WO2023149435A1 - Composition de résine, objet moulé et film - Google Patents
Composition de résine, objet moulé et film Download PDFInfo
- Publication number
- WO2023149435A1 WO2023149435A1 PCT/JP2023/003097 JP2023003097W WO2023149435A1 WO 2023149435 A1 WO2023149435 A1 WO 2023149435A1 JP 2023003097 W JP2023003097 W JP 2023003097W WO 2023149435 A1 WO2023149435 A1 WO 2023149435A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyimide
- bis
- dianhydride
- film
- resin
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 35
- -1 molded object Substances 0.000 title description 5
- 229920001721 polyimide Polymers 0.000 claims abstract description 126
- 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 87
- 239000004642 Polyimide Substances 0.000 claims abstract description 78
- 239000011347 resin Substances 0.000 claims abstract description 58
- 229920005989 resin Polymers 0.000 claims abstract description 58
- 229940081735 acetylcellulose Drugs 0.000 claims abstract description 56
- 229920002301 cellulose acetate Polymers 0.000 claims abstract description 56
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 claims abstract description 54
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims abstract description 33
- 150000004985 diamines Chemical class 0.000 claims abstract description 26
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 24
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- 238000002834 transmittance Methods 0.000 claims description 18
- 239000012461 cellulose resin Substances 0.000 claims description 9
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 7
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical group C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000004580 weight loss Effects 0.000 claims description 6
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 claims description 5
- SNHKMHUMILUWSJ-UHFFFAOYSA-N 5-(1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-yl)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CC2C(=O)OC(=O)C2CC1C1CC2C(=O)OC(=O)C2CC1 SNHKMHUMILUWSJ-UHFFFAOYSA-N 0.000 claims description 4
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 abstract 1
- 229920000178 Acrylic resin Polymers 0.000 abstract 1
- 239000010408 film Substances 0.000 description 87
- 239000009719 polyimide resin Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 229920005575 poly(amic acid) Polymers 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 229920002284 Cellulose triacetate Polymers 0.000 description 7
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 description 7
- 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 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical class OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 125000006159 dianhydride group Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JPZRPCNEISCANI-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F JPZRPCNEISCANI-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
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- WVOLTBSCXRRQFR-DLBZAZTESA-N cannabidiolic acid Chemical compound OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000000758 substrate Substances 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
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013039 cover film Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 150000002009 diols 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
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 description 1
- STIUJDCDGZSXGO-UHFFFAOYSA-N (3-amino-4-phenoxyphenyl)-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)=C1 STIUJDCDGZSXGO-UHFFFAOYSA-N 0.000 description 1
- YKNMIGJJXKBHJE-UHFFFAOYSA-N (3-aminophenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(N)=C1 YKNMIGJJXKBHJE-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
- SBHHKGFHJWTZJN-UHFFFAOYSA-N 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C)(C(O)=O)C1C(O)=O SBHHKGFHJWTZJN-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 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
- 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
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- FVFYRXJKYAVFSB-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diamine Chemical compound NC1=C(F)C(F)=C(N)C(F)=C1F FVFYRXJKYAVFSB-UHFFFAOYSA-N 0.000 description 1
- BHPCMPVIMAJIQS-UHFFFAOYSA-N 2,3,5,6-tetrakis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=C(C(F)(F)F)C(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F BHPCMPVIMAJIQS-UHFFFAOYSA-N 0.000 description 1
- DJOVAUMVUZNCRR-UHFFFAOYSA-N 2,3,5-trifluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C(F)=C1F DJOVAUMVUZNCRR-UHFFFAOYSA-N 0.000 description 1
- LOSUMUGGQHVNDI-UHFFFAOYSA-N 2,3,5-tris(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F LOSUMUGGQHVNDI-UHFFFAOYSA-N 0.000 description 1
- YMDMDDUYDDFCSX-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F YMDMDDUYDDFCSX-UHFFFAOYSA-N 0.000 description 1
- WRFSJAVIFPITPG-UHFFFAOYSA-N 2,3-difluorobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(F)=C1F WRFSJAVIFPITPG-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- CEQNIRIQYOUDCF-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F CEQNIRIQYOUDCF-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- ZKTNFNZZMROBEB-UHFFFAOYSA-N 2,5-difluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C=C1F ZKTNFNZZMROBEB-UHFFFAOYSA-N 0.000 description 1
- PVXRBSHBFJXTNM-UHFFFAOYSA-N 2,6-bis(3-aminophenoxy)benzonitrile Chemical compound NC1=CC=CC(OC=2C(=C(OC=3C=C(N)C=CC=3)C=CC=2)C#N)=C1 PVXRBSHBFJXTNM-UHFFFAOYSA-N 0.000 description 1
- OGVUUAGLCNYUGO-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C(C(F)(F)F)=C1 OGVUUAGLCNYUGO-UHFFFAOYSA-N 0.000 description 1
- XFWCWQUDUPQGKG-UHFFFAOYSA-N 2,6-difluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C(F)=C1 XFWCWQUDUPQGKG-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- DYGPKZRYPCCCLU-UHFFFAOYSA-N 2-(aminomethoxy)ethoxymethanamine Chemical compound NCOCCOCN DYGPKZRYPCCCLU-UHFFFAOYSA-N 0.000 description 1
- LJVGYWLSCKCZQK-UHFFFAOYSA-N 2-[2-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCCCC1CCN LJVGYWLSCKCZQK-UHFFFAOYSA-N 0.000 description 1
- NIQFAJBKEHPUAM-UHFFFAOYSA-N 2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethanamine Chemical compound NCCOCCOCCOCCN NIQFAJBKEHPUAM-UHFFFAOYSA-N 0.000 description 1
- HKJUXXFTANXMGQ-UHFFFAOYSA-N 2-[2-[2-(aminomethoxy)ethoxy]ethoxy]ethoxymethanamine Chemical compound NCOCCOCCOCCOCN HKJUXXFTANXMGQ-UHFFFAOYSA-N 0.000 description 1
- IFZOPNLVYZYSMQ-UHFFFAOYSA-N 2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethanamine Chemical compound NCCOCCOCCOCCOCCN IFZOPNLVYZYSMQ-UHFFFAOYSA-N 0.000 description 1
- STMZGJLCKJFMLQ-UHFFFAOYSA-N 2-[3-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCCC(CCN)C1 STMZGJLCKJFMLQ-UHFFFAOYSA-N 0.000 description 1
- XUXZELZSNNYLRE-UHFFFAOYSA-N 2-[4-(2-aminoethyl)cyclohexyl]ethanamine Chemical compound NCCC1CCC(CCN)CC1 XUXZELZSNNYLRE-UHFFFAOYSA-N 0.000 description 1
- DCMBSPNTFXPUMO-UHFFFAOYSA-N 2-benzofuran-5-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=COC=C21 DCMBSPNTFXPUMO-UHFFFAOYSA-N 0.000 description 1
- FXFTWEVIIHVHDS-UHFFFAOYSA-N 2-fluorobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(F)=C1 FXFTWEVIIHVHDS-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
- OLQWMCSSZKNOLQ-UHFFFAOYSA-N 3-(2,5-dioxooxolan-3-yl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-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
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 1
- TYKLCAKICHXQNE-UHFFFAOYSA-N 3-[(2,3-dicarboxyphenyl)methyl]phthalic acid Chemical compound OC(=O)C1=CC=CC(CC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O TYKLCAKICHXQNE-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- UCFMKTNJZCYBBJ-UHFFFAOYSA-N 3-[1-(2,3-dicarboxyphenyl)ethyl]phthalic acid Chemical compound C=1C=CC(C(O)=O)=C(C(O)=O)C=1C(C)C1=CC=CC(C(O)=O)=C1C(O)=O UCFMKTNJZCYBBJ-UHFFFAOYSA-N 0.000 description 1
- DTSHAMICSDYNNJ-UHFFFAOYSA-N 3-[1-(3-aminophenyl)-1-phenylethyl]aniline Chemical compound C=1C=CC(N)=CC=1C(C=1C=C(N)C=CC=1)(C)C1=CC=CC=C1 DTSHAMICSDYNNJ-UHFFFAOYSA-N 0.000 description 1
- VTVHCZXORLURPD-UHFFFAOYSA-N 3-[1-(4-aminophenyl)-1-phenylethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C=1C=C(N)C=CC=1)(C)C1=CC=CC=C1 VTVHCZXORLURPD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DVXYMCJCMDTSQA-UHFFFAOYSA-N 3-[2-(3-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC(N)=CC=1C(C)(C)C1=CC=CC(N)=C1 DVXYMCJCMDTSQA-UHFFFAOYSA-N 0.000 description 1
- HIYRIYOUSQLJHP-UHFFFAOYSA-N 3-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC(N)=CC=1C(C)(C)C1=CC=C(N)C=C1 HIYRIYOUSQLJHP-UHFFFAOYSA-N 0.000 description 1
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 1
- FVUIAOHMTFHVTE-UHFFFAOYSA-N 3-[2-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCOCCCN FVUIAOHMTFHVTE-UHFFFAOYSA-N 0.000 description 1
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 1
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XWQGVRJTNLTVBP-UHFFFAOYSA-N 3-[4-[2-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 XWQGVRJTNLTVBP-UHFFFAOYSA-N 0.000 description 1
- UCQABCHSIIXVOY-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]phenoxy]aniline Chemical group NC1=CC=CC(OC=2C=CC(=CC=2)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 UCQABCHSIIXVOY-UHFFFAOYSA-N 0.000 description 1
- JERFEOKUSPGKGV-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(SC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 JERFEOKUSPGKGV-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- YJRWUTMEGNLLNV-UHFFFAOYSA-N 3-[6-(3-aminophenoxy)pyridin-2-yl]oxyaniline Chemical compound NC1=CC=CC(OC=2N=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 YJRWUTMEGNLLNV-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
- OQASAQLBBINTDT-UHFFFAOYSA-N 3-[[5'-(3-aminophenoxy)-1,1,1',1'-tetramethyl-3,3'-spirobi[2h-indene]-5-yl]oxy]aniline Chemical compound C12=CC(OC=3C=C(N)C=CC=3)=CC=C2C(C)(C)CC1(C1=C2)CC(C)(C)C1=CC=C2OC1=CC=CC(N)=C1 OQASAQLBBINTDT-UHFFFAOYSA-N 0.000 description 1
- HYTCSCBDAFJMIP-UHFFFAOYSA-N 3-ethyl-1,1-dimethylurea Chemical compound CCNC(=O)N(C)C HYTCSCBDAFJMIP-UHFFFAOYSA-N 0.000 description 1
- SSBQKUNCMVRQNK-UHFFFAOYSA-N 4,11-dioxatetracyclo[6.5.1.02,7.09,13]tetradecane-3,5,10,12-tetrone Chemical compound C12CC(=O)OC(=O)C2C2C3C(=O)OC(=O)C3C1C2 SSBQKUNCMVRQNK-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
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FWOLORXQTIGHFX-UHFFFAOYSA-N 4-(4-amino-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluoroaniline Chemical compound FC1=C(F)C(N)=C(F)C(F)=C1C1=C(F)C(F)=C(N)C(F)=C1F FWOLORXQTIGHFX-UHFFFAOYSA-N 0.000 description 1
- UVJXASLHNGDGTJ-UHFFFAOYSA-N 4-(4-amino-2,3,6-trifluorophenyl)-2,3,5-trifluoroaniline Chemical compound FC1=C(F)C(N)=CC(F)=C1C1=C(F)C=C(N)C(F)=C1F UVJXASLHNGDGTJ-UHFFFAOYSA-N 0.000 description 1
- MVLHGDPHQWMPPD-UHFFFAOYSA-N 4-(4-amino-2,3-difluorophenyl)-2,3-difluoroaniline Chemical compound FC1=C(F)C(N)=CC=C1C1=CC=C(N)C(F)=C1F MVLHGDPHQWMPPD-UHFFFAOYSA-N 0.000 description 1
- VSCWVWFFQWMDGE-UHFFFAOYSA-N 4-(4-amino-2,5-difluorophenyl)-2,5-difluoroaniline Chemical compound C1=C(F)C(N)=CC(F)=C1C1=CC(F)=C(N)C=C1F VSCWVWFFQWMDGE-UHFFFAOYSA-N 0.000 description 1
- JQVZQTDUPLLZLN-UHFFFAOYSA-N 4-(4-amino-2,6-difluorophenyl)-3,5-difluoroaniline Chemical compound FC1=CC(N)=CC(F)=C1C1=C(F)C=C(N)C=C1F JQVZQTDUPLLZLN-UHFFFAOYSA-N 0.000 description 1
- DBGKAVJUYQVDRR-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)-2,3-difluoroaniline Chemical compound FC1=CC(N)=CC=C1C1=CC=C(N)C(F)=C1F DBGKAVJUYQVDRR-UHFFFAOYSA-N 0.000 description 1
- CZKBTNZSDARLKJ-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)-2,5-difluoroaniline Chemical compound FC1=CC(N)=CC=C1C1=CC(F)=C(N)C=C1F CZKBTNZSDARLKJ-UHFFFAOYSA-N 0.000 description 1
- IHXLBFONUCAPHB-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)-2-fluoroaniline Chemical compound FC1=CC(N)=CC=C1C1=CC=C(N)C(F)=C1 IHXLBFONUCAPHB-UHFFFAOYSA-N 0.000 description 1
- QDGGDWPKUSREMJ-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)-3,5-difluoroaniline Chemical compound FC1=CC(N)=CC=C1C1=C(F)C=C(N)C=C1F QDGGDWPKUSREMJ-UHFFFAOYSA-N 0.000 description 1
- LSJAPRRUOIMQSN-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)-3-fluoroaniline Chemical compound FC1=CC(N)=CC=C1C1=CC=C(N)C=C1F LSJAPRRUOIMQSN-UHFFFAOYSA-N 0.000 description 1
- CQDSKVXWFVMITN-UHFFFAOYSA-N 4-(4-amino-3-fluorophenyl)-2,3-difluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1=CC=C(N)C(F)=C1F CQDSKVXWFVMITN-UHFFFAOYSA-N 0.000 description 1
- DZJGFGDNVWRRHE-UHFFFAOYSA-N 4-(4-amino-3-fluorophenyl)-2,5-difluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1=CC(F)=C(N)C=C1F DZJGFGDNVWRRHE-UHFFFAOYSA-N 0.000 description 1
- LVNPGQZSPDFZNC-UHFFFAOYSA-N 4-(4-amino-3-fluorophenyl)-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1=CC=C(N)C(F)=C1 LVNPGQZSPDFZNC-UHFFFAOYSA-N 0.000 description 1
- SWLKCALZKGKVMG-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5,6-tetrafluoroaniline Chemical compound C1=CC(N)=CC=C1C1=C(F)C(F)=C(N)C(F)=C1F SWLKCALZKGKVMG-UHFFFAOYSA-N 0.000 description 1
- VVAHNFVUWVUUBV-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5,6-tetrakis(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=C(C(F)(F)F)C(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F VVAHNFVUWVUUBV-UHFFFAOYSA-N 0.000 description 1
- ZKIFBGFMMIGHHJ-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5-trifluoroaniline Chemical compound C1=CC(N)=CC=C1C1=C(F)C=C(N)C(F)=C1F ZKIFBGFMMIGHHJ-UHFFFAOYSA-N 0.000 description 1
- JQAUUCHOSMZRQT-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,5-tris(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=C(C(F)(F)F)C=C(N)C(C(F)(F)F)=C1C(F)(F)F JQAUUCHOSMZRQT-UHFFFAOYSA-N 0.000 description 1
- KOQXUSAOCXKEAB-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,6-trifluoroaniline Chemical compound C1=CC(N)=CC=C1C1=CC(F)=C(N)C(F)=C1F KOQXUSAOCXKEAB-UHFFFAOYSA-N 0.000 description 1
- BJTFQMWOKTWNTL-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3,6-tris(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F BJTFQMWOKTWNTL-UHFFFAOYSA-N 0.000 description 1
- DHRKBGDIJSRWIP-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-bis(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F DHRKBGDIJSRWIP-UHFFFAOYSA-N 0.000 description 1
- ONBVHGIWMYBABS-UHFFFAOYSA-N 4-(4-aminophenyl)-2,3-difluoroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(F)=C1F ONBVHGIWMYBABS-UHFFFAOYSA-N 0.000 description 1
- SOUQHOLWDUFHBP-UHFFFAOYSA-N 4-(4-aminophenyl)-2,5-bis(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F SOUQHOLWDUFHBP-UHFFFAOYSA-N 0.000 description 1
- BQTIVQHKHQKOOI-UHFFFAOYSA-N 4-(4-aminophenyl)-2,5-difluoroaniline Chemical compound C1=CC(N)=CC=C1C1=CC(F)=C(N)C=C1F BQTIVQHKHQKOOI-UHFFFAOYSA-N 0.000 description 1
- BYAXRGGDRFFTAP-UHFFFAOYSA-N 4-(4-aminophenyl)-2-(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 BYAXRGGDRFFTAP-UHFFFAOYSA-N 0.000 description 1
- UPJLEUXHPQVGHI-UHFFFAOYSA-N 4-(4-aminophenyl)-2-fluoroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(F)=C1 UPJLEUXHPQVGHI-UHFFFAOYSA-N 0.000 description 1
- PCIVIPVWWQZHPX-UHFFFAOYSA-N 4-(4-aminophenyl)-3,5-bis(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=C(C(F)(F)F)C=C(N)C=C1C(F)(F)F PCIVIPVWWQZHPX-UHFFFAOYSA-N 0.000 description 1
- NCTHRPSXTZGESD-UHFFFAOYSA-N 4-(4-aminophenyl)-3,5-difluoroaniline Chemical compound C1=CC(N)=CC=C1C1=C(F)C=C(N)C=C1F NCTHRPSXTZGESD-UHFFFAOYSA-N 0.000 description 1
- XERAWPSPVRYXCU-UHFFFAOYSA-N 4-(4-aminophenyl)-3-fluoroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1F XERAWPSPVRYXCU-UHFFFAOYSA-N 0.000 description 1
- IOJCFCLZQBXCIQ-UHFFFAOYSA-N 4-(4-hydroxy-2,3,5-trimethylphenyl)-2,3,6-trimethylphenol Chemical compound CC1=C(O)C(C)=CC(C=2C(=C(C)C(O)=C(C)C=2)C)=C1C IOJCFCLZQBXCIQ-UHFFFAOYSA-N 0.000 description 1
- GTFQLBWTUKSJQG-UHFFFAOYSA-N 4-(4-hydroxy-2-methylphenyl)-3-methylphenol Chemical compound CC1=CC(O)=CC=C1C1=CC=C(O)C=C1C GTFQLBWTUKSJQG-UHFFFAOYSA-N 0.000 description 1
- YGYPMFPGZQPETF-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C(C)C(O)=C(C)C=2)=C1 YGYPMFPGZQPETF-UHFFFAOYSA-N 0.000 description 1
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- OPVHOFITDJSMOD-UHFFFAOYSA-N 4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1OC1=CC=CC2=C1C(=O)OC2=O OPVHOFITDJSMOD-UHFFFAOYSA-N 0.000 description 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-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
- CJXRYVQHINFIKO-UHFFFAOYSA-N 4-[1-(4-aminophenyl)-1-phenylethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C=1C=CC(N)=CC=1)(C)C1=CC=CC=C1 CJXRYVQHINFIKO-UHFFFAOYSA-N 0.000 description 1
- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- KWOIWTRRPFHBSI-UHFFFAOYSA-N 4-[2-[3-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC(C(C)(C)C=2C=CC(N)=CC=2)=CC=1C(C)(C)C1=CC=C(N)C=C1 KWOIWTRRPFHBSI-UHFFFAOYSA-N 0.000 description 1
- HESXPOICBNWMPI-UHFFFAOYSA-N 4-[2-[4-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(N)=CC=2)C=CC=1C(C)(C)C1=CC=C(N)C=C1 HESXPOICBNWMPI-UHFFFAOYSA-N 0.000 description 1
- FOCQMELIWLXNGL-UHFFFAOYSA-N 4-[3-(3,4-dicarboxybenzoyl)benzoyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 FOCQMELIWLXNGL-UHFFFAOYSA-N 0.000 description 1
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 1
- FOMRNNDDNMWZFO-UHFFFAOYSA-N 4-[4-(3,4-dicarboxybenzoyl)benzoyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=C1 FOMRNNDDNMWZFO-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- DSXVBZHFXLKHJU-UHFFFAOYSA-N 4-[4-[2-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 DSXVBZHFXLKHJU-UHFFFAOYSA-N 0.000 description 1
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- SXTPNMJRVQKNRN-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1SC(C=C1)=CC=C1OC1=CC=C(N)C=C1 SXTPNMJRVQKNRN-UHFFFAOYSA-N 0.000 description 1
- UTDAGHZGKXPRQI-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(S(=O)(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 UTDAGHZGKXPRQI-UHFFFAOYSA-N 0.000 description 1
- IEWKGDKMUYHORO-UHFFFAOYSA-N 4-[4-amino-2,3-bis(trifluoromethyl)phenyl]-2,3-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F IEWKGDKMUYHORO-UHFFFAOYSA-N 0.000 description 1
- QMEPPSJSNJRUEV-UHFFFAOYSA-N 4-[4-amino-2,5-bis(trifluoromethyl)phenyl]-2,5-bis(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC(C(F)(F)F)=C1C1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F QMEPPSJSNJRUEV-UHFFFAOYSA-N 0.000 description 1
- HHJLKTCENRQCEF-UHFFFAOYSA-N 4-[4-amino-2,6-bis(trifluoromethyl)phenyl]-3,5-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC(C(F)(F)F)=C1C1=C(C(F)(F)F)C=C(N)C=C1C(F)(F)F HHJLKTCENRQCEF-UHFFFAOYSA-N 0.000 description 1
- RBVRTNVTEFUCEZ-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-2,5-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F RBVRTNVTEFUCEZ-UHFFFAOYSA-N 0.000 description 1
- FADZWOLRHIYXHJ-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-2-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 FADZWOLRHIYXHJ-UHFFFAOYSA-N 0.000 description 1
- DSUGHLRTIRKNES-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3,5-bis(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=C(C(F)(F)F)C=C(N)C=C1C(F)(F)F DSUGHLRTIRKNES-UHFFFAOYSA-N 0.000 description 1
- HUOGDCDMDLBVKW-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2,3-bis(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F HUOGDCDMDLBVKW-UHFFFAOYSA-N 0.000 description 1
- AEVMLQUCUUJHLM-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2,5-bis(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F AEVMLQUCUUJHLM-UHFFFAOYSA-N 0.000 description 1
- PJWQLRKRVISYPL-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 PJWQLRKRVISYPL-UHFFFAOYSA-N 0.000 description 1
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 1
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 1
- ILCGTNBULCHWOE-UHFFFAOYSA-N 4-[[4-aminobutyl(dimethyl)silyl]oxy-dimethylsilyl]butan-1-amine Chemical compound NCCCC[Si](C)(C)O[Si](C)(C)CCCCN ILCGTNBULCHWOE-UHFFFAOYSA-N 0.000 description 1
- MEKZWIPEPTYXCJ-UHFFFAOYSA-N 4-[[5'-(4-aminophenoxy)-1,1,1',1'-tetramethyl-3,3'-spirobi[2h-indene]-5-yl]oxy]aniline Chemical compound C12=CC(OC=3C=CC(N)=CC=3)=CC=C2C(C)(C)CC1(C1=C2)CC(C)(C)C1=CC=C2OC1=CC=C(N)C=C1 MEKZWIPEPTYXCJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JYCTWJFSRDBYJX-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-3a,4,5,9b-tetrahydrobenzo[e][2]benzofuran-1,3-dione Chemical compound O=C1OC(=O)CC1C1C2=CC=CC=C2C(C(=O)OC2=O)C2C1 JYCTWJFSRDBYJX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 1
- DHMJUAQOLCAAIS-UHFFFAOYSA-N 5-[4-[1-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]cyclohexyl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1OC(C=C1)=CC=C1C1(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)CCCCC1 DHMJUAQOLCAAIS-UHFFFAOYSA-N 0.000 description 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 1
- FMACFWAQBPYRFO-UHFFFAOYSA-N 5-[9-(1,3-dioxo-2-benzofuran-5-yl)fluoren-9-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 FMACFWAQBPYRFO-UHFFFAOYSA-N 0.000 description 1
- QVEIRZNRYOJFCL-UHFFFAOYSA-N 6053-46-9 Chemical compound O=C1OC(=O)C2CC1C1C2CC(=O)OC1=O QVEIRZNRYOJFCL-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- JGZHIFHECHWXLT-UHFFFAOYSA-N CCC(CC(CN)C(F)(F)F)N Chemical compound CCC(CC(CN)C(F)(F)F)N JGZHIFHECHWXLT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- UTOALSUBURUJJE-UHFFFAOYSA-N OC(C(C(CC1CCC(CC(C(C(O)=O)=CC=C2C(O3)=O)=C2C3=O)CC1)=C1C(O2)=O)=CC=C1C2=O)=O Chemical compound OC(C(C(CC1CCC(CC(C(C(O)=O)=CC=C2C(O3)=O)=C2C3=O)CC1)=C1C(O2)=O)=CC=C1C2=O)=O UTOALSUBURUJJE-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- KEUCYUPOICDBOG-UHFFFAOYSA-N [2-(aminomethyl)-5-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1C2C(CN)CC1C(CN)C2 KEUCYUPOICDBOG-UHFFFAOYSA-N 0.000 description 1
- IVGBGCPUDUTSHT-UHFFFAOYSA-N [3-(3-aminobenzoyl)phenyl]-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(C=CC=2)C(=O)C=2C=C(N)C=CC=2)=C1 IVGBGCPUDUTSHT-UHFFFAOYSA-N 0.000 description 1
- UVXIFYUJZWURAR-UHFFFAOYSA-N [3-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 UVXIFYUJZWURAR-UHFFFAOYSA-N 0.000 description 1
- OTKFKCIRTBTDKK-UHFFFAOYSA-N [3-(aminomethyl)-5-bicyclo[2.2.1]heptanyl]methanamine Chemical compound C1C(CN)C2C(CN)CC1C2 OTKFKCIRTBTDKK-UHFFFAOYSA-N 0.000 description 1
- WYYLAHMAYZBJOI-UHFFFAOYSA-N [3-[4-(3-aminophenoxy)benzoyl]phenyl]-[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=C(C=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WYYLAHMAYZBJOI-UHFFFAOYSA-N 0.000 description 1
- CXISKMDTEFIGTG-UHFFFAOYSA-N [4-(1,3-dioxo-2-benzofuran-5-carbonyl)oxyphenyl] 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(OC=2C=CC(OC(=O)C=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)=O)=C1 CXISKMDTEFIGTG-UHFFFAOYSA-N 0.000 description 1
- KJGPUSGHNHJCNO-UHFFFAOYSA-N [4-(3-aminobenzoyl)phenyl]-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=C(N)C=CC=2)=C1 KJGPUSGHNHJCNO-UHFFFAOYSA-N 0.000 description 1
- DBCMPVCYHLRHND-UHFFFAOYSA-N [4-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C(=O)C=2C=CC(N)=CC=2)C=C1 DBCMPVCYHLRHND-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- HKWWRLBGQRLBRM-UHFFFAOYSA-N [4-[4-(4-aminophenoxy)benzoyl]phenyl]-[4-(4-aminophenoxy)phenyl]methanone Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HKWWRLBGQRLBRM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- MRSWDOKCESOYBI-UHFFFAOYSA-N anthracene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C=C(C(C(=O)O)=C3)C(O)=O)C3=CC2=C1 MRSWDOKCESOYBI-UHFFFAOYSA-N 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 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 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- CJYIPJMCGHGFNN-UHFFFAOYSA-N bicyclo[2.2.1]heptane-2,3,5,6-tetracarboxylic acid Chemical compound C1C2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O CJYIPJMCGHGFNN-UHFFFAOYSA-N 0.000 description 1
- XQBSPQLKNWMPMG-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O XQBSPQLKNWMPMG-UHFFFAOYSA-N 0.000 description 1
- SONDVQSYBUQGDH-UHFFFAOYSA-N bis(3-amino-4-phenoxyphenyl)methanone Chemical compound NC1=CC(C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)=CC=C1OC1=CC=CC=C1 SONDVQSYBUQGDH-UHFFFAOYSA-N 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- BBRLKRNNIMVXOD-UHFFFAOYSA-N bis[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 BBRLKRNNIMVXOD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000000071 blow moulding Methods 0.000 description 1
- 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 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229920005994 diacetyl cellulose Polymers 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- GBASTSRAHRGUAB-UHFFFAOYSA-N ethylenetetracarboxylic dianhydride Chemical compound O=C1OC(=O)C2=C1C(=O)OC2=O GBASTSRAHRGUAB-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-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
- UMSVUULWTOXCQY-UHFFFAOYSA-N phenanthrene-1,2,7,8-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3C=CC2=C1C(O)=O UMSVUULWTOXCQY-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
- C08L1/12—Cellulose acetate
-
- 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
Definitions
- the present invention relates to resin compositions and molded articles such as films.
- transparent polyimide Because transparent polyimide has transparency and high heat resistance, it is used for display substrates and cover films.
- a normal polyimide film is obtained by coating a polyamic acid solution, which is a polyimide precursor, on a support in the form of a film, and subjecting it to a high temperature treatment to remove the solvent and perform thermal imidization at the same time.
- the heating temperature for thermal imidization is high (for example, 300 ° C. or higher), and coloring (increase in yellowness) due to heating is likely to occur, making it difficult to apply to applications requiring high transparency such as cover films for displays. Have difficulty.
- Patent Document 1 discloses that polyimides containing bis-trimellitic anhydride esters as tetracarboxylic dianhydride components are soluble in low-boiling solvents such as methylene chloride and have excellent transparency and mechanical strength. is described.
- an object of the present invention is to provide a transparent film having high heat resistance and excellent transparency and light resistance, and a resin composition used for producing the same.
- the present inventors have found that polyimides having a specific chemical structure and acetylcellulose-based resins show compatibility, and by using a resin composition in which these are mixed, a highly transparent film can be produced without impairing the excellent heat resistance of polyimides. We have found that it is possible, and have solved the above problems.
- One aspect of the present invention relates to a film and a resin composition containing a polyimide resin and an acetylcellulose resin.
- the resin composition may contain a polyimide resin and an acetylcellulose resin in a weight ratio ranging from 98:2 to 2:98.
- the polyimide contains an alicyclic tetracarboxylic dianhydride as the tetracarboxylic dianhydride component, an alicyclic tetracarboxylic dianhydride as the tetracarboxylic dianhydride component, and a fluoroalkyl-substituted benzidine as the diamine component. including.
- the amount of the alicyclic tetracarboxylic dianhydride relative to the total amount of the tetracarboxylic dianhydride component of the polyimide is preferably 10 to 100 mol%.
- the alicyclic tetracarboxylic dianhydrides include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,4 ,5-cyclohexanetetracarboxylic dianhydride and 1,1′-bicyclohexane-3,3′,4,4′tetracarboxylic acid-3,4:3′,4′-dianhydride are preferred.
- the amount of the fluoroalkyl-substituted benzidine with respect to the total amount of the diamine component of the polyimide is preferably 50 mol% or more.
- perfluoroalkyl-substituted benzidine such as 2,2'-bis(trifluoromethyl)benzidine is preferred.
- the degree of acetyl substitution of the acetylcellulose-based resin may be 2.4 or more.
- the film of one embodiment of the present invention has a thickness of 5 ⁇ m or more and 300 ⁇ m or less, a total light transmittance of 85% or more, a haze of 10% or less, a yellowness of 5.0 or less, and a 1% weight loss temperature of 275 ° C. That's it.
- the polyimide resin and acetylcellulose resin contained in the resin composition show compatibility, a transparent film with a small haze can be obtained.
- the polyimide resin and the acetylcellulose resin show compatibility, coloring can be reduced while maintaining the excellent heat resistance of the polyimide, and a transparent film suitable for the cover film of a display can be produced.
- One embodiment of the present invention is a compatible resin composition containing a polyimide resin and an acetylcellulose resin.
- Polyimide is obtained by dehydrating and cyclodehydrating polyamic acid obtained by addition polymerization of tetracarboxylic dianhydride (hereinafter sometimes referred to as "acid dianhydride”) and diamine. That is, polyimide is a polycondensation product of tetracarboxylic dianhydride and diamine, and has an acid dianhydride-derived structure (acid dianhydride component) and a diamine-derived structure (diamine component).
- the polyimide used in the present embodiment is soluble in an organic solvent, and it is particularly preferred that the polyimide is soluble in an organic solvent (methylene chloride, etc.) capable of dissolving the acetylcellulose resin.
- organic solvent methylene chloride, etc.
- the polyimide used in this embodiment contains an alicyclic tetracarboxylic dianhydride as an acid dianhydride component.
- the alicyclic structure of the acid dianhydride component tends to improve the compatibility between the polyimide resin and the acetylcellulose resin.
- the alicyclic tetracarboxylic dianhydride should just have at least one alicyclic structure, and may have both an alicyclic ring and an aromatic ring in one molecule.
- the alicyclic ring may be polycyclic and may have a spiro structure.
- the alicyclic tetracarboxylic dianhydrides include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,3-dimethyl cyclobutane-1,2,3,4-tetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, 1,2,3,4-butanetetracarboxylic dianhydride, meso-butane-1,2,3,4-tetracarboxylic dianhydride, 1,1′- Bicyclohexane-3,3',4,4'tetracarboxylic acid-3,4:3',4'-dianhydride, norbornane-2-spiro- ⁇ -cyclopentanone- ⁇ '-spiro-2′′-
- 1,2,3,4-cyclobutanetetracarboxylic dianhydride CBDA
- 1,2,3,4- Cyclopentanetetracarboxylic dianhydride CPDA
- 1,2,4,5-cyclohexanetetracarboxylic dianhydride H-PMDA
- 1,1'-bicyclohexane-3,3',4,4' Tetracarboxylic acid-3,4:3′,4′-dianhydride H-PMDA or CBDA is preferred, with H-PMDA or CBDA being particularly preferred.
- the content of the alicyclic tetracarboxylic dianhydride relative to the total amount of 100 mol% of the acid dianhydride component is preferably 10 mol% or more, and 20 mol%.
- the above is more preferable, and 30 mol% or more is more preferable, and it may be 35 mol% or more, 40 mol% or more, 45 mol% or more, 50 mol% or more, 55 mol% or more, or 60 mol% or more.
- Polyimides with a large proportion of alicyclic tetracarboxylic dianhydride in the acid dianhydride component tend to absorb less light in the short wavelength to ultraviolet region of visible light, have excellent transparency, and have excellent light resistance.
- the polyimide resin exhibits high solubility in organic solvents even when the proportion of the alicyclic tetracarboxylic dianhydride is large. , tend to be excellent in compatibility with acetyl cellulose resins.
- the polyimide may contain an acid dianhydride other than the alicyclic tetracarboxylic dianhydride as the acid dianhydride component.
- an acid dianhydride other than the alicyclic tetracarboxylic dianhydride as the acid dianhydride component.
- fluorine-containing aromatic tetracarboxylic acids are used as acid dianhydride components. It may contain one or more selected from the group consisting of acid dianhydrides, bis(trimellitic anhydride) esters and diphthalic anhydrides having an ether bond.
- Fluorine-containing aromatic tetracarboxylic dianhydrides include 2,2-bis(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropane dianhydride, 2,2 -Bis ⁇ 4-[4-(1,2-dicarboxy)phenoxy]phenyl ⁇ -1,1,1,3,3,3-hexafluoropropane dianhydride and the like.
- a bis(trimellitic anhydride) ester is represented by the following general formula (1).
- X in general formula (1) is an arbitrary divalent organic group, and a carboxy group and a carbon atom of X are bonded at both ends of X.
- the carbon atoms attached to the carboxy group may form a ring structure.
- Specific examples of the divalent organic group X include the following (A) to (K).
- R 1 in formula (A) is a fluorine atom, an alkyl group having 1 to 20 carbon atoms, or a fluoroalkyl group having 1 to 20 carbon atoms, and m is an integer of 0 to 4.
- the group represented by formula (A) is a group obtained by removing two hydroxyl groups from a hydroquinone derivative which may have a substituent on the benzene ring.
- Hydroquinones having a substituent on the benzene ring include tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone and the like.
- the bis(trimellitic anhydride) ester is p-phenylene bis( trimellitate anhydride) (abbreviation: TAHQ).
- R 2 in formula (B) is a fluorine atom, an alkyl group having 1 to 20 carbon atoms, or a fluoroalkyl group having 1 to 20 carbon atoms, and n is an integer of 0-4.
- the group represented by formula (B) is a group obtained by removing two hydroxyl groups from biphenol which may have a substituent on the benzene ring.
- Biphenol derivatives having a substituent on the benzene ring include 2,2′-dimethylbiphenyl-4,4′-diol, 3,3′-dimethylbiphenyl-4,4′-diol, 3,3′,5, 5'-tetramethylbiphenyl-4,4'-diol, 2,2',3,3',5,5'-hexamethylbiphenyl-4,4'-diol and the like.
- the group represented by formula (C) is a group obtained by removing two hydroxyl groups from 4,4'-isopropylidenediphenol (bisphenol A).
- the group represented by formula (D) is a group obtained by removing two hydroxyl groups from resorcinol.
- p in formula (E) is an integer from 1 to 10.
- the group represented by formula (E) is a straight-chain diol having 1 to 10 carbon atoms from which two hydroxyl groups have been removed. Examples of linear diols having 1 to 10 carbon atoms include ethylene glycol and 1,4-butanediol.
- the group represented by formula (F) is a group obtained by removing two hydroxyl groups from 1,4-cyclohexanedimethanol.
- R 3 in formula (G) is a fluorine atom, an alkyl group having 1 to 20 carbon atoms, or a fluoroalkyl group having 1 to 20 carbon atoms, and q is an integer of 0-4.
- the group represented by formula (G) is a group obtained by removing two hydroxyl groups from bisphenolfluorene which may have a substituent on the benzene ring having a phenolic hydroxyl group. Examples of the bisphenol fluorene derivative having a substituent on the benzene ring having a phenolic hydroxyl group include biscresol fluorene.
- the bis(trimellitic anhydride) ester is preferably an aromatic ester.
- X is preferably (A), (B), (C), (D), (G), (H), or (I).
- (A) to (D) are preferred, and (B) a group having a biphenyl skeleton is particularly preferred.
- X is a group represented by the general formula (B)
- X is 2,2',3,3' represented by the following formula (B1) , 5,5′-hexamethylbiphenyl-4,4′-diyl.
- the acid dianhydride in which X in the general formula (1) is a group represented by the formula (B1) is bis(1,3-dioxo-1,3-dihydroisobenzofuran represented by the following formula (3) -5-carboxylic acid)-2,2′,3,3′,5,5′-hexamethylbiphenyl-4,4′-diyl (abbreviation: TAHMBP).
- Diphthalic anhydrides having an ether bond include 3,4'-oxydiphthalic anhydride, 4,4'-oxydiphthalic anhydride, and 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride. things, etc. 4'-(4,4'-Isopropylidenediphenoxy)diphthalic anhydride (BPADA) is particularly preferable from the viewpoint of solubility of the polyimide resin and compatibility with the acetylcellulose resin.
- BPADA 4,4'-(4,4'-Isopropylidenediphenoxy)diphthalic anhydride
- the total content of tetracarboxylic dianhydride, bis(trimellitic anhydride) ester and diphthalic anhydride having an ether bond is preferably 50 mol% or more, more preferably 60 mol% or more, and 65 mol% or more. is more preferable, and may be 70 mol% or more, 75 mol% or more, 80 mol% or more, 85 mol% or more, 90 mol% or more, or 95 mol% or more.
- Polyimide contains acid dianhydride components other than alicyclic tetracarboxylic dianhydride, fluorine-containing aromatic tetracarboxylic dianhydride, bis(trimellitic anhydride) ester and diphthalic anhydride having an ether bond. It may contain an acid dianhydride.
- acid dianhydrides other than the above include ethylenetetracarboxylic dianhydride, butanetetracarboxylic dianhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, and 2,2′.
- the polyimide used in this embodiment contains a fluoroalkyl-substituted benzidine as a diamine-derived structure. Having a fluoroalkyl-substituted benzidine in the diamine-derived structure tends to achieve both the solubility and transparency of the polyimide resin.
- fluoroalkyl-substituted benzidines examples include 2-(trifluoromethyl)benzidine, 3-(trifluoromethyl)benzidine, 2,3-bis(trifluoromethyl)benzidine, 2,5-bis(trifluoromethyl)benzidine , 2,6-bis(trifluoromethyl)benzidine, 2,3,5-tris(trifluoromethyl)benzidine, 2,3,6-tris(trifluoromethyl)benzidine, 2,3,5,6-tetrakis (trifluoromethyl)benzidine, 2,2′-bis(trifluoromethyl)benzidine, 3,3′-bis(trifluoromethyl)benzidine, 2,3′-bis(trifluoromethyl)benzidine, 2,2′ , 3-bis (trifluoromethyl) benzidine, 2,3,3'-tris (trifluoromethyl) benzidine, 2,2',5-tris (trifluoromethyl) benzidine, 2,2',6-tris ( trifluoromethyl)benzidine, 2,
- fluoroalkyl-substituted benzidine having a fluoroalkyl group at the 2-position of biphenyl is preferred, and 2,2'-bis(trifluoromethyl)benzidine (hereinafter referred to as "TFMB”) is particularly preferred.
- TFMB 2,2'-bis(trifluoromethyl)benzidine
- the content of the fluoroalkyl-substituted benzidine relative to 100 mol% of the total amount of the diamine component is preferably 50 mol% or more, more preferably 60 mol% or more, still more preferably 70 mol% or more, 80 mol% or more, 85 mol% or more, or 90 mol% or more. It may be mol% or more.
- a high content of fluoroalkyl-substituted benzidine tends to suppress coloration of the film and increase heat resistance.
- the polyimide may contain a diamine other than fluoroalkyl-substituted benzidine as a diamine component.
- diamines other than fluoroalkyl-substituted benzidine include p-phenylenediamine, m-phenylenediamine, o-phenylenediamine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether.
- diaminodiphenylsulfone as the diamine in addition to the fluoroalkyl-substituted benzidine
- solubility and transparency of the polyimide resin in solvents may be improved.
- diaminodiphenylsulfones 3,3'-diaminodiphenylsulfone (3,3'-DDS) and 4,4'-diaminodiphenylsulfone (4,4'-DDS) are preferred. 3,3'-DDS and 4,4'-DDS may be used in combination.
- the content of diaminodiphenylsulfone relative to 100 mol% of the total amount of diamine may be 1 to 40 mol%, 3 to 30 mol%, or 5 to 25 mol%.
- a polyamic acid is obtained as a polyimide precursor by reacting an acid dianhydride and a diamine, and a polyimide is obtained by cyclodehydration (imidization) of the polyamic acid.
- a polyimide is obtained by cyclodehydration (imidization) of the polyamic acid.
- the composition of the polyimide that is, the types and ratios of the acid dianhydride and the diamine
- the polyimide has transparency and solubility in organic solvents, as well as compatibility with the acetyl cellulose resin. indicates
- the method for preparing polyamic acid is not particularly limited, and any known method can be applied.
- acid dianhydride and diamine are dissolved in approximately equimolar amounts (molar ratio of 95:100 to 105:100) in an organic solvent and stirred to obtain a polyamic acid solution.
- concentration of the polyamic acid solution is usually 5-35% by weight, preferably 10-30% by weight. When the concentration is within this range, the polyamic acid obtained by polymerization has an appropriate molecular weight and the polyamic acid solution has an appropriate viscosity.
- a method of adding an acid dianhydride to a diamine is preferable in order to suppress the ring opening of the acid dianhydride.
- they may be added at once or may be added in multiple batches.
- Various physical properties of the polyimide can also be controlled by adjusting the addition order of the monomers.
- the organic solvent used for polyamic acid polymerization is not particularly limited as long as it does not react with diamines and acid dianhydrides and can dissolve polyamic acid.
- organic solvents include urea-based solvents such as methylurea and N,N-dimethylethylurea; sulfoxide or sulfone-based solvents such as dimethylsulfoxide, diphenylsulfone, and tetramethylsulfone; N,N-dimethylacetamide (DMAc); N-dimethylformamide (DMF), N,N'-diethylacetamide, N-methyl-2-pyrrolidone (NMP), ⁇ -butyrolactone, amide solvents such as hexamethylphosphoric triamide, halogenation such as chloroform and methylene chloride Examples include alkyl solvents, aromatic hydrocarbon solvents such as benzene and toluene, and ether solvents such as tetrahydrofuran, 1,
- Polyimide is obtained by dehydration cyclization of polyamic acid.
- a method for preparing a polyimide from a polyamic acid solution there is a method in which a dehydrating agent, an imidization catalyst, etc. are added to the polyamic acid solution and imidization proceeds in the solution.
- the polyamic acid solution may be heated to accelerate imidization.
- the polyimide resin is precipitated as a solid matter.
- a solvent suitable for film formation such as a low boiling point solvent, can be applied when preparing a solution for producing a film.
- the molecular weight of the polyimide (polyethylene oxide equivalent weight average molecular weight measured by gel filtration chromatography (GPC)) is preferably 10,000 to 300,000, more preferably 20,000 to 250,000, and 40,000 to 200,000 is more preferred. If the molecular weight is too small, the strength of the film may be insufficient. If the molecular weight is too large, the compatibility with the cellulose acetate resin may be poor.
- the polyimide is preferably soluble in low boiling point solvents such as ketone solvents and halogenated alkyl solvents. That polyimide exhibits solubility in a solvent means that it dissolves at a concentration of 5% by weight or more. In one embodiment, the polyimide exhibits solubility in methylene chloride. Since methylene chloride has a low boiling point and the residual solvent can be easily removed during film production, the use of a polyimide resin soluble in methylene chloride is expected to improve film productivity.
- polyimide preferably has low reactivity.
- the acid value of polyimide is preferably 0.4 mmol/g or less, more preferably 0.3 mmol/g or less, and even more preferably 0.2 mmol/g or less.
- the acid value of the polyimide may be 0.1 mmol/g or less, 0.05 mmol/g or less, or 0.03 mmol/g or less.
- the polyimide preferably has a high imidization rate. A low acid value tends to increase the stability of the polyimide and improve the compatibility with the acetylcellulose resin.
- acetylcellulose-based resin diacetylcellulose or triacetylcellulose having an acetyl group substitution degree of 2.0 to 3.0 is preferable.
- the degree of acetyl substitution of acetylcellulose is preferably 2.4 or more, and may be 2.5 or more, 2.6 or more, 2.7 or more, or 2.8 or more. good.
- the acetylcellulose-based resin may have a substituent other than the acetyl group as long as the degree of substitution of the acetyl group is within the above range.
- substituents other than the acetyl group include acyl groups such as propionyl group and butyryl group, and alkoxy groups such as methoxy group and ethoxy group.
- the glass transition temperature of the acetylcellulose resin is preferably 150°C or higher, and may be 160°C or higher or 170°C or higher.
- a resin composition is prepared by mixing the polyimide resin and the acetylcellulose resin. Since the polyimide resin and the acetylcellulose-based resin can exhibit compatibility at any ratio, the ratio of the polyimide resin and the acetylcellulose-based resin in the resin composition is not particularly limited.
- the mixing ratio (weight ratio) of the polyimide resin and the acetylcellulose resin may be 98:2-2:98, 95:5-10:90, or 90:10-15:85. There is a tendency that the higher the proportion of the polyimide resin, the better the heat resistance.
- the ratio of the acetylcellulose resin to the total of the polyimide and the acetylcellulose resin is preferably 10% by weight or more, more preferably 15% by weight. % or more, 20 wt % or more, 25 wt % or more, 30 wt % or more, 35 wt % or more, 40 wt % or more, 45 wt % or more, or 50 wt % or more.
- the resin composition may be a mixed solution containing a polyimide resin and an acetylcellulose resin.
- the method of mixing the resins is not particularly limited, and the resins may be mixed in a solid state or mixed in a liquid to form a mixed solution.
- a polyimide resin solution and an acetylcellulose-based resin solution may be separately prepared and mixed to prepare a mixed solution of a polyimide resin and an acetylcellulose-based resin.
- the solvent for the solution containing the polyimide resin and the acetylcellulose resin is not particularly limited as long as it exhibits solubility in both the polyimide resin and the acetylcellulose resin.
- solvents include amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methyl-2-pyrrolidone; ether solvents such as 1,4-dioxane and dioxolane; methylene chloride and chloroform. and halogenated alkyl solvents such as 1,1,2,2-tetrachloroethane.
- halogenated alkyl solvents are preferable because they have excellent solubility in both polyimide resins and acetylcellulose resins, have a low boiling point, and are easy to remove residual solvents during film production.
- the resin composition may be blended with organic or inorganic low-molecular-weight compounds, high-molecular-weight compounds (eg, epoxy resin), and the like.
- the resin composition may contain flame retardants, ultraviolet absorbers, cross-linking agents, dyes, pigments, surfactants, leveling agents, plasticizers, fine particles, sensitizers and the like.
- the fine particles include organic fine particles such as polystyrene and polytetrafluoroethylene, inorganic fine particles such as colloidal silica, carbon, and layered silicate, and the like, and may have a porous or hollow structure.
- Fiber reinforcements include carbon fibers, glass fibers, aramid fibers, and the like.
- Molding methods include melt methods such as injection molding, transfer molding, press molding, blow molding, inflation molding, calender molding, and melt extrusion molding.
- a resin composition containing polyimide and an acetylcellulose resin tends to have a lower melt viscosity than polyimide alone, and is excellent in moldability in injection molding, transfer molding, press molding, melt extrusion molding, and the like.
- the molded body is a film.
- the film forming method may be either a melt method or a solution method, but the solution method is preferred from the viewpoint of producing a film excellent in transparency and uniformity.
- a film is obtained by coating a support with a solution containing the polyimide resin and the acetylcellulose resin and removing the solvent by drying.
- a method for applying the resin solution onto the support a known method using a bar coater, a comma coater, or the like can be applied.
- a glass substrate, a metal substrate such as SUS, a metal drum, a metal belt, a plastic film, or the like can be used. From the viewpoint of improving productivity, it is preferable to use an endless support such as a metal drum, a metal belt, or a long plastic film as the support and to produce the film by roll-to-roll.
- a plastic film is used as the support, a material that does not dissolve in the solvent of the film-forming dope may be appropriately selected.
- the heating temperature is not particularly limited as long as the solvent can be removed and the coloration of the resulting film can be suppressed.
- the heating temperature may be increased stepwise.
- the resin film may be peeled off from the support and dried after drying has progressed to some extent. Heating under reduced pressure may be used to facilitate solvent removal.
- Acetylcellulose-based films may have low toughness, but the use of a compatible system of polyimide and acetylcellulose-based resin may improve the strength of the film.
- the film may be stretched in one direction or in multiple directions for the purpose of improving the mechanical strength of the film. When the film is stretched, the polymer chains are oriented in the stretching direction, so that the strength of the film in the in-plane direction is improved, and the occurrence of cracks and splits in the film tends to be suppressed.
- the thickness of the film is not particularly limited, and may be set appropriately according to the application.
- the thickness of the film is, for example, 5-300 ⁇ m. From the viewpoint of achieving both self-supporting property and flexibility and making a highly transparent film, the thickness of the film is preferably 10 ⁇ m to 100 ⁇ m, and may be 30 ⁇ m to 90 ⁇ m, 40 ⁇ m to 85 ⁇ m, or 50 ⁇ m to 80 ⁇ m. .
- the thickness of the film used as a cover film for displays is preferably 10 ⁇ m or more. When the film is stretched, the thickness after stretching is preferably within the above range.
- the haze of the film is preferably 10% or less, more preferably 5% or less, even more preferably 4% or less, and may be 3.5% or less, 3% or less, 2% or less, or 1% or less.
- the resin composition obtained by mixing polyimide and acetylcellulose resin preferably has a haze of 10% or less when a film having a thickness of 10 ⁇ m is produced.
- the total light transmittance (TT) of the film is preferably 85% or higher, more preferably 87% or higher, even more preferably 89% or higher, particularly preferably 90% or higher, and may be 91% or higher.
- the resin composition obtained by mixing polyimide and acetylcellulose resin preferably has a TT of 85% or more when a film having a thickness of 10 ⁇ m is produced.
- the transmittance of the film at 400 nm is preferably 50% or higher, more preferably 70% or higher, even more preferably 80% or higher, particularly preferably 85% or higher, and may be 90% or higher.
- the yellowness index (YI) of the film is preferably 5.0 or less, and may be 2.0 or less or 1.0 or less.
- YI yellowness index
- the resin composition obtained by mixing polyimide and acetylcellulose resin preferably has a YI of 5.0 or less when a film having a thickness of 10 ⁇ m is produced.
- the film has a small increase in yellowness ⁇ YI in a light resistance test.
- the increase in yellowness ⁇ YI of the film after a light resistance test in which the film is irradiated with ultraviolet light at an irradiance of 530 W/m 2 and a black panel temperature of 63° C. with a cumulative irradiation amount of 40.0 MJ/m 2 is preferably 6.0 or less. It is more preferably 5.0 or less, and may be 4.0 or less, 3.0 or less, 2.0 or less, 1.5 or less, or 1.0 or less.
- the yellowness index YI of the film after the light resistance test is preferably 8.0 or less, more preferably 7.0 or less, 6.0 or less, 5.0 or less, 4.0 or less, 3.0 or less, 2.0 or less. It may be 0 or less or 1.0 or less.
- the YI of the film tends to be smaller than in the case of polyimide resin alone, and ⁇ YI also tends to be smaller. Also, the larger the ratio of the alicyclic acid dianhydride in the acid dianhydride component of the polyimide, the smaller the YI of the film and the smaller the ⁇ YI.
- the 1% weight loss temperature (Td1) of the film is preferably 275°C or higher, more preferably 280°C or higher, even more preferably 290°C or higher, and may be 300°C or higher.
- the 5% weight loss temperature (Td5) of the film is preferably 320°C or higher, more preferably 330°C or higher, even more preferably 340°C or higher, and may be 345°C or higher.
- a film formed from a resin composition containing polyimide and an acetylcellulose resin is less colored and highly transparent, so it is suitable for use as a display material.
- films with high mechanical strength can be applied to surface members such as display cover windows.
- the film of the present invention may be provided with an antistatic layer, an easy-adhesion layer, a hard coat layer, an antireflection layer, and the like on the surface.
- IPA 2-propyl alcohol
- ⁇ Light resistance> Using a fade meter M6T manufactured by Suga Test Instruments Co., Ltd., a light resistance test was performed by irradiating until the cumulative irradiation dose reached 40.0 MJ/m 2 under the conditions of an irradiance of 530 W/m 2 and a black panel temperature of 63°C. The YI of the film before and after the light resistance test was measured, and the YI increment ⁇ YI after the weather resistance test was transferred to three types.
- a 1% weight loss temperature (Td1) and a 5% weight loss temperature (Td5) were measured using a simultaneous differential thermal thermogravimetry device (“STA7200” manufactured by Hitachi High-Tech Science). The measurement was performed by weighing 10 mg of the film and increasing the temperature from 30° C. to 400° C. at 10° C./min. Taking the weight at 200° C. as 100%, the temperature at which the weight first fell below 99% was Td1, and the temperature at which the weight first fell below 95% was Td5.
- Table 1 shows the compositions of the resins of Examples 1 to 3, Comparative Example 1 and Reference Example 4 (the composition of the polyimide and the mixing ratio with the triacetyl cellulose resin) and the evaluation results of the films.
- the polyimide film of Reference Example 1 which was produced using only the same polyimide resin as that used in Example 1, had a total light transmittance (TT) of 91.7%, whereas the polyimide resin and triacetyl
- the film of Example 1 which was produced using the composition containing the cellulose resin at a weight ratio of 50:50, had a TT of 92.0% and was excellent in transparency.
- the polyimide film of Reference Example 1 had a yellowness increase ⁇ YI of 1.4 after the weather resistance test, while the film of Example 1 had a ⁇ YI of 0.4. It can be seen that the film of No. 1 is excellent in light resistance in addition to transparency.
- the TT of the polyimide film of Reference Example 2 was 91.5%, while the TT of the film of Example 2 was 91.7%.
- the TT of the polyimide film of Reference Example 3 was 90.7%, while the TT of the film of Example 3 was 91.2%.
- the ⁇ YI of the polyimide film of Reference Example 2 was 3.6%, while the ⁇ YI of the film of Example 2 was 1.7.
- the ⁇ YI of the polyimide film of Reference Example 3 was 12.3%, while the ⁇ YI of the film of Example 3 was 5.6. From these results, it can be seen that in Examples 2 and 3 as well, the compatible resin composition of polyimide and acetylcellulose-based resin has superior light resistance to polyimide alone.
- the films of Examples 1 to 3 had higher Td1 and Td5 than the triacetyl cellulose film of Reference Example 4, and had excellent heat resistance.
- Comparative Example 1 in which a polyimide containing no alicyclic tetracarboxylic dianhydride was used as the tetracarboxylic dianhydride component, the compatibility between the polyimide and triacetyl cellulose was low, resulting in a significant increase in haze.
- a polyimide containing an alicyclic tetracarboxylic dianhydride as a tetracarboxylic dianhydride component exhibits compatibility with an acetylcellulose resin, and by using a resin composition in which these are mixed, It can be seen that a film having high transparency and excellent light resistance and heat resistance can be obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
La présente invention concerne une composition de résine comprenant un polyimide et une résine acrylique, le polyimide comprenant un dianhydride tétracarboxylique alicyclique en tant qu'au moins une partie d'un composant dianhydride tétracarboxylique et d'une benzidine substituée par un fluoroalkyle en tant que composant diamine. La quantité de dianhydride tétracarboxylique alicyclique peut être de 10 à 100 % en moles par rapport à l'ensemble du composant dianhydride tétracarboxylique du polyimide. Le degré de substitution acétyle d'une résine à base d'acétylcellulose peut être supérieur ou égal à 2,4. La composition de résine peut comprendre le polyimide et la résine à base d'acétylcellulose dans un rapport pondéral dans la plage de 98:2 à 2:98.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022015846 | 2022-02-03 | ||
JP2022-015846 | 2022-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023149435A1 true WO2023149435A1 (fr) | 2023-08-10 |
Family
ID=87552493
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2023/003097 WO2023149435A1 (fr) | 2022-02-03 | 2023-01-31 | Composition de résine, objet moulé et film |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2023149435A1 (fr) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005015629A (ja) * | 2003-06-26 | 2005-01-20 | Mitsubishi Gas Chem Co Inc | 溶媒可溶性ポリイミドの製造方法 |
JP2008045054A (ja) * | 2006-08-18 | 2008-02-28 | New Japan Chem Co Ltd | 脂環系ポリイミド共重合体及びその製造方法 |
WO2012133143A1 (fr) * | 2011-03-31 | 2012-10-04 | 三井化学株式会社 | Film composite de microparticules de résine de type polyimide et utilisation de ce dernier |
JP2018028694A (ja) * | 2012-12-12 | 2018-02-22 | 日産化学工業株式会社 | 組成物及び樹脂皮膜 |
WO2018225825A1 (fr) * | 2017-06-08 | 2018-12-13 | 日産化学株式会社 | Procédé de fabrication de substrat pour dispositif flexible |
JP2019023249A (ja) * | 2015-12-11 | 2019-02-14 | コニカミノルタ株式会社 | ポリイミドフィルム、フレキシブルプリント基板、led照明装置及びフレキシブルディスプレイ用前面部材 |
-
2023
- 2023-01-31 WO PCT/JP2023/003097 patent/WO2023149435A1/fr unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005015629A (ja) * | 2003-06-26 | 2005-01-20 | Mitsubishi Gas Chem Co Inc | 溶媒可溶性ポリイミドの製造方法 |
JP2008045054A (ja) * | 2006-08-18 | 2008-02-28 | New Japan Chem Co Ltd | 脂環系ポリイミド共重合体及びその製造方法 |
WO2012133143A1 (fr) * | 2011-03-31 | 2012-10-04 | 三井化学株式会社 | Film composite de microparticules de résine de type polyimide et utilisation de ce dernier |
JP2018028694A (ja) * | 2012-12-12 | 2018-02-22 | 日産化学工業株式会社 | 組成物及び樹脂皮膜 |
JP2019023249A (ja) * | 2015-12-11 | 2019-02-14 | コニカミノルタ株式会社 | ポリイミドフィルム、フレキシブルプリント基板、led照明装置及びフレキシブルディスプレイ用前面部材 |
WO2018225825A1 (fr) * | 2017-06-08 | 2018-12-13 | 日産化学株式会社 | Procédé de fabrication de substrat pour dispositif flexible |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6921758B2 (ja) | ポリアミド酸、ポリイミド、ポリアミド酸溶液、ポリイミド積層体、フレキシブルデバイス基板、及びそれらの製造方法 | |
WO2020004236A1 (fr) | Résine de polyimide, procédé de production de résine de polyimide, film de polyimide, et procédé de production de film de polyimide | |
KR102009067B1 (ko) | 폴리아미드산, 폴리이미드, 폴리아미드산 용액 및 폴리이미드의 이용 | |
JP2019506478A (ja) | 接着力が向上したポリアミック酸組成物及びこれを含むポリイミドフィルム | |
JP7510414B2 (ja) | ポリイミド樹脂およびその製造方法、ならびにポリイミドフィルムおよびその製造方法 | |
JP2016204569A (ja) | ポリアミック酸溶液組成物およびポリイミドフィルム | |
JPWO2019073972A1 (ja) | ポリイミド樹脂およびその製造方法、ポリイミド溶液、ならびにポリイミドフィルムおよびその製造方法 | |
WO2021132279A1 (fr) | Composition de résine et film | |
JP2013028688A (ja) | 製膜性が改善されたポリイミド樹脂及び光学フィルム | |
JP2017137443A (ja) | ポリイミド、ポリイミド溶液、ポリイミドフィルムおよびポリイミドフィルムを含有するプラスチック基板材料 | |
US20240199878A1 (en) | Resin composition, formed article and film | |
JP7356895B2 (ja) | 透明ポリイミド樹脂を含む光学フィルム並びにその製造方法 | |
WO2020262295A1 (fr) | Film de polyimide transparent et son procédé de production | |
KR20200092628A (ko) | 폴리아미드계 (공)중합체의 제조방법, 및 이를 이용한 폴리아미드계 (공)중합 수지 조성물, 고분자 필름 | |
WO2023149435A1 (fr) | Composition de résine, objet moulé et film | |
WO2023100806A1 (fr) | Film, son procédé de production et dispositif d'affichage d'image | |
WO2023085325A1 (fr) | Composition de résine, corps moulé et film | |
JP2006091310A (ja) | 光学フィルム、偏光板および液晶ディスプレイ | |
WO2023132310A1 (fr) | Composition de résine, corps moulé et film | |
WO2022124195A1 (fr) | Résine de polyimide, film de polyimide et procédé de fabrication s'y rapportant | |
JP2023086071A (ja) | 樹脂組成物およびフィルム | |
JPWO2019073628A1 (ja) | ポリイミド樹脂およびその製造方法、ポリイミド溶液、ならびにポリイミドフィルムおよびその製造方法 | |
JP2022163253A (ja) | 光学フィルム | |
JP2024043439A (ja) | 樹脂組成物、成形体およびフィルム | |
JP2023073709A (ja) | 樹脂組成物およびフィルム |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23749751 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2023578568 Country of ref document: JP Kind code of ref document: A |