Site-site interactions in a polymer matrix: Effect of amine structure on transformations of copoly(styrene-p-nitrophenylacrylate)

Crosslinked copoly(styrene-p-nitrophenylacrylate)s (1a, 1b and 1c, containing 2, 4 and 10% divinylbenzene, respectively) reacted readily with secondary amines (piperidine, morpholine, piperazine, N-phenylpiperazine), the course of substitution bring influenced by the crosslinking of 1, solvent polarity (dimethylformamide, methanol, toluene) and the structure of the amine. Steric interactions influenced the transformation of 1a with various primary amines (n-butylamine, i-propylamine and cyclohexylamine) giving the corresponding amides; tertbutylamine and aniline do not transform la under similar reaction conditions (dimethylformamide, T=50 degrees C). The swelling ability of the resins depended on the crosslinking of the starting copoly(styrene-p-nitrophenylacrylate) (1), the structure of the amide and solvent polarity (water, methanol, dimethylformamide, toluene, chloroform, cyclohexane). Copyright (C) 1996 Elsevier Science Ltd.