JP2018528316A5 - - Google Patents
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- Publication number
- JP2018528316A5 JP2018528316A5 JP2018515220A JP2018515220A JP2018528316A5 JP 2018528316 A5 JP2018528316 A5 JP 2018528316A5 JP 2018515220 A JP2018515220 A JP 2018515220A JP 2018515220 A JP2018515220 A JP 2018515220A JP 2018528316 A5 JP2018528316 A5 JP 2018528316A5
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- vinyl ether
- cation
- independently
- nzh
- 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.)
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- 238000000034 method Methods 0.000 claims 13
- 229920001577 copolymer Polymers 0.000 claims 9
- -1 alkali metal cation Chemical class 0.000 claims 7
- 238000007334 copolymerization reaction Methods 0.000 claims 4
- 239000012528 membrane Substances 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000005518 polymer electrolyte Substances 0.000 claims 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims 1
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 claims 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims 1
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 claims 1
- WFJINAXLTGKWLB-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC=C WFJINAXLTGKWLB-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- OJPSFJLSZZTSDF-UHFFFAOYSA-N 3-ethoxyprop-1-ene Chemical compound CCOCC=C OJPSFJLSZZTSDF-UHFFFAOYSA-N 0.000 claims 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical class OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 230000015271 coagulation Effects 0.000 claims 1
- 238000005345 coagulation Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 238000010556 emulsion polymerization method Methods 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- CDXZRBLOGJXGTN-UHFFFAOYSA-N prop-2-enoxycyclohexane Chemical compound C=CCOC1CCCCC1 CDXZRBLOGJXGTN-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562222296P | 2015-09-23 | 2015-09-23 | |
| US62/222,296 | 2015-09-23 | ||
| PCT/US2016/053104 WO2017053563A1 (en) | 2015-09-23 | 2016-09-22 | Method of making a copolymer of tetrafluoroethylene having sulfonyl pendant groups |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018528316A JP2018528316A (ja) | 2018-09-27 |
| JP2018528316A5 true JP2018528316A5 (enExample) | 2019-10-31 |
| JP6941604B2 JP6941604B2 (ja) | 2021-09-29 |
Family
ID=58387310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018515220A Active JP6941604B2 (ja) | 2015-09-23 | 2016-09-22 | スルホニルペンダント基を有するテトラフルオロエチレンのコポリマーを作製する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11155661B2 (enExample) |
| EP (1) | EP3353221B1 (enExample) |
| JP (1) | JP6941604B2 (enExample) |
| CN (1) | CN108137750A (enExample) |
| WO (1) | WO2017053563A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190027769A1 (en) * | 2016-03-07 | 2019-01-24 | 3M Innovative Properties Company | Fluorinated copolymer having sulfonyl pendant groups and method of making an ionomer |
| US11492431B2 (en) * | 2017-09-14 | 2022-11-08 | 3M Innovative Properties Company | Fluorinated copolymer having sulfonyl pendant groups and compositions and articles including the same |
| CN108084063A (zh) * | 2017-11-25 | 2018-05-29 | 山东华夏神舟新材料有限公司 | 全氟乙烯基醚磺酸盐的制备方法 |
| US20190169338A1 (en) * | 2017-12-01 | 2019-06-06 | Honeywell International Inc. | Fluoropolymers for coating applications |
| WO2019176425A1 (ja) * | 2018-03-14 | 2019-09-19 | 旭化成株式会社 | スルホン酸基含有モノマーの製造方法 |
| FR3079834B1 (fr) * | 2018-04-10 | 2021-09-10 | Arkema Inc | Fluoropolymeres fonctionnels |
| WO2020094563A1 (en) * | 2018-11-05 | 2020-05-14 | Solvay Specialty Polymers Italy S.P.A. | Dispersible ionomer powder and method of making the same |
| KR102784849B1 (ko) * | 2018-12-07 | 2025-03-20 | 에이지씨 가부시키가이샤 | 액상 조성물, 고체 고분자 전해질막, 막 전극 접합체, 고체 고분자형 연료 전지 |
| JP7734684B2 (ja) | 2020-03-30 | 2025-09-05 | スリーエム イノベイティブ プロパティズ カンパニー | イオン性ビス（スルホニル）イミド部分及びペルフルオロエーテル末端基を有するペンダント基を含むフルオロポリマー |
| US20230090482A1 (en) * | 2020-04-09 | 2023-03-23 | 3M Innovative Properties Company | Composite including fluorinated polymer and salt nanoparticles and articles including the same |
| CA3203858A1 (en) * | 2020-12-31 | 2022-07-07 | Rajesh Bashyam | Fuel cell catalyst coated membrane and method of manufacture |
| US12341227B2 (en) | 2021-06-04 | 2025-06-24 | 3M Innovative Properties Company | Perfluorosulfonyl monomers suitable for fluoropolymers and fuel cell membrane articles |
| CA3231950A1 (en) * | 2021-09-17 | 2023-03-23 | Sukanta Bhattacharyya | Metal fluoride-functionalized proton exchange solid supports, membranes, and ionomers |
| CN116265492B (zh) * | 2021-12-17 | 2024-05-14 | 济南大学 | 一类氢键增强型全氟共轭阳离子树脂及其合成方法以及阴离子交换膜和膜电极 |
| JP2025522322A (ja) * | 2022-06-03 | 2025-07-15 | セラダイン テクノロジーズ，インコーポレイテッド | 複合高分子電解質セラミック膜 |
| CN115109177B (zh) * | 2022-06-09 | 2023-06-20 | 东风汽车集团股份有限公司 | 一种mea耐久增强剂及其制备方法和应用 |
| CN115582136A (zh) * | 2022-10-14 | 2023-01-10 | 国能龙源环保有限公司 | 一种用于脱硫脱硝的亚砜类催化剂及其制备方法 |
| CN116217780A (zh) * | 2022-12-22 | 2023-06-06 | 福建科润世纪氢能材料有限公司 | 一种全氟聚合物制备方法及其在离子交换膜中的应用 |
| WO2025233234A1 (en) * | 2024-05-06 | 2025-11-13 | Syensqo Specialty Polymers Italy S.p.A. | Monomer composition and use thereof for the preparation of a fluorinated polymer |
| CN119786670A (zh) * | 2024-12-30 | 2025-04-08 | 天津大学浙江研究院 | 一种共价有机框架质子交换膜及其制备方法和高温质子交换膜燃料电池 |
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| US7265162B2 (en) | 2003-11-13 | 2007-09-04 | 3M Innovative Properties Company | Bromine, chlorine or iodine functional polymer electrolytes crosslinked by e-beam |
| EP1561729A1 (en) | 2004-02-05 | 2005-08-10 | 3M Innovative Properties Company | Removal of fluorinated surfactants from waste water |
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| GB0514387D0 (en) | 2005-07-15 | 2005-08-17 | 3M Innovative Properties Co | Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant |
| US8367267B2 (en) | 2005-10-28 | 2013-02-05 | 3M Innovative Properties Company | High durability fuel cell components with cerium oxide additives |
| US8628871B2 (en) | 2005-10-28 | 2014-01-14 | 3M Innovative Properties Company | High durability fuel cell components with cerium salt additives |
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| GB0714361D0 (en) * | 2007-07-24 | 2007-09-05 | 3M Innovative Properties Co | Cation conductive membranes comprising polysulfonic acid polymers and metal salts having an F-containing anion |
| GB0801194D0 (en) | 2008-01-23 | 2008-02-27 | 3M Innovative Properties Co | Processing aid compositions comprising fluoropolymers having long-chain branches |
| JP5217708B2 (ja) | 2008-07-09 | 2013-06-19 | 旭硝子株式会社 | ポリマー、その製造方法、固体高分子形燃料電池用電解質膜および膜電極接合体 |
| JP5540681B2 (ja) | 2009-07-14 | 2014-07-02 | 株式会社豊田中央研究所 | 改質電解質及びその製造方法、並びに、改質剤 |
| JP5682153B2 (ja) | 2010-02-01 | 2015-03-11 | ダイキン工業株式会社 | 含フッ素共重合体の製造方法、ポリマー電解質、リチウム電池用電極及びリチウム電池 |
| US9711816B2 (en) * | 2011-08-04 | 2017-07-18 | 3M Innovative Properties Company | Low equivalent weight polymers |
| JP5862372B2 (ja) | 2012-03-02 | 2016-02-16 | 旭硝子株式会社 | ポリマーの製造方法、固体高分子形燃料電池用電解質膜の製造方法および膜電極接合体の製造方法 |
| WO2015173193A1 (en) * | 2014-05-12 | 2015-11-19 | Solvay Specialty Polymers Italy S.P.A. | Method for the controlled polymerization of fluoromonomers |
| WO2016130894A1 (en) * | 2015-02-12 | 2016-08-18 | 3M Innovative Properties Company | Tetrafluoroethylene copolymers having sulfonyl groups |
| US20190027769A1 (en) | 2016-03-07 | 2019-01-24 | 3M Innovative Properties Company | Fluorinated copolymer having sulfonyl pendant groups and method of making an ionomer |
-
2016
- 2016-09-22 EP EP16849591.9A patent/EP3353221B1/en active Active
- 2016-09-22 JP JP2018515220A patent/JP6941604B2/ja active Active
- 2016-09-22 CN CN201680055739.XA patent/CN108137750A/zh active Pending
- 2016-09-22 WO PCT/US2016/053104 patent/WO2017053563A1/en not_active Ceased
- 2016-09-22 US US15/762,267 patent/US11155661B2/en active Active
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