N-(Aminothio)imide Cure Modifiers

Abstract

Abstract N-(Aminothio)imides have been found to influence the cure characteristics of diene rubbers accelerated by conventional vulcanization accelerators. In this respect, they generally act both as scorch inhibitors and activators to increase the cure rate and crosslink density. The ability of these compounds to act as scorch inhibitors is believed to be attributable to trapping of MBT with resultant formation of the corresponding free imide and 2-(aminodithio)benzothiazole. The latter is an active vulcanization agent and may lead directly to the formation of pendent accelerator groups and free amine, likely the source of the cure activation. As precursors to crosslink formation, the pendent accelerator groups carry an atom of sulfur derived from the cure modifier and thus lead to higher crosslink density. The relative scorch inhibiting characteristics are influenced by the basicity of the parent amine and thermal stability of the cure modifier. The compounds derived from amines of weaker basicity are better retarders and less subject to thermal degradation which would lead to nonretarding products. The relative cure activating effects are apparently influenced by both steric and electronic effects of the parent amine. Cure activation increases as the steric bulk decreases and basicity increases. As expected, the nature of the imide substituent played a relative insignificant role in influencing the cure characteristics, aside from a possible stabilization against thermal degradation.