Synthesis and thermal properties of bismaleimides with mesogen aromatic amide–ester and flexible polymethylenic group

Abstract

AbstractFour bismaleimides with mesogen “amide–ester” aromatic and flexible polymethylenic group variable length (8 ≤ n ≤ 11) were synthesized in two stages, producing yields exceeding 80%. These bismaleimides (BMIs) were obtained after several purifications by dissolution—precipitation in dimethylformamide–methanol (1/4) with over 94% purity (high‐performance liquid chromatography). These pure BMIs were characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy, and elemental analysis and studied by differential scanning calorimetry, thermogravimetric analysis, polarized light microscopy, and X‐ray diffraction. Solubilities and thermal properties show effects of parity. The even BMIs are more difficult to solubilize than the odd BMI. The melting points of the even BMI (approximately, 220°C) are far higher than those of odd BMI (approximately, 160°C). Crosslinking temperatures of even BMI are close to 230°C, whereas odd BMI crosslinking temperatures are higher (approximately, 250°C). Even BMIs give rise to a liquid crystal state upon melting. Under the same conditions, odd BMIs give rise to an amorphous state; however, after crosslinking, the four bismaleimides give rise to an ordered liquid crystal state of smectic type. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013