The rubber antioxidant N-(4-anilinophenyl) methacrylamide (NAPM) was synthesized by a two-step reaction using thionyl chloride (SOCl2) with methacrylic acid (MAA) and consequently 4-aminodiphenylamine (ADPA) as precursors. NAPM was characterized by IR, H-1 NMR and elemental analysis. Thermal stability, aging property of NAPM and mechanical properties of natural rubber (NR) vulcanizates containing NAPM were investigated and compared with two other commercial antioxidants N-isopropyl-N'-phenyl-p-phenylene diamide (4010NA) and N-(1, 3-dimethyl butyl)-N'-phenyl-p-pheny1ene diamide (4020). It was found that NAPM was an effective antioxidant with a better thermal stability and higher antiaging resistance than unreactive antioxidants 4010NA and 4020. And unsaturation level of NR vulcanizates containing NAPM was lower than that of 4010NA and 4020. Moreover, an antiaging resistant mechanism of a surface reaction between NAPM and cis-1, 4-polyisoprene in NR was proposed to explain the better properties of NAPM based on the IR and SEM analyses. (C) 2008 Wiley Periodicals, Inc.