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High Performance Polymers
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New Sulfonated Polyethers and Polynaphthylimides based on TNT Derivatives

Alexander L. Rusanov

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

Ludmila G. Komarova

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

Elena G. Bulycheva

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

Margarita G. Bugaenko

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

Nataliya M. Belomoina

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia, bel{at}ineos.ac.ru

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.

Key Words: proton-exchanging membranes • fuel cells • sulfonic acid groups • dinitrocompounds • sulfonated diamines • sulfonated polyethers • sulfonated polynaphthylimides

This version was published on October 1, 2009

High Performance Polymers, Vol. 21, No. 5, 508-521 (2009)
DOI: 10.1177/0954008309339201
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