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標題: Benzoxazines with tolyl, p-hydroxyphenyl or p-carboxyphenyl linkage and the structure-property relationship of resulting thermosets
作者: Lin, C.H.
Lin, H.T.
Chang, S.L.
Hwang, H.J.
Hu, Y.M.
Taso, Y.R.
Su, W.C.
關鍵字: Benzoxazine;Flame retardancy;Thermoset;epoxy-resins;thermal-decomposition;phenolic resins;polybenzoxazines;phosphorus;maleimide;polymers;monomers
Project: Polymer
期刊/報告no:: Polymer, Volume 50, Issue 10, Page(s) 2264-2272.
Three benzoxazines (7-9) with a tolyl, p-hydroxyphenyl or p-carboxyphenyl structure, respectively, were successfully synthesized by a three-pot or two-pot procedure. In the three-pot approach, the first step is the condensation of 2-hydroxybenzaldehyde with p-toluidine, 4-aminophenol and 4-aminobenzoic acid, respectively, forming intermediates (1-3) with an imine linkage. The second step is the addition of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO) on the imine linkage, resulting in intermediates (4-6) with a secondary amine linkage. The last step is the ring closure condensation of(4-6), leading to benzoxazines (7-9). In the simplified two-pot approach, the first two steps-the condensation and imine reduction were carried out in one reactor, so the yield of(4-6) was increased. The structures of monomers (1-9) were characterized and confirmed by 1 D and 2D NMR spectra. The synthesized benzoxazines were thermally self-cured or copolymerized with a commercial benzoxazine, bis(3-phenyl-3,4-dihydro-2H-benzo[e][1,3]oxazin-6-yl)methane (F-a). IR analysis was utilized to monitor the ring-opening reaction of (7-9) and to propose the structures of p(7-9). The microstructure and the structure-property relationship of the resulting homopolymers and copolymers are studied. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN: 0032-3861
DOI: 10.1016/j.polymer.2009.02.042
Appears in Collections:化學工程學系所

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