Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from D-galactose

M.V. RIVAS; G. PETROSELLI; R. ERRA-BALSELLS; O. VARELA; A. A. KOLENDER

RSC Advances

Royal Society of Chemistry

Año: 2019

a-Azide-u-alkynyl ester monomers were designed and synthesized in order to obtain hydrolyticallydegradable polymers. The monomers were prepared from D-galactose, as a renewable resource.Environmentally benign azido?alkyne cycloaddition polymerizations were conducted to affordpoly(ester-triazole)s, with complete atom economy. Although polymer formation prevailed underoptimized polymerization conditions, variable proportions of cyclic oligomer byproducts were detected.The Cu-catalyzed click polymerization led regioselectively to 1,4-disubstituted triazole linkages, whilethe thermal, metal-free polymerization produced a random distribution of 1,4- and 1,5-disubstitutedtriazoles in the polymer backbone. The poly(ester-triazole)s exhibited high molecular weights (Mw in therange 35?85 kDa). They were soluble in organic solvents but highly insoluble in water, thus removal ofthe Cu(I) catalyst was simplified. The polymers were stable up to 300 C, and had Tg values in the range90?100 C. The materials were hydrolysed under either basic or strong acid conditions, and thedegradation products have been characterized.