Polycyanurates and Polycarbonates Based on Eugenol: Alternatives to Thermosetting and Thermoplastic Polymers Based on Bisphenol A

Abstract : Polycyanurate thermosetting networks, polycarbonate thermoplastics, and homogenous polycarbonate/polycyanurate network blends have been prepared from a bio-derived bisphenol. The bisphenol was prepared via a solvent-free, ruthenium-catalyzed olefin metathesis coupling reaction of eugenol followed by hydrogenation. The pure polycyanurate network exhibited a glass transition temperature (Tg) of 186 degrees Celsius and a 5% weight loss temperature above 350 degrees Celsius under nitrogen. The pure polycarbonate exhibited a Tg of 71 degrees Celsius, Mn = 8360, and a polydispersity of 1.88. No phase separation was observed in an 80:20 blend of cyanate ester: polycarbonate during or after cure; the resulting homogeneous system showed a single Tg of 132 degrees Celsius. End-group analysis of the polycarbonate provided no evidence of residual phenols, and the polycarbonate fraction was readily extracted from the polycyanurate network, suggesting that no chemical grafting occurred. These new polymer systems represent promising potential alternatives to similar systems derived from Bisphenol A.