Synthesis of a novel series of propargyloxyphenyl maleimides and their characterization as thermal‐resistance resins

Novel thermosetting monomers possessing both maleimide and propargyl groups were first designed and synthesized. The monomers included N ‐(2‐propargyloxyphenyl) maleimide (2‐PPM), N ‐(3‐propargyloxyphenyl) maleimide (3‐PPM), and N ‐(4‐propargyloxyphenyl) maleimide (4‐PPM), and their structures were confirmed with Fourier transform infrared (FTIR) spectroscopy, 1 H‐NMR, and elemental analysis. The cure behaviors of these monomers were characterized with differential scanning calorimetry and FTIR spectroscopy, and the results indicated that the monomers had a broader processing window than normal bismaleimide (BMI) resins. The thermal properties of the cured monomers were characterized with thermogravimetric analysis and dynamic mechanical analysis. The 5% mass loss temperatures of the cured monomers were high (ca. 400°C), and the glass‐transition temperatures of cured 2‐PPM, 3‐PPM, and 4‐PPM were 386, 373, and 387°C, respectively, which were much higher than those of typical commercial blended BMI resins. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010