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Organotin compounds as PVC stabilizers
When poly(vinyl chloride) is fabricated, it passes between rollers (calendars) at about 200 ◦C, which causes elimination of some HCl at allylic defects in the polymer, as shown below (Figure 3.3.1). Furthermore, the released HCl induces further elimination, giving a polyolefin structure with a yellow coloration, which turns red, and then black, after which the polymer becomes brittle. This degeneration can be inhibited by organotin stabilizers, often organotin mercaptides that appear to have two principal functions. Firstly, they react with the HCl to give organotin chlorides, which do not catalyze the elimination process. Secondly, they substitute the chloride at the reactive sites, introducing other groups, such as mercaptide groups, which are not easily eliminated. Organotin maleates may also remove diene units by the Diels–Alder reaction.