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Synthesis of a Benzoxazine with Precisely Two Phenolic OH Linkages andthe Properties of Its High-Performance Copolymers

By Ching Hsuan Lin, Yu Ren Feng, Kang Hong Dai, Hou Chien Chang and Tzong Yuan Juang


A phenolic OH-containing benzoxazine (F-ap), whichcannot be directly synthesized from the condensation of bisphenolF, aminophenol, and formaldehyde by traditional procedures,has been successfully prepared in our alternative syntheticapproach. F-ap was prepared by three steps including (a) condensationof 4-aminophenol and 5,5’-methylenebis(2-hydroxybenzaldehyde)(1), (b) reduction of the resulting imine linkage bysodium borohydride, and (c) ring closure condensation by formaldehyde.The key starting material, (1), was prepared from2-hydroxybenzaldehyde and s-trioxane in the presence of sulfuricacid. F-ap is structurally similar to bis(3,4-dihydro-2H-3-phenyl-1,3-benzoxazinyl)methane (F-a, a commercial benzoxazine basedon bisphenol F/aniline/formaldehyde) except for two phenolicOHs. The phenolic OHs can provide reaction sites with epoxyand 1,1’-(methylenedi-p-phenylene)bismaleimide (BMI). Thestructure–property relationships between the thermosets ofF-ap/epoxy, F-a/epoxy, F-ap/BMI, and F-a/BMI were discussed.Experimental data showed that thermosets based on F-ap/epoxyand F-ap/BMI provided much better thermal propertiesthan those based on F-a/epoxy and F-a/BMI

Topics: high performance polymers, synthesis, thermosets
Year: 2014
DOI identifier: 10.1002/pola.26661
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