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M. Bednarek

Application of cationic polymerization by activated monomer mechanism

and click reactions for the synthesis of functionalized polylactide

Polimery 2012, No 7-8, 501


DOI: dx.doi.org/10.14314/polimery.2012.501

Summary

Polylactide (PLA) functionalized at one chain end with propargyl group (Propargyl-PLA, Fig. 1, 2) was synthesized using ring-opening polymerization in the presence of protic acid and alcohol, proceeding via activated monomer mechanism. The synthetic conditions were chosen so as to obtain the polymer with a predetermined molecular weight and to exclude transesterification and racemization reactions during the polymerization process (Table 2, Fig. 3). Polylactide functionalized with propargyl group was subjected to click reactions with the compounds containing azide (Fig. 4) and thiol groups. In the case of azide addition the possibility of formation of block copolymers, with an example of the coupling of Propargyl-PLA to poly(ethylene glycol) bearing -N3 group at one chain end (Fig. 5), was shown. The reactivity of terminal alkine group of Propargyl-PLA was also proved in the „thiol-yne” reaction, with a-toluenethiol (Fig. 6).


Key words: ring-opening polymerization, cationic polymerization, polylactide, functionalization, click reaction

e-mail: bednarek@cbmm.lodz.pl

M. Bednarek (307.2 KB)
Application of cationic polymerization by activated monomer mechanism and click reactions for the synthesis of functionalized polylactide