Environmental and health consciousness have propelled the advancement of biobased materials. Over the past few decades, polymers developed from sustainable resources have been deemed a viable alternative to their petrochemical analogs. For example, thermosets of isosorbide methacrylate, which is derived from glucose, displayed the highest ever glass transition temperature of a vinyl ester resin while containing a strikingly low viscosity as a polymerized resin. It is often the case that natural monomers contain unique substitution patterns which differ from there petrochemical analogs. Flavones are one such class of naturally abundant compounds whose aromatic substitution and core fused rings can offer structural integrity affording a stiff, highly crosslinked rigid polymeric material. Tri and di substituted methacrylates of flavone derivatives were synthesized, thermally and photocured in the presence of reactive diluent, acryloylmorpholine and styrene. Reactivity ratios were investigated in efforts to ascertain optimal cure conditions. Dynamic mechanical analysis was used to measure the glass transition temperatures and modulus of the cured resins.  Glass transition temperatures ranged from 170-200°C, depending on the formulation and moduli ranged from 3.1 GPa to 3.6 GPa.  Flory-Fox analysis was utilized to ascertain the glass transition temperature of the neat flavone resin, indicating a value of ~300°C.  Char content was high for these resins, at about 25%, which corresponds to carbonized structure of the bicyclic ring in the flavones used.

Novel bio-based methacrylate resins based on flavones

2019 Spring National Meeting

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