New polymerizable derivatives of high aspect ratio bisphenol A analogues: Synthesis and characterization

ORGN 84

Josiah T. Reams, josiahreams@yahoo.com, Department of Chemistry and Chemical Engineering, South Dakota Schoolof Mines and Technology, 501 East Saint Joseph Street, Rapid City, SD 57701
We have synthesized three new compounds based on well-known bisphenol A derivatives, the latter of which have a variety of commercial uses, particularly for resins. Unlike the bisphenol A derivatives themselves, these new compounds contain four aryl rings and have a greater length-to-width ratio which may provide for interesting effects on both the properties and performance of resins of polymers made from. The tetraaryl compound itself was synthesized by an expeditious Suzuki reaction in good overall yield. A one step synthesis from 2,2-bis-(4-(4'-hydroxyphenyl)phenyl)propane (“tetraaryl bisphenol A--TABPA”) yielded difunctionalized monomers for subsequent reaction. They include 2,2-bis-(4-(4'- glycidyloxyphenyl)phenyl)propane (TABPA diglycidyl ether), 2,2-bis-(4-(4'- methacryloxy)phenyl)propane (TABPA dimethacrylate), and 2,2-bis-(4-(4'-cyanatophenyl)phenyl)propane (TABPA dicyanate). These monomers were characterized by nuclear magnetic resonance and infrared spectroscopy, confirming their identity. Reactions of these materials were performed to compare the products with those of known resins and polymers prepared from bisphenol A analogues. Glass transition temperatures and infrared spectra of the materials are discussed.