Chelating Polymers. III. Chelating Monomers and Polymers from s-Triazinyl Substituted Hydrazinoacetic Acids

The model chelating compounds β-[2,4-bis(dimethylamino)-s-triazin-6-yl] hydrazinoacetic acid, β-[2,4-bis(dimethylaniino)-s-triazind-yl] hydrazino-N, N-diacetic acid, 2,4-bis(dimethylamino)-s-triazin-6-yl-aminoacetic acid, and 2,4-bis(dimethylamino)-s-triazin-6-yl-iminodiacetic acid have been synthesized and characterized by composition analysis, infrared spectroscopy, and potentiometric titration data. The copper(II), nickel(II), cobalt(II), zinc(II), magnesium(II), and palladium(II) complexes of the first two model compounds, and the copper, nickel, cobalt, and zinc complexes of the third and fourth model compounds have been prepared. The infrared absorption spectra of the model compounds and their complexes were recorded for the range 3800 to 600 cm^?1, and the assignment of pertinent bands was made by comparison with reported infrared correlations. In those cases where applicable, shifts in the NH stretching vibration and carboxylate stretching vibration frequencies of the metal complexes were compared to those of the proper references and used as an indication of possible chelation effects in the metal complexes.

The aldehyde-reactable β-[2,4-diarnino-s-triazin-6-y1] hydrazinoacetic acid was also prepared and characterized; its polymers were prepared by the reaction of both the free ligand and its copper(II) complex with formaldehyde. Qualitative studies on the reaction of these polymers with metal ions and on the ease of metal ion elution from the polymers indicate that t h is a promising chelating polymer system.