Synthesis of O-acyl salicylaldehyde derivatives and copolymerization of bis-(2-formylphenyl) fumarate with methyl methacrylate

Abstract

To develop salicylaldehyde based bioactive materials, ester derivatives of salicylaldehyde were synthesized by O-acylation of the phenolic group. Different di- and tri-acyl chlorides were reacted with salicylaldehyde under basic conditions to obtain bis-(2-formylphenyl) succinate, bis-(2-formylphenyl) fumarate, bis-(2-formylphenyl) adipate and tris-(2-formylphenyl) benzene-1,3,5-tricarboxylate at room temperature in good to excellent yields. The structure of the derivatives was established using standard analytical methods e.g. 1H NMR, 13C NMR, HRMS, FT-IR, and SC-XRD. Bis-(2-formylphenyl) fumarate was copolymerized with methyl methacrylate by radical polymerization method using benzoyl peroxide as the initiator. The copolymer was analyzed using 1H NMR, FT-IR, TGA, DSC, SEM and EDX spectroscopic techniques. The thermal analysis of the copolymer showed an increase in glass transition temperature and the overall thermal stability as compared to poly (methyl methacrylate). The methods used here to develop O-acyl salicylaldehyde derivatives and the copolymer of one of the unsaturated monomers, bis-(2-formylphenyl) fumarate with MMA, have been successful.