Synthesis and properties of fatty imidazolines and their N‐(2‐aminoethyl) derivatives

Cationic high molecular weight surfactants hold promise as water repellents for soil for water harvesting. Specifically, the products of the reaction of 2 moles of fatty acids with 1 mole of diethylenetria-mine were investigated. Optimum conditions for the formation of imidazolines as well as the open-chain N-(2-aminoethyl) derivatives, i.e., the diamides, were determined. Saturated fatty acids, pelargonic through behenic, oleic acid, elaidic acid as well as tallow, tallow fatty acids, and hydrogenated tallow fatty acids, were converted in 6 hr at 150 C to form the diamides. The fatty imidazolines were synthesized by cyclizing the diamides at 150 C for 2 hr under reduced pressure in a 92% yield. The crude imidazolines were purified by crystalliza-tion. The fatty imidazolines were readily hydrolyzed at the C=N bond of the imidazoline ring with water or dilute alcohol. The resulting diamides, RCON(CH2 CH2 NH2)CH2 CH2 NHCOR, were also purified by crystallization. Water repellency of these com-pounds was evaluated by contact angle measurements and percola-tion tests. The surface properties of these series of compounds are determined by four parameters. The open-chain diamides are more hydrophobic than the analogous imidazolines, and hydrophobicity increases with increasing molecular weight of derivatives of saturated fatty acids. Oleic acid derivatives are far more hydrophilic than the saturated acid derivatives or the analogous elaidic acid derivatives. The latter are more hydrophilic than stearic derivatives.