Synthesis and properties of a bisphenol A based phthalonitrile resin

Abstract A multiple aromatic ether linked phthalonitrile was synthesized and characterized. The oligomeric phthalonitrile monomer was prepared from the reaction of an excess amount of bisphenol A with 4,4′‐difluorobenzophenone in the presence of K 2 CO 3 as the base in an N,N ‐dimethylformamide/toluene solvent mixture, followed by end capping with 4‐nitrophthalonitrile in a two‐step, one‐pot reaction. The monomer properties were compared to those of the known resin 2,2‐bis[4‐(3,4‐dicyanophenoxy)phenyl]propane after being cured in the presence of bis[4‐(4‐aminophenoxy)phenyl]sulfone. Rheometric measurements and thermogravimetric analysis showed that the oligomeric phthalonitrile resin maintained good structural integrity upon heating to elevated temperatures and exhibited excellent thermal properties along with long‐term oxidative stability. The ether‐linked phthalonitrile resin absorbed less than 2.5% water by weight after exposure to an aqueous environment for extended periods. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 4136–4143, 2005