Straightforward functionalization of acrylated soybean oil by Michael-addition and Diels–Alder reactions

• Several Michael-addition products of acrylated soybean oil (AESO) with different nitrogen and sulfur nucleophiles were prepared.
• Reversible Diels–Alder (DA) reactions with a bifunctional bismaleimide and a monofunctional maleimide were studied using different solvents.
• Thermal properties of DA derivatives were determined.

A straightforward Michael-addition reaction of acrylated soybean oil (AESO) with different nitrogen and sulfur nucleophiles is reported. The reaction proceeded under mild conditions and the products were obtained in good yields. The reaction product of AESO with furfurylamine (FA) was used in Diels–Alder (DA) reactions with a bifunctional (1,1′-(methylenedi-4,1-phenylene) bismaleimide (BMI) and a monofunctional maleimide (N-phenylmaleimide, PMI), in different solvents. The 1H NMR spectroscopic analysis of the AESO-FA-PMI revealed the presence of both exo and endo DA adducts. The reverse DA reaction (rDA) of the AESO-FA-PMI (BMI) derivatives was shown to take place at temperatures between 103 and 134 °C, with enthalpy changes ranging from 4.7 to 29.5 J/g. The results indicate that the solvent used in the furan–maleimide DA reaction has an important role in determining the properties of the adduct formed.