Synthesis and characterization of maleated glycidyl 3‐pentadecenyl phenyl ether as a functionalized plasticizer for styrene–butadiene rubber/carbon black/silica composites

Abstract

ABSTRACTMaleated glycidyl 3‐pentadecenyl phenyl ether (M‐GPPE) was synthesized from glycidyl 3‐pentadecenyl phenyl ether (GPPE), a renewable derivative from cardanol, with maleic anhydride (MAH) by grafting copolymerization. The resulting M‐GPPE was used as a functionalized plasticizer for a styrene–butadiene rubber (SBR)/carbon black (CB)/silica composite. The effects of M‐GPPE on the development of the filler network, the extent of silica dispersion, the curing characteristics, and the mechanical performance of the composites were studied. Meanwhile, a comparative study was performed between M‐GPPE and aromatic oil, a traditional plasticizer used in SBR filler formulations. Gel permeation chromatography and IR and 1H‐NMR analysis results confirmed the occurrence of the grafting reaction between GPPE and MAH and the potential structure of M‐GPPE. The thermostability of GPPE was improved by grafting copolymerization with MAH, as shown by thermogravimetric analysis results. The presence of M‐GPPE resulted in a shorter curing time and better aging properties in the SBR composite compared with GPPE. The mechanical properties, dynamic mechanical analysis, and transmission electron microscopy analysis showed that the maleate of GPPE could enhance the compatibility between SBR and silica, improve the dispersion of silica in SBR, and partially replace the aromatic oil in the SBR/CB/silica composite formulation. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40462.