The preparation and some properties of chlorinated tung oil

Summary The chlorination of tung oil was investigated, and certain chlorinated products were screened as plasticizers for polyvinyl chloride resin. Chlorine readily added at low temperatures (0 to 20°C.) as well as at higher temperature (75°C.). The chlorination was highly selective for triene conjugation as the disappearance of triene closely paralleled the amount of chlorine added during early staged to chlorination. Considerable conjugated diene is formed as indicated by characteristic ultraviolet absorption in the diene region. In later stages of chlorination considerable substitution occurs as evidenced by the fact that products containing more than 40% of chlorine could readily be obtained. All the products were more or less unstable, evolving hydrogen chloride and darkening at room temperature. The chlorinated tung oils were screened as plasticizers, at the 30% level, for polyvinyl chloride by using butyl epoxystearate as a stabilizer. Products containing small proportions of chlorine (less than about 20%) were not compatible with polyvinyl chloride; products containing moderate amounts (about 30%) were compatible and had some plasticizing effect but decomposed excessively on milling. Those products containing the highest proportion of chlorine (more than 40%) were compatible and did not decompose on milling or molding. These highly chlronated tung oilslowered the milling temperature of polyvinyl chloride copolymer but showed little, if any, ability to product compositions which are flexible at room temperature. Presented at the 32nd Annual Fall Meeting, American Oil Chemists' Society, Chicago, Ill., October 20–22, 1958. One of the laboratories of the Southern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.