Synthesis and characterization of water soluble saccharide functionalized polysiloxanes and their use as polymer surfactants for the stabilization of polycaprolactone nanoparticles

Abstract

Monosaccharide functionalized polysiloxanes bearing either terminal or pendant mannose moieties have been obtained starting from the allyloxyethyl glycosidie and appropriate H-containing siloxane compounds, via hydro-silylation reactions. The starting modified monosaccharide was reacted as trimethylsilyl protected derivative and a convenient method for deprotection of the hydroxyl groups was found in order to avoid the degradation of the polysiloxane chains. The reaction products were characterized by IR and NMR spectroscopy. The water solubility of these functionalized polysiloxanes was investigated and critical micelle concentration values were found to be in the range 10 -4-10-5 M. Some of the water soluble compounds were used as non ionic surfactants for the elaboration of poly-(ε-caprolactone) nanoparticles by nanoprecipitation, and particle sizes of less than 200 nm were observed. © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.