STEP-GROWTH POLYMERIZATION OF BISTRIAZOLINEDIONES WITH 1,1-DIPHENYLETHYLENE

The reactions of 4-ethyl-1,2,4-triazoline-3,5-dione (ETD) (1) and 4-ph enyl-1,2,4-triazoline-3,5-dione (PhTD) (2) with 1,1-diphenylethylene ( DPE) (3) were investigated at room temperature. The reactions are very fast and are completed in less than 4 min. These reactions lead to th e formation of two 2:1 adducts via double Diels-Alder and Diels-Alder- ene reactions in a ratio of 1.35:1. The structure of these adducts whe re R = Et were determined by X-ray analysis of a single crystal. These compounds were used as models for the polymerization reactions. The r eaction of bistriazolinediones (1,6-bis-(3,5-dioxo-1,2,4-triazoline-4- yl)hexane and -(p-3,5-dioxo-1,2,4-triazoline-4-ylphenyl)methane) with (3) were carried out in dimethylformanide (DMF). The reactions are fas t and gave novel copolymers via repetitive double Diels-Alder and Diel s-Alderene polyaddition reactions. These polymers have intrinsic visco sities in a range about 0.08 to 0.31 dl g(-1) in DMF. Some physical pr operties and structural characterization of these copolymers have been studied and are reported.