Synthesis and characterization of sulfonated poly(arylene ether ketone) copolymers containing crosslinking moiety

Journal of Membrane Science

Volumn 337, Issue 1-2, 2009, Pages 145-152

  Jeong, Myung Hwan ^a   Lee, Kwan Soo ^a   Lee, Jae Suk ^a  

^a Gwangju Institute of Science and Technology (GIST)   (South Korea)

Author keywords

Crosslinked membrane; Crosslinking; Fuel cell; Proton conductivity; Proton exchange membrane

Indexed keywords

BIPHENOL; COVALENT BONDING; CROSS LINKED MEMBRANES; CROSS-LINKABLE; CROSSLINKED MEMBRANE; DECOMPOSITION TEMPERATURE; DIHYDROXYNAPHTHALENE; DIPHENOL; FTIR-ATR SPECTRA; GLASS TRANSITION TEMPERATURE; HEXAFLUOROISOPROPYLIDENE; ION EXCHANGE CAPACITY; MEMBRANE PROPERTIES; NETWORK STRUCTURES; POLY(ARYLENE ETHER KETONE); PROTON EXCHANGE MEMBRANE; STEP-GROWTH POLYMERIZATIONS; SYNTHESIS AND CHARACTERIZATION; THERMAL CURING; WATER UPTAKE;

CELL MEMBRANES; COPOLYMERIZATION; COPOLYMERS; DEIONIZED WATER; DIELECTRIC RELAXATION; DIFFERENTIAL SCANNING CALORIMETRY; ELECTROCHEMISTRY; ETHERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FUEL CELLS; GLASS TRANSITION; ION EXCHANGE; KETONES; PLASTIC PRODUCTS; PROTON CONDUCTIVITY; SYNTHESIS (CHEMICAL);

ION EXCHANGE MEMBRANES;

2,8 DIHYDROXYNAPHTHALENE 6 SULFONATED SALT; 4,4' (HEXAFLUOROISOPROPYLIDENE)DIPHENOL; 4,4' DIFLUOROBENZOPHENONE; 4,4' DIHYDROXYBIPHENYL; COPOLYMER; PHENOL DERIVATIVE; SODIUM CHLORIDE; SULFONATED POLY(ARYLENE ETHER KETONE) COPOLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CROSS LINKING; DIFFERENTIAL SCANNING CALORIMETRY; ION EXCHANGE; MEMBRANE; MOLECULAR WEIGHT; POLYMERIZATION; PRIORITY JOURNAL; SULFONATION; SYNTHESIS; TEMPERATURE; THERMOSTABILITY; WATER TRANSPORT;

EID: 67349261432     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.memsci.2009.03.035     Document Type: Article

References (39)

1. Grot W.G. Perfluorinated ion exchange polymers and their use in research and industry. Macromol. Symp. 82 (1994) 161
2. Kreuer K.D. On the development of proton conducting polymer membranes for hydrogen and methanol fuel cells. J. Membr. Sci. 185 (2001) 29
3. Motupally S., Becker A.J., and Weidner J.W. Diffusion of water in Nafion 115 membranes. J. Electrochem. Soc. 147 9 (2000) 3171
4. Rikukawa M., and Sanui K. Proton conducting polymer electrolyte membranes based on hydrocarbon polymers. Prog. Polym. Sci. 25 (2000) 1463
5. Xing P., Robertson G.P., Guiver M.D., Mikhailenko S.D., Wang K., and Kaliaguine S. Synthesis and characterization of sulfonated poly(ether ether ketone) for proton exchange membranes. J. Membr. Sci. 229 (2004) 95
6. Nakabayashi K., Matsumoto K., Shibasaki Y., and Ueda M. Synthesis and properties of sulfonated poly(2,5-diphenethoxy-p-phenylene). Polymer 48 (2007) 5878
7. Wang F., Hickner M., Kim Y.S., Zawodzinski T.A., and McGrath J.E. Direct polymerization of sulfonated poly(arylene ether sulfone) random (statistical) copolymers: candidates for new proton exchange membranes. J. Membr. Sci. 197 (2002) 231
8. Glipa X., Haddad M.E., Jones D.J., and Roziere J. Synthesis and characterization of sulfonated polybenzimidazole: a highly conducting proton exchange polymer. Solid State Ionics 97 (1997) 323
9. Kim H.J., Litt M.H., Shin E.M., and Nam S.Y. Hydrolytic stability of sulfonic acid-containing polyimides for fuel cell membranes. Macromol. Res. 12 (2004) 545
10. Vallejo E., Pourcelly G., Gavach C., Mercier R., and Pineri M. Sulfonated polyimide as proton conductor exchange membranes, physicochemical properties and separating H+/Mz+ by electrodialysis comparison with perfluorosulfonic membranes. J. Membr. Sci. 160 (1999) 127
11. Kim Y.S., Hickner M., Dong L., Pivovara B.S., and McGrath J.E. Sulfonated poly(arylene ether sulfone) copolymer proton exchange membranes: composition and morphology effects on the methanol permeability. J. Membr. Sci. 243 (2004) 317
12. Mauritz K.A. Organic-inorganic hybrid materials: perfluorinated ionomers as sol-gel polymerization templates for inorganic alkoxides. Mater. Sci. Eng. C 6 (1998) 121
13. Kim D.S., Liu B., and Guiver M.D. Influence of silica content in sulfonated poly(arylene ether ether ketone ketone) (SPAEEKK) hybrid membranes on properties for fuel cell application. Polymer 47 (2006) 7871
14. Yin Y., Hayashi S., Yamada O., Kita H., and Okamoto K. Branched/crosslinked sulfonated polyimide membranes for polymer electrolyte fuel cells. Macromol. Rapid Commun. 26 (2005) 696
15. Kerres J., Ullrich A., Meier F., and Häring Th. Synthesis and characterization of novel acid-base polymer blends for the application in membrane fuel cells. Solid State Ionics 125 (1999) 243
16. Kerres J. Blended and cross-linked ionomer membranes for application in membrane fuel cells. Fuel Cells 5 (2005) 230
17. Guiver M.D., Robertson G.P., and Foley S. Chemical modification of polysulfones. II. An efficient method for introducing primary amine groups onto the aromatic chain. Macromolecules 28 (1995) 7612
18. Zhong S., Cui X., Cai H., Fu T., Zhao C., and Na H. Crosslinked sulfonated poly(ether ether ketone) proton exchange membranes for direct methanol fuel cell applications. J. Power Sources 164 (2007) 65
19. Kice J.L., and Puls A.R. The reaction of hypochlorite with various oxidized derivatives of disulfides and with sulfinate ions. J. Am. Chem. Soc. 99 (1977) 3455
20. Kerres J., Cui W., and Junginger M. Development and characterization of cross-linked ionomer membranes based upon sulfinated and sulfonated PSU. 2. Cross-linked PSU blend membranes by alkylation of sulfinate groups with dihalogenoalkanes. J. Membr. Sci. 139 (1998) 227
21. Guo Q., Pintauro P.N., Tang H., and O'Connor S. Sulfonated and crosslinked polyphosphazene based polymer electrolyte membranes. J. Membr. Sci. 154 (1999) 175
22. Rhim J.-W., Park H.B., Lee C.-S., Jun J.-H., Kim D.S., and Lee Y.M. Crosslinked poly(vinyl alcohol) membranes containing sulfonic acid group: proton and methanol transport through membranes. J. Membr. Sci. 238 (2004) 143
23. Lee C.H., Park H.B., Chung Y.S., Lee Y.M., and Freeman B.D. Water sorption, proton conduction, and methanol permeation properties of sulfonated polyimide membranes cross-linked with N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES). Macromolecules 39 (2006) 755
24. Ding F.C., Wang S.J., Xiao M., and Meng Y.Z. Cross-linked sulfonated poly(phathalazinone ether ketone)s for PEM fuel cell application as proton-exchange membrane. J. Power Sources 164 (2007) 488
25. Miyatake K., Oyaizu K., Tsuchida E., and Hay A.S. Synthesis and properties of novel sulfonated arylene ether/fluorinated alkane copolymers. Macromolecules 34 (2001) 2065
26. Liu B., Robertson G.P., Kim D.S., Guiver M.D., Hu W., and Jiang Z. Aromatic poly(ether ketone)s with pendant sulfonic acid phenyl groups prepared by a mild sulfonation method for proton exchange membranes. Macromolecules 40 (2007) 1934
27. Lafitte B., Karlsson L.E., and Jannasch P. Sulfophenylation of polysulfones for proton-conducting fuel cell membranes. Macromol. Rapid Commun. 23 (2002) 896
28. Lafitte B., Puchner M., and Jannasch P. Proton conducting polysulfone ionomers carrying sulfoaryloxybenzoyl side chains. Macromol. Rapid Commun. 26 (2005) 1464
29. Wang L., Meng Y.Z., Li X.H., Xiao M., Wang S.J., and Hay A.S. Oxidatively stable and highly proton conductive membrane from poly(arylene ether)s containing biphenyl moiety as pendent groups. J. Membr. Sci. 280 (2006) 108
30. Gao Y., Robertson G.P., Guiver M.D., Mikhailenko S.D., Li X., and Kaliaguine S. 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
31. Lee H.-J., Lee M.-H., Oh M.-C., Ahn J.-H., and Han S.G. Crosslinkable polymers for optical waveguide devices. II. Fluorinated ether ketone oligomers bearing ethynyl group at the chain end. J. Polym. Sci., Part A: Polym. Chem. 37 (1999) 2355
32. Lee K.-S., and Lee J.-S. Synthesis of highly fluorinated poly(arylene ether sulfide) for polymeric optical waveguides. Chem. Mater. 18 (2006) 4519
33. Kim J.-P., Lee W.-Y., Kang J.-W., Kwon S.-K., Kim J.-J., and Lee J.-S. Fluorinated poly(arylene ether sulfide) for polymeric optical waveguide devices. Macromolecules 34 (2001) 7817
34. Lee K.-S., Jeong M.-H., Lee J.-P., and Lee J.-S. End-group crosslinked poly(arylene ether) membrane for fuel cell applications. Macromolecules 42 (2009) 584
35. Saaby S., Baxendale I.R., and Ley S.V. Non-metal-catalysed intramolecular alkyne cyclotrimerization reactions promoted by focussed microwave heating in batch and flow modes. Org. Biomol. Chem. 3 (2005) 3365
36. Saito S., and Yamamoto Y. Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives. Chem. Rev. 100 (2000) 2901
37. Jeong M.-H., Lee K.-S., Hong Y.-T., and Lee J.-S. Selective and quantitative sulfonation of poly(arylene ether ketone)s containing pendant phenyl rings by chlorosulfonic acid. J. Membr. Sci. 314 (2008) 212
38. Mauritz K.A., and Moore R.B. State of understanding of Nafion. Chem. Rev. 104 (2004) 4535
39. McLean R.S., Doyle M., and Sauer B.B. High-resolution imaging of ionic domains and crystal morphology in ionomers using AFM techniques. Macromolecules 33 (2000) 6541