Reactions of 2-t-Butylbenzothiazole Sulfenamide with Sulfur and Zinc Oxide in the Absence of Rubber

Abstract

Abstract The interaction of sulfur, ZnO and 2-t-butylbenzothiazole sulfenamide (TBBS) was investigated by differential scanning calorimetry (DSC) in the absence of rubber. Special reference was made to the role of the amine, the distinguishing characteristic of all sulfenamides. TBBS decomposes rapidly at 211 °C, the major products being 2-bisbenzothiazole-2,2′-disulfide (MBTS) and 2-bisbenzothiazole-2,2′-monosulfide (MBTM). High mass losses occured and very little free amine was found at these high temperatures. The major degradation products of the TBBS/sulfur system were MBTS, 2-bisbenzothiazole-2,2′-polysulfides (MBTP) and 2-t-butylaminobenzothiazole polysulfides (TBBP). Little free amine and very small mass losses were found. Reaction mechanisms were proposed to account for the formation of the products.