Polymerization behaviors of benzoxazine isomers based-on meta-substituted phenols

The polymerization activity of benzoxazine is closely related to its molecular structure. In this work, two meta-substituted phenols, including 3-methoxyphenol and 3-chlorophenol, were separately reacted with aniline and paraformaldehyde, and two pairs of benzoxazine isomers were successfully synthe...

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Bibliographic Details
Published in:Thermochimica acta 2023-10, Vol.728, p.179587, Article 179587
Main Authors: Ren, Shitong, Tian, Fangjing, Wu, Aiyan, Feng, Jiahao, Teng, Yujun, Liu, Qing, Du, Yonggang
Format: Article
Language:English
Subjects:
Benzoxazine isomers
Meta-substituent
Molecular simulation
Polymerization behavior
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Summary:The polymerization activity of benzoxazine is closely related to its molecular structure. In this work, two meta-substituted phenols, including 3-methoxyphenol and 3-chlorophenol, were separately reacted with aniline and paraformaldehyde, and two pairs of benzoxazine isomers were successfully synthesized. Their structures were confirmed by nuclear magnetic resonance (NMR) and Fourier-transform infrared (FT-IR) spectroscopy. The polymerization behaviors of the isomers were investigated by differential scanning calorimetry (DSC). The results indicated that 7-position benzoxazine isomers exhibited higher polymerization activity over 5-position isomers. The charges populations and CO bond lengths of the isomers calculated by molecular simulation well supported the results of experiment. This work provided new clues for developing novel benzoxazines with low polymerization temperatures. [Display omitted]
ISSN:0040-6031
1872-762X
DOI:10.1016/j.tca.2023.179587