Maleimidobenzoxazines are compounds containing benzoxazine and maleimide moiety in one molecule. Due to their relatively high glass transition temperatures (200 to 350 °C) and superior thermal stability they are classified as high performance materials. Currently, such materials are prepared from a common phenolic template based on 4-hydroxyphenylmaleimide (HPMI) leading to the lack of phenolic diversity in the maleimidobenzoxazine molecule. In general, diversity in benzoxazines originates from the side groups of phenolic and amine/aniline moieties, which reacted together in the presence of formaldehyde or paraformaldehyde under solvent or solventless conditions (Fig. 1). Alternative approach towards preparation of maleimidobenzoxazines, which significantly broadens the scope in maleimidobenzoxazine chemistry is presented. Four step maleimide modification of 4,4-diaminodiphenylmethane (DDM) furnished aminomaleimide type of molecule, which was further reacted with phenol, 4-tert-butylphenol and bisphenol A. All of the obtained products where classified as maleimidobenzoxazines, in which diversification originated from the phenolic part of the molecule. Obtained maleimidobenzoxazines were characterized by 1H and 13C NMR, FTIR, DSC analysis. Further analysis of cured samples displayed high glass transition temperatures and good thermal stability, therefore confirming reputation as high performance materials.

Alternative approach in preparation of the maleimidobenzoxazines

255th National Meeting (2018)

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