<p>Fully renewable epoxy resin polymers were synthesized from epoxidized vegetable oils via a two-step epoxidation and ring opening polymerization sequence. Biobased 2,5-furandicarboxylic acid (FDCA) was utilized as the crosslinker due to its aromatic structure and the anticipated positive impacts on tensile and viscoelastic properties. In situ differential scanning calorimetry revealed that 1.0 wt% 1-methylimidazole was the most effective of the five hindered amine curing catalysts screened. Polymerizations were conducted at 150&#xa0;°C for two hours at a molar ratio of acids to epoxides of 1.1:1 utilizing a simple compression molding procedure. Tensile and viscoelastic properties correlated with average oxirane content of the epoxidized oil, with epoxidized linseed oil-based polymers yielding the highest storage modulus (560.1&#xa0;MPa), glass transition temperature (72.0&#xa0;°C), crosslink density (710&#xa0;mol/m<sup>3</sup>), Young’s modulus (312&#xa0;MPa), and tensile strength at break (21.9&#xa0;MPa), but the lowest elongation at break (8.6%) versus materials prepared from epoxidized field pennycress, hempseed, and soybean oils. In contrast, pennycress-based polymers were the weakest but most ductile owing to the lower average oxirane content and longer fatty acid chain length of epoxidized pennycress oil. Lastly, chemical degradation studies demonstrated nearly complete hydrolysis under alkaline conditions, highlighting the potential of these materials as cleavable biobased epoxy networks for sustainable applications where high flexibility, low mechanical strength, and end-of-life degradability are advantageous.</p>

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Renewable Polymers from Epoxidized Vegetable Oils and 2,5-Furandicarboxylic Acid

  • Bryan R. Moser,
  • Kadisha M. Culpepper,
  • Nathaniel I. Dexter

摘要

Fully renewable epoxy resin polymers were synthesized from epoxidized vegetable oils via a two-step epoxidation and ring opening polymerization sequence. Biobased 2,5-furandicarboxylic acid (FDCA) was utilized as the crosslinker due to its aromatic structure and the anticipated positive impacts on tensile and viscoelastic properties. In situ differential scanning calorimetry revealed that 1.0 wt% 1-methylimidazole was the most effective of the five hindered amine curing catalysts screened. Polymerizations were conducted at 150 °C for two hours at a molar ratio of acids to epoxides of 1.1:1 utilizing a simple compression molding procedure. Tensile and viscoelastic properties correlated with average oxirane content of the epoxidized oil, with epoxidized linseed oil-based polymers yielding the highest storage modulus (560.1 MPa), glass transition temperature (72.0 °C), crosslink density (710 mol/m3), Young’s modulus (312 MPa), and tensile strength at break (21.9 MPa), but the lowest elongation at break (8.6%) versus materials prepared from epoxidized field pennycress, hempseed, and soybean oils. In contrast, pennycress-based polymers were the weakest but most ductile owing to the lower average oxirane content and longer fatty acid chain length of epoxidized pennycress oil. Lastly, chemical degradation studies demonstrated nearly complete hydrolysis under alkaline conditions, highlighting the potential of these materials as cleavable biobased epoxy networks for sustainable applications where high flexibility, low mechanical strength, and end-of-life degradability are advantageous.