1-ポリオキシエチレンピリジニウム-2-ドデカノイルイミンの合成と性質

概要

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A series of 1-poly (oxyethylene) pyridinium-2-dodecanoylimines (3) were synthesized in a good yield from 2-aminopyridine and poly (oxyethylene) (POE) monochlorides ranging in oxyethylene number (n) from 1 to 5. Some properties of (3) were examined and compared with those of 1-methylpyridinium-2-octanoylimine (4) and dodecyl POE ethers (5). (3) with n≤3 were more soluble in water than (4) and their specific cloud point increased with increasing the number of n. The surface tension reduction of (3) was similar to that of (4). The cmc value of (3) was about one-hundredth of that of (4) but similar to that of (5). From the relationship of (Fig.-1) between cloud point and n of (3) and (5), it was estimated that the hydrophilic effect of the pyridinium-2-imine group in (3) corresponded to that of two or three oxyethylene units in (5). On the basis of IR spectra and the aqueous properties of (3), it was concluded that the contribution of the dipolar ionic form of (3) was strong especially in an aqueous environment.