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Phenolic antioxidants based on calixarene: Synthesis, structural characterization, and antioxidative properties in natural rubber
Author(s) -
Li Hongqiang,
Zhong Yong,
Wu Wenjian,
Zhang Lin,
Lai Xuejun,
Zeng Xingrong
Publication year - 2017
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.45144
Subject(s) - chemistry , biochemistry , polymer chemistry , stereochemistry
C‐methylcalix[4]resorcinarene (CMCR) was first synthesized by condensation reaction between resorcinol and acetaldehyde, and then used as functional monomer to prepare two CMCR derivatives including CMCR‐1 and CMCR‐2 with four ethoxymethyl chains and four hexylthiolmethyl chains, respectively. The structures of CMCR and its derivatives were confirmed by Fourier transform infrared spectroscopy and high‐resolution mass spectrometry. Thermogravimetric analysis revealed CMCR, CMCR‐1, and CMCR‐2 had superior thermal stability than commercial antioxidant 2,6‐di‐ tert ‐butyl‐4‐methylphenol. Oxidation induction time and accelerated thermal aging tests indicated that CMCR‐2 exhibited excellent antioxidative property in natural rubber, which was due to multiphenol groups, big steric hindrance, and synergistic effect between thiother and hindered phenol. Importantly, CMCR‐2 also possessed outstanding extraction resistance. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 45144.