A Zwitterionic Polymerizable Surfactant from ω‑Hydroxyltetradecanoic Acid Provides Stimuli-Responsive Behavior

ω-Hydroxytetradecanoic acid (ω-HOC14), prepared via an efficient yeast-catalyzed ω-hydroxylation of the corresponding fatty acid, was converted in two steps to the polymerizable zwitteronic surfactant ω-O-maleate-α-2-dimethyl­aminoethyl tetradecanamide (DMTA). Emulsion polymerizations of styrene with DMTA, bearing carboxylic and tertiary amine groups at the ω- and α-positions, were conducted in different pH environments. Emulsion polymerizations were most successful (particle diameters 9) conditions. In the pH range of 4–9, aggregation occurred; however, by adjustment of the pH to either acidic or basic conditions, partial redispersion occurred highlighting DMTA’s ability to provide stimuli-responsive colloidal behavior. Unexpectedly, upon drying the latex formed at pH = 3.1, a membrane with nanodimension pores was formed.