Novel partially fluorinated sulfonated poly(arylenethioether)s and poly(aryleneether)s prepared from octafluorotoluene and pentafluoropyridine, and their blends with PBI-Celazol

European Polymer Journal

Volumn 49, Issue 2, 2013, Pages 518-531

  Seyb, Corina ^a   Kerres, Jochen ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Blends; Gel permeation chromatography (GPC); High temperature materials; Oligomers; Partially fluorinated polymers; Polycondensation

Indexed keywords

ARYLENE; BLEND MEMBRANES; BLENDS; C-F BONDS; C-H BOND; DEGRADATION PROCESS; FLUORINATED POLYMERS; HIGH TEMPERATURE MATERIALS; ONSET TEMPERATURE; OXIDATIVE STABILITY; PENTAFLUOROPYRIDINE; SULFONIC ACID; SULFONIC ACID GROUPS; TRIFLUOROMETHYL;

CHEMICAL STABILITY; CHROMATOGRAPHY; FLUORINE; GEL PERMEATION CHROMATOGRAPHY; IONOMERS; OLIGOMERS; POLYCONDENSATION; POLYMERS; THERMODYNAMIC STABILITY;

BLENDING;

EID: 84873143030     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2012.11.002     Document Type: Article

References (47)

1. J.M. Andujar, and F. Segura Fuel cells: history and updating. A walk along two centuries Renewable Sustainable Energy 13 9 2009 2309 2322
2. Q. Li, R. He, J.O. Jensen, and N. Bjerrum Approaches and recent development of polymer electrolyte membranes for fuel cells operating above 100 °C J Chem Mater 15 2003 4896
3. Y. Li, F. Wang, J. Yang, D. Liu, A. Roy, and S. Case Synthesis and characterization of controlled molecular weight disulfonated poly(arylene ether sulfone) copolymers and their applications to proton exchange membranes Polymer 47 2006 4210
4. Q. Li, R. He, J.-A. Gao, J.O. Jensen, and N.J. Bjerrum The CO poisoning effect in PEMFCs operational at temperatures up to 200 °C J Electrochem Soc 150 2003 A1599 A1605
5. C.-P. Wang, H.-S. Chu, Y.-Y. Yan, and K.-L. Hsueh Transient evolution of carbon monoxide poisoning effect of PBI membrane fuel cells J Power Sources 170 2007 235 241
6. P. Krishnan, J.-S. Park, and C.-S. Kim Performance of a poly(2,5-benzimidazole) membrane based high temperature PEM fuel cell in the presence of carbon monoxide J Power Sources 159 2006 817 823
7. Faure S, Mercier R, Aldebert P, Pineri M, Sillion B. French Patent, 9605707; 1996.
8. T. Watari, J. Fang, K. Tanaka, H. Kita, K.-I. Okamoto, and T. Hirano Synthesis, water stability and proton conductivity of novel sulfonated polyimides from 4,4′-bis(4-aminophenoxy)biphenyl-3,3′-disulfonic acid J Membr Sci 230 2004 111 120
9. F. Lufrano, I. Gatto, P. Staiti, V. Antonucci, and E. Passalacqua Sulfonated polysulfone ionomer membranes for fuel cells Solid State Ionics 145 2001 47 51
10. Y. Gao, G.P. Robertson, M.D. Guiver, S.D. Mikhailenko, and S. Kaliaguine Synthesis of poly(arylene ether ether ketone ketone) copolymers containing pendant sulfonic acid groups bonded to naphthalene as proton exchange membrane materials Macromolecules 37 2004 6748 6754
11. M. Gil, X. Ji, X. Li, H. Na, J.E. Hampsey, and Y. Lu Direct synthesis of sulfonated aromatic poly(ether ether ketone) proton exchange membranes for fuel cell applications J Membr Sci 234 2004 75 81
12. X. Jin, M.T. Bishop, T.S. Ellis, and F.E. Karasz A sulphonated poly(ary1 ether ketone) Br Polym J 17 1985 4 10
13. P. Xing, G.P. Robertson, M.D. Guiver, S.D. Mikhailenko, and S. Kaliaguine Sulfonated poly(aryl ether ketone)s containing the hexafluoroisopropylidene diphenyl moiety prepared by direct copolymerization, as proton exchange membranes for fuel cell application Macromolecules 37 2004 7960 7967
14. M.A. Hickner, H. Ghassemi, Y.S. Kim, B.R. Einsla, and J.E. McGrath Alternative polymer systems for proton exchange membranes (PEMs) Chem Rev 104 2004 4587 4612
15. F. Wang, M. Hickner, Y.S. Kima, T.A. Zawodzinkski, and J.E. McGrath Direct polymerization of sulfonated poly(arylene ether sulfone) random (statistical) copolymers: candidates for new proton exchange membranes J Membr Sci 197 2002 231 242
16. S. Kim, D.A. Cameron, Y. Lee, J.R. Reynolds, and C.R. Savage Aromatic and rigid rod polyelectrolytes based on sulfonated poly(benzobisthiazoles) J Polym Sci Part A: Polym Chem 34 1996 481 492
17. T. Higashihara, K. Matsumoto, and M. Ueda Sulfonated aromatic hydrocarbons polymers as proton exchange membranes for fuel cells Polymer 50 2009 5341 5357
18. N.N. Krishnan, H.-J. Lee, H.-J. Kim, J.-Y. Kim, I. Hwang, and J.H. Janh Sulfonated poly(ether sulfone)/sulfonated polybenzimidazole blend membrane for fuel cell applications Eur Poly J 46 7 2010 1633 1641
19. J.J. Luo, S.J. Wang, M. Xiao, D.M. Han, and D.M. Meng Fluorene-containing block sulfonated poly(ether ether ketone) as proton-exchange membrane for PEM fuel cell application Eur Poly J 46 8 2010 1736 1744
20. L. Kwan-Soo, J. Myung-Hwan, L. Jung-Pil, K. Young-Jea, and L. Jae-Suk Synthesis and characterization of highly fluorinated cross-linked aromatic polyethers for polymer electrolytes Chem Mater 22 2010 5500 5511
21. D.S. Kim, G.P. Robertson, M.D. Guiver, and M.Y. Lee Synthesis of highly fluorinated poly(arylene ether)s copolymers for proton exchange membrane materials J Membr Sci 281 2006 111 120
22. J.A. Kerres, D. Xing, and F. Schönberger Comparative investigation of novel PBI blend ionomer membranes from nonfluorinated and partially fluorinated poly arylene ethers J Polym Sci Part B: Polym Phys 44 2006 2311 2326
23. F. Schönberger, M. Hein, and J.A. Kerres Preparation and characterisation of sulfonated partially fluorinated statistical poly(arylene ether sulfone)s and their blends with PBI Solid State Ionics 178 7-10 2007 547 554
24. 4. Part I. Synthesis and characterisation of polymers and binary blend membranes Fuel Cells 8 3-4 2008 175 187
25. F. Schönberger, A. Chromik, and J.A. Kerres Partially fluorinated poly(arylene ether)s: investigation of the dependence of monomeric structures on polymerisability and degradation during sulfonation Polymer 51 19 2010 4299 4313
26. E.K. Pefkianakis, V. Deimede, M.K. Daletou, N. Gourdoupi, and J. Kallitsis Novel polymer electrolyte membrane, based on pyridine containing poly(ether sulfone), for application in high-temperature fuel cells Macromol Rapid Commun 26 2005 1724 1728
27. M. Geormezi, V. Deimede, N. Gourdoupi, N. Triantafyllopoulos, S. Neophytides, and J.K. Kallitsis Novel pyridine-based poly(ether sulfones) and their study in high temperature PEM fuel cells Macromolecules 41 2008 9051 9056
28. A.D. Modestov, M.R. Tarasevich, V. Filimonov, and Ya Zagudaeva Electrocatalytic oxidation of methanol at 2-aminophenoxazin-3-one-functionalized multiwalled carbon nanotubes supported PtRu nanoparticles Electrochim Acta 54 2009 7121 7127
29. S. Matar, A. Higier, and L. Hongtan The effects of excess phosphoric acid in a polybenzimidazole-based high temperature proton exchange membrane fuel cell J Power Sources 195 2010 181 184
30. 4-doped PBI-based high temperature PEMFC J Membr Sci 306 2007 47 55
31. J. Kerres, A. Ullrich, F. Meier, and Th. Häring Synthesis and characterization of novel acid-base polymer blends for application in membrane fuel cells Solid State Ionics 125 1999 243 249
32. J. Kerres, A. Ullrich, Th. Häring, M. Baldauf, U. Gebhardt, and W. Preidel Preparation, characterization and fuel cell application of new acid-base blend membranes J New Mat Electrochem Syst 3 2000 229 239
33. C. Hasiotis, Li Quingfeng, V. Deimede, J.K. Kallitsis, C.G. Kontoyannis, and N.J. Bjerrum Development and characterization of acid-doped polybenzimidazole/sulfonated polysulfone blend polymer electrolytes for fuel cells J Electrochem Soc 148 5 2001 A513 A519
34. 4. Part II. Characterization and fuel cell tests of the ternary membranes Fuel Cells 8 3-4 2008 188 199
35. Y. Zhai, H. Zhang, Y. Zhang, and D. Xing A novel H3PO4/Nafion PBI composite membrane for enhanced durability of high temperature PEM fuel cells J Power Sources 169 2007 259 264
36. Q.F. Li, H.C. Rudbeck, A. Chromik, J.O. Jensen, C. Pan, and T. Steenberg Properties, degradation and high temperature fuel cell test of different types of PBI and PBI blend membranes J Memb Sci 347 1-2 2010 260 270
37. J.A. Kerres, A. Katzfuß, and A. Chromik Sulfonated low-cost ionomers as acidic cross-linkers for high-temperature PBIOO® membranes ECS Trans 33 1 2010 797
38. P. Sartori, and G. Bauer 2,3,5,6-Tetrafluorbenzoldisulfonsäure aus pentaflurbenzolsulfonsäure J Fluorine Chem 12 1978 203
39. R.E. Banks, J.E. Burgess, W.M. Cheng, and N. Haszeldine Heterocyclic polyfluoro-compounds. Part IV. I nucleophilic substitutionin pentafluoropyridine: the preparation and properties of some 4-substituted 2,3,5,6-tetrajluoropyridines. J Chem Soc 1965 575 581
40. R.D. Chambers, J. Hutchinson, and W.K.R. Musgrave Polyfluoroheterocyclic compounds. Part II: nucleophilic substitution in pentafluoropyridine J Chem Soc 1964 3736 3739
41. D.J. Alsop, J. Burdon, and J.C. Tatlow Aromatic polyfuorocompounds. Part XI some replacement reactions of octafluorotoluene J Chem Soc 1962 1801 1805
42. L. Hu, H. Zhu, D.-M. Du, and J. Xu Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines J Org Chem 72 2007 4543
43. B. Wang, W. Zhang, L. Zhang, D.-M. Du, G. Liu, and J. Xu Versatile synthesis of free and N-benzyloxycarbonyl-protected 2,2-disubstituted taurines Eur J Org Chem 350 2008
44. J. Huang, F. Wang, D.-M. Du, and J. Xu An expeditious synthesis of 1-substituted and cyclic taurines Synthesis 13 2005 2122
45. D. Xing, and J. Kerres Improvement of synthesis procedure and characterization of sulfonated poly(arylene ether sulfone) for proton exchange membranes J New Mat Electrochem Syst 9 2006 51 60
46. A. Panchenko, H. Dilger, E. Möller, T. Sixt, and E. Roduner In situ EPR investigation of polymer electrolyte membrane degradation in fuel cell applications J Power Sources 127 2004 325 330
47. R. Bouchet, and E. Siebert Proton conduction in acid doped polybenzimidazole Solid State Ionics 118 1999 287 299