Characterization of the prepolymer and gel of biocompatible poly(xylitol sebacate) in comparison with poly(glycerol sebacate) using a combination of mass spectrometry and nuclear magnetic resonance

Abstract

Abstract Atmospheric pressure chemical ionization (negative ion) and electrospray ionization (positive and negative ion) mass spectrometry and nuclear magnetic resonance ( 1 H NMR and 13 C NMR ) were used to characterize the prepolymer (i.e. uncrosslinked) poly(xylitol sebacate) ( PXS ), prepared by condensation of xylitol [X] and sebacic acid [S], and this was compared with poly(glycerol sebacate) ( PGS ), prepared by condensation of glycerol [G] and [S]. The PXS prepolymer, prepared at 118 °C/24 h, gave predominantly 1‐acyl‐[ XS ] and 1,5‐diacyl‐[ SXS ] species and smaller amounts of 2‐acyl substitutions. At 130 °C/24 h an increase of the amount of the 1‐acyl and 1,5‐diacyl substitutions in the [( SX ) n ], [S( XS ) n ] and [( XS ) n X] series was identified, as was found for the analogous PGS prepolymer ([(SG) n ], [S(GS) n ] and [(GS) n G] series). Novel tetrahydrofuranyl species were found in the PXS prepolymer. Further polymerization of the PXS prepolymer gave a gel which when analysed using 13 C NMR was shown to mainly contain 1‐acyl and 1,5‐diacyl substitutions. © 2014 Society of Chemical Industry