Polycondensation of alkylene dichlorides with alkylene polyamines

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Abstract
Polycondensation of ethylene dichloride and 3,3′‐iminobis(propylamine) resulted in high molecular weight soluble polymers or insoluble gels, depending on the ratio of the reactants and the extent of reaction. It is shown that the functionality of a polyfunctional compound containing groups of unequal reactivities can be determined experimentally. The effective functionality of 3,3′‐iminobis(propylamine) was found to be 2.9 from gelation studies and 3.5 based on the relative reaction rates of the primary and secondary amino groups. By using the effective functionality value, the reaction kinetics can be treated in a simple manner. A typical soluble polymer formed has a low intrinsic viscosity and a very high M̄w/M̄n ratio. Condensations of other alkylene dichlorides and alkylene polyamines demonstrated the validity of Carothers' rule that high polymers will not result if formation of 5‐ or 6‐membered rings is possible.