JP2009544831A5 - - Google Patents
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- Publication number
- JP2009544831A5 JP2009544831A5 JP2009522204A JP2009522204A JP2009544831A5 JP 2009544831 A5 JP2009544831 A5 JP 2009544831A5 JP 2009522204 A JP2009522204 A JP 2009522204A JP 2009522204 A JP2009522204 A JP 2009522204A JP 2009544831 A5 JP2009544831 A5 JP 2009544831A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- sulfonated
- polyarylene compound
- aromatic group
- side chain
- 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
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- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229920000412 polyarylene Polymers 0.000 claims description 17
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- -1 arylene compound Chemical class 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 229920000642 polymer Polymers 0.000 claims 6
- 125000000732 arylene group Chemical group 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 claims 2
- 229930185605 Bisphenol Natural products 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- QWQONZVLXJGXHV-UHFFFAOYSA-N [chlorosulfonyloxy(dimethyl)silyl]methane Chemical compound C[Si](C)(C)OS(Cl)(=O)=O QWQONZVLXJGXHV-UHFFFAOYSA-N 0.000 claims 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 claims 1
- BWQOPMJTQPWHOZ-UHFFFAOYSA-N (2,3-difluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1F BWQOPMJTQPWHOZ-UHFFFAOYSA-N 0.000 claims 1
- HUYKZYIAFUBPAQ-UHFFFAOYSA-N (2-hydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1O HUYKZYIAFUBPAQ-UHFFFAOYSA-N 0.000 claims 1
- LJQVLJXQHTULEP-UHFFFAOYSA-N (3-hydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC(O)=C1 LJQVLJXQHTULEP-UHFFFAOYSA-N 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 1
- IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 claims 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 claims 1
- BKXFWZWEQCJPCN-UHFFFAOYSA-N 2,3,5,6-tetraphenylbenzene-1,4-diol Chemical compound C=1C=CC=CC=1C1=C(O)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(O)=C1C1=CC=CC=C1 BKXFWZWEQCJPCN-UHFFFAOYSA-N 0.000 claims 1
- UNEJGFDSCQMCLN-UHFFFAOYSA-N 2,5-bis(2-phenylphenyl)benzene-1,4-diol Chemical compound OC1=CC(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C(O)C=C1C1=CC=CC=C1C1=CC=CC=C1 UNEJGFDSCQMCLN-UHFFFAOYSA-N 0.000 claims 1
- BVVCBZSERKSMIE-UHFFFAOYSA-N 2,5-diphenylbenzene-1,4-diol Chemical compound OC1=CC(C=2C=CC=CC=2)=C(O)C=C1C1=CC=CC=C1 BVVCBZSERKSMIE-UHFFFAOYSA-N 0.000 claims 1
- ZQNMHKRUIHKZOV-UHFFFAOYSA-N 2-(2-phenylphenyl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 ZQNMHKRUIHKZOV-UHFFFAOYSA-N 0.000 claims 1
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 claims 1
- ZDXTXFGQXVYVHF-UHFFFAOYSA-N 2-anthracen-1-ylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C3=CC4=CC=CC=C4C=C3C=CC=2)=C1 ZDXTXFGQXVYVHF-UHFFFAOYSA-N 0.000 claims 1
- JBBUVXYGGLQJPN-UHFFFAOYSA-N 2-naphthalen-1-ylnaphthalene-1,4-diol Chemical compound C1=CC=C2C(C=3C=C(C4=CC=CC=C4C=3O)O)=CC=CC2=C1 JBBUVXYGGLQJPN-UHFFFAOYSA-N 0.000 claims 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 claims 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- MYLHDKKILSIAGC-UHFFFAOYSA-N [2-(4-fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 MYLHDKKILSIAGC-UHFFFAOYSA-N 0.000 claims 1
- HZWXJJCSDBQVLF-UHFFFAOYSA-N acetoxysulfonic acid Chemical compound CC(=O)OS(O)(=O)=O HZWXJJCSDBQVLF-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 150000004074 biphenyls Chemical class 0.000 claims 1
- MIYITCTXDGORJJ-UHFFFAOYSA-N bis(4-fluorophenyl)-oxophosphanium Chemical compound C1=CC(F)=CC=C1[P+](=O)C1=CC=C(F)C=C1 MIYITCTXDGORJJ-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000446 fuel Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 238000001471 micro-filtration Methods 0.000 claims 1
- 238000001728 nano-filtration Methods 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 238000001223 reverse osmosis Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 125000003375 sulfoxide group Chemical group 0.000 claims 1
- 238000000108 ultra-filtration Methods 0.000 claims 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006036496A DE102006036496A1 (de) | 2006-07-28 | 2006-07-28 | Sulfonierte Polyarylverbindungen, Membranmaterial daraus, Verfahren zu ihrer Herstellung und Verwendung |
| DE102006036496.1 | 2006-07-28 | ||
| PCT/EP2007/057280 WO2008012222A2 (de) | 2006-07-28 | 2007-07-13 | Sulfonierte polyarylenverbindungen, membranmaterial daraus, verfahren zu ihrer herstellung und verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009544831A JP2009544831A (ja) | 2009-12-17 |
| JP2009544831A5 true JP2009544831A5 (enExample) | 2012-12-13 |
| JP5306199B2 JP5306199B2 (ja) | 2013-10-02 |
Family
ID=38719910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009522204A Expired - Fee Related JP5306199B2 (ja) | 2006-07-28 | 2007-07-13 | スルホン化したポリアリーレン化合物、前記化合物からの膜材料、その製造方法及び使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8163864B2 (enExample) |
| EP (1) | EP2046491B1 (enExample) |
| JP (1) | JP5306199B2 (enExample) |
| AT (1) | ATE467452T1 (enExample) |
| DE (2) | DE102006036496A1 (enExample) |
| WO (1) | WO2008012222A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101550595B1 (ko) * | 2009-04-10 | 2015-09-07 | 주식회사 동진쎄미켐 | 폴리술폰계 중합체, 이를 포함하는 고분자 전해질막, 이를 포함하는 막-전극 접합체, 이를 채용한 연료전지 및 상기 중합체의 제조방법 |
| CN101580583B (zh) * | 2009-06-26 | 2011-03-30 | 金发科技股份有限公司 | 采用四元共聚技术制备聚芳醚酮类共聚物的方法 |
| JP5896295B2 (ja) * | 2011-07-04 | 2016-03-30 | 東洋紡株式会社 | ナノろ過用の分離膜 |
| JP5896294B2 (ja) * | 2011-07-04 | 2016-03-30 | 東洋紡株式会社 | かん水淡水化用の逆浸透膜 |
| JP5252333B1 (ja) * | 2011-07-04 | 2013-07-31 | 東洋紡株式会社 | 排水処理用の逆浸透膜 |
| WO2014054346A1 (ja) * | 2012-10-04 | 2014-04-10 | 東洋紡株式会社 | 複合分離膜 |
| CN103788374A (zh) * | 2012-10-29 | 2014-05-14 | 中国石油化工股份有限公司 | 一种磺化聚芳醚砜和反渗透膜及其制备方法 |
| KR101882863B1 (ko) * | 2013-01-10 | 2018-08-24 | 삼성전자주식회사 | 고분자, 그 제조방법, 이로부터 형성된 복합체, 이를 포함한 전극과 복합막 및 이를 채용한 연료전지 |
| KR101605049B1 (ko) | 2013-05-10 | 2016-03-22 | 한국화학연구원 | 조절된 갯수의 술폰산기가 치환된 폴리페닐술폰 구조를 포함하는 이온전도성 고분자 및 이의 용도 |
| WO2016102277A1 (en) * | 2014-12-22 | 2016-06-30 | Solvay Specialty Polymers Usa, Llc | Methods for making polyarylene ether sulfone (paes) polymers with silylated terphenyl compounds |
| WO2018069353A1 (en) * | 2016-10-11 | 2018-04-19 | Solvay Specialty Polymers Italy S.P.A. | Blocky poly(ether ether ketone) copolymers and corresponding synthesis methods and articles |
| JP6446572B1 (ja) * | 2018-01-18 | 2018-12-26 | 住友化学株式会社 | 芳香族ポリスルホン樹脂およびその膜 |
| CN111116914A (zh) * | 2019-12-26 | 2020-05-08 | 白银图微新材料科技有限公司 | 聚硫酸(氨)酯聚合物为原料制备磺化聚硫酸(氨)酯的合成方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2040950A5 (enExample) * | 1969-04-30 | 1971-01-22 | Rhone Poulenc Sa | |
| FR2214675A1 (en) * | 1973-01-23 | 1974-08-19 | Rhone Poulenc Sa | Reverse osmosis of aq. phenol solns - using a sulphonated polyarylether semi-permeable membrane |
| JPS6375031A (ja) * | 1985-06-12 | 1988-04-05 | アモコ・コ−ポレイション | スルホン化ポリ（アリ−ルエ−テル）樹脂の製造方法 |
| EP0388358B1 (de) * | 1989-03-17 | 1996-09-25 | Sumitomo Chemical Company Limited | Neue Polyarylenether |
| US5071448A (en) * | 1990-12-05 | 1991-12-10 | Union Carbide Industrial Gases Technology Corporation | Semipermeable membranes based on certain sulfonated substituted polysulfone polymers |
| EP0501922A2 (de) * | 1991-03-01 | 1992-09-02 | Ciba-Geigy Ag | Gemische auf Basis von Polyamid-Polyimid-Blockcopolymeren |
| DE59309908D1 (de) * | 1992-06-13 | 2000-01-27 | Aventis Res & Tech Gmbh & Co | Polymerelektrolyt-Membran und Verfahren zu ihrer Herstellung |
| JPH1074509A (ja) * | 1996-08-30 | 1998-03-17 | Shin Etsu Chem Co Ltd | 水素吸蔵合金粉末の製造方法、及び、その方法によって得られた水素吸蔵合金粉末を用いた電極 |
| DE19909841A1 (de) * | 1999-03-06 | 2000-09-07 | Inst Polymerforschung Dresden | Mehrschichtmembranen und Verfahren zu ihrer Herstellung |
| DE10201691A1 (de) * | 2001-01-19 | 2002-09-05 | Honda Motor Co Ltd | Polymerelektrolytmembran, Verfahren zu deren Herstellung und Membranelektrodenanordnung und Polymerelektrolytbrennstoffzelle, die diese umfasst |
| CA2442633C (en) * | 2001-03-30 | 2010-02-09 | Honda Giken Kogyo Kabushiki Kaisha | Solid polymer type fuel cell |
| US7601448B2 (en) * | 2001-07-03 | 2009-10-13 | Sumitomo Chemical Company, Limited | Polymer electrolyte membrane and fuel cell |
| DE10149716A1 (de) * | 2001-09-28 | 2003-04-30 | Inst Polymerforschung Dresden | Polymere Brennstoffzellen-Membran und Verfahren zu ihrer Herstellung |
| JP4208455B2 (ja) * | 2001-11-16 | 2009-01-14 | 東洋紡績株式会社 | スルホン化フッ素含有重合体、それを含有する樹脂組成物および高分子電解質膜 |
| EP1420473B1 (en) * | 2002-11-18 | 2006-04-12 | HONDA MOTOR CO., Ltd. | Electrode structure for polymer electrolyte fuel cells, and polymer electrolyte fuel cell using the same |
| JP4135558B2 (ja) * | 2003-05-21 | 2008-08-20 | Ｊｓｒ株式会社 | スルホン酸基を有するポリアリーレンおよびその製造方法、ならび直接メタノール型燃料電池用プロトン伝導膜 |
| JP2005060484A (ja) * | 2003-08-08 | 2005-03-10 | Jsr Corp | スルホン酸基を有するポリアリーレン共重合体およびその製造方法、ならびに高分子固体電解質およびプロトン伝導膜 |
| KR100748049B1 (ko) * | 2003-10-02 | 2007-08-09 | 고쿠리츠다이가쿠호징 야마나시다이가쿠 | 술폰산화 방향족 폴리에테르, 그의 제조 방법, 및 전해질막 |
| CN1235849C (zh) * | 2003-10-24 | 2006-01-11 | 中国科学院广州化学研究所 | 磺化聚芳醚化合物及其中间体及它们的合成和应用 |
| EP1630187B1 (en) * | 2004-08-30 | 2008-05-21 | JSR Corporation | Sulfonic group-containing polyarylene block copolymer, process for production thereof, solid polymer electrolyte and proton conductive membrane |
| CA2624452C (en) * | 2005-09-30 | 2015-04-07 | Battelle Memorial Institute | Polymers for use in fuel cell components |
| WO2008009102A1 (en) * | 2006-07-21 | 2008-01-24 | National Research Council Of Canada | Poly(aryl ether) with pendent sulfonic acid phenyl groups |
-
2006
- 2006-07-28 DE DE102006036496A patent/DE102006036496A1/de not_active Withdrawn
-
2007
- 2007-07-13 US US12/375,385 patent/US8163864B2/en not_active Expired - Fee Related
- 2007-07-13 EP EP07787548A patent/EP2046491B1/de not_active Not-in-force
- 2007-07-13 AT AT07787548T patent/ATE467452T1/de active
- 2007-07-13 JP JP2009522204A patent/JP5306199B2/ja not_active Expired - Fee Related
- 2007-07-13 DE DE502007003767T patent/DE502007003767D1/de active Active
- 2007-07-13 WO PCT/EP2007/057280 patent/WO2008012222A2/de not_active Ceased
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