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Open AccessArticle

Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening

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State Key Laboratory of Polymer Materials Engineering, Polymer Research Institute of Sichuan University, Chengdu 610065, China
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Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, OH 44106-7202, USA
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Design and Chemistry of Macromolecules Group, Institute of Technology in Polymers and Nanotechnology (ITPN), UBA-CONICET, FADU, University of Buenos Aires, Intendente Güiraldes s/n, Pabellon III, subsuelo, Ciudad Universitaria (P.C. C1428EGA), Buenos Aires C1428EGA, Argentina
*
Author to whom correspondence should be addressed.
Polymers 2020, 12(3), 694; https://doi.org/10.3390/polym12030694
Received: 23 January 2020 / Revised: 7 March 2020 / Accepted: 10 March 2020 / Published: 20 March 2020
In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-((phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis. View Full-Text
Keywords: 2-substituted 1,3-benzoxazine; ring opening; HCl hydrolysis 2-substituted 1,3-benzoxazine; ring opening; HCl hydrolysis
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MDPI and ACS Style

Cui, S.; Arza, C.R.; Froimowicz, P.; Ishida, H. Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening. Polymers 2020, 12, 694.

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