Functionalization and Chemical Modification of 2-Hydroxyethyl Methacrylate with Carboxylic Acid

Abstract

Free radical polymerization of the resulting monomers methyl methacrylate (MMA), ethyl methacrylate (EMA), methylacrylate (MA) and ethylacrylate (EA) with 2-hydroxyethyl methacrylate (HEMA) (in 1:1 mole ratio) were carried out using azobis(isoboutyronitrile) (AIBN) as initiator at the temperature ranges 60-70°C. The modification of polymers were carried out by 9-anthracenecarboxylic acid (9-ACA) via the esterification reaction between —OH of poly(HEMA) and —COOH of 9-ACA, in presence of N,N′-dicyclohexyl-carbodiimide (DCC), 4-(dimethylamino) pyridine (DMAP) and N,N-dimethyl formamid (DMF). It was found that the molar ratio acid/alcohol/catalysts= 0.02: 0.02: 0.02 and 0.002, optimal for preparation of the ester. As demonstrated by FT-IR, 1H-NMR and dynamic mechanical thermal analysis (DMTA). The Tg value of methacrylate and acrylate copolymers containing 9-ACA groups was found to increase with incorporation of 9-ACA groups in polymer structures. The presence of 9-ACA groups in the polymer side chains created new polymers with novel modified properties that find some applications in polymer industry. These anthracenic factors could take part in cyclo addition reaction with other factors such as anhydrides and kinons.