Alternating copolymerization of carbonyl sulfide with aziridines

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Abstract
The copolymerization of carbonyl sulfide with aziridines such as ethylenimine, propylenimine, and N‐ethylethylenimine was studied in various organic solvents. The copolymerizations occurred easily without the addition of any catalyst and gave white powdery crystalline copolymers. The copolymers produced were insoluble in many organic solvents, but soluble in p‐chlorophenol and dimethyl sulfoxide. The elementary analyses and the infrared spectra showed that alternating copolymers which have a thiourethane structure were produced. In the copolymerization of carbonyl sulfide with ethylenimine, both the polymer yield and the molecular weight of the resulting polymer increased with the use of a solvent having a higher dielectric constant, and also with an increase in the ratio of carbonyl sulfide to imine in the feed. The rate of copolymerization of carbonyl sulfide with aziridines was in the order of ethylenimine > propylenimine > and N‐ethylethylenimine. Irradiation of the copolymers improved their thermal properties and increased their melting point.

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