On the homopolymerization of epoxidized eugenol and its copolymerization with bisphenol A diglycidyl ether

Abstract The curing of the biobased monomer 2-methoxy-4-(2-oxiranylmethyl)phenol, trivially called epoxidized eugenol (EE), with two industrially relevant Lewis base initiators is studied by differential scanning calorimetry and the results are compared with the curing of bisphenol A diglycidyl ether (DGEBA). The polymerization of EE initiated with either 1-methylimidazole (1-MI) or 2,4,6-tris(dimethylaminomethyl)phenol (K54) requires temperatures of about 80 °C to proceed at a practically reasonable rate. The highest glass transition temperature ( T g ) of 79 °C is obtained by curing EE with 10 mol% K54. The T g s of homopolymers of EE initiated with K54 depend on the initiator loading and are 15–20 °C higher than those obtained with 1-MI. The polymerization of blends of EE and DGEBA at 80 °C is faster than the curing of either monomer alone. The T g s of the copolymers prepared with K54 are largely unaffected by the ratio of the two monomers and are in the range of 94–96 °C for 2:1, 1:1, and 1:2 blends and 5 mol% K54 loading. In contrast, with 1-MI, the copolymers show higher T g s with lower EE content in the formulation. The thermoset made from 1 part EE, 2 parts DGEBA, and 0.05 parts 1-MI shows a satisfactory high T g of 134 °C. Graphical abstract