Synthesis and Properties of Quinoxaline-Containing Benzoxazines and Polybenzoxazines

Chien Han Chen; Tsung Yen Yu; Jen-Hao Wu; Mathivathanan Ariraman; Tzong-Yuan Juang; Mahdi M Abu-Omar; Ching-Hsuan Lin

doi:10.1021/acsomega.9b01042

Synthesis and Properties of Quinoxaline-Containing Benzoxazines and Polybenzoxazines

ACS Omega. 2019 May 23;4(5):9092-9101. doi: 10.1021/acsomega.9b01042. eCollection 2019 May 31.

Authors

Chien Han Chen¹, Tsung Yen Yu², Jen-Hao Wu³, Mathivathanan Ariraman², Tzong-Yuan Juang³, Mahdi M Abu-Omar⁴, Ching-Hsuan Lin^{1

2}

Affiliations

¹ Advanced Research Center for Green Materials Science and Technology, National Taiwan University, Taipei 10617, Taiwan.
² Department of Chemical Engineering, National Chung Hsing University, Taichung 402, Taiwan.
³ Department of Cosmeceutics and School of Pharmacy, China Medical University, Taichung 404, Taiwan.
⁴ Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, California 93106, United States.

Abstract

The object of this work is to prepare quinoxaline-based benzoxazines and evaluate thermal properties of their thermosets. For this object, 4,4'-(quinoxaline-2,3-diyl)diphenol (QDP)/furfurylamine-based benzoxazine (QDP-fu) and 4,4',4″,4‴-([6,6'-biquinoxaline]-2,2',3,3'-tetrayl)tetraphenol (BQTP)/furfurylamine-based benzoxazine (BQTP-fu) were prepared. The structures of QDP-fu and BQTP-fu were successfully confirmed by FTIR and ¹H and ¹³C NMR spectra. We studied the curing behavior of QDP-fu and BQTP-fu and thermal properties of their thermosets. According to DSC thermograms, QDP-fu and BQTP-fu have the attractive onset exothermic temperatures of 181 and 186 °C, respectively. The onset temperature is approximately 45 °C lower than that of a bisphenol A/furfurylamine-based benzoxazines. According to DMA TMA and TGA thermograms, the thermoset of BQTP-fu shows impressive thermal properties, with a T _g value of 418 °C, a coefficient of thermal expansion of 39 ppm/°C, a 5% decomposition temperature of 430 °C, and a char yield of 72%.