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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.

Several analogues of polyacetylene including poly(phenylacetylene), poly(propiolonitrile), poly(3-chloro-1 -propyne), and poly(3,3,3-trlfluoro-1 -propyne) in which the conjugated backbone of polyacetylene is retained but where the hydrogen atoms are replaced by different pendant groups were prepared and their physical, thermal, and electrical properties were investigated. All of the polymers examined showed significant increases in conductivity after exposure to iodine vapor with the maximum conductivities observed ranging from 6 X 10~e to 2 X 10~3 ohm"1 cm"1. Although polyacetylene is a known electronic conductor, the preponderance of evidence indicated that poly(phenylacetylene) conducts through a predominantly Ionic mechanism. Similar behavior was also observed for poly(propiolonitrile), poly(3-chloro-1 -propyne), and poly(3,3,3-trifluoro-1 -propyne). The thermal properties of the various materials examined were also found to be similar with poly(propiotonitrile) displaying the greatest thermal stability.

A B S T R A C TIt was demonstrated that highly hindered bisphenols could be used to produce polyesters of moderate molecular weight. Bisphenols linked in the 4 and 4' or the 2 and 2' positions and substituted in positions ortho and para to the phenolic hydroxyl groups with methyl or tertiary butyl groups (these bisphenols a r e now used as very effective antioxidants) formed polymers, their reactivity depending more on the nature of the group linking the two phenyl rings than on the steric effects of the ortho substituents. Bisphenols linked in the 2 and 2' positions and containing bulky electron-withdrawing groups were found to be least effective as condensation monomers although successful polymerization to moderate molecular weight could be achieved using me 1 t pol yc ondensati on techniques . *For Part V& see Y. Sumida and 0. Vogl, Polym. J., 13(6), 521 ?Deceased, February 16, 1981.

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