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

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journal contribution
posted on 06.02.2019, 18:18 by Jing Hu, Connor Sanders, Shekar Mekala, Tzu-Yin Chen, Michael F. Cunningham, Richard A. Gross
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 <80 nm, high styrene conversion) under basic conditions (pH 9.8 and 11.0), where latex samples have highly negative zeta potentials (−40.4 to −46.0 mV). Because of the zwitterionic nature of the surfactant, transparent or semitransparent latexes were obtained under either acidic (pH < 4) or basic (pH > 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.

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