Diels–Alder Reaction as a Tool to Modify the Surface of Polymeric Microspheres

Abstract

The study describes the synthesis of glycidyl methacrylate microspheres cross-linked with ethylene glycol dimethacrylate. With the use of suspension–emulsion polymerization, microspheres with different degrees of cross-linking were prepared. Their chemical modification involved several steps: at the beginning, the epoxide ring was opened using sodium cyclopentadienide; in the next step, materials with grafted cyclopentadiene fragments were then subjected to Diels–Alder reaction with maleic anhydride; in the last step, the anhydride groups were turned into carboxylic groups. To confirm the attachment of cyclopentadiene to the microspheres surface, the material obtained was treated with fluorescence marker N-(1-pyrene) maleimide. The resulting material has fluorescent properties in the UV wavelength of 366 nm. Moreover, to confirm the chemical structure of modified materials, attenuated total reflection-Fourier transform infrared spectroscopy analysis was performed. Thermal stability in inert atmosphere of ...