Copolymerization of 4-benzyloxycarbonylphenyl methacrylate with glycidyl methacrylate: synthesis, characterization, reactivity ratios and application as adhesives

Abstract

The new functional methacrylic monomer, 4-benzyloxycarbonylphenyl methacrylate (BCPM) was synthesized by reacting benzyl-4-hydroxybenzoate dissolved in ethyl methyl ketone (EMK) with methacryloyl chloride in the presence of triethylamine. The copolymers from different feed compositions of BCPM and glycidyl methacrylate (GMA) were synthesized by free radical polymerization in EMK solution at 70±1 °C, using benzoyl peroxide as an initiator. The copolymers were characterized by FT-IR, 1H-NMR and 13C-NMR spectroscopic techniques. The polydispersity indices of the polymers determined using gel permeation chromatography suggest a strong tendency for chain termination by disproportionation. The glass transition temperature of the copolymers was found to increase with increase in mole fraction of BCPM in the copolymer. Thermogravimetric analysis of the copolymers performed in air revealed that the thermal stability increases with increase in BCPM content in the copolymer. The solubility of the polymers was tested in various polar and non-polar solvents. Copolymer compositions were determined using 1H-NMR spectra. The monomer reactivity ratios were determined by the application of conventional linearisation methods such as Fineman–Ross, Kelen–Tüdös and extended Kelen–Tüdös and a nonlinear error invariable model method using a computer program RREVM. The adhesives based on poly(BCPM- co-GMA) were prepared for application on leather and their peel strengths were determined at 50 and 70 °C.