TWI576368B - 製備聚合物、塗佈電極之方法及相關聚合物與電極 - Google Patents
製備聚合物、塗佈電極之方法及相關聚合物與電極 Download PDFInfo
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- TWI576368B TWI576368B TW099128674A TW99128674A TWI576368B TW I576368 B TWI576368 B TW I576368B TW 099128674 A TW099128674 A TW 099128674A TW 99128674 A TW99128674 A TW 99128674A TW I576368 B TWI576368 B TW I576368B
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- Prior art keywords
- formula
- salt
- electrode
- acid
- sulfonic acid
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- 238000000034 method Methods 0.000 title claims description 31
- 229920000642 polymer Polymers 0.000 title claims description 27
- 238000000576 coating method Methods 0.000 title claims description 8
- 239000011248 coating agent Substances 0.000 title claims description 7
- 239000000178 monomer Substances 0.000 claims description 37
- -1 sulfoalkyl ester Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 11
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 9
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 235000013877 carbamide Nutrition 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims description 6
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000009736 wetting Methods 0.000 claims description 5
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 4
- YKULZXPRVBECFM-UHFFFAOYSA-N Cl.Cl.N(=NN=C(NCC(C)C)N)N=C(NCC(C)C)N Chemical group Cl.Cl.N(=NN=C(NCC(C)C)N)N=C(NCC(C)C)N YKULZXPRVBECFM-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 4
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 3
- IAXXETNIOYFMLW-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) 2-methylprop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C(=C)C)CC1C2(C)C IAXXETNIOYFMLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- TWYISXLZCIVDDW-UHFFFAOYSA-N 2-methyl-n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C(C)=C TWYISXLZCIVDDW-UHFFFAOYSA-N 0.000 claims description 2
- NYUTUWAFOUJLKI-UHFFFAOYSA-N 3-prop-2-enoyloxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC(=O)C=C NYUTUWAFOUJLKI-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- KCTMTGOHHMRJHZ-UHFFFAOYSA-N n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C=C KCTMTGOHHMRJHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- YVDPOVXIRVBNAL-UHFFFAOYSA-J tetrapotassium;phosphonatooxy phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OOP([O-])([O-])=O YVDPOVXIRVBNAL-UHFFFAOYSA-J 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- OKRKCRJAKWNPSU-UHFFFAOYSA-N N-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound C(O)NC(C(=C)C)=O.C(O)NC(C(=C)C)=O OKRKCRJAKWNPSU-UHFFFAOYSA-N 0.000 claims 1
- NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 229960002317 succinimide Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920001169 thermoplastic Polymers 0.000 description 7
- 239000004416 thermosoftening plastic Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
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- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000010997 low field NMR spectroscopy Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UMSFRTCUQPFZFA-UHFFFAOYSA-N 3-(3-sulfopropoxycarbonyl)but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCCCS(O)(=O)=O UMSFRTCUQPFZFA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- 238000005265 energy consumption Methods 0.000 description 1
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- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001307 helium Chemical group 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical group [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
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- 150000002500 ions Chemical class 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
- 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
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 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
- 238000010998 test method Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
離子交換聚合物係用於諸多應用中，例如，製造用於離子分離過程之離子交換薄膜或塗層。製備離子交換聚合物之常見技術涉及非離子性、非水溶性之二乙烯系交聯劑(例如，二乙烯苯)與單體(如苯乙烯)於非水性溶劑(如二乙苯)中之聚合。用溶劑(如二氯乙烯)平衡或清洗所得之(例如呈片或薄膜形式之)固體聚合物數次，以移除並取代該二乙苯溶劑。其中需要陽離子交換薄膜時，隨後使該等薄膜與三氧化硫與二氯乙烯之溶液反應，以形成磺酸鹽基，緊接著其經甲醇清洗且經碳酸氫鈉中和後，提供給該聚合物強鹼性離子交換性能。該等水不溶性單體及於非水性溶劑中進行之聚合反應及後續反應需要化學處置伴隨該等有機溶劑損失之問題。
已開發於水性溶劑系統中可聚合之水溶性交聯劑，以克服上述問題。該聚合物之交聯藉由兩種單體之間的縮合反應發生且與該聚合同時進行，因此無需二乙烯系單體。與此同時，消除了石油衍生溶劑之費用及其處置問題。
然而，大多數目前可獲得之水溶性交聯劑係昂貴且非環境友好型。同時，某些應用(例如超級電容器電極)偏好具有低電阻、低膨脹率及良好的塗層形態且可經塗佈以減少能源消耗並提高該等電極之電流效率之聚合物。
因此，需要一種自水溶性、廉價及環境友好的材料製造低膨脹率聚合物之方法及一種用該聚合物塗佈電極之方法，以減少該電極之電阻並提高其電流效率。
根據本文所述之實施例，提供一種方法，其包括：共聚合包含至少兩個醯胺基之單體、式(a)單體、及磺酸或鹽單體，其中R1係CH3或H。
根據本文所述之實施例，亦提供一種由以上方法製得之聚合物及一種包含該聚合物之薄膜。
根據本文所述之實施例，提供一種塗佈電極之方法，其包括：提供電極；提供自由基起始劑、包含至少兩個醯胺基之單體、式(a)單體及磺酸或鹽單體之溶液；用該溶液潤濕該電極；及加熱該潤濕電極；藉此使該包含至少兩個醯胺基之單體、該式(a)單體、及該磺酸或鹽單體共聚合；其中R1係CH3或H。
根據本文所述之實施例，提供一種藉由以上方法塗佈之電極。
在整篇說明書及申請專利範圍中，本文使用之估計語言可適用於修飾任何定量描述，其在不造成相關基本功能之變化下，可容許地變化。因此，由術語(如「約」或「實質上」)修飾之值係不限於指定之精確值。在某些情況下，估計語言可對應於測量該值之儀器的精確度。
根據本文所述之實施例，提供一種方法，其包括：共聚合包含至少兩個醯胺基之單體、式(a)單體、及磺酸或鹽單體，其中R1係CH3或H。
在另一態樣中，提供一種由該方法製得之聚合物及一種包含該聚合物之薄膜。
根據本文所述之實施例，提供一種塗佈電極之方法，其包括：提供電極；提供自由基起始劑、包含至少兩個醯胺基之單體、式(a)單體及磺酸或鹽單體之溶液；用該溶液潤濕該電極；及加熱該潤濕電極；藉此使該包含至少兩個醯胺基之單體、該式(a)單體、及該磺酸或鹽單體共聚合；其中R1係CH3或H。
根據本文所述之實施例，提供一種藉由以上方法塗佈之電極。
適宜的式(a)單體單元係(例如)水溶性、乙烯系不飽和化合物，其可藉由自由基聚合並含有N-羥甲基(-NH-CH2OH)或其醚化衍生物(-NH-CH2OR，其中R=C1-C6烷基)。較佳的單體單元係N-羥甲基丙烯醯胺(N-(羥甲基)丙烯醯胺，NMA)、N-羥甲基甲基丙烯醯胺(NMMA)、N-(異丁氧基甲基)-丙烯醯胺(IBMA)、N-(異丁氧基甲基)-甲基丙烯醯胺及N-(正丁氧基甲基)-丙烯醯胺(NBMA)。特佳的單體單元係N-羥甲基丙烯醯胺及N-(異丁氧基甲基)-丙烯醯胺。
在某些實施例中，該磺酸或鹽單體係式(b)：
其中R2係CH3或H；X係NH或O且Y係烷基。適宜的磺酸或鹽單體係(例如)水溶性、乙烯系不飽和化合物，其可藉由自由基聚合並含有磺酸或磺酸鹽基-SO3M，其中M=H或鹼金屬、銨或鹼土金屬離子。較佳的單體單元係2-丙烯醯胺基-2-甲基丙磺酸、苯乙烯磺酸、(甲基)丙烯酸磺烷基酯類、衣康酸磺烷基酯類，較佳係在各情況中，具有C1至C6烷基、及乙烯基磺酸及其銨鹽、鹼金屬鹽或鹼土金屬鹽。特佳的單體單元係2-丙烯醯胺基-2-甲基丙磺酸、苯乙烯磺酸、對苯乙烯磺酸、丙烯酸磺丙酯、衣康酸磺丙酯及乙烯基磺酸及其銨、鈉、鉀及鈣鹽。
本文使用之術語「烷基」係指飽和烴基。適宜的烷基實例包括正丁基、正戊基、正庚基、異丁基、第三丁基、及異戊基。
在某些實施例中，該包含至少兩個醯胺基之單體係選自羰基二胺及式(c)化合物，其中R3係NH、脂族基或醚單元。
本文使用之術語「脂族基」係指具有至少一種由非環狀之直鏈或分支鏈原子排列組成之價態之有機基。脂族基係定義為包含至少一個碳原子。包含該脂族基之原子排列可包括雜原子(如氮、硫、矽、硒及氧)或可僅由碳及氫組成。為了方便，該術語「脂族基」在本文中係定義為涵蓋經寬廣範圍之官能基(如烷基、烯基、炔基、鹵代烷基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基、醯基(例如，羧酸衍生物，如酯類及醯胺類)、胺基、硝基、及類似物)取代之有機基(作為該「非環狀之直鏈或分支鏈原子排列」之部份)。例如，4-甲基戊-1-基係包含甲基之C6脂族基，該甲基係烷基官能基。類似地，4-硝基丁-1-基係包含硝基之C4脂族基，該硝基係官能基。脂族基可係包含一或多個可係相同或不同的鹵原子之鹵代烷基。鹵原子包括(例如)氟、氯、溴、及碘。包含一或多個鹵原子之脂族基包括烷基鹵化物三氟甲基、溴二氟甲基、氯二氟甲基、六氟亞異丙基、氯甲基、二氟亞乙烯基、三氯甲基、溴二氯甲基、溴乙基、2-溴三亞甲基(例如，-CH2CHBrCH2-)、及類似物。脂族基之其他實例包括烯丙基、胺基羰基(即，-CONH2)、羰基、2,2-二氰基亞異丙基(即，-CH2C(CN)2CH2-)、甲基(即，-CH3)、亞甲基(即，-CH2-)、乙基、亞乙基、甲醯基(即，-CHO)、己基、六亞甲基、羥甲基(即，-CH2OH)、巰甲基(即，-CH2SH)、甲硫基(即，-SCH3)、甲硫基甲基(即，-CH2SCH3)、甲氧基、甲氧基羰基(即，CH3OCO-)、硝基甲基(即，-CH2NO2)、硫羰基、三甲基矽烷基(即，(CH3)3Si-)、第三丁基二甲基矽烷基、3-三甲氧基矽烷基丙基(即，(CH3O)3SiCH2CH2CH2-)、乙烯基、亞乙烯基、及類似物。經由其他實例，C1至C10脂族基含有至少一個但是不多於10個碳原子。甲基(即，CH3-)係C1脂族基之實例。癸基(即，CH3(CH2)9-)係C10脂族基之實例。
本文使用之術語「醚單元」係指鍵結至氧之經取代或未經取代之伸烷基基團，且一般對應於式-C(R4)2-C(R4)2-O-，其中R4在各情況下分別為氫、鹵素、硝基、氰基、C1-20烴基或經一或多個以下各者取代之C1-20烴基：鹵素、氰基、硝基、硫烷基、第三胺基、烷氧基、芳氧基、芳烷氧基、羰基二氧烷基、羰基二氧芳基、羰基二氧芳烷基、烷氧基羰基、芳氧基羰基、芳烷氧基羰基、烷基羰基、芳基羰基、芳烷基羰基、烷基亞磺醯基、芳基亞磺醯基、芳烷基亞磺醯基、烷基磺醯基、芳基磺醯基，或芳烷基磺醯基。
本文使用之術語「醯胺基」係指-R5CONH2基，其中R5係氫或烷基。
在某些實施例中，該包含至少兩個醯胺基之單體係選自雙縮脲及丁二醯胺。
本文之水溶性一般意指在23℃下，於水中之溶解度係至少10重量%。
較佳地，藉由在較佳係40℃至80℃之反應溫度下，於水性溶液中之自由基聚合進行根據本發明之共聚物之製備。可藉由最初將該反應混合物之全部或個別成分引入反應槽中，或藉由最初將一部份該等組分引入及補足該反應混合物之該等成分或個別成份進行該聚合。
藉由習知水溶性試劑(其形成自由基)進行啟動，該試劑的較佳用量係基於該等單體總重量之0.01至3.0重量%。彼等之實例係過硫酸銨及過硫酸鉀、2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽、過氧化氫、及過氧二磷酸鉀、鈉及銨。如果合適，亦可以已知方式將述及之自由基起始劑與基於該等單體總重量的0.01至1.0重量%之還原劑組合，在此情況下，其可能使該聚合在較低溫度下進行。例如，鹼金屬甲醛次硫酸鹽及抗壞血酸係適宜的。
併入以下實例來為熟悉本技藝者在實踐本發明時提供額外的引導。因此，該等實例並不如隨附申請專利範圍中所定義般限制本發明。
在強烈攪拌下，將2-丙烯醯胺基-2-甲基-1-丙烷磺酸(20g，購自Sigma-Aldrich®)、28g N-(羥甲基)丙烯醯胺及8.3g尿素(羰基二胺)與44g去離子水混合在一起。待該等單體充分溶解後，將1g 2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽添加至該溶液中，並攪拌該溶液直至2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽溶解。
2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽係購自Sigma-Aldrich®。N-(羥甲基)丙烯醯胺及尿素係購自Sinopharm Chemical Reagent Co,Ltd.，中國上海。
將藉由壓製壓延活性碳片材於Ti網格上製備並夾於兩片聚(對苯二甲酸乙二醇酯)(PET)膜(16 cm*32 cm)中之碳電極(16 cm*32 cm*1.0 mm)密封入熱塑性袋中，同時在該熱塑性袋上留3個小開口(直徑為10 mm)為打開狀態。經由該等開口將製備之溶液添加至該熱塑性袋中。隨後，將整個熱塑性袋夾於兩片玻璃板材(24 cm*40 cm)之間，有U型橡膠墊圈(17 cm*34 cm)位於該熱塑性袋與該玻璃板材之間，以確保整個電極表面浸入該溶液中。將該組裝件放入真空櫃中並脫氣6分鐘，以加速該溶液潤濕該電極。之後，將該組裝件自該真空櫃中取出並將該U型墊圈自其拆下。將過量溶液自該熱塑性袋中擠出，並使用夾子以夾住該兩片玻璃板材使彼此相對。將新組裝件放入80℃之烘箱中2.5小時。
該新組裝件冷卻下來後，將經塗佈之電極取出，且測出其厚度為1.1 mm，而未經塗佈之裸電極為1.0 mm。自該熱塑性袋中取出一些乾聚合物碎片樣品，以測試該聚合物之膨脹率及-SO3 -密度。於組裝電池中，測試該電極之電阻及電流效率。
將乾聚合物樣品0.327 g放入小瓶中，並將1.129 g蒸餾水添加至該瓶中。24小時之後，用低場NMR測試該膨脹樣品。兩種質子信號出現於低場NMR光譜中。一種係因為吸附水(膨脹水)且另一種係因為游離水。游離水信號與游離水質子強度具有線性關係，即，藉由改變水飽和聚合物樣品中之水的總量，得到游離水信號強度之對應變化。因此，獲得游離水含量與游離水質子強度的回歸函數。通過該回歸函數，自游離水質子強度計算得游離水含量係0.669 g。吸附水含量係如下計算：吸附水=全部水-游離水=1.129 g-0.669 g=0.46 g。膨脹率(重量)=(吸附水/乾聚合物)*100%=0.46/0.327*100%=140%。
將乾聚合物(1.32 g)浸泡於HCl溶液(200 ml,1 N)中24小時。用去離子水沖洗浸泡聚合物，直至濾液變成中性。隨後，將該聚合物放入NaCl溶液(100 ml，1 N)中，來使它平衡24小時。取出10 ml平衡溶液，並用NaOH溶液(0.01 N)滴定該10 ml平衡溶液。-SO3 -密度=ΔVNaOH*0.01 N*10/乾聚合物=(23.5*0.01*10)/1.32=1.78毫莫耳/克乾聚合物。
將該塗佈電極與反裸碳電極組裝，同時將聚合物流動間隔片(尺寸：16 cm*24 cm，厚度：0.7 mm)(其係藉由熱壓製聚合物網格進入乙烯醋酸乙烯酯(EVA)聚合物膜中以形成流動通道製得)夾於該等兩個電極之間，以測試其於1600 ppm NaCl溶液中之電阻。使用Land電池測試儀CT2001B及CT2001D(購自Wuhan Jinnuo Electronics Co.,Ltd.，中國武漢)來測試且該電荷電流係1250 mA。
該塗佈電極電阻係計算如下：電阻=電池電阻-溶液電阻-反電極電阻。經由Land電池測試儀CT2001B及CT2001D獲得電池電阻(電池電阻=Δ電壓/電流=0.125/1.25=0.10 Ohm)。經由溶液導電率計算溶液電阻(溶液電阻=1/導電率*厚度=1/3.2*0.07=0.02 Ohm)。使用與該塗佈電極相同的測試方法，在兩個相同的裸碳電極電池中，預測試反電極電阻，其中電池電阻=0.12 Ohm且溶液電阻係0.02 Ohm。該反電極電阻=(0.12-0.02)/2=0.05 Ohm。因此，塗佈電極電阻=0.10-0.02-0.05=0.03 Ohm。
為了比較研究，將傳統的經IX薄膜修飾之碳電極(其中將一片IX薄膜(CR-67,GE Water & Process Technologies,Watertown,MA,US)附接至裸碳電極上)與裸碳電極組裝，同時將聚合物流動間隔片(尺寸：16 cm*24 cm，厚度：0.7 mm)夾於該等兩個電極之間，以測試其於1600 ppm NaCl溶液中之電阻。使用Land電池測試儀CT2001B及CT2001D且該電荷電流為1250 mA。
經IX薄膜修飾之碳電極電阻=電池電阻-溶液電阻-反電極電阻。電池電阻=Δ電壓/電流=0.24/1.25=0.19 Ohm。溶液電阻=1/導電率*厚度=1/3.2*0.07=0.02 Ohm。反電極電阻=(0.12-0.02)/2=0.05 Ohm。因此，該經IX薄膜修飾之碳電極電阻=0.19-0.02-0.05=0.12 Ohm。
該塗佈電極電阻係15.36 Ohm*cm2(0.03 Ohm*512 cm2)，而經IX薄膜修飾之碳電極為61.44 Ohm*cm2(0.12*500 cm2)。
亦在二電極電池中，於1600 ppm NaCl中測試電流效率。電流效率=(移除鹽之莫耳數*96500庫侖/莫耳)/(總使用電荷之庫侖數)。經由計算溶液導電率自原溶液至稀釋溶液之變化獲得該移除鹽之莫耳數，為4.4 mmol。經由該Land電池測試儀CT2001B及CT2001D讀出總使用電荷，為450庫侖。因此，電流效率=(移除鹽之莫耳數*96500庫侖/莫耳)/(總使用電荷之庫侖數)=(4.4*96500*0.001/450)*100%=94.4%。
本文所述之實施例係具有對應於申請專利範圍中所列之本發明元件之元件的組合物、結構、系統及方法之實例。此份書面說明可使熟悉本技藝者製造並使用具有同樣對應於申請專利範圍中所列之本發明元件之替代元件的實施例。因此，本發明範疇包括無不同於該等申請專利範圍之字面語言之組合物、結構、系統及方法，且進一步包括與該等申請專利範圍之字面語言有非實質差異之其他結構、系統及方法。雖然，本文僅闡述及描述了某些特徵及實施例，但是熟悉相關技術者可進行諸多修改及變化。隨附申請專利範圍涵蓋所有此等修改及變化。
Claims (16)
- 一種方法，其包括共聚合選自羰基二胺及式 (c)化合物，其中R3係NH、脂族基或醚單元之包含至少兩個醯胺基之單體、式(a)單體，其中R1係CH3或H、及式(b) 之磺酸或鹽單體，其中R2係CH3或H；X係NH或O且Y係烷基。
- 如請求項1之方法，其中該磺酸或鹽單體係2-丙烯醯胺基-2-甲基丙磺酸。
- 如請求項1之方法，其中該磺酸或鹽單體係2-丙烯醯胺基-2-甲基丙磺酸、苯乙烯磺酸、(甲基)丙烯酸磺烷基酯類、衣康酸磺烷基酯類，其具有C1至C6烷基、或乙烯基磺酸及其銨鹽、鹼金屬或鹼土金屬鹽。
- 如請求項1之方法，其中該磺酸或鹽單體係2-丙烯醯胺基-2-甲基丙磺酸、苯乙烯磺酸、對苯乙烯磺酸、丙烯酸磺丙酯、衣康酸磺丙酯或乙烯基磺酸及其銨、鈉、鉀及鈣鹽。
- 如請求項1之方法，其中該式(a)單體係N-羥甲基丙烯醯胺(N-(羥甲基)丙烯醯胺，NMA)、N-羥甲基甲基丙烯醯胺(NMMA)、N-(異丁氧基甲基)-丙烯醯胺(IBMA)、N- (異丁氧基甲基)-甲基丙烯醯胺或N-(正丁氧基甲基)-丙烯醯胺(NBMA)。
- 如請求項1之方法，其中該包含至少兩個醯胺基之單體係選自雙縮脲及丁二醯胺。
- 如請求項1之方法，其另外包括在自由基起始劑之存在下之共聚合。
- 如請求項7之方法，其中該自由基起始劑包括過硫酸銨或鉀、2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽、過氧化氫、或過氧二磷酸鉀、鈉或銨。
- 一種藉由如請求項1之方法製得之聚合物，其中該聚合物之膨脹率為140%且-SO3 -密度為1.78毫莫耳/克乾聚合物。
- 一種塗佈電極之方法，其包括：提供電極；提供自由基起始劑、選自羰基二胺及式 (c)化合物，其中R3係NH、脂族基或醚單元之包含至少兩個醯胺基之單體、式 (a)單體，其中R1係CH3或H、及式(b) 之磺酸或鹽單體之溶液，其中 R2係CH3或H；X係NH或O且Y係烷基；用該溶液潤濕該電極；及加熱該潤濕電極；藉此使該包含至少兩個醯胺基之單體、該式(a)單體、及該式(b)之磺酸或鹽單體共聚合。
- 如請求項10之方法，其中該磺酸或鹽單體係2-丙烯醯胺基-2-甲基丙磺酸。
- 如請求項10之方法，其中該磺酸或鹽單體係對苯乙烯磺酸。
- 如請求項10之方法，其中該式(a)單體係N-(羥甲基)丙烯醯胺。
- 如請求項10之方法，其中該自由基起始劑係2,2'-(偶氮雙(2-甲基丙基脒))二鹽酸鹽、過硫酸銨、或過硫酸鉀。
- 如請求項10之方法，其中該包含至少兩個醯胺基之單體係羰基二胺。
- 一種藉由如請求項10之方法塗佈之電極。
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