Polyimides sulfonated naphthalenic

Genies, G., Mercier, R., Sillion, B., Gomet, N., Gebel, G. and Pineri, M. 2001. Soluble sulfonated naphthalenic polyimides as materials for proton exchange membranes. Polymer 42 359-373. 

Y. Yin, O. Yamada, K. Tanaka, K.-I. Okamoto, On the development of naphthalene-based sulfonated polyimide membranes for fuel cell applications. Polymer Journal 2006,38(3), 197-219. 

Scheme 6 Synthesis of sequenced sulfonated naphthalenic polyimides...

Membranes consisting of sequenced sulfonated naphthalenic polyimides (ionic block length of 5) also exhibit higher conductivity and A values... 

R. Petiau, N. Cornet, G. Gebel, M. Pineri, Stability study of sulfonated phthalic and naphthalenic polyimide structures in aqueous medium Polymer 42 (2001) 5097-5105. 

Sulfonated polyimides (SPI), especially sulfonated six-member ring (naphthalenic)polyimides, are proposed as promising candidates for PEMs because of their excellent chemical and thermal stability,... 

P. Chhabra, V. Choudhary, Synthesis and characterization of sulfonated naphthalenic polyimides based on 4, 4 -diaminodiphenylether-2, 2 -disulfonic acid and bis [4-(4-aminophenoxy) phenylhexafluoropropane] for fuel cell plications, Eur. Polym. J. 45 (5) (2009) 1467-1475. 

Genies C, Mercier R, Sillion B, Petiaud R, Comet N et al. (2001) Stability study of sulfonated phthaUc and naphthalenic polyimide stmctures in aqueous medium . Polymer 42 5097. 

As reported by Genius et al. [48] from a study on model compoimds, sulfonated naphthalenic polyimides prove to be more resistant to hydrolysis than their phthalic analogues. Few articles are devoted to the synthesis and characterization of sulfonated phthalic polyimides, whereas sulfonated naphthalenic polyimides have attracted much attention [53]. Rather few different naphthalenic dianhydride monomers are reported for the synthesis of SPIs (Fig. 2). 

Shang, Y., Xie, X., Jin, H., Guo, J., Wang, Y., Feng, S., Wang, S., Xu, J. (2006) Synthesis and characterization of novel sulfonated naphthalenic polyimides as proton conductive membrane for DMFC applications. European Polymer Journal, 42, 2987-2993. 

Genies, C., Mercier, R., SiUion, B., Comet, N., Gebel, G., and Pineri, M. (2001b). Stability stody of sulfonated phthalic and naphthalenic polyimide stmctores in aqueous medium. Polymer 42, 5097. Gil, M., Ji, X. L., Li, X. F., Na, H. Hampsey, J. E., and Lu, Y. F. (2004). Direct synthesis of sulfonated aromatic poly (ether ether ketone) proton exchange membranes for fuel cell applications. J. Membr. Sci. 234, 75. 

Einsla, B. R., Hong, Y. T., Kim, Y. S., Wang, F., Gunduz, N. and McGrath, J. E. 2004. Sulfonated naphthalene dianhydride based polyimide copolymers for proton-exchange-membrane fuel cells. 1. Monomer and copolymer synthesis. Journal of Polymer Science Part A Polymer Chemistry 42 862-874. 

MC MDI MEKP MF MMA MPEG MPF NBR NDI NR OPET OPP OSA PA PAEK PAI PAN PB PBAN PBI PBN PBS PBT PC PCD PCT PCTFE PE PEC PEG PEI PEK PEN PES PET PF PFA PI PIBI PMDI PMMA PMP PO PP PPA PPC PPO PPS PPSU Methyl cellulose Methylene diphenylene diisocyanate Methyl ethyl ketone peroxide Melamine formaldehyde Methyl methacrylate Polyethylene glycol monomethyl ether Melamine-phenol-formaldehyde Nitrile butyl rubber Naphthalene diisocyanate Natural rubber Oriented polyethylene terephthalate Oriented polypropylene Olefin-modified styrene-acrylonitrile Polyamide Poly(aryl ether-ketone) Poly(amide-imide) Polyacrylonitrile Polybutylene Poly(butadiene-acrylonitrile) Polybenzimidazole Polybutylene naphthalate Poly(butadiene-styrene) Poly(butylene terephthalate) Polycarbonate Polycarbodiimide Poly(cyclohexylene-dimethylene terephthalate) Polychlorotrifluoroethylene Polyethylene Chlorinated polyethylene Poly(ethylene glycol) Poly(ether-imide) Poly(ether-ketone) Polyethylene naphthalate Polyether sulfone Polyethylene terephthalate Phenol-formaldehyde copolymer Perfluoroalkoxy resin Polyimide Poly(isobutylene), Butyl rubber Polymeric methylene diphenylene diisocyanate Poly(methyl methacrylate) Poly(methylpentene) Polyolefins Polypropylene Polyphthalamide Chlorinated polypropylene Poly(phenylene oxide) Poly(phenylene sulfide) Poly(phenylene sulfone)... 

PB PBI PBMA PBO PBT(H) PBTP PC PCHMA PCTFE PDAP PDMS PE PEHD PELD PEMD PEC PEEK PEG PEI PEK PEN PEO PES PET PF PI PIB PMA PMMA PMI PMP POB POM PP PPE PPP PPPE PPQ PPS PPSU PS PSU PTFE PTMT PU PUR Poly(n.butylene) Poly(benzimidazole) Poly(n.butyl methacrylate) Poly(benzoxazole) Poly(benzthiazole) Poly(butylene glycol terephthalate) Polycarbonate Poly(cyclohexyl methacrylate) Poly(chloro-trifluoro ethylene) Poly(diallyl phthalate) Poly(dimethyl siloxane) Polyethylene High density polyethylene Low density polyethylene Medium density polyethylene Chlorinated polyethylene Poly-ether-ether ketone poly(ethylene glycol) Poly-ether-imide Poly-ether ketone Poly(ethylene-2,6-naphthalene dicarboxylate) Poly(ethylene oxide) Poly-ether sulfone Poly(ethylene terephthalate) Phenol formaldehyde resin Polyimide Polyisobutylene Poly(methyl acrylate) Poly(methyl methacrylate) Poly(methacryl imide) Poly(methylpentene) Poly(hydroxy-benzoate) Polyoxymethylene = polyacetal = polyformaldehyde Polypropylene Poly (2,6-dimethyl-l,4-phenylene ether) = Poly(phenylene oxide) Polyp araphenylene Poly(2,6-diphenyl-l,4-phenylene ether) Poly(phenyl quinoxaline) Polyphenylene sulfide, polysulfide Polyphenylene sulfone Polystyrene Polysulfone Poly(tetrafluoroethylene) Poly(tetramethylene terephthalate) Polyurethane Polyurethane rubber... 

This class of polymers has great thermal stability and promising short-term perfor-mance. °° The six-membered ring of naphthalenic imides is preferred over the five-membered ring of phthanic imides. The latter is susceptible to acid-catalyzed hydrolysis, which leads to chain scission and membrane embrittlement. An example of six-mem-bered ring polyimides is the block sulfonated copolyimides shown below. ... 

Polyimides have been the topic of investigation for fuel cells for many years [180-184]. By poly condensation of sulfonated amines and phthalic or naphthalen-ic anhydride it is possible to tailor statistic or block copolymers with good proton conductivity. Polyimides have some susceptibility to hydrolysis, better stability being achieved with naphthalenic structures [185]. Sulfonimide membranes [186, 187] have been investigated due their strong superacidity, water uptake and retention above 80 °C. However, although they are thermally quite stable, the hydrolytic stability is not high. 

Badami AS, Roy A, Lee HS, Li Y, McGrath JE. Morphological investigations of disulfonated poly(arylene ether sulfone)-fe-naphthalene dianhydride-based polyimide multiblock copolymers as potential high temperature proton exchange membranes. J Membr Sci 2009 328 (l-2) 156-64. 

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