JP2019518809A5 - - Google Patents
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- JP2019518809A5 JP2019518809A5 JP2018550323A JP2018550323A JP2019518809A5 JP 2019518809 A5 JP2019518809 A5 JP 2019518809A5 JP 2018550323 A JP2018550323 A JP 2018550323A JP 2018550323 A JP2018550323 A JP 2018550323A JP 2019518809 A5 JP2019518809 A5 JP 2019518809A5
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- Prior art keywords
- polymer
- monomer
- membrane
- hydroxide
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- Prior art date
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- 229920000642 polymer Polymers 0.000 claims 51
- 239000000178 monomer Substances 0.000 claims 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 14
- 239000012528 membrane Substances 0.000 claims 12
- 238000006116 polymerization reaction Methods 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000000758 substrate Substances 0.000 claims 10
- 239000000446 fuel Substances 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 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 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 238000005349 anion exchange Methods 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 8
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 6
- 150000002222 fluorine compounds Chemical group 0.000 claims 6
- 239000002685 polymerization catalyst Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- PQVNJXLMQLJOLF-UHFFFAOYSA-N O=C1CC[N+]2(CC1)CCCCC2 Chemical class O=C1CC[N+]2(CC1)CCCCC2 PQVNJXLMQLJOLF-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000007795 chemical reaction product Substances 0.000 claims 5
- 229940087189 2,2,2-trifluoroacetophenone Drugs 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 238000010612 desalination reaction Methods 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- -1 hydroxide ions Chemical class 0.000 claims 4
- 229920005597 polymer membrane Polymers 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000003011 anion exchange membrane Substances 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 239000003792 electrolyte Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 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 3
- 150000002500 ions Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 238000004065 wastewater treatment Methods 0.000 claims 3
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229920000554 ionomer Polymers 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 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 1
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- 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 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 238000005266 casting Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical group 0.000 claims 1
- 238000005470 impregnation Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims 1
- 239000004810 polytetrafluoroethylene Substances 0.000 claims 1
- 0 *c1c(*)c(*)c(C(C(F)(F)F)=O)c(*)c1* Chemical compound *c1c(*)c(*)c(C(C(F)(F)F)=O)c(*)c1* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662314008P | 2016-03-28 | 2016-03-28 | |
| US62/314,008 | 2016-03-28 | ||
| PCT/US2017/024615 WO2017172824A1 (en) | 2016-03-28 | 2017-03-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019518809A JP2019518809A (ja) | 2019-07-04 |
| JP2019518809A5 true JP2019518809A5 (enExample) | 2020-05-07 |
| JP7153561B2 JP7153561B2 (ja) | 2022-10-14 |
Family
ID=59966424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018550323A Active JP7153561B2 (ja) | 2016-03-28 | 2017-03-28 | ヒドロキシド交換膜およびヒドロキシド交換アイオノマーとしての使用のためのポリ（アリールピペリジニウム）ポリマー |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10290890B2 (enExample) |
| EP (1) | EP3436186B1 (enExample) |
| JP (1) | JP7153561B2 (enExample) |
| KR (1) | KR102380604B1 (enExample) |
| CN (1) | CN109070022B (enExample) |
| CA (1) | CA3019209A1 (enExample) |
| ES (1) | ES3040844T3 (enExample) |
| IL (1) | IL262015B (enExample) |
| WO (1) | WO2017172824A1 (enExample) |
Families Citing this family (84)
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| WO2019068051A2 (en) * | 2017-09-28 | 2019-04-04 | Yushan Yan | POLY (ARYL PIPERIDINIUM) POLYMERS COMPRISING THOSE HAVING STATIC CATIONIC PENDANT GROUPS FOR USE AS ANION AND IONOMER EXCHANGING MEMBRANES |
| 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 |
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| US10811711B2 (en) | 2018-11-20 | 2020-10-20 | University Of Delaware | Electrochemical devices and fuel cell systems |
| CN113366680B (zh) * | 2018-11-26 | 2024-06-07 | 伦斯勒理工学院 | 磷酸根阴离子-季铵离子对配位的聚合物膜 |
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| CN116041766A (zh) * | 2022-11-02 | 2023-05-02 | 宿迁时代储能科技有限公司 | 一种含氟的交联型阴离子交换膜及其制备方法和应用 |
| EP4365216A1 (en) | 2022-11-04 | 2024-05-08 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Fluorinated polyaromatics with linear, branched or crosslinked structure for anion exchange membranes and ionomers |
| CN115612069A (zh) * | 2022-11-08 | 2023-01-17 | 惠州亿纬燃料电池有限公司 | 一种芳基哌啶叔胺基聚合物及其制备方法和应用 |
| CN115678073B (zh) * | 2022-11-15 | 2024-03-12 | 上海交通大学 | 一种支化聚(芳基哌啶鎓)阴离子交换膜及其制备方法和应用 |
| US12378685B2 (en) | 2022-12-22 | 2025-08-05 | Twelve Benefit Corporation | Surface modification of metal catalysts with hydrophobic ligands or ionomers |
| KR20240110307A (ko) * | 2023-01-06 | 2024-07-15 | 현대자동차주식회사 | 음이온 교환막을 포함하는 금속-이산화탄소 전지 |
| DE102023102255A1 (de) * | 2023-01-31 | 2024-08-01 | Forschungszentrum Jülich GmbH | Verfahren zur Herstellung eines Polymers, insbesondere für eine Membran, Polymer, Membran und Verwendung einer Membran |
| KR20260005917A (ko) | 2023-04-19 | 2026-01-12 | 사이언스코 스페셜티 폴리머즈 유에스에이, 엘엘씨 | 연료 전지 또는 전해 전지 응용을 위한 폴리페닐렌 이오노머 |
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| WO2025070387A1 (ja) * | 2023-09-25 | 2025-04-03 | 富士フイルム株式会社 | ヒドロキシイオン伝導膜、ヒドロキシイオン伝導膜の製造方法、膜電極接合体、水素製造方法、及び水素製造システム |
| CN117362561B (zh) * | 2023-11-06 | 2024-03-29 | 合肥工业大学 | 一种高耐碱性阳离子聚合物及其制备方法和应用 |
| CN117802532B (zh) * | 2023-12-25 | 2024-08-16 | 碳谐科技(上海)有限公司 | 复合隔膜及其制备方法和应用 |
| CN118063742B (zh) * | 2024-02-20 | 2025-04-22 | 佛山大学 | 一种含长碳氟链阴离子交换膜及制备方法 |
| CN118546339A (zh) * | 2024-05-15 | 2024-08-27 | 广东鸣洋科技有限公司 | 一种含碳氟主链的聚芳基哌啶电解质材料及其应用 |
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| US3480626A (en) * | 1967-05-18 | 1969-11-25 | Chem Fab Dr R Pfleger | Certain azoniaspironortropine derivatives |
| US5268470A (en) * | 1991-07-12 | 1993-12-07 | Buckman Laboratories Internation, Inc. | Diamine compounds, method of making same, method of use of same and intermediates |
| JPH0691949B2 (ja) * | 1992-04-23 | 1994-11-16 | 通商産業省基礎産業局長 | ポリイオンコンプレックス製分離膜 |
| US5547551A (en) | 1995-03-15 | 1996-08-20 | W. L. Gore & Associates, Inc. | Ultra-thin integral composite membrane |
| USRE37701E1 (en) | 1994-11-14 | 2002-05-14 | W. L. Gore & Associates, Inc. | Integral composite membrane |
| WO2010055889A1 (ja) | 2008-11-14 | 2010-05-20 | 株式会社トクヤマ | 陰イオン交換膜及びその製造方法 |
| WO2010081851A1 (en) * | 2009-01-14 | 2010-07-22 | Genoscience Pharma | Piperidin-4-ylpiperazine compounds for the treatment of hcv infection |
| JP5779016B2 (ja) | 2010-07-30 | 2015-09-16 | 株式会社豊田中央研究所 | 電解質、並びに、燃料電池、Ｌｉ二次電池、二次電池及び一次電池 |
| JP5386450B2 (ja) | 2010-07-30 | 2014-01-15 | 株式会社豊田中央研究所 | 電解質 |
| CN102255089A (zh) * | 2011-04-25 | 2011-11-23 | 大连理工大学 | 杂环聚合物碱性阴离子交换膜及其制备方法 |
| CN102797043B (zh) * | 2011-05-23 | 2015-11-25 | 天利康（天津）科技有限公司 | 药物分子片段库及其构建方法 |
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| EP3239193A1 (de) * | 2016-04-27 | 2017-11-01 | Leibniz-Institut für Polymerforschung Dresden e.V. | Wasserunlösliche anionenaustauschermaterialien |
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- 2017-03-28 WO PCT/US2017/024615 patent/WO2017172824A1/en not_active Ceased
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- 2017-03-28 CN CN201780021383.2A patent/CN109070022B/zh active Active
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