Fluorinated Pyridinium and Ammonium Cationic Surfactants

New classes of partially fluorinated cationic surfactants, including pyridinium sulfonates and ammonium hydrochlorides have been prepared in which a fluoroalkyl chain is interrupted either by ether oxygen (—O—), or by methylene (—CH₂—) units. These surfactants are obtained from multi-step syntheses via intermediate fluoroalkyl ethylene iodides (RfO(CF₂CF₂)nCH₂CH₂I, Rf = C₃F₇, C₂F₅,n = 1–3 or Rf(CH₂CF₂)m(CH₂CH₂)n, Rf = C₄F₉, C₆F1_3m = 0–2, n = 1–2) or fluoroalkyl iodides (RfI, Rf = C₃F₇O(CF₂CF₂)₃I, C₆F₁₃). The surface activities of these fluorinated cationic surfactants were examined and compared to commercially available fluorinated cationic surfactants used as additives in oil field applications. Some examples demonstrated good performance relative to controls yet are more fluorine efficient because they have lower fluorine content than their perfluoroalkyl analogues. For the ammonium hydrochlorides, the effect of different spacer groups between the cation and the fluorinated chain including ethylene, butylene and isopropylidene on surface activity was also examined.