Preparation and characterization of thermally stable poly(amide-urea)s functionalized with anthraquinone chromophore

Two new diamines containing bulky anthraquinone pendant units were prepared via reactions of land 2-aminoanthraquinone with 3,5-dinitrobenzoylchloride and a subsequent reduction of their nitro groups. A novel series of highly organosoluble poly(amide-urea)s were synthesized from the reactions of the prepared diamines with various commercially available diisocyanates via a step-growth addition reaction process in N-methyl-2-pyrrolidone (NMP). The effects of two factors (time and temperature) on the reaction were studied to optimize the conditions for the preparation of high molecular weight polymers. All poly(amide-urea)s were characterized by Fourier Transform Infrared (FTIR) and H-1-nuclear magnetic resonance (NMR) spectroscopies and elemental analysis. The resulting poly(amide-urea)s had inherent viscosities in the range of 0.54-0.73 dl/g. They exhibited excellent solubility in polar solvents. The temperature for 10% weight loss of the polymers in air was all above 285 degrees C, their residues were more than 36% at 700 degrees C in air, and their T-g values were in the range of 148-190 degrees C. According to the wide-angle X-ray diffraction (WAXD), the polymers were almost amorphous. The optical properties of poly(amide-urea)s measured by ultraviolet-visible (UV-Vis) spectroscopy showed absorption maxima at 303-429 run. Copyright (C) 2008 John Wiley & Sons, Ltd.