Synthesis and spreading behaviour of some reactive derivatives of long-chain alcohols and carboxylic acids

Procedures are described for the synthesis of several azides, diimides, and azodiformates from long-chain alcohols and fatty acids. These reactive compounds have potential applications as thermal and photochemical curing agents, and as surface-modifying agents for the preparation of filled plastics and chromatographic packings. The surface activity of the compounds was characterized by investigations of their spreading behaviour in monolayers on water. Unlike the single-chain azides and azo compounds, which give well-defined monolayers at all temperatures, monolayers of diacyl diimides and dialkyl azodiformates with two long-chain substituents are unstable with respect to collapse to the bulk solid. The photoreaction of monolayers of octadecanoyl azide to give a mixture of products derived from an intermediate isocyanate was demonstrated by ir and mass spectrometry.