Functional polymers. XIX. Biuret oligomers and polymers of biologically active primary aliphatic amines

Biuret oligomers and polymers from primary aliphatic amines and aromatic or aliphatic diisocyanates have been synthesized. To demonstrate the feasibility of the synthesis of polybiurets, aliphatic primary amines with n-propyl, n-hexyl, n-octyl, and n-dodecyl groups have been incorporated. For the synthesis of biuret oligomers of biologically active primary aliphatic amines [8-(4-amino-1-methylbutylamino)-6-methoxyquinoline] (primaquine) and adamantanamine were selected. Primaquine was also incorporated into polyepichlorohydrin by nucleophilic substitution of the chlorine of the chloromethyl group by the primary aliphatic amino group of primaquine. The structure of the biuret polymers was established by elemental analysis, and by infrared ¹H- and ¹³C-NMR spectroscopic characterization. Several attempts to use primaquine as a diamine for the formation of condensation polymers, including reaction of primaquine with sebacoyl chloride (to form polyamides), or with diisocyanates (to form polyureas) were unsuccessful.