Due to being excellent activators, sulfonamide groups were used to synthesize poly arylene ethers (PAEs) through meta-activated nucleophilic aromatic substitution (NAS). A series of N-alkyl-N-phenyl-3,5-difluorobenzene sulfonamides was synthesized, with alkyl groups ranging from methyl to dodecyl, along with N-allyl-N-phenyl-3,5-dilfluorobenzene sulfonamide. These sulfonamides were then polymerized with bisphenol-A and the molecular weights of the polymers were determined using gel permeation chromatography (GPC). Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) were used to determine the glass transition temperatures (T­g) of the polymers. Tg values were inversely proportional to the alkyl length chain of the polymer with the methyl version possessing a Tg of 122 °C while the dodecyl group exhibited a Tg of only 46 °C. Introduction of the allyl group provides potential access to “post” polymerization modification reactions through thiol-ene chemistry as well as a site for cross-linking to afford elastomers.

Toward high temperature ellastomers based on poly(arylene ether)s derived from 3,5-difluorobenzene sulfonamides

249th National Meeting (2015)

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