Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

Article abstract of DOI:10.1016/0223-5234(92)90020-2

Two methods for synthesizing tertiary F-alkylated amines are reported. The more general method allows the access in 56-87% yields to various N,N-dialkyl F-alkyl amines. These amines are key intermediates leading in 52-96% yields to several families of surfactants, including zwitterionic and cationic derivatives and amine oxides, potentially useful in the formulation of fluorocarbon emulsions for diagnostic and therapeutic uses. The toxicity of the new surfactants and the influence of the polar head were assessed: the long chain compounds (8, 9 and 10) were found to be toxic for cell cultures and the zwitterionic compounds (7b and 8) have a LD₅₀ < 250 mg ·g kg bw^-1 in mice. The hemolysis test highlights the influence of the polar head: the zwitterionic compounds (7 and 8) were found to be non-hemolytic even at remarkably high concentrations (100 g l^-1 for 8), whereas the cationic compounds 9 are highly hemolytic even at very low concentrations (0.05 g l^-1).