Synthesis and thermal properties of a novel high temperature alkyl-center-trisphenolic-based phthalonitrile polymer

A novel alkyl-center-trisphenolic-based high-temperature phthalonitrile monomer, namely, 1,1,1-tris-[4-(3,4-dicyanophenoxy)phenyl]ethane (TDPE), was synthesized from 1,1,1-tris-(4-hydroxyphenyl)ethane (THPE) via a facile nucleophilic displacement of a nitro-substituent from 4-nitrophthalonitrile (NPN). The structure of TDPE monomer was characterized by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (1H and 13C NMR), elemental analysis (EA). Curing behaviors of TDPE with 4-(aminophenoxy)phthalonitrile (APPH) were recorded by differential scanning calorimetric (DSC) and it showed a large processing window (122 °C) which is favorable to processing TDPE polymers. The structure of TDPE polymer was discussed and the thermal stabilities of TDPE polymer were evaluated by thermogravimetric analysis (TGA). The TDPE polymer exhibits excellent thermal stability, and mechanism of thermal decompositions was explored. Dynamic mechanical analysis (DMA) revealed that the TDPE polymer has high storage modulus and high glass transition temperature (Tg > 380 °C).