The bulk and solution reactions between N-Phenylmaleimide (PMI) and Aniline (AN) were carried out as a model reaction for the synthesis of amine-modified maleimide resin. In the bulk system, N, N'-diphenylaspartimide (API) is produced by Michael addition reaction between PMI and AN at a lower temperature (100°C). By-product such as fumardianilide is obtained at a higher temperature more than 100°C. N-pheny-aspartdianilide is supposed to be obtained at a higher temperature or by increasing AN content.
In N, N-dimethylformamide which is an aprotic solvent, both API and PMI oligomers are obtained. In a protic solvent such as acetic acid (AcOH), m-cresol (m-CR) or methylcellosolve (MCS), only API is obtained. The reaction rate becomes faster (AcOH>m-CR>MCS) by lowering PKa of solvent.
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