Two biobased polymerizable surfactants ?-acryltetradecanoic acid(MA-1) and ?-maleate tetradecanoicacid (MA-2) were synthesized from ?-hydroxytetradecanoic acid, which was prepared via an efficient yeast catalyzed ?-hydroxylation reaction. MA-1 is a single polar-headed surfactant whereas MA-2 is a bolaamphiphile with carboxylic acid polar groups at both chain ends. The surface tension test of surfactant solutions and experimental determination of the reactivity ratios for surfactants with styrene were conducted. Emulsion polymerizations with varying amounts of MA-1 and MA-2 (1-10 wt% with respect to styrene) gave colloidally stable latexes with particle sizes ranging from 52 nm to 155 nm. 1H-NMR and potentiometric titration were used to measure MA-1 and MA-2 polymerization conversions, as well as how the surfactants were distributed on the particle surface. Observed differences were rationalized based on the comparative structures of MA-1 and MA-2 and their corresponding partitioning behavior.                                                        

Biobased anionic polymerizable surfactants from ?-hydroxyfatty acids

248th National Meeting (2014)

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