A novel water-soluble hydrophobically associating polyacrylamide based on oleic imidazoline and sulfonate for enhanced oil recovery

Abstract

3-(2-(2-Heptadec-8-enyl-4,5-dihydro-imidazol-1-yl)ethylcarbamoyl)acrylic acid (NIMA), 3-(diallyl-amino)-2hydroxypropyl sulfonate (NDS), acrylamide (AM) and acrylic acid (AA) were successfully utilized to prepare novel acrylamide-based copolymers (named AM/AA/NIMA and AM/AA/NDS/NIMA) which were functionalized by a combination of imidazoline derivative and/or sulfonate via redox free-radical polymerization. The two copolymers were characterized by infrared (IR) spectroscopy, 1 H nuclear magnetic resonance ( 1 H NMR), viscosimetry, pyrene fluorescence probe, thermogravimetry (TG) and differential thermogravimetry (DTG). As expected, the polymers exhibited excellent thickening property, shear stability (viscosity retention rate 5.02% and 7.65% at 1000 s À1 ) and salt-tolerance (10 000 mg L À1 NaCl: viscosity retention rate up to 17.1% and 10.2%) in comparison with similar concentration partially hydrolyzed polyacrylamide (HPAM). The temperature resistance of the AM/AA/NDS/NIMA solution was also remarkably improved and the viscosity retention rate reached 54.8% under 110 1C. According to the core flooding tests, oil recovery could be enhanced by up to 15.46% by 2000 mg L À1 of the AM/AA/ NDS/NIMA brine solution at 80 1C. † Electronic supplementary information (ESI) available: Synthesis routes, and their initial 1 H NMR spectrogram analysis of NDS and NIMA; solution preparation and characterization; fluorescence spectra of different concentrations of copolymer solutions; the composition of synthesized brine for dissolving polymer particle samples in the rheological experiments. See

Hyper-branched structure—an active carrier for copolymer with surface activity, anti-polyelectrolyte effect and hydrophobic association in enhanced oil recovery

“…In our previous works, we prepared a hydrophobically associating polyacrylamide based on oleic imidazoline and sulfonate, 34 an anti-biodegradable hydrophobic sulfonate-based acrylamide copolymer containing 2,4-dichlorophenoxy, 35 an ɑaminophosphonic acid-modied acrylamide-based hydrophobic-associating copolymer 36 and complexes of hydrophobically modied polymer and surface active imidazoliumbased ionic liquids, 37 which all showed gratifying results in enhanced oil recovery, providing strong evidence for the excellent properties of hydrophobic associations and ionic polymers. Based on these results, we made a new attempt to prepare a comb-shaped polyzwitterion with surface-activity via a Nmaleoyl chitosan modied HPAM, the surface tension decreased with the increase of polymer solution concentration within a certain range, this discovery had a great positive meaning on overcoming the chromatographic separation effect and reducing the oil-water interfacial tension to improve oil recovery, also introduced comb-shaped model in copolymer structure.…”

Inverse emulsion polymerization of triple monomers of acrylamide, maleic anhydride, and styrene to achieve highly hydrophilic–hydrophobic modified polyacrylamide

“…Table shows the critical apparent viscosity and concentration for the copolymer and terpolymers at different temperatures. By changing the concentration, this drastic change shifted to the higher viscosity for each polymer, styrene hydrophobic interactions in the hydrosoluble skeleton started to self‐aggregate into hydrophobic microdomains, formation of physical crosslinks between the mainchains, consequently, a sudden increment in the viscosity is observed . Indeed, when the concentration of the polymer exceeded a critical value (C * ), the presence of hydrophobic styrene monomers in the hydrophilic main chain led to some intermolecular interactions in the structure of these types of polymers, the formation of a three‐dimensional (3D) grid structure and finally make super‐molecular masses.…”

Hydrophobically associating polymers for enhanced oil recovery – Part B: A review of modelling approach to flow in porous media

“…Below the CAC, intramolecular interaction within the polymer chain dominates the rheology (Taylor and Nasr El-Din, 1998;Yabin et al, 2001;Feng et al, 2005;Lu et al, 2010;Afolabi, 2015;Akbulut and Temizel, 2017;Afolabi et al, 2019). Under these conditions, hydrodynamic volume is low with no network formation between polymer chains resulting in low polymer viscosity (Taylor and Nasr El-Din, 1998;Yabin et al, 2001;Zeynali et al, 2004;Taghizadeh and Foroutan, 2005;Romero, 2009;Alquraishi and Alsewailem, 2012;Gou et al, 2015;El-Hoshoudy et al, 2017;Bai et al, 2018). This particular phase is described as the "dilute region".…”

“…This particular phase is described as the "dilute region". Beyond the CAC, intermolecular association arising from hydrophobic interactions between polymer chains dominates the rheological behaviour of aqueous solutions formulated from HAPAM (Gou et al, 2015;Sun et al, 2015;Chen, 2016;Bai et al, 2018). This brings about a network of molecular association between the polymer chains, which in turn increase the hydrodynamic volume and viscosity.…”