Ionic liquid surfactants (ILSs) have
shown increasing promise for
substituting the traditional amphiphiles because of their flexible
tunability and advantageous physicochemical properties. However, the
improvement of common ILSs in terms of self-assembly ability and thickening
ability remains a significant challenge. Herein, two novel ultralong-chain
ILSs (ULILSs), ErBCho (choline cis-4-erucylamidobenzoate)
and ErBBTA (benzyltrimethylammonium cis-4-erucylamidobenzoate),
were designed and synthesized from natural unsaturated fatty acid
(erucic acid). Their structures were characterized via 1H NMR, 13C NMR, and electrospray ionization-mass spectrometry
techniques, and physicochemical properties were evaluated by surface
tension, polarized optical microscopy, and rheology. The insertion
of a phenyl ring between the charged headgroup and unsaturated C22-tail
significantly enhanced the hydrophobicity of ULILSs, but they retained
the desirable characteristics of ILSs (low melting temperature) and
excellent water-solubility (Krafft temperature <4 °C), for
application in low-temperature water. Compared with counterparts without
a phenyl ring, the critical micelle concentration (cmc) of the presented
ULILSs was markedly decreased by at least an order of magnitude (particularly
cmc of ErBBTA 3.5 μM), and interfacial activity was higher (larger
pC
20). In particular, the current ULILSs
were able to form wormlike micelles on their own and then thicken
the solution at relatively low overlapping concentrations (1.68–5.71
mM), without any additives and regardless of counterions. More importantly,
viscoelastic fluids formed by the current ULILSs (especially ErBBTA)
were not only resistant to high temperature and cycled shear but also
exhibited excellent sand-carrying and oil-induced gel-breaking performances.
Such ULILSs have shown promise to replace those common surfactants
in hydro-fracturing and other applications.