JP2023027293A - 水溶性アニオン交換体材料 - Google Patents
水溶性アニオン交換体材料 Download PDFInfo
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- JP2023027293A JP2023027293A JP2022200406A JP2022200406A JP2023027293A JP 2023027293 A JP2023027293 A JP 2023027293A JP 2022200406 A JP2022200406 A JP 2022200406A JP 2022200406 A JP2022200406 A JP 2022200406A JP 2023027293 A JP2023027293 A JP 2023027293A
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- Prior art keywords
- chloride
- water
- insoluble
- anion
- exchanger material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000463 material Substances 0.000 title claims abstract description 56
- 150000001450 anions Chemical class 0.000 title claims abstract description 38
- 238000005349 anion exchange Methods 0.000 claims abstract description 43
- -1 diallyl ammonium salt Chemical class 0.000 claims abstract description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 229920003176 water-insoluble polymer Polymers 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229920006393 polyether sulfone Polymers 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000004695 Polyether sulfone Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 239000000470 constituent Substances 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 108091006522 Anion exchangers Proteins 0.000 claims description 7
- UBJVUCKUDDKUJF-UHFFFAOYSA-N Diallyl sulfide Chemical compound C=CCSCC=C UBJVUCKUDDKUJF-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 claims description 6
- 229920001774 Perfluoroether Polymers 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 5
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 5
- 239000004743 Polypropylene Substances 0.000 claims description 5
- 229920002492 poly(sulfone) Polymers 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- 229920001955 polyphenylene ether Polymers 0.000 claims description 5
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 5
- 229920001155 polypropylene Polymers 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 3
- PQVDTVNAMGYHDQ-UHFFFAOYSA-N 1,2-bis(prop-2-enyl)benzene Chemical compound C=CCC1=CC=CC=C1CC=C PQVDTVNAMGYHDQ-UHFFFAOYSA-N 0.000 claims description 3
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims description 3
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical compound C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 claims description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005012 alkyl thioether group Chemical group 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000004832 aryl thioethers Chemical class 0.000 claims description 3
- OSXWETDBWKSBFH-UHFFFAOYSA-N diphenyl-bis(prop-2-enyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](CC=C)(CC=C)C1=CC=CC=C1 OSXWETDBWKSBFH-UHFFFAOYSA-N 0.000 claims description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 3
- 150000004694 iodide salts Chemical class 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- BLYOHBPLFYXHQA-UHFFFAOYSA-N n,n-bis(prop-2-enyl)prop-2-enamide Chemical compound C=CCN(CC=C)C(=O)C=C BLYOHBPLFYXHQA-UHFFFAOYSA-N 0.000 claims description 3
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 claims description 3
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003003 phosphines Chemical group 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- 229960000834 vinyl ether Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 2
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- 229920002490 poly(thioether-sulfone) polymer Polymers 0.000 claims description 2
- 150000003842 bromide salts Chemical class 0.000 claims 2
- KUXKWCPBFHIJJJ-UHFFFAOYSA-N 6-hydroxy-2-methylhex-2-enoic acid Chemical compound OC(=O)C(C)=CCCCO KUXKWCPBFHIJJJ-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229920003169 water-soluble polymer Polymers 0.000 claims 1
- 239000003011 anion exchange membrane Substances 0.000 abstract description 14
- 239000003957 anion exchange resin Substances 0.000 abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000012528 membrane Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000005342 ion exchange Methods 0.000 description 6
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 229940058401 polytetrafluoroethylene Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003384 small molecules Chemical group 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- SKQMFJIXLDJWPM-UHFFFAOYSA-M 1,1-bis(prop-2-enyl)pyrrolidin-1-ium;bromide Chemical compound [Br-].C=CC[N+]1(CC=C)CCCC1 SKQMFJIXLDJWPM-UHFFFAOYSA-M 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- OUKZUIOFTUUCEN-UHFFFAOYSA-N 7$l^{6}-thiabicyclo[4.1.0]hepta-1,3,5-triene 7,7-dioxide Chemical compound C1=CC=C2S(=O)(=O)C2=C1 OUKZUIOFTUUCEN-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- JAFLFWVBZWUEDL-UHFFFAOYSA-N [I-].[NH4+].C1=CC=CC=2C3=CC=CC=C3C12.C1=CC=CC=2C3=CC=CC=C3C12 Chemical compound [I-].[NH4+].C1=CC=CC=2C3=CC=CC=C3C12.C1=CC=CC=2C3=CC=CC=C3C12 JAFLFWVBZWUEDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/08—Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/12—Macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F126/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F126/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F126/08—N-Vinyl-pyrrolidine
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
・R1は窒素及び/又はリンであり、
・R2~R9は置換基であり、ここで
R2及びR3は水素であるか、又は少なくとも1つの基R2及びR3が水素でない場合、R2及び/又はR3はアルキル基又はアリール基であり、
R4及びR5はそれぞれ、アルキル基及び/又はアリール基であり、
R6~R9は水素であるか、又は少なくとも1つの基R6~R9が水素でない場合、これらの基R6~R9はアルキル基又はアリール基であり、
・Zは末端基であり、
・Xは結合部であり、
・Vは架橋部であり、
・Kは末端基Z又は結合部Xであり、
・Dは存在しないか、又は少なくとも1つのメチレン基若しくは酸素若しくは硫黄であり、
・Bは温度安定性及びアルカリ安定性を示す非水溶性ポリマーであり、
・Aは官能基を有さないコモノマーであり、
・2≦n≦100であり、
・m=0又は1であり、
・1≦o≦100であり、
・50モル%≦x≦99モル%であり、かつy=(100モル%-x)であり、
・10モル%≦w≦100モル%であり、かつ(n+w)=100モル%である)
のうち少なくとも1つによる構造単位の構成要素であり、
ここで、
・Kの場合、少なくとも1つの末端基Z及び少なくとも1つの結合部Xが存在しており、
・アニオン交換基Cが、一般式I~IVによる構造単位の構成要素として、1つ以上若しくは全ての結合部Xを介して非水溶性ポリマーBと繋がっており、実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、
かつ/又は
・アニオン交換基Cが、一般式V~VIIIによる構造単位の構成要素として、架橋部Vを介して相互に架橋しており、実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、結合部Xである全てのKが化学的な共有結合によって非水溶性ポリマーBと繋がっており、
かつ/又は
・アニオン交換基C及び非水溶性ポリマーBが一つ以上のイオン結合によって接続している。
・R1は窒素及び/又はリンであり、
・R2~R9は置換基であり、ここで
R2及びR3は水素であるか、又は少なくとも1つの基R2及びR3が水素でない場合、R2及び/又はR3はアルキル基又はアリール基であり、
R4及びR5はそれぞれ、アルキル基及び/又はアリール基であり、
R6~R9は水素であるか、又は少なくとも1つの基R6~R9が水素でない場合、これらの基R6~R9はアルキル基又はアリール基であり、
・Zは末端基であり、
・Xは結合部であり、
・Vは架橋部であり、
・Kは末端基Z又は結合部Xであり、
・Dは存在しないか、又は少なくとも1つのメチレン基若しくは酸素若しくは硫黄であり、
・Bは非水溶性ポリマーであり、
・Aは官能基を有さないコモノマーであり、
・2≦n≦100であり、
・m=0又は1であり、
・1≦o≦100であり、
・50モル%≦x≦99モル%であり、かつy=(100モル%-x)であり、
・10モル%≦w≦100モル%であり、かつ(n+w)=100モル%である)
のうち少なくとも1つによる構造単位の構成要素である。
・Kの場合、少なくとも1つの末端基Z及び少なくとも1つの結合部Xが存在しており、
・アニオン交換基Cが、一般式I~IVによる構造単位の構成要素として、1つ以上若しくは全ての結合部Xを介して非水溶性ポリマーBと繋がっており、実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、
かつ/又は
・アニオン交換基Cが、一般式V~VIIIによる構造単位の構成要素として、架橋部Vを介して相互に架橋しており、実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、結合部Xである全てのKが化学的な共有結合によって非水溶性ポリマーBと繋がっており、
かつ/又は
・アニオン交換基C及び非水溶性ポリマーBが一つ以上のイオン結合によって接続している。
一般式IIによる構造単位における複数のアニオン交換基C(非水溶性ポリマーBを介する結合部を有する)からアニオン交換膜を製造。
質量
試験前=0.5g、試験後=0.49g
イオン交換容量
試験前=1.30mmol/g、試験後=1.29mmol/g
水酸化物イオン伝導性(80℃、95%の相対湿度)
試験前=70mS/cm、試験後=69mS/cm。
一般式VIによる構造単位の構成要素である複数のアニオン交換基C(非水溶性ポリマーBを介する結合部を有する)を有する架橋化合物からアニオン交換膜を製造。
質量
試験前=0.5g、試験後=0.49g
イオン交換容量
試験前=3.35mmol/g、試験後=3.32mmol/g
水酸化物イオン伝導性(80℃、95%の相対湿度)
試験前=90mS/cm、試験後=88mS/cm。
Claims (15)
- 少なくとも、相互に直鎖状に重合した、及び/又は分枝した、及び/又は架橋したアニオン交換基Cからなる非水溶性アニオン交換体材料であって、前記アニオン交換基Cは、以下の一般式I~VIII:
・R1は窒素及び/又はリンであり、
・R2~R9は置換基であり、
R2及びR3は水素であるか、又は少なくとも1つの基R2及びR3が水素でない場合、R2及び/又はR3はアルキル基又はアリール基であり、かつ
R4及びR5はそれぞれ、アルキル基及び/又はアリール基であり、かつ
R6~R9は水素であるか、又は少なくとも1つの基R6~R9が水素でない場合、これらの基R6~R9はアルキル基又はアリール基であり、かつ
・Zは末端基であり、かつ
・Xは結合部であり、かつ
・Vは架橋部であり、かつ
・Kは末端基Z又は結合部Xであり、かつ
・Dは存在しないか、又は少なくとも1つのメチレン基若しくは酸素若しくは硫黄であり、かつ
・Bは温度安定性及びアルカリ安定性を示す非水溶性ポリマーであり、かつ
・Aは官能基を有していないコモノマーであり、かつ
・2≦n≦100であり、かつ
・m=0又は1であり、かつ
・1≦o≦100であり、かつ
・50モル%≦x≦99モル%であり、かつy=(100モル%-x)であり、かつ
・10モル%≦w≦100モル%であり、かつ(n+w)=100モル%である)
の少なくとも1つによる構造単位の構成要素であり、
ここで、
・Kの場合、少なくとも1つの末端基Z及び少なくとも1つの結合部Xが存在しており、
・アニオン交換基Cが、一般式I~IVによる構造単位の構成要素として、1つ以上若しくは全ての結合部Xを介して非水溶性ポリマーBと結合しており、かつ実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、
かつ/又は
・アニオン交換基Cが、一般式V~VIIIによる構造単位の構成要素として、架橋部Vを介して相互に架橋しており、かつ実質的に全ての末端基Zが、温度安定性及びアルカリ安定性を示す化合物であり、結合部Xである全てのKが化学的な共有結合によって非水溶性ポリマーBと結合しており、
かつ/又は
・アニオン交換基C及び非水溶性ポリマーBが一つ以上のイオン結合によって接続している、
前記非水溶性アニオン交換体材料。 - 請求項1に記載の非水溶性アニオン交換体材料であって、式I~IVによる少なくとも2つのアニオン交換基Cが、非水溶性ポリマーBと結合部Xを介して化学的な共有結合によって相互に結合しており、かつ/又はアニオン交換基Cが、イオン結合によって非水溶性ポリマーBと接続しており、かつ末端基Zが、温度安定性及びアルカリ安定性を示す化合物である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、結合部Xが、N,N-ジアリルピペリジニウムエーテル、又はN,N-ジアリルピロリジニウムエーテル、又はN,N-ジアリルアミノエチルエーテル、又はメタクリルアミドエチルエーテル、又はメタクリル酸エステル、又はメタクリル酸ヒドロキシプロピルエーテル、又はキシリレンエーテル、又はフェニレンエーテルスルホンである前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、式V~VIIIによるアニオン交換基Cが架橋部Vを介して架橋しており、かつKが結合部Xであり、これに非水溶性ポリマーBが化学的な共有結合によって結合している前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、末端基Zが、アルキルチオエーテル、又はアリールチオエーテル、又はベンジルチオエーテルである前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、温度安定性及びアルカリ安定性を示す非水溶性ポリマーBが、ポリエーテルスルホン、又はポリスルホン、又はポリチオエーテルスルホン、又はポリフェニレン、又はポリフェニレンエーテル、又はポリフェニレンスルフィド、又はポリ(ペルフルオロエチレンプロピレン)、又はポリテトラフルオロエチレン、又はポリ(エチレン-テトラフルオロエチレン)、又はペルフルオロアルコキシポリマー、又はポリスチレン、又はポリエチレン、又はポリプロピレンであるか、又はポリエーテルスルホン、又はポリスルホン、又はポリフェニレン、又はポリフェニレンエーテル、又はポリフェニレンスルフィド、又はポリ(ペルフルオロエチレンプロピレン)、又はポリテトラフルオロエチレン、又はポリ(エチレン-テトラフルオロエチレン)、又はペルフルオロアルコキシポリマー、又はポリスチレン、又はポリエチレン、又はポリプロピレンの部類をスルホン化及び/若しくはカルボキシル化及び/若しくはホスホン化したポリマーである前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、コモノマーAが、スチレン、及び/又はα-メチルスチレン、及び/又はN-ビニルカルバゾール、及び/又はメタクリルエステル、及び/又はN-ビニルピロリドン、及び/又はN,N-ジアリルアクリルアミド、及び/又はN,N-ジアリルアクリルスルホンアミド、及び/又はジアリルエーテル、及び/又は1,2-ジアリルベンゼン、及び/又はジアリルスルフィド、及び/又はクロロトリフルオロエチレン、及び/又はテトラフルオロエチレン、及び/又はヘキサフルオロプロピレン、及び/又は1,2-ジビニルベンゼンである前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、架橋部Vが、テトラアリルアンモニウムクロリド、又はテトラアルキルアリルアンモニウムクロリド、又はジアリル-ジアルキルアリルアンモニウムクロリド、又は1,4-ジビニルベンゼン、又はジビニルスルホン、又はジビニルスルフィド、又はジビニルスルホキシド、又はジビニルエーテル、又はジアクリルアミド、又はジメタクリルアミド、又はN,N,N’,N’-テトラアリル-4,4’-トリメチレンジピペリジニウムクロリド、又はN,N,N’,N’-テトラアルキルアリル-4,4’-トリメチレンジピペリジニウムクロリド、又はN,N-ジアリル-,N’,N’-ジアルキルアリル-4,4’-トリメチレンジピペリジニウムクロリド、又はN-アリル-N,N’,N’-トリアルキルアリル-4,4’-トリメチレンジピペリジニウムクロリド、又はN,N,N’-トリアリル-N’-アルキルアリル-4,4’-トリメチレンジピペリジニウムクロリド、又はN,N,N’,N’-テトラアリルピペラジニウムクロリド、又はN,N,N’,N’-テトラアルキルアリルピペラジニウムクロリド、又はN,N-ジアリル-N’,N’-ジアルキルアリルピペラジニウムクロリド、又はN-アリル-N,N’,N’-トリアルキルアリルピペラジニウムクロリド、又はN,N,N’-トリアリル-N’-アルキルアリルピペラジニウムクロリド、及び/又はこれらの化合物の臭化物及び/若しくはヨウ化物である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、アニオン交換基Cを製造するためのモノマーとして、脂肪族若しくは芳香族若しくは脂環式の第二級アミンのN,N-ジアリル化合物、及び/又はN,N-ジアルキルアリル化合物、及び/又はN-アリル-N-アルキルアリル化合物、例えば、ジアリルジメチルアンモニウムクロリド、ジアリルピペリジニウムクロリド、ジアリルピロリジニウムクロリド、アリル-メタリルジメチルアンモニウムクロリド、アリル-メタリルピペリジニウムクロリド、アリル-メタリルピロリジニウムクロリド、ジメタリルジメチルアンモニウムクロリド、ジメタリルピペリジニウムクロリド、ジメチルアリルピロリジニウムクロリド、ジアリル-3,4-ジメチルピロリジニウムクロリド、ジアリル-3,3,4,4-テトラメチルピロリジニウムクロリド、ジアリル-3,5-ジメチルピペリジニウムクロリド、ジアリル-3,3,5,5-テトラメチルピペリジニウムクロリド、ジアリル-ジフェニルアンモニウムクロリド、脂肪族若しくは芳香族若しくは脂環式の第二級ホスフィンのP,P-ジアリル化合物、及び/又はP,P-ジアルキルアリル化合物、及び/又はP-アリル-P-アルキルアリル化合物、例えば、ジアリルジメチルホスホニウムクロリド、ジアリルジフェニルホスホニウムクロリド、及び/又はこれらの化合物の臭化物及び/若しくはヨウ化物が使用されている前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、R1が窒素である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、R2及び/又はR3がメチル基及び/又は水素である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、R4及びR5がアルキル基であり、有利にはメチル基又はエチル基である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、R6~R9が水素である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、10≦n≦50である前記非水溶性アニオン交換体材料。
- 請求項1に記載の非水溶性アニオン交換体材料であって、2≦o≦10である前記非水溶性アニオン交換体材料。
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