Innovative approach using aminomaleimide for unlocking phenolic diversity in high-performance maleimidobenzoxazine resins

Publication date: 30 June 2017
Source:Polymer, Volume 120
Author(s): Žiga Štirn, Aleš Ručigaj, Matjaž Krajnc
A new innovative synthetic approach for the preparation of maleimidobenzoxazines was developed. For the first time the phenolic diversity in maleimidobenzoxazine compounds was enabled, opening many possibilities for tailoring properties of maleimidobenzoxazines through phenolic diversity. The key in a successful implementation of a novel synthetic approach was utilization of aminomaleimide compound prepared by modified synthetic path, without the need for chromatographic purification. Yields of the reaction between aminomaleimide and phenols reached up to 95%, which is a significant improvement prior to previous studies dealing with maleimidobenzoxazines. Aminomaleimide and all novel maleimidobenzoxazine substances were characterized by ¹H NMR, ¹³C NMR and FTIR spectroscopies. The curing behaviour of prepared maleimidobenzoxazines was investigated by DSC analysis and mechanical properties by DMA analysis. Novel maleimidobenzoxazines showed similar properties comparing to the already presented in the literature showing high glass transition temperature values over 240 °C. Thermogravimetric analysis proved improved thermal stability of maleimidobenzoxazines compared to anilinobenzoxazines. Finally, the use of prepared maleimidobenzoxazines was investigated by the means of Diels-Alder reaction as a possible benzoxazine bearing maleimide group precursor for self-healing purposes.

Graphical abstract

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