KR102380604B1 - 수산화물 교환막 및 이오노머로서 사용하기 위한 폴리(아릴 피페리디늄) 폴리머 - Google Patents
수산화물 교환막 및 이오노머로서 사용하기 위한 폴리(아릴 피페리디늄) 폴리머 Download PDFInfo
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- KR102380604B1 KR102380604B1 KR1020187028658A KR20187028658A KR102380604B1 KR 102380604 B1 KR102380604 B1 KR 102380604B1 KR 1020187028658 A KR1020187028658 A KR 1020187028658A KR 20187028658 A KR20187028658 A KR 20187028658A KR 102380604 B1 KR102380604 B1 KR 102380604B1
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- fluoride
- monomer
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- 229920000642 polymer Polymers 0.000 title claims abstract description 194
- 239000012528 membrane Substances 0.000 title claims abstract description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 title claims abstract description 76
- -1 Poly(aryl piperidinium Chemical compound 0.000 title claims abstract description 60
- 229920000554 ionomer Polymers 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000000446 fuel Substances 0.000 claims abstract description 54
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 238000010521 absorption reaction Methods 0.000 claims abstract description 15
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- 125000000217 alkyl group Chemical group 0.000 claims description 44
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 39
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 claims description 36
- 150000002222 fluorine compounds Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 29
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- 238000000034 method Methods 0.000 claims description 22
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- 238000006243 chemical reaction Methods 0.000 claims description 19
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 claims description 14
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- 238000005349 anion exchange Methods 0.000 claims description 12
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- IIENZDKFAYEFGJ-UHFFFAOYSA-M [I-].O=C1CC[N+]2(CC1)CCCCC2 Chemical compound [I-].O=C1CC[N+]2(CC1)CCCCC2 IIENZDKFAYEFGJ-UHFFFAOYSA-M 0.000 claims description 10
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- 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 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 239000001301 oxygen Substances 0.000 claims description 7
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 3
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- NJQFCQXFOHVYQJ-PMACEKPBSA-N BF 4 Chemical compound C1([C@@H]2CC(=O)C=3C(O)=C(C)C4=C(C=3O2)[C@H](C(C)C)C2=C(O4)C(C)=C(C(C2=O)(C)C)OC)=CC=CC=C1 NJQFCQXFOHVYQJ-PMACEKPBSA-N 0.000 claims description 2
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- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
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- 150000002576 ketones Chemical class 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 34
- 239000000126 substance Substances 0.000 abstract description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 abstract description 3
- 150000001768 cations Chemical class 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 37
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- 238000003786 synthesis reaction Methods 0.000 description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
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| US11236196B2 (en) | 2014-11-18 | 2022-02-01 | Rensselaer Polytechnic Institute | Polymers and methods for their manufacture |
| CN111647138B (zh) | 2014-11-18 | 2023-09-12 | 伦斯勒理工学院 | 新型聚合物 |
| US12359325B2 (en) | 2016-05-03 | 2025-07-15 | Twelve Benefit Corporation | Membrane electrode assembly for COx reduction |
| HUE056900T2 (hu) | 2016-05-03 | 2022-04-28 | Opus 12 Incorporated | Korszerû architektúrájú reaktor CO2, CO és más kémiai vegyületek elektrokémiai reakciójához |
| WO2018119020A1 (en) | 2016-12-20 | 2018-06-28 | Rensselaer Polytechnic Institute | Proton exchange membrane material and methods of making the same |
| US20200238272A1 (en) | 2017-07-06 | 2020-07-30 | Rensselaer Polytechnic Institute | Ionic functionalization of aromatic polymers for ion exchange membranes |
| IL273687B2 (en) * | 2017-09-28 | 2024-11-01 | Yushan Yan | Poly(aryl piperidinium) polymers including those with stable cationic pendant groups for use as anion exchange membranes and ionomers |
| CN107910576A (zh) * | 2017-11-03 | 2018-04-13 | 武汉大学 | 一类高化学稳定性的阴离子聚合物膜的制备方法 |
| US12320022B2 (en) | 2018-01-22 | 2025-06-03 | Twelve Benefit Corporation | System and method for carbon dioxide reactor control |
| CN108383993B (zh) * | 2018-02-13 | 2019-06-11 | 浙江大学 | 含asu侧链的聚合物及其制备方法和基于该聚合物的阴离子交换膜 |
| WO2019209959A1 (en) | 2018-04-24 | 2019-10-31 | Rensselaer Polytechnic Institute | Crosslinking of aromatic polymers for anion exchange membranes |
| US10811711B2 (en) * | 2018-11-20 | 2020-10-20 | University Of Delaware | Electrochemical devices and fuel cell systems |
| EP3888172A4 (en) * | 2018-11-26 | 2022-08-24 | Rensselaer Polytechnic Institute | QUATERNARY PHOSPHATE-AMMONIUM ANION COORDINATED POLYMERIC MEMBRANES |
| US12145099B2 (en) * | 2019-01-25 | 2024-11-19 | Eurica Californiaa | Membrane-based processing for ambient water-group species captured on the moon and in space |
| US11969722B2 (en) * | 2019-06-26 | 2024-04-30 | Ffi Ionix Ip, Inc. | Anionic membranes incorporating functional additives |
| AU2020244873A1 (en) | 2019-03-28 | 2021-10-21 | University Of Delaware | Polymers having stable cationic pendant groups for use as anion exchange membranes |
| HUE062445T2 (hu) * | 2019-07-22 | 2023-11-28 | Evonik Operations Gmbh | Anionvezetõ polimer membrán |
| CN110661021B (zh) * | 2019-09-17 | 2021-02-05 | 北京航空航天大学 | 一种燃料电池用高温质子交换膜的制备方法 |
| EP4065753A1 (en) | 2019-11-25 | 2022-10-05 | Twelve Benefit Corporation | Membrane electrode assembly for co x reduction |
| KR20210071810A (ko) | 2019-12-06 | 2021-06-16 | 한양대학교 산학협력단 | 신규 폴리플루오렌계 중합체 이오노머, 음이온교환막 및 이의 제조방법 |
| CN111040137B (zh) * | 2019-12-27 | 2022-09-13 | 惠州市亿纬新能源研究院 | 一种阴离子交换聚合物及其制备方法和应用 |
| AU2021211728A1 (en) | 2020-01-22 | 2022-08-04 | Rensselaer Polytechnic Institute | Anion-solvating polymer membranes |
| US11465139B2 (en) | 2020-03-20 | 2022-10-11 | Rensselaer Polytechnic Institute | Thermally stable hydrocarbon-based anion exchange membrane and ionomers |
| CA3177207A1 (en) * | 2020-05-04 | 2021-11-11 | University Of Delaware | An anion exchange membrane electrolyzer having a platinum-group-metal free self-supported oxygen evolution electrode |
| CN111530308B (zh) * | 2020-05-12 | 2022-05-10 | 福建师范大学 | 侧基含卟啉催化基团的单片型聚芳醚酮双极膜制备方法 |
| CN112552488A (zh) * | 2020-05-28 | 2021-03-26 | 合肥工业大学 | 一种含耐碱解阳离子基团和氟碳侧链的离聚物及其制备方法和应用 |
| CN112175217B (zh) * | 2020-09-01 | 2022-02-11 | 中国科学院山西煤炭化学研究所 | 一种含亚芳基哌啶与二酮类单体共聚物的阴离子交换膜及其制备方法和应用 |
| KR20230092977A (ko) * | 2020-10-20 | 2023-06-26 | 트웰브 베네핏 코포레이션 | 이온성 중합체 및 공중합체 |
| AU2021365135A1 (en) * | 2020-10-20 | 2023-06-22 | Twelve Benefit Corporation | Semi-interpenetrating and crosslinked polymers and membranes thereof |
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