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Progress in synthesis and application of zwitterionic Gemini surfactants |
Yuqiao CHENG1(), Yang YANG1, Chunrong NIU2, Zhe FENG1, Wenhui ZHAO1, Shuang LU1 |
1. School of Chemistry and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300387, China 2. Library, Tianjin Polytechnic University, Tianjin 300387, China |
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Abstract Zwitterionic Gemini surfactants have the Gemini molecular structure in which there are both multiple lipophilic groups and multiple hydrophilic groups. However, their hydrophilic groups have different charges. Due to the special molecular structure, this kind of surfactants possesses excellent properties, including high surface activities, isoelectric point (IP), low critical micelle concentration (CMC), less toxicity, low irritating, biodegradability, bioactive, interface modification, and so on. In this review, synthetic strategies of three kinds of zwitterionic Gemini surfactants, i.e., anionic– cationic, cationic–nonionic and anionic–nonionic Gemini surfactants, are discussed, and their potential applications in life sciences, chemical industry and enhanced oil recovery (EOR) are illustrated. Their future development is also prospected.
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Keywords
zwitterionic Gemini surfactant
high performance
synthesis; application
chemical industry
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Corresponding Author(s):
Yuqiao CHENG
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Online First Date: 11 September 2019
Issue Date: 29 September 2019
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1 |
C A Bunton, L Robinson, J Schaak, et al.. Catalysis of nucleophilic substitutions by micelles of dicationic detergents. Journal of Organic Chemistry, 1971, 36(16): 2346–2350
https://doi.org/10.1021/jo00815a033
|
2 |
F M Menger, C A Littau. Gemini surfactants: Synthesis and properties. Journal of the American Chemical Society, 1991, 113(4): 1451–1452
https://doi.org/10.1021/ja00004a077
|
3 |
N Kumar, R Tyagi. Industrial applications of dimeric surfactants: A review. Journal of Dispersion Science and Technology, 2014, 35(2): 205–214
https://doi.org/10.1080/01932691.2013.780243
|
4 |
M Ao, G Xu, J Pang, et al.. Comparison of aggregation behaviors between ionic liquid-type imidazolium Gemini surfactant [C12-4-C12im]Br2 and its monomer [C12mim]Br on silicon wafer. Langmuir, 2009, 25(17): 9721–9727
https://doi.org/10.1021/la901005v
pmid: 19555107
|
5 |
Z Huang, C Cheng, Z Liu, et al.. Gemini surfactant: A novel flotation collector for harvesting of microalgae by froth flotation. Bioresource Technology, 2019, 275: 421–424
https://doi.org/10.1016/j.biortech.2018.12.106
pmid: 30611623
|
6 |
J M Liu, X Y Ma, S J Zhang, et al.. Cationic gemini surfactant templated magnetic cubic mesoporous silica and its application in the magnetic dispersive solid phase extraction of endocrine-disrupting compounds from the migrants of food contact materials. Microchemical Journal, 2019, 145: 606–613
https://doi.org/10.1016/j.microc.2018.11.013
|
7 |
S Zhang, T Xu, Q Liu, et al.. Cationic gemini surfactant-resorcinol-aldehyde resin and its application in the extraction of endocrine disrupting compounds from food contacting materials. Food Chemistry, 2019, 277: 407–413
https://doi.org/10.1016/j.foodchem.2018.10.132
pmid: 30502164
|
8 |
R Sharma, A Kamal, M Abdinejad, et al.. Advances in the synthesis, molecular architectures and potential applications of Gemini surfactants. Advances in Colloid and Interface Science, 2017, 248: 35–68
https://doi.org/10.1016/j.cis.2017.07.032
pmid: 28800974
|
9 |
S M S Hussain, L T Fogang, M S Kamal. Synthesis and performance evaluation of betaine type zwitterionic surfactants containing different degrees of ethoxylation. Journal of Molecular Structure, 2018, 1173: 983–989
https://doi.org/10.1016/j.molstruc.2018.07.069
|
10 |
C L Xue, H L Zhu, T T Zhang, et al.. Synthesis and properties of novel alkylbetaine zwitterionic gemini surfactants derived from cyanuric chloride. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2011, 375(1–3): 141–146
https://doi.org/10.1016/j.colsurfa.2010.12.004
|
11 |
P Li, C Yang, Z Cui, et al.. A new type of sulfobetaine surfactant with double alkyl polyoxyethylene ether chains for enhanced oil recovery. Journal of Surfactants and Detergents, 2016, 19(5): 967–977
https://doi.org/10.1007/s11743-016-1839-2
|
12 |
A Muggeridge, A Cockin, K Webb, et al.. Recovery rates, enhanced oil recovery and technological limits. Philosophical Transactions of the Royal Society A: Mathematical Physical and Engineering Sciences, 2014, 372(2006): 20120320
https://doi.org/10.1098/rsta.2012.0320
|
13 |
A A Olajire. Review of ASP EOR (alkaline surfactant polymer enhanced oil recovery) technology in the petroleum industry: Prospects and challenges. Energy, 2014, 77(SI): 963–982
https://doi.org/10.1016/j.energy.2014.09.005
|
14 |
Z H Ren, D J Chen, Y Luo. Adsorption of amino sulfonate amphoteric surfactants on quartz sand. China Surfactant Detergent & Cosmetics, 2010, 40(6): 410–413 (in Chinese)
|
15 |
A T Guttmann. Sulfoalkylated imidazolines. US Patent, 3244724, 1966-04-05
|
16 |
T Yoshimura, T Ichinokawa, M Kaji, et al.. Synthesis and surface-active properties of sulfobetaine-type zwitterionic gemini surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2006, 273(1–3): 208–212
https://doi.org/10.1016/j.colsurfa.2005.08.023
|
17 |
M Hirao, K Ito-Akita, H Ohno. Polymerization of molten salt monomers having a phenylimidazolium group. Polymers for Advanced Technologies, 2000, 11(8–12): 534–538
https://doi.org/10.1002/1099-1581(200008/12)11:8/12<534::AID-PAT2>3.0.CO;2-R
|
18 |
M Hirao, H Sugimoto, H Ohno. Preparation of novel room-temperature molten salts by neutralization of amines. Journal of the Electrochemical Society, 2000, 147(11): 4168–4172
https://doi.org/10.1149/1.1394036
|
19 |
M Hirao, K Ito, H Ohno. Preparation and polymerization of new organic molten salts; N-alkylimidazolium salt derivatives. Electrochimica Acta, 2000, 45(8–9): 1291–1294
https://doi.org/10.1016/S0013-4686(99)00334-5
|
20 |
Y C Zheng, Z H Ren, P Mei, et al.. Interactions between a sulfobetaine-type zwitterionic Gemini surfactant and fatty acid alkanolamide in aqueous micellar solution. Journal of Surfactants and Detergents, 2016, 19(2): 283–288
https://doi.org/10.1007/s11743-016-1786-y
|
21 |
K Nyuta, T Yoshimura, K Esumi. Surface tension and micellization properties of heterogemini surfactants containing quaternary ammonium salt and sulfobetaine moiety. Journal of Colloid and Interface Science, 2006, 301(1): 267–273
https://doi.org/10.1016/j.jcis.2006.04.075
pmid: 16730355
|
22 |
D V Perroni, M K Mahanthappa. Inverse Pm3 ¯n cubic micellar lyotropic phases from zwitterionic triazolium Gemini surfactants. Soft Matter, 2013, 9(33): 7919–7922
https://doi.org/10.1039/c3sm51238j
|
23 |
M Yoshizawa, M Hirao, K Ito-Akita, et al.. Ion conduction in zwitterionic-type molten salts and their polymers. Journal of Materials Chemistry, 2001, 11(4): 1057–1062
https://doi.org/10.1039/b101079o
|
24 |
J Feng, X P Liu, L Zhang, et al.. Dilational viscoelasticity of the zwitterionic Gemini surfactants with polyoxyethylene spacers at the interfaces. Journal of Dispersion Science and Technology, 2011, 32(11): 1537–1546
https://doi.org/10.1080/01932691.2010.516139
|
25 |
X F Geng, X Q Hu, J J Xia, et al.. Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic Gemini surfactants. Applied Surface Science, 2013, 271: 284–290
https://doi.org/10.1016/j.apsusc.2013.01.185
|
26 |
G M Qu, X Q Hu, J J Xia. Study on synthesis and properties of sulfonate zwitterionic Gemini surfactants. In: Chinese Chemical Society. The 30th Annual Meeting of the Chinese Chemical Society - 31st Chapter: Colloids and Interface Chemistry, 2016, 1
|
27 |
R Bordes, K Holmberg. Amino acid-based surfactants — do they deserve more attention? Advances in Colloid and Interface Science, 2015, 222: 79–91
https://doi.org/10.1016/j.cis.2014.10.013
pmid: 25846628
|
28 |
Z F Xie, Y J Feng. Synthesis and properties of alkylbetaine zwitterionic Gemini surfactants. Journal of Surfactants and Detergents, 2010, 13(1): 51–57
https://doi.org/10.1007/s11743-009-1152-4
|
29 |
H Lu, M Xue, B Wang, et al.. pH-Regulated surface property and pH-reversible micelle transition of a tertiary amine-based Gemini surfactant in aqueous solution. Soft Matter, 2015, 11(47): 9135–9143
https://doi.org/10.1039/C5SM01990G
pmid: 26411356
|
30 |
H Lu, C Zheng, M Xue, et al.. pH-Regulated surface properties and pH-reversible micelle transition of a zwitterionic Gemini surfactant in aqueous solution. Physical Chemistry Chemical Physics, 2016, 18(47): 32192–32197
https://doi.org/10.1039/C6CP06599F
pmid: 27849081
|
31 |
M Zhou, G Luo, X W Wang, et al.. Synthesis and surface active properties of tri[(N-alkyl-N-ethyl-N-sodium carboxymethyl)-2-ammonium bromide ethylene] amines. Journal of Surfactants and Detergents, 2015, 18(5): 837–844
https://doi.org/10.1007/s11743-015-1716-4
|
32 |
M Zhou, Z Huang, S Yu, et al.. Synthesis and surface active properties of novel oligomer betaine surfactants. Tenside, Surfactants, Detergents, 2016, 53(2): 134–139
https://doi.org/10.3139/113.110418
|
33 |
D A Jaeger, B Li, T Clark. Cleavable double-chain surfactants with one cationic and one anionic head group that form vesicles. Langmuir, 1996, 12(18): 4314–4316
https://doi.org/10.1021/la960012r
|
34 |
K Nyuta, T Yoshimura, K Tsuchiya, et al.. Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups 2: aggregation behavior studied by SANS, DLS, and cryo-TEM. Journal of Colloid and Interface Science, 2012, 370(1): 80–85
https://doi.org/10.1016/j.jcis.2011.12.027
pmid: 22261272
|
35 |
T Yoshimura, K Nyuta, K Esumi. Zwitterionic heterogemini surfactants containing ammonium and carboxylate headgroups. 1. Adsorption and micellization. Langmuir, 2005, 21(7): 2682–2688
https://doi.org/10.1021/la047773b
pmid: 15779935
|
36 |
B B Nayak, S Patel, P K Behera, et al.. A novel class of zwitterionic Gemini surfactants. ARKIVOC, 2006, 14: 22–27
|
37 |
T Zhou, J Zhao. Synthesis and thermotropic liquid crystalline properties of heterogemini surfactants containing a quaternary ammonium and a hydroxyl group. Journal of Colloid and Interface Science, 2009, 331(2): 476–483
https://doi.org/10.1016/j.jcis.2008.11.056
pmid: 19101677
|
38 |
T Zhou, J Zhao. Synthesis and thermotropic liquid crystalline properties of zwitterionic gemini surfactants containing a quaternary ammonium and a sulfate group. Journal of Colloid and Interface Science, 2009, 338(1): 156–162
https://doi.org/10.1016/j.jcis.2009.06.009
pmid: 19564026
|
39 |
A V Peresypkin, F M Menger. Zwitterionic geminis. Coacervate formation from a single organic compound. Organic Letters, 1999, 1(9): 1347–1350
https://doi.org/10.1021/ol990205g
|
40 |
A Kumar, E Alami, K Holmberg, et al.. Branched zwitterionic gernini surfactants micellization and interaction with ionic surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2003, 228(1–3): 197–207
https://doi.org/10.1016/S0927-7757(03)00300-5
|
41 |
W H Ansari, S Noori, A Z Naqvi, et al.. Interaction between zwitterionic surfactants and amphiphilic drug: A tensiometric study. Zeitschrift für Physikalische Chemie - International Journal of Research in Physical Chemistry & Chemical Physics, 2013, 227(4): 441–458
https://doi.org/10.1524/zpch.2012.0340
|
42 |
M Mobin, S Noori. Adsorption and corrosion inhibition behaviour of zwitterionic Gemini surfactant for mild steel in 0.5 M HCl. Tenside, Surfactants, Detergents, 2016, 53(4): 357–367
https://doi.org/10.3139/113.110442
|
43 |
Y Sun, Y Feng, H Dong, et al.. Synthesis and aqueous solution properties of homologous Gemini surfactants with different head groups. Central European Journal of Chemistry, 2007, 5(2): 620–634
https://doi.org/10.2478/s11532-006-0072-7
|
44 |
Z Dong, Y Zheng, J Zhao. Synthesis, physico-chemical properties and enhanced oil recovery flooding evaluation of novel zwitterionic Gemini surfactants. Journal of Surfactants and Detergents, 2014, 17(6): 1213–1222
https://doi.org/10.1007/s11743-014-1616-z
|
45 |
Y R Li, B Cao, W Ye. Study on the synthetic process of new type of hydroxyl-containing phosphonate quaternary ammonium salt amphoteric surfactant. Speciality Petrochemicals, 1991, (6): 14–17 (in Chinese)
|
46 |
D Q Feng, G Liu, G Ma, et al.. Phosphodiesters quaternary ammonium nanoparticles as label-free light scattering probe for turn-off detection of tyrosine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, 208: 1–6
https://doi.org/10.1016/j.saa.2018.09.043
pmid: 30278308
|
47 |
X Chen, S Liang, L Zhu, et al.. High-sensitivity determination of curcumin in human urine using gemini zwitterionic surfactant as a probe by resonance light scattering technique. Phytochemical Analysis, 2012, 23(5): 456–461
https://doi.org/10.1002/pca.1380
pmid: 22190333
|
48 |
R A Cherkasov, V I Galkin. The Kabachnik–Fields reaction: synthetic potential and the problem of the mechanism. Russian Chemical Reviews, 1998, 67(10): 857–882
https://doi.org/10.1070/RC1998v067n10ABEH000421
|
49 |
T Yoshimura, K Nyuta. Dynamic surface tension of heterogemini surfactants with quaternary ammonium salt and gluconamide or sulfobetaine headgroups. Journal of Oleo Science, 2017, 66(10): 1139–1147
https://doi.org/10.5650/jos.ess17021
pmid: 28924079
|
50 |
O Rist, A Rike, L Ljones, et al.. Synthesis of novel diammonium gemini surfactants. Molecules, 2001, 6(12): 979–987
https://doi.org/10.3390/61200979
|
51 |
K Nyuta, T Yoshimura, K Tsuchiya, et al.. Adsorption and aggregation properties of heterogemini surfactants containing a quaternary ammonium salt and a sugar moiety. Langmuir, 2006, 22(22): 9187–9191
https://doi.org/10.1021/la061688h
pmid: 17042528
|
52 |
J X Zhang, Y P Zheng, P Y Yu, et al.. Synthesis, characterization and surface-activity of a polyoxyethylene ether trimeric quater-nary ammonium surfactant. Journal of Surfactants and Detergents, 2010, 13(2): 155–158
https://doi.org/10.1007/s11743-009-1166-y
|
53 |
P Renouf, C Mioskowski, L Lebeau, et al.. Dimeric surfactants: First synthesis of an asymmetrical gemini compound. Tetrahedron Letters, 1998, 39(11): 1357–1360
https://doi.org/10.1016/S0040-4039(97)10835-8
|
54 |
E Alami, K Holmberg, J Eastoe. Adsorption properties of novel gemini surfactants with nonidentical head groups. Journal of Colloid and Interface Science, 2002, 247(2): 447–455
https://doi.org/10.1006/jcis.2001.8116
pmid: 16290486
|
55 |
C C Lai, K M Chen. Preparation and surface activity of polyoxyethylene-carboxylated modified Gemini surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, 320(1–3): 6–10
https://doi.org/10.1016/j.colsurfa.2007.12.056
|
56 |
Z Shen, Y Li, O Sha, et al.. Synthesis and properties of nonionic–anionic gemini surfactants with high activity. Advances in Fine Petrochemicals, 2011, 12(09): 25–29
|
57 |
E A Egan, R H Notter, M S Kwong, et al.. Natural and artificial lung surfactant replacement therapy in premature lambs. Journal of Applied Physiology: Respiratory, Environmental and Exercise Physiology, 1983, 55(3): 875–883
https://doi.org/10.1152/jappl.1983.55.3.875
pmid: 6556192
|
58 |
A Z Naqvi, S Noori, Kabir-ud-Din. Effect of surfactant structure on the mixed micelle formation of cationic gemini-zwitterionic phospholipid systems. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2015, 477: 9–18
https://doi.org/10.1016/j.colsurfa.2015.03.009
|
59 |
S Noori, A Z Naqvi, W H Ansari, et al.. Effect of asymmetric dimeric zwitterionic surfactants on micellization behavior of amphiphilic drugs. Journal of Solution Chemistry, 2015, 44(6): 1292–1309
https://doi.org/10.1007/s10953-015-0338-9
|
60 |
Z Qu. Applications of H-phosphonates in synthesis of phosphorus-containing functional compounds. Dissertation for the Doctoral Degree. Zhengzhou, China: Zhengzhou University, 2012 (in Chinese)
|
61 |
M Lukác, J Mojzis, G Mojzisová, et al.. Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity. European Journal of Medicinal Chemistry, 2009, 44(12): 4970–4977
https://doi.org/10.1016/j.ejmech.2009.08.011
pmid: 19762125
|
62 |
R G Strickley. Solubilizing excipients in oral and injectable formulations. Pharmaceutical Research, 2004, 21(2): 201–230
https://doi.org/10.1023/B:PHAM.0000016235.32639.23
pmid: 15032302
|
63 |
M Blanzat, E Perez, I Rico-Lattes, et al.. New catanionic glycolipids. 1. Synthesis, characterization, and biological activity of double-chain and Gemini catanionic analogues of galactosylceramide (galβ1cer). Langmuir, 1999, 15(19): 6163–6169
|
64 |
F Wang, S Hu. Direct electron-transfer of myoglobin within a new zwitterionic gemini surfactant film and its analytical application for H2O2 detection. Colloids and Surfaces B: Biointerfaces, 2008, 63(2): 262–268
https://doi.org/10.1016/j.colsurfb.2007.12.020
pmid: 18321683
|
65 |
M Tiecco, G Cardinali, L Roscini, et al.. Biocidal and inhibitory activity screening of de novo synthesized surfactants against two eukaryotic and two prokaryotic microbial species. Colloids and Surfaces B: Biointerfaces, 2013, 111: 407–417
https://doi.org/10.1016/j.colsurfb.2013.06.033
pmid: 23856545
|
66 |
H Choi, T Liu, H Qiao, et al.. Biomimetic nano-surfactant stabilizes sub-50 nanometer phospholipid particles enabling high paclitaxel payload and deep tumor penetration. Biomaterials, 2018, 181: 240–251
https://doi.org/10.1016/j.biomaterials.2018.07.034
pmid: 30096559
|
67 |
R Kaur, S Kumar, V K Aswal, et al.. Influence of headgroup on the aggregation and interactional behavior of twin-tailed cationic surfactants with pluronics. Langmuir, 2013, 29(38): 11821–11833
https://doi.org/10.1021/la401864p
pmid: 23978237
|
68 |
X C Wang, X Q Wang, T T Qing. The application of Gemini surfactant in leather industry. Leather Science and Engineering, 2015, 25(3): 32–37 (in Chinese)
|
69 |
M Cai, M Zhang, P Ma. Synthesis and applications of alkylbenzene sulfonate gemini surfactants. Journal of Dispersion Science and Technology, 2010, 31(12): 1633–1637
https://doi.org/10.1080/01932690903297389
|
70 |
P Fischer, H Wu. Morphological transitions in dilute solutions of sugar-based zwitterionic dimer betaine surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2008, 326(1–2): 103–108
https://doi.org/10.1016/j.colsurfa.2008.05.031
|
71 |
K Chen, D C Locke, T Maldacker, et al.. Separation of ergot alkaloids by micellar electrokinetic capillary chromatography using cationic Gemini surfactants. Journal of Chromatography A, 1998, 822(2): 281–290
https://doi.org/10.1016/S0021-9673(98)00672-4
pmid: 9914656
|
72 |
P Van der Voort, E F Vansant. The synthesis of stable, hydrophobic MCM-48/VOx catalysts, using alkylchlorosilanes as coupling agents for the molecular designed dispersion of VO(acac)2. Microporous and Mesoporous Materials, 2000, 38(2–3): 385–390
https://doi.org/10.1016/S1387-1811(00)00166-9
|
73 |
S Chen, H Liu, H Sun, et al.. Synthesis and physiochemical performance evaluation of novel sulphobetaine zwitterionic surfactants from lignin for enhanced oil recovery. Journal of Molecular Liquids, 2018, 249: 73–82
https://doi.org/10.1016/j.molliq.2017.11.021
|
74 |
N Pal, N Saxena, A Mandal. Synthesis, characterization, and physicochemical properties of a series of quaternary Gemini surfactants with different spacer lengths. Colloid & Polymer Science, 2017, 295(12): 2261–2277
https://doi.org/10.1007/s00396-017-4199-1
|
75 |
F Shehzad, I A Hussein, M S Kamal, et al.. Polymeric surfactants and emerging alternatives used in the demulsification of produced water: A review. Polymer Reviews, 2018, 58(1): 63–101
https://doi.org/10.1080/15583724.2017.1340308
|
76 |
J Lu, A Goudarzi, P Chen, et al.. Enhanced oil recovery from high-temperature, high-salinity naturally fractured carbonate reservoirs by surfactant flood. Journal of Petroleum Science and Engineering, 2014, 124: 122–131
https://doi.org/10.1016/j.petrol.2014.10.016
|
77 |
S M S Hussain, M S Kamal, L T Fogang. Effect of internal olefin on the properties of betaine-type zwitterionic surfactants for enhanced oil recovery. Journal of Molecular Liquids, 2018, 266: 43–50
https://doi.org/10.1016/j.molliq.2018.06.031
|
78 |
M Tagavifar, K Xu, S H Jang, et al.. Spontaneous and flow-driven interfacial phase change: dynamics of microemulsion formation at the pore scale. Langmuir, 2017, 33(45): 13077–13086
https://doi.org/10.1021/acs.langmuir.7b02856
pmid: 29052996
|
79 |
M Madani, G Zargar, M A Takassi, et al.. Fundamental investigation of an environmentally-friendly surfactant agent for chemical enhanced oil recovery. Fuel, 2019, 238: 186–197
https://doi.org/10.1016/j.fuel.2018.10.105
|
80 |
M A Takassi, G Zargar, M Madani, et al.. The preparation of an amino acid-based surfactant and its potential application as an EOR agent. Petroleum Science and Technology, 2017, 35(4): 385–391
https://doi.org/10.1080/10916466.2016.1238933
|
81 |
S S Shadizadeh, R Kharrat. Experimental investigation of matricaria chamomilla extract effect on oil–water interfacial tension: usable for chemical enhanced oil recovery. Petroleum Science and Technology, 2015, 33(8): 901–907
https://doi.org/10.1080/10916466.2015.1020063
|
82 |
A M Al-Sabagh. Surface activity and thermodynamic properties of water-soluble polyester surfactants based on 1,3-dicarboxymethoxybenzene used for enhanced oil recovery. Polymers for Advanced Technologies, 2000, 11(1): 48–56
https://doi.org/10.1002/(SICI)1099-1581(200001)11:1<48::AID-PAT936>3.0.CO;2-9
|
83 |
X C Cao, Y Y Li, K Ke. Research progress in application of surfactants in petroleum engineering. Contemporary Chemical Industry, 2017, 46(6): 1222–1224, 1234 (in Chinese)
|
84 |
M S Kamal, I A Hussein, A S Sultan. Review on surfactant flooding: phase behavior, retention, IFT, and field applications. Energy & Fuels, 2017, 31(8): 7701–7720
https://doi.org/10.1021/acs.energyfuels.7b00353
|
85 |
S Pal, M Mushtaq, F Banat, et al.. Review of surfactant-assisted chemical enhanced oil recovery for carbonate reservoirs: challenges and future perspectives. Petroleum Science, 2018, 15(1): 77–102
https://doi.org/10.1007/s12182-017-0198-6
|
86 |
P Raffa, A A Broekhuis, F Picchioni. Polymeric surfactants for enhanced oil recovery: A review. Journal of Petroleum Science Engineering, 2016, 145: 723–733
https://doi.org/10.1016/j.petrol.2016.07.007
|
87 |
H J Ren, W, Chen X H. Wang Synthesis and application performance of amphiprotic gemini surface active agent. Applied Chemical Industry, 2019, 48(3): 613‒615 (in Chinese)
|
88 |
L M Yan, J Ma, Y L Li, et al.. Surface and interfacial properties of 1,3-dialkyl glyceryl ether hydroxypropyl sulfonates as surfactants for enhanced oil recovery. Journal of Dispersion Science and Technology, 2018, 39(9): 1335–1343
https://doi.org/10.1080/01932691.2017.1402339
|
89 |
M Almahfood, B Bai. The synergistic effects of nanoparticle-surfactant nanofluids in EOR applications. Journal of Petroleum Science Engineering, 2018, 171: 196–210
https://doi.org/10.1016/j.petrol.2018.07.030
|
90 |
M Bracic, L Fras-Zemljic, K Kogej, et al.. Bioactive nano-coatings from hyaluronic acid and a lysine-derived surfactant. Abstracts of Papers of the American Chemical Society, 2017, 253: 480
|
91 |
X Chen, J B Liu, Y Chen. Properties of nano-CaCO3 modified by a serious of phosphate surfactants and their application in PVC. Journal of Southern Yangtze University (Natural Science Edition), 2002, 1(3): 266–268 (in Chinese)
|
92 |
M El Achouri, S Kertit, H M Gouttaya, et al.. Corrosion inhibition of iron in 1 M HCl by some gemini surfactants in the series of alkanediyl-α,ω-bis-(dimethyl tetradecyl ammonium bromide). Progress in Organic Coatings, 2001, 43(4): 267–273
https://doi.org/10.1016/S0300-9440(01)00208-9
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