JP2022065400A - ポリイミド樹脂組成物、接着剤組成物、フィルム状接着材、接着シート、樹脂付銅箔、銅張積層板、プリント配線板及びポリイミドフィルム - Google Patents
ポリイミド樹脂組成物、接着剤組成物、フィルム状接着材、接着シート、樹脂付銅箔、銅張積層板、プリント配線板及びポリイミドフィルム Download PDFInfo
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- JP2022065400A JP2022065400A JP2020173971A JP2020173971A JP2022065400A JP 2022065400 A JP2022065400 A JP 2022065400A JP 2020173971 A JP2020173971 A JP 2020173971A JP 2020173971 A JP2020173971 A JP 2020173971A JP 2022065400 A JP2022065400 A JP 2022065400A
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- Prior art keywords
- polyimide resin
- adhesive
- resin composition
- film
- 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.)
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 95
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 69
- 239000000853 adhesive Substances 0.000 title claims description 83
- 230000001070 adhesive effect Effects 0.000 title claims description 82
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 40
- 239000011889 copper foil Substances 0.000 title claims description 38
- 229920005989 resin Polymers 0.000 title claims description 19
- 239000011347 resin Substances 0.000 title claims description 19
- 239000000463 material Substances 0.000 title description 5
- 229910052802 copper Inorganic materials 0.000 title description 2
- 239000010949 copper Substances 0.000 title description 2
- -1 aromatic tetracarboxylic anhydride Chemical class 0.000 claims abstract description 78
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 150000004985 diamines Chemical class 0.000 claims abstract description 16
- 239000004642 Polyimide Substances 0.000 claims abstract description 12
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 19
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 150000004984 aromatic diamines Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 abstract description 17
- 229910000679 solder Inorganic materials 0.000 abstract description 13
- 239000000539 dimer Substances 0.000 abstract description 10
- 238000001035 drying Methods 0.000 abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 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 31
- 150000002118 epoxides Chemical class 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 25
- 238000000034 method Methods 0.000 description 20
- 239000010410 layer Substances 0.000 description 17
- 239000012790 adhesive layer Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 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 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000007809 chemical reaction catalyst Substances 0.000 description 7
- 239000004643 cyanate ester Substances 0.000 description 7
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000000996 additive effect Effects 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- 150000005130 benzoxazines Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920005575 poly(amic acid) Polymers 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 3
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
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- 238000004381 surface treatment Methods 0.000 description 3
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- PAHZZOIHRHCHTH-UHFFFAOYSA-N 3-[2-(2,3-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)(C)C1=CC=CC(C(O)=O)=C1C(O)=O PAHZZOIHRHCHTH-UHFFFAOYSA-N 0.000 description 2
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 2
- AVCOFPOLGHKJQB-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)sulfonylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 AVCOFPOLGHKJQB-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
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-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
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 2
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- 239000007844 bleaching agent Substances 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000006258 conductive agent Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 150000001913 cyanates Chemical class 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
(B)成分はいずれも窒素原子を含まず、かつ、共沸点が70~120℃であるポリイミド樹脂組成物。
2,2’-ジアミノビフェニル、3,3’-ジアミノビフェニル、4,4’-ジアミノビフェニル、2,2’-ジメチル-4,4’-ジアミノビフェニル、2,2’-ジエチル-4,4’-ジアミノビフェニル、2,2’-ジn-プロピル-4,4’-ジアミノビフェニル等のジアミノビフェニル;
2,2-ビス[4-(3-アミノフェノキシ)フェニル]プロパン、2,2-ビス[4-(4-アミノフェノキシ)フェニル]プロパン等のビスアミノフェノキシフェニルプロパン;
3,3’-ジアミノジフェニルエーテル、3,4’-ジアミノジフェニルエーテル、4,4’-ジアミノジフェニルエーテル等のジアミノジフェニルエーテル;
p-フェニレンジアミン、m-フェニレンジアミン等のフェニレンジアミン;
3,3’-ジアミノジフェニルスルフィド、3,4’-ジアミノジフェニルスルフィド、4,4’-ジアミノジフェニルスルフィド等のジアミノジフェニルスルフィド;
3,3’-ジアミノジフェニルスルホン、3,4’-ジアミノジフェニルスルホン、4,4’-ジアミノジフェニルスルホン等のジアミノジフェニルスルホン;
3,3’-ジアミノベンゾフェノン、3,4’-ジアミノベンゾフェノン、4,4’-ジアミノベンゾフェノン等のジアミノベンゾフェノン;
3,3’-ジアミノジフェニルメタン、3,4’-ジアミノジフェニルメタン、4,4’-ジアミノジフェニルメタン、ビス[4-(3-アミノフェノキシ)フェニル]メタン等のジアミノジフェニルメタン;
2,2-ジ(3-アミノフェニル)プロパン、2,2-ジ(4-アミノフェニル)プロパン、2-(3-アミノフェニル)-2-(4-アミノフェニル)プロパン等のジアミノフェニルプロパン;
2,2-ジ(3-アミノフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパン、2,2-ジ(4-アミノフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパン、2-(3-アミノフェニル)-2-(4-アミノフェニル)-1,1,1,3,3,3-ヘキサフルオロプロパン等のジアミノフェニルヘキサフルオロプロパン;
1,1-ジ(3-アミノフェニル)-1-フェニルエタン、1,1-ジ(4-アミノフェニル)-1-フェニルエタン、1-(3-アミノフェニル)-1-(4-アミノフェニル)-1-フェニルエタン等のジアミノフェニルフェニルエタン;
1,3-ビス(3-アミノフェノキシ)ベンゼン、1,3-ビス(4-アミノフェノキシ)ベンゼン、1,4-ビス(3-アミノフェノキシ)ベンゼン、1,4-ビス(4-アミノフェノキシ)ベンゼン等のビスアミノフェノキシベンゼン;
1,3-ビス(3-アミノベンゾイル)ベンゼン、1,3-ビス(4-アミノベンゾイル)ベンゼン、1,4-ビス(3-アミノベンゾイル)ベンゼン、1,4-ビス(4-アミノベンゾイル)ベンゼン等のビスアミノベンゾイルベンゼン;
1,3-ビス(3-アミノ-α,α-ジメチルベンジル)ベンゼン、1,3-ビス(4-アミノ-α,α-ジメチルベンジル)ベンゼン、1,4-ビス(3-アミノ-α,α-ジメチルベンジル)ベンゼン、1,4-ビス(4-アミノ-α,α-ジメチルベンジル)ベンゼン等のビスアミノジメチルベンジルベンゼン;
1,3-ビス(3-アミノ-α,α-ジトリフルオロメチルベンジル)ベンゼン、1,3-ビス(4-アミノ-α,α-ジトリフルオロメチルベンジル)ベンゼン、1,4-ビス(3-アミノ-α,α-ジトリフルオロメチルベンジル)ベンゼン、1,4-ビス(4-アミノ-α,α-ジトリフルオロメチルベンジル)ベンゼン等のビスアミノジトリフルオロメチルベンジルベンゼン;
2,6-ビス(3-アミノフェノキシ)ベンゾニトリル、4,4’-ビス(3-アミノフェノキシ)ビフェニル、4,4’-ビス(4-アミノフェノキシ)ビフェニル、ビス[1-(3-アミノフェノキシ)]ビフェニル等のアミノフェノキシビフェニル;
ビス[4-(3-アミノフェノキシ)フェニル]ケトン、ビス[4-(4-アミノフェノキシ)フェニル]ケトン等のアミノフェノキシフェニルケトン;
ビス[4-(3-アミノフェノキシ)フェニル]スルフィド、ビス[4-(4-アミノフェノキシ)フェニル]スルフィド等のアミノフェノキシフェニルスルフィド;
ビス[4-(3-アミノフェノキシ)フェニル]スルホン、ビス[4-(4-アミノフェノキシ)フェニル]スルホン等のアミノフェノキシフェニルスルホン;
ビス[4-(3-アミノフェノキシ)フェニル]エーテル、ビス[4-(4-アミノフェノキシ)フェニル]エーテル等のアミノフェノキシフェニルエーテル;
2,2-ビス[4-(3-アミノフェノキシ)フェニル]プロパン、2,2-ビス[3-(3-アミノフェノキシ)フェニル]-1,1,1,3,3,3-ヘキサフルオロプロパン、2,2-ビス[4-(4-アミノフェノキシ)フェニル]-1,1,1,3,3,3-ヘキサフルオロプロパン等のアミノフェノキシフェニルプロパン;
1,3-ビス[4-(3-アミノフェノキシ)ベンゾイル]ベンゼン、1,3-ビス[4-(4-アミノフェノキシ)ベンゾイル]ベンゼン、1,4-ビス[4-(3-アミノフェノキシ)ベンゾイル]ベンゼン、1,4-ビス[4-(4-アミノフェノキシ)ベンゾイル]ベンゼン等のビス(アミノフェノキシベンゾイル)ベンゼン;
1,3-ビス[4-(3-アミノフェノキシ)-α,α-ジメチルベンジル]ベンゼン、1,3-ビス[4-(4-アミノフェノキシ)-α,α-ジメチルベンジル]ベンゼン、1,4-ビス[4-(3-アミノフェノキシ)-α,α-ジメチルベンジル]ベンゼン、1,4-ビス[4-(4-アミノフェノキシ)-α,α-ジメチルベンジル]ベンゼン等のビス(アミノフェノキシ-α,α-ジメチルベンジル)ベンゼン;
4,4’-ビス[4-(4-アミノフェノキシ)ベンゾイル]ジフェニルエーテル等のビス[(アミノアリールオキシ)ベンゾイル]ジフェニルエーテル;
4,4’-ビス[4-(4-アミノ-α,α-ジメチルベンジル)フェノキシ]ベンゾフェノン等のビス(アミノ-α,α-ジメチルベンジルフェノキシ)ベンゾフェノン:
4,4’-ビス[4-(4-アミノ-α,α-ジメチルベンジル)フェノキシ]ジフェニルスルホン等のビス[アミノ-α,α-ジメチルベンジルフェノキシ]ジフェニルスルホン;
4,4’-ビス[4-(4-アミノフェノキシ)フェノキシ]ジフェニルスルホン等のビス[アミノフェノキシフェノキシ]ジフェニルスルホン;
3,3’-ジアミノ-4,4’-ジフェノキシベンゾフェノン、3,3’-ジアミノ-4,4’-ジビフェノキシベンゾフェノン等のジアミノジアリールオキシベンゾフェノン;
3,3’-ジアミノ-4-フェノキシベンゾフェノン、3,3’-ジアミノ-4-ビフェノキシベンゾフェノン等のジアミノアリールオキシベンゾフェノン;
1-(4-アミノフェニル)-2,3-ジヒドロ-1,3,3-トリメチル-1H-インデン-5-アミン等が挙げられる。
(A)成分のイミド閉環率が前記範囲であることにより、(A)成分は、ハードセグメント及びソフトセグメントの構造が形成されやすくなり、軟化点及び柔軟性が共に高くなるためと推定される。ここで「イミド閉環率」とは、(A)成分のポリイミド樹脂における環状イミド結合の含有量を意味し、例えばNMRやIR分析等の各種分光手段により決定できる。
本発明の接着剤組成物は、本発明のポリイミド樹脂組成物及び架橋剤を含むものである。
は、前記ポリイミドとの相溶性が良好である。また、これを用いると接着剤層の低損失弾性率化が容易となり、そのはんだ耐熱性及び低誘電特性も良好となる。
ジシアンジアミド(DICY)、芳香族ジアミン(商品名「Lonzacure M-DEA」、「Lonzacure M-DETDA」等。いずれもロンザジャパン(株)製)、脂肪族アミン等のアミン系硬化剤;
フェノールノボラック樹脂、クレゾールノボラック樹脂、ビスフェノールA型ノボラック樹脂、トリアジン変性フェノールノボラック樹脂、フェノール性水酸基含有ホスファゼン(大塚化学(株)製の商品名「SPH-100」等)等のフェノール系硬化剤;
マレイン酸変性ロジンやその水素化物等のロジン系硬化剤;
環状ホスファゼン系化合物等が挙げられる。
活性エステル系硬化剤の市販品としては、例えば、
ジシクロペンタジエニルジフェノール構造を含むもので、「EXB9451」、「EXB9460」、「EXB9460S」、「HPC-8000」、「HPC-8000H」、「HPC-8000-65T」、「HPC-8000H-65TM」、「EXB-8000L」、「EXB-8000L-65TM」、「EXB-8150-65T」(以上、DIC(株)製);
ナフタレン構造を含むもので、「EXB9416-70BK」(DIC(株)製);
フェノールノボラックのアセチル化物で、「DC808」(三菱ケミカル(株)製);
フェノールノボラックのベンゾイル化物で、「YLH1026」、「YLH1030」、「YLH1048」(三菱ケミカル(株)製)等が挙げられる。
本発明のフィルム状接着材は、本発明の接着剤組成物の硬化物を含むものである。フィルム状接着材の製造方法としては、前記接着剤組成物を適当な支持体に塗工する工程、加熱して有機溶剤を揮発させることによって硬化させる工程、当該支持体を剥離する工程等を含む方法等が挙げられる。また、接着材の厚みは特に限定されないが、3~40μm程度が好ましい。支持体としては、剥離紙、剥離フィルム、後述の支持フィルム等が挙げられる。また、前記フィルム状接着材を製造する際には、前記接着剤組成物と前記接着剤以外の各種公知の接着剤組成物とを併用しても良い。
本発明の接着シートは、支持フィルムの少なくとも片面に、本発明のフィルム状接着材を含むものである。
本発明の樹脂付銅箔は、本発明のフィルム状接着材及び銅箔を含むものである。具体的には、銅箔に本発明の接着剤組成物を塗工して加熱硬化したもの、又は、銅箔に本発明のフィルム状接着材を貼り合わせたものである。銅箔としては、例えば、圧延銅箔や電解銅箔が挙げられ、各種の表面処理(粗化、防錆化等)が施されたものも使用できる。防錆化処理は、Ni,Zn,Sn等を含むメッキ液を用いたメッキ処理、クロメート処理等の、所謂鏡面化処理が挙げられる。
本発明の銅張積層板は、本発明の樹脂付銅箔及び銅箔又は絶縁性シートを含むものである。銅張積層板は、CCL(Copper Clad Laminate)とも呼ばれる。銅張積層板は、具体的には、各種公知の銅箔若しくは絶縁性シートの少なくとも片面又は両面に、前記樹脂付銅箔を、加熱下に圧着させたものである。片面に貼り合わせる場合には、他方の面に前記樹脂付銅箔とは異なるものを圧着させても良い。また、当該銅張積層板における樹脂付銅箔、銅箔及び絶縁性シートの枚数は特に限定されない。
本発明のプリント配線板は、本発明の銅張積層板の銅箔面に回路パターンを有するものである。銅張積層板の銅箔面に回路パターンを形成するパターニングの手段は、サブトラクティブ法、セミアディティブ法が挙げられる。セミアディティブ法としては、銅張積層板の銅箔面に、レジストフィルムでパターニングした後、電解銅メッキを行い、レジストを除去し、アルカリ液でエッチングする方法が挙げられる。また、当該プリント配線板における回路パターン層の厚みは特に限定されない。また、当該プリント配線板をコアとし、その上に同一のプリント配線板や他の公知のプリント配線板又はプリント回路板を積層することによって、多層基板を得ることもできる。積層の際には前記接着剤組成物と前記接着剤組成物以外の他の公知の接着剤組成物とを併用できる。また、多層基板における積層数は特に限定されない。また、積層の都度、ビアホールを挿設し、内部をメッキ処理しても良い。前記回路パターンのライン/スペース比は特に限定されないが、1μm/1μm~100μm/100μm程度が好ましい。また、前記回路パターンの高さも特に限定されないが、1~50μm程度が好ましい。
本発明のポリイミドフィルムは、本発明のポリイミド樹脂組成物の乾燥物である。
実施例1~10及び比較例1、3で使用の有機溶剤を混合した溶液を撹拌しながら沸騰させて、発生した蒸気の温度を温度計の値で確認した。
撹拌機、分水器、温度計及び窒素ガス導入管を備えた反応容器に、4,4’-[プロパン-2,2-ジイルビス(1,4-フェニレンオキシ)]ジフタル酸二無水物(商品名「BisDA-1000」、SABICイノベーティブプラスチックスジャパン合同会社製。以下、BisDAと略す。)を535.6g、エチレングリコールジメチルエーテルを716.92g及びトルエンを1672.81g仕込み、60℃まで加熱した。次いで、ダイマージアミン(商品名「PRIAMINE1075」、クローダジャパン(株)製。以下、PRIAMINE1075と表記)540.0gを徐々に添加した後、140℃まで加熱し、10時間かけてイミド化反応を実施することにより、ポリイミド樹脂(A-1)の溶液(不揮発分30%)を得た。(A-1)の軟化点を表1に示す(以下同様)。
表1に示す組成及び使用量に変更して、実施例1と同様の方法で行い、不揮発分30%のポリイミド樹脂をそれぞれ得た。
溶剤の種類を表1に示すものに変更して、実施例と同様の方法で行ったが、生成したポリアミック酸が溶解せず、ポリイミド樹脂を得られなかった。
実施例1~10及び比較例1のポリイミド樹脂組成物を、剥離紙((株)サンエー化研製)に塗工し、150℃×5分、170℃×5分の条件でそれぞれ乾燥させて、ポリイミド樹脂層を形成した積層フィルムを得た後、当該フィルムから剥離紙を剥がすことによって、膜厚25μmのポリイミドフィルム(1)を得た。
ネットワークアナライザ(Agilent Technologies社製「ENA E5071C」)と測定周波数10.124GHzのスプリットポスト誘電体共振器(QWED社製)を用いて、何も挿入していない共振器単体の共振周波数とそのピークのQ値を測定した。
次に、ポリイミドフィルム(1)を4cm×5cmに裁断して試験片を作製した後、総厚さが100μm以上となるように複数枚の試験片を重ね合わせて共振器内に挿入した後、試験片が挿入されたときの共振周波数とQ値を測定した。
比誘電率(Dk)は、共振器単体と試験片を挿入したときの共振周波数の差から算出し、誘電正接(Df)は、共振器単体と試験片を挿入したときのQ値の差と共振周波数の差から算出した。結果を表1に示す。
<芳香族テトラカルボン酸無水物>
・BisDA:4,4’-[プロパン-2,2-ジイルビス(1,4-フェニレンオキシ)]ジフタル酸二無水物、商品名:「BisDA-1000」、SABICイノベーティブプラスチックスジャパン合同会社製
・6FDA:4,4’-(ヘキサフルオロイソプロピリデン)ジフタル酸無水物、ダイキン(株)製
・BTDA:3,3’,4,4’-ベンゾフェノンテトラカルボン酸二無水物、商品名:「BTDA」、ダイセル化学工業(株)製
<ジアミン>
・DDA:ダイマージアミン、商品名:「PRIAMINE1075」、クローダジャパン(株)製
・ODA:4,4’-ジアミノフェニルエーテル、和歌山精化工業(株)製
・1,3-BAC:1,3-ビスアミノメチルシクロヘキサン、三菱ガス化学(株)製
<有機溶媒>
(B1)成分
・DMG:エチレングリコールジメチルエーテル、水100gに対する溶解度:混和
・CH:シクロヘキサノン、水100gに対する溶解度:2.5g
・DAMc:N,N-ジメチルアセトアミド、水100gに対する溶解度:混和
・MEK:メチルエチルケトン、水100gに対する溶解度:29g
(B2)成分
・Tol:トルエン、水100gに対する溶解度:45mg
・Xyl:キシレン、水100gに対する溶解度:17mg
・MCH:メチルシクロヘキサン、水100gに対する溶解度:1.4mg
・Hex:ヘキサン、水100gに対する溶解度:1.3mg
表2に示すポリイミド樹脂組成物を、剥離紙((株)サンエー化研製)に塗工し、120℃×5分の条件で乾燥させて、ポリイミド樹脂層を形成した積層フィルムを得た後、当該フィルムから剥離紙を剥がすことによって、膜厚25μmのポリイミドフィルム(2)をそれぞれ得た。得られたポリイミドフィルム(2)の比誘電率(Dk)及び誘電正接(Df)を前段落と同様の方法で測定した。結果を表2に示す。
表2に示すポリイミド樹脂組成物を、ガラス板に塗工し、150℃×1時間の条件で乾燥した後、ガラス板を剥がすことによって、膜厚25μmのポリイミドフィルム(3)をそれぞれ得た。得られたポリイミドフィルム(3)の全光線透過率とイエローインデックスを以下に記載の方法で測定した。
JIS K 7375:2008に準拠して、カラーヘーズメーターを用いて測定した。結果を表2に示す。
JIS K 7373に準拠して、色の変化を色差計(商品名:「ZE 6000」、日本電色工業(株)製)を用いた透過法にて測定した。結果を表2に示す。
評価例1
実施例1のポリイミド樹脂組成物30.0g(不揮発分9.0g)及び実施例4のポリイミド樹脂組成物70.0g(不揮発分21.0g)、架橋剤として、多官能エポキシ樹脂(商品名:「TETRAD-X」、三菱ガス化学(株)製)1.0g(不揮発分1.0g)、硬化剤として、活性エステル樹脂(商品名:「EPICLON HPC-8000-65T」、DIC(株)製)9.2g(不揮発分2.3g)及びイミダゾール系エポキシ樹脂(商品名:「キュアゾール 2E4MZ-A」、四国化成工業(株)製)0.011g(不揮発分0.011g)、無機フィラーとして、シリカ(商品名:「SC-2500-SPJ」、(株)アドマテックス製)33.3g(不揮発分33.3g)、並びに有機溶剤としてメチルエチルケトン65.4gを混合し、よく撹拌することによって、不揮発分33%の接着剤組成物を得た。
実施例2、5、8及び比較例1のポリイミド樹脂組成物100.0g(不揮発分30.0g)をそれぞれ用いて、評価例1と同様の方法で行い、不揮発分33%の接着剤組成物をそれぞれ得た。
得られた接着剤組成物を、剥離紙((株)サンエー化研製)に、乾燥後の厚みが25μmとなるようギャップコーターにて塗工した後、150℃で5分間乾燥させて接着シート(剥離紙/接着剤層)を得た。
前記の接着シート(剥離紙/接着剤層)から剥離紙を剥がし、接着剤層をプレス用支持体の上に置き、さらに接着剤層の側に同じプレス用支持体を介して、圧力5MPa、180℃で90分間加熱プレスにより硬化させることにより、熱硬化した後の接着シート(支持体/接着剤層/支持体)を作製した。その接着シートからプレス用の支持体を取り除き、接着剤層について、前段落と同様の方法で比誘電率(Dk)と誘電正接(Df)を算出した。結果を表3に示す。
前記の接着シート(剥離紙/接着剤層)から剥離紙を剥がし、市販の電解銅箔(製品名「F2-WS」、古河電気工業(株)製)(膜厚18μm)の鏡面側に重ね、もう一方の面を市販のポリイミドフィルム(商品名「カプトン100EN」、東レ・デユポン(株)製;膜厚25μm;熱膨張係数;15ppm/℃)に重ねた、ポリイミドフィルム-接着剤層-電解銅箔の積層体を作製した。次いで、プレス用支持体の上に置き、上方向より同素材から得られる支持体を介して圧力5MPa、温度180℃で90分間加熱プレスにて硬化させることにより、銅張積層板を作製した。
前記の銅張積層板について、JIS C 6481(フレキシブルプリント配線板用銅張積層板の試験方法)に準じて、引き剥がし強さ(N/mm)を測定した。結果を表3に示す。
前記の銅張積層板を温度23℃、湿度50%の恒温室に24時間放置した後、銅箔側を下にして、288℃のはんだ浴に浮かべ、発泡の有無を確認し、以下の基準で評価した。結果を表3に示す。
(評価基準)
○:外観に変化なし
×:発泡、膨れがある
Claims (13)
- 芳香族テトラカルボン酸無水物(a1)及びダイマージアミンを含むジアミン(a2)を含むモノマー群の反応物であるポリイミド(A)、並びに、異なる2種以上の有機溶剤(B)を含むポリイミド樹脂組成物であって、
(B)成分はいずれも窒素原子を含まず、かつ、共沸点が70~120℃であるポリイミド樹脂組成物。 - (a2)成分が、更に脂環族ジアミン及び/又は芳香族ジアミンを含む請求項1に記載のポリイミド樹脂組成物。
- (B)成分が、水100gに対する溶解度1g以上の有機溶剤(B1)、及び水100gに対する溶解度100mg以下の有機溶剤(B2)である、請求項1又は2に記載のポリイミド樹脂組成物。
- (B1)成分が、ケトン及び/又はエーテルである請求項3に記載のポリイミド樹脂組成物。
- (B2)成分が、脂肪族炭化水素、脂環族炭化水素及び芳香族炭化水素からなる群より選ばれる少なくとも1種である請求項3に記載のポリイミド樹脂組成物。
- (B1)成分及び(B2)成分の含有比率が、質量比で、(B1)/(B2)=10/90~90/10である請求項3~5のいずれかに記載のポリイミド樹脂組成物。
- 請求項1~6のいずれかに記載のポリイミド樹脂組成物及び架橋剤を含む接着剤組成物。
- 請求項7に記載の接着剤組成物の硬化物を含む、フィルム状接着材。
- 支持フィルムの少なくとも片面に、請求項8のフィルム状接着材を有する接着シート。
- 請求項8に記載のフィルム状接着材及び銅箔を含む、樹脂付銅箔。
- 請求項10に記載の樹脂付銅箔及び、銅箔又は絶縁性シートを含む、銅張積層板。
- 請求項11に記載の銅張積層板の銅箔面に回路パターンを有する、プリント配線板。
- 請求項1~6のいずれかに記載のポリイミド樹脂組成物の乾燥物であるポリイミドフィルム。
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