Synthesis and properties of soluble sulfonated polybenzimidazoles derived from asymmetric dicarboxylic acid monomers with sulfonate group as proton exchange membrane

Journal of Membrane Science

Volumn 369, Issue 1-2, 2011, Pages 388-396

  Wang, Gang ^a   Xiao, Guyu ^a   Yan, Deyue ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

Polybenzimidazole; Proton exchange membrane; Soluble; Sulfonated

Indexed keywords

ACID BASE INTERACTION; DICARBOXYLIC ACID; HIGH THERMAL; ION EXCHANGE CAPACITY; NAPHTHALENE DICARBOXYLIC ACIDS; OXIDATIVE STABILITY; POLYBENZIMIDAZOLE; POLYMER CHAINS; PROMISING MATERIALS; PROTON EXCHANGE MEMBRANE; PROTON EXCHANGE MEMBRANES; SOLUBLE; SULFONATE GROUPS; SULFONATED; SULFONATED MONOMERS; WATER UPTAKE;

MECHANICAL PROPERTIES; MEMBRANES; MONOMERS; NAPHTHALENE; POLYCONDENSATION; PROTON CONDUCTIVITY; PROTON EXCHANGE MEMBRANE FUEL CELLS (PEMFC); CHAINS;

ION EXCHANGE; MONOMERS;

6 SULFONATE 1,4 NAPHTHALENE DICARBOXYLIC ACID; 6,8 DISULFONATE 1,4 NAPHTHALENE DICARBOXYLIC ACID; BENZIMIDAZOLE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; MONOMER; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; DICARBOXYLIC ACID; PROTON;

ARTICLE; ARTIFICIAL MEMBRANE; ELECTRIC CONDUCTIVITY; ION EXCHANGE; MEMBRANE STABILIZATION; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON EXCHANGE MEMBRANE; PROTON TRANSPORT; SULFONATION; SYNTHESIS; THERMOSTABILITY; CONTROLLED STUDY; ION CONDUCTANCE; SOLUBILITY; WATER TRANSPORT;

EID: 79251619778     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.memsci.2010.12.028     Document Type: Article

References (55)

1. Hickner M.A., Ghassemi H., Kim Y.S., Einsla B.R., McGrath J.E. Alternative polymer systems for proton exchange membranes (PEMs). Chem. Rev. 2004, 104:4587-4612.
2. 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.
3. Kerres J.A. Development of ionomer membranes for fuel cells. J. Membr. Sci. 2001, 185:3-27.
4. Jones D.J., Rozière J. Non-fluorinated polymer materials for proton exchange membrane fuel cells. Annu. Rev. Mater. Res. 2003, 33:503-555.
5. Kreuer K.D. On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells. J. Membr. Sci. 2001, 185:29-39.
6. 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.
7. Wu D., Xu T.W., Wu L., Wu Y.H. Hybrid acid-base polymer membranes prepared for application in fuel cells. J. Power Sources 2009, 186:286-292.
8. Ueda M., Toyota H., Ochi T., Sugiyama J., Yonetake K., Masuko T., Teramoto T. Synthesis and characterization of aromatic poly(ether sulfone)s containing pendant sodium sulfonate groups. J. Polym. Sci.: Polym. Chem. 1993, 31:853-858.
9. Wang F., Hickner M., Kim Y.S., Zawodzinski T.A., McGrath J.E. Direct polymerization of sulfonated poly(arylene ether sulfone) random (statistical) copolymers: candidates for new proton exchange membranes. J. Membr. Sci. 2002, 197:231-242.
10. Zhang Y., Wan Y., Zhang G., Shao K., Zhao C.J., Li H.T., Na H. Preparation and properties of novel cross-linked sulfonated poly(arylene ether ketone) for direct methanol fuel cell application. J. Membr. Sci. 2010, 348:353-359.
11. Yang Y., Siu A., Peckham T.J., Holdcroft S. Structural and morphological features of acid-bearing polymers for PEM fuel cells. Adv. Polym. Sci. 2008, 216:55-126.
12. 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.
13. Xiao G.Y., Sun G.M., Yan D.Y. Sulfonated poly(thioether ketone)s with high oxidation resistance to peroxides. Abstr. Pap. Am. Chem. Soc. 2003, 225:U558-U1558.
14. Ma X.H., Shen L.P., Zhang C.J., Xiao G.Y., Yan D.Y., Sun G.M. Sulfonated poly(arylene thioether phosphine oxide)s copolymers for proton exchange membrane fuel cells. J. Membr. Sci. 2008, 310:303-311.
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. Matsumura S., Hlil A.R., Lepiller C., Gaudet J., Guay D., Hay A.S. Ionomers for proton exchange membrane fuel cells with sulfonic acid groups on the end groups: novel linear aromatic poly(sulfide-ketone)s. Macromolecules 2008, 41:277-280.
17. Marestin C., Gebel G., Diat O., Mercier R. Sulfonated polyimides. Adv. Polym. Sci. 2008, 216:185-258.
18. 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.
19. 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.: Polym. Chem. 2008, 46:2820-2832.
20. Chen K.C., Hu Z.X., Endo N., Fang J.H., Higa M., Okamoto K.-I. Sulfonated polyimides bearing benzimidazole groups for direct methanol fuel cell applications. J. Membr. Sci. 2010, 351:214-221.
21. Xiao G.Y., Sun G.M., Yan D.Y., Zhu P.F., Tao P. Synthesis of sulfonated poly(phthalazinone ether sulfone)s by direct polymerization. Polymer 2002, 43:5335-5339.
22. Zhu X.L., Liang Y.F., Pan H.Y., Jian X.G., Zhang Y.X. Synthesis and properties of novel H-bonded composite membranes from sulfonated poly(phthalazinone ether)s for PEMFC. J. Membr. Sci. 2008, 312:59-65.
23. Gao Y., Robertson G.P., Guiver M.D., Wang G., Jian X., Mikhailenko S.D., Li X., Kaliaguine S. Sulfonated copoly(phthalazinone ether ketone nitrile)s as proton exchange membrane materials. J. Membr. Sci. 2006, 278:26-34.
24. Allcock H.R., Wood R.M. Design and synthesis of ion-conductive polyphosphazenes for fuel cell applications. J. Polym. Sci.: Polym. Phys. 2006, 44:2358-2368.
25. Wycisk R., Pintauro P.N. Polyphosphazene membranes for fuel cells. Adv. Polym. Sci. 2008, 216:157-183.
26. Uno K., Niume K., Iwata Y., Toda F., Iwakura Y. Synthesis of polybenzimidazoles with sulfonic acid groups. J. Polym. Sci.: Polym. Chem. 1977, 15:1309-1318.
27. Asensio J.A., Borros S., Gómez-Romero P. Proton-conducting polymers based on benzimidazoles and sulfonated benzimidazoles. J. Polym. Sci.: Polym. Chem. 2002, 40:3703-3710.
28. 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.
29. 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.
30. Peron J., Ruiz E., Jones D.J., Rozière J. Solution sulfonation of a novel polybenzimidazole a proton electrolyte for fuel cell application. J. Membr. Sci. 2008, 314:247-256.
31. Tan N., Xiao G.Y., Yan D.Y. Soluble sulfonated polybenzothiazoles: a new candidate for proton exchange membrane. Chem. Mater. 2010, 22:1022-1031.
32. Han M.M., Zhang G., Shao K., Li H.T., Zhang Y., Li M.Y., Wang S., Na H. Carboxyl-terminated benzimidazole-assisted cross-linked sulfonated poly(ether ether ketone)s for highly conductive PEM with low water uptake and methanol permeability. J. Mater. Chem. 2010, 20:3246-3252.
33. Jannasch P. Membrane materials by chemical grafting of aromatic main-chain polymers. Fuel Cells 2005, 5:248-260.
34. Lee J.K., Kerres J. Synthesis and characterization of sulfonated poly(arylene thioether)s and their blends with polybenzimidazole for proton exchange membranes. J. Membr. Sci. 2007, 294:75-83.
35. Tan N., Chen Y., Xiao G.Y., Yan D.Y. Synthesis and properties of sulfonated polybenzothiazoles with benzimidazole moieties as proton exchange membranes. J. Membr. Sci. 2010, 356:70-77.
36. Feng S.G., Shang Y.M., Wang S.B., Xie X.F., Wang Y.Z., Wang Y.W., Xu J.M. Novel method for the preparation of ionically crosslinked sulfonated poly(arylene ether sulfone)/polybenzimidazole composite membranes via in situ polymerization. J. Membr. Sci. 2010, 346:105-112.
37. Wainright J.S., Wang J.T., Weng D., Savinell R.F., Litt M. Acid-doped polybenzimidazoles: a new polymer electrolyte. J. Electrochem. Soc. 1995, 142:L121-123.
38. Wang J.-T., Wainright J.S., Savinell R.F., Litt M. A direct methanol fuel cell using acid-doped polybenzimidazole as polymer electrolyte. J. Appl. Electrochem. 1996, 26:751-756.
39. Jones D.J., Rozière J. Recent advances in the functionalisation of polybenzimidazole and polyetherketone for fuel cell applications. J. Membr. Sci. 2001, 185:41-58.
40. 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.
41. Asensio J.A., Sánchez E.M., Gómez-Romero P. Proton-conducting membranes based on benzimidazole polymers for high-temperature PEM fuel cells. A chemical quest. Chem. Soc. Rev. 2010, 39:3210-3239.
42. Kerres J., Tang C.-M., Graf C. Improvement of properties of poly(ether ketone) ionomer membranes by blending and cross-linking. Ind. Eng. Chem. Res. 2004, 43:4571-4579.
43. Bae J.M., Honma I., Murata M., Yamamoto T., Rikukawa M., Ogata N. Properties of selected sulfonated polymers as proton-conducting electrolytes for polymer electrolyte fuel cells. Solid State Ionics 2002, 147:189-194.
44. 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.
45. Tan N., Xiao G.Y., Yan D.Y., Sun G.M. Preparation and properties of polybenzimidazoles with sulfophenylsulfonyl pendant groups for proton exchange membranes. J. Membr. Sci. 2010, 353:51-59.
46. Jouanneau J., Gonon L., Gebel G., Martin V., Mercier R. Synthesis and characterization of ionic conducting sulfonated polybenzimidazoles. J. Polym. Sci.: Polym. Chem. 2010, 48:1732-1742.
47. 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.: Polym. Chem. 2005, 43:4363-4372.
48. Qing S.B., Huang W., Yan D.Y. Synthesis and properties of soluble sulfonated polybenzimidazoles. React. Funct. Polym. 2006, 66:219-227.
49. Qing S.B., Huang W., Yan D.Y. Synthesis and characterization of thermally stable sulfonated polybenzimidazoles. Chem. J. Chinese U. 2005, 26:2145-2148.
50. Q.Y. Wu, G.Y. Xiao, D.Y. Yan, Synthesis of soluble sulfonated polybenzimidazoles derived from 2-sulfonate terephthalic acid, e-Polymers (2008) no. 073.
51. 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.
52. Musto P., Karasz F.E., MacKnight W.J. Fourier transform infrared spectroscopy on the thermooxidative degradation of polybenzimidazole and of a polybenzimiidazole/polyetherimide blend. Polymer 1993, 34:2934-2945.
53. Bai Z.W., Price G.E., Yoonessi M., Juhl S.B., Durstock M.F., Dang T.D. Proton exchange membranes based on sulfonated polyarylenethioethersulfone and sulfonated polybenzimidazole for fuel cell applications. J. Membr. Sci. 2007, 305:69-76.
54. Krishnan N.N., Lee H.-J., Kim H.-J., Kim J.-Y., Hwang I., Jang J.H., Cho E.A., Kim S.-K., Henkensmeier D., Hong S.-A., Lim T.-H. Sulfonated poly(ether sulfone)/sulfonated polybenzimidazole blend membrane for fuel cell applications. Eur. Polym. J. 2010, 46:1633-1641.
55. Nasef M.M., Saidi H., Nor H.M., Foo O.M. Cation exchange membranes by radiation-induced graft copolymerization of styrene onto PFA copolymer films. II. Charactarization of sulfonated graft copolymer membranes. J. Appl. Polym. Sci. 2000, 76:1-11.