Covalent immobilization of chitosan derivatives onto polymeric film surfaces with the use of a photosensitive hetero-bifunctional crosslinking reagent

Abstract

Partially N-acetylated chitosan was covalently immobilized onto polymeric film surfaces using the photosensitive hetero-bifunctional crosslinking reagent, methyl 4-azidobenzoimidate, which was previously attached to the chitosan by the reaction between an imidoester group of the reagent and a free amino group of the chitosan. The grafting was accomplished by irradiating with ultraviolet light the modified chitosan being coated on the film surfaces to photolysis arylazide groups, thus crosslinking the chitosan and the underlying substrate polymer together. For ultraviolet absorption and infrared spectroscopy, the irradiation time of 3 min was found to be sufficient for the photolysis of the azide group. The thickness of the immobilized chitosan layer was estimated to be of the order of 30-150 nm using attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR). The chitosan molecules immobilized on the surfaces could be chemically modified by several reagents and also treated with a heparin solution to form a polyelectrolyte complex on the surface. The ionically bound heparin was partially released into a phosphate buffer solution.