Synthesis of poly(2-acetamidoacrylic acid) and its PEGMA block copolymer via ATRP in water

Abstract

Controlled polymerization of a captodative monomer, 2-acetamidoacrylic acid (AAA), was studied for the first time in the literature. Salt of the monomer in water was polymerized using ATRP method and influence of several factors, including solvent composition, halogen exchange and additives like pyridine and halide salts were investigated to improve the control. Captodative monomers form very stable radicals favoring the active species over the dormant one. Depolymerization at room temperature under ATRP conditions was determined as the major obstacle in front of the high molecular weight polymers and block copolymer formation. Nevertheless, poly(AAA-b-(AAA-co-PEGMA)) block polymers were prepared through ATRP and possible applications were discussed. As an example, pH responsive nature and ability to coat superparamagnetic iron oxide nanoparticles were demonstrated. (C) 2013 Elsevier Ltd. All rights reserved.