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, 1H-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