Issue 91, 2015

Strategy to prepare 4-hydroxylphenyl propargyl ether-based benzoxazine from bisphenol A

Abstract

4-Aminophenyl propargyl ether/phenol-based benzoxazine (P-appe) has been reported by many authors. However, to the best of our knowledge, its isomer: 4-hydroxylphenyl propargyl ether/aniline-based benzoxazine (HPPE-a) has never been prepared in the literature. The precursor for HPPE-a, the 4-hydroxylphenyl propargyl ether, is difficult to prepare from hydroquinone without tedious separation because the reactivity of the two hydroxyls in hydroquinone is the same. In this study, we report a straightforward strategy to prepare HPPE-a from bisphenol A by a four-step process including thermolysis, nucleophilic substitution, oxidation, and Mannich-type condensation. The structure was well characterized by NMR, IR, and high resolution mass spectra. Two exothermic peaks at 228 °C and 249 °C were observed in the DSC thermogram of HPPE-a. According to IR analysis, the first exotherm is related with the ring opening of the oxazine, and the second exotherm is related with Claisen rearrangement of propargyl ether. Since P-appe and HPPE-a are structural isomers, the structure–property relationship of these two benzoxazines was discussed. We found that the thermal properties of a thermoset of HPPE-a are slightly lower or comparable to those of a thermoset of P-appe, but much higher than that of phenol/aniline-based benzoxazine (P-a).

Graphical abstract: Strategy to prepare 4-hydroxylphenyl propargyl ether-based benzoxazine from bisphenol A

Article information

Article type
Paper
Submitted
13 Jul 2015
Accepted
26 Aug 2015
First published
26 Aug 2015

RSC Adv., 2015,5, 74874-74880

Author version available

Strategy to prepare 4-hydroxylphenyl propargyl ether-based benzoxazine from bisphenol A

C. C. Huang, C. H. Lin and S. A. Dai, RSC Adv., 2015, 5, 74874 DOI: 10.1039/C5RA13743H

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