Preparation and characterization of high-durability zwitterionic crosslinked proton exchange membranes

Journal of Membrane Science

Volumn 362, Issue 1-2, 2010, Pages 29-37

  Ye, Yun Sheng ^a   Chen, Wen Yi ^b   Huang, Yao Jheng ^a   Cheng, Ming Yao ^c   Yen, Ying Chieh ^a   Cheng, Chih Chia ^a   Chang, Feng Chih ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^b INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

Crosslinked membranes; Fuel cells; Polymer electrolyte membrane; Proton conductor; Sulfonated polymer

Indexed keywords

4-VINYLPYRIDINE; BROMOBUTANE; CROSS LINKED MEMBRANES; CROSSLINKED; CROSSLINKER; FLEXIBLE MEMBRANES; HIGH ENERGY DENSITIES; HIGH MECHANICAL STRENGTH; IONIC BONDING; MODEL REACTIONS; NAFION 117; NUCLEOPHILIC SUBSTITUTIONS; OXIDATIVE STABILITY; POLYMER-ELECTROLYTE MEMBRANE; PRACTICAL USE; PROTON CONDUCTOR; PROTON EXCHANGE MEMBRANES; RELATIVE HUMIDITIES; SULFONATED POLYMER; SULFONIC ACID; ZWITTER IONIC MOLECULE;

ATMOSPHERIC HUMIDITY; ELECTROLYTES; GAS FUEL PURIFICATION; ION EXCHANGE; METHANOL; METHANOL FUELS; NUCLEAR MAGNETIC RESONANCE; POLYMERS; PROTON EXCHANGE MEMBRANE FUEL CELLS (PEMFC); PROTONS; RESONANCE; STYRENE;

MEMBRANES;

1 BROMOBUTANE; 4 VINYLPYRIDINE; AMPHOLYTE; CHEMICAL AGENT; COPOLYMER; METHANOL; POLYSTYRENESULFONIC ACID; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CROSS LINKING; ENERGY RESOURCE; FUEL CELL; HUMIDITY; MEMBRANE; NUCLEAR MAGNETIC RESONANCE; PERMEABILITY; POLYMER ELECTROLYTE MEMBRANE; PRIORITY JOURNAL; PROTON TRANSPORT; TENSILE STRENGTH; THERMOSTABILITY; WATER TRANSPORT;

EID: 77955660308     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.memsci.2010.06.004     Document Type: Article

References (58)

1. Appleby A.J., Foulkes F.R. Fuel Cell Handbook 1989, Van Norstrand, New York.
2. Rikukawa M., Sanui K. Prog. Polym. Sci. 2000, 25:1463-1502.
3. Steele B.C.H., Heinzel A. Materials for fuel cell technologies. Nature (London) 2001, 414:345-352.
4. Gottesfeld S., Zawodzinski T.A. Polymer electrolyte fuel cells. Adv. Electrochem. Sci. Eng. 1997, 5:195-301.
5. Hickner M.A., Ghassemi H., Kim Y.S., Einsla B.R., McGrath J.E. Polymer system for proton exchange membranes. Chem. Rev. 2004, 104:4587-4612.
6. Miyatake K., Chikashige Y., Higuchi E., Watanabe M. Polymer electrolyte membranes for fuel cell applications. J. Am. Chem. Soc. 2007, 129:3879-3887.
7. Jannasch P., Parvole J. Poly(arylene ether sulfone)s with phosphonic acid and bis(phosphonic acid) on short alkyl side chains for proton exchange membranes. J. Mater. Chem. 2008, 18:5547-5556.
8. Hofmann M.A., Ambler C.M., Maher A.E., Chalkova E., Zhou X.Y., Lvov S.N., Allcock H.R. Synthesis of polyphosphazenes with sulfonimide side groups. Macromolecules 2002, 35:6490-6493.
9. Chuang S.W., Hsu S.L.C. Fluorine containing polybenzimidazole for high temperature fuel cell applications. J. Polym. Sci. Part A: Polym. Chem. 2006, 44:4508-4513.
10. Julien J., Régis M., Laurent G., Gérard G. Synthesis of sulfonated polybenzimidazoles from functionalized monomers. Macromolecules 2007, 40:983-989.
11. Asano N., Aoki M., Suzuki S., Miyatake K., Uchida H., Watanabe M. Aliphatic/aromatic polyimide ionomers as a proton conductive membrane for fuel cell applications. J. Am. Chem Soc. 2006, 16:4465-4467.
12. He B., Ho W.S.W. Poly(ethylene oxide) soft segment-containing sulfonated polyimide copolymers for high temperature proton-exchange membrane fuel cells. J. Membr. Sci. 2008, 313:75-85.
13. Li N., Cui Z., Zhang S., Li S. Synthesis and properties of novel polyimides from sulfonated binaphthalene dianhydride for proton exchange membranes. J. Polym. Sci. Part A: Polym. Chem. 2008, 46:2820-2832.
14. Li X., Zhang G., Xu D., Zhao C., Na H. Morphology study of sulfonated poly(ether ether ketone ketone)s membranes. J. Power Sources 2007, 165:701-707.
15. Kim D.S., Robertson P., Guiver M.D. Comb-shaped poly(arylene ether sulfone)s as proton exchange membranes. Macromolecules 2008, 41:2126-2134.
16. Tan S., Belanger D. Characterization and transport properties of Nafion/polyaniline composite membranes. J. Phys. Chem. B 2005, 109:23480-23490.
17. Deimede V., Voyiatzis G.A., Kallitsis J.K., Qingfeng L., Bjerrum N.J. Miscibility behavior of polybenzimidazole/sulfonated polysulfone blends for use in fuel cell applications. Macromolecules 2000, 33:7609-7617.
18. Schmeisser J., Holdcroft S., Yu J., Ngo T., McLean G. Photocuring and photolithography of proton conducting polymers bearing weak and strong acids. Chem. Mater. 2005, 17:387-394.
19. Zhong S., Fu T., Dou Z., Zhao C., Na H. Proton exchange membrane based on crosslinkable sulfonated poly(ether ether ketone)s. J. Power Sources 2006, 162:51-57.
20. Zhong S., Cui X., Cai H., Fu T., Zhao C., Na H. Crosslinked sulfonated poly(ether ether ketone) proton exchange membranes for direct methanol fuel cell applications. J. Power Sources 2007, 164:65-72.
21. Zhong S., Liu C., Na H. UV irradiation-induced crosslinked sulfonated poly(ether ether ketone) proton exchange membranes. J. Membr. Sci. 2009, 326:400-407.
22. Guo Q., Pintauro P.N., Tang H., O'Connor S. Sulfonated and crosslinked polyphosphazene-based proton exchange membranes. J. Membr. Sci. 1999, 154:175-181.
23. Lin C.W., Huang Y.F., Kannan A.M. Crosslinked poly(vinyl alcohol) and poly(styrene sulfonic acid-co-maleic anhydride) as proton exchange fuel cell membranes. J. Power Sources 2007, 164:449-456.
24. Lin C.W., Huang Y.F., Kannan A.M. Crosslinked poly(vinyl alcohol) and poly(styrene sulfonic acid-co-maleic anhydride)-based semi-interpenetrating network. J. Power Sources 2007, 171:340-347.
25. Ye Y.S., Yen Y.C., Cheng C.C., Chen W.Y., Tsai L.T., Chang F.C. Sulfonated poly(ether ether ketone) membranes crosslinked with containing benzoxazine monomer as proton exchange membranes. Polymer 2009, 50:3196-3203.
26. Yen Y.C., Ye Y.S., Cheng C.C., Chen W.Y., Tsai L.D., Huang J.M., Chang F.C. The effect of sulfonic acid groups within a polyhedral oligomeric silsesquioxane containing cross-linked proton exchange membrane. Polymer 2010, 51:84-89.
27. Sata T., Yamane Y., Matsusaki K. Preparation and properties of anion exchange membranes having pyridinium derivatives as anion exchange groups. J. Polym. Sci. Part A: Polym. Chem. 1998, 36:49-58.
28. Sata T., Nojima S. Transport properties of anion exchange membranes prepared by the reaction of crosslinked membranes having chloromethyl groups with 4-vinylpyridine and trimethylamine. J. Polym. Sci. Part B: Polym. Phys. 1999, 37:1773-1785.
29. Lee C.H., Part H.B., Chung Y.S., Lee Y.M., Freeman B.D. Sulfonated polyimide membranes crosslinked with N,N-Bis(2-hydroxyethyl)-2-aminoethanesulfonic acid. Macromolecules 2006, 39:755-764.
30. Yin Y., Hayashi S., Yamada Q., Kita H., Okamoto K.I. Branched/crosslinked sulfonated polyimide membranes for polymer electrolyte fuel cells. Macromol. Rapid. Commun. 2005, 26:696-700.
31. Gasa J.V., Weiss R.A., Shaw M.T. Ionic crosslinking of ionomer polymer electrolyte membranes using barium cations. J. Membr. Sci. 2007, 304:173-180.
32. Sakurai K., Douglas E.P., MacKnight W.J. Spectroscopic study of an ionic blend made from the acid form of sulfonated polystyrene and poly[ethyl acrylate-co-(4-vinylpyridine)]. Macromolecules 1992, 25:4506-4510.
33. Smith P., Eisenberg A. Infrared spectroscopic study of blends of poly(styrene-co-styrenesulfonic acid) with poly(styrene-co-(4-vinylpyridine)). Macromolecules 1994, 27:545-552.
34. Zundel G. Hydration and Intermolecular Interaction 1969, Academic Press, New York, 302 pp.
35. Chen W., Sauer J.A., Hara M. Homoblends made of poly(styrene-co-styrenesulfonic acid) and poly(styrene-co-vinylpyridine). Polymer 2003, 44:7729-7738.
36. Tian S.H., Shu D., Wang S.J., Xiao M., Meng Y.Z. Poly(arylene ether)s with sulfonic acid groups on the backbone and pendant for proton exchange membranes used in PEMFC applications. Fuel Cells 2007, 3:232-237.
37. Fu R.Q., Hong L., Lee J.Y. A hybrid proton-conducting interpenetrating polymer network. Fuel Cells 2008, 1:52-61.
38. Fu R.Q., Julius D., Hong L., Lee J.Y. PPO-based acid-base polymer blend membranes for direct methanol fuel cells. J. Membr. Sci. 2008, 322:331-338.
39. Watari T., Wang H.Y., Kuwahara K., Tanaka K., Kita H., Okamoto K. Water vapor sorption and diffusion properties of sulfonated polyimide membranes. J. Membr. Sci. 2003, 219:137-147.
40. Rozière J., Jones D.J., Marrony M., Glipa X., Mula B. On the doping of sulfonated polybenzimidazole with strong bases. Solid State Ionics 2001, 145:61-68.
41. Jouanneau J., Mercier R., Gonon L., Gebel G. Synthesis of sulfonated polybenzimidazoles from functionalized monomers. Macromolecules 2007, 40:983-990.
42. Zhang F., Li N., Cui Z., Zhang S., Li S. Novel acid-base polyimides synthesized from binaphthalene dianhydride and triphenylamine-containing diamine as proton exchange membranes. J. Membr. Sci. 2008, 314:24-32.
43. Hickman B.S., Mascal M., Titman J.J., Wood I.G. Protonic conduction in imidazole-a solid-state NMR study. J. Am. Chem. Soc. 1999, 121:11486-11490.
44. Park H.B., Lee C.H., Sohn J.Y., Lee Y.M., Freeman B.D., Kim H.J. Effect of crosslinked chain length in sulfonated polyimide membranes. J. Membr. Sci. 2006, 285:432-439.
45. Li W., Bellay Y.Z., Fu Y.Z., Manthiram A. N,N-bis-(1H-benzimidazol-2-yl)-isophthalamide as an additive in sulfonated polymer membranes for direct methanol fuel cells. J. Power Sources 2008, 180:719-723.
46. Colomban P., Novak A. Proton Conductors 1992, 38-55. Cambridge University Press, Cambridge, UK. P. Colomban (Ed.).
47. Ponce M.L., Boaventura M., Gomes D., Mendes A., Madeira L.M. Proton conducting membranes based on benzimidazole sulfonic acid doped sulfonated (poly)oxadiazole-triazole copolymer for low humidity operation. Fuel Cells 2008, 3/4:209-216.
48. Gomes D., Roeder J., Ponce M.L., Nunes S.P. Single-step synthesis of sulfonated polyoxadiazoles and their use as proton conducting membranes. J. Power Sources 2008, 175:49-59.
49. Yasuda T., Li Y., Miyatake K., Hirai M., Nanasawa M., Watanabe M. Synthesis and properties of polyimides bearing acid groups on long pendant aliphatic chains. J. Polym. Sci. Part A: Polym. Chem. 2006, 44:3995-4005.
50. Ding F.C., Wang S.J., Xiao M., Meng Y.Z. Crosslinked sulfonated poly(phathalazinone ether ketone)s for PEM fuel cell application as proton exchange membrane. J. Power Sources 2007, 164:488-495.
51. Oh Y.S., Lee H.J., Yoo M., Kim H.J., Han J., Kim K., Hong J.D., Kim T.H. Azide-assisted crosslinked sulfonated poly(ether sulfone)s as stable and highly conductive membranes. Chem. Commun. 2008, 2028-2029.
52. Guo X., Fang J., Watari T., Tanaka K., Kita H., Okamato K. Macromolecules 2002, 35:6707-6713.
53. Chen Y., Meng Y., Hay A. Novel synthesis of sulfonated poly(phthalazinone ether ketone) used as a proton exchange membrane. Macromolecules 2005, 38:3556-3564.
54. Ding F.C., Wang S.J., Xiao M., Li X.H., Meng Y.Z. Crosslinked sulfonated fluorine-containing poly(arylene ether ketone) for proton exchange membrane. J. Power Sources 2007, 170:20-27.
55. Wu S., Qiu Z., Zhang S., Yang X., Yang F., Li Z. The direct synthesis of wholly aromatic poly(p-phenylene)s bearing sulfobenzoyl side groups as proton exchange membranes. Polymer 2006, 47:6993-7000.
56. Lee C.H., Park C.H., Lee Y.M. Sulfonated polyimide membranes grafted with sulfoalkylated side chains for proton exchange membrane. J. Membr. Sci. 2008, 313:199-206.
57. Shahi V.K. Sulfonated poly(ether sulfone)-silica polyelectrolyte composite membranes for fuel cells. Solid State Ionics 2007, 177:3395-3404.
58. Liu B., Robertson G.P., Kim D.S., Guiver M.D., Hu W., Jiang Z. Aromatic poly(ether ketone)s with pendant sulfonic acid phynyl groups. Macromolecules 2007, 40:1934-1944.