Preparation, characterization, and polymerization of maleimidobenzoxazine monomers as a novel class of thermosetting resins

Abstract

New series of benzoxazine-based monomers, namely maleimidobenzoxazines, were prepared with hydroxyphenylmaleimide, formalin, and various amines (e.g., aniline, allylamine, and aminophenyl propargyl ether). The structure of the novel monomers was confirmed by IR, 1 H NMR, and elemental analysis. The monomers were easily dissolved in many common organic solvents. Differential scanning calorimetry of the novel monomers showed exotherms at different temperature ranges that corresponded to the polymerization regime of benzoxazine and maleimide along with other functionalities such as allyl or propargyl, if any. IR was studied to follow the progress of the curing reaction of maleimidobenzoxazine after various thermal treatments. The thermal cure of the monomers at 250 8C afforded a novel network structure that combined polybenzoxazine and polymaleimide. The dynamic mechanical analyses showed that the storage moduli of the thermosets derived from maleimidobenzoxazine were kept constant up to high temperatures. The glass-transition temperatures were as high as 241-335 8C. Moreover, thermogravimetric analyses revealed that the thermosets did not show any weight loss up to about 350 8C, with char yields ranging from 62 to 70% at 800 8C.

Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application

“…According to the literature, some work has been done in synthetic aspect of modifying benzoxazines with furan or maleimide chains. So far, the majority of the research was focused on the modified benzoxazines describing effects of maleimide or furan functionality on the mechanical properties of polymeric benzoxazines, while the use of Diels-Alder reaction in self-healing perspective has not yet been recognized [17][18][19][20][21][22]. Needless to say, numerous studies were performed to date dealing with the DA reaction based on maleimide and furan functionalities [6,16,[23][24][25][26][27][28].…”

High Performance Polybenzoxazines as a Novel Type of Phenolic Resin

“…70-130 C and the thermal decomposition temperature by C. New series of benzoxazine-based monomers containing maleimide groups, namely maleimidobenzoxazines, were prepared from the reaction of hydroxyphenylmaleimide, formalin, and various amines (e.g., aniline, allylamine, and aminophenyl propargyl ether) as shown in Figure 8. 8 The monomers were easily dissolved in many common organic solvents. DSC of the novel monomers showed exotherms at different temperature ranges that corresponded to the polymerization of benzoxazine and maleimide along with other functionalities such as allyl or propargyl ( Figure 9).…”

Curing reaction of bisphenol-A based benzoxazine with cyanate ester resin and the properties of the cured thermosetting resin

“…Jang and Seo studied the performance improvement of rubber-modified polybenzoxazine [26]. Recently, maleimide-modified [22][23][27][28] and furan-modified [29] azines have been synthesized, and the properties of the cured resins have been investigated. Nanocomposites using benzoxazines also recently have been reported [30][31][32][33].…”