Synthesis and Fluorescent Performance of Fluorescein-functionalized Waterborne Polyurethane

A novel yellow fluorescent diisocyanate 3,6-di(hexamethylene urethano)spiro[xanthene-9,3′-phthalide] diisocyanate (DIX) was synthesized by the reaction of fluorescein with hexamethylene diisocyanate first. Using DIX to substitute partially isophorone diisocyanate (IPDI), a kind of yellow fluorescent waterborne polyurethane DIX-WPU was prepared by blocking the fluorophore of DIX into the polyurethane chain using IPDI, polytetramethylene ether glycol and 2,2-dimethylol propionic acid. The molecular structure of DIX and DIX-WPU was confirmed by means of Fourier transform infrared spectroscopy. The fluorophore is fixed permanently in the polyurethane chain and is difficult to migrate due to the covalent bonding with other component during the synthesis. The fluorescence intensity of DIX-WPU fluorescent dispersion was enhanced greatly comparing with that of fluorescein in a wide range of fluorophore content between 1 × 10–7 and 1 × 10–3 mol/L. The fluorescence of DIX-WPU dispersion is very stable not only for the long term storage but also for the fluorescence quencher. It was found that the fluorescence intensity of DIX-WPU increased with the increase of temperature.