Novel approach for the synthesis of hydrophobe modified polyacrylamide. Direct N-alkylation of polyacrylamide in dimethyl sulfoxide

Abstract

We found that dimethyl sulfoxide (DMSO) dissolves PAAm. Direct N-alkylation of the amide groups of polyacrylamide was performed under homogeneous condition in DMSO. By using tert-butoxide, the amide groups of PAAm were turned into amide cations, followed by a coupling reaction with alkyl bromide to give N-alkylated PAAm. 1H NMR suggests that the incorporation of alkyl bromide proceeded quantitatively. Intrinsic viscosity measurements and 13C NMR spectra in DMSO suggest that undesirable side reactions such as cross linking or hydrolysis of the amide groups did not take place during the reaction.