Structural Characterization of Hydroxyl-Terminated Polybutadiene-Bound 2, 2-Thiobis(4-methyl-6-tert-butylphenol) and Its Thermo-Oxidative Aging Resistance for Natural Rubber Vulcanizates

Abstract

A novel polymeric antioxidant, hydroxyl-terminated polybutadiene-bound 2,2-thiobis(4-methyl-6-tert-butylphenol) (HTPB-IPDI-TPH), was prepared by binding 2, 2-thiobis(4-methyl-6-tert-butylphenol) (TPH) onto hydroxyl-terminated polybutadiene (HTPB) with isophorone diisocyanate (IPDI). Fourier-transform infrared spectroscopy (FTIR), 13C nuclear magnetic resonance spectroscopy (13C NMR), and gel permeation chromatography (GPC) were used to characterize the structure of HTPB-IPDI-TPH. The thermal stability of HTPB-IPDI-TPH was studied by thermogravimetry analysis (TGA). The effect of HTPB-IPDI-TPH on thermo-oxidative aging resistance of NR vulcanizates was investigated, and the mechanism of thermo-oxidative aging resistance was preliminarily discussed. The results showed that HTPB-IPDI-TPH contributed better thermal stability and thermo-oxidative aging resistance to NR vulcanizates than TPH. The thermo-oxidative aging resistance of HTPB-IPDI-TPH was more remarkable in the later stage of aging. Attenuated total-reflectance Fourier-transform infrared spectroscopy (FTIR-ATR) analysis showed that the relative content of carbonyl groups of NR vulcanizate with HTPB-IPDI-TPH was obviously lower than that with TPH after thermo-oxidative aging. It is suggested that ‒NHCOO‒ groups in HTPB-IPDI-TPH enhanced the ability of trapping alkyl peroxide radicals.