Skip to main content

2016 | OriginalPaper | Buchkapitel

7. Synthesis of Polybenzimidazoles

verfasst von : Jingshuai Yang, Ronghuan He, David Aili

Erschienen in: High Temperature Polymer Electrolyte Membrane Fuel Cells

Verlag: Springer International Publishing

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Recent progress in the synthesis of polybenzimidazole (PBI) derivatives is summarized for application as high temperature polymer electrolyte membrane in fuel cells. Various designs in the polymer structure are described aiming at improvement of the membrane performance. The ways to produce PBI derivatives containing different functional groups, segments, or blocks of other macromolecules are classified as main-chain modification, copolymerization, and side-chain grafting. The synthetic routes and associated characterization methods particularly with respect to the polymer structures are also addressed.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Vogel T, Marvel CS (1961) Polybenzimidazoles, new thermally stable polymers. J Polym Sci 50:511–539CrossRef Vogel T, Marvel CS (1961) Polybenzimidazoles, new thermally stable polymers. J Polym Sci 50:511–539CrossRef
2.
Zurück zum Zitat Neuse EW (1982) Aromatic polybenzimidazoles—syntheses, properties and applications. Adv Polym Sci 47:1–42CrossRef Neuse EW (1982) Aromatic polybenzimidazoles—syntheses, properties and applications. Adv Polym Sci 47:1–42CrossRef
3.
Zurück zum Zitat Chung TS (1997) A critical review of polybenzimidazoles: historical development and future R&D. J Macromol Sci C 37:277–301 Chung TS (1997) A critical review of polybenzimidazoles: historical development and future R&D. J Macromol Sci C 37:277–301
4.
Zurück zum Zitat Weber J (2010) Nanostructured poly(benzimidazole): from mesoporous networks to nanofibers. ChemSusChem 3:181–187CrossRef Weber J (2010) Nanostructured poly(benzimidazole): from mesoporous networks to nanofibers. ChemSusChem 3:181–187CrossRef
5.
Zurück zum Zitat Kumbharkar SC, Karadkar PB, Kharul UK (2006) Enhancement of gas permeation properties of polybenzimidazoles by systematic structure architecture. J Membr Sci 286:161–169CrossRef Kumbharkar SC, Karadkar PB, Kharul UK (2006) Enhancement of gas permeation properties of polybenzimidazoles by systematic structure architecture. J Membr Sci 286:161–169CrossRef
6.
Zurück zum Zitat Wang KY, Chung TS (2006) Fabrication of polybenzimidazole (PBI) nanofiltration hollow fiber membranes for removal of chromate. J Membr Sci 281:307–315CrossRef Wang KY, Chung TS (2006) Fabrication of polybenzimidazole (PBI) nanofiltration hollow fiber membranes for removal of chromate. J Membr Sci 281:307–315CrossRef
7.
Zurück zum Zitat Yang T, Xiao Y, Chung TS (2011) Poly-/metal-benzimidazole nano-composite membranes for hydrogen purification. Energy Environ Sci 4:4171–4180CrossRef Yang T, Xiao Y, Chung TS (2011) Poly-/metal-benzimidazole nano-composite membranes for hydrogen purification. Energy Environ Sci 4:4171–4180CrossRef
8.
Zurück zum Zitat Han YJ, Wang KH, Lai JY et al (2014) Hydrophilic chitosan-modified polybenzoimidazole membranes for pervaporation dehydration of isopropanol aqueous solutions. J Membr Sci 463:17–23CrossRef Han YJ, Wang KH, Lai JY et al (2014) Hydrophilic chitosan-modified polybenzoimidazole membranes for pervaporation dehydration of isopropanol aqueous solutions. J Membr Sci 463:17–23CrossRef
9.
Zurück zum Zitat Li Q, Jensen JO, Savinell RF et al (2009) High temperature proton exchange membranes based on polybenzimidazoles for fuel cells. Prog Polym Sci 34:449–477CrossRef Li Q, Jensen JO, Savinell RF et al (2009) High temperature proton exchange membranes based on polybenzimidazoles for fuel cells. Prog Polym Sci 34:449–477CrossRef
10.
Zurück zum Zitat Asensio JA, Sánchez EM, Gómez-Romero P (2010) Proton-conducting membranes based on benzimidazole polymers for high-temperature PEM fuel cells. A chemical quest. Chem Soc Rev 39:3210–3239CrossRef Asensio JA, Sánchez EM, Gómez-Romero P (2010) Proton-conducting membranes based on benzimidazole polymers for high-temperature PEM fuel cells. A chemical quest. Chem Soc Rev 39:3210–3239CrossRef
11.
Zurück zum Zitat Quartarone E, Mustarelli P (2012) Polymer fuel cells based on polybenzimidazole/H3PO4. Energy Environ Sci 5:6436–6444CrossRef Quartarone E, Mustarelli P (2012) Polymer fuel cells based on polybenzimidazole/H3PO4. Energy Environ Sci 5:6436–6444CrossRef
12.
Zurück zum Zitat Ma YL, Wainright JS, Litt MH et al (2004) Conductivity of PBI membranes for high-temperature polymer electrolyte fuel cells. J Electrochem Soc 151:A8–A16CrossRef Ma YL, Wainright JS, Litt MH et al (2004) Conductivity of PBI membranes for high-temperature polymer electrolyte fuel cells. J Electrochem Soc 151:A8–A16CrossRef
13.
Zurück zum Zitat Vilčiauskas L, Tuckerman M, Bester G et al (2012) The mechanism of proton conduction in phosphoric acid. Nat Chem 4:461–466CrossRef Vilčiauskas L, Tuckerman M, Bester G et al (2012) The mechanism of proton conduction in phosphoric acid. Nat Chem 4:461–466CrossRef
14.
Zurück zum Zitat Wainright JS, Wang JT, Weng D et al (1995) Acid-doped polybenzimidazoles—a new polymer electrolyte. J Electrochem Soc 142:L121–L123CrossRef Wainright JS, Wang JT, Weng D et al (1995) Acid-doped polybenzimidazoles—a new polymer electrolyte. J Electrochem Soc 142:L121–L123CrossRef
15.
Zurück zum Zitat He R, Li Q, Xiao G et al (2003) Proton conductivity of phosphoric acid doped polybenzimidazole and its composites with inorganic proton conductors. J Membr Sci 226:169–184CrossRef He R, Li Q, Xiao G et al (2003) Proton conductivity of phosphoric acid doped polybenzimidazole and its composites with inorganic proton conductors. J Membr Sci 226:169–184CrossRef
16.
Zurück zum Zitat Yang JS, He RH (2010) Preparation and characterization of polybenzimidazole membranes prepared by gelation in phosphoric acid. Polym Adv Technol 21:874–880MathSciNetCrossRef Yang JS, He RH (2010) Preparation and characterization of polybenzimidazole membranes prepared by gelation in phosphoric acid. Polym Adv Technol 21:874–880MathSciNetCrossRef
17.
Zurück zum Zitat He R, Li Q, Bach A et al (2006) Physicochemical properties of phosphoric acid doped polybenzimidazole membranes for fuel cells. J Membr Sci 277:38–45CrossRef He R, Li Q, Bach A et al (2006) Physicochemical properties of phosphoric acid doped polybenzimidazole membranes for fuel cells. J Membr Sci 277:38–45CrossRef
18.
Zurück zum Zitat Lobato J, Cañizares P, Rodrigo MA et al (2007) Improved polybenzimidazole films for H3PO4-doped PBI-based high temperature PEMFC. J Membr Sci 306:47–55CrossRef Lobato J, Cañizares P, Rodrigo MA et al (2007) Improved polybenzimidazole films for H3PO4-doped PBI-based high temperature PEMFC. J Membr Sci 306:47–55CrossRef
19.
Zurück zum Zitat Samms SR, Wasmus S, Savinell RF (1996) Thermal stability of proton conducting acid doped polybenzimidazole in simulated fuel cell environments. J Electrochem Soc 143:1225–1232CrossRef Samms SR, Wasmus S, Savinell RF (1996) Thermal stability of proton conducting acid doped polybenzimidazole in simulated fuel cell environments. J Electrochem Soc 143:1225–1232CrossRef
20.
Zurück zum Zitat Li Q, He RH, Gao J et al (2003) The CO poisoning effect in PEMFCs operational at temperatures up to 200 °C. J Electrochem Soc 150:A1599–A1605CrossRef Li Q, He RH, Gao J et al (2003) The CO poisoning effect in PEMFCs operational at temperatures up to 200 °C. J Electrochem Soc 150:A1599–A1605CrossRef
21.
Zurück zum Zitat Wang JT, Savinell RF, Wainright JS et al (1996) A H2/O2 fuel cell using acid doped polybenzimidazole as polymer electrolyte. Electrochim Acta 41:193–197CrossRef Wang JT, Savinell RF, Wainright JS et al (1996) A H2/O2 fuel cell using acid doped polybenzimidazole as polymer electrolyte. Electrochim Acta 41:193–197CrossRef
22.
Zurück zum Zitat Jensen JO, Li Q, He R et al (2005) 100–200 °C polymer fuel cells for use with NaAlH4. J Alloy Compd 404–406:653–656CrossRef Jensen JO, Li Q, He R et al (2005) 100–200 °C polymer fuel cells for use with NaAlH4. J Alloy Compd 404–406:653–656CrossRef
23.
Zurück zum Zitat Jensen JO, Li Q, Pan C et al (2007) High temperature PEMFC and the possible utilization of the excess heat for fuel processing. Int J Hydrogen Energy 32:1567–1571CrossRef Jensen JO, Li Q, Pan C et al (2007) High temperature PEMFC and the possible utilization of the excess heat for fuel processing. Int J Hydrogen Energy 32:1567–1571CrossRef
24.
Zurück zum Zitat Pan C, He R, Li Q et al (2005) Integration of high temperature PEM fuel cells with a methanol reformer. J Power Sources 145:392–398CrossRef Pan C, He R, Li Q et al (2005) Integration of high temperature PEM fuel cells with a methanol reformer. J Power Sources 145:392–398CrossRef
25.
Zurück zum Zitat Vogel H, Marvel CS (1963) Polybenzimidazoles. II. J Polym Sci A 1:1531–1541 Vogel H, Marvel CS (1963) Polybenzimidazoles. II. J Polym Sci A 1:1531–1541
26.
Zurück zum Zitat Choe EW (1982) Single-stage melt polymerization process for the production of high molecular weight polybenzimidazole. US Patent 4,312,976 Choe EW (1982) Single-stage melt polymerization process for the production of high molecular weight polybenzimidazole. US Patent 4,312,976
27.
Zurück zum Zitat Choe EW (1994) Catalysts for the preparation of polybenzimidazoles. J Appl Polym Sci 53:497–506CrossRef Choe EW (1994) Catalysts for the preparation of polybenzimidazoles. J Appl Polym Sci 53:497–506CrossRef
28.
Zurück zum Zitat Choe EW, Choe DD (1996) Polybenzimidazoles (overview). In: Salamone JC (ed) Polymeric materials encyclopedia, vol 7. CRC, New York, pp 5619–5638 Choe EW, Choe DD (1996) Polybenzimidazoles (overview). In: Salamone JC (ed) Polymeric materials encyclopedia, vol 7. CRC, New York, pp 5619–5638
29.
Zurück zum Zitat Wang S, Zhang G, Han M et al (2011) Novel epoxy-based cross-linked polybenzimidazole for high temperature proton exchange membrane fuel cells. Int J Hydrogen Energy 36:8412–8421CrossRef Wang S, Zhang G, Han M et al (2011) Novel epoxy-based cross-linked polybenzimidazole for high temperature proton exchange membrane fuel cells. Int J Hydrogen Energy 36:8412–8421CrossRef
30.
Zurück zum Zitat Iwakura Y, Imai Y, Uno K (1964) Polyphenylenebenzimidazoles. J Polym Sci A 2:2605–2615 Iwakura Y, Imai Y, Uno K (1964) Polyphenylenebenzimidazoles. J Polym Sci A 2:2605–2615
31.
Zurück zum Zitat Eaton PE, Carlson GR, Lee JT (1973) Phosphorus pentoxide–methanesulphonic acid. Convenient alternative to polyphosphoric acid. J Org Chem 38:4071–4073CrossRef Eaton PE, Carlson GR, Lee JT (1973) Phosphorus pentoxide–methanesulphonic acid. Convenient alternative to polyphosphoric acid. J Org Chem 38:4071–4073CrossRef
32.
Zurück zum Zitat Kim HJ, Cho SY, An SJ et al (2004) Synthesis of poly(2,5-benzimidazole) for use as a fuel-cell membrane. Macromol Rapid Commun 25:894–897CrossRef Kim HJ, Cho SY, An SJ et al (2004) Synthesis of poly(2,5-benzimidazole) for use as a fuel-cell membrane. Macromol Rapid Commun 25:894–897CrossRef
33.
Zurück zum Zitat Jouanneau J, Mercier R, Gonon L et al (2007) Synthesis of sulphonated polybenzimidazoles from functionalized monomers: preparation of ionic conducting membranes. Macromolecules 40:983–990CrossRef Jouanneau J, Mercier R, Gonon L et al (2007) Synthesis of sulphonated polybenzimidazoles from functionalized monomers: preparation of ionic conducting membranes. Macromolecules 40:983–990CrossRef
34.
Zurück zum Zitat Hedberg FL, Marvel CS (1974) A new single-step process for polybenzimidazole synthesis. J Polym Sci 12:1823–1828 Hedberg FL, Marvel CS (1974) A new single-step process for polybenzimidazole synthesis. J Polym Sci 12:1823–1828
35.
Zurück zum Zitat Yang JS, Cleemann LN, Steenberg T et al (2014) High molecular weight polybenzimidazole membranes for high temperature PEMFC. Fuel Cells 14:7–15CrossRef Yang JS, Cleemann LN, Steenberg T et al (2014) High molecular weight polybenzimidazole membranes for high temperature PEMFC. Fuel Cells 14:7–15CrossRef
36.
Zurück zum Zitat Li Q, Rudbeck HC, Chromik A et al (2010) Properties, degradation and high temperature fuel cell test of different types of PBI and PBI blend membranes. J Membr Sci 347:260–270CrossRef Li Q, Rudbeck HC, Chromik A et al (2010) Properties, degradation and high temperature fuel cell test of different types of PBI and PBI blend membranes. J Membr Sci 347:260–270CrossRef
37.
Zurück zum Zitat Sannigrahi A, Ghosh S, Lalnuntluanga J et al (2009) How the monomer concentration of polymerization influences various properties of polybenzimidazole: a case study with poly(4,4′-diphenylether-5,5′-bibenzimidazole). J Appl Polym Sci 111:2194–2203CrossRef Sannigrahi A, Ghosh S, Lalnuntluanga J et al (2009) How the monomer concentration of polymerization influences various properties of polybenzimidazole: a case study with poly(4,4′-diphenylether-5,5′-bibenzimidazole). J Appl Polym Sci 111:2194–2203CrossRef
38.
Zurück zum Zitat Yang J, Li Q, Cleemann LN et al (2012) Synthesis and properties of poly(aryl sulfone benzimidazole) and its copolymers for high temperature membrane electrolytes for fuel cells. J Mater Chem 22:11185–11195CrossRef Yang J, Li Q, Cleemann LN et al (2012) Synthesis and properties of poly(aryl sulfone benzimidazole) and its copolymers for high temperature membrane electrolytes for fuel cells. J Mater Chem 22:11185–11195CrossRef
39.
Zurück zum Zitat Kim TH, Lim TW, Lee JC (2007) High-temperature fuel cell membranes based on mechanically stable para-ordered polybenzimidazole prepared by direct casting. J Power Sources 172:172–179CrossRef Kim TH, Lim TW, Lee JC (2007) High-temperature fuel cell membranes based on mechanically stable para-ordered polybenzimidazole prepared by direct casting. J Power Sources 172:172–179CrossRef
40.
Zurück zum Zitat Sannigrahi A, Arunbabu D, Sankar RM et al (2007) Tuning the molecular properties of polybenzimidazole by copolymerization. J Phys Chem B 111:12124–12132CrossRef Sannigrahi A, Arunbabu D, Sankar RM et al (2007) Tuning the molecular properties of polybenzimidazole by copolymerization. J Phys Chem B 111:12124–12132CrossRef
41.
Zurück zum Zitat Kim TH, Kim SK, Lim TW et al (2008) Synthesis and properties of poly(aryl ether benzimidazole) copolymers for high-temperature fuel cell membranes. J Membr Sci 323:362–370CrossRef Kim TH, Kim SK, Lim TW et al (2008) Synthesis and properties of poly(aryl ether benzimidazole) copolymers for high-temperature fuel cell membranes. J Membr Sci 323:362–370CrossRef
42.
Zurück zum Zitat Qian GQ, Benicewicz BC (2009) Synthesis and characterization of high molecular weight hexafluoroisopropylidene-containing polybenzimidazole for high-temperature polymer electrolyte membrane fuel cells. J Polym Sci A 47:4064–4073CrossRef Qian GQ, Benicewicz BC (2009) Synthesis and characterization of high molecular weight hexafluoroisopropylidene-containing polybenzimidazole for high-temperature polymer electrolyte membrane fuel cells. J Polym Sci A 47:4064–4073CrossRef
43.
Zurück zum Zitat Yang J, He R, Che Q et al (2010) A copolymer of poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] and poly(2,5-benzimidazole) for high-temperature proton-conducting membranes. Polym Int 59:1695–1700CrossRef Yang J, He R, Che Q et al (2010) A copolymer of poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] and poly(2,5-benzimidazole) for high-temperature proton-conducting membranes. Polym Int 59:1695–1700CrossRef
44.
Zurück zum Zitat Steenberg T, Hjuler HA, Terkelsen C et al (2012) Roll-to-roll coated PBI membranes for high temperature PEM fuel cells. Energy Environ Sci 5:6076–6080CrossRef Steenberg T, Hjuler HA, Terkelsen C et al (2012) Roll-to-roll coated PBI membranes for high temperature PEM fuel cells. Energy Environ Sci 5:6076–6080CrossRef
45.
Zurück zum Zitat Lobato J, Cañizares P, Rodrigo MA et al (2006) Synthesis and characterisation of poly[2,2-(m-phenylene)-5,5-bibenzimidazole] as polymer electrolyte membrane for high temperature PEMFCs. J Membr Sci 280:351–362CrossRef Lobato J, Cañizares P, Rodrigo MA et al (2006) Synthesis and characterisation of poly[2,2-(m-phenylene)-5,5-bibenzimidazole] as polymer electrolyte membrane for high temperature PEMFCs. J Membr Sci 280:351–362CrossRef
46.
Zurück zum Zitat Nüchter M, Ondruschka B, Bonrath W et al (2004) Microwave assisted synthesis—a critical technology overview. Green Chem 6:128–141CrossRef Nüchter M, Ondruschka B, Bonrath W et al (2004) Microwave assisted synthesis—a critical technology overview. Green Chem 6:128–141CrossRef
47.
Zurück zum Zitat Singh V, Kumari PL, Tiwariy A et al (2007) Alumina supported synthesis of cassia marginata gum-g-poly(acrylonitrile) under microwave irradiation. Polym Adv Technol 18:379–385CrossRef Singh V, Kumari PL, Tiwariy A et al (2007) Alumina supported synthesis of cassia marginata gum-g-poly(acrylonitrile) under microwave irradiation. Polym Adv Technol 18:379–385CrossRef
48.
Zurück zum Zitat Hoogenboom R, Schubert US (2007) Microwave-assisted polymer synthesis: recent developments in a rapidly expanding field of research. Macromol Rapid Commun 28:368–386CrossRef Hoogenboom R, Schubert US (2007) Microwave-assisted polymer synthesis: recent developments in a rapidly expanding field of research. Macromol Rapid Commun 28:368–386CrossRef
49.
Zurück zum Zitat He R, Sun B, Yang J et al (2009) Synthesis of poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] and poly(2,5-benzimidazole) by microwave irradiation. Chem Res Chinese Universities 25:585–589 He R, Sun B, Yang J et al (2009) Synthesis of poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] and poly(2,5-benzimidazole) by microwave irradiation. Chem Res Chinese Universities 25:585–589
50.
Zurück zum Zitat Kuwahara N (1963) On the polymer-solvent interaction in polymer solutions. J Polym Sci A 1:2395–2406 Kuwahara N (1963) On the polymer-solvent interaction in polymer solutions. J Polym Sci A 1:2395–2406
51.
Zurück zum Zitat Shroff RN (1965) Single-point determination of intrinsic viscosity. J Appl Polym Sci 9:1547–1551CrossRef Shroff RN (1965) Single-point determination of intrinsic viscosity. J Appl Polym Sci 9:1547–1551CrossRef
52.
Zurück zum Zitat Liao J, Li Q, Rudbeck HC et al (2011) Oxidative degradation of polybenzimidazole membranes as electrolytes for high temperature proton exchange membrane fuel cells. Fuel Cells 11:745–755CrossRef Liao J, Li Q, Rudbeck HC et al (2011) Oxidative degradation of polybenzimidazole membranes as electrolytes for high temperature proton exchange membrane fuel cells. Fuel Cells 11:745–755CrossRef
53.
Zurück zum Zitat Yuan YX, Johnson F, Cabasso I (2009) Polybenzimidazole (PBI) molecular weight and Mark-Houwink equation. J Appl Polym Sci 112:3436–3441CrossRef Yuan YX, Johnson F, Cabasso I (2009) Polybenzimidazole (PBI) molecular weight and Mark-Houwink equation. J Appl Polym Sci 112:3436–3441CrossRef
54.
Zurück zum Zitat Buckley A, Stuetz D, Serad GA (1987) Polybenzimidazoles. In: Kroschwitz JI (ed) Encyclopedia of polymer science and engineering. Wiley, New York, pp 572–601 Buckley A, Stuetz D, Serad GA (1987) Polybenzimidazoles. In: Kroschwitz JI (ed) Encyclopedia of polymer science and engineering. Wiley, New York, pp 572–601
55.
Zurück zum Zitat Kojima T, Yokota R, Kochi M et al (1980) Dilute solution properties of a polybenzimidazole. J Polym Sci B 18:1673–1683 Kojima T, Yokota R, Kochi M et al (1980) Dilute solution properties of a polybenzimidazole. J Polym Sci B 18:1673–1683
56.
Zurück zum Zitat Marvel C S, Ariz T, Vogel HA (1965) Polybenzimidazoles and their preparation. US patent 3,174,947 Marvel C S, Ariz T, Vogel HA (1965) Polybenzimidazoles and their preparation. US patent 3,174,947
57.
Zurück zum Zitat Dang TD, Wang CS, Click WE (1997) Polybenzobisthiazoles with crosslinking sites for improved fibre axial compressive strength. Polymer 38:621–629CrossRef Dang TD, Wang CS, Click WE (1997) Polybenzobisthiazoles with crosslinking sites for improved fibre axial compressive strength. Polymer 38:621–629CrossRef
58.
Zurück zum Zitat Musto P, Karasz FE, Macknight WJ (1989) Hydrogen-bonding in polybenzimidazole polyimide systems—a fourier-transform infrared investigation using low-molecular-weight monofunctional probes. Polymer 30:1012–1021CrossRef Musto P, Karasz FE, Macknight WJ (1989) Hydrogen-bonding in polybenzimidazole polyimide systems—a fourier-transform infrared investigation using low-molecular-weight monofunctional probes. Polymer 30:1012–1021CrossRef
59.
Zurück zum Zitat Musto P, Karasz FE, Macknight WJ (1993) Fourier-transform infrared-spectroscopy on the thermooxidative degradation of polybenzimidazole and of a polybenzimidazole polyetherimide blend. Polymer 34:2934–2945CrossRef Musto P, Karasz FE, Macknight WJ (1993) Fourier-transform infrared-spectroscopy on the thermooxidative degradation of polybenzimidazole and of a polybenzimidazole polyetherimide blend. Polymer 34:2934–2945CrossRef
60.
Zurück zum Zitat Guerra G, Choe S, Williams DJ et al (1988) Fourier-transform infrared-spectroscopy of some miscible polybenzimidazole/polyimide blends. Macromolecules 21:231–234CrossRef Guerra G, Choe S, Williams DJ et al (1988) Fourier-transform infrared-spectroscopy of some miscible polybenzimidazole/polyimide blends. Macromolecules 21:231–234CrossRef
61.
Zurück zum Zitat Bouchet R, Siebert E (1999) Proton conduction in acid doped polybenzimidazole. Solid State Ionics 118:287–299CrossRef Bouchet R, Siebert E (1999) Proton conduction in acid doped polybenzimidazole. Solid State Ionics 118:287–299CrossRef
62.
Zurück zum Zitat Glipa X, Bonnet B, Mula B et al (1999) Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole. J Mater Chem 9:3045–3049CrossRef Glipa X, Bonnet B, Mula B et al (1999) Investigation of the conduction properties of phosphoric and sulfuric acid doped polybenzimidazole. J Mater Chem 9:3045–3049CrossRef
63.
Zurück zum Zitat Kawahara M, Morita J, Rikukawa M et al (2000) Synthesis and proton conductivity of thermally stable polymer electrolyte: poly(benzimidazole) complexes with strong acid molecules. Electrochim Acta 45:1395–1398CrossRef Kawahara M, Morita J, Rikukawa M et al (2000) Synthesis and proton conductivity of thermally stable polymer electrolyte: poly(benzimidazole) complexes with strong acid molecules. Electrochim Acta 45:1395–1398CrossRef
64.
Zurück zum Zitat Voyiatzis GA (2005) Spectroelectrochemical investigation of the ability of PBI-based membranes to be acid doped. Paper presented at symposium on high temperature PEM fuel cells, Rio, Patras, Greece, 13–14 Sept 2005 Voyiatzis GA (2005) Spectroelectrochemical investigation of the ability of PBI-based membranes to be acid doped. Paper presented at symposium on high temperature PEM fuel cells, Rio, Patras, Greece, 13–14 Sept 2005
65.
Zurück zum Zitat Li Q, He R, Berg RW et al (2004) Water uptake and acid doping of polybenzimidazoles as electrolyte membranes for fuel cells. Solid State Ionics 168:177–185CrossRef Li Q, He R, Berg RW et al (2004) Water uptake and acid doping of polybenzimidazoles as electrolyte membranes for fuel cells. Solid State Ionics 168:177–185CrossRef
66.
Zurück zum Zitat Hughes CE, Haufe S, Angerstein B et al (2004) Probing structure and dynamics in poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] fuel cells with magic-angle spinning NMR. J Phys Chem 108:13626–13631CrossRef Hughes CE, Haufe S, Angerstein B et al (2004) Probing structure and dynamics in poly[2,2′-(m-phenylene)-5,5′-bibenzimidazole] fuel cells with magic-angle spinning NMR. J Phys Chem 108:13626–13631CrossRef
67.
Zurück zum Zitat Kumbharkar SC, Islam MN, Potrekar RA et al (2009) Variation in acid moiety of polybenzimidazoles: investigation of physico-chemical properties towards their applicability as proton exchange and gas separation membrane materials. Polymer 50:1403–1413CrossRef Kumbharkar SC, Islam MN, Potrekar RA et al (2009) Variation in acid moiety of polybenzimidazoles: investigation of physico-chemical properties towards their applicability as proton exchange and gas separation membrane materials. Polymer 50:1403–1413CrossRef
68.
Zurück zum Zitat Asensio JA, Borrós S, Gómez-Romero P (2002) Proton-conducting polymers based on benzimidazoles and sulfonated benzimidazoles. J Polym Sci A 40:3703–3710CrossRef Asensio JA, Borrós S, Gómez-Romero P (2002) Proton-conducting polymers based on benzimidazoles and sulfonated benzimidazoles. J Polym Sci A 40:3703–3710CrossRef
69.
Zurück zum Zitat Yang JS, Aili D, Li QF et al (2013) Benzimidazole grafted polybenzimidazoles for proton exchange membrane fuel cells. Polym Chem 4:4768–4775CrossRef Yang JS, Aili D, Li QF et al (2013) Benzimidazole grafted polybenzimidazoles for proton exchange membrane fuel cells. Polym Chem 4:4768–4775CrossRef
70.
Zurück zum Zitat Hu M, Pearce EM, Kwei TK (1993) Modification of polybenzimidazole: synthesis and thermal stability of poly(N1-methylbenzimidazole) and poly(N1, N3-dimethylbenzimidazolium) salt. J Polym Sci A 31:553–561CrossRef Hu M, Pearce EM, Kwei TK (1993) Modification of polybenzimidazole: synthesis and thermal stability of poly(N1-methylbenzimidazole) and poly(N1, N3-dimethylbenzimidazolium) salt. J Polym Sci A 31:553–561CrossRef
71.
Zurück zum Zitat Klaehn JR, Luther TA, Orme CJ et al (2007) Soluble N-substituted organosilane polybenzimidazoles. Macromolecules 40:7487–7492CrossRef Klaehn JR, Luther TA, Orme CJ et al (2007) Soluble N-substituted organosilane polybenzimidazoles. Macromolecules 40:7487–7492CrossRef
72.
Zurück zum Zitat Hanley TR, Helminiak TE, Benner CL (1978) Expansion of aromatic heterocyclic polymers in salt solution. J Appl Polym Sci 22:2965–2978CrossRef Hanley TR, Helminiak TE, Benner CL (1978) Expansion of aromatic heterocyclic polymers in salt solution. J Appl Polym Sci 22:2965–2978CrossRef
73.
Zurück zum Zitat Lin HL, Chen YC, Li CC et al (2008) Preparation of PBI/PTFE composite membranes from PBI in N, N′-dimethyl acetamide solutions with various concentrations of LiCl. J Power Sources 181:228–236CrossRef Lin HL, Chen YC, Li CC et al (2008) Preparation of PBI/PTFE composite membranes from PBI in N, N′-dimethyl acetamide solutions with various concentrations of LiCl. J Power Sources 181:228–236CrossRef
74.
Zurück zum Zitat Litt M, Ameri R, Wang Y et al (1999) Polybenzimidazoles/phosphoric acid solid polymer electrolytes: mechanical and electrical properties. In: Nazri GA, Julien C, Rougier A (eds) MRS Proceedings 548. Materials Research Society, Warrendale, pp 313–323 Litt M, Ameri R, Wang Y et al (1999) Polybenzimidazoles/phosphoric acid solid polymer electrolytes: mechanical and electrical properties. In: Nazri GA, Julien C, Rougier A (eds) MRS Proceedings 548. Materials Research Society, Warrendale, pp 313–323
75.
Zurück zum Zitat Wang B, Tang Y, Wen Z et al (2009) Dissolution and regeneration of polybenzimidazoles using ionic liquids. Eur Polym J 45:2962–2965CrossRef Wang B, Tang Y, Wen Z et al (2009) Dissolution and regeneration of polybenzimidazoles using ionic liquids. Eur Polym J 45:2962–2965CrossRef
76.
Zurück zum Zitat Xiao L, Zhang H, Scanlon E et al (2005) High-temperature polybenzimidazole fuel cell membranes via a sol-gel process. Chem Mater 17:5328–5333CrossRef Xiao L, Zhang H, Scanlon E et al (2005) High-temperature polybenzimidazole fuel cell membranes via a sol-gel process. Chem Mater 17:5328–5333CrossRef
77.
Zurück zum Zitat Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated polybenzimidazoles. Eur Polym J 41:1589–1595CrossRef Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated polybenzimidazoles. Eur Polym J 41:1589–1595CrossRef
78.
Zurück zum Zitat Chuang SW, Hsu SLC (2006) Synthesis and properties of a new fluorine-containing polybenzimidazole for high-temperature fuel-cell applications. J Polym Sci A 44:4508–4513CrossRef Chuang SW, Hsu SLC (2006) Synthesis and properties of a new fluorine-containing polybenzimidazole for high-temperature fuel-cell applications. J Polym Sci A 44:4508–4513CrossRef
79.
Zurück zum Zitat Yang JS, Li QF, Cleemann LN et al (2013) Cross-linked hexafluoropropylidene polybenzimidazole membranes with chloromethyl polysulfone for fuel cell applications. Adv Energy Mater 3:622–630CrossRef Yang JS, Li QF, Cleemann LN et al (2013) Cross-linked hexafluoropropylidene polybenzimidazole membranes with chloromethyl polysulfone for fuel cell applications. Adv Energy Mater 3:622–630CrossRef
80.
Zurück zum Zitat Dai H, Zhang H, Zhong H et al (2010) Properties of polymer electrolyte membranes based on poly(aryl ether benzimidazole) and sulphonated poly(aryl ether benzimidazole) for high temperature PEMFCs. Fuel Cells 10:754–761CrossRef Dai H, Zhang H, Zhong H et al (2010) Properties of polymer electrolyte membranes based on poly(aryl ether benzimidazole) and sulphonated poly(aryl ether benzimidazole) for high temperature PEMFCs. Fuel Cells 10:754–761CrossRef
81.
Zurück zum Zitat Li J, Li X, Zhao Y et al (2012) High-temperature proton-exchange-membrane fuel cells using an ether-containing polybenzimidazole membrane as electrolyte. ChemSusChem 5:896–900CrossRef Li J, Li X, Zhao Y et al (2012) High-temperature proton-exchange-membrane fuel cells using an ether-containing polybenzimidazole membrane as electrolyte. ChemSusChem 5:896–900CrossRef
82.
Zurück zum Zitat Yang JS, Aili D, Li QF et al (2013) Covalently cross-linked sulfone polybenzimidazole membranes by poly (vinylbenzyl chloride) for fuel cell applications. ChemSusChem 6:275–282CrossRef Yang JS, Aili D, Li QF et al (2013) Covalently cross-linked sulfone polybenzimidazole membranes by poly (vinylbenzyl chloride) for fuel cell applications. ChemSusChem 6:275–282CrossRef
83.
Zurück zum Zitat Chuang SW, Hsu SLC, Liu YH (2007) Synthesis and properties of fluorine-containing polybenzimidazole/silica nanocomposite membranes for proton exchange membrane fuel cells. J Membr Sci 305:353–363CrossRef Chuang SW, Hsu SLC, Liu YH (2007) Synthesis and properties of fluorine-containing polybenzimidazole/silica nanocomposite membranes for proton exchange membrane fuel cells. J Membr Sci 305:353–363CrossRef
84.
Zurück zum Zitat Wang JTW, Hsu SLC (2011) Enhanced high-temperature polymer electrolyte membrane for fuel cells based on polybenzimidazole and ionic liquids. Electrochim Acta 56:2842–2846CrossRef Wang JTW, Hsu SLC (2011) Enhanced high-temperature polymer electrolyte membrane for fuel cells based on polybenzimidazole and ionic liquids. Electrochim Acta 56:2842–2846CrossRef
85.
Zurück zum Zitat Qian GQ, Smith DW, Benicewicz BC (2009) Synthesis and characterization of high molecular weight perfluorocyclobutyl containing polybenzimidazoles (PFCB–PBI) for high temperature polymer electrolyte membrane fuel cells. Polymer 50:3911–3916CrossRef Qian GQ, Smith DW, Benicewicz BC (2009) Synthesis and characterization of high molecular weight perfluorocyclobutyl containing polybenzimidazoles (PFCB–PBI) for high temperature polymer electrolyte membrane fuel cells. Polymer 50:3911–3916CrossRef
86.
Zurück zum Zitat Pu H, Wang L, Pan HY et al (2010) Synthesis and characterization of fluorine-containing polybenzimidazole for proton conducting membranes in fuel cells. J Polym Sci A 48:2115–2122CrossRef Pu H, Wang L, Pan HY et al (2010) Synthesis and characterization of fluorine-containing polybenzimidazole for proton conducting membranes in fuel cells. J Polym Sci A 48:2115–2122CrossRef
87.
Zurück zum Zitat Xiao L, Zhang H, Jana T et al (2005) Synthesis and characterization of pyridine-based polybenzimidazoles for high temperature polymer electrolyte membrane fuel cell applications. Fuel Cells 5:287–295CrossRef Xiao L, Zhang H, Jana T et al (2005) Synthesis and characterization of pyridine-based polybenzimidazoles for high temperature polymer electrolyte membrane fuel cell applications. Fuel Cells 5:287–295CrossRef
88.
Zurück zum Zitat Carollo A, Quartarone E, Tomasi C et al (2006) Developments of new proton conducting membranes based on different polybenzimidazole structures for fuel cells applications. J Power Sources 160:175–180CrossRef Carollo A, Quartarone E, Tomasi C et al (2006) Developments of new proton conducting membranes based on different polybenzimidazole structures for fuel cells applications. J Power Sources 160:175–180CrossRef
89.
Zurück zum Zitat Garbarczyk E, Nowinski JH, Gerbaldi C (2009) Pyridine-based PBI composite membranes for PEMFCs. Fuel Cells 9:349–355CrossRef Garbarczyk E, Nowinski JH, Gerbaldi C (2009) Pyridine-based PBI composite membranes for PEMFCs. Fuel Cells 9:349–355CrossRef
90.
Zurück zum Zitat Sannigrahi A, Ghosh S, Maity S et al (2010) Structurally isomeric monomers directed copolymerization of polybenzimidazoles and their properties. Polymer 51:5929–5941CrossRef Sannigrahi A, Ghosh S, Maity S et al (2010) Structurally isomeric monomers directed copolymerization of polybenzimidazoles and their properties. Polymer 51:5929–5941CrossRef
91.
Zurück zum Zitat Mustarelli P, Quartarone E, Grandi S et al (2012) Increasing the permanent conductivity of PBI membranes for HT-PEMs. Solid State Ionics 225:228–231CrossRef Mustarelli P, Quartarone E, Grandi S et al (2012) Increasing the permanent conductivity of PBI membranes for HT-PEMs. Solid State Ionics 225:228–231CrossRef
92.
Zurück zum Zitat Molleo MA, Chen X, Ploehn HJ et al (2014) High polymer content 3,5-pyridine-polybenzimidazole copolymer membranes with improved compressive properties. Fuel Cells 14:16–25CrossRef Molleo MA, Chen X, Ploehn HJ et al (2014) High polymer content 3,5-pyridine-polybenzimidazole copolymer membranes with improved compressive properties. Fuel Cells 14:16–25CrossRef
93.
Zurück zum Zitat Yang JS, Xu YX, Zhou L et al (2013) Hydroxyl pyridine containing polybenzimidazole membranes for proton exchange membrane fuel cells. J Membr Sci 446:318–325CrossRef Yang JS, Xu YX, Zhou L et al (2013) Hydroxyl pyridine containing polybenzimidazole membranes for proton exchange membrane fuel cells. J Membr Sci 446:318–325CrossRef
94.
Zurück zum Zitat Kim SK, Kim TH, Jung JW et al (2009) Polybenzimidazole containing benzimidazole side groups for high-temperature fuel cell applications. Polymer 50:3495–3502CrossRef Kim SK, Kim TH, Jung JW et al (2009) Polybenzimidazole containing benzimidazole side groups for high-temperature fuel cell applications. Polymer 50:3495–3502CrossRef
95.
Zurück zum Zitat Guan Y, Pu H, Jin M et al (2012) Proton conducting membranes based on poly(2,2′-imidazole-5,5′-bibenzimidazole). Fuel Cells 12:124–131CrossRef Guan Y, Pu H, Jin M et al (2012) Proton conducting membranes based on poly(2,2′-imidazole-5,5′-bibenzimidazole). Fuel Cells 12:124–131CrossRef
96.
Zurück zum Zitat Potrekar RA, Kulkarni MP, Kulkarni RA et al (2009) Polybenzimidazoles tethered with N-phenyl 1,2,4-triazole units as polymer electrolytes for fuel cells. J Polym Sci A 47:2289–2303CrossRef Potrekar RA, Kulkarni MP, Kulkarni RA et al (2009) Polybenzimidazoles tethered with N-phenyl 1,2,4-triazole units as polymer electrolytes for fuel cells. J Polym Sci A 47:2289–2303CrossRef
97.
Zurück zum Zitat Li X, Liu C, Zhang S et al (2012) Acid doped polybenzimidazoles containing 4-phenyl phthalazinone moieties for high-temperature PEMFC. J Membr Sci 423–424:128–135CrossRef Li X, Liu C, Zhang S et al (2012) Acid doped polybenzimidazoles containing 4-phenyl phthalazinone moieties for high-temperature PEMFC. J Membr Sci 423–424:128–135CrossRef
98.
Zurück zum Zitat Li X, Liu C, Zhang S et al (2013) Functionalized 4-phenyl phthalazinone-based polybenzimidazoles for high-temperature PEMFC. J Membr Sci 442:160–167CrossRef Li X, Liu C, Zhang S et al (2013) Functionalized 4-phenyl phthalazinone-based polybenzimidazoles for high-temperature PEMFC. J Membr Sci 442:160–167CrossRef
99.
Zurück zum Zitat Angioni S, Villa DC, Barco SD et al (2014) Polysulfonation of PBI-based membranes for HT-PEMFCs: a possible way to maintain high proton transport at a low H3PO4 doping level. J Mater Chem A 2:663–671CrossRef Angioni S, Villa DC, Barco SD et al (2014) Polysulfonation of PBI-based membranes for HT-PEMFCs: a possible way to maintain high proton transport at a low H3PO4 doping level. J Mater Chem A 2:663–671CrossRef
100.
Zurück zum Zitat Xu N, Guo X, Fang J et al (2009) Synthesis of novel polybenzimidazoles with pendant amino groups and the formation of their crosslinked membranes for medium temperature fuel cell applications. J Polym Sci A 47:6992–7002CrossRef Xu N, Guo X, Fang J et al (2009) Synthesis of novel polybenzimidazoles with pendant amino groups and the formation of their crosslinked membranes for medium temperature fuel cell applications. J Polym Sci A 47:6992–7002CrossRef
101.
Zurück zum Zitat Bhadra S, Kim NH, Lee JH (2010) A new self-cross-linked, net-structured, proton conducting polymer membrane for high temperature proton exchange membrane fuel cells. J Membr Sci 349:304–311CrossRef Bhadra S, Kim NH, Lee JH (2010) A new self-cross-linked, net-structured, proton conducting polymer membrane for high temperature proton exchange membrane fuel cells. J Membr Sci 349:304–311CrossRef
102.
Zurück zum Zitat Xu H, Chen K, Guo X et al (2007) Synthesis of hyperbranched polybenzimidazoles and their membrane formation. J Membr Sci 288:255–260CrossRef Xu H, Chen K, Guo X et al (2007) Synthesis of hyperbranched polybenzimidazoles and their membrane formation. J Membr Sci 288:255–260CrossRef
103.
Zurück zum Zitat Weber J, Kreuer KD, Maier J et al (2008) Proton conductivity enhancement by nanostructural control of poly(benzimidazole)-phosphoric acid adducts. Adv Mater 20:2595–2598CrossRef Weber J, Kreuer KD, Maier J et al (2008) Proton conductivity enhancement by nanostructural control of poly(benzimidazole)-phosphoric acid adducts. Adv Mater 20:2595–2598CrossRef
104.
Zurück zum Zitat Bhadra S, Kim NH, Choi JS et al (2010) Hyperbranched poly(benzimidazole-co-benzene) with honeycomb structure as a membrane for high-temperature proton-exchange membrane fuel cells. J Power Sources 195:2470–2477CrossRef Bhadra S, Kim NH, Choi JS et al (2010) Hyperbranched poly(benzimidazole-co-benzene) with honeycomb structure as a membrane for high-temperature proton-exchange membrane fuel cells. J Power Sources 195:2470–2477CrossRef
105.
Zurück zum Zitat Mader JA, Benicewicz BC (2010) Sulfonated polybenzimidazoles for high temperature PEM fuel cells. Macromolecules 43:6706–6715CrossRef Mader JA, Benicewicz BC (2010) Sulfonated polybenzimidazoles for high temperature PEM fuel cells. Macromolecules 43:6706–6715CrossRef
106.
Zurück zum Zitat Mader JA, Benicewicz BC (2011) Synthesis and properties of random copolymers of functionalised polybenzimidazoles for high temperature fuel cells. Fuel Cells 11:212–221CrossRef Mader JA, Benicewicz BC (2011) Synthesis and properties of random copolymers of functionalised polybenzimidazoles for high temperature fuel cells. Fuel Cells 11:212–221CrossRef
107.
Zurück zum Zitat Mader JA, Benicewicz BC (2011) Synthesis and properties of segmented block copolymers of functionalised polybenzimidazoles for high-temperature PEM fuel cells. Fuel Cells 11:222–237CrossRef Mader JA, Benicewicz BC (2011) Synthesis and properties of segmented block copolymers of functionalised polybenzimidazoles for high-temperature PEM fuel cells. Fuel Cells 11:222–237CrossRef
108.
Zurück zum Zitat Yu S, Benicewicz BC (2009) Synthesis and properties of functionalized polybenzimidazoles for high-temperature PEMFCs. Macromolecules 42:8640–8648CrossRef Yu S, Benicewicz BC (2009) Synthesis and properties of functionalized polybenzimidazoles for high-temperature PEMFCs. Macromolecules 42:8640–8648CrossRef
109.
Zurück zum Zitat Luo H, Pu H, Chang Z et al (2012) Crosslinked polybenzimidazole via a Diels–Alder reaction for proton conducting membranes. J Mater Chem 22:20696–20705CrossRef Luo H, Pu H, Chang Z et al (2012) Crosslinked polybenzimidazole via a Diels–Alder reaction for proton conducting membranes. J Mater Chem 22:20696–20705CrossRef
110.
Zurück zum Zitat Guan Y, Pu H, Wan D (2011) Synthesis and properties of poly[2,2′-(4,4′-(2,6-bis (phenoxy) benzonitrile))-5,5′-bibenzimidazole] for proton conducting membranes in fuel cells. Polym Chem 2:1287–1292CrossRef Guan Y, Pu H, Wan D (2011) Synthesis and properties of poly[2,2′-(4,4′-(2,6-bis (phenoxy) benzonitrile))-5,5′-bibenzimidazole] for proton conducting membranes in fuel cells. Polym Chem 2:1287–1292CrossRef
111.
Zurück zum Zitat Maity S, Jana T (2013) Soluble polybenzimidazoles for PEM: synthesized from efficient, inexpensive, readily accessible alternative tetraamine monomer. Macromolecules 46:6814–6823CrossRef Maity S, Jana T (2013) Soluble polybenzimidazoles for PEM: synthesized from efficient, inexpensive, readily accessible alternative tetraamine monomer. Macromolecules 46:6814–6823CrossRef
112.
Zurück zum Zitat Peron J, Ruiz E, Jones DJ et al (2008) Solution sulfonation of a novel polybenzimidazole. A proton electrolyte for fuel cell application. J Membr Sci 314:247–256CrossRef Peron J, Ruiz E, Jones DJ et al (2008) Solution sulfonation of a novel polybenzimidazole. A proton electrolyte for fuel cell application. J Membr Sci 314:247–256CrossRef
113.
Zurück zum Zitat Hu J, Luo J, Wagner P et al (2009) Anhydrous proton conducting membranes based on electron-deficient nanoparticles/PBI-OO/PFSA composites for high-temperature PEMFC. Electrochem Commun 11:2324–2327CrossRef Hu J, Luo J, Wagner P et al (2009) Anhydrous proton conducting membranes based on electron-deficient nanoparticles/PBI-OO/PFSA composites for high-temperature PEMFC. Electrochem Commun 11:2324–2327CrossRef
114.
Zurück zum Zitat He R, Li Q, Jensen JO et al (2007) Doping phosphoric acid in polybenzimidazole membranes for high temperature proton exchange membrane fuel cells. J Polym Sci A 45:2989–2997CrossRef He R, Li Q, Jensen JO et al (2007) Doping phosphoric acid in polybenzimidazole membranes for high temperature proton exchange membrane fuel cells. J Polym Sci A 45:2989–2997CrossRef
115.
Zurück zum Zitat Angioni S, Righetti PP, Quartarone E et al (2011) Novel aryloxy-polybenzimidazoles as proton conducting membranes for high temperature PEMFCs. Int J Hydrogen Energy 36:7174–7182CrossRef Angioni S, Righetti PP, Quartarone E et al (2011) Novel aryloxy-polybenzimidazoles as proton conducting membranes for high temperature PEMFCs. Int J Hydrogen Energy 36:7174–7182CrossRef
116.
Zurück zum Zitat Nalawade A, Hassan MK, Jarrett WA et al (2011) Broadband dielectric spectroscopy studies of glassy-state relaxations in annealed poly(2,5-benzimidazole). Polym Int 61:55–64CrossRef Nalawade A, Hassan MK, Jarrett WA et al (2011) Broadband dielectric spectroscopy studies of glassy-state relaxations in annealed poly(2,5-benzimidazole). Polym Int 61:55–64CrossRef
117.
Zurück zum Zitat Asensio JA, Borro S, Gómez-Romero P (2003) Polymer electrolyte fuel cells based on phosphoric acid-impregnated poly(2,5-benzimidazole) membranes. J Electrochem Soc 151:A304–A310CrossRef Asensio JA, Borro S, Gómez-Romero P (2003) Polymer electrolyte fuel cells based on phosphoric acid-impregnated poly(2,5-benzimidazole) membranes. J Electrochem Soc 151:A304–A310CrossRef
118.
Zurück zum Zitat Asensio JA, Gómez-Romero P (2005) Recent developments on proton conducing poly(2.5-benzimidazole) (ABPBI) membranes for high temperature polymer electrolyte membrane fuel cells. Fuel Cells 5:336–343CrossRef Asensio JA, Gómez-Romero P (2005) Recent developments on proton conducing poly(2.5-benzimidazole) (ABPBI) membranes for high temperature polymer electrolyte membrane fuel cells. Fuel Cells 5:336–343CrossRef
119.
Zurück zum Zitat Kim SK, Kim TH, Jung JW et al (2008) Copolymers of poly(2,5-benzimidazole) and poly[2,2′-(p-phenylene)-5,5′-bibenzimidazole] for high-temperature fuel cell applications. Macromol Mater Eng 293:914–921CrossRef Kim SK, Kim TH, Jung JW et al (2008) Copolymers of poly(2,5-benzimidazole) and poly[2,2′-(p-phenylene)-5,5′-bibenzimidazole] for high-temperature fuel cell applications. Macromol Mater Eng 293:914–921CrossRef
120.
Zurück zum Zitat Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated polybenzimidazoles. Chem J Chinese Universities 26:2145–2148 Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated polybenzimidazoles. Chem J Chinese Universities 26:2145–2148
121.
Zurück zum Zitat Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated fluorine containing polybenzimidazoles. Acta Chimica Sinica 63:667–670 Qing S, Huang W, Yan D (2005) Synthesis and characterization of thermally stable sulfonated fluorine containing polybenzimidazoles. Acta Chimica Sinica 63:667–670
122.
Zurück zum Zitat Wang G, Xiao G, Yan D (2011) Synthesis and properties of soluble sulfonated polybenzimidazoles derived from asymmetric dicarboxylic acid monomers with sulfonate group as proton exchange membrane. J Membr Sci 369:388–396CrossRef Wang G, Xiao G, Yan D (2011) Synthesis and properties of soluble sulfonated polybenzimidazoles derived from asymmetric dicarboxylic acid monomers with sulfonate group as proton exchange membrane. J Membr Sci 369:388–396CrossRef
123.
Zurück zum Zitat Wang J, Song Y, Zhang C et al (2008) Alternating copolymer of sulfonated poly(ether ether ketone-benzimidazole)s (SPEEK-BI) bearing acid and base moieties. Macromol Chem Phys 209:1495–1502CrossRef Wang J, Song Y, Zhang C et al (2008) Alternating copolymer of sulfonated poly(ether ether ketone-benzimidazole)s (SPEEK-BI) bearing acid and base moieties. Macromol Chem Phys 209:1495–1502CrossRef
124.
Zurück zum Zitat Krishnan NN, Prabhuram J, Hong YT et al (2010) Fabrication of MEA with hydrocarbon based membranes using low temperature decal method for DMFC. Int J Hydrogen Energy 35:5647–5655CrossRef Krishnan NN, Prabhuram J, Hong YT et al (2010) Fabrication of MEA with hydrocarbon based membranes using low temperature decal method for DMFC. Int J Hydrogen Energy 35:5647–5655CrossRef
125.
Zurück zum Zitat Ng F, Bae B, Miyatake K et al (2011) Polybenzimidazole block sulfonated poly(arylene ether sulfone) ionomers. Chem Commun 47:8895–8897CrossRef Ng F, Bae B, Miyatake K et al (2011) Polybenzimidazole block sulfonated poly(arylene ether sulfone) ionomers. Chem Commun 47:8895–8897CrossRef
126.
Zurück zum Zitat Ko H, Yu DM, Choi JH et al (2012) Synthesis and characterization of intermolecular ionic cross-linked sulfonated poly(arylene ether sulfone)s for direct methanol fuel cells. J Membr Sci 390–391:226–234CrossRef Ko H, Yu DM, Choi JH et al (2012) Synthesis and characterization of intermolecular ionic cross-linked sulfonated poly(arylene ether sulfone)s for direct methanol fuel cells. J Membr Sci 390–391:226–234CrossRef
127.
Zurück zum Zitat Ferreiro JJ, Campa JDL, Lozano AE et al (2008) Synthesis and evaluation of properties of novel poly(benzimidazole-amide)s. J Polym Sci A 46:7566–7577CrossRef Ferreiro JJ, Campa JDL, Lozano AE et al (2008) Synthesis and evaluation of properties of novel poly(benzimidazole-amide)s. J Polym Sci A 46:7566–7577CrossRef
128.
Zurück zum Zitat Yuan S, Guo X, Aili D et al (2014) Poly(imide benzimidazole)s for high temperature polymer electrolyte membrane fuel cells. J Membr Sci 454:351–358CrossRef Yuan S, Guo X, Aili D et al (2014) Poly(imide benzimidazole)s for high temperature polymer electrolyte membrane fuel cells. J Membr Sci 454:351–358CrossRef
129.
Zurück zum Zitat Bower EA, Rafalko JJ (1986) Process for modifying polybenzimidazole polymers with ethylene carbonates. US Patent 4,599,388 Bower EA, Rafalko JJ (1986) Process for modifying polybenzimidazole polymers with ethylene carbonates. US Patent 4,599,388
130.
Zurück zum Zitat Sansone MJ, Gupta B, Stackman RW (1989) Sulfoalkylation of polybenzimidazole. US Patent 4,814,399 Sansone MJ, Gupta B, Stackman RW (1989) Sulfoalkylation of polybenzimidazole. US Patent 4,814,399
131.
Zurück zum Zitat Sansone MJ (1990) N-substituted polybenzimidazole polymer. US Patent 4,898,917 Sansone MJ (1990) N-substituted polybenzimidazole polymer. US Patent 4,898,917
132.
Zurück zum Zitat Cassidy PE (ed) (1980) Thermally stable polymers, synthesis and properties. Marcel Dekker, New York Cassidy PE (ed) (1980) Thermally stable polymers, synthesis and properties. Marcel Dekker, New York
133.
Zurück zum Zitat Gieselman MB, Reynolds JR (1992) Water-soluble polybenzimidazole-based polyelectrolytes. Macromolecules 25:4832–4834CrossRef Gieselman MB, Reynolds JR (1992) Water-soluble polybenzimidazole-based polyelectrolytes. Macromolecules 25:4832–4834CrossRef
134.
Zurück zum Zitat Gieselman MB, Reynolds JR (1993) Aramid and imidazole based polyelectrolytes—physical-properties and ternary phase-behavior with poly(benzobisthiazole) in methanesulphonic-acid. Macromolecules 26:5633–5642CrossRef Gieselman MB, Reynolds JR (1993) Aramid and imidazole based polyelectrolytes—physical-properties and ternary phase-behavior with poly(benzobisthiazole) in methanesulphonic-acid. Macromolecules 26:5633–5642CrossRef
135.
Zurück zum Zitat Glipa X, Haddad ME, Jones DJ et al (1997) Synthesis and characterisation of sulphonated polybenzimidazole: a highly conducting proton exchange polymer. Solid State Ionics 97:323–331CrossRef Glipa X, Haddad ME, Jones DJ et al (1997) Synthesis and characterisation of sulphonated polybenzimidazole: a highly conducting proton exchange polymer. Solid State Ionics 97:323–331CrossRef
136.
Zurück zum Zitat Roziere J, Jones DJ, Marrony M et al (2001) On the doping of sulphonated polybenzimidazole with strong bases. Solid State Ionics 145:61–68CrossRef Roziere J, Jones DJ, Marrony M et al (2001) On the doping of sulphonated polybenzimidazole with strong bases. Solid State Ionics 145:61–68CrossRef
137.
Zurück zum Zitat Bae JM, Honma I, Murata M et al (2002) Properties of selected sulphonated polymers as proton-conducting electrolytes for polymer electrolyte fuel cells. Solid State Ionics 147:189–194CrossRef Bae JM, Honma I, Murata M et al (2002) Properties of selected sulphonated polymers as proton-conducting electrolytes for polymer electrolyte fuel cells. Solid State Ionics 147:189–194CrossRef
138.
Zurück zum Zitat Pu H, Liu Q, Liu G (2004) Methanol permeation and proton conductivity of acid-doped poly(N-ethylbenzimidazole) and poly(N-methylbenzimidazole). J Membr Sci 241:169–175CrossRef Pu H, Liu Q, Liu G (2004) Methanol permeation and proton conductivity of acid-doped poly(N-ethylbenzimidazole) and poly(N-methylbenzimidazole). J Membr Sci 241:169–175CrossRef
139.
Zurück zum Zitat Pu H, Liu G (2005) Synthesis and solubility of poly(N-methylbenzimidazole) and poly(N-ethylbenzimidazole): control of degree of alkylation. Polym Int 54:175–179CrossRef Pu H, Liu G (2005) Synthesis and solubility of poly(N-methylbenzimidazole) and poly(N-ethylbenzimidazole): control of degree of alkylation. Polym Int 54:175–179CrossRef
140.
Zurück zum Zitat Sukumar PR, Wu W, Markova D et al (2007) Functionalized poly(benzimidazole)s as membrane materials for fuel cells. Macromol Chem Phys 208:2258–2267CrossRef Sukumar PR, Wu W, Markova D et al (2007) Functionalized poly(benzimidazole)s as membrane materials for fuel cells. Macromol Chem Phys 208:2258–2267CrossRef
141.
Zurück zum Zitat Namazi H, Ahmadi H (2011) Novel proton conducting membranes based on butylsulfonated poly[2,2′-(m-pyrazolidene)-5,5′-bibenzimidazole] (BS-PPBI): proton conductivity, acid doping and water uptake properties. J Membr Sci 383:280–288CrossRef Namazi H, Ahmadi H (2011) Novel proton conducting membranes based on butylsulfonated poly[2,2′-(m-pyrazolidene)-5,5′-bibenzimidazole] (BS-PPBI): proton conductivity, acid doping and water uptake properties. J Membr Sci 383:280–288CrossRef
142.
Zurück zum Zitat Lin HL, Hu CR, Lai SW et al (2012) Polybenzimidazole and butylsulfonate grafted polybenzimidazole blends for proton exchange membrane fuel cells. J Membr Sci 389:399–406CrossRef Lin HL, Hu CR, Lai SW et al (2012) Polybenzimidazole and butylsulfonate grafted polybenzimidazole blends for proton exchange membrane fuel cells. J Membr Sci 389:399–406CrossRef
Metadaten
Titel
Synthesis of Polybenzimidazoles
verfasst von
Jingshuai Yang
Ronghuan He
David Aili
Copyright-Jahr
2016
DOI
https://doi.org/10.1007/978-3-319-17082-4_7