JP5472267B2 - 含窒素芳香族化合物およびその製造方法、重合体およびプロトン伝導膜 - Google Patents
含窒素芳香族化合物およびその製造方法、重合体およびプロトン伝導膜 Download PDFInfo
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- JP5472267B2 JP5472267B2 JP2011251579A JP2011251579A JP5472267B2 JP 5472267 B2 JP5472267 B2 JP 5472267B2 JP 2011251579 A JP2011251579 A JP 2011251579A JP 2011251579 A JP2011251579 A JP 2011251579A JP 5472267 B2 JP5472267 B2 JP 5472267B2
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- containing heterocyclic
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- 229920000642 polymer Polymers 0.000 title claims description 138
- -1 Nitrogen-containing aromatic compound Chemical class 0.000 title claims description 48
- 239000012528 membrane Substances 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 41
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 6
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 6
- 150000003536 tetrazoles Chemical class 0.000 claims description 6
- 150000003852 triazoles Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000008282 halocarbons Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 41
- 238000000034 method Methods 0.000 description 40
- 229910052757 nitrogen Chemical group 0.000 description 32
- 239000000178 monomer Substances 0.000 description 29
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 14
- 238000005227 gel permeation chromatography Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000000446 fuel Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000005266 casting Methods 0.000 description 12
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 238000005342 ion exchange Methods 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 238000007654 immersion Methods 0.000 description 11
- 238000010248 power generation Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 229910052725 zinc Inorganic materials 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 9
- 235000009518 sodium iodide Nutrition 0.000 description 9
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 9
- 239000002966 varnish Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- WJGLGPTVKGZNBK-UHFFFAOYSA-N (2,5-dichlorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC(Cl)=CC=C1Cl WJGLGPTVKGZNBK-UHFFFAOYSA-N 0.000 description 5
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 5
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000013557 residual solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 4
- NMWIEPTXGTYJHD-UHFFFAOYSA-N (2,5-dichlorophenyl)-(4-imidazol-1-ylphenyl)methanone Chemical compound ClC1=CC=C(Cl)C(C(=O)C=2C=CC(=CC=2)N2C=NC=C2)=C1 NMWIEPTXGTYJHD-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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- 238000004809 thin layer chromatography Methods 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- VHXNNVZZGMWSBN-UHFFFAOYSA-N (2,5-dichlorophenyl)-(4-phenoxyphenyl)methanone Chemical compound ClC1=CC=C(Cl)C(C(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 VHXNNVZZGMWSBN-UHFFFAOYSA-N 0.000 description 2
- LBWWKAQXLRAHCO-UHFFFAOYSA-N (2,5-dichlorophenyl)-(4-pyrrol-1-ylphenyl)methanone Chemical compound ClC1=CC=C(Cl)C(C(=O)C=2C=CC(=CC=2)N2C=CC=C2)=C1 LBWWKAQXLRAHCO-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 0 C*C(C)c1ccccc1 Chemical compound C*C(C)c1ccccc1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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- 239000006227 byproduct Substances 0.000 description 2
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- 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
- 238000003379 elimination reaction Methods 0.000 description 2
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- 239000010410 layer Substances 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 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 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
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- UVAKGOJIHCGXID-UHFFFAOYSA-N (2,4-dichlorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl UVAKGOJIHCGXID-UHFFFAOYSA-N 0.000 description 1
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- LVYVYRQFAQYKFW-UHFFFAOYSA-N (2,5-dichlorophenyl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1Cl LVYVYRQFAQYKFW-UHFFFAOYSA-N 0.000 description 1
- BVTAAMCWUFECHC-UHFFFAOYSA-N (2,5-dichlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC(Cl)=CC=C1Cl BVTAAMCWUFECHC-UHFFFAOYSA-N 0.000 description 1
- ZXBFOJHBBGEREU-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=C(Cl)C=CC=C1Cl ZXBFOJHBBGEREU-UHFFFAOYSA-N 0.000 description 1
- MLWKCPQXHJATBQ-UHFFFAOYSA-N (2,6-dichlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(Cl)C=CC=C1Cl MLWKCPQXHJATBQ-UHFFFAOYSA-N 0.000 description 1
- BJLVHBDHEMFVIE-UHFFFAOYSA-N (4-chlorophenyl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1OC(=O)C1=CC=C(Cl)C=C1 BJLVHBDHEMFVIE-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
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- RXMGEHVYVGPSSN-UHFFFAOYSA-N 1-chloro-4-[2-(4-chlorophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(Cl)C=C1 RXMGEHVYVGPSSN-UHFFFAOYSA-N 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
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- WXARQXZZFOCDNR-UHFFFAOYSA-N 4-chloro-n-(4-chlorophenyl)benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 WXARQXZZFOCDNR-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- NSWRSAFGHPRHGG-UHFFFAOYSA-L dichloronickel;2-pyridin-2-ylpyridine Chemical compound Cl[Ni]Cl.N1=CC=CC=C1C1=CC=CC=N1 NSWRSAFGHPRHGG-UHFFFAOYSA-L 0.000 description 1
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- 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
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- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- IQQDNMHUOLMLNJ-UHFFFAOYSA-N quinolin-3-ol Chemical compound C1=CC=CC2=CC(O)=CN=C21 IQQDNMHUOLMLNJ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
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Description
[1-1]下記一般式(1)で表される含窒素芳香族化合物。
[2-2]含窒素複素環基を有する側鎖が下記一般式(D)で表される構造である[2-1]の重合体。
[2-4]スルホン酸基を有する側鎖が下記一般式(E)で表される[2-1]の重合体。
[2-7][2-1]〜[2-6]の重合体からなるプロトン伝導膜。
本発明によれば、本来、耐熱水性が高く、高いスルホン酸濃度を有し、優れたプロトン伝導性を示す重合体中に、含窒素複素環式芳香族基を導入することで、プロトン伝導性を損なうことなく、高温下で高いスルホン酸の安定性を有するプロトン伝導膜が得られる。このため、燃料電池用のプロトン伝導膜に使用した際は、広範囲な温度、湿度、特に高温下でも発電可能になり、発電出力を向上することができる。また、高温下で使用しても、スルホン酸基が高い安定性を有することから、電池寿命を大幅に向上させた燃料電池を得ることができる。
[含窒素芳香族化合物]
本発明に係る含窒素芳香族化合物は、下記一般式(1)で表される。
pは0〜4の整数を示し、好ましくは、0または1である。
一般式(1)で表される含窒素芳香族化合物の具体例として、下記の化合物を挙げることができる。
下記一般式(2)で表される化合物と、含窒素複素環化合物とを、求核置換反応させる。
一般式(2)で表される化合物の具体例としては、2,4−ジクロロ−4'−フルオロベンゾフェノン、2,5−ジクロロ−4'−フルオロベンゾフェノン、2,6−ジクロロ−4'−フルオロベンゾフェノン、2,4−ジクロロ−2'−フルオロベンゾフェノン、2,5−ジクロロ−2'−フルオロベンゾフェノン、2,6−ジクロロ−2'−フルオロベンゾフェノン、2,4−ジクロロフェニル−4'−フルオロフェニルスルホン、2,5−ジクロロフェニル−4'−フルオロフェニルスルホン、2,6−ジクロロフェニル−4'−フルオロフェニルスルホン、2,4−ジクロロフェニル−2'−フルオロフェニルスルホン、2,4−ジクロロフェニル−2'−フルオロフェニルスルホン、2,4−ジクロロフェニル−2'−フルオロフェニルスルホンなどが挙げられる。
含窒素複素環化合物は、活性水素を有するものであり、この活性水素と一般式(2)で表される化合物のX'で表される基を置換反応させる。
一般式(1)で表される化合物と活性水素を有する含窒素複素環化合物との反応は、有機溶媒中で行うことが好ましい。N−メチル−2−ピロリドン、N,N−ジメチルアセトアミド、スルホラン、ジフェニルスルホン、ジメチルスルホキシドなどの極性溶媒を用いる。反応を促進するために、アルカリ金属、水素化アルカリ金属、水酸化アルカリ金属、アルカリ金属炭酸塩などを用いる。一般式(2)で表される化合物と、活性水素を有する含窒素複素環化合物との比率は、等モルもしくは活性水素を有する含窒素複素環化合物を過剰に加えて反応させる。具体的には、活性水素を有する含窒素複素環化合物は一般式(2)で表される化合物の1〜3倍モル、特に1〜1.5倍モル使用することが好ましい。
生成物は再結晶などの方法で精製して用いることが好ましい。
本発明の重合体は、主鎖がポリフェニレン構造であり、スルホン酸基を有する側鎖と含窒素複素環基を有する側鎖とを有する構造を含むものである。
pは0〜4の整数を示し、好ましくは、0または1である。
また、スルホン酸基を有する側鎖は、下記一般式(E)で表される。
O−、−(CF2)l−(lは1〜10の整数である)、−C(CF3)2−からなる群より選ばれた少なくとも1種の構造を示す。このうち、−CO−、−SO2−が好ましい。
m、nの値とY、Z、Arの構造についての好ましい組み合わせとして、
(1)m=0、n=0であり、Y1は−CO−であり、Arが置換基として−SO3Hを有
するフェニル基である構造、
(2)m=1、n=0であり、Y1は−CO−であり、Z1は−O−であり、Arが置換基として−SO3Hを有するフェニル基である構造、
(3)m=1、n=1、k=1であり、Y1は−CO−であり、Z1は−O−であり、Arが置換基として−SO3Hを有するフェニル基である構造、
(4)m=1、n=0であり、Y1は−CO−であり、Z1は−O−であり、Arが置換基として2個の−SO3Hを有するナフチル基である構造、
(5)m=1、n=0であり、Y1は−CO−であり、Z1は−O−であり、Arが置換基として−O(CH2)4SO3Hを有するフェニル基である構造などを挙げることができる。
本発明の重合体は、下記一般式(C)および(A)で表される繰り返し単位を含む。
(1)s=1、t=1であり、Aが−CR'2−(R'は脂肪族炭化水素基、芳香族炭化水素基およびハロゲン化炭化水素基を示す)、シクロヘキシリデン基、フルオレニリデン基であり、Bが酸素原子であり、Dが−CO−または、−SO2−であり、R1〜R16が水素原子またはフッ素原子である構造、
(2)s=1、t=0であり、Bが酸素原子であり、Dが−CO−または、−SO2−であり、R1〜R16が水素原子またはフッ素原子である構造、
(3)s=0、t=1であり、Aが−CR'2−(R'は脂肪族炭化水素基、芳香族炭化水素基およびハロゲン化炭化水素基を示す)、シクロヘキシリデン基、フルオレニリデン基、Bが酸素原子であり、R1〜R16が水素原子またはフッ素原子またはニトリル基である構造が挙げられる。
スルホン酸基を有する重合体の製造には、例えば下記に示すA法、B法、C法の3通りの方法を用いることができる。
例えば、特開2004−137444号公報に記載の方法と同様に、下記一般式(A')で表されるモノマー、下記一般式(B')で表されるモノマーおよび下記一般式(C')で表されるモノマーを共重合させ、スルホン酸エステル基を有する重合体を製造し、このスルホン酸エステル基を脱エステル化して、スルホン酸エステル基をスルホン酸基に変換することにより合成することができる。
モノマー(A')
モノマー(B')の具体例としては、一般式(B')におけるrが0の場合、例えば4,4'−ジクロロベンゾフェノン、4,4'−ジクロロベンズアニリド、2,2−ビス(4−クロロフェニル)ジフルオロメタン、2,2−ビス(4−クロロフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン、4−クロロ安息香酸−4−クロロフェニルエステル、ビス(4−クロロフェニル)スルホキシド、ビス(4−クロロフェニル)スルホン、2,6−ジクロロベンゾニトリルが挙げられる。これらの化合物において塩素原子が臭素原子またはヨウ素原子に置き換わった化合物などが挙げられる。
モノマー(C)の具体例として、前記式(1)で表される含窒素芳香族化合物を挙げることができる。
本発明の重合体を得るためはまず上記モノマー(A')、モノマー(C')および必要に応じてもモノマー(B')を共重合させ、前駆体を得る。
加水分解は、(1)少量の塩酸を含む過剰量の水またはアルコールに、上記スルホン酸エステル基を有する重合体を投入し、5分間以上撹拌する方法、(2)トリフルオロ酢酸中で上記スルホン酸エステル基を有する重合体を80〜120℃程度の温度で5〜10時間程度反応させる方法、(3)重合体中のスルホン酸エステル基(−SO3R)1モルに
対して1〜3倍モルのリチウムブロマイドを含む溶液、例えばN−メチルピロリドンなどの溶液中で上記スルホン酸エステル基を有する重合体を80〜150℃程度の温度で3〜10時間程度反応させた後、塩酸を添加する方法などにより行うことができる。
例えば、特開2001−342241号公報に記載の方法と同様に、上記一般式(A')で表される骨格を有し、かつスルホン酸基、スルホン酸エステル基を有しないモノマーと、上記モノマー(B')と、上記モノマー(C')を共重合させ、この重合体を、スルホン化剤を用いて、スルホン化することにより合成することもできる。
一般式(A)において、Arが−O(CH2)hSO3Hまたは−O(CF2)hSO3Hで表される置換基を有する芳香族基である場合には、例えば、特開2005−606254号公報に記載の方法と同様に、上記一般式(A)で表される構造単位となりうる前駆体のモノマーと、上記一般式(B)で表される構造単位となりうるモノマー、またはオリゴマーと、上記一般式(C)で表される構造単位となるモノマーを共重合させ、次にアルキルスルホン酸またはフッ素置換されたアルキルスルホン酸を導入する方法で合成することもできる。
本発明に係るプロトン伝導膜は、上記スルホン酸基と上記含窒素複素環基を有する重合体からなる。
が挙げられる。これらの中では、幅広い組成範囲で溶液粘度を下げる効果があることから、メタノールが特に好ましい。アルコールは、1種単独で用いても、2種以上を組み合わせて用いてもよい。
製膜する際の溶液のポリマー濃度は、通常5〜40重量%、好ましくは7〜25重量%である。ポリマー濃度が5重量%未満では、厚膜化し難く、また、ピンホールが生成しやすい傾向にある。一方、ポリマー濃度が40重量%を超えると、溶液粘度が高すぎてフィルム化し難く、また、表面平滑性に欠けることがある。
本発明の方法により得られるプロトン伝導膜は、その乾燥膜厚が、通常10〜100μm、好ましくは20〜80μmである。
以下に実施例を挙げ、本発明を具体的に説明するが、本発明は以下の実施例に限定されるものではない。
[実施例1-1] 2,5−ジクロロ-4'-(1−イミダゾリル)ベンゾフェノンの合成
得られたスルホン化重合体の15重量%溶液(溶媒はメタノール/NMP=50/50(容量比)の混合溶媒)からキャスト膜を調製した。これを大量の蒸留水に一晩浸漬し、膜中の残存NMPを希釈により取り除いた後、乾燥し、膜を得た(膜厚40μm)。
膜厚40μm)。
得られたスルホン酸基を有する重合体の水洗水が中性になるまで洗浄し、フリーに残存している酸を除いて充分に水洗し、乾燥後、所定量を秤量し、THF/水の混合溶剤に溶解したフェノールフタレインを指示薬とし、NaOHの標準液を用いて滴定を行い、中和点から、スルホン酸当量を求めた。
スルホン酸基を有しない重合体重量平均分子量は、溶剤としてテトラヒドロフラン(THF)を用い、GPCによって、ポリスチレン換算の分子量を求めた。
交流抵抗は、5mm幅の短冊状膜試料の表面に、白金線(φ=0.5mm)を押し当て、恒温恒湿装置中に試料を保持し、白金線間の交流インピーダンス測定から求めた。すなわち、85℃、相対湿度90%の環境下で交流10kHzにおけるインピーダンスを測定した。抵抗測定装置として、(株)NF回路設計ブロック製のケミカルインピーダンス測定システムを用い、恒温恒湿装置には、(株)ヤマト科学製のJW241を使用した。白金線は、5mm間隔に5本押し当てて、線間距離を5〜20mmに変化させ、交流抵抗を測定した。線間距離と抵抗の勾配から、膜の比抵抗を算出した。
比抵抗R(Ω・cm)=0.5(cm)×膜厚(cm)×抵抗線間勾配(Ω/cm)
膜厚約40μmの各フィルムを、160℃オーブン中に24時間入れた。耐熱試験前後のサンプルを、上記のNMP系のGPC溶離液99.8重量部に対し、0.2重量部のプロトン伝導膜を浸漬、溶解後、不溶分を除去し、GPC測定を行った。耐熱試験前後のGPCの溶出面積の比から不溶分含量を求めた。
(1)含窒素複素環基含有スルホン化重合体A−N1の合成
2,5−ジクロロ−4'−フェノキシベンゾフェノン185.3g(0.540mol)、4,4′−ジクロロベンゾフェノン15. 1g(0.060mol)、実施例1-2で得られた2,5−ジクロロ−4'−(1−ピロリル)ベンゾフェノン7.1g(0.024mol)、ヨウ化ナトリウム11.7g(0.078mol)、ビス(トリフェニルホスフィン)ニッケルジクロリド11.8g(0.018mmol)、トリフェニルホスフィン63.0g(0.240mol)、亜鉛94.1g(1.440mol)を冷却管、三方コックを取り付けた三口フラスコに入れ、70℃のオイルバスにつけ、窒素置換後、窒素雰囲気下にN−メチル−2−ピロリドン1000mlを加え、反応を開始した。20時間反応後、N−メチル−2−ピロリドン500mlで希釈し、1:10塩酸/メタノール溶液に重合反応液を注ぎ、ポリマーを析出、洗浄後、ろ過、真空乾燥後、白色の粉末を得た。収量は、148gであった。また、重量平均分子量は、154,000であった。このポリマー150gに対し、濃硫酸1500mlを加え室温で24時間、攪拌しスルホン化反応を行った。反応後、大量の純水中に注ぎ、スルホン化ポリマーを析出させた。pH7になるまでポリマーを純水によって洗浄し、ろ過後、スルホン化ポリマーを回収し、90゜C で真空乾燥した。スルホン化ポリマーの収量は159gであった。このポリマーのイオン交換容量は2.3meq/g、重量平均分子量は185,000であった。このようにして得られたポリマーは、構造式(A−N1)で表される。スルホン酸基を有する重合体を、ポリマーA−N1とする。
上記で得られた含窒素複素環基含有スルホン化重合体A―N1を、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)疎水性ユニットBの合成
攪拌機、温度計、Dean-stark管、窒素導入管、冷却管をとりつけた1Lの三口フラスコに、4,4'−ジクロロジフェニルスルホン29.8g(0.104mol)、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン37.4g(0.111mol)、炭酸カリウム20.0g(0.145mol)をはかりとった。窒素置換後、スルホラン168mL、トルエン84mLを加えて攪拌した。オイルバスで反応液を150℃で加熱還流させた。反応によって生成する水はDean-stark管にトラップした。3時間後、水の生成がほとんど認められなくなったところで、トルエンをDean-stark管から系外に除去した。徐々に反応温度を200℃に上げ、5時間攪拌を続けた後、4,4'−ジクロロベンゾフェノン7.5g(0.030mol)を加え、さらに8時間反応させた。反応液を放冷後、トルエン100mLを加えて希釈した。反応液に不溶の無機塩を濾過し、濾液をメタノール2Lに注いで生成物を沈殿させた。沈殿した生成物を濾過、乾燥後、テトラヒドロフラン250mLに溶解し、これをメタノール2Lに注いで再沈殿させた。沈殿した白色粉末を濾過、乾燥し、疎水性ユニットB56gを得た。GPCで測定した数平均分子量(Mn)は10,500であった。得られた化合物は、式(B−1)で表される。
攪拌機、温度計、窒素導入管をとりつけた1Lの三口フラスコに、3−(2,5−ジクロロベンゾイル)ベンゼンスルホン酸ネオペンチル141.6g(0.338mol)、上記で得られたMn10,500の疎水性ユニットB44.5g(4.2mmol)、実施例1-1で得られた2,5−ジクロロ−4'−(1−イミダゾリル)ベンゾフェノン5.4g(16.9mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド6.71g(10.3mmol)、ヨウ化ナトリウム1.54g(10.3mmol)、トリフェニルホスフィン35.9g(137mmol)、亜鉛53.7g(820mmol)をはかりとり、乾燥窒素置換した。ここにN,N-ジメチルアセトアミド(DMAc)430mLを加え、反応温度を80℃に保持しながら3時間攪拌を続けた後、DMAc730mLを加えて希釈し、不溶物を濾過した。
上記で得られた含窒素複素環基含有スルホン化重合体B―N1を、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)疎水性ユニットCの合成
撹拌機、温度計、冷却管、Dean-Stark管、窒素導入の三方コックを取り付けた1Lの三つ口のフラスコに、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン67.3g(0.200mol)、4,4'−ジクロロベンゾフェノン(4,4'−DCBP)60.3g(0.240mol)、炭酸カリウム71.9g(0.520mol)、N,N−ジメチルアセトアミド(DMAc)300mL、トルエン150mLをとり、オイルバス中、窒素雰囲気下で加熱し撹拌下130℃で反応させた。反応により生成する水をトルエンと共沸させ、Dean-Stark管で系外に除去しながら反応させると、約3時間で水の生成がほとんど認められなくなった。反応温度を130℃から徐々に150℃まで上げた。その後、反応温度を徐々に150℃まで上げながら大部分のトルエンを除去し、150℃で10時間反応を続けた後、4,4'−DCBP10.0g(0.040mol)を加え、さらに5時間反応した。得られた反応液を放冷後、副生した無機化合物の沈殿物を濾過除去し、濾液を4Lのメタノール中に投入した。沈殿した生成物を濾別、回収し乾燥後、テトラヒドロフラン300mLに溶解した。これをメタノール4Lに再沈殿し、目的の化合物95g(収率85%)を得た。
乾燥したN,N−ジメチルアセトアミド(DMAc)100mLを下記構造式C−2で
表される化合物モノマーC 27.21g(0.039mol)と、(1)で合成した疎水性ユニット16.13g(1.44mmol)、実施例1-3で得られた2,5-ジクロロ−4'−(2−ベンゾチアゾールチオキシ)ベンゾフェノン0.80g(1.93mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド0.79g(1.2mmol)、トリフェニルホスフィン4.20g(0.016mol)、ヨウ化ナトリウム0.18g(1.20mmol)、亜鉛6.28g(96.1mmol)の混合物中に窒素下で加えた。
上記で得られた含窒素複素環基含有スルホン化重合体C―N1を、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)疎水性ユニットDの合成
撹拌機、温度計、冷却管、Dean-Stark管、窒素導入の三方コックを取り付けた1Lの三つ口のフラスコに、2,6−ジクロロベンゾニトリル49.4g(0.29mol)、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン88.4g(0.26mol)、炭酸カリウム47.3g(0.34mol)をはかりとった。窒素置換後、スルホラン346ml、トルエン173mlを加えて攪拌した。フラスコをオイルバスにつけ、150℃に加熱還流させた。反応により生成する水をトルエンと共沸させ、Dean-Stark管で系外に除去しながら反応させると、約3時間で水の生成がほとんど認められなくなった。反応温度を徐々に上げながら大部分のトルエンを除去した後、200℃で3時間反応を続けた。次に、2,6−ジクロロベンゾニトリル12.3g(0.072mol)を加え、さらに5時間反応した。
乾燥したN,N−ジメチルアセトアミド(DMAc)540mLを、3−(2,5−ジクロロベンゾイル)ベンゼンスルホン酸ネオペンチル135.0g(0.336mol)と、(1)で合成した疎水性ユニットD40.7g(5.6mmol)、実施例1-2で得られた2,5−ジクロロ−4'−(1−イミダゾリル)ベンゾフェノン6.71g(16.8mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド6.71g(10.3mmol)、トリフェニルホスフィン35.9g(0.137mol)、ヨウ化ナトリウム1.54g(10.3mmol)、亜鉛53.7g(0.821mol)の混合物中に窒素下で加えた。
上記で得られた含窒素複素環基含有スルホン化重合体D-N1を、メタノール/NMP
=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)スルホン化重合体RAの合成
2,5−ジクロロ−4'−フェノキシベンゾフェノン185.3g(540mmol)、4,4′−ジクロロベンゾフェノン15. 1g(60mmol)、ヨウ化ナトリウム11.7g(78mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド11.8g(18mmol)、トリフェニルホスフィン63.0g(240mmol)、亜鉛94.1g(1.44mol)を冷却管、三方コックを取り付けた三口フラスコに入れ、70℃のオイルバスにつけ、窒素置換後、窒素雰囲気下にN−メチル−2−ピロリドン1000mlを加え、反応を開始した。20時間反応後、N−メチル−2−ピロリドン500mlで希釈し、1/10重量比の塩酸/メタノール溶液に重合反応液を注ぎ、ポリマーを析出、洗浄後、ろ過、真空乾燥後、白色の粉末を得た。収量は、153gであった。また、重量平均分子量は、159000であった。このポリマー150gに対し、濃硫酸1500mlを加え室温で24時間、攪拌しスルホン化反応を行った。反応後、大量の純水中に注ぎ、スルホン化ポリマーを析出させた。pH7になるまでポリマーを純水によって洗浄し、ろ過後、スルホン化ポリマーを回収し、90℃で真空乾燥した。スルホン化ポリマーの収量は179gであった。このポリマーのイオン交換容量は2.3meq/g、重量平均分子量は183,000であった。このようにして得られたポリマーは、構造式(E)で表される。スルホン酸基を有する重合体を、ポリマーRAとする。
上記で得られたスルホン化重合体RAを、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)スルホン化重合体RBの合成
攪拌機、温度計、窒素導入管をとりつけた1Lの三口フラスコに、3−(2,5−ジクロロベンゾイル)ベンゼンスルホン酸ネオペンチル141.5g(337mmol)、[実施例2-2](1)で得られたMn10,500の疎水性ユニットB48.5g(4.6mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド6.71g(10.3mmol)、ヨウ化ナトリウム1.54g(10.3mmol)、トリフェニルホスフィン35.9g(137mmol)、亜鉛53.7g(821mmol)をはかりとり、乾燥窒素置換した。ここにN,N-ジメチルアセトアミド(DMAc)430mLを加え、反応温度を80℃に保持しながら3時間攪拌を続けた後、DMAc730mLを加えて希釈し、不溶物を濾過した。
上記で得られたスルホン化重合体RBを、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)スルホン化重合体RCの合成
乾燥したN,N−ジメチルアセトアミド(DMAc)100mLを上記構造式C−2で表される化合物モノマーC 27.18g(38.5mmol)と、[実施例2-3](1)で合成した疎水性ユニット16.58g(1.48mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド0.79g(1.2mmol)、トリフェニルホスフィン4.20g(16.0mmol)、ヨウ化ナトリウム0.18g(1.20mmol)、亜鉛6.28g(96.1mmol)の混合物中に窒素下で加えた。
上記で得られたスルホン化重合体RCを、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
(1)スルホン化重合体RDの合成
攪拌機、温度計、窒素導入管をとりつけた1Lの三口フラスコに、3−(2,5−ジクロロベンゾイル)ベンゼンスルホン酸ネオペンチル134.6g(336mmol)と、
(1)で合成した疎水性ユニットD47.4g(6.5mmol)、ビス(トリフェニルホスフィン)ニッケルジクロリド6.71g(10.3mmol)、トリフェニルホスフィン35.9g(136mmol)、ヨウ化ナトリウム1.54g(10.3mmol)、亜鉛53.7g(820mmol)をはかりとった。これに、乾燥したN,N−ジメチルアセトアミド(DMAc)430mLを窒素下で加えた。
上記で得られたスルホン化重合体RDを、メタノール/NMP=50/50の混合溶媒に15重量%になるよう溶解し、ワニスを調製した。これをキャスト法により、キャスト膜を調製し、大量の蒸留水への浸漬により、膜中の残存NMPを希釈により除去し、目的の40μmの膜を得た。得られた膜を用いて、比抵抗、耐熱性評価を行った。結果を表1に示す。
Claims (5)
- 主鎖がポリフェニレン構造であり、スルホン酸基を有する側鎖と含窒素複素環基を有する側鎖とを有する構造を含み、
含窒素複素環基を有する側鎖が下記一般式(D)で表される構造であり、
前記含窒素複素環基がピロール、チアゾール、イソチアゾール、オキサゾール、イソオキサゾール、ピリジン、イミダゾール、イミダゾリン、ピラゾール、1,3,5−トリアジン、ピリミジン、ピリタジン、ピラジン、インドール、キノリン、イソキノリン、ブリン、ベンズイミダゾール、ベンズオキサゾール、ベンズチアゾール、テトラゾール、テトラジン、トリアゾール、カルバゾール、アクリジン、キノキサリン、キナゾリンからなる含窒素複素環化合物およびこれらの誘導体からなる群から選ばれる化合物から誘導される少なくとも1種の基であることを特徴とする重合体。 - スルホン酸基を有する側鎖が下記一般式(E)で表される請求項1に記載の重合体。
- 下記一般式(C)で表される繰り返し構造単位、および下記一般式(A)で表される繰り返し単位を含むことを特徴とする請求項1に記載の重合体。
- さらに下記一般式(B)で表される構造を有することを特徴とする請求項3に記載の重合体。
- 請求項1〜4のいずれかに記載の重合体からなるプロトン伝導膜。
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JP2012082204A (ja) | 2012-04-26 |
US7906608B2 (en) | 2011-03-15 |
KR101007815B1 (ko) | 2011-01-14 |
EP1905791A1 (en) | 2008-04-02 |
JPWO2007010731A1 (ja) | 2009-01-29 |
CA2615494A1 (en) | 2007-01-25 |
KR20100021008A (ko) | 2010-02-23 |
KR101007744B1 (ko) | 2011-01-14 |
EP1905791A4 (en) | 2009-09-23 |
US20090149623A1 (en) | 2009-06-11 |
WO2007010731A1 (ja) | 2007-01-25 |
EP2206547A1 (en) | 2010-07-14 |
CA2615494C (en) | 2011-08-09 |
CN101223208A (zh) | 2008-07-16 |
CN101223208B (zh) | 2012-06-06 |
EP2206547B1 (en) | 2016-03-16 |
KR20080028489A (ko) | 2008-03-31 |
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