Synthesis and diels–alder polymerization of furfurylidene and furfuryl‐substituted maleamic acids
- 1 January 1992
- journal article
- research article
- Published by Wiley in Journal of Polymer Science Part A: Polymer Chemistry
- Vol. 30 (1) , 125-132
- https://doi.org/10.1002/pola.1992.080300116
Abstract
The reactions of monomaleamic acid derived from an aromatic diamine with furfural afforded a novel class of furfurylidene‐substituted maleamic acids 2a–2d. The latter were cyclodehydrated to yield maleimides 3a–3d which are AB‐monomers for a Diels–Alder polymerization. In addition, N‐furfurylmaleamic acid (4) was synthesized by reacting furfurylamine with maleic anhydride at ambient temperature. Cyclodehydration of 4 afforded N‐furfurylmaleimide (5). The polymer precursors were characterized by IR and 1H‐NMR spectroscopy. Their curing behavior was investigated by DTA and correlated with chemical structures. Diels–Alder polymerization of monomers occurred at the temperature range of 113–210°C. Thermal stability of monomers was evaluated by TGA and isothermal gravimetric analysis (IGA). It was shown that thermal stability of the polymer derived from maleamic acid 4 was dramatically improved upon curing at high temperatures due to the formation by dehydration of a stable aromatic structure.Keywords
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