Homopolymer and copolymers of 4‐benzyloxycarbonylphenyl acrylate with glycidyl methacrylate: Synthesis, characterization, reactivity ratios, and application as adhesive for leather

Abstract

Abstract4‐Benzyloxycarbonylphenyl acrylate (BCPA) was prepared by reacting benzyl‐4‐hydroxy benzoate dissolved in methyl ethyl ketone with acryloyl chloride in the presence of triethylamine. The homopolymer and copolymers of BCPA with glycidyl methacrylate (GMA) having different compositions were synthesized in methyl ethyl ketone using benzoyl peroxide as a free‐radical initiator at 70 ± 1°C. All the polymers were characterized by FTIR, 1H‐NMR, and 13C‐NMR spectroscopic techniques. The solubility of the polymers was tested in various polar and nonpolar solvents. The molecular weights (Mw and Mn) and polydispersity indices of the polymers were determined using gel permeation chromatography. The glass‐transition temperatures of the copolymers increased with increasing GMA content in the copolymer. Thermogravimetric analysis of the polymers performed in air showed that the thermal stability of the copolymer increased with increasing BCPA content. Copolymer compositions were determined using 1H‐NMR analysis. The monomer reactivity ratios were determined by the application of conventional linearization methods such as Fineman–Ross (r1 = 0.5237; r2 = 1.9646), Kelen–Tüdös (r1 = 0.4996; r2 = 1.8741), and extended Kelen–Tüdös (r1 = 0.4652; r2 = 1.9046) as well as a nonlinear error‐in‐variables model (EVM) method, using the computer program RREVM (r1 = 0.4644; r2 = 1.8324). The peel strength of the leather adhesives prepared from the copolymers was also determined. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 91: 3604–3612, 2004