Synthesis and copolymerization reactions of p‐acryloyloxybenzoic acid with organotin monomers

Abstract

Abstractp‐Acryloyloxybenzoic acid (PAB) was prepared by the reaction of p‐hydroxybenzoic acid and acryloyl chloride in the presence of triethylamine. Triphenyltin acrylate (TPTA), triphenyltin methacrylate (TPTMA), p‐acryloyloxytriphenyltin benzoate (TPTB) and triphenyltin itaconate (TPTI) monomers were prepared by the reactions of acrylic, methacrylic, p‐acryloyloxybenzoic and itaconic acids, respectively, with triphenyltin hydroxide in the presence of dicyclohexylcarbodiimide (DCCI) as a dehydrating agent. Binary copolymerizations of PAB with TPTA, TPTMA, TPTB and TPTI were performed in dimethylformamide (DMF) using 1 mol% azobisisobutyronitrile (AIBN) as initiator at 65 °C. The structures of the monomers and copolymers were investigated by IR and 1H NMR spectrometry. The composition of the copolymers was determined by tin analysis. Copolymerization parameters for each system were calculated by both the Fineman–Ross and Kelen–Tüdös methods. The monomer reactivity ratios for the four systems studied, PAB‐TPTA, PAB‐TPTMA, PAB‐TPTB and PAB‐TPTI, were found to be r1 = 0.468, r2 = 2.096; r1 = 0.435, r2 = 2.292; r1 = 0.449, r2 = 2.225 and r1 = 0.416, r2 = 4.526, respectively. The average Q and e values for the prepared organotin monomers were calculated. Copyright © 2004 Society of Chemical Industry