Innovation new route for preparation of polyacrylamide bearing urethane group based on one-pot Curtius rearrangement

One-pot combination of Curtius rearrangement and radical polymerization of an acrylamide derivative bearing carbonyl azide group (ACA) was investigated to provide polyacrylamide bearing side-chain isocyanate groups. The one-pot Curtius rearrangement and radical polymerization successfully proceeded at a low monomer concentration (0.05 mol/L) to avoid cross-linking between the side-chain isocyanate groups. The one-pot conversion of the in situ generated isocyanate groups into the urethane groups succeeded by the excess amount of alcohol to be reacted (100 equivalents to ACA). The one-pot reaction in the presence of various alcohols (methanol, ethanol, propanol, and butanol) proceeded smoothly to provide the polyacrylamide bearing various urethane moieties with number average molecular weights ( M n = 1200 ~ 1600) in 63–96% yields.