JP7010500B2 - 安定性ポリ(イミダゾリウム)ヒドロキシド - Google Patents
安定性ポリ(イミダゾリウム)ヒドロキシド Download PDFInfo
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- JP7010500B2 JP7010500B2 JP2019504901A JP2019504901A JP7010500B2 JP 7010500 B2 JP7010500 B2 JP 7010500B2 JP 2019504901 A JP2019504901 A JP 2019504901A JP 2019504901 A JP2019504901 A JP 2019504901A JP 7010500 B2 JP7010500 B2 JP 7010500B2
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- Prior art keywords
- alkyl
- heteroalkyl
- perfluoroalkyl
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- ion
- Prior art date
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 title description 14
- 229920000642 polymer Polymers 0.000 claims description 173
- 125000000217 alkyl group Chemical group 0.000 claims description 165
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 144
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 143
- 125000003118 aryl group Chemical group 0.000 claims description 93
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 69
- 125000002883 imidazolyl group Chemical group 0.000 claims description 65
- -1 perfluoroalkylene Chemical group 0.000 claims description 59
- 150000001450 anions Chemical class 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 230000007935 neutral effect Effects 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000000732 arylene group Chemical group 0.000 claims description 27
- 125000005549 heteroarylene group Chemical group 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 24
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 16
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229920000554 ionomer Polymers 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229940124530 sulfonamide Drugs 0.000 claims description 10
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000000446 fuel Substances 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 229940063013 borate ion Drugs 0.000 claims 3
- 229940006460 bromide ion Drugs 0.000 claims 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- 229940085991 phosphate ion Drugs 0.000 claims 3
- 229940006158 triiodide ion Drugs 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 241000609666 Tuber aestivum Species 0.000 claims 2
- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 claims 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 41
- 239000000203 mixture Substances 0.000 description 36
- 239000012528 membrane Substances 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 229920000889 poly(m-phenylene isophthalamide) Polymers 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 150000001721 carbon Chemical class 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000000354 decomposition reaction Methods 0.000 description 21
- 238000006731 degradation reaction Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 230000015556 catabolic process Effects 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 17
- 150000004679 hydroxides Chemical class 0.000 description 17
- 150000004694 iodide salts Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 16
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 238000010520 demethylation reaction Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 230000017858 demethylation Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000003775 Density Functional Theory Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000003518 caustics Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 235000011007 phosphoric acid Nutrition 0.000 description 8
- 238000007142 ring opening reaction Methods 0.000 description 8
- 230000007704 transition Effects 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 239000007857 degradation product Substances 0.000 description 7
- 238000007069 methylation reaction Methods 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 150000003456 sulfonamides Chemical class 0.000 description 7
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
- 239000005695 Ammonium acetate Substances 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 6
- 229940043376 ammonium acetate Drugs 0.000 description 6
- 235000019257 ammonium acetate Nutrition 0.000 description 6
- 230000006652 catabolic pathway Effects 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 230000011987 methylation Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000004693 imidazolium salts Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 150000001649 bromium compounds Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 3
- YDYNSAUGVGAOLO-UHFFFAOYSA-N 2,6-dibromobenzaldehyde Chemical compound BrC1=CC=CC(Br)=C1C=O YDYNSAUGVGAOLO-UHFFFAOYSA-N 0.000 description 3
- XDNKBLDOPXNQHQ-UHFFFAOYSA-N 2-(2,6-dibromophenyl)-4,5-diphenyl-1H-imidazole Chemical compound BrC1=C(C(=CC=C1)Br)C=1NC(=C(N=1)C1=CC=CC=C1)C1=CC=CC=C1 XDNKBLDOPXNQHQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000003637 basic solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229920006317 cationic polymer Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012847 fine chemical Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical compound OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QLWOUBCORTYSPP-UHFFFAOYSA-N 1h-imidazol-1-ium;hydroxide Chemical compound O.C1=CNC=N1 QLWOUBCORTYSPP-UHFFFAOYSA-N 0.000 description 2
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 description 2
- OZHORAJMZLQJHO-UHFFFAOYSA-N 2-(2,6-dibromophenyl)-1-methyl-4,5-diphenylimidazole Chemical compound Cn1c(nc(c1-c1ccccc1)-c1ccccc1)-c1c(Br)cccc1Br OZHORAJMZLQJHO-UHFFFAOYSA-N 0.000 description 2
- HNQWOVAJIPYVTC-UHFFFAOYSA-N 2-(2,6-diphenylphenyl)-1-methyl-4,5-diphenylimidazole Chemical compound Cn1c(nc(c1-c1ccccc1)-c1ccccc1)-c1c(cccc1-c1ccccc1)-c1ccccc1 HNQWOVAJIPYVTC-UHFFFAOYSA-N 0.000 description 2
- GHWCNWQBTMHJKU-UHFFFAOYSA-N 3-bromo-2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1Br GHWCNWQBTMHJKU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005284 basis set Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000011066 ex-situ storage Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
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Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Inert Electrodes (AREA)
- Fuel Cell (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662368667P | 2016-07-29 | 2016-07-29 | |
| US62/368,667 | 2016-07-29 | ||
| PCT/US2017/044554 WO2018023097A1 (en) | 2016-07-29 | 2017-07-29 | Stable ply(imidazolium) hydroxides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019532116A JP2019532116A (ja) | 2019-11-07 |
| JP2019532116A5 JP2019532116A5 (OSRAM) | 2020-08-20 |
| JP7010500B2 true JP7010500B2 (ja) | 2022-01-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019504901A Active JP7010500B2 (ja) | 2016-07-29 | 2017-07-29 | 安定性ポリ(イミダゾリウム)ヒドロキシド |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US11299464B2 (OSRAM) |
| EP (1) | EP3490976B1 (OSRAM) |
| JP (1) | JP7010500B2 (OSRAM) |
| CN (1) | CN109923104B (OSRAM) |
| AU (1) | AU2017301884B2 (OSRAM) |
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| CA3009698A1 (en) * | 2016-01-08 | 2017-07-13 | Simon Fraser University | Poly(phenylene) and m-terphenyl as protecting groups for benzimidazolium hydroxides |
| CA3032403A1 (en) * | 2016-08-04 | 2018-02-08 | Simon Fraser University | Crosslinking of hydroxide stable, polybenzimidazoliums and polyimidazoliums membranes and ionomers |
| CN111848520B (zh) * | 2020-08-10 | 2022-02-22 | 中国科学院长春应用化学研究所 | 一种咪唑鎓盐单体及其制备方法和聚合物电解质材料及其制备方法和应用 |
| US20250032680A1 (en) | 2021-03-19 | 2025-01-30 | Ionomr Innovations, Inc. | Antiviral and antimicrobial coatings and methods thereof |
| CN115109235B (zh) * | 2022-07-18 | 2023-07-04 | 烟台九目化学股份有限公司 | 一种咪唑型基团功能化的聚合物及其制备方法和应用 |
| CN115181250B (zh) * | 2022-08-10 | 2023-07-04 | 烟台九目化学股份有限公司 | 一种侧链咪唑功能化的聚合物及其制备方法和应用 |
| EP4424665A1 (en) | 2023-03-03 | 2024-09-04 | Agfa-Gevaert Nv | Cationic compounds for anion exchange membranes |
| US20250145769A1 (en) * | 2023-11-03 | 2025-05-08 | Ionomr Innovations Inc. | Cross-linked arylimidazolium polymers and uses thereof |
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| WO2015157848A1 (en) | 2014-04-15 | 2015-10-22 | Simon Fraser University | Hydroxide-stable ionenes |
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| KR100411465B1 (ko) | 2001-10-26 | 2003-12-18 | 한국과학기술연구원 | 폴리페닐렌을 갖는 플로렌계 화합물, 그 중합체 및 이들을포함하는 el 소자 |
| US7301002B1 (en) | 2003-10-14 | 2007-11-27 | Sandia Corporation | Sulfonated polyphenylene polymers |
| JP4565879B2 (ja) | 2004-04-19 | 2010-10-20 | ルネサスエレクトロニクス株式会社 | 半導体装置 |
| KR100612873B1 (ko) | 2004-11-20 | 2006-08-14 | 삼성에스디아이 주식회사 | 금속 촉매와 전극의 제조방법 |
| JP2009087687A (ja) | 2007-09-28 | 2009-04-23 | Sanyo Chem Ind Ltd | ガス電極 |
| WO2009134227A1 (en) | 2008-05-02 | 2009-11-05 | Energy Materials Corporation | Pol yarylene polymers resulting from diels-alder reaction |
| US8110636B1 (en) | 2009-04-17 | 2012-02-07 | Sandia Corporation | Multi-block sulfonated poly(phenylene) copolymer proton exchange membranes |
| US8926732B2 (en) | 2009-07-24 | 2015-01-06 | The Regents Of The University Of Colorado, A Body Corporate | Imidazolium-based room-temperature ionic liquids, polymers, monomers, and membranes incorporating same |
| JP2012128142A (ja) | 2010-12-15 | 2012-07-05 | Konica Minolta Business Technologies Inc | トナーの製造方法およびトナー |
| US9263524B2 (en) | 2011-04-05 | 2016-02-16 | The Board Of Trustees Of The Leland Stanford Junior University | Semiconductor materials, apparatuses and methods |
| KR101293196B1 (ko) | 2011-04-11 | 2013-08-05 | 한국과학기술연구원 | 폴리벤즈이미다졸리움 및 폴리벤즈이미다졸리움 기반 고체 전해질 |
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Also Published As
| Publication number | Publication date |
|---|---|
| PL3490976T3 (pl) | 2023-11-20 |
| PT3490976T (pt) | 2023-08-08 |
| CN109923104B (zh) | 2022-12-06 |
| JP2019532116A (ja) | 2019-11-07 |
| ES2952539T3 (es) | 2023-11-02 |
| US20190382353A1 (en) | 2019-12-19 |
| HRP20230899T1 (hr) | 2023-11-24 |
| EP3490976B1 (en) | 2023-06-07 |
| LT3490976T (lt) | 2023-09-25 |
| US11299464B2 (en) | 2022-04-12 |
| WO2018023097A8 (en) | 2018-05-24 |
| WO2018023097A1 (en) | 2018-02-01 |
| CA3032388A1 (en) | 2018-02-01 |
| AU2017301884A1 (en) | 2019-02-14 |
| HUE062710T2 (hu) | 2023-11-28 |
| FI3490976T3 (fi) | 2023-08-21 |
| DK3490976T3 (da) | 2023-08-21 |
| AU2017301884B2 (en) | 2021-06-24 |
| EP3490976A1 (en) | 2019-06-05 |
| EP3490976A4 (en) | 2020-04-01 |
| CN109923104A (zh) | 2019-06-21 |
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