A Pyridazine-Containing Phthalonitrile Resin for Heat-Resistant and Flame-Retardant Polymer Materials

Abstract

In this study, a novel phthalonitrile monomer containing a pyridazine ring, 3,6-bis[3-(3,4-dicyanophenoxy)phenoxy]pyridazine (BCPD) with a low melting point (74 °C) and wide processing window (178 °C), was prepared by a nucleophilic substitution reaction. The molecular structure of the BCPD monomer was identified by Fourier transform infrared spectroscopy (FTIR), and nuclear magnetic resonance spectroscopy (NMR). Poly(BCPD) resins were derived from the formulations by curing at 350 and 370 °C. The thermoset that was post-cured at 370 °C demonstrated outstanding high heat-resistant (glass transition temperature (Tg) > 400 °C, 5% weight loss temperature (T5%) = 501 °C, Yc at 900 °C > 74%) and was flame-retardant (limiting oxygen index (LOI) = 48)). Further, the poly(BCPD) resin simultaneously exhibited a superior storage modulus, which could reach up to 3.8 Gpa at room temperature. Excellent processability and heat resistance were found for phthalonitrile thermosets containing the pyridazine ring, indicating poly(BCPD) resin could be potentially applied as high-temperature structural composite matrices.