Synthesis and characterization of dithiocarbamate surfactants

New dithiocarbamate surfactants 2 (potassium N-2-[2-(2-methoxyethoxy)ethoxy]ethyl-N-dodecyldithiocarbamate), 3 (potassium N-2-(2-alkoxyethoxy)ethyl-N-dodecyldithiocarbamate; a, alkoxy = C6H13O; b, alkoxy = C8H17O), and 4 (potassium N-2-decoxyethyl-N-dodecyldithiocarbamate), as well as 5 (potassium N,N-didodecyldithiocarbamate) were prepared. The synthetic route to 2–4 is a useful, general alternative to that reported for related surfactants. The molecular compositions of 2–5 were confirmed by combustion analyses and electrospray mass spectrometry, and their structures were established by 1H and 13C NMR spectroscopy. Surfactants 2–5 in water were characterized by Krafft temperature, solubility, and critical aggregation concentration measurements, and aggregated surfactants were characterized by dynamic laser light scattering. Surfactant 2 forms micelles in water, in contrast to 3–5, which form vesicles.