New Sulfonated Polyethers and Polynaphthylimides based on TNT Derivatives

Abstract

New sulfonated and non-sulfonated monomers — dinitro and diamino compounds — were prepared on the basis of 1,3,5-trinitrobenzene (TNB) which is the demethylation product of 2,4,6-trinitrotoluene (TNT). The sulfonated dinitrocompounds interacted with different binuclear bis-phenols under the conditions of aromatic nucleophilic nitrodisplacement reactions. Polyethers of moderate molecular weights were prepared on the basis of dinitrocompound containing electron-withdrawing 3,5-dinitrodiphenyl sulfone-4′-sulfonic acid “bridging” groups. Copolymers and blends with other sulfonated polymers were prepared to improve the film-forming properties of the polyethers developed on the basis of 3,5-dinitrodiphenyl sulfone-4′-sulfonic acid. High molecular weight sulfonated polynaphthylimides were prepared by the interaction of sulfonated diamine containing electron-donating ether group — 3,5-diaminodiphenyl ether-4′-sulfonic acid — with bis(naphthalic anhydride)s. The sulfonated polyethers and polynaphthylimides thus obtained contain sulfonic acid groups in the side chains.

Effect of Chemical Structure and Degree of Branching on the Stability of Proton Exchange Membranes Based on Sulfonated Polynaphthylimides

“…Over the past few decades, hundreds of low-cost sulfonated polymers, such as sulfonated polyether-ether-ketone [15][16][17][18][19][20], sulfonated polyether sulfone [21][22][23][24][25][26][27][28][29][30][31], and sulfonated polynaphthylimides with different chemical structures, have been synthesized for PEMFCs applications [28,29,32]. Among them, sulfonated polynaphthylimides (SPIs) have attracted considerable attention because of their low cost, excellent physical properties, high methanol gas barrier ability, high thermal stability, and easy-to-adjust chemical structure [33][34][35][36]. However, the unsatisfied stability of SPI membrane in a fuel cell under high temperature and high humidity conditions cannot be ignored [37][38][39].…”