Synthesis and properties of sulfonated polybenzothiazoles with benzimidazole moieties as proton exchange membranes

Journal of Membrane Science

Volumn 356, Issue 1-2, 2010, Pages 70-77

  Tan, Ning ^a   Chen, Yan ^a   Xiao, Guyu ^a   Yan, Deyue ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Benzimidazole; Polybenzothiazole; Proton exchange membrane; Sulfonated

Indexed keywords

BENZIMIDAZOLES; COMPARISON STUDY; ELONGATION AT BREAK; HIGH THERMAL; OVERALL PROPERTIES; OXIDATIVE STABILITY; PROTON EXCHANGE MEMBRANES; RIGID RODS; SULFONATION DEGREE; THERMAL PROPERTIES; YOUNG'S MODULUS;

DIMENSIONAL STABILITY; HYDROGEN BONDS; IONIC STRENGTH; IONIZATION OF LIQUIDS; IONOMERS; MECHANICAL PROPERTIES; ORGANIC SOLVENTS; OXIDATION RESISTANCE; POLYCONDENSATION; PROTON CONDUCTIVITY; PROTON EXCHANGE MEMBRANE FUEL CELLS (PEMFC); SOLUBILITY; SYNTHESIS (CHEMICAL); TENSILE STRENGTH; THERMODYNAMIC PROPERTIES;

MEMBRANES;

BENZIMIDAZOLE; BENZOTHIAZOLE DERIVATIVE; HYDROGEN; ORGANIC SOLVENT; POLYMER; PROTON; SULFUR; WATER;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CROSS LINKING; ENERGY RESOURCE; HYDROGEN BOND; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON EXCHANGE MEMBRANE FUEL CELL; PROTON SODIUM EXCHANGE; SOLUBILITY; SULFONATION; SYNTHESIS; TEMPERATURE; TENSILE STRENGTH; THERMOSTABILITY; YOUNG MODULUS;

EID: 77952281108     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.memsci.2010.03.028     Document Type: Article

References (56)

1. Hickner M.A., Ghassemi H., Kim Y.S., Einsla B.R., McGrath J.E. Alternative polymer systems for proton exchange membranes. Chem. Rev. 2004, 104:4587-4612.
2. Rikukawa M., Sanui K. Proton-conducting polymer electrolyte membranes based on hydrocarbon polymers. Prog. Polym. Sci. 2000, 25:1463-1502.
3. Kerres J.A. Development of ionomer membranes for fuel cells. J. Membr. Sci. 2001, 185:3-27.
4. Kreuer K.D. On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells. J. Membr. Sci. 2001, 185:29-39.
5. Li Q.F., He R.H., Jensen J.O., Bjerrum N.J. Approaches and recent development of polymer electrolyte membranes for fuel cells operating above 100°C. Chem. Mater. 2003, 15:4896-4915.
6. Jones D.J., Rozière J. Non-fluorinated polymer materials for proton exchange membrane fuel cell. Annu. Rev. Mater. Res. 2003, 33:503-555.
7. Savadogo O. Emerging membranes for electrochemical systems: part II. High temperature composite membranes for polymer electrolyte fuel cell (PEFC) applications. J. Power Sources 2004, 127:135-161.
8. Gürsel S.A., Gubler L., Gupta B., Scherer G.G. Radiation grafted membranes. Adv. Polym. Sci. 2008, 215:157-217.
9. Li L.F., Deng B., Ji Y.L., Yu Y., Xie L.D., Li J.Y., Lu X.F. A novel approach to prepare proton exchange membranes from fluoropolymer powder by pre-irradiation induced graft polymerization. J. Membr. Sci. 2010, 346:113-120.
10. Jing L.W., Liu B.J., Guan S.W., Jiang Z.H. Synthesis of fluorinated poly(arylene ether)s bearing a sulfonic acid group on a pendant group. Chem. J. Chinese Univ. 2008, 29:1074-1076.
11. Ding J.F., Chuy C., Holdcroft S. Enhanced conductivity in morphologically controlled proton exchange membranes: synthesis of macromonomers by SFRP and their incorporation into graft polymers. Macromolecules 2002, 35:1348-1355.
12. Ma X.H., Zhang C.J., Xiao G.Y., Yan D.Y., Sun G.M. Synthesis and properties of sulfonated poly(arylene ether phosphine oxide)s for proton exchange membranes. J. Power Sources 2009, 188:57-63.
13. Chikashige Y., Chikyu Y., Miyatake K., Watanabe M. Poly(arylene ether) ionomers containing sulfofluorenyl groups for fuel cell applications. Macromolecules 2005, 38:7121-7126.
14. Nakabayashi K., Matsumoto K., Ueda M. Synthesis and properties of sulfonated multiblock copoly(ether sulfone)s by a chain extender. J. Polym. Sci. Part A: Polym. Chem. 2008, 46:3947-3957.
15. Bai Z.W., Dang T.D. Direct synthesis of fully sulfonated polyarylenethioether sulfones as proton-conducting polymers for fuel cells. Macromol. Rapid Commun. 2006, 27:1271-1277.
16. Zhang W., Gogel V., Friedrich K.A., Kerres J. Novel covalently cross-linked poly(etheretherketone) ionomer membranes. J. Power Sources 2006, 155:3-12.
17. Marestin C., Gebel G., Diat O., Mercier R. Sulfonated polyimides. Adv. Polym. Sci. 2008, 216:185-258.
18. Allcock H.R., Wood R.M. Design and synthesis of ion-conductive polyphosphazenes for fuel cell applications. J. Polym. Sci. Part B: Polym. Phys. 2006, 44:2358-2368.
19. Mader J., Xiao L.X., Schmidt T.J., Benicewicz B.C. Polybenzimidazole/acid complexes as high-temperature membranes. Adv. Polym. Sci. 2008, 216:63-124.
20. Staiti P., Lufrano F., Arico A.S., Passalacqua E., Antonucci V. Sulfonated polybenzimidazole membranes-preparation and physico-chemical characterization. J. Membr. Sci. 2001, 188:71-78.
21. Jannasch P. Fuel cell membrane materials by chemical grafting of aromatic main-chain polymers. Fuel Cells 2005, 5:248-260.
22. Yang H.H. Aromatic High-strength Fibers 1989, Wiley, New York.
23. Hu X.D., Jenkins S.E., Min B.G., Polk M.B., Kumar S. Rigid-rod polymers synthesis processing simulation structure and properties. Macromol. Mater. Eng. 2003, 288:823-843.
24. So Y.H. Rigid rod polymers with enhanced lateral interactions. Prog. Polym. Sci. 2000, 25:137-157.
25. Park S.-Y., Koerner H., Putthanarat S., Ozisik R., Juhl S., Farmer B.L., Eby R.K. Structure of poly(p-phenylenebenzobisoxazole) (PBZO) and poly(p-phenylenebenzobisthiazole) (PBZT) for proton exchange membranes (PEMs) in fuel cells. Polymer 2004, 45:49-59.
26. Reynolds J.R., Lee Y., Kim S., Bartling R.L., Gieselman M.B., Savage C.S. Rigid-rod and high aspect ratio aromatic polyelectrolytes based on polybenzimidazoles and polybenzothiazoles. Polym. Prep. 1993, 34:1065-1066.
27. Kim S., Cameron D.A., Lee Y., Reynolds J.R., Savage C.R. Aromatic and rigid rod polyelectrolytes based on sulfonated poly(benzobisthiazoles). J. Polym. Sci. Part A: Polym. Chem. 1996, 34:481-492.
28. Dang T.D., Koerner H., Dalton M.J., Iacobucci A.M., Venkatasubramanian N., Arnold F.E. Sulfo-pendant poly(p-phenylenebenzobisazole) rigid-rods: synthesis and fiber structural studies. Polym. Prep. 2003, 44:927-928.
29. Tan N., Xiao G.Y., Yan D.Y. Sulfonated polybenzothiazoles: a novel candidate for proton exchange membranes. Chem. Mater. 2010, 22:1022-1031.
30. Li N.W., Cui Z.M., Zhang S.B. Sulfonated polyimides bearing benzimidazole groups for proton exchange membranes. Polymer 2007, 48:7255-7263.
31. Lin H.D., Zhao C.J., Cui Z.M., Ma W.J., Fu T.Z., Na H., Xing W. Novel sulfonated poly(arylene ether ketone) copolymers bearing carboxylic or benzimidazole pendant groups for proton exchange membranes. J. Power Sources 2009, 193:507-514.
32. Zhang G.M., Guo X.X., Fang J.H., Chen K.C., Okamoto K.I. Preparation and properties of covalently cross-linked sulfonated copolyimide membranes containing benzimidazole groups. J. Membr. Sci. 2009, 326:708-713.
33. Hong Y.T., Lee C.H., Park H.S., Min K.A., Kim H.J., Nam S.Y., Lee Y.M. Improvement of electrochemical performances of sulfonated poly(arylene ether sulfone) via incorporation of sulfonated poly(arylene ether benzimidazole). J. Power Sources 2008, 175:724-731.
34. Álvarez-Gallego Y., Ruffmann B., Silva V., Silva H., Lozano A.E., Campa J.G., Nunes S.P., Abajo J. Sulfonated polynaphthalimides with benzimidazole pendant groups. Polymer 2008, 49:3875-3883.
35. Qi Y.H., Gao Y., Tian S.H., Hlil A.R., Gaudet J., Guay D., Hay A.S. Synthesis and properties of novel benzimidazole-containing sulfonated polyethersulfones for fuel cell applications. J. Polym. Sci. Part A: Polym. Chem. 2009, 47:1920-1929.
36. Wang J., Song Y., Zhang C., Ye Z., Liu H., Lee M.H., Wang D., Ji J. Alternating copolymer of sulfonated poly(ether ether ketone-benzimidazole)s (SPEEK-BI) bearing acid and base moieties. Macromol. Chem. Phys. 2008, 209:1495-1502.
37. Zhang Y., Shao K., Zhao C.J., Zhang G., Li H.T., Fu T.Z., Na H. Novel sulfonated poly(ether ether ketone) with pendant benzimidazole groups as a proton exchange membrane for direct methanol fuel cells. J. Power Sources 2009, 194:175-181.
38. Qing S.B., Huang W., Yan D.Y. Synthesis and characterization of thermally stable sulfonated polybenzimidazoles obtained from 3,3′-disulfonyl-4,4′-dicarboxyldiphenylsulfone. J. Polym. Sci. Part A: Polym. Chem. 2005, 43:4363-4372.
39. Choi J., Lee K.M., Wycisk R., Pintauro P.N., Mather P.T. Nanofiber network ion-exchange membranes. Macromolecules 2008, 41:4569-4572.
40. Li W.M., Cui Z.M., Zhou X.C., Zhang S.B., Dai L., Xing W. Sulfonated poly(arylene-co-imide)s as water stable proton exchange membrane materials for fuel cells. J. Membr. Sci. 2008, 315:172-179.
41. Kang S., Zhang C.J., Xiao G.Y., Yan D.Y., Sun G.M. Synthesis and properties of soluble sulfonated polybenzimidazoles from 3,3′-disulfonate-4,4′-dicarboxylbiphenyl as proton exchange membranes. J. Membr. Sci. 2009, 334:91-100.
42. Wu Q.Y., Xiao G.Y., Yan D.Y. Synthesis of soluble sulfonated polybenzimidazoles derived from 2-sulfonate terephthalic acid. e-Polymers 2008, no. 073.
43. Osaheni J.A., Jenekhe S.A. Synthesis and processing of heterocyclic polymers as electronic, optoelectronic, and nonlinear optical materials. 1. New conjugated rigid-rod benzobisthiazole polymers. Chem. Mater. 1992, 4:1282-1290.
44. Osaheni J.A., Jenekhe S.A. Fourier transform infra-red spectroscopy on the thermo-oxidative degradation of polybenzimidazole and of a polybenzimidazole/polyetherimide blend. Macromolecules 1995, 28:1172-1179.
45. Shen D.Y., Hsu S.L. Vibrational spectroscopic characterization of rigid rod polymers: 3. Microstructural changes in stressed polymers. Polymer 1982, 23:969-973.
46. Musto P., Karasz F.E., MacKnight W.J. Fourier transform infra-red spectroscopy on the thermo-oxidative degradation of polybenzimidazole and of a polybenzimidazole/polyetherimide blend. Polymer 1993, 34:2934-2945.
47. Saito J., Miyatake K., Watanabe M. Synthesis and properties of polyimide ionomers containing 1H-1,2,4-triazole groups. Macromolecules 2008, 41:2415-2420.
48. Li N.W., Cui Z.M., Zhang S.B., Li S.H. 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.
49. Jouanneau J., Mercier R., Gonon L., Gebel G. Synthesis of sulfonated polybenzimidazoles from functionalized monomers: preparation of ionic conducting membranes. Macromolecules 2007, 40:983-990.
50. Bai H., Ho W.S.W. New carbon dioxide-selective membranes based on sulfonated polybenzimidazole (SPBI) copolymer matrix for fuel cell applications. Ind. Eng. Chem. Res. 2009, 48:2344-2354.
51. Glipa X., Bonnet B., Mula B., Jones D.J., Rozière J. Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole. J. Mater. Chem. 1999, 9:3045-3049.
52. Tian S.H., Meng Y.Z., Hay A.S. Membranes from poly(aryl ether)-based ionomers containing randomly distributed nanoclusters of 6 or 12 sulfonic acid groups. Macromolecules 2009, 42:1153-1160.
53. 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, 128:1762-1769.
54. Xing P.X., Robertson G.P., Guiver M.D., Mikhailenko S.D., Kaliaguine S. Sulfonated poly(aryl ether ketone)s containing the hexafluoroisopropylidene diphenyl moiety prepared by direct copolymerization, as proton exchange membranes for fuel cell application. Macromolecules 2004, 37:7960-7967.
55. Liu B.J., Robertson G.P., Kim D.S., Guiver M.D., Hu W., Jiang Z.H. Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules 2007, 40:1934-1944.
56. Miyatake K., Zhou H., Watanabe M. Sulfonated poly(aryl ether ketone)s containing the hexafluoroisopropylidene diphenyl moiety prepared by direct copolymerization, as proton exchange membranes for fuel cell application. Macromolecules 2004, 37:4956-4960.