Synthesis and Radical Polymerization of N-(3-Acetyl-4-Carboxy-Phenyl)-Maleimide

Abstract

A new functional monomer derivative of p-aminosalicylic acid, N-(3-acetyl-4-carboxy-phenyl)-maleimide, was synthetized and polymerized with azobisisobutyronitrile as initiator at 60 °C in various solvents. The obtained structures were confirmed by IR, 1H-NMR and elemental analysis. The molecular weights and the polydispersity values of the polymers were determined in the ranges (3.4–5.9)×103 and 1.28–1.60 respectively, by gel permeation chromatography. The activation energy of the monomer polymerization in tetrahydrofuran was calculated as 26.11 kcal mol−1. The x-ray analysis shows, in all cases, the existence of two characteristic diffraction maxima ( di, do), and the influence of the length and size of the aromatic substituents on these maxima are discussed. Functional polymers members of the salicylic acid family would lead to polymers which should show chelation, catalytic, thermochromic or photochromic properties.