JPS59196322A - 難スルホン化ポリ(エ−テルスルホン)の不均一スルホン化方法 - Google Patents
難スルホン化ポリ(エ−テルスルホン)の不均一スルホン化方法Info
- Publication number
- JPS59196322A JPS59196322A JP58235197A JP23519783A JPS59196322A JP S59196322 A JPS59196322 A JP S59196322A JP 58235197 A JP58235197 A JP 58235197A JP 23519783 A JP23519783 A JP 23519783A JP S59196322 A JPS59196322 A JP S59196322A
- Authority
- JP
- Japan
- Prior art keywords
- sulfonation
- ether sulfone
- poly
- polymer
- sulfonated
- 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.)
- Granted
Links
- 238000006277 sulfonation reaction Methods 0.000 title claims description 20
- 229920006393 polyether sulfone Polymers 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical group O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 7
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- -1 poly(ether sulfones Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000012510 hollow fiber Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 238000000333 X-ray scattering Methods 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/66—Polymers having sulfur in the main chain, with or without nitrogen, oxygen or carbon only
- B01D71/68—Polysulfones; Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/453,162 US4413106A (en) | 1982-12-27 | 1982-12-27 | Heterogeneous sulfonation process for difficultly sulfonatable poly(ether sulfone) |
US453162 | 1982-12-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59196322A true JPS59196322A (ja) | 1984-11-07 |
JPH0321565B2 JPH0321565B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-03-25 |
Family
ID=23799420
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58235197A Granted JPS59196322A (ja) | 1982-12-27 | 1983-12-15 | 難スルホン化ポリ(エ−テルスルホン)の不均一スルホン化方法 |
Country Status (7)
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0216126A (ja) * | 1988-04-30 | 1990-01-19 | Akzo Nv | 芳香族ポリエーテルスルホンのスルホン化方法 |
JP4796274B2 (ja) * | 2001-09-26 | 2011-10-19 | ビクトレックス マニュファクチャリング リミテッド | 燃料電池、燃料電池用の高分子電解質膜および膜電極アセンブリ、ならびに燃料電池の作製方法 |
US9228060B2 (en) | 2011-12-22 | 2016-01-05 | Konishi Chemical Ind. Co., Ltd. | Method for manufacturing sulfonated aromatic polymer |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4508852A (en) * | 1983-09-22 | 1985-04-02 | Albany International Corp. | Compositions and method of preparation by chlorosulfonation of difficultly sulfonatable poly(ether sulfone) |
US4625000A (en) * | 1985-06-12 | 1986-11-25 | Union Carbide Corporation | Process for preparing sulfonated poly(aryl ether) resins |
US4990252A (en) * | 1987-02-04 | 1991-02-05 | Hydanautics | Stable membranes from sulfonated polyarylethers |
JP2694341B2 (ja) * | 1987-02-04 | 1997-12-24 | ハイドロノーティクス | 改良された耐酸化性膜およびその製造方法 |
KR920000944B1 (ko) * | 1989-11-11 | 1992-01-31 | 한국과학기술연구원 | 표면 개질된 다층 복합 산소 부화막 및 그 제조방법 |
US6248469B1 (en) | 1997-08-29 | 2001-06-19 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
US7550216B2 (en) * | 1999-03-03 | 2009-06-23 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
DE10007272B4 (de) | 2000-02-17 | 2005-04-07 | Membrana Gmbh | Blockcopolymere mit sulfonierten Polyethersulfoneinheiten |
KR101367535B1 (ko) * | 2006-02-16 | 2014-03-14 | 바스프 에스이 | 고온 중합체의 포스포닐화를 위한 촉매 공정 |
US8455557B2 (en) | 2006-05-24 | 2013-06-04 | Ben Gurion University Of The Negev R&D Authority | Membranes, coatings and films and methods for their preparation |
US8661630B2 (en) * | 2008-05-21 | 2014-03-04 | Abbott Cardiovascular Systems Inc. | Coating comprising an amorphous primer layer and a semi-crystalline reservoir layer |
CN102405094A (zh) | 2009-02-19 | 2012-04-04 | 内盖夫研究与发展部本-古里安大学 | 耐化学性膜、涂层和膜层及它们的制备方法 |
WO2012081026A2 (en) | 2010-12-12 | 2012-06-21 | Ben-Gurion University Of The Negev Research And Development Authority | Anion exchange membranes, methods of preparation and uses |
US9172076B2 (en) | 2011-01-11 | 2015-10-27 | Etv Energy Ltd. | Membranes suitable for use as separators and electrochemical cells including such separators |
EP3340350B1 (en) | 2015-08-17 | 2020-05-20 | National Institute for Materials Science | Polyphenylsulfone-based proton conducting polymer electrolyte, proton conducting solid polymer electrolyte membrane and method for producing the same, electrode catalyst layer for solid polymer fuel cells and method for producing the same, and solid polymer fuel cells |
CN105833745A (zh) * | 2016-05-04 | 2016-08-10 | 浙江理工大学 | 一种聚乙二醇作为添加剂的亲水性聚醚砜超滤膜的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5190397A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-12-26 | 1976-08-07 | ||
JPS5756417A (en) * | 1980-07-25 | 1982-04-05 | Johnson & Johnson Prod Inc | Sulfonated poly(arylene ether sulfone) polymer as tooth dirt inhibitor |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2040950A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-04-30 | 1971-01-22 | Rhone Poulenc Sa | |
US3875096A (en) * | 1974-03-20 | 1975-04-01 | Us Interior | Process for the preparation of a stable salt form of a sulfonated polyarylether sulfone |
DE2415444A1 (de) * | 1974-03-29 | 1975-10-23 | Trw Inc | Verfahren zur enfernung unerwuenschter kristalliner anteile aus polysulfonharzen |
JPS5416378A (en) * | 1977-07-08 | 1979-02-06 | Asahi Chem Ind Co Ltd | Polysulfone semipermeable membrane |
EP0008894B1 (en) * | 1978-09-05 | 1983-02-23 | Imperial Chemical Industries Plc | Sulphonated polyarylethersulphone copolymers and process for the manufacture thereof |
-
1982
- 1982-12-27 US US06/453,162 patent/US4413106A/en not_active Expired - Lifetime
-
1983
- 1983-11-21 CA CA000441524A patent/CA1221491A/en not_active Expired
- 1983-12-08 IL IL70410A patent/IL70410A/xx not_active IP Right Cessation
- 1983-12-15 JP JP58235197A patent/JPS59196322A/ja active Granted
- 1983-12-22 AT AT83307902T patent/ATE33499T1/de not_active IP Right Cessation
- 1983-12-22 DE DE8383307902T patent/DE3376268D1/de not_active Expired
- 1983-12-22 EP EP83307902A patent/EP0112724B1/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5190397A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-12-26 | 1976-08-07 | ||
JPS5756417A (en) * | 1980-07-25 | 1982-04-05 | Johnson & Johnson Prod Inc | Sulfonated poly(arylene ether sulfone) polymer as tooth dirt inhibitor |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0216126A (ja) * | 1988-04-30 | 1990-01-19 | Akzo Nv | 芳香族ポリエーテルスルホンのスルホン化方法 |
JP4796274B2 (ja) * | 2001-09-26 | 2011-10-19 | ビクトレックス マニュファクチャリング リミテッド | 燃料電池、燃料電池用の高分子電解質膜および膜電極アセンブリ、ならびに燃料電池の作製方法 |
US9228060B2 (en) | 2011-12-22 | 2016-01-05 | Konishi Chemical Ind. Co., Ltd. | Method for manufacturing sulfonated aromatic polymer |
DE112012005418B4 (de) | 2011-12-22 | 2018-06-21 | Konishi Chemical Ind. Co., Ltd. | Verfahren zur Herstellung eines sulfonierten aromatischen Polymers |
Also Published As
Publication number | Publication date |
---|---|
EP0112724A1 (en) | 1984-07-04 |
IL70410A0 (en) | 1984-03-30 |
EP0112724B1 (en) | 1988-04-13 |
US4413106A (en) | 1983-11-01 |
JPH0321565B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-03-25 |
DE3376268D1 (en) | 1988-05-19 |
ATE33499T1 (de) | 1988-04-15 |
CA1221491A (en) | 1987-05-05 |
IL70410A (en) | 1986-10-31 |
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