JP6943530B2 - 重合体及びこれを含む高分子分離膜 - Google Patents
重合体及びこれを含む高分子分離膜 Download PDFInfo
- Publication number
- JP6943530B2 JP6943530B2 JP2020519239A JP2020519239A JP6943530B2 JP 6943530 B2 JP6943530 B2 JP 6943530B2 JP 2020519239 A JP2020519239 A JP 2020519239A JP 2020519239 A JP2020519239 A JP 2020519239A JP 6943530 B2 JP6943530 B2 JP 6943530B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- polymer
- unsubstituted
- present specification
- 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.)
- Active
Links
- 229920000642 polymer Polymers 0.000 title claims description 153
- 239000012528 membrane Substances 0.000 title claims description 113
- 238000000926 separation method Methods 0.000 title claims description 84
- 239000000126 substance Substances 0.000 claims description 82
- 125000005843 halogen group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 239000000446 fuel Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 230000002209 hydrophobic effect Effects 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 238000005342 ion exchange Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 239000003792 electrolyte Substances 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 230000001590 oxidative effect Effects 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 8
- 230000000712 assembly Effects 0.000 claims description 7
- 238000000429 assembly Methods 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002560 nitrile group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 2
- 229920000867 polyelectrolyte Polymers 0.000 claims 1
- -1 1-methylpentyl Chemical group 0.000 description 64
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 20
- 229920001477 hydrophilic polymer Polymers 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 239000010408 film Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 239000008151 electrolyte solution Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920001400 block copolymer Polymers 0.000 description 8
- 238000009826 distribution Methods 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229920000557 Nafion® Polymers 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003014 ion exchange membrane Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 5
- 0 C*(CCC1=CCC(C)CC1)C1CC(C)(C)CCCC1 Chemical compound C*(CCC1=CCC(C)CC1)C1CC(C)(C)CCCC1 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000005518 polymer electrolyte Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002828 fuel tank Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003930 superacid Substances 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QCOYNDIJTAIYIF-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1.C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 QCOYNDIJTAIYIF-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- NFTRAGGUIJBGHD-UHFFFAOYSA-N N-(9H-fluoren-1-yl)phenanthren-1-amine Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC1=2)NC1=CC=CC=2C3=CC=CC=C3CC1=2 NFTRAGGUIJBGHD-UHFFFAOYSA-N 0.000 description 1
- ACYWVHCCUGTDEW-UHFFFAOYSA-N N-naphthalen-1-yl-9H-fluoren-1-amine Chemical group C1(=CC=CC2=CC=CC=C12)NC1=CC=CC=2C3=CC=CC=C3CC12 ACYWVHCCUGTDEW-UHFFFAOYSA-N 0.000 description 1
- WJOZUXJBWJTHQQ-UHFFFAOYSA-N N-phenyl-2-(2-phenylphenyl)aniline Chemical group C1(=CC=CC=C1)NC=1C(=CC=CC=1)C=1C(=CC=CC=1)C1=CC=CC=C1 WJOZUXJBWJTHQQ-UHFFFAOYSA-N 0.000 description 1
- 229910000820 Os alloy Inorganic materials 0.000 description 1
- 229910001252 Pd alloy Inorganic materials 0.000 description 1
- 229910000929 Ru alloy Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000005155 haloalkylene group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NJVSFOMTEFOHMI-UHFFFAOYSA-N n,2-diphenylaniline Chemical group C=1C=CC=C(C=2C=CC=CC=2)C=1NC1=CC=CC=C1 NJVSFOMTEFOHMI-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- HCISEFFYVMEPNF-UHFFFAOYSA-N n-phenyl-9h-fluoren-1-amine Chemical group C=12CC3=CC=CC=C3C2=CC=CC=1NC1=CC=CC=C1 HCISEFFYVMEPNF-UHFFFAOYSA-N 0.000 description 1
- UMGBMWFOGBJCJA-UHFFFAOYSA-N n-phenylphenanthren-1-amine Chemical group C=1C=CC(C2=CC=CC=C2C=C2)=C2C=1NC1=CC=CC=C1 UMGBMWFOGBJCJA-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- IYZXTLXQZSXOOV-UHFFFAOYSA-N osmium platinum Chemical compound [Os].[Pt] IYZXTLXQZSXOOV-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CFQCIHVMOFOCGH-UHFFFAOYSA-N platinum ruthenium Chemical compound [Ru].[Pt] CFQCIHVMOFOCGH-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910001456 vanadium ion Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- 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
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
- C08J5/2262—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation containing fluorine
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0245—Block or graft polymers
-
- 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
-
- 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
- C08G65/4006—(I) or (II) containing elements other than carbon, oxygen, hydrogen or halogen as leaving group (X)
-
- 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
- C08G65/4018—(I) or (II) containing halogens other than as leaving group (X)
- C08G65/4025—(I) or (II) containing fluorine other than as leaving group (X)
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0236—Polyarylenethioethers containing atoms other than carbon or sulfur in a linkage between arylene groups
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
-
- 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
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
-
- 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
- H01M8/02—Details
- H01M8/0202—Collectors; Separators, e.g. bipolar separators; Interconnectors
- H01M8/0204—Non-porous and characterised by the material
- H01M8/0221—Organic resins; 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
- H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
-
- 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
- H01M8/1025—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
-
- 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
- H01M8/1032—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having sulfur, e.g. sulfonated-polyethersulfones [S-PES]
-
- 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
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
-
- 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
- H01M8/18—Regenerative fuel cells, e.g. redox flow batteries or secondary fuel cells
- H01M8/184—Regeneration by electrochemical means
- H01M8/188—Regeneration by electrochemical means by recharging of redox couples containing fluids; Redox flow type batteries
-
- 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
-
- 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
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Sustainable Energy (AREA)
- Sustainable Development (AREA)
- Life Sciences & Earth Sciences (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polyethers (AREA)
- Silicon Polymers (AREA)
- Fuel Cell (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Conductive Materials (AREA)
Description
[化学式1]
L1は、直接結合;−S−;−O−;−NRa−;−SO2−;又は置換もしくは非置換の炭素数1〜10のアルキレン基であり、
Aは、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、 −PO3 2−2M+、−O(CF2)mSO3H、−O(CF2)mSO3 −M+、−O(CF2)mCOOH、−O(CF2)mCOO−M+、−O(CF2)mPO3H2、−O(CF2)mPO3H−M+、又は−O(CF2)mPO3 2−2M+であり、
mは、2〜6の整数であり、Mは、1族元素であり、
R1〜R5は、互いに同一であるか異なっており、それぞれ独立して、水素;ハロゲン基;又はヒドロキシ基であり、R1〜R5のうち少なくとも二つは、ハロゲン基;又はヒドロキシ基であり、
R6及びR7は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基であり、
Raは、水素;又は置換もしくは非置換のアルキル基であり、
nは、2〜10の整数であり、nが2以上の整数の場合、括弧内の構造は互いに同一であるか異なっている。
[化学式1]
L1は、直接結合;−S−;−O−;−NRa−;−SO2−;又は置換もしくは非置換の炭素数1〜10のアルキレン基であり、
Aは、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、−PO3 2−2M+、−O(CF2)mSO3H、−O(CF2)mSO3 −M+、−O(CF2)mCOOH、−O(CF2)mCOO−M+、−O(CF2)mPO3H2、−O(CF2)mPO3H−M+、又は−O(CF2)mPO3 2−2M+であり、
mは、2〜6の整数であり、Mは、1族元素であり、
R1〜R5は、互いに同一であるか異なっており、それぞれ独立して、水素;ハロゲン基;又はヒドロキシ基であり、R1〜R5のうち少なくとも二つは、ハロゲン基;又はヒドロキシ基であり、
R6及びR7は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基であり、
Raは、水素;又は置換もしくは非置換のアルキル基であり、
nは、2〜10の整数であり、nが2以上の整数の場合、括弧内の構造は互いに同一であるか異なっている。
[化学式1−1]
[化学式2]
X1は、直接結合;−C(Z1)(Z2)−;−O−;−S−;−SO2−;−CO−;又は−Si(Z1)(Z2)−であり、
Z1及びZ2は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;又は置換もしくは非置換のアリール基であり、
T1及びT2は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t1及びt2は、0〜4の整数であり、t1及びt2が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっている。
[化学式4]
x1、a及びa'は、括弧内の単位の繰り返し数であって、1〜1,000の整数であり、a:a'は、1,000:1〜1:1,000であり、
L11は、直接結合;−S−;−O−;−NRb−;−SO2−;又は置換もしくは非置換の炭素数 1〜10のアルキレン基であり、
A'は、−SO3H、−SO3 −M+、−COOH、−COO−M+、−PO3H2、−PO3H−M+、−PO3 2−2M+、−O(CF2)mSO3H、−O(CF2)mSO3 −M+、−O(CF2)mCOOH、−O(CF2)mCOO−M+、−O(CF2)mPO3H2、−O(CF2)mPO3H−M+、又は−O(CF2)mPO3 2−2M+であり、
mは、2〜6の整数であり、Mは、1族元素であり、
R16及びR17は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基であり、
Rbは、水素;又は置換もしくは非置換のアルキル基であり、
n'は、2〜10の整数であり、n'が2以上の整数の場合、括弧内の構造は互いに同一であるか異なっており、
X11は、直接結合;−C(Z11)(Z12)−;−O−;−S−;−SO2−;−CO−;又は −Si(Z11)(Z12)−であり、
Z11及びZ12は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;又は置換もしくは非置換のアリール基であり、
T11及びT12は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t11及びt12は、0〜4の整数であり、t11及びt12が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっている。
[化学式4−1]
[デカフルオロビフェニル(decafluorobiphenyl)]
[化学式3]
X2は、直接結合;−C(Z3)(Z4)−;−O−;−S−;−SO2−;−CO−;又は−Si(Z3)(Z4)−であり、
Z3及びZ4は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;又は置換もしくは非置換のアリール基であり、
T3及びT4は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t3及びt4は、0〜4の整数であり、t3及びt4が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっており、
但し、X2は、−C(Z3)(Z4)−;又は −Si(Z3)(Z4)−であり、 Z3及びZ4が互いに同一であるか異なっており、それぞれ独立して、ハロゲン基で置換されたアルキル基であるか、
X2が、直接結合;−C(Z3)(Z4)−;−O−;−S−;−SO2−;−CO−;又は−Si(Z3)(Z4)−であり、 Z3及びZ4がハロゲン基で置換されたアルキル基でない場合、T3 及びT4は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基;ハロゲン基で置換されたアルキル基;又はハロゲン基で置換されたアリール基であり、t3及びt4は、1〜4の整数である。
[化学式5]
x2、b及びb'は、括弧内の単位の繰り返し数であって、1〜1,000の整数であり、b:b'は、1,000 :1〜1:1,000であり、
X12は、直接結合;−C(Z13)(Z14)−;−O−;−S−;−SO2−;−CO−;又は −Si(Z13)(Z14)−であり、
Z13及びZ14は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;又は置換もしくは非置換のアリール基であり、
T13及びT14は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t13及びt14は、0〜4の整数であり、t13及びt14が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっており、
但し、X12は、−C(Z13)(Z14)−;又は−Si(Z13)(Z14)−であり、 Z13及びZ14が、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基で置換されたアルキル基であるか、
X12が、直接結合;−C(Z13)(Z14)−;−O−;−S−;−SO2−;−CO−;又は −Si(Z13)(Z14)−であり、Z13及びZ14が、ハロゲン基で置換されたアルキル基でない場合、T13及びT14は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基;ハロゲン基で置換されたアルキル基;又はハロゲン基で置換されたアリール基であり、t13及びt14は、1〜4の整数である。
[化学式6]
Xは、S;O;CO;SO;SO2;NR;炭化水素系又はフッ素系結合体であり、
lは、0〜100の整数であり、lが2以上の場合、2以上のXは、互いに同一であるか異なっており、
Q1及びQ2は、互いに同一であるか異なっており、それぞれ独立して、ヒドロキシ基及びハロゲン基からなる群より選択される置換基で1又は2以上置換された芳香族環;ヒドロキシ基及びハロゲン基からなる群より選択される置換基で1又は2以上置換された脂肪族環;又はNR'R''で表されるアミン基であり、
R、R'及びR''は、ハロゲン基で置換された芳香族環;又はハロゲン基で置換された脂肪族環であり、
Zは、3価の有機基である。
[化学式7−1]
L21〜L27は、互いに同一であるか異なっており、それぞれ独立して、直接結合;−S−;−O−;−CO−;又は−SO2−であり、
W11〜W21は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロ環基であり、
w1、w2、w3、w6、w8、w9及びw10は、それぞれ1〜4の整数であり、w4、w5及びw7は、それぞれ1〜3の整数であり、w11は、1〜6の整数であり、w1〜w11がそれぞれ 2以上の整数の場合、2以上の括弧内の構造は互いに同一であるか異なっている。
イオン伝導度(∂)=l/(R×d)
ここで、lは、両電極(electrode)間の距離(1cm)であり、Rは、SP−240を通じて測定された膜抵抗、そしてdは、イオン交換膜の厚さ(cm)である。イオン伝導度の単位は、S/cmで得られる。
上記実施例1で製造したブロック重合体をDMSO(dimethylsulfoxide)に20wt/v%で溶かした後、0.45μmのシリンジフィルターで濾過した。濾過した溶液をガラス板にキャスティング(casting)して高分子分離膜を製造し、80℃のオーブンで12時間乾燥後、真空オーブンで80℃で12時間乾燥した。
ナフィオン(Nafion)211(DuPont社)を使用して、上記実験例1と同様に陽イオン伝導度及びイオン交換能力(IEC)を測定し、その結果を下記表1に示す。
実施例1、3及び4の重合体から上記実験例1と同様の方法でフィルム状の高分子分離膜を製造した。
200a:アノード
200b:カソード
10:正極タンク
20:負極タンク
11、21:ポンプ
31:分離膜
32:正極セル
33:負極セル
41:正極電解液
42:負極電解液
60:スタック
70:酸化剤供給部
80:燃料供給部
81:燃料タンク
82:ポンプ
Claims (9)
- 親水性ブロック及び疎水性ブロックを含み、
前記親水性ブロックは、下記化学式4−1で表される繰り返し単位を含み、
前記疎水性ブロックは、下記化学式5−1で表される繰り返し単位を含むものである重合体:
[化学式4−1]
x1、a及びa'は、括弧内の単位の繰り返し数であって、1〜1,000の整数であり、a:a'は、1,000:1〜1:1,000であり、
L11は、−S−であり、
A'は、−O(CF 2 ) m SO 3 H、又は−O(CF 2 ) m SO 3 − M + であり、
mは、2〜6の整数であり、Mは、1族元素であり、
R16及びR17は、Fであり、
n'は、2〜10の整数であり、n'が2以上の整数の場合、括弧内の構造は互いに同一であるか異なっており、
X11は、−C(CF 3 )(CF 3 )−;又は−O−であり、
T11及びT12は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t11及びt12は、0〜4の整数であり、t11及びt12が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっており、
x2、b及びb'は、括弧内の単位の繰り返し数であって、1〜1,000の整数であり、b:b'は、1,000 :1〜1:1,000であり、
X12は、直接結合;−C(Z13)(Z14)−;−O−;−S−;−SO 2 −;−CO−;又は −Si(Z13)(Z14)−であり、
Z13及びZ14は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;又は置換もしくは非置換のアリール基であり、
T13及びT14は、互いに同一であるか異なっており、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;又は置換もしくは非置換のヘテロアリール基であり、t13及びt14は、0〜4の整数であり、t13及びt14が2以上の整数の場合、括弧内の置換基は互いに同一であるか異なっており、
但し、X12は、−C(Z13)(Z14)−;又は−Si(Z13)(Z14)−であり、 Z13及びZ14が、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基で置換されたアルキル基であるか、
X12が、直接結合;−C(Z13)(Z14)−;−O−;−S−;−SO 2 −;−CO−;又は −Si(Z13)(Z14)−であり、Z13及びZ14が、ハロゲン基で置換されたアルキル基でない場合、T13及びT14は、互いに同一であるか異なっており、それぞれ独立して、ハロゲン基;ハロゲン基で置換されたアルキル基;又はハロゲン基で置換されたアリール基であり、t13及びt14は、1〜4の整数である。 - 前記重合体は、ブロック重合体である、請求項1に記載の重合体。
- 前記重合体は、下記化学式6の化合物から由来するブランチャー又は下記化学式7で表されるブランチャーをさらに含むものである、請求項1に記載の重合体:
[化学式6]
Xは、S;O;CO;SO;SO2;NR;炭化水素系又はフッ素系結合体であり、
lは、0〜100の整数であり、lが2以上の場合、2以上のXは、互いに同一であるか異なっており、
Q1及びQ2は、互いに同一であるか異なっており、それぞれ独立して、ヒドロキシ基及びハロゲン基からなる群より選択される置換基で1又は2以上置換された芳香族環;ヒドロキシ基及びハロゲン基からなる群より選択される置換基で1又は2以上置換された脂肪族環;又はNR'R''で表されるアミン基であり、
R、R'及びR''は、ハロゲン基で置換された芳香族環;又はハロゲン基で置換された脂肪族環であり、
Zは、3価の有機基である。 - 請求項1〜3のいずれか一項に記載の重合体を含む高分子分離膜。
- 前記高分子分離膜のイオン伝導度は、0.005S/cm〜0.8S/cmである、請求項4に記載の高分子分離膜。
- 前記高分子分離膜のイオン交換容量(IEC)は、0.01mmol/g〜5mmol/gである、 請求項4または5に記載の高分子分離膜。
- アノード;カソード;及び前記アノードと前記カソードとの間に備えられた請求項4から6のいずれか一項に記載の高分子分離膜を含む膜電極接合体。
- 2以上の請求項7に記載の膜電極接合体;
前記膜電極接合体の間に備えられるバイポーラプレートを含むスタック;
前記スタックに燃料を供給する燃料供給部;及び
前記スタックに酸化剤を供給する酸化剤供給部を含む高分子電解質型燃料電池。 - 正極及び正極電解液を含む正極セル;
負極及び負極電解液を含む負極セル;及び
前記正極セルと前記負極セルとの間に備えられる請求項4から6のいずれか一項に記載の高分子分離膜を含むレドックスフロー電池。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2017-0154253 | 2017-11-17 | ||
KR20170154253 | 2017-11-17 | ||
PCT/KR2018/014137 WO2019098771A1 (ko) | 2017-11-17 | 2018-11-16 | 중합체 및 이를 포함하는 고분자 분리막 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020536989A JP2020536989A (ja) | 2020-12-17 |
JP6943530B2 true JP6943530B2 (ja) | 2021-10-06 |
Family
ID=66539714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020519239A Active JP6943530B2 (ja) | 2017-11-17 | 2018-11-16 | 重合体及びこれを含む高分子分離膜 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11618804B2 (ja) |
EP (1) | EP3683254A4 (ja) |
JP (1) | JP6943530B2 (ja) |
KR (1) | KR20190057000A (ja) |
CN (1) | CN111164132B (ja) |
WO (1) | WO2019098771A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112608482B (zh) * | 2020-12-15 | 2022-09-09 | 温州大学 | 一种铵根离子修饰的含氟嵌段共聚物及其应用 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100696460B1 (ko) | 2003-06-05 | 2007-03-19 | 삼성에스디아이 주식회사 | 수소이온 전도성 폴리머 |
US20070292730A1 (en) * | 2003-11-20 | 2007-12-20 | Mcgrath James E | Multiblock Copolymers Containing Hydrophilic Hydrophobic Segments for Proton Exchange Membrane |
KR20060115896A (ko) | 2003-12-02 | 2006-11-10 | 어드밴스드 테크놀러지 머티리얼즈, 인코포레이티드 | 레지스트, barc 및 갭 필 재료 스트리핑 케미칼 및방법 |
CA2562124A1 (en) | 2004-04-06 | 2005-10-20 | Sumitomo Chemical Company, Limited | Polyarylene polymer and use thereof |
KR100853713B1 (ko) | 2007-03-29 | 2008-08-25 | 한국과학기술원 | 연료전지용 고분자 복합막 및 이를 포함하는 연료전지 |
JP2010232159A (ja) | 2009-03-06 | 2010-10-14 | Harison Toshiba Lighting Corp | 放電ランプおよびその製造方法 |
KR101566789B1 (ko) | 2009-12-04 | 2015-11-09 | 현대자동차 주식회사 | 술폰산기를 갖는 폴리(아릴렌에테르) 공중합체, 이의 제조방법 및 이를 이용한 연료전지용 고분자 전해질 막 |
JP2013189515A (ja) * | 2012-03-13 | 2013-09-26 | Toyobo Co Ltd | 芳香族炭化水素系ポリマーとそれを用いてなる電解質膜、膜電極接合体、及び燃料電池 |
WO2014200286A2 (ko) * | 2013-06-14 | 2014-12-18 | 주식회사 엘지화학 | 술포네이트계 화합물 및 이를 이용한 고분자 전해질막 |
JP6049212B2 (ja) * | 2014-03-17 | 2016-12-21 | 国立大学法人山梨大学 | 陰イオン交換樹脂、燃料電池用電解質膜、電極触媒層形成用バインダー、電池電極触媒層および燃料電池 |
WO2016089156A2 (ko) * | 2014-12-04 | 2016-06-09 | 주식회사 엘지화학 | 중합체 및 이를 포함하는 고분자 전해질막 |
CN107004880B (zh) * | 2014-12-04 | 2020-07-28 | 株式会社Lg化学 | 聚合物电解质膜 |
KR20160067720A (ko) * | 2014-12-04 | 2016-06-14 | 주식회사 엘지화학 | 중합체 및 이를 포함하는 고분자 전해질막 |
KR101947605B1 (ko) * | 2015-01-26 | 2019-02-14 | 주식회사 엘지화학 | 할로겐화 화합물, 중합체 및 이를 포함하는 고분자 전해질막 |
FR3039321A1 (fr) * | 2015-07-22 | 2017-01-27 | Centre Nat Rech Scient | Ionomeres aromatiques |
CN108884213B (zh) * | 2016-03-29 | 2020-08-18 | 株式会社Lg化学 | 嵌段聚合物和包含该嵌段聚合物的聚合物电解质膜 |
-
2018
- 2018-11-16 JP JP2020519239A patent/JP6943530B2/ja active Active
- 2018-11-16 KR KR1020180141983A patent/KR20190057000A/ko not_active IP Right Cessation
- 2018-11-16 US US16/754,630 patent/US11618804B2/en active Active
- 2018-11-16 CN CN201880064710.7A patent/CN111164132B/zh active Active
- 2018-11-16 EP EP18879548.8A patent/EP3683254A4/en active Pending
- 2018-11-16 WO PCT/KR2018/014137 patent/WO2019098771A1/ko unknown
Also Published As
Publication number | Publication date |
---|---|
CN111164132A (zh) | 2020-05-15 |
WO2019098771A1 (ko) | 2019-05-23 |
EP3683254A4 (en) | 2020-09-09 |
KR20190057000A (ko) | 2019-05-27 |
US20200354523A1 (en) | 2020-11-12 |
US11618804B2 (en) | 2023-04-04 |
EP3683254A1 (en) | 2020-07-22 |
CN111164132B (zh) | 2022-12-16 |
JP2020536989A (ja) | 2020-12-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6972003B2 (ja) | ブロック重合体およびこれを含む高分子電解質膜 | |
KR101947605B1 (ko) | 할로겐화 화합물, 중합체 및 이를 포함하는 고분자 전해질막 | |
JP6943530B2 (ja) | 重合体及びこれを含む高分子分離膜 | |
KR101991430B1 (ko) | 할로겐화 화합물, 이를 포함하는 중합체 및 이를 포함하는 고분자 전해질막 | |
KR102695260B1 (ko) | 교호 공중합체 및 이의 제조방법 | |
EP3327059B1 (en) | Block polymer and polymer electrolyte membrane including same | |
EP3235809B1 (en) | Compound and polymer electrolyte membrane using same | |
KR102088080B1 (ko) | 중합체, 이를 포함하는 전해질막, 이를 포함하는 연료전지 및 레독스 플로우 전지 | |
KR102672160B1 (ko) | 중합체, 이를 포함하는 고분자 분리막, 이를 포함하는 막 전극 집합체, 연료전지 및 레독스 플로우 전지 | |
KR102462755B1 (ko) | 중합체, 이의 제조방법 및 이를 포함하는 고분자 분리막 | |
KR102026509B1 (ko) | 화합물, 이를 이용한 고분자 및 이를 이용한 전해질막 | |
KR102169847B1 (ko) | 중합체 및 이를 포함하는 막 | |
KR102481620B1 (ko) | 블록 공중합체 및 이의 제조방법 | |
KR20170062398A (ko) | 화합물, 이를 이용한 고분자, 이를 이용한 고분자 전해질막 | |
KR102059226B1 (ko) | 멀티블록 고분자, 이를 포함하는 전해질막 및 이를 포함하는 연료전지 | |
KR102074552B1 (ko) | 할로겐화 화합물 및 이를 이용한 고분자 전해질막 | |
KR102026510B1 (ko) | 화합물, 이를 이용한 고분자 및 이를 이용한 전해질막 | |
KR20170131030A (ko) | 불소계 화합물 및 이를 이용한 고분자 전해질막 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200408 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20210414 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210427 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210715 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210810 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210907 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6943530 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |