JP2007507560A5 - - Google Patents
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- Publication number
- JP2007507560A5 JP2007507560A5 JP2006527966A JP2006527966A JP2007507560A5 JP 2007507560 A5 JP2007507560 A5 JP 2007507560A5 JP 2006527966 A JP2006527966 A JP 2006527966A JP 2006527966 A JP2006527966 A JP 2006527966A JP 2007507560 A5 JP2007507560 A5 JP 2007507560A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- polymer
- grafting
- fluorinated
- membrane
- 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.)
- Pending
Links
- 239000012528 membrane Substances 0.000 claims description 60
- 229920005601 base polymer Polymers 0.000 claims description 36
- 239000000178 monomer Substances 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000446 fuel Substances 0.000 claims description 15
- 239000005518 polymer electrolyte Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- 150000003949 imides Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- USPTVMVRNZEXCP-UHFFFAOYSA-N sulfamoyl fluoride Chemical compound NS(F)(=O)=O USPTVMVRNZEXCP-UHFFFAOYSA-N 0.000 claims description 12
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000839 emulsion Substances 0.000 claims description 4
- 229920002313 fluoropolymer Polymers 0.000 claims description 4
- 230000005865 ionizing radiation Effects 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 perfluoromethoxy Chemical group 0.000 description 48
- 238000000034 method Methods 0.000 description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 12
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- 229920005569 poly(vinylidene fluoride-co-hexafluoropropylene) Polymers 0.000 description 9
- 239000004810 polytetrafluoroethylene Substances 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 5
- 239000008199 coating composition Substances 0.000 description 5
- DCSIADKYJYMWMM-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;1,1,2,2-tetrafluoroethene Chemical compound FC(F)=C(F)F.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 DCSIADKYJYMWMM-UHFFFAOYSA-N 0.000 description 4
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003014 ion exchange membrane Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000010411 electrocatalyst Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002620 polyvinyl fluoride Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50703503P | 2003-09-29 | 2003-09-29 | |
| PCT/US2004/020704 WO2005049204A2 (en) | 2003-09-29 | 2004-06-25 | Trifluorostyrene containing compounds grafted to base polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007507560A JP2007507560A (ja) | 2007-03-29 |
| JP2007507560A5 true JP2007507560A5 (enExample) | 2007-08-02 |
Family
ID=34619304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006527966A Pending JP2007507560A (ja) | 2003-09-29 | 2004-06-25 | ベースポリマーにグラフト化されたトリフルオロスチレン含有化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7563532B2 (enExample) |
| JP (1) | JP2007507560A (enExample) |
| DE (1) | DE112004001818T5 (enExample) |
| TW (1) | TW200512220A (enExample) |
| WO (1) | WO2005049204A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200536868A (en) * | 2004-05-07 | 2005-11-16 | Du Pont | Stable trifluorostyrene containing compounds, and their use in polymer electrolyte membranes |
| DE112004002850T5 (de) | 2004-05-07 | 2007-04-05 | E.I. Du Pont De Nemours And Company, Wilmington | Beständige Trifluorstyrol enthaltende Verbindungen, die auf Basispolymere aufgepfropft sind, und ihre Verwendung als Polymerelektrolytmembranen |
| US7737190B2 (en) | 2005-03-24 | 2010-06-15 | E.I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers using a solvent/water mixture |
| WO2006102672A1 (en) * | 2005-03-24 | 2006-09-28 | E. I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers using an alcohol/water mixture |
| WO2006102670A1 (en) * | 2005-03-24 | 2006-09-28 | E. I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers |
| JP2006351244A (ja) * | 2005-06-13 | 2006-12-28 | Shin Etsu Chem Co Ltd | 固体高分子電解質膜及びその製造方法、並びに燃料電池 |
| US9090723B2 (en) * | 2009-12-15 | 2015-07-28 | Shandong Huaxia Shenzou New Material Co., Ltd. | High exchange capacity perfluorinated ion exchange resin, preparation method and use thereof |
| SG11201807983PA (en) * | 2016-03-18 | 2018-10-30 | Entegris Inc | Hydrophobic polyethylene membrane for use in venting, degassing, and membrane distillation processes |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4169023A (en) * | 1974-02-04 | 1979-09-25 | Tokuyama Soda Kabushiki Kaisha | Electrolytic diaphragms, and method of electrolysis using the same |
| US4113922A (en) * | 1974-12-23 | 1978-09-12 | Hooker Chemicals & Plastics Corp. | Trifluorostyrene sulfonic acid membranes |
| JPS5785826A (en) * | 1980-11-17 | 1982-05-28 | Japan Atom Energy Res Inst | Cation exchange membrane |
| JPS57131376A (en) * | 1981-02-06 | 1982-08-14 | Japan Atom Energy Res Inst | Electrolyzing method for water |
| AU551369B2 (en) * | 1981-08-07 | 1986-04-24 | Ici Australia Limited | Polymerization process |
| US5602185A (en) * | 1993-09-21 | 1997-02-11 | Ballard Power Systems Inc. | Substituted trifluorostyrene compositions |
| US5834523A (en) * | 1993-09-21 | 1998-11-10 | Ballard Power Systems, Inc. | Substituted α,β,β-trifluorostyrene-based composite membranes |
| US5536754A (en) * | 1995-02-15 | 1996-07-16 | E. I. Du Pont De Nemours And Company | Fluorinated ion-exchange polymers and intermediates therefor |
| JP3810179B2 (ja) * | 1996-05-10 | 2006-08-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 向上した電気化学的特性を有するカチオン交換膜の製造方法 |
| US6723758B2 (en) | 1997-11-12 | 2004-04-20 | Ballard Power Systems Inc. | Graft polymeric membranes and ion-exchange membranes formed therefrom |
| US6359019B1 (en) * | 1997-11-12 | 2002-03-19 | Ballard Power Systems Inc. | Graft polymeric membranes and ion-exchange membranes formed therefrom |
| DE19817376A1 (de) * | 1998-04-18 | 1999-10-21 | Univ Stuttgart Lehrstuhl Und I | Säure-Base-Polymerblends und ihre Verwendung in Membranprozessen |
| JP2003522224A (ja) * | 2000-02-14 | 2003-07-22 | バラード パワー システムズ インコーポレイティド | グラフトポリマー膜およびグラフトポリマー膜から形成されるイオン交換膜 |
| US6777515B2 (en) * | 2001-07-13 | 2004-08-17 | I. Du Pont De Nemours And Company | Functional fluorine-containing polymers and ionomers derived therefrom |
| ATE356839T1 (de) * | 2001-08-27 | 2007-04-15 | Ballard Power Systems | Verfahren zur herstellung von pfropf-copolymer membranen |
| US6828386B2 (en) * | 2002-09-20 | 2004-12-07 | Ballard Power Systems Inc. | Process for preparing graft copolymers and membranes formed therefrom |
| KR100493171B1 (ko) * | 2003-02-08 | 2005-06-02 | 삼성에스디아이 주식회사 | 복합전해질막 및 이를 채용한 연료전지 |
| JP2007528907A (ja) | 2003-06-27 | 2007-10-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | トリフルオロスチレン含有化合物、およびポリマー電解質膜におけるそれらの使用 |
| DE112004002850T5 (de) | 2004-05-07 | 2007-04-05 | E.I. Du Pont De Nemours And Company, Wilmington | Beständige Trifluorstyrol enthaltende Verbindungen, die auf Basispolymere aufgepfropft sind, und ihre Verwendung als Polymerelektrolytmembranen |
| TW200536868A (en) | 2004-05-07 | 2005-11-16 | Du Pont | Stable trifluorostyrene containing compounds, and their use in polymer electrolyte membranes |
| WO2006102670A1 (en) | 2005-03-24 | 2006-09-28 | E. I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers |
| WO2006102672A1 (en) | 2005-03-24 | 2006-09-28 | E. I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers using an alcohol/water mixture |
| US7737190B2 (en) | 2005-03-24 | 2010-06-15 | E.I. Du Pont De Nemours And Company | Process to prepare stable trifluorostyrene containing compounds grafted to base polymers using a solvent/water mixture |
-
2004
- 2004-06-25 US US10/570,024 patent/US7563532B2/en not_active Expired - Fee Related
- 2004-06-25 WO PCT/US2004/020704 patent/WO2005049204A2/en not_active Ceased
- 2004-06-25 DE DE112004001818T patent/DE112004001818T5/de not_active Withdrawn
- 2004-06-25 JP JP2006527966A patent/JP2007507560A/ja active Pending
- 2004-06-25 TW TW093118621A patent/TW200512220A/zh unknown
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