Polymerization of oxiranylalkylamines and thiiranylalkylamines derived from achiral and racemic secondary amines

Abstract

Abstract The polymerization of N,N ‐diethyl‐ N ‐(oxirane‐2‐ylmethyl)amine (Ia), by initiator systems such as ZnEt 2 /H 2 O, ZnEt 2 /CH 3 OH, AlEt 3 /H 2 O, and others, gives only low molecular weight polymers with low yields. The corresponding thiirane derivative, N,N ‐diethyl‐ N ‐(thiirane‐2‐yl‐methyl)amine (IIa), with the same type of initiators gives high molecular weight polymers which are non‐crystalline contrary to the case of propylene sulfide. Physicochemical properties (UV and IR absorptions, neutralization and gelation during neutralization) of these polymers are studied. Higher homologues of IIa derived from racemic secondary amines R 1 R 2 NH are synthesized and polymerized with ZnEt 2 /H 2 O. The influence of the substitu ents R 1 and R 2 on the physical and chemical properties of the polymers is discussed.