JP5108851B2 - スルホン化ポリエーテルエーテルケトンケトン、これを用いたフィルム、およびその作製方法 - Google Patents
スルホン化ポリエーテルエーテルケトンケトン、これを用いたフィルム、およびその作製方法 Download PDFInfo
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- JP5108851B2 JP5108851B2 JP2009228399A JP2009228399A JP5108851B2 JP 5108851 B2 JP5108851 B2 JP 5108851B2 JP 2009228399 A JP2009228399 A JP 2009228399A JP 2009228399 A JP2009228399 A JP 2009228399A JP 5108851 B2 JP5108851 B2 JP 5108851B2
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- Prior art keywords
- film
- ketone
- bond compound
- double bond
- polyether ether
- Prior art date
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- 239000004696 Poly ether ether ketone Substances 0.000 title claims description 8
- 150000002576 ketones Chemical class 0.000 title claims description 8
- 229920002530 polyetherether ketone Polymers 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003999 initiator Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 9
- 230000008961 swelling Effects 0.000 description 9
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 benzyl dimethyl ketal Chemical compound 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229920001643 poly(ether ketone) Polymers 0.000 description 4
- 229920001657 poly(etheretherketoneketone) Polymers 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003014 ion exchange membrane Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012028 Fenton's reagent Substances 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical class CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000807 solvent casting Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- CCNDOQHYOIISTA-UHFFFAOYSA-N 1,2-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1C(C)(C)OOC(C)(C)C CCNDOQHYOIISTA-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- CJDPTOSHLLCQCD-UHFFFAOYSA-N 3,6-bis(tert-butylperoxy)-3,6-dimethylcyclohexyne Chemical compound CC(C)(C)OOC1(C)CCC(C)(OOC(C)(C)C)C#C1 CJDPTOSHLLCQCD-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- PTKHNBWCIHXVFS-UHFFFAOYSA-N 4-[2-methyl-1-(4-methylsulfanylphenyl)propan-2-yl]morpholine Chemical compound C1=CC(SC)=CC=C1CC(C)(C)N1CCOCC1 PTKHNBWCIHXVFS-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WWAAJQCSINIZFH-UHFFFAOYSA-N C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C.C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C Chemical compound C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C.C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C WWAAJQCSINIZFH-UHFFFAOYSA-N 0.000 description 1
- JWUVYEFYJPOHMO-UHFFFAOYSA-N N(=NC(C(=O)NCC=C)(C)C)C(C(=O)NCC=C)(C)C.N(=NC(C(=O)NCC=C)(C)C)C(C(=O)NCC=C)(C)C Chemical compound N(=NC(C(=O)NCC=C)(C)C)C(C(=O)NCC=C)(C)C.N(=NC(C(=O)NCC=C)(C)C)C(C(=O)NCC=C)(C)C JWUVYEFYJPOHMO-UHFFFAOYSA-N 0.000 description 1
- KBODBABLOCQNAU-UHFFFAOYSA-N N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C.N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C Chemical compound N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C.N(=NC(C(=O)NCCCC)(C)C)C(C(=O)NCCCC)(C)C KBODBABLOCQNAU-UHFFFAOYSA-N 0.000 description 1
- JIKLBERNNOSYTO-UHFFFAOYSA-N N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N Chemical compound N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N JIKLBERNNOSYTO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- PISLKPDKKIDMQT-UHFFFAOYSA-N [3-(4-fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1 PISLKPDKKIDMQT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- MGZTXXNFBIUONY-UHFFFAOYSA-N hydrogen peroxide;iron(2+);sulfuric acid Chemical compound [Fe+2].OO.OS(O)(=O)=O MGZTXXNFBIUONY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- JFXDYPLHFRYDJD-UHFFFAOYSA-M sodium;6,7-dihydroxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=C2C=C(O)C(O)=CC2=C1 JFXDYPLHFRYDJD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0006—Organic membrane manufacture by chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/52—Polyethers
- B01D71/522—Aromatic polyethers
- B01D71/5222—Polyetherketone, polyetheretherketone, or polyaryletherketone
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
- C08G65/4056—(I) or (II) containing sulfur
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
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- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1025—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having only carbon and oxygen, e.g. polyethers, sulfonated polyetheretherketones [S-PEEK], sulfonated polysaccharides, sulfonated celluloses or sulfonated polyesters
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1081—Polymeric electrolyte materials characterised by the manufacturing processes starting from solutions, dispersions or slurries exclusively of polymers
-
- H—ELECTRICITY
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- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1086—After-treatment of the membrane other than by polymerisation
- H01M8/1088—Chemical modification, e.g. sulfonation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/34—Use of radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/24—Mechanical properties, e.g. strength
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/30—Chemical resistance
-
- 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
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0065—Solid electrolytes
- H01M2300/0082—Organic polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1037—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having silicon, e.g. sulfonated crosslinked polydimethylsiloxanes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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Description
本出願は、出願日を2008年12月26日とする台湾特許出願第097150829号の優先権を主張するものであり、その全体がここに参照として組み入れられる。
本発明はプロトン交換膜に関し、より詳細にはプロトン交換膜の膨潤度および寸法安定性を改善するための組成および処方に関する。
式4に示すように、p−ベンゾキノンをジクロロメタン中に溶解し、再結晶させて精製した。精製したp−ベンゾキノン(200mmol)21.62gをメタノール(95%)500mL中に溶解してから、−78℃でシクロペンタジエン(260mmol)17.55mLをゆっくり加えた。続いてその混合物を、−78℃からゆっくり攪拌しながら室温にし、次いで室温で8時間反応させてから、メタノールで再結晶し、31.36gの生成物を得た(収率90%)。式4の生成物の水素スペクトルは次のとおりであった。1H NMR(200MHz in CDCl3): δ1.23−1.26(dd,1H)、1.37−1.40(dd,1H)、3.18 (s,2H)、3.51(s,2H)、6.02(s,2H)、6.53 (s,2H,CH=CH)。
1,3−ビス(4−フルオロベンゾイル)ベンゼン(1,3-bis(4-fluorobenzoyl)benzene)(5.70mmol、アルドリッチ社より購入)1.85g、2,3−ジヒドロキシ−ナフタレン−6−スルホン酸モノナトリウム塩(2,3-dihydroxy-naphthalene-6-sulfonic acid monosodium salt)(5.14mmol、TCIより購入)1.35g、実施例1における式6のシクロアルケニルジオール生成物(0.57mmol)0.1g、および炭酸カリウム(8.61mmol)1.19gをN−メチル−2−ピロリドン(NMP)10mLおよびトルエン10mLの共溶媒(co-solvent)に溶解した。その溶液を、160℃に加熱して4時間反応させた後、トルエンを留去した。そのNMP溶液を175℃に加熱して48時間反応させた。重合後、室温でメタノール100mLを加え、赤紫色(purple red)の固体を沈殿させろ過した。そのろ過ケーキ(filtered cake)を蒸留水およびメタノールで数回洗浄してから、真空オーブンで乾燥させて2.85gの生成物を得た(収率86%)。上述の反応は式7に示すとおりであり、式中のaおよびbのモル比はa:bの比で9:1である。式7の生成物の水素スペクトルは次のとおりであった。1H NMR(300MHz in DMSO−d6): δ8.18(s,1H)a、7.84−7.97(m,6H)、7.57−7.72(m,6H)、7.04(s,4H)、6.82(s,2H)b、6.72(s,2H)b、3.79(s,2H)b、2.15−2.20 (m, 2H)b。(注:aおよびbは、フェニルvs.シクロアルケニル部分(moieties)のモル比〜9:1を表す。)
実施例2のポリマー生成物(Na form)をNMPに溶解して10%NMP溶液を作った。そのNMP溶液に、開始剤として2wt%のAIBNを加え、溶媒キャスティングの方式によりガラス板上に滴下してから、勾配加熱(gradient heating)により溶媒をゆっくり揮発させて成膜させた。勾配加熱の工程は窒素環境下で進行し、かつ次に示すとおりに行った。つまり、85℃まで加熱して24時間ラジカル重合を進行させ、95℃まで加熱して6時間95℃に保ち、105℃まで加熱して6時間105℃に保ち、さらに120℃まで加熱して12時間真空引きし、フィルムを作った。
実施例2に類似する。実施例4で相違するのは、2,3−ジヒドロキシ−ナフタレン−6−スルホン酸モノナトリウム塩と実施例1における式6のシクロアルケニルジオール生成物とのモル比(a:b)を8:2にしたことのみである。
実施例2のSPEEKKポリマーをNMPに溶解して10%NMP溶液を作った。そのNMP溶液に、熱開始剤として2wt%のAIBNを加え、ガラス板上に滴下してから、勾配加熱により溶媒をゆっくり揮発させて成膜させた。勾配加熱の工程は窒素環境下で進行し、かつ次に示すとおりに行った。つまり、70℃まで加熱しAIBNを熱的に解裂することによりラジカルを生じさせてSPEEKKのシクロアルケニル基を12時間架橋反応させ、80℃まで加熱して6時間80℃に保ち、90℃まで加熱して6時間90℃に保ち、さらに110℃まで加熱して12時間真空引きすることで溶媒を除去し、フィルムの作製を完成させた。
実施例5と類似する。実施例6で相違するのは、そのSPEEKK生成物を、実施例2ではなくて、実施例4より得られたものとした点のみである。実施例6のAIBNの比率および加熱工程は実施例5と同様である。
実施例5に類似する。実施例7で相違するのは、AIBN熱開始剤を用いなかった点のみである。実施例7の加熱工程は実施例5と同様である。
実施例6に類似する。実施例8で相違するのは、AIBN熱開始剤を用いなかった点のみである。実施例8の加熱工程は実施例6と同様である。
実施例5から8のフィルムのイオン交換能(IEC)およびプロトン導電率を測定し、表1に示した。フィルムの寸法は5cm×5cm×0.01〜0.02cmとした。これらフィルムの室温でのプロトン導電率は10−2S/cm以上であった。図3に示されるように、実施例6のフィルムのプロトン導電率は7.52×10−2S/cmであり、かつ高湿・高温下でのプロトン導電率は0.2S/cmに近いものであった。実施例6のフィルムのスルホン化基(sulfonated group)の分解温度は205℃、ガラス転移温度(Tg)は226℃であった。
Claims (12)
- 請求項1または2に記載のスルホン化ポリエーテルエーテルケトンケトン、および
ラジカル開始剤、
を含むフィルム処方(film formula)。 - 前記ラジカル開始剤が、光開始剤または熱開始剤を含む請求項3に記載のフィルム処方。
- 二重結合化合物および/または三重結合化合物をさらに含む請求項3または4に記載のフィルム処方。
- 前記二重結合化合物が、シラン、ジビニルベンゼン、またはアルケニルオリゴマーを含む請求項5に記載のフィルム処方。
- フィルムの作製方法であって、
請求項3のフィルム処方を溶媒に溶かして溶液を作る工程、
前記溶液を基板上に形成し、エネルギーを与えて前記スルホン化ポリエーテルエーテルケトンケトンをラジカル架橋反応させる工程、および
前記溶媒を除去してフィルムを形成する工程、
を含む方法。 - 前記エネルギーが光または熱を含む請求項7に記載の方法。
- 前記溶液に二重結合化合物および/または三重結合化合物を加える工程をさらに含み、前記ラジカル架橋反応させる工程において、前記スルホン化ポリエーテルエーテルケトンケトン、前記二重結合化合物および/または前記三重結合化合物を前記エネルギーによりラジカル架橋反応させる請求項7に記載の方法。
- 請求項1のスルホン化ポリエーテルエーテルケトンケトンを架橋させた架橋物を含むフィルム。
- 前記架橋物は、二重結合化合物および/または三重結合化合物をさらに共架橋させてなるものである請求項10に記載のフィルム。
- 前記二重結合化合物が、シラン、ジビニルベンゼン、またはアルケニルオリゴマーを含む請求項11に記載のフィルム。
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TW097150829A TW201024333A (en) | 2008-12-26 | 2008-12-26 | Sulfonated polyether ether ketone ketone, film utilizing the same, and method for manufacturing the same |
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TWI437027B (zh) | 2011-12-29 | 2014-05-11 | Ind Tech Res Inst | 一種含有軟鏈段之馬來醯亞胺聚合物及其製備方法 |
CN109535284B (zh) * | 2017-07-31 | 2021-07-06 | 广东华润涂料有限公司 | 适用于uv-led光辐射的光引发剂组合物以及由其配制的水性涂料组合物 |
CN108047383B (zh) * | 2018-01-23 | 2020-03-17 | 中国科学院长春应用化学研究所 | 聚偏氟乙烯共聚物的制备方法 |
CN108752587B (zh) * | 2018-05-02 | 2020-12-25 | 福州大学 | 一种基于联萘酚的磺化聚芳醚酮砜化合物及其制备方法 |
US20210380771A1 (en) * | 2018-10-05 | 2021-12-09 | Rensselaer Polytechnic Institute | Preparation of ion exchange membranes from polyolefins and polycyclic olefins |
CN117683192A (zh) * | 2024-02-02 | 2024-03-12 | 沈阳柏曦高新材料科技有限公司 | 一种聚醚醚酮的合成方法 |
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US3661937A (en) * | 1968-04-17 | 1972-05-09 | Universal Oil Prod Co | 1,4-dihydroxypolyhalopolyhydro - 5,8-methano - 2,3 - naphthalenedicarboxylic acids and corresponding anhydrides |
US4240974A (en) * | 1970-10-14 | 1980-12-23 | Little Julian R | Fire retardant sulfonate compound |
US3716516A (en) * | 1971-11-08 | 1973-02-13 | R Dombro | Flame retardant compositions of matter |
US4459351A (en) * | 1983-06-22 | 1984-07-10 | Eastman Kodak Company | Photographic element and process employed combination of surface and internal latent image silver halide |
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US7291689B1 (en) * | 2006-05-01 | 2007-11-06 | Seoul National University Industry Foundation | Thermally stable low dielectric norbornene polymers with improved solubility and adhesion property |
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