Structure–property relationships of ionene polymers

Abstract

Abstract The synthesis of new ionenes was accomplished by the reaction of novel diamines and dihalides. A new class of crosslinkable ionenes was made possible by the synthesis of tertiary diamines with acrylate functionality, generated ultimately from diepoxides and secondary amines. Other tertiary diamines were produced by endcapping of diols with tolylene diisocyanate, followed by reaction with N , N ‐dimethylethanolamine and also termination of living poly(tetrahydrofuran) polymer with dimethylamine. New dihalides were produced by the opening of diepoxides with ω‐bromoacids. These diamines and dihalides underwent Menschutkin reactions providing novel ionenes for structure–property relationship studies. Correlations were drawn concerning amine nucleophilicity, dihalide nucleofugascity, and molecular weight. Stress–strain and thermal data reflected the effects of ionic domains and large flexible segments in the polymers. Also considered were the electrical conductivity, moisture–vapor transmission, and oxygen permeability of these materials.