Synthesis of Cyanate Esters Based on Mono-O-Methylated Bisphenols with Sulfur-Containing Bridges

Abstract

We described a synthetic approach to bisphenol-based monocyanate esters based on mono-O-methylation of parental bisphenols followed by cyanation of the residual phenolic hydroxyl. Structures of the synthesized compounds were determined by the application of IR, NMR 1H and 13C spectroscopies, EI and MALDI mass spectrometry, and purity of the final product was controlled by HPLC. We showed that stability of the cyanate esters depends on the nature of the bridging group. Temperature range of thermally initiated cyclotrimerization of synthesized monocyanate ester, as well as reaction enthalpy, was determined by differential scanning calorimetry (DSC).

Keywords

• cyanate esters
• aryl cyanates
• cyanate resins
• curing
• bisphenols
• Mitsunobu reaction
• thermal analysis