Free‐radical‐initiated copolymerization of 2‐(2‐naphthylamino)‐2‐oxo‐ethyl methacrylate with methyl methacrylate and styrene

Abstract

A naphthylamino species containing the methacrylate‐based monomer 2‐(2‐naphthylamino)‐2‐oxo‐ethyl methacrylate (NphAOEMA) was synthesized by reacting 2‐chloro‐N‐2‐naphthylacetamide (NphA) with sodium methacrylate in acetonitrile. The acetamide was prepared by reacting 1‐naphthylamine, dissolved in benzene, with chloroacetylchloride. The free‐radical‐initiated copolymerization's of NphAOEMA, with methyl methacrylate (MMA) and styrene (ST), were carried out in dimethylsulfoxide (DMSO) solution at 65 °C using 2,2′‐azobisisobutyronitrile (AIBN) as the initiator with various monomer‐to‐monomer ratios in the feed. The monomer (NphAOEMA) and copolymers were characterized from FT‐IR, 1H and 13C NMR spectral studies. The copolymer compositions were evaluated by determining the nitrogen contents in the polymers. The reactivity ratios of the monomers were determined by the application of the Fineman–Ross and Kelen–Tüdőos methods. The molecular weights (M̄w and M̄n) and polydispersity indices of the polymers were measured by using gel permation chromagtography. The thermal stabilities of the homo and copolymers were investigated by using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The solubilities and inherent viscosities of the homo and copolymers were also studied. Copyright © 2004 Society of Chemical Industry

Copolymers of N-(4-bromophenyl)-2-methacrylamide with 2-hydroxyethyl methacrylate

“…Several studies have been done in our laboratories on the synthesis of N-monosubstituted acrylamides [1][2][3] and their radical copolymerization with commercial monomers. These studies clearly show that the nature as well as position of the substituent had a large effect on monomer reactivity ratios, glass transition temperatures and antimicrobial properties.…”