TWI636096B - 透明聚醯亞胺共聚物、聚醯亞胺樹脂組成物及成形體、以及該共聚物之製造方法 - Google Patents
透明聚醯亞胺共聚物、聚醯亞胺樹脂組成物及成形體、以及該共聚物之製造方法 Download PDFInfo
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- TWI636096B TWI636096B TW103123907A TW103123907A TWI636096B TW I636096 B TWI636096 B TW I636096B TW 103123907 A TW103123907 A TW 103123907A TW 103123907 A TW103123907 A TW 103123907A TW I636096 B TWI636096 B TW I636096B
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- Prior art keywords
- polyimide copolymer
- transparent polyimide
- copolymer
- dianhydride
- group
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 156
- 239000004642 Polyimide Substances 0.000 title claims abstract description 135
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 19
- 229920001577 copolymer Polymers 0.000 title description 9
- 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 claims abstract description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 150000004985 diamines Chemical class 0.000 claims abstract description 21
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 abstract description 25
- 238000004383 yellowing Methods 0.000 abstract description 18
- 238000003860 storage Methods 0.000 abstract description 6
- 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 abstract description 5
- 238000007334 copolymerization reaction Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- -1 amine compound Chemical class 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000010408 film Substances 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 22
- 239000003960 organic solvent Substances 0.000 description 19
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000009477 glass transition Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
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- 230000000052 comparative effect Effects 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 6
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
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- 230000003647 oxidation Effects 0.000 description 5
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- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 150000007824 aliphatic compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical group Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 229920005575 poly(amic acid) Polymers 0.000 description 4
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- 230000009467 reduction Effects 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001334 alicyclic compounds Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 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 3
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- 239000000976 ink Substances 0.000 description 3
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- 230000007774 longterm Effects 0.000 description 3
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 2
- XLOGCGOPKPCECW-UHFFFAOYSA-N 1719-83-1 Chemical compound C1=CC2C3C(=O)OC(=O)C3C1C1C(=O)OC(=O)C21 XLOGCGOPKPCECW-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 2
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- OIENNTBKMLCIOH-UHFFFAOYSA-N OC(C1=CC2=COC=C2C=C1)=O.[O] Chemical compound OC(C1=CC2=COC=C2C=C1)=O.[O] OIENNTBKMLCIOH-UHFFFAOYSA-N 0.000 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
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- 230000006872 improvement Effects 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
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- 0 *C(C(*)=C(*)C(*)=C1*)C1=* Chemical compound *C(C(*)=C(*)C(*)=C1*)C1=* 0.000 description 1
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- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- GEWWCWZGHNIUBW-UHFFFAOYSA-N 1-(4-nitrophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C([N+]([O-])=O)C=C1 GEWWCWZGHNIUBW-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
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- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
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- GTALYBOAEVNYOZ-UHFFFAOYSA-N 3-(2,3-dicarboxycyclohexyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1C(C(=O)O)CCCC1C1C(C(O)=O)C(C(O)=O)CCC1 GTALYBOAEVNYOZ-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- JUZVXGMLUGCXEQ-UHFFFAOYSA-N 3-(3,4-dicarboxycyclohexyl)cyclohexane-1,2-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(=O)O)CCC1C1C(C(O)=O)C(C(O)=O)CCC1 JUZVXGMLUGCXEQ-UHFFFAOYSA-N 0.000 description 1
- YRHYRLWIIXHESF-UHFFFAOYSA-N 3-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O YRHYRLWIIXHESF-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- XUKLTPZEKXTPBT-UHFFFAOYSA-N 3-oxatricyclo[5.2.1.01,5]dec-5-ene-2,4-dione Chemical compound C1CC2C=C3C(=O)OC(=O)C13C2 XUKLTPZEKXTPBT-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
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- 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
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- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- 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
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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- 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
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- C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
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- 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
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
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- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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| KR101928598B1 (ko) * | 2013-09-30 | 2018-12-12 | 주식회사 엘지화학 | 폴리이미드 필름 및 그 제조방법 |
| KR20210094129A (ko) | 2016-03-25 | 2021-07-28 | 코니카 미놀타 가부시키가이샤 | 폴리이미드 필름 및 그 제조 방법 |
| JP6758875B2 (ja) * | 2016-03-29 | 2020-09-23 | ソマール株式会社 | ポリイミド樹脂組成物およびそれを用いた成形体 |
| TWI609897B (zh) * | 2017-02-15 | 2018-01-01 | 律勝科技股份有限公司 | 聚醯亞胺樹脂及其製造方法與薄膜 |
| KR102524863B1 (ko) * | 2017-03-29 | 2023-04-24 | 도레이 카부시키가이샤 | 도전층 구비 필름, 터치 패널, 도전층 구비 필름의 제조 방법 및 터치 패널의 제조 방법 |
| TWI655097B (zh) * | 2017-12-27 | 2019-04-01 | 財團法人工業技術研究院 | 光波導元件及其製造方法 |
| CN108218797B (zh) * | 2018-01-16 | 2020-03-17 | 同济大学 | 液晶分子改性嘧啶二胺单体、源自其的液晶取向材料及其合成方法 |
| CN112313264A (zh) * | 2018-04-20 | 2021-02-02 | 宇部兴产株式会社 | 聚酰亚胺、层积体和包含它们的电子器件 |
| TWI833752B (zh) * | 2018-05-16 | 2024-03-01 | 美商杜邦股份有限公司 | 用於電子裝置中的聚合物 |
| EP3819283A4 (en) * | 2018-07-05 | 2022-03-16 | Unitika Ltd. | METHOD OF MAKING AN ORGANIC COMPOUND |
| CN110105571B (zh) * | 2019-05-31 | 2020-10-02 | 中国科学院大连化学物理研究所 | 一种新型嵌段聚酰亚胺材料及其制备与在气体分离中的应用 |
| KR102286207B1 (ko) * | 2020-05-04 | 2021-08-06 | 에스케이이노베이션 주식회사 | 폴리이미드계 필름 및 이를 포함하는 플렉서블 디스플레이 패널 |
| JP2023527141A (ja) | 2020-11-19 | 2023-06-27 | エルジー・ケム・リミテッド | ディスプレイ装置用またはフレキシブルディスプレイ装置用基板、およびディスプレイ装置またはフレキシブルディスプレイ装置 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TW469358B (en) * | 1998-05-21 | 2001-12-21 | Du Pont | Polyimide photo alignment film, active matrix liquid crystal display device, and method for preparing an alignment later for liquid crystal displays |
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| US4629777A (en) * | 1983-05-18 | 1986-12-16 | Ciba-Geigy Corporation | Polyimides, a process for their preparation and their use |
| US4912197A (en) * | 1987-08-14 | 1990-03-27 | E. I. Du Pont De Nemours And Company | Highly soluble clear polyimides |
| US4897092A (en) | 1989-02-27 | 1990-01-30 | Air Products And Chemicals, Inc. | Polyimide membrane having improved flux |
| US4981497A (en) | 1989-06-01 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Amine-modified polyimide membranes |
| US4932982A (en) * | 1989-06-01 | 1990-06-12 | E. I. Du Pont De Nemours And Company | Copolyimide gas separation membranes derived from substituted phenylene diamines and substituted methylene dianilines |
| JP2950521B2 (ja) * | 1991-03-18 | 1999-09-20 | 日本電信電話株式会社 | 光導波路用ポリイミド光学材料 |
| JPH05271411A (ja) * | 1992-03-26 | 1993-10-19 | Hitachi Chem Co Ltd | イミドオリゴマ型耐熱性樹脂組成物およびその製造方法 |
| JP3091657B2 (ja) * | 1994-12-26 | 2000-09-25 | キヤノン株式会社 | 電子写真感光体、該電子写真感光体を有するプロセスカ−トリッジ及び電子写真装置 |
| US5649045A (en) | 1995-12-13 | 1997-07-15 | Amoco Corporation | Polymide optical waveguide structures |
| JPH09258048A (ja) * | 1996-03-25 | 1997-10-03 | Nikon Corp | 集光グレーティングカップラの設計方法および製造方法 |
| US5750641A (en) | 1996-05-23 | 1998-05-12 | Minnesota Mining And Manufacturing Company | Polyimide angularity enhancement layer |
| JP2001040209A (ja) * | 1999-07-29 | 2001-02-13 | Hitachi Chemical Dupont Microsystems Ltd | 光配向液晶配向膜用組成物、光配向液晶配向膜、液晶挟持基板及び液晶表示装置 |
| US20020192445A1 (en) * | 2001-05-03 | 2002-12-19 | Ezzell Stephen A. | Plastic substrate for display applications |
| JP2003176354A (ja) | 2001-12-11 | 2003-06-24 | Manac Inc | 透明な耐熱性ポリイミドフイルム |
| US20050256295A1 (en) | 2004-03-31 | 2005-11-17 | Katsuya Sakayori | Polymer compound, highly transparent polyimide, resin composition and article |
| JP4821157B2 (ja) | 2004-03-31 | 2011-11-24 | 大日本印刷株式会社 | 高分子化合物、高透明性ポリイミド、樹脂組成物及び物品 |
| JP5018082B2 (ja) * | 2006-12-28 | 2012-09-05 | 新日本理化株式会社 | 新規なポリイミド樹脂組成物及びそのワニス |
| JP5321193B2 (ja) | 2009-03-30 | 2013-10-23 | デクセリアルズ株式会社 | ポリアミック酸溶液、ポリイミド及び光学装置 |
| JP2011140563A (ja) | 2010-01-07 | 2011-07-21 | Hitachi Chem Co Ltd | ポリイミド及び樹脂組成物 |
| JP2011144260A (ja) | 2010-01-14 | 2011-07-28 | Mitsubishi Gas Chemical Co Inc | 粘着剤及び粘着テープ |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW469358B (en) * | 1998-05-21 | 2001-12-21 | Du Pont | Polyimide photo alignment film, active matrix liquid crystal display device, and method for preparing an alignment later for liquid crystal displays |
Also Published As
| Publication number | Publication date |
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| WO2015008643A1 (ja) | 2015-01-22 |
| CN105408393B (zh) | 2019-08-06 |
| JP6230308B2 (ja) | 2017-11-15 |
| KR102097312B1 (ko) | 2020-04-06 |
| JP2015021022A (ja) | 2015-02-02 |
| CN105408393A (zh) | 2016-03-16 |
| KR20160032181A (ko) | 2016-03-23 |
| US20160168328A1 (en) | 2016-06-16 |
| TW201522504A (zh) | 2015-06-16 |
| US10189949B2 (en) | 2019-01-29 |
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