(191e) Vanillyl Alcohol: A Renewable Epoxy Resin Building Block

Polymers derived from renewable resources are becoming considerably attractive as sustainable alternatives to their petroleum-derived counterparts.  Lignin is a natural and abundant raw material made up of cross-linked aromatics that could potentially be broken down to yield renewable bio-based monomers and resins for applications in high-performance thermosets and composites.  In this work, vanillyl alcohol was utilized as a promising lignin-based building block for the synthesis of epoxy monomers and resins.  Specifically, diglycyl ether of vanillyl alcohol (DGEVA) was synthesized and its chemical structure was confirmed by ¹H-NMR, ¹³C-NMR, FT-IR, and GPC.  Bimodal resin blends of diglycidyl ether of bisphenol A (DGEBA) with varying weight ratios of DGEVA as well as bimodal resins blends of DGEBA with other single aromatic epoxies, diglycidyl ether of hydroquinone and diglyical ether of 4-hydroxymethyl phenol, were prepared and cured with a standard diamine, methylenebis(cyclohexylamine), to investigate their processing-structure-property relationships.  Additionally, DGEVA was blended and cured with a (hemi)cellulose-based diamine to investigate the viability of a highly bio-based cured epoxy resin.  We present the thermogravimetric and thermomechanical properties as well as the extents of cure that were obtained and analyzed to gain insight into the behavior of the cured resins.  Moreover, we present green chemistry metrics results of the renewable epoxy resin systems.