Aminimides are a new class of surface active agents which have antimicrobial activity. These bipolar compounds have activity against both gran‐positive and yeast organisms. Their activity against gram‐negative organisms is low or absent. The acyl derivatives tested showed maximum activity at chain lengths of C14 and C16. Fatty acid derivatives, shorter (C16), were less active. Unsaturation was an important factor contributing to aminimide activity. Their low toxicity and wide spectrum of antimicrobial activity make aminimides ideal candidates for further investigation.
Acyclic, alicyclic, and aromatic bis-trimethylaminimides and a keto-substituted trimethylaminimide have been synthesized by a stepwise route of general applicability. Pyrolysis of the aliphatic aminimides resulted in a rearrangement to trimethylamine and isocyanate. The keto-isocyanate herein reported was synthesized in a convenient four-step sequence from dimethyl ketene dimer in a good yield, and provides an attractive new route to this type of difunctional compound. Pyrolysis of the bis-aminimides in the presence of polyhydroxylic materials gave polyurethanes.
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