CN1926131A - 杂环接枝单体和相关聚合物以及杂化无机-有机聚合物膜 - Google Patents
杂环接枝单体和相关聚合物以及杂化无机-有机聚合物膜 Download PDFInfo
- Publication number
- CN1926131A CN1926131A CNA2005800064394A CN200580006439A CN1926131A CN 1926131 A CN1926131 A CN 1926131A CN A2005800064394 A CNA2005800064394 A CN A2005800064394A CN 200580006439 A CN200580006439 A CN 200580006439A CN 1926131 A CN1926131 A CN 1926131A
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- CN
- China
- Prior art keywords
- compound
- group
- triazole
- heterocyclic ring
- nitrogen heterocyclic
- 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.)
- Granted
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 78
- 229920000642 polymer Polymers 0.000 title claims abstract description 53
- 239000012528 membrane Substances 0.000 title abstract description 11
- 229920000620 organic polymer Polymers 0.000 title description 6
- 239000000178 monomer Substances 0.000 title description 5
- 239000000446 fuel Substances 0.000 claims abstract description 18
- 239000000126 substance Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- -1 imidazolium halide Chemical class 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 28
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 22
- 230000002378 acidificating effect Effects 0.000 claims description 22
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 17
- 150000002460 imidazoles Chemical class 0.000 claims description 16
- 150000003852 triazoles Chemical group 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 14
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000005647 linker group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 10
- 229920001940 conductive polymer Polymers 0.000 claims description 10
- 150000003217 pyrazoles Chemical class 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 230000026030 halogenation Effects 0.000 claims description 7
- 238000005658 halogenation reaction Methods 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000000177 1,2,3-triazoles Chemical class 0.000 claims description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 4
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- 238000010586 diagram Methods 0.000 description 44
- 239000000243 solution Substances 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 30
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000002047 photoemission electron microscopy Methods 0.000 description 25
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- 239000002243 precursor Substances 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000013019 agitation Methods 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000007766 curtain coating Methods 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 6
- 229920002492 poly(sulfone) Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RYQOCVLJCNCZOZ-UHFFFAOYSA-N 2-but-3-enyl-5-(trifluoromethyl)-1h-imidazole Chemical class FC(F)(F)C1=CN=C(CCC=C)N1 RYQOCVLJCNCZOZ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000012990 dithiocarbamate Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical class SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 229940008075 allyl sulfide Drugs 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 150000002894 organic compounds Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
- WYTQXLFLAMZNNZ-UHFFFAOYSA-N 3-trihydroxysilylpropane-1-sulfonic acid Chemical compound O[Si](O)(O)CCCS(O)(=O)=O WYTQXLFLAMZNNZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000557 Nafion® Polymers 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000019086 sulfide ion homeostasis Effects 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000002769 thiazolinyl group Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ODMMNALOCMNQJZ-UHFFFAOYSA-N 1H-pyrrolizine Chemical compound C1=CC=C2CC=CN21 ODMMNALOCMNQJZ-UHFFFAOYSA-N 0.000 description 2
- PULQXRCSWKSPFZ-UHFFFAOYSA-N 2-(2,6-dimethylhept-5-enyl)-5-(trifluoromethyl)-1h-imidazole Chemical class CC(C)=CCCC(C)CC1=NC=C(C(F)(F)F)N1 PULQXRCSWKSPFZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- HUHVNLKXTMBFIR-UHFFFAOYSA-N CC1=CCC(C=C1)(CCl)O Chemical compound CC1=CCC(C=C1)(CCl)O HUHVNLKXTMBFIR-UHFFFAOYSA-N 0.000 description 2
- AYSRNXUMGODKHP-UHFFFAOYSA-N CC1=CCC(C=C1)(CN=[N+]=[N-])O Chemical compound CC1=CCC(C=C1)(CN=[N+]=[N-])O AYSRNXUMGODKHP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 206010013786 Dry skin Diseases 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
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- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical class CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000007789 gas Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
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- 238000003780 insertion Methods 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 238000007254 oxidation reaction Methods 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
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- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- VPKVKBZXORVFIU-UHFFFAOYSA-N 1-fluoroimidazole Chemical class FN1C=CN=C1 VPKVKBZXORVFIU-UHFFFAOYSA-N 0.000 description 1
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- VNFYMAPAENTMMO-UHFFFAOYSA-N 5-chloro-2-methylquinoline Chemical compound ClC1=CC=CC2=NC(C)=CC=C21 VNFYMAPAENTMMO-UHFFFAOYSA-N 0.000 description 1
- MHQZDNQHLGFBRN-UHFFFAOYSA-N 5-ethenyl-1h-imidazole Chemical class C=CC1=CNC=N1 MHQZDNQHLGFBRN-UHFFFAOYSA-N 0.000 description 1
- FZRITSUNJKWMKD-UHFFFAOYSA-N 5-pent-4-enylsulfanyl-1h-1,2,4-triazole Chemical compound C=CCCCSC1=NC=NN1 FZRITSUNJKWMKD-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
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- ZRJMKQIDQFKUJY-UHFFFAOYSA-N C(CCC)C1(SCC=N1)C1=NC=CN=C1 Chemical compound C(CCC)C1(SCC=N1)C1=NC=CN=C1 ZRJMKQIDQFKUJY-UHFFFAOYSA-N 0.000 description 1
- ACPLYHQEIMTLCO-UHFFFAOYSA-N CCCCC1(C(N2)=NC=C2F)SCC=N1 Chemical class CCCCC1(C(N2)=NC=C2F)SCC=N1 ACPLYHQEIMTLCO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
Claims (39)
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US11/044,527 US7576165B2 (en) | 2004-01-27 | 2005-01-26 | Heterocycle grafted monomers and related polymers and hybrid inorganic-organic polymer membranes |
PCT/US2005/002922 WO2005072413A2 (en) | 2004-01-27 | 2005-01-27 | Heterocycle grafted monomers and related polymers and hybrid inorganic-organic polymer membranes |
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CN1926131B CN1926131B (zh) | 2012-10-31 |
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JP (1) | JP5171042B2 (zh) |
CN (1) | CN1926131B (zh) |
CA (1) | CA2555273C (zh) |
WO (1) | WO2005072413A2 (zh) |
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CN101821889A (zh) * | 2007-09-26 | 2010-09-01 | 法国原子能及替代能源委员会 | 用于燃料电池的具有质子梯度的质子传导膜及所述膜的制备方法 |
CN103346341A (zh) * | 2013-06-08 | 2013-10-09 | 上海大学 | 酸碱复合型高温质子交换膜及其制备方法 |
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CN108598532A (zh) * | 2018-05-29 | 2018-09-28 | 中国科学院上海有机化学研究所 | 一种燃料电池用有机膦酸高温质子交换膜及其制备方法 |
CN108666603A (zh) * | 2018-05-29 | 2018-10-16 | 中国科学院上海有机化学研究所 | 一种有机膦酸高温质子交换膜及其制备方法 |
CN108767298A (zh) * | 2018-05-29 | 2018-11-06 | 中国科学院上海有机化学研究所 | 一种有机高分子交联的有机膦酸高温质子交换膜及其制备方法 |
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CN108779275A (zh) * | 2016-02-03 | 2018-11-09 | 坎麦克斯动力有限责任公司 | 双极性离聚物膜 |
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US20060083976A1 (en) * | 2004-06-09 | 2006-04-20 | California Institute Of Technology | Substituted nitrogen heterocycles as proton carriers for water-free proton exchange membranes for fuel cells |
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CA2555273A1 (en) | 2005-08-11 |
EP1713794B1 (en) | 2014-05-07 |
WO2005072413A3 (en) | 2006-03-30 |
JP5171042B2 (ja) | 2013-03-27 |
EP1713794A2 (en) | 2006-10-25 |
JP2007523066A (ja) | 2007-08-16 |
CA2555273C (en) | 2014-10-28 |
CN1926131B (zh) | 2012-10-31 |
US7576165B2 (en) | 2009-08-18 |
US20060111530A1 (en) | 2006-05-25 |
EP1713794A4 (en) | 2010-04-28 |
WO2005072413A2 (en) | 2005-08-11 |
WO2005072413A8 (en) | 2006-06-29 |
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