Abstract
In this work, a novel bonded primary-secondary antioxidant named as MBC was synthesized successfully via thiol-ene addition reaction of primary antioxidant N-(4-anilino phenyl) maleic imide (MC) with secondary antioxidant 2-mercaptobenzimidazole (MB). Then, the antioxidation behavior of MBC in styrene-butadiene rubber (SBR) matrix was systematically investigated using experiments and molecular simulation. The results showed that MBC diminishes the negative impact of MC on the cross-linking density of SBR composite. MBC presented better dispersion and lower migration than MC in the SBR matrix. Furthermore, MBC containing aromatic amino and thioether groups not only capture peroxy radical but also decompose hydroperoxide. Hence, compared with MB/SBR or MB/MC/SBR composite, MBC/SBR composite exhibited outstanding mechanical properties and good thermo-oxidative stabilization during the aging process, indicating that MBC could be a promising antioxidant for the preparation of high-performance SBR composite. Moreover, molecular simulation can provide deeper insights for designing the molecule structure of effective antioxidants.
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