Homopolymer and copolymers of 4‐methacrylamidophenyl‐4‐methoxystyryl ketone with methyl methacrylate: Synthesis, characterization, reactivity ratios, and photocrosslinkable properties

Abstract

Abstract4‐Aminophenyl‐4‐methoxystyryl ketone (APMSK) was prepared by reacting 4‐aminoacetophenone and 4‐methoxybenzaldehyde in the presence of sodium hydroxide as base catalyst. The methacrylamide monomer, 4‐methacrylamidophenyl‐4‐methoxystyryl ketone (MPMSK), was synthesized by reacting APMSK with methacryloyl chloride in the presence of triethylamine. Free‐radical solution polymerization technique was used to prepare the homo‐ and copolymers of different feed compositions of MPMSK with methyl methacrylate in methyl ethyl ketone solution at 70°C, using benzoyl peroxide as the initiator. The polymers were characterized by UV, IR, 1H‐NMR, and 13C‐NMR spectral techniques. The reactivity ratios of both comonomers were calculated using Fineman–Ross, Kelen–Tüdös, extended Kelen–Tüdös, and a nonlinear error‐in‐variables model (EVM) method using a computer program, RREVM. The molecular weights (M̄w and M̄n) and polydispersity indices of the polymers were determined using size exclusion chromatography. The glass‐transition temperatures of the polymers were determined by differential scanning calorimetry. The thermal stability of the polymers was measured by thermogravimetric analysis in air. The photoreactivity of the polymers was studied in chloroform solutions in the presence and absence of various triplet sensitizers. The effect of concentration of homopolymer and composition of the copolymers on the rate of photocrosslinking of the polymers was investigated. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci, 2006