Thioetherification of Poly(vinyl chloride) in the Presence of Ethvlenediamine

Abstract

The thioetherification of poly (vinyl chloride) (PVC) in ethylenediamine or ethylenediaminetetrahydrofuran has been compared with the reactions of model compounds e. g., s-butyl chloride, 1, 3- and 1, 4-dichlorobutane to. elucidate a polymer effect of this reaction. The rate of the thioetherification of PVC is proportional to [PVC] and [thiols] and is almost similar to that of s-butyl chloride. As the thioether group first formed activates remaining chlorine atom during the thioetherification of 1, 3- and 1, 4-dichlorobutane, chlorine atoms is PVC would presumably be activated by the thioether group introduced and probably by the formation of sulfonium salts. In addition, such a neighboring effect of aliphatic thioether group seemed to be stronger than that of aromatic thioether group.