JP2009094070A - 有機溶媒乾燥法による均一に硫酸基が付着されたpeek電解質膜の製造方法 - Google Patents
有機溶媒乾燥法による均一に硫酸基が付着されたpeek電解質膜の製造方法 Download PDFInfo
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- 239000012528 membrane Substances 0.000 title claims abstract description 78
- 239000003792 electrolyte Substances 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims abstract description 18
- 239000003960 organic solvent Substances 0.000 title claims abstract description 17
- 238000001035 drying Methods 0.000 title claims description 7
- 239000004696 Poly ether ether ketone Substances 0.000 claims abstract description 33
- 229920002530 polyetherether ketone Polymers 0.000 claims abstract description 33
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 230000001376 precipitating effect Effects 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000007865 diluting Methods 0.000 claims abstract description 4
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 claims abstract 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
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- 238000010298 pulverizing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 105
- 239000000446 fuel Substances 0.000 abstract description 17
- 229920000557 Nafion® Polymers 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 6
- 230000000704 physical effect Effects 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 2
- 230000005540 biological transmission Effects 0.000 abstract 1
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- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
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- DHFODCCTNFXCCQ-UHFFFAOYSA-N 1-methylpyrrolidine-2,3-dione Chemical compound CN1CCC(=O)C1=O DHFODCCTNFXCCQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
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- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
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- 229920005597 polymer membrane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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Abstract
【解決手段】本発明の電解質膜の製造方法は、乾燥したPEEKをメチル硫酸溶液に溶解させる段階と、前記溶液に硫酸溶液を希釈して硫酸基を付着する段階と、得られた物質を沈殿、ろ過及び洗浄する段階と、有機溶媒に溶解させる段階及び固形化する段階とからなる。これにより、メタノール透過度をナフィオンに比べて1/10の低い水準に抑え、イオン伝導度は一定水準に維持しながら、ヤング率の値が約10倍上昇した効果を有する。また、有機溶媒を選択することにより、電解質膜の物性を調節できる。
【選択図】図2
Description
(2)本発明は、前記有機溶媒が、ジメチルホルムアミド、ジメチルアセトアミド又は1−メチル−2−ピロリジノンであることを特徴とする上記(1)に記載のPEEK電解質膜の製造方法を提供する。
(3)本発明は、前記PEEK高分子の重量平均分子量が70,000〜100,000であることを特徴とする上記(1)に記載のPEEK電解質膜の製造方法を提供する。
(4)本発明は、a)十分に乾燥したPEEKをメチル硫酸溶液に溶解させる段階と、b)前記溶液に硫酸溶液を希釈して硫酸基を付着する段階と、c)前記段階b)で収得した物質を沈殿、ろ過及び洗浄する段階と、d)前記段階c)で得られた物質を有機溶媒に溶解させる段階と、e)前記段階d)で得られた溶液を固形化する段階とを含むことを特徴とする電解質膜の製造方法を提供する。
(5)本発明は、前記段階a)は、PEEKをメチル硫酸溶液に15〜25重量%の含有量で混合した後、攪拌して溶解させることを特徴とする上記(4)に記載の電解質膜の製造方法を提供する。
(6)本発明は、前記段階b)は、段階a)で収得したPEEK溶液に90〜100%の硫酸水溶液をメチル硫酸容量の5〜10倍程度加えた後、窒素雰囲気下で保持して硫酸基を付着することを特徴とする上記(4)に記載の電解質膜の製造方法を提供する。
(7)本発明は、前記段階c)は、段階b)で収得したsPEEK(硫酸基が付着されたPEEK)を過量の0℃の水に沈殿させ、ろ過した後、洗浄することにより行われ、更に室温で乾燥させて収得した物質を粉砕して60〜100℃で24時間保持させる段階を含むことを特徴とする上記(4)に記載の電解質膜の製造方法を提供する。
(8)本発明は、上記(1)から(7)のいずれか一項の方法により製造されることを特徴とするsPEEKプロトン電解質膜を提供する。
a)十分に乾燥したPEEKをメチル硫酸溶液に入れて溶解させる段階と、b)前記溶液に硫酸溶液を希釈して硫酸基を付着する段階と、
c)前記段階b)で収得した物質を沈殿、ろ過及び洗浄する段階と、
d)前記段階c)で得られた物質を有機溶媒に溶解させる段階と、
e)前記段階d)で得られた溶液を板上で数日間適正温度と真空状態で保持して固形化する段階。
% water uptake=(Wwet−Wdry)×100/Wdry
WwetとWdryは、それぞれ水分含有膜と乾燥した膜の 水分含有量を示す。
Claims (8)
- 有機溶媒乾燥法による均一に硫酸基が付着されたPEEK電解質膜の製造方法。
- 前記有機溶媒が、ジメチルホルムアミド、ジメチルアセトアミド又は1−メチル−2−ピロリジノンであることを特徴とする請求項1に記載のPEEK電解質膜の製造方法。
- 前記PEEK高分子の重量平均分子量が70,000〜100,000であることを特徴とする請求項1に記載のPEEK電解質膜の製造方法。
- a)十分に乾燥したPEEKをメチル硫酸溶液に溶解させる段階と、
b)前記溶液に硫酸溶液を希釈して硫酸基を付着する段階と、
c)前記段階b)で収得した物質を沈殿、ろ過及び洗浄する段階と、
d)前記段階c)で得られた物質を有機溶媒に溶解させる段階と、
e)前記段階d)で得られた溶液を固形化する段階と
を含む電解質膜の製造方法。 - 前記段階a)は、PEEKをメチル硫酸溶液に15〜25重量%の含有量で混合した後、攪拌して溶解させることを特徴とする請求項4に記載の電解質膜の製造方法。
- 前記段階b)は、段階a)で収得したPEEK溶液に90〜100%の硫酸水溶液をメチル硫酸容量の5〜10倍程度加えた後、窒素雰囲気下で保持して硫酸基を付着することを特徴とする請求項4に記載の電解質膜の製造方法。
- 前記段階c)は、段階b)で収得したsPEEK(硫酸基が付着されたPEEK)を過量の0℃の水に沈殿させ、ろ過した後、洗浄することにより行われ、更に室温で乾燥させて収得した物質を粉砕して60〜100℃で24時間保持させる段階を含むことを特徴とする請求項4に記載の電解質膜の製造方法。
- 請求項1〜7のいずれか一項の方法により製造されることを特徴とするsPEEKプロトン電解質膜。
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Application Number | Priority Date | Filing Date | Title |
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KR10-2007-0101329 | 2007-10-09 | ||
KR1020070101329A KR100928718B1 (ko) | 2007-10-09 | 2007-10-09 | 유기 용매 건조법에 의한 균일하게 황산기가 부착된peek 전해질 막의 제조 방법 |
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JP2009094070A true JP2009094070A (ja) | 2009-04-30 |
JP5007908B2 JP5007908B2 (ja) | 2012-08-22 |
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JP2008261052A Expired - Fee Related JP5007908B2 (ja) | 2007-10-09 | 2008-10-07 | 電解質膜の製造方法 |
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JP (1) | JP5007908B2 (ja) |
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CN (1) | CN101407591A (ja) |
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JP2015143753A (ja) * | 2014-01-31 | 2015-08-06 | 株式会社トスカバノック | 係止ピン材及びその成形方法と成形された係止ピン材の使用方法 |
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KR101609271B1 (ko) * | 2009-12-11 | 2016-04-06 | 삼성전자주식회사 | 유무기 복합 프로톤 전도체, 이를 포함하는 연료전지용 전극과 전해질막 및 이를 채용한 연료전지 |
US9077014B2 (en) * | 2011-04-01 | 2015-07-07 | The Hong Kong University Of Science And Technology | Self-humidifying membrane and self-humidifying fuel cell |
ES2606356T3 (es) * | 2011-12-20 | 2017-03-23 | Ingeteam Power Technology, S.A. | Diafragma de speek para electrolisis alcalina y su uso |
US9099711B2 (en) | 2013-09-11 | 2015-08-04 | King Fahd University Of Petroleum And Minerals | Fuel cell membrane |
CN111193054B (zh) * | 2020-01-09 | 2022-08-02 | 安徽师范大学 | 一种质子交换膜的制备方法 |
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JP2015143753A (ja) * | 2014-01-31 | 2015-08-06 | 株式会社トスカバノック | 係止ピン材及びその成形方法と成形された係止ピン材の使用方法 |
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US20090092880A1 (en) | 2009-04-09 |
KR100928718B1 (ko) | 2009-11-27 |
CN101407591A (zh) | 2009-04-15 |
JP5007908B2 (ja) | 2012-08-22 |
KR20090036260A (ko) | 2009-04-14 |
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