Studies on reactions of the N-phosphonium salts of pyridines. XIII. Direct polycondensation reaction of carbon dioxide or disulfide with diamines under mild conditions
Article first published online: 11 MAR 2003
Copyright © 1975 John Wiley & Sons, Inc.
Journal of Polymer Science: Polymer Chemistry Edition
Volume 13, Issue 4, pages 785–795, April 1975
How to Cite
Yamazaki, N., Iguchi, T. and Higashi, F. (1975), Studies on reactions of the N-phosphonium salts of pyridines. XIII. Direct polycondensation reaction of carbon dioxide or disulfide with diamines under mild conditions. J. Polym. Sci. Polym. Chem. Ed., 13: 785–795. doi: 10.1002/pol.1975.170130402
- Issue published online: 11 MAR 2003
- Article first published online: 11 MAR 2003
- Manuscript Revised: 12 NOV 1974
- Manuscript Received: 6 AUG 1974
Polyureas of high molecular weight were obtained by the direct polycondensation reaction of carbon dioxide with diamines at 40°C for several hours under a pressure of carbon dioxide (below 30 atm) by use of diphenyl phosphite in pyridine. Optimal temperature and pressure were 40°C and 20 atm of carbon dioxide. The polycondensation reaction was also affected by solvents and type and amounts of tertiary amines. Pyridine was most effective as tertiary amine and solvent as well. Of the phosphorous compounds used, triaryl phosphites and diphenyl phosphite were most effective, but trialkyl phosphites failed to give polymer. The reaction was assumed to proceed via a carbamyl N-phosphonium salt of pyridine formed by dephenoxylation of phosphites. Similarly, polythioureas were prepared by heating a mixture of carbon disulfide, diamines, and diphenyl phosphite in pyridine at 40°C for 6 hr under nitrogen.