Abstract: | The copolymerization of aziridines and cyclic imides was studied. Aziridines copolymerized alternately with cyclic imides to give crystalline polyamides. Ethylenimine and succinimide copolymerized to nylon 2,4, melting near 300°C., without any catalyst. Similarly, the corresponding crystalline polyamides were obtained from the systems of 1,2-propylenimine–succinimide, ethylenimine–glutarimide, and ethylenimine–phthalimide. The copolymerization of aziridines and cyclic imides in the presence of BF3OEt2 gave a copolymer which was rich in aziridine units, whereas, the addition of triethylamine had no influence on the copolymer composition. A mechanism of copolymerization was proposed based on the facts that N-tetramethylenesuccinamide was obtained by the reaction of pyrrolidine and succinimide, N-acetylethylenimine reacted with acetamide to yield N,N′-diacetylethylenediamine and that the rate of this copolymerization was dependent on the electrophilicity of imide. |