JP6271824B2 - ポリアリレート樹脂およびそれからなるフィルム - Google Patents
ポリアリレート樹脂およびそれからなるフィルム Download PDFInfo
- Publication number
- JP6271824B2 JP6271824B2 JP2017553206A JP2017553206A JP6271824B2 JP 6271824 B2 JP6271824 B2 JP 6271824B2 JP 2017553206 A JP2017553206 A JP 2017553206A JP 2017553206 A JP2017553206 A JP 2017553206A JP 6271824 B2 JP6271824 B2 JP 6271824B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- general formula
- hydroxyphenyl
- mol
- polyarylate resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 229920005989 resin Polymers 0.000 title claims description 97
- 239000011347 resin Substances 0.000 title claims description 97
- 229920001230 polyarylate Polymers 0.000 title claims description 83
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 18
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 13
- BHWMWBACMSEDTE-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclododecyl]phenol Chemical group C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCCCCCCCC1 BHWMWBACMSEDTE-UHFFFAOYSA-N 0.000 claims description 6
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical group C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 description 48
- -1 halogen aromatic hydrocarbon Chemical class 0.000 description 45
- 239000003960 organic solvent Substances 0.000 description 38
- 150000002367 halogens Chemical class 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 230000005484 gravity Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 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 15
- 230000035699 permeability Effects 0.000 description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 239000003990 capacitor Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000005453 ketone based solvent Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 238000012695 Interfacial polymerization Methods 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000004210 ether based solvent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-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
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- LRRMGPGVHYPBPL-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 LRRMGPGVHYPBPL-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CSOQDRZGMGKOGN-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)-2-methylpropyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C(C)C)C1=CC(C(C)(C)C)=C(O)C=C1C CSOQDRZGMGKOGN-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- GRHWLIMQOFAGHA-UHFFFAOYSA-N dieticyclidine Chemical compound C=1C=CC=CC=1C1(N(CC)CC)CCCCC1 GRHWLIMQOFAGHA-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
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Description
<1> 一般式(1)で示される二価フェノール残基と、一般式(2)で示される芳香族二価カルボン酸残基を含むポリアリレート樹脂。
<2> 一般式(1)で示される二価フェノール残基が、1,1−ビス(4−ヒドロキシフェニル)シクロドデカン残基である<1>に記載のポリアリレート樹脂。
<3> 一般式(2)で示される芳香族二価カルボン酸残基が、ジフェニルエーテル−4,4’−ジカルボン酸残基である<1>または<2>に記載のポリアリレート樹脂。
<4> 一般式(1)で表される二価フェノール残基の含有量が、全二価フェノール成分に対して、10モル%以上である<1>〜<3>のいずれかに記載のポリアリレート樹脂。
<5> 一般式(2)で示される芳香族二価カルボン酸残基の含有量が、全芳香族二価カルボン酸成分に対して、70モル%以上である<1>〜<4>のいずれかに記載のポリアリレート樹脂。
<6> さらに一般式(3)で示されるビフェノール残基を含む<1>〜<3>のいずれかに記載のポリアリレート樹脂。
<7> 一般式(3)で示されるビフェノール残基の含有量が、全二価フェノール成分に対して、90モル%以下である<6>に記載のポリアリレート樹脂。
<8> さらに一般式(4)で示されるフタル酸残基を含む<1>〜<7>のいずれかに記載のポリアリレート樹脂。
<10> <1>〜<9>のいずれかに記載のポリアリレート樹脂からなるフィルム。
また、信号の伝送損失を小さくする観点から、ポリアリレート樹脂の誘電正接は1MHzにおいて0.02以下であることが好ましく、0.016以下であることがより好ましく)、0.012以下であることがさらに好ましい。ポリアリレート樹脂の誘電正接の下限値は特に限定されず、当該誘電正接は通常、0.001以上、特に0.004以上である。
また、靭性の観点からフィルムの引張破断伸びは20%以上であることが好ましく、25%以上であることがより好ましく、40%以上であることがさらに好ましい。フィルムの引張破断伸びの上限値は特に限定されず、当該引張破断伸びは通常、200%以下、特に100%以下である。
また、フィルムの引張弾性率は1.6GPa以上であることが好ましく、1.7GPa以上であることがより好ましく、1.8GPa以上であることがさらに好ましい。フィルムの引張弾性率の上限値は特に限定されず、当該引張弾性率は通常、3GPa以下、特に2.5GPa以下である。
ゲルパーミエーションクロマトグラフィー(GPC)を用いて、以下の条件でポリスチレン換算の数平均分子量および重量平均分子量を測定した。
送液装置:ウォーターズ社製、Isocratic HPLC Pump 1515
検出器:ウォーターズ社製、Refractive Index Detector 2414
カラム:Mixed−D(充填シリカゲル粒径5μm、チューブ長さ300mm、内径7.5mm)
溶媒:クロロホルム
流速:1mL/分
測定温度:35℃
ポリアリレート樹脂10mgをサンプルとして用いて、DSC(示差走査熱量測定)装置(パーキンエルマー社製、DSC7)を用いて昇温速度10℃/分の条件で昇温し、昇温曲線中のガラス転移に由来する2つの折曲点温度の中間値をガラス転移温度とした。
◎:275℃以上(最良)。
○:260℃以上275℃未満(良)。
△:240℃以上260℃未満(実用上問題なし)。
×:240℃未満(実用上問題あり)。)
ポリアリレート樹脂10〜15質量部にクロロホルム90〜85質量部を加えて樹脂溶液を得た。得られた樹脂溶液を用いて、PETフィルム上に塗膜を形成した。室温で風乾後、塗膜をPETフィルムから剥離し、減圧にて150℃で24時間乾燥して、厚さ100μmのフィルムを作製した。
得られたフィルムを用いて、JIS C 2138に準拠し、自動平衡ブリッジ法にて以下の条件で測定した。
装置:アジレント・テクノロジー株式会社製、プレシジョンLCRメータE4980A
試料寸法:長さ60mm×幅60mm×厚み100μm
周波数:1MHz
測定温度:23℃
電極寸法:主電極径φ36mm、環状電極内径φ38mm
電極材質:スズ箔貼付
試験環境:23℃±1℃、50%RH±5%RH
・比誘電率
◎:2.8以下(最良)。
○:2.8超2.85以下(良)。
△:2.85超2.9以下(実用上問題なし)。
×:2.9超(実用上問題あり)。
・誘電正接
◎:0.012以下(最良)。
○:0.012超0.016以下(良)。
△:0.016超0.02以下(実用上問題なし)。
×:0.02超(実用上問題あり)。
(3)で得られたフィルムを用いて、自動分光光度計(日立製作所製 U−4000型)を用いて、波長345nmにおける光線透過率を測定した。
◎:80%以上(最良)。
○:40%以上80%未満(良)。
△:20%以上40%未満(実用上問題なし)。
×:20%未満(実用上問題あり)。
(3)で得られたフィルムについて、多波長アッベ屈折計「DR−M2」(アタゴ社製)を用い、測定温度25℃、光源波長589nmで測定した。
◎:1.59以下(最良)。
○:1.59超1.60以下(良)。
△:1.60超1.61未満(実用上問題なし)。
×:1.61以上(実用上問題あり)。
(3)で得られたフィルムを用いてJIS K7127に準拠し、以下の条件で測定した。
試験装置:株式会社インテスコ製、Model2020
引張速度:50mm/分
試験環境:23℃、60%RH
・引張破断強さ
◎:100MPa以上(最良)。
○:80MPa以上100MPa未満(良)。
△:70MPa以上80MPa未満(実用上問題なし)。
×:70MPa未満(実用上問題あり)。
・引張破断伸び
◎:40%以上(最良)。
○:25%以上40%未満(良)。
△:20%以上25%未満(実用上問題なし)。
×:20%未満(実用上問題あり)。
・引張弾性率
◎:1.8GPa以上(最良)。
○:1.7GPa以上1.8GPa未満(良)。
△:1.6GPa以上1.7GPa未満(実用上問題なし)。
×:1.6GPa未満(実用上問題あり)。
ポリアリレート樹脂15質量部にキシレンまたはシクロヘキサノン85質量部を加えて、ウェーブローターを用いて室温で攪拌した。1日後の樹脂溶液の状態を以下の基準で評価した。
◎:樹脂溶液は流動性を有しており、非常に優れた透明性を示した(最良)。
○:樹脂溶液は流動性を有しており、優れた透明性を示した(良)。
△:樹脂溶液は流動性を有しており、樹脂は溶解していたが、白濁していた(実用上問題なし)。
×:樹脂溶液が流動性を有していなかったか、樹脂が全く溶解していなかった(実用上問題あり)。
(3)で得られたフィルムから1辺が5cmである正方形のサンプルを切り出し、電子天秤によりサンプルの重量を測定した。次に、厚み測定装置(ハイデンハイン社製)を用いて、サンプルの厚みを測定した。得られたサンプルの重量と厚みから、比重を求めた。
◎:1.15g/cm3以下(最良)。
○:1.15g/cm3超1.17g/cm3以下(良)。
△:1.17g/cm3超1.20g/cm3以下(実用上問題なし)。
×:1.20g/cm3超(実用上問題あり)。
攪拌装置を備えた反応容器中に、二価フェノール成分として1,1−ビス(4−ヒドロキシフェニル)シクロドデカン(PCDE)100.00質量部、末端封止剤としてp−tert−ブチルフェノール(PTBP)1.24質量部、アルカリとして水酸化ナトリウム(NaOH)172.6質量部、重合触媒としてトリ−n−ブチルベンジルアンモニウムクロライド(TBBAC)の50質量%水溶液を1.22質量部、酸化防止剤としてハイドロサルファイトナトリウム0.50質量部を仕込み、水2800質量部に溶解させた(水相)。また、これとは別に、塩化メチレン2200質量部に、ジフェニルエーテル−4,4’−ジカルボン酸クロリド(DEDC)84.92質量部を溶解させた(有機相)(PCDE:PTBP:DEDC:TBBAC:NaOH=98.57:2.86:100.00:0.68:1500(モル比))。水相をあらかじめ攪拌しておき、有機相を水相中に強攪拌下で添加し、15℃で2時間、界面重合法で重合をおこなった。この後、攪拌を停止し、水相と有機相をデカンテーションして分離した。水相を除去した後、塩化メチレン500質量部、純水3000質量部および酢酸10質量部を添加して反応を停止し、15℃で30分間攪拌した。その後、有機相を純水で10回洗浄し、有機相をメタノール中に添加してポリマーを沈殿させた。沈殿させたポリマーを濾過した後、150℃真空下で24時間乾燥し、ポリアリレート樹脂を得た。
表1に示すように、樹脂組成を変更する以外は実施例1と同様の操作をおこなって、ポリアリレート樹脂を得た。二価フェノールおよび二価カルボン酸クロライドの使用量はそれぞれ、モル数が実施例1における二価フェノールおよび二価カルボン酸クロライドのモル数と同様であるような量であった。
Claims (6)
- 二価フェノール残基および芳香族二価カルボン酸残基から構成され、
二価フェノール残基が一般式(1)で示される二価フェノール残基および一般式(3)で示されるビフェノール残基のみからなり、
芳香族二価カルボン酸残基が一般式(2)で示される芳香族二価カルボン酸残基のみからなり、
一般式(1)で表される二価フェノール残基の含有量が、全二価フェノール成分に対して、10モル%以上80モル%以下であり、
一般式(3)で示されるビフェノール残基の含有量が、全二価フェノール成分に対して、20モル%以上90モル%以下である、ポリアリレート樹脂。
- 二価フェノール残基および芳香族二価カルボン酸残基から構成され、
二価フェノール残基が一般式(1)で示される二価フェノール残基および一般式(3)で示されるビフェノール残基のみからなり、
芳香族二価カルボン酸残基が一般式(2)で示される芳香族二価カルボン酸残基および一般式(4)で示されるフタル酸残基のみからなり、
一般式(1)で表される二価フェノール残基の含有量が、全二価フェノール成分に対して、10モル%以上80モル%以下であり、
一般式(2)で示される芳香族二価カルボン酸残基の含有量が、全芳香族二価カルボン酸成分に対して、50モル%以上であり、
一般式(3)で示されるビフェノール残基の含有量が、全二価フェノール成分に対して、20モル%以上90モル%以下である、ポリアリレート樹脂。
- 一般式(1)で示される二価フェノール残基が、1,1−ビス(4−ヒドロキシフェニル)シクロドデカン残基である請求項1または2に記載のポリアリレート樹脂。
- 一般式(2)で示される芳香族二価カルボン酸残基が、ジフェニルエーテル−4,4’−ジカルボン酸残基である請求項1〜3のいずれかに記載のポリアリレート樹脂。
- 一般式(4)で示されるフタル酸残基の含有量が、全芳香族二価カルボン酸成分に対して、10モル%以上50モル%以下である請求項2に記載のポリアリレート樹脂。
- 請求項1〜5のいずれかに記載のポリアリレート樹脂からなるフィルム。
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