Abstract

AbstractAn earlier paper reported the synthesis of derivatives of parabanic acid, mono‐ and dimethylol parabanic acid, and their polymerizations with themselves and with aqueous formaldehyde. The study is reported herein to clarify that work. The reported synthesis of monomethylol parabanic acid was not reproducible. Identical low‐molecular‐weight polymers were obtained from the condensation of parabanic acid with formalin and from the self‐condensation of dimethylol parabanic acid. The final polymer contains a little of the original parabanic acid and a large amount of the condensation product from a ring opening byproduct. Commonly, two products are possible, a soluble one at lower reaction times and temperatures and an insoluble one at longer times and temperatures. Films cannot be formed by solvent casting or heat pressing. Elemental analyses and infrared spectra show that the actual products are not of the structure originally proposed.

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