Replacement of bisphenol A (BPA) due to its potential as an endocrine disruptor is an important challenge for the chemical industry. Epoxy resins account for about 70% of the thermoset polymer market with a large portion being based on BPA. Cumene is derived from steam cracking of petroleum and is the starting material for production of BPA.Levulinic acid is a biobased monomer derived from the degradation of cellulose. The US Department of Energy cited levulinic acid as one of the �Top Value Added Chemicals from Biomass,� due to its feasibility of production and ability to be converted into a broad variety of chemicals. A condensation of levulinic acid with phenol yields diphenolic acid, a potential replacement of BPA for use in polycarbonates and epoxy resins.Herein we report the synthesis of biobased epoxy monomers from esters of diphenolic acid. Similar synthetic conditions pioneered by Shell and Dow were used to produce the biobased epoxy monomers in order to show compatibility with existing processes allowing for a potential drop-in replacement. The diglycidal ethers of diphenolic esters (DGEDPE) were cured utilizing isophorone diamine (IPDA), a widely used industrial hardener of epoxy resins. The results obtained were compared to the diglycidal ether of bisphenol A (DGEBA) under similar curing conditions. Evaluations of the thermal and mechanical properties of these two systems were performed using dynamic mechanical analysis and tensile testing. We found that DGEDPE has similar mechanical and thermal properties as DGEBA. The thermal and mechanical properties of DGEDPE can be controlled through manipulation of the ester. Further investigations are being conducted to confirm if this monomer can replace DGEBA for structural applications.

Biobased replacements of bisphenol A epoxy resins

248th National Meeting (2014)

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