Synthesis and characterization of adamantane-containing poly(enaminonitriles)

Abstract

The first aliphatic bis(chlorovinylidene cyanide) monomer, 1,3-bis(1-chloro-2,2-dicyanovinyl)adamantane, has been synthesized and polymerized with appropriate diamines to give adamantane-containing aromatic-aliphatic and all aliphatic poly(enaminonitriles) (PEANs) via vinylic nucleophilic substitution polymerization. The PEANs showed excellent solubility in polar aprotic solvents and good thermal stability (10% weight loss in air > 320 °C), despite the aliphatic contents of the polymers. Solution inherent viscosities of 0.23–0.90 dL/g were obtained. Three other new PEANs containing the adamantane-based cardo group were also synthesized via vinylic nucleophilic substitution polymerization from the adamanaine-containing cardo diamine 2,2-bis[4-(4-aminophenoxy)phenyl]adamantane. The cardo PEANs showed better solubility in common organic solvents than the corresponding cardo polyamides. They also showed good thermal stabilities (10% weight loss in air > 339 °C) comparable to those of the corresponding cardo polyamides.