Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties

Sami Halila (1) , Maggy Manguian (2) , Sébastien Fort (1) , Sylvain Cottaz (1) , Thierry Hamaide (3) , Etienne Fleury (2) , Hugues Driguez (1)

1 CERMAV - Centre de Recherches sur les Macromolécules Végétales
2 IMP-LMM - Ingénierie des Matériaux Polymères - Laboratoire des Matériaux Macromoléculaires
3 IMP-LMPB - Ingénierie des Matériaux Polymères - Laboratoire des Matériaux Polymères et des Biomatériaux

Well-defined glyco-polyorganosiloxanes were synthesized by the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction (often simply referred to as click chemistry). N-propargylglycosylamines 2 and 4 were first synthesized from cellobiose (1) and xylogluco-oligosaccharide XGOs 3 without protecting groups. The azide function was introduced into polydimethylsiloxanes [PDMS: 5 (MDM) and 7 (MDM)] by azidolysis of the counterpart epoxy silicon with NaN3 to afford the mono-azido 6 and di-azido 8 derivatives, respectively. The coupling reaction took place in a hydro-alcoholic medium in the presence of CuSO4/sodium ascorbate as catalyst. Only one compound, MDM-click-XGO 12 showed good solubility in water with interesting surfactant properties.

Domaines: Polymères

Sami Halila, Maggy Manguian, Sébastien Fort, Sylvain Cottaz, Thierry Hamaide, et al.. Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties. Macromolecular Chemistry and Physics, 2008, 209 (12), pp.1282-1290. ⟨hal-00373953⟩