Synthesis of Phosphazene-Containing Benzoxazine Monomers Based on Bisphenol A and Aniline with Adjustable Functionality

Abstract

The article describes the synthesis of phosphazene-containing benzoxazine monomers with one to three phosphazene components in a mixture with a benzoxazine monomer based on bisphenol A and aniline. The three-stage synthesis consisted of obtaining phenoxychlorocyclotriphosphazenes with different target substitution degrees (tri, tetra, penta) in the first stage, then adding bisphenol A to the resulting mixture of phenoxychlorocyclotriphosphazenes (obtaining a mixture of hydroxyaryloxyphenoxyphosphazenes) and performing Mannich condensation in the final stage of the synthesis by adding aniline and paraformaldehyde to the resulting hydroxyaryloxyphenoxyphosphazenes. Using ³¹P NMR spectroscopy, the substitution reaction time was determined in the synthesis of model systems of phenoxychlorophosphazenes: for triphenoxytrichlorocyclotriphosphazene (triPhChPh), the reaction time was 12 h, for tetraphenoxydich-lorocyclotriphosphazene (tetraPhChPh) was 12 h, for pentaphenoxymonochlorocyclotriphosphazene (pentaPhChPh) was 18 h. The experimental degrees of substitution were compared with the theoretical ones. The composition and chemical structure of the products were confirmed using ¹H, ¹³C, ³¹P NMR spectroscopy, MALDI-TOF mass spectrometry and X-ray fluorescence spectrometry (elemental analysis for P and Cl)

The work was supported by the Russian Science Foundation (grant no. 22-73-10242)

Please cite this article in English as:

Kirianova I.D., Tarasov I.V., Sokolskaya I.B., et al. Synthesis of phosphazene-containing benzoxazine monomers based on bisphenol A and aniline with adjustable functionality. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2026, no. 2 (125), pp. 74--93 (in Russ.). EDN: VUBPHY

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