CN101837253A - 含二氮杂萘酮结构聚芳醚酮酮阴离子交换膜及其制备方法 - Google Patents
含二氮杂萘酮结构聚芳醚酮酮阴离子交换膜及其制备方法 Download PDFInfo
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- CN101837253A CN101837253A CN 201010141349 CN201010141349A CN101837253A CN 101837253 A CN101837253 A CN 101837253A CN 201010141349 CN201010141349 CN 201010141349 CN 201010141349 A CN201010141349 A CN 201010141349A CN 101837253 A CN101837253 A CN 101837253A
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- ketone
- naphthyridine
- halomethylation
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- exchange membrane
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- 229920006260 polyaryletherketone Polymers 0.000 title claims abstract description 65
- 150000002576 ketones Chemical class 0.000 title claims abstract description 54
- 239000003011 anion exchange membrane Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical group C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 title abstract 9
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 238000005576 amination reaction Methods 0.000 claims abstract description 15
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000768 polyamine Polymers 0.000 claims abstract description 6
- 238000005266 casting Methods 0.000 claims abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 125000000468 ketone group Chemical group 0.000 claims description 11
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- -1 halomethyl alkyl ether Chemical class 0.000 claims description 6
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- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
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- 238000005406 washing Methods 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- YUMNZEWYPUBSQA-UHFFFAOYSA-N 1-(chloromethoxy)octane Chemical compound CCCCCCCCOCCl YUMNZEWYPUBSQA-UHFFFAOYSA-N 0.000 claims description 3
- 229940061627 chloromethyl methyl ether Drugs 0.000 claims description 3
- RTSBCGFVAMIDBC-UHFFFAOYSA-N 1-(bromomethoxy)butane Chemical compound CCCCOCBr RTSBCGFVAMIDBC-UHFFFAOYSA-N 0.000 claims description 2
- PMGWYOXUKDCMNK-UHFFFAOYSA-N 1-(bromomethoxy)octane Chemical compound CCCCCCCCOCBr PMGWYOXUKDCMNK-UHFFFAOYSA-N 0.000 claims description 2
- NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 2
- JAMFGQBENKSWOF-UHFFFAOYSA-N bromo(methoxy)methane Chemical compound COCBr JAMFGQBENKSWOF-UHFFFAOYSA-N 0.000 claims description 2
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- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
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- 235000005074 zinc chloride Nutrition 0.000 claims description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 210000002469 basement membrane Anatomy 0.000 description 6
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- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000000909 electrodialysis Methods 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 5
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- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 238000010612 desalination reaction Methods 0.000 description 3
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- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000005862 Whey Substances 0.000 description 2
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- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- HXBDLCVKRPJJAO-UHFFFAOYSA-N C=CC1=CC=CC=C1.C(CC(C)C)C=C Chemical compound C=CC1=CC=CC=C1.C(CC(C)C)C=C HXBDLCVKRPJJAO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
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- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
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- 150000001413 amino acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 description 1
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Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
膜 | 离子交换容量mmol/g | 电流效率% | 电压效率% | 能量效率% |
实施例1 | 0.88 | 98.2 | 81.9 | 80.5 |
实施例2 | 1.14 | 98.9 | 86.7 | 85.7 |
实施例3 | 1.46 | 97.8 | 88.5 | 86.6 |
Nafion117 | - | 95.7 | 89.6 | 85.7 |
Claims (10)
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CN 201010141349 CN101837253B (zh) | 2010-04-01 | 2010-04-01 | 含二氮杂萘酮结构聚芳醚酮酮阴离子交换膜及其制备方法 |
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CN 201010141349 CN101837253B (zh) | 2010-04-01 | 2010-04-01 | 含二氮杂萘酮结构聚芳醚酮酮阴离子交换膜及其制备方法 |
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CN101837253A true CN101837253A (zh) | 2010-09-22 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103159971A (zh) * | 2011-12-19 | 2013-06-19 | 中国科学院大连化学物理研究所 | 一种阴离子交换膜的制备方法 |
CN103372381A (zh) * | 2012-04-19 | 2013-10-30 | 中国科学技术大学 | 一种阴离子交换膜及其制备方法和燃料电池 |
CN105906812A (zh) * | 2016-05-16 | 2016-08-31 | 大连理工大学 | 一种新型嵌段阴离子交换膜及其制备方法 |
CN106633033A (zh) * | 2016-11-30 | 2017-05-10 | 大连理工大学 | 含二氮杂萘酮联苯结构自具微孔共聚物及其制备方法 |
CN107903416A (zh) * | 2017-10-26 | 2018-04-13 | 大连理工大学 | 含二氮杂萘酮结构聚芳醚酮两性离子交换膜及其制备方法 |
CN108348864A (zh) * | 2015-11-05 | 2018-07-31 | 莫纳什大学 | 不对称多孔离子交换膜及其制造方法 |
CN109438695A (zh) * | 2018-10-09 | 2019-03-08 | 大连理工大学 | 一种含杂萘联苯结构的全氟环丁基共聚芳醚的合成方法 |
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CN1564341A (zh) * | 2004-03-31 | 2005-01-12 | 大连理工大学 | 磺化二氮杂萘聚醚砜酮质子交换膜及其制备方法 |
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2010
- 2010-04-01 CN CN 201010141349 patent/CN101837253B/zh active Active
Patent Citations (1)
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CN1564341A (zh) * | 2004-03-31 | 2005-01-12 | 大连理工大学 | 磺化二氮杂萘聚醚砜酮质子交换膜及其制备方法 |
Non-Patent Citations (1)
Title |
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《高分子学报》 19990131 刘彦军 含二氮杂萘酮结构聚醚酮酮的合成及表征 37-39 1-10 , 第1期 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103159971A (zh) * | 2011-12-19 | 2013-06-19 | 中国科学院大连化学物理研究所 | 一种阴离子交换膜的制备方法 |
CN103372381A (zh) * | 2012-04-19 | 2013-10-30 | 中国科学技术大学 | 一种阴离子交换膜及其制备方法和燃料电池 |
CN103372381B (zh) * | 2012-04-19 | 2015-04-08 | 中国科学技术大学 | 一种阴离子交换膜及其制备方法和燃料电池 |
CN108348864A (zh) * | 2015-11-05 | 2018-07-31 | 莫纳什大学 | 不对称多孔离子交换膜及其制造方法 |
CN105906812A (zh) * | 2016-05-16 | 2016-08-31 | 大连理工大学 | 一种新型嵌段阴离子交换膜及其制备方法 |
CN105906812B (zh) * | 2016-05-16 | 2018-12-18 | 大连理工大学 | 一种嵌段阴离子交换膜及其制备方法 |
CN106633033A (zh) * | 2016-11-30 | 2017-05-10 | 大连理工大学 | 含二氮杂萘酮联苯结构自具微孔共聚物及其制备方法 |
CN106633033B (zh) * | 2016-11-30 | 2018-10-16 | 大连理工大学 | 含二氮杂萘酮联苯结构自具微孔共聚物及其制备方法 |
CN107903416A (zh) * | 2017-10-26 | 2018-04-13 | 大连理工大学 | 含二氮杂萘酮结构聚芳醚酮两性离子交换膜及其制备方法 |
CN107903416B (zh) * | 2017-10-26 | 2021-01-19 | 大连理工大学 | 含二氮杂萘酮结构聚芳醚酮两性离子交换膜及其制备方法 |
CN109438695A (zh) * | 2018-10-09 | 2019-03-08 | 大连理工大学 | 一种含杂萘联苯结构的全氟环丁基共聚芳醚的合成方法 |
CN109438695B (zh) * | 2018-10-09 | 2021-05-11 | 大连理工大学 | 一种含杂萘联苯结构的全氟环丁基共聚芳醚的合成方法 |
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