、回路基板 |
| 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 |
| JP2018203991A (ja) * | 2017-05-31 | 2018-12-27 | 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 |
| JP2018203992A (ja) * | 2017-05-31 | 2018-12-27 | 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 |
| JP2019056102A (ja) * | 2017-05-31 | 2019-04-11 | 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 |
| CN109642027A (zh) * | 2017-01-27 | 2019-04-16 | 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、柔性覆铜层叠板和电路基板 |
| WO2019188436A1 (ja) | 2018-03-28 | 2019-10-03 | 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 |
| 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 |
| 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 |
| KR20200135761A (ko) * | 2018-03-20 | 2020-12-03 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 접착제, 접착 필름, 커버레이 필름 및 플렉시블 구리 피복 적층판 |
| CN114276654A (zh) * | 2021-11-24 | 2022-04-05 | 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 |
| JPWO2022138407A1 (enExample) * | 2020-12-23 | 2022-06-30 | ||
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
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| 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 |
| 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 |
| 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 |
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| 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 |
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| US5028681A (en) | 1986-12-31 | 1991-07-02 | Peters Edward N | Novel poly(imide-siloxane) block copolymers and process for their preparation |
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-
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 (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2006307091A (ja) * | 2005-04-28 | 2006-11-09 | Kaneka Corp | 活性エステル化合物およびその利用 |
| KR20190104130A (ko) * | 2017-01-27 | 2019-09-06 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 경화물, 접착제, 접착 필름, 커버레이 필름, 플렉시블 구리 피복 적층판, 및, 회로 기판 |
| WO2018139559A1 (ja) * | 2017-01-27 | 2018-08-02 | 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、フレキシブル銅張積層板、及び、回路基板 |
| US11802177B2 (en) | 2017-01-27 | 2023-10-31 | Sekisui Chemical Co., Ltd. | Curable resin composition, adhesive, imide oligomer, imide oligomer composition, and curing agent |
| KR102501343B1 (ko) * | 2017-01-27 | 2023-02-17 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 경화물, 접착제, 접착 필름, 커버레이 필름, 플렉시블 구리 피복 적층판, 및, 회로 기판 |
| US11421107B2 (en) | 2017-01-27 | 2022-08-23 | Sekisui Chemical Co., Ltd. | Curable resin composition, cured product, adhesive, bonding film, coverlay film, flexible copper-clad laminate and circuit board |
| CN109642027A (zh) * | 2017-01-27 | 2019-04-16 | 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、柔性覆铜层叠板和电路基板 |
| 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 |
| 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 |
| 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 |
| KR20200013649A (ko) | 2017-05-31 | 2020-02-07 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 경화물, 접착제, 접착 필름, 커버레이 필름, 및, 프린트 배선판 |
| JP2018203992A (ja) * | 2017-05-31 | 2018-12-27 | 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 |
| JP2019056102A (ja) * | 2017-05-31 | 2019-04-11 | 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 |
| KR102671097B1 (ko) * | 2017-05-31 | 2024-05-30 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 경화물, 접착제, 접착 필름, 커버레이 필름, 및, 프린트 배선판 |
| 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 |
| JP2018203991A (ja) * | 2017-05-31 | 2018-12-27 | 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 |
| 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 |
| KR102752119B1 (ko) * | 2018-03-20 | 2025-01-09 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 접착제, 접착 필름, 커버레이 필름 및 플렉시블 구리 피복 적층판 |
| KR20200135761A (ko) * | 2018-03-20 | 2020-12-03 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 접착제, 접착 필름, 커버레이 필름 및 플렉시블 구리 피복 적층판 |
| KR20200138165A (ko) | 2018-03-28 | 2020-12-09 | 세키스이가가쿠 고교가부시키가이샤 | 경화성 수지 조성물, 접착제, 접착 필름, 회로 기판, 층간 절연 재료, 및 프린트 배선판 |
| US12139576B2 (en) | 2018-03-28 | 2024-11-12 | Sekisui Chemical Co., Ltd. | Curable resin composition, adhesive agent, adhesive film, circuit substrate, interlayer insulating material, and printed wiring board |
| WO2019188436A1 (ja) | 2018-03-28 | 2019-10-03 | 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 |
| WO2022138407A1 (ja) * | 2020-12-23 | 2022-06-30 | 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 |
| JPWO2022138407A1 (enExample) * | 2020-12-23 | 2022-06-30 | ||
| 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 |
| CN114276654A (zh) * | 2021-11-24 | 2022-04-05 | 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 |
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 |
| TWI288773B (en) | 2007-10-21 |
| DE60011150D1 (de) | 2004-07-01 |
| DE60011150T2 (de) | 2005-06-16 |
| ATE267858T1 (de) | 2004-06-15 |
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