Cyanoacrylates were homo- and copolymerized with 2-chloroethyl methacrylate in the presence of a disulfide-containing crosslinker, bis(2-methacryloyloxyethyl) disulfide and an efficient chain transfer agent, carbon tetrabromide, to yield branched polymers with reductively degradable links at the branching points. To prevent anionic polymerization, small amounts of trifluoroacetic acid were added to the reaction mixtures. The polymers contained multiple alkyl bromide peripheral groups, which, along with the alkyl chloride pendant groups originating from 2-chloroethyl methacrylate, were into azide groups. The latter were used to attach various alkyne-functionalized molecules via copper catalyzed click chemistry. The detailed kinetics of the polymerization, reductive degradation in the presence of phosphines, azidation, and click-type functionalization will be presented.

Synthesis and functionalization of degradable, disulfide-containing, branched polycyanoacrylates

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.