Abstract
To address the disadvantages of traditional rubber antioxidants with low molecular weight such as easy migration, poor extraction resistance, low thermal stability and antioxidant efficiency, in this work, we first prepared an antioxidant containing primary and secondary antioxidant groups (MC-MPA) through thiol-ene click reaction between N-(4-aminophenyl)maleimide (MC) and 3-mercaptopropionic acid (MPA). Then, we synthesized a chitosan-based macromolecular antioxidant with long-chain alkene, aromatic secondary amine, and thioether groups (COS-UC-MC-MPA) by sequentially grafting functional compounds 10-undecanonyl chloride (UC) and antioxidant MC-MPA onto natural macromolecular polymer chitosan (COS). The free radical scavenging ability of COS-UC-MC-MPA was assessed by using 2,2-Diphenyl-1-picrylhydrazyl (DPPH), and the results demonstrated that COS-OC-MC-MPA has high scavenging rate of 76.5% for DPPH free radicals after 1 min of contact with DPPH dimethyl sulfoxide solution, showing excellent free radical scavenging ability. In addition, the results of accelerated thermo-oxidative aging test, thermogravimetric (TG) test, kinetic analysis of thermal-oxidative degradation, extraction resistance test, and volatilization resistance test indicated that COS-UC-MC-MPA with superior migration resistance and volatilization resistance could effectively enhance the antioxidative properties, thermal stability and thermal-oxidative stability of rubber composites. Moreover, the results of rubber processibility analysis (RPA) test and scanning electron microscopy (SEM) implied that the addition of COS-UC-MC-MPA is also conductive to improving the dispersibility of silica in rubber matrix. This study supplies a new perspective for the preparation of environmentally friendly and highly efficient macromolecular antioxidants for rubber composites.
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