JP2008521999A5 - - Google Patents
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- JP2008521999A5 JP2008521999A5 JP2007544277A JP2007544277A JP2008521999A5 JP 2008521999 A5 JP2008521999 A5 JP 2008521999A5 JP 2007544277 A JP2007544277 A JP 2007544277A JP 2007544277 A JP2007544277 A JP 2007544277A JP 2008521999 A5 JP2008521999 A5 JP 2008521999A5
- Authority
- JP
- Japan
- Prior art keywords
- block
- group
- general formula
- precursors
- sulfonated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 102
- 239000012528 membrane Substances 0.000 claims description 86
- 229920001400 block copolymer Polymers 0.000 claims description 73
- 239000003792 electrolyte Substances 0.000 claims description 70
- 239000002243 precursor Substances 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 229920006030 multiblock copolymer Polymers 0.000 claims description 33
- 230000002209 hydrophobic effect Effects 0.000 claims description 31
- 239000000446 fuel Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000005518 polymer electrolyte Substances 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 239000011342 resin composition Substances 0.000 claims description 10
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 claims description 7
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- GIXNHONPKYUROG-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)phenol Chemical compound C1=CC(O)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C12 GIXNHONPKYUROG-UHFFFAOYSA-N 0.000 claims description 3
- QWQONZVLXJGXHV-UHFFFAOYSA-N [chlorosulfonyloxy(dimethyl)silyl]methane Chemical compound C[Si](C)(C)OS(Cl)(=O)=O QWQONZVLXJGXHV-UHFFFAOYSA-N 0.000 claims description 3
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 3
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- YDSGCMVPVMGPGG-UHFFFAOYSA-N 4-[(4-hydroxy-2,5-dimethylphenyl)methyl]-2,5-dimethylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C(=CC(O)=C(C)C=2)C)=C1C YDSGCMVPVMGPGG-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 238000004581 coalescence Methods 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 38
- 229920001577 copolymer Polymers 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 30
- 238000006277 sulfonation reaction Methods 0.000 description 30
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- -1 polytetrafluoroethylene Polymers 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 229920000557 Nafion® Polymers 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000035699 permeability Effects 0.000 description 8
- 229920005597 polymer membrane Polymers 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000010354 integration Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 0 Cc1ccc(*(C2)*2c2ccc(C)cc2)cc1 Chemical compound Cc1ccc(*(C2)*2c2ccc(C)cc2)cc1 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008378 aryl ethers Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20040105493 | 2004-12-14 | ||
| PCT/KR2005/004291 WO2006065068A1 (en) | 2004-12-14 | 2005-12-14 | Sulphonated multiblock copolymer and electrolyte membrane using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008521999A JP2008521999A (ja) | 2008-06-26 |
| JP2008521999A5 true JP2008521999A5 (https=) | 2011-07-28 |
Family
ID=36588089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007544277A Pending JP2008521999A (ja) | 2004-12-14 | 2005-12-14 | スルホン化マルチブロック共重合体及びこれを用いた電解質膜 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7601785B2 (https=) |
| EP (1) | EP1828284B1 (https=) |
| JP (1) | JP2008521999A (https=) |
| KR (1) | KR100756821B1 (https=) |
| CN (1) | CN101076551B (https=) |
| TW (1) | TWI294432B (https=) |
| WO (1) | WO2006065068A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI326691B (en) * | 2005-07-22 | 2010-07-01 | Kraton Polymers Res Bv | Sulfonated block copolymers, method for making same, and various uses for such block copolymers |
| US20080004443A1 (en) * | 2006-07-03 | 2008-01-03 | General Electric Company | Sulfonated polyaryletherketone-block-polyethersulfone copolymers |
| US20080231712A1 (en) * | 2007-03-22 | 2008-09-25 | Property Monitors, Inc. | Portable video acquisition and internet broadcast system |
| KR100843569B1 (ko) * | 2007-06-26 | 2008-07-03 | 연세대학교 산학협력단 | 수소이온 전도성 복합 트리블록 공중합체 전해질막 및 그제조방법 |
| JP2009091568A (ja) * | 2007-09-20 | 2009-04-30 | Sumitomo Chemical Co Ltd | 高分子電解質組成物 |
| US8440365B2 (en) * | 2008-01-08 | 2013-05-14 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Electrolyte, production process therefor, electrolyte membrane, production process therefor, catalyst layer and fuel cell |
| US8012539B2 (en) | 2008-05-09 | 2011-09-06 | Kraton Polymers U.S. Llc | Method for making sulfonated block copolymers, method for making membranes from such block copolymers and membrane structures |
| US8574664B2 (en) * | 2008-09-02 | 2013-11-05 | General Electric Company | Electrolyte membrane, methods of manufacture thereof and articles comprising the same |
| EP2345682B1 (en) * | 2008-11-04 | 2017-08-23 | LG Chem, Ltd. | Polymer electrolyte membrane |
| JP5590568B2 (ja) * | 2009-03-27 | 2014-09-17 | 国立大学法人山梨大学 | ブロック共重合体、およびその利用 |
| CN101531759B (zh) * | 2009-04-17 | 2011-03-30 | 南京林业大学 | 冰片烯聚砜树脂的制备方法 |
| US8445631B2 (en) | 2009-10-13 | 2013-05-21 | Kraton Polymers U.S. Llc | Metal-neutralized sulfonated block copolymers, process for making them and their use |
| US8263713B2 (en) | 2009-10-13 | 2012-09-11 | Kraton Polymers U.S. Llc | Amine neutralized sulfonated block copolymers and method for making same |
| US9429366B2 (en) | 2010-09-29 | 2016-08-30 | Kraton Polymers U.S. Llc | Energy recovery ventilation sulfonated block copolymer laminate membrane |
| US9394414B2 (en) | 2010-09-29 | 2016-07-19 | Kraton Polymers U.S. Llc | Elastic, moisture-vapor permeable films, their preparation and their use |
| BR112013007705A2 (pt) | 2010-10-18 | 2016-08-09 | Kraton Polymers Us Llc | solução tendo uma composição de copolímero em bloco sulfonado, película ou membrana, dispersão aquosa, compósito, composição de copolímeto em bloco sulfonado, processo, método para formar uma composição de copolímero em bloco sulfonado, e, célula eletrodialítica |
| US9861941B2 (en) | 2011-07-12 | 2018-01-09 | Kraton Polymers U.S. Llc | Modified sulfonated block copolymers and the preparation thereof |
| US8952109B2 (en) * | 2011-08-05 | 2015-02-10 | Basf Se | Process for preparing a block copolymer |
| EP2554564A1 (de) * | 2011-08-05 | 2013-02-06 | Basf Se | Verfahren zur Herstellung eines Blockcopolymers |
| TWI452063B (zh) * | 2012-03-29 | 2014-09-11 | Univ Nat Sun Yat Sen | 磺酸化聚芳香醚高分子及其製造方法 |
| KR101627930B1 (ko) * | 2013-09-16 | 2016-06-07 | 주식회사 엘지화학 | 이온 교환성 고분자 층을 포함하는 수처리 분리막 및 그 제조 방법 |
| KR20160083881A (ko) * | 2013-11-01 | 2016-07-12 | 버지니아 테크 인터렉추얼 프라퍼티스, 인크. | 가스분리막용 가교된 중합체 조성물 |
| CN107074706B (zh) * | 2014-10-28 | 2021-06-29 | 株式会社Lg化学 | 用于支化剂的氟系化合物、使用该氟系化合物的聚合物以及使用该聚合物的聚合物电解质膜 |
| WO2016066661A1 (en) * | 2014-10-31 | 2016-05-06 | Basf Se | Copolymers for making membranes |
| CN107001633B (zh) * | 2014-12-02 | 2019-07-02 | 株式会社Lg化学 | 聚合物、该聚合物的制备方法以及包含该聚合物的电解质膜 |
| KR102068872B1 (ko) * | 2015-09-22 | 2020-01-21 | 주식회사 엘지화학 | 블록 중합체 및 이를 포함하는 고분자 전해질막 |
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| US4625000A (en) | 1985-06-12 | 1986-11-25 | Union Carbide Corporation | Process for preparing sulfonated poly(aryl ether) resins |
| US6586561B1 (en) | 1999-02-18 | 2003-07-01 | Case Western Reserve University | Rigid rod ion conducting copolymers |
| JP4802354B2 (ja) | 1999-12-27 | 2011-10-26 | 住友化学株式会社 | 高分子電解質およびその製造方法 |
| JP3820888B2 (ja) | 2001-01-31 | 2006-09-13 | Ｊｓｒ株式会社 | スルホン酸基を有するポリエーテル系共重合体およびプロトン伝導膜 |
| KR100408877B1 (ko) | 2001-02-09 | 2003-12-18 | 이무성 | 불소화, 술폰화에 의한 스티렌-디엔계 공중합체와 그제조방법 및 이 공중합체를 이용한 연료전지용 고분자전해질막 |
| KR20020076825A (ko) | 2001-03-30 | 2002-10-11 | 대주정밀화학 주식회사 | 직접메탄올 연료전지용 이온교환막 |
| ATE337618T1 (de) * | 2001-05-08 | 2006-09-15 | Ube Industries | Polymerelektrolyt für eine brennstoffzelle des festpolymertyps und brennstoffzelle |
| JP3599041B2 (ja) | 2001-05-08 | 2004-12-08 | 宇部興産株式会社 | 固体高分子型燃料電池用高分子電解質及び燃料電池 |
| TW588076B (en) | 2001-07-03 | 2004-05-21 | Sumitomo Chemical Co | Polymer electrolyte membrane and fuel cell |
| JP4408599B2 (ja) | 2001-11-16 | 2010-02-03 | 東洋紡績株式会社 | スルホン酸基含有芳香族ポリアリーレンエーテル化合物および高分子電解質膜 |
| KR100977234B1 (ko) * | 2002-05-13 | 2010-08-23 | 더 유니버시티 오브 노스 플로리다 보드 오브 트러스티즈 | 술폰화된 공중합체 |
| KR100464317B1 (ko) * | 2002-07-06 | 2005-01-03 | 삼성에스디아이 주식회사 | 측쇄사슬에 산기를 갖는 양성자전도성 고분자, 상기 고분자를 이용한 고분자막 및 이를 이용한 연료전지 |
| DE602004030358D1 (de) * | 2003-10-02 | 2011-01-13 | Univ Yamanashi | Sulfonierte aromatische polyether, herstellungsverfahren dafür und elektrolytmembranen |
| KR20060019492A (ko) | 2004-08-26 | 2006-03-03 | 주식회사 엘지화학 | 신규한 술폰화 폴리이미드 공중합체 및 이를 이용한전해질막 |
-
2005
- 2005-12-13 TW TW094144105A patent/TWI294432B/zh not_active IP Right Cessation
- 2005-12-13 KR KR1020050122400A patent/KR100756821B1/ko not_active Expired - Lifetime
- 2005-12-13 US US11/301,243 patent/US7601785B2/en active Active
- 2005-12-14 EP EP05822104A patent/EP1828284B1/en not_active Expired - Lifetime
- 2005-12-14 CN CN2005800424506A patent/CN101076551B/zh not_active Expired - Lifetime
- 2005-12-14 JP JP2007544277A patent/JP2008521999A/ja active Pending
- 2005-12-14 WO PCT/KR2005/004291 patent/WO2006065068A1/en not_active Ceased
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