Chemistry of alkenyl azlactones. IV. Preparation and properties of telechelic acrylamides derived from amine‐terminated oligomers

The ring‐opening, nucleophilic addition of amine‐terminated oligomers to alkenyl azlactones was exploited to prepare reactive, that is, in free radical polymerizations, oligomers that could be used in 100% solids resin systems. Acrylamide‐functional oligomers resulted from the reaction that used 2‐vinyl‐4,4‐dimethylazlactone, whereas methacrylamide‐functional oligomers were produced with 2‐isopropenyl‐4,4‐dimethylazlactone. The overall reaction took place under mild conditions, for example, a few hours at room temperature, and was particularly free of side reactions. Examination of reaction rates with the two alkenyl azlactones revealed that the 2‐vinyl derivative reacted ca. four times faster. The (meth)acrylamide‐terminated resins were characterized by IR, NMR, and molecular weight analyses.