Organic thermal stabilizers for rigid poly(vinyl chloride) I. Barbituric and thiobarbituric acids

Abstract

Barbituric acid (BA) and thiobarbituric acid (TBA) have been investigated as thermal stabilizers for rigid poly(vinyl chloride) (PVC) at 180°C, in air. The efficiency of these compounds as thermal stabilizers was evaluated by measuring the length of the induction period ( T s), during which no detectable amount of hydrogen chloride gas could be observed, and also from the rate of dehydrochlorination as measured by continuous potentiometric titration on one hand, and the extent of discoloration of the degraded polymer on the other. The stabilizing efficiencies were compared with that of dibasic lead carbonate (DBLC), dibasic lead stearate (DBLS), barium–cadmium–zinc stearate (Ba–Cd–Zn stearate), n-octyl tin mercaptide ( n-OTM) and dibutyl tin maleate (DBTM). With the exception of DBTM reference stabilizer which shows a comparable stabilizing efficiency with BA and TBA, the investigated organic stabilizers exhibit a greater efficiency than those of all other reference stabilizers. Moreover, they impart better color stability to the degraded samples. A radical mechanism for the stabilizing action is suggested. The stabilizing efficiency is attributed to the replacement of the labile chlorine atoms on the PVC chains by a relatively more stable moiety of the stabilizer. This disrupts the formation of conjugated double bonds, which are responsible for the discoloration.