Thermal crosslinking of aromatic polyethers bearing pyridine groups for use as high temperature polymer electrolytes

Journal of Membrane Science

Volumn 415-416, Issue , 2012, Pages 42-50

  Kalamaras, Ioannis ^a,b   Daletou, Maria K ^a   Neophytides, Stylianos G ^a   Kallitsis, Joannis K ^a,b  

^a INSTITUTE OF CHEMICAL ENGINEERING SCIENCES   (Greece)

^b UNIVERSITY OF PATRAS   (Greece)

Author keywords

Cell performance; High temperature PEMFC; Membrane properties; Proton exchange membrane; Thermal crosslinking

Indexed keywords

CELL PERFORMANCE; HIGH TEMPERATURE; MEMBRANE PROPERTIES; PROTON EXCHANGE MEMBRANES; THERMAL CROSSLINKING;

AROMATIC COMPOUNDS; CHEMICAL BONDS; COPOLYMERS; ETHERS; GLASS TRANSITION; MECHANICAL PROPERTIES; PHOSPHORIC ACID; POLYELECTROLYTES; POLYETHERS; PROTON EXCHANGE MEMBRANE FUEL CELLS (PEMFC); PYRIDINE; SEMICONDUCTOR DOPING; SYNTHESIS (CHEMICAL);

CROSSLINKING;

COPOLYMER; CROSS LINKING REAGENT; ELECTROLYTE; GLASS; PHOSPHORIC ACID; POLYETHER DERIVATIVE; POLYMER; PYRIDINE DERIVATIVE;

AROMATIZATION; ARTICLE; ARTIFICIAL MEMBRANE; CHEMICAL ANALYSIS; CONTROLLED STUDY; CROSS LINKING; ENERGY RESOURCE; FILM; GLASS TRANSITION TEMPERATURE; HIGH TEMPERATURE; MEMBRANE CONDUCTANCE; MOLECULAR MECHANICS; MOLECULAR WEIGHT; OXIDATION; PHYSICAL CHEMISTRY; POLARIZATION; POLYMER ELECTROLYTE MEMBRANE FUEL CELL; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS; THERMOSTABILITY;

EID: 84864743465     PISSN: 03767388     EISSN: 18733123     Source Type: Journal    
DOI: 10.1016/j.memsci.2012.04.057     Document Type: Article

References (74)

1. Dresselhaus M.S., Thomas I.L. Alternative energy technologies. Nature 2001, 414:332-337.
2. Costamagna P., Srinivasan S. Quantum jumps in the PEMFC science and technology from the 1960s to the year 2000: Part I. Fundamental scientific aspects. J. Power Sources 2001, 102:242-252.
3. Li Q., Jensen J.O., Savinell R.F., Bjerrum N.J. High temperature proton exchange membranes based on polybenzimidazoles for fuel cells. J. Prog. Polym. Sci. 2009, 34:449-477.
4. Zhang J., Xie Z., Zhang J., Tang Y., Song C., Navessin T., Shi Z., Song D., Wang H., Wilkinson D.P., Liu Z.S., Holdcroft S. High temperature PEM fuel cells. J. Power Sources 2006, 160:872-891.
5. Rikukawa M., Sanui K. Proton conducting polymer electrolyte membranes based on hydrocarbon polymers. Prog. Polym. Sci. 2000, 25:1463-1502.
6. Kerres A. Development of ionomer membranes for fuel cells. J. Membr. Sci. 2001, 185:3-27.
7. Aharoni S.M., Litt M.H. Synthesis and some properties of poly-(2,5-trimethylene benzimidazole) and poly-(2,5-trimethylene benzimidazole hydrochloride). J. Polym. Sci. Part A: Polym. Chem. 1974, 12:639-650.
8. Savinell R.F., Yeager E., Tryk D., Landau U., Wainright J., Weng D., Lux K., Litt M., Rogers C. A polymer electrolyte for operation at temperatures up to 200°C. J. Electrochem. Soc. 1994, 141:L46-L48.
9. Wainright J.S., Wang J.T., Weng D., Savinell R.F., Litt M.J. Acid-doped polybenzimidazoles: a new polymer electrolyte. J. Electrochem. Soc. 1995, 142:L121-L123.
10. Ma Y.L., Wainright J.S., Litt M.H., Savinell R.F. Conductivity of PBI membranes for high-temperature polymer electrolyte fuel cells. J. Electrochem. Soc. 2004, 151:A8-A16.
11. Bouchet R., Siebert E. Proton conduction in acid doped polybenzimidazole. Solid State Ionics 1999, 118:287-299.
12. 2 fuel cell using acid doped polybenzimidazole as polymer electrolyte. Electrochim. Acta 1996, 41:193-197.
13. Kawahara M., Morita J., Rikukawa M., Sanui K., Ogata N. Synthesis and proton conductivity of thermally stable polymer electrolyte: poly(benzimidazole) complexes with strong acid molecules. Electrochim. Acta 2000, 45:1395-1398.
14. Xiao L., Zhang H., Scanlon E., Ramanathan L.S., Choe E.-W., Rogers D., Apple T., Benicewicz B.C. High-temperature polybenzimidazole fuel cell membranes via a sol-gel process. Chem. Mater. 2005, 17:5328-5333.
15. 4 high-temperature PEMFC. Int. J. Hydrogen Energy 2006, 31:1855-1862.
16. Vogel H., Marvel C.S. Polybenzimidazoles, new thermally stable polymers. J. Polym. Sci. 1961, 50:511-539.
17. Li Q., He R., Jensen J.O., Bjerrum N.J. PBI-based polymer membranes for high temperature fuel cells-preparation, characterization and fuel cell demonstration. Fuel Cells 2004, 4:147-159.
18. 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.
19. Xiao L., Zhang H., Jana T., Scanlon E., Chen R., Choe E.-W., Ramanathan L.S., Yu S., Benicewicz B.C. Synthesis and characterization of pyridine-based polybenzimidazoles for high temperature polymer electrolyte membrane fuel cell applications. Fuel Cells 2005, 5:287-295.
20. 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.
21. Pefkianakis E.K., Deimede V., Daletou M.K., Gourdoupi N., Kallitsis J.K. Novel polymer electrolyte membrane, based on pyridine containing poly(ether sulfone), for application in high-temperature fuel cells. Macromol. Rapid Commun. 2005, 26:1724-1728.
22. Daletou M.K., Gourdoupi N., Kallitsis J.K. Proton conducting membranes based on blends of PBI with aromatic polyethers containing pyridine units. J. Membr. Sci. 2005, 252:115-122.
23. Geormezi M., Deimede V., Gourdoupi N., Triantafyllopoulos N., Neophytides S., Kallitsis J.K. Novel pyridine-based poly(ether sulfones) and their study in high temperature PEM fuel cells. Macromolecules 2008, 41:9051-9056.
24. Daletou M.K., Geormezi M., Pefkianakis E.K., Morfopoulou C., Kallitsis J.K. Fully aromatic copolyethers for high temperature polymer electrolyte membrane fuel cells. Fuel Cells 2010, 10:35-44.
25. N. Gourdoupi, N. Triantafyllopoulos, V. Deimede, L. Pefkianakis, M. Daletou, S. Neophytides, J. Kallitsis, US Patent, WO/2008/038162, 2008.
26. Morfopoulou C., Andreopoulou A.K., Kallitsis J.K. The effect of structural variations on aromatic polyethers for high-temperature PEM fuel cells. J. Polym. Sci. Part A: Polym. Chem. 2011, 49:4325-4334.
27. 4 imbibed electrolyte based on PBI/polysulfone copolymer blends. J. Membr. Sci. 2009, 326:76-83.
28. Kalamaras I., Daletou M.K., Gregoriou V.G., Kallitsis J.K. Sulfonated aromatic polyethers containing pyridine units as electrolytes for high temperature fuel cells. Fuel Cells 2011, 11:921-931.
29. Gourdoupi N., Andreopoulou A.K., Deimede V., Kallitsis J.K. Novel proton-conducting polyelectrolyte composed of an aromatic polyether containing main-chain pyridine units for fuel cell applications. Chem. Mater. 2003, 15:5044-5050.
30. Geormezi M., Chochos C., Gourdoupi N., Neophytides S.G., Kallitsis J.K. High performance polymer electrolytes based on main and side chain pyridine aromatic polyethers for high and medium temperature proton exchange membrane fuel cells. J. Power Sources 2011, 196:9382-9390.
31. Avgouropoulos G., Papavasiliou J., Daletou M.K., Kallitsis J.K., Ioannides T., Neophytides S. Reforming methanol to electricity in a high temperature PEM fuel cell. Appl. Catal. B: Environ. 2009, 90:628-632.
32. Schmittinger W., Vahidi A. A review of the main parameters influencing long-term performance and durability of PEM fuel cells. J. Power Sources 2008, 180:1-14.
33. Kerres J.A. Blended and cross-linked ionomer membranes for application in membrane fuel cells. Fuel Cells 2005, 5:230-247.
34. Hasiotis C., Deimede V., Kontoyannis C.G. New polymer electrolytes based on blends of sulfonated polysulfones with polybenzimidazole. Electrochim. Acta 2001, 46:2401-2406.
35. Geormezi M., Gourdoupi N., Daletou M.K., Neophytides S., Kallitsis J.K. New polymer electrolyte membrane based on sulfonated polysulfone blends. CI&CEQ 2003, 1:137-142.
36. + ion transport properties of sulfonated poly(2,6-dimethyl-1,4-phenyleneoxide) membranes. J. Electrochem. Soc. 2003, 150:E329-E336.
37. Kosmala B., Schauer J. Ion-exchange membranes prepared by blending sulfonated poly(2,6-dimethyl-1,4-phenylene oxide) with polybenzimidazole. J. Appl. Polym. Sci. 2002, 85:1118-1127.
38. Jörissen L., Gogel V., Kerres J., Garche J. New membranes for direct methanol fuel cells. J. Power Sources 2002, 105:267-273.
39. Kerres J., Hein M., Zhang W., Graf S., Nicoloso N. Development of new blend membranes for polymer electrolyte fuel cell applications. J. New Mater. Electrochem. Syst. 2003, 6:223-230.
40. Hobson L.J., Nakano Y., Ozu H., Hayase S. Targeting improved DMFC performance. J. Power Sources 2002, 104:79-84.
41. 4/Nafion-PBI composite membrane for enhanced durability of high temperature PEM fuel cells. J. Power Sources 2007, 169:259-264.
42. 4. Part I. Synthesis and characterisation of polymers and binary blend membranes. Fuel Cells 2008, 8:175-187.
43. 4. Part II. Characterisation and fuel cell tests of the ternary membranes. Fuel Cells 2008, 8:188-199.
44. Feng S., Shang Y., Xie X., Wang Y., Xu J. Synthesis and characterization of crosslinked sulfonated poly(arylene ether sulfone) membranes for DMFC applications. J. Membr. Sci. 2009, 335:13-20.
45. Ding F.C., Wang S.J., Xiao M., Li X.H., Meng Y.Z. Fabrication and properties of cross-linked sulfonated fluorene-containing poly(arylene ether ketone) for proton exchange membrane. J. Power Sources 2007, 170:20-27.
46. Zhong S., Fu T., Dou Z., Zhao C., Na H. Preparation and evaluation of a proton exchange membrane based on crosslinkable sulfonated poly(ether ether ketone)s. J. Power Sources 2006, 162:51-57.
47. Oh Y.-S., Lee H.-J., Yoo M., Kim H.-J., Han J., Kim T.-H. Synthesis of novel crosslinked sulfonated poly(ether sulfone)s using bisazide and their properties for fuel cell application. J. Membr. Sci. 2008, 323:309-315.
48. Ding F.C., Wang S.J., Xiao M., Meng Y.Z. Cross-linked sulfonated poly(phathalazinone ether ketone)s for PEM fuel cell application as proton-exchange membrane. J Power Sources 2007, 164:488-495.
49. 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.
50. Zhong S., Liu C., Na H. Preparation and properties of UV irradiation-induced crosslinked sulfonated poly(ether ether ketone) proton exchange membranes. J. Membr. Sci. 2009, 326:400-407.
51. Jeong M.-H., Lee K.-S., Lee J.-S. Cross-linking density effect of fluorinated aromatic polyethers on transport properties. Macromolecules 2009, 42:1652-1658.
52. Lee K.S., Jeong M.H., Lee J.S., Pivovar B.S., Kim Y.S. Optimizing end-group cross-linkable polymer electrolytes for fuel cell applications. J. Membr. Sci. 2010, 352:180-188.
53. Lee K.-S., Jeong M.-H., Lee J.-P., Lee J.-S. End-group cross-linked poly(arylene ether) for proton exchange membranes. Macromolecules 2009, 42:584-590.
54. Wang K.Y., Xiao Y., Chung T.-S. Chemically modified polybenzimidazole nanofiltration membrane for the separation of electrolytes and cephalexin. Chem. Eng. Sci. 2006, 61:5807-5817.
55. Li Q., Pan C., Jensen J.O., Noyé P., Bjerrum N.J. Cross-linked polybenzimidazole membranes for fuel cells. Chem. Mater. 2007, 19:350-352.
56. Noyé P., Li Q., Pan C., Bjerrum N.J. Cross-linked polybenzimidazole membranes for high temperature proton exchange membrane fuel cells with dichloromethyl phosphinic acid as a cross-linker. Polym. Adv. Technol. 2008, 19:1270-1275.
57. Xu N., Guo X., Fang J., Xu H., Yin J. Synthesis of novel polybenzimidazoles with pendant amino groups and the formation of their crosslinked membranes for medium temperature fuel cell applications. J. Polym. Sci. Part A: Polym. Chem. 2009, 47:6992-7002.
58. Bhadra S., Kim N.H., Lee J.H. A new self-cross-linked, net-structured, proton conducting polymer membrane for high temperature proton exchange membrane fuel cells. J. Membr. Sci. 2010, 349:304-311.
59. Guan Y.S., Pu H.T., Jin M., Chang Z.H., Wan D.C. Preparation and characterisation of proton exchange membranes based on crosslinked polybenzimidazole and phosphoric acid. Fuel Cells 2010, 10:973-982.
60. Papadimitriou K.D., Paloukis F., Neophytides S.G., Kallitsis J.K. Cross-linking of side chain unsaturated aromatic polyethers for high temperature polymer electrolyte membrane fuel cell applications. Macromolecules 2011, 44:4942-4951.
61. Dondoni A., Ghiglione C., Marra A., Scoponi M. Synthesis of calix[4]arenylvinylene and calix[4]arenylphenylene oligomers by stille and suzuki cross-coupling reactions. J. Org. Chem. 1998, 63:9535-9539.
62. Li N., Shin D.W., Hwang D.S., Lee Y.M., Guiver M.D. Polymer electrolyte membranes derived from new sulfone monomers with pendent sulfonic acid groups. Macromolecules 2010, 43:9810-9820.
63. radical initiated degradation reactions of sulfonated aromatics as model compounds for fuel cell proton conducting membranes. Mater. Chem. 1999, 9:409-418.
64. Hibsham C., Cornelius C.J., Marand E. The gas separation effects of annealing polyimide-organosilicate hybrid membranes. J. Membr. Sci. 2003, 211:25-40.
65. Wind J.D., Bickel C.S., Paul R.D., Koros W.J. Solid-state covalent cross-linking of polyimide membranes for carbon dioxide plasticization reduction. Macromolecules 2003, 36:1882-1888.
66. Braks J.G., Huang R.Y.M. Polymerization mechanisms and molecular weight distribution. II. AIBN-initiated polymerization of styrene at 60°C. J. Appl. Polym. Sci. 1978, 22:3111-3120.
67. Pryor W.A., Coco J.H. Computer simulation of the polymerization of styrene. The mechanism of thermal initiation and the importance of primary radical termination. Macromolecules 1970, 3:500-508.
68. Vöge A., Deimede V.A., Kallitsis J.K. Side chain crosslinking of aromatic polyethers for high temperature polymer electrolyte membrane fuel cell applications. J. Polym. Sci. Part A: Polym. Chem. 2012, 50:207-216.
69. Gourdoupi N., Kallitsis J.K., Neophytides S. New proton conducting polymer blends and their fuel cell performance. J. Power Sources 2010, 195:170-174.
70. Bosnjakovic A., Schlick S. Nafion perfluorinated membranes treated in Fenton media: radical species detected by ESR spectroscopy. J. Phys. Chem. B 2004, 108:4332-4337.
71. Zhang Y., Wan Y., Zhang G., Shao K., Zhao C., Li H., 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.
72. Kongstein O.E., Berning T., Børresen B., Seland F., Tunold R. Polymer electrolyte fuel cells based on phosphoric acid doped polybenzimidazole (PBI) membranes. Energy 2007, 32:418-422.
73. Li Q., Hjuler H.A., Bjerrum N.J. Phosphoric acid doped polybenzimidazole membranes: physiochemical characterization and fuel cell applications. J. Appl. Electrochem. 2001, 31:773-779.
74. Yu S., Xiao L., Benicewicz B.C. Durability studies of PBI-based high temperature PEMFCs. Fuel Cells 2008, 8:165-174.