Effect of substitution on the reactivity of some new p‐phenylacrylamide derivatives with organotin monomers

Abstract

AbstractThree new monomers of p‐phenylacrylamide derivatives were prepared by either the reaction of p‐methyl‐, p‐nitro‐, and p‐chloroaniline with acryloyl chloride or with acrylic acid in the presence of dicyclohexyl carbodiimide (DCCI). The prepared monomers were copolymerized with each of tri‐n‐butyltinacrylate and tri‐n‐butyltinmethacrylate. Copolymerization reactions were carried out in dioxane at 70°C using 1 mol % azobisisobutyronitrile as a free radical initiator. The structure of the new monomers and the prepared copolymers were investigated by IR and 1H‐NMR spectroscopy. The monomer reactivity ratios for the copolymerization of p‐chlorophenylacrylamide (M1) with each of tri‐n‐butyltinacrylate (TBTA) and tri‐n‐butyltinmethacrylate (TBTMA) (M2) were found to be r1 = 2.6; r2 = 0.83 and r1 = 1.3; r2 = 1.71, respectively. In case of p‐tolyacrylamide (M1) with TBTA and TBTMA (M2) r1 = 0.35, r2 = 1.03 and r1 = 1.38, r2 = 0.366 respectively. The Q and e values for the prepared p‐tolyl‐ and p‐chlorophenylacrylamide were calculated © 1993 John Wiley & Sons, Inc.