Isosorbide monoacrylate: a sustainable monomer for the production of fully bio-based polyacrylates and thermosets

Abstract

Isosorbide monoacrylate (IMA) is a fully bio-based monomer formed by the reaction between isosorbide and acrylic acid. From a fundamental point of view and as a potential substitute for the current petro-based and carcinogenic monomers, it is crucial to understand its behaviour during a conventional radical polymerization. To this end, the radical polymerizability of IMA has been investigated in depth under various conditions (i.e. different solvents or [IMA]/[Initiator(AIBN)] ratios). In all cases, plateaus are reached for M_n. The Mayo method of IMA free radical polymerization was carried out and the transfer to monomer (C_trM) constant was determined to be up to 1.4 × 10⁻³. Depending on the molecular weight, PIMA with a large range of T_g from room temperature to higher than 100 °C could be obtained. Furthermore, the treatment of high-T_g PIMA with succinic anhydride leads to a high-performance thermoset featuring thermomechanical properties close to those of commercial epoxy resins such as DGEBA-based resins (T_g = 116 °C and E′ = 4 GPa).