Controlled organocatalyzed d,l-lactide ring-opening polymerizations: Synthesis of low molecular weight oligomers

Abstract

A systematic approach to the synthesis of organocatalyzed oligo(d,l-lactide) demonstrates that choice of initiator, catalytic ratio, and reaction time yields well-controlled oligomers. Ring-opening polymerization of d,l-lactide with the initiator α-methyl propargyl alcohol, a secondary alcohol, used in excess of 4-dimethylaminopyridine catalyst mitigates cyclicization, transesterification, and catalyst-initiated side reactions. This approach enables the design of uniform lactide oligomers for controlled release applications, such as delivery systems for drugs, prodrugs, and molecular sensors.