1 research outputs found
Anionic Polymerizable Surfactants from Biobased ω‑Hydroxy Fatty Acids
Biobased ω-hydroxytetradecanoic
acid prepared via an efficient
yeast-catalyzed ω-hydroxylation reaction was converted by a
one-step reaction to the polymerizable surfactants ω-acryltetradecanoic
acid (MA-1) and ω-maleate tetradecanoic acid (MA-2). MA-1 is
a single polar-headed surfactant, whereas MA-2 is a bolaamphiphile
with carboxylic acid polar groups at both chain ends. MA-1 gave a
distinct critical micelle concentration (cmc) at 253 mg/L, whereas
for MA-2, the surface tension decreased monotonically and a distinct
cmc was not observed even up to 1800 mg/L. Experimental determination
of the reactivity ratios for MA-1 and MA-2 with styrene showed that
for MA-1 copolymers that approximate random structures were formed
while MA-2 tends to form copolymers with an alternating nature. Emulsion
polymerizations conducted 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 to 155 nm. In emulsion polymerizations
using either MA-1 or MA-2 at more than 5 wt % to monomer, a linear
increase in latex particle volume with conversion was observed and
the particle number remained constant, establishing that the polymerizations
proceeded without significant aggregation or secondary particle nucleation.
Potentiometric titration and <sup>1</sup>H NMR were used to measure
MA-1 and MA-2 conversions during polymerization as well as how the
surfactants were distributed between the particle surface, aqueous
phase, and particle interior. Observed differences were rationalized
based on the comparative structures of MA-1 and MA-2 and their corresponding
partitioning behavior