CN102695741B - 具有季铵官能团的降冰片烯类聚合物 - Google Patents
具有季铵官能团的降冰片烯类聚合物 Download PDFInfo
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- CN102695741B CN102695741B CN201080055973.5A CN201080055973A CN102695741B CN 102695741 B CN102695741 B CN 102695741B CN 201080055973 A CN201080055973 A CN 201080055973A CN 102695741 B CN102695741 B CN 102695741B
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- monomer
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- 229920000642 polymer Polymers 0.000 title claims abstract description 53
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 15
- 239000000446 fuel Substances 0.000 claims abstract description 24
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 15
- 150000001450 anions Chemical class 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims description 46
- -1 methyl glycol ethers Chemical class 0.000 claims description 28
- 239000012528 membrane Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 150000002848 norbornenes Chemical class 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000003011 anion exchange membrane Substances 0.000 abstract description 37
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 abstract description 22
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000000178 monomer Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- 239000000126 substance Substances 0.000 description 29
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 27
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000005574 norbornylene group Chemical group 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000002390 rotary evaporation Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 238000012644 addition polymerization Methods 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000007246 mechanism Effects 0.000 description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001412 amines Chemical group 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 4
- 239000004913 cyclooctene Substances 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 229940059936 lithium bromide Drugs 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229920000867 polyelectrolyte Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 241000370738 Chlorion Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- UBUYAZUEYAXMBU-UHFFFAOYSA-N azane;n,n-dimethylmethanamine Chemical compound N.CN(C)C UBUYAZUEYAXMBU-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 3
- 239000004914 cyclooctane Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 238000003487 electrochemical reaction Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000012041 precatalyst Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- QSFLNLJGDOMXIK-UHFFFAOYSA-N 1,5-dibromooctane Chemical compound CCCC(Br)CCCCBr QSFLNLJGDOMXIK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- WLWGTACLCJNFRC-UHFFFAOYSA-N 2-n,4-n,4-n-trimethylpentane-2,4-diamine Chemical compound CNC(C)CC(C)N(C)C WLWGTACLCJNFRC-UHFFFAOYSA-N 0.000 description 2
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002788 crimping Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical class [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- BDFXEIRNKZFBFT-UHFFFAOYSA-N 1,13-dibromotridecane Chemical compound BrCCCCCCCCCCCCCBr BDFXEIRNKZFBFT-UHFFFAOYSA-N 0.000 description 1
- WPBWUVCMCYXPFI-UHFFFAOYSA-N 1,2,5,6-Tetrabromohexane Chemical compound BrCC(Br)CCC(Br)CBr WPBWUVCMCYXPFI-UHFFFAOYSA-N 0.000 description 1
- WQEQYRFDVUEATJ-UHFFFAOYSA-N 1,2,6-tribromohexane Chemical compound BrCCCCC(Br)CBr WQEQYRFDVUEATJ-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 1
- XZNGUVQDFJHPLU-UHFFFAOYSA-N 1,3-dibromobutane Chemical compound CC(Br)CCBr XZNGUVQDFJHPLU-UHFFFAOYSA-N 0.000 description 1
- GHRIWTBUXMUHJM-UHFFFAOYSA-N 1,3-diiodopentane Chemical compound CCC(I)CCI GHRIWTBUXMUHJM-UHFFFAOYSA-N 0.000 description 1
- AAAXMNYUNVCMCJ-UHFFFAOYSA-N 1,3-diiodopropane Chemical compound ICCCI AAAXMNYUNVCMCJ-UHFFFAOYSA-N 0.000 description 1
- IAEOYUUPFYJXHN-UHFFFAOYSA-N 1,5-diiodopentane Chemical compound ICCCCCI IAEOYUUPFYJXHN-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 1
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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| US28399409P | 2009-12-11 | 2009-12-11 | |
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| US12/966,768 US8765893B2 (en) | 2009-12-11 | 2010-12-13 | Norbornene-type polymers having quaternary ammonium functionality |
| PCT/US2010/060144 WO2011072304A2 (en) | 2009-12-11 | 2010-12-13 | Norbornene-type polymers having quaternary ammonium functionality |
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| CN102516256A (zh) * | 2011-07-21 | 2012-06-27 | 沈阳药科大学 | 一种环氧异吲哚酮类衍生物的制备方法 |
| JP2014084349A (ja) * | 2012-10-22 | 2014-05-12 | Nitto Denko Corp | アニオン伝導性高分子電解質膜およびその製造方法ならびにそれを用いた膜電極接合体および燃料電池 |
| US9447220B2 (en) | 2012-11-19 | 2016-09-20 | Rohm And Haas Electronic Materials Llc | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| US9223214B2 (en) | 2012-11-19 | 2015-12-29 | The Texas A&M University System | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| CA2905943A1 (en) * | 2013-03-13 | 2014-10-02 | Fluidic, Inc. | Hetero-ionic aromatic additives for electrochemical cells comprising a metal fuel |
| US10078261B2 (en) * | 2013-09-06 | 2018-09-18 | Rohm And Haas Electronic Materials Llc | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| US9405189B2 (en) | 2013-09-06 | 2016-08-02 | Rohm And Haas Electronic Materials Llc | Self-assembled structures, method of manufacture thereof and articles comprising the same |
| CN103923282B (zh) * | 2014-01-08 | 2018-04-06 | 南开大学 | 含多金属氧酸盐‑倍半硅氧烷的共聚物及制备方法 |
| TWI579333B (zh) * | 2015-12-28 | 2017-04-21 | 財團法人工業技術研究院 | 離子交換膜 |
| TWI583708B (zh) | 2015-12-28 | 2017-05-21 | 財團法人工業技術研究院 | 聚合物及其製備方法 |
| CN106866497B (zh) * | 2017-01-22 | 2019-05-14 | 中北大学 | 一种降冰片烯类化合物及其制备方法和应用 |
| CN108341964B (zh) * | 2017-01-23 | 2021-04-06 | 多氟多化工股份有限公司 | 一种功能聚合物、锂电池用聚合物电解质及制备方法、聚合物电解质膜、锂离子电池 |
| CN108400347B (zh) * | 2018-03-09 | 2021-02-09 | 新乡学院 | 一种交联型聚苯并咪唑质子交换膜的制备方法 |
| US12410289B2 (en) * | 2018-10-05 | 2025-09-09 | Rensselaer Polytechnic Institute | Preparation of ion exchange membranes from polyolefins and polycyclic olefins |
| CN111063931B (zh) * | 2018-10-16 | 2021-02-05 | 多氟多化工股份有限公司 | 一种固态聚合物电解质及其应用 |
| CN109535062B (zh) * | 2019-01-10 | 2021-03-23 | 中北大学 | 一种降冰片烯类两性离子单体及其制备方法 |
| US12037255B2 (en) * | 2019-08-27 | 2024-07-16 | ExxonMobil Technology and Engineering Company | Zeolite syntheses using diquaternary structure directing agents |
| CN110746561A (zh) * | 2019-11-07 | 2020-02-04 | 合肥工业大学 | 一种含多季铵阳离子基团的聚合物及其制备方法和应用 |
| CN112928316A (zh) * | 2019-12-05 | 2021-06-08 | 西安交通大学 | 一种高离子传导率、高机械性能的阴离子交换薄膜的制备方法 |
| US11597784B2 (en) | 2020-03-30 | 2023-03-07 | Saudi Arabian Oil Company | Enhanced yield, structural control, and transport properties of polynorbornenes for natural gas upgrading through Mizoroki-Heck cross-couplings |
| BR112023001457A2 (pt) * | 2020-07-30 | 2023-04-11 | Promerus Llc | Polímeros policilolefínicos e membranas de permuta aniônica derivados desses |
| CN115591418B (zh) * | 2022-12-14 | 2023-06-09 | 佛山(华南)新材料研究院 | 一种捕集二噁英的隔膜及其制备方法 |
| TW202440749A (zh) * | 2022-12-20 | 2024-10-16 | 美商普羅梅勒斯有限公司 | 藉由熱和uv引發塊狀聚合之支撐膜 |
| CN116031456B (zh) * | 2023-01-06 | 2025-05-16 | 武汉大学 | 一种高稳定性碱性聚电解质及其制备方法 |
| CN116217805B (zh) * | 2023-01-07 | 2024-08-02 | 中北大学 | 一种降冰片烯基三铵类阳离子聚合物及其制备方法和应用 |
| CN116284916B (zh) * | 2023-02-23 | 2025-05-09 | 中北大学 | 一种聚降冰片烯类阴离子交换膜及其制备方法 |
| CN116284691B (zh) * | 2023-03-27 | 2023-11-17 | 天津大学 | 一种具有抑菌性高透明的离子型环烯烃共聚物及其制备方法 |
| WO2025035152A2 (en) * | 2023-08-10 | 2025-02-13 | Cornell University | Thermoset materials and methods of making and using same |
| CN119528846B (zh) * | 2024-02-08 | 2025-10-10 | 北京清玮膜科技有限公司 | 一种聚降冰片烯基互穿聚合物网络交联阴离子交换膜及其制备方法和应用 |
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| US7329758B1 (en) * | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| US6838489B2 (en) | 2001-03-23 | 2005-01-04 | Cymetech, Llc | High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor |
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| US20060020068A1 (en) * | 2004-07-07 | 2006-01-26 | Edmund Elce | Photosensitive compositions based on polycyclic polymers for low stress, high temperature films |
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| WO2004074933A2 (en) * | 2003-02-20 | 2004-09-02 | Promerus Llc | Dissolution rate modifiers for photoresist compositions |
| JP4180404B2 (ja) * | 2003-03-05 | 2008-11-12 | アイシン精機株式会社 | 燃料電池、酸化剤配流板 |
| JP5089986B2 (ja) * | 2003-11-28 | 2012-12-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機半導体層およびその改善 |
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| GB0329812D0 (en) * | 2003-12-23 | 2004-01-28 | Amersham Plc | Romp polymer synthesis |
| JP4503394B2 (ja) * | 2004-08-13 | 2010-07-14 | 富士通株式会社 | 燃料電池システム及び電気機器、並びに、燃料電池システムにおける発生水の回収方法 |
| US7875686B2 (en) * | 2004-08-18 | 2011-01-25 | Promerus Llc | Polycycloolefin polymeric compositions for semiconductor applications |
| JP4993867B2 (ja) * | 2005-03-07 | 2012-08-08 | ダイハツ工業株式会社 | 燃料電池 |
| US7439275B2 (en) * | 2005-03-24 | 2008-10-21 | Los Alamos National Security, Llc | Anion-conducting polymer, composition, and membrane |
| US20070259236A1 (en) * | 2006-05-03 | 2007-11-08 | Lang Christopher M | Anionic fuel cells, hybrid fuel cells, and methods of fabrication thereof |
| JP2008088247A (ja) * | 2006-09-29 | 2008-04-17 | Univ Of Tokyo | フルオロスルホニル基を有するノルボルネン重合体の製造方法、スルホン酸基を有する重合体および該重合体を用いた燃料電池用電解質膜 |
| EP2140510A1 (en) * | 2007-04-25 | 2010-01-06 | Merck Patent GmbH | Process for preparing an electronic device |
| US20110250525A1 (en) * | 2007-08-23 | 2011-10-13 | Tokuyama Corporation | Separation membrane for direct liquid fuel cell and method for producing the same |
| JP2009256654A (ja) * | 2008-03-27 | 2009-11-05 | Sumitomo Chemical Co Ltd | 高分子電解質組成物 |
| US8026041B2 (en) * | 2008-04-02 | 2011-09-27 | Eastman Kodak Company | Imageable elements useful for waterless printing |
| JP5719514B2 (ja) * | 2009-02-08 | 2015-05-20 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 上塗りフォトレジストと共に使用するのに好適なコーティング組成物 |
| US9493397B2 (en) | 2009-05-29 | 2016-11-15 | Cornell University | Ionomers and methods of making same and uses thereof |
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| WO2011072304A2 (en) | 2011-06-16 |
| CN102695741A (zh) | 2012-09-26 |
| EP2510036A2 (en) | 2012-10-17 |
| JP2013513705A (ja) | 2013-04-22 |
| US20110143260A1 (en) | 2011-06-16 |
| WO2011072304A3 (en) | 2011-10-06 |
| KR20120123663A (ko) | 2012-11-09 |
| US8765893B2 (en) | 2014-07-01 |
| JP5964236B2 (ja) | 2016-08-03 |
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