Synthesis and solution properties of cationic gemini surfactants with long unsaturated tails

Li, Huazhen; Yang, Haiyang; Yan, Yuanyuan; Wang, Qin; He, Pingsheng

doi:10.1016/j.susc.2010.03.033

Cited by 12 publications

(12 citation statements)

References 28 publications

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“…Formally, geminis that are asymmetric (e.g., those with a lysine spacer) are classified as geminoid or gemini-like surfactans [ 36 , 37 ]. Hydrophobic fragments (tails) used in gemini surfactants vary in length (usually 8–20), structure (straight or branched chain) [ 38 ], and saturation [ 39 ]; tails can be fluorinated [ 40 ], contain poly(ethylene oxide) [ 41 ], cholesterol [ 42 ], or aromatic backbones [ 43 ]. Gemini surfactants are an intriguing group of compounds owing to their increased solubility in water, superior surface tension reduction power, reduced proximity between hydrophobic groups, lower critical micellar concentration (by one or more magnitudes), and superior wetting characteristics as compared to the corresponding single chain (monomeric) surfactants, which makes them convenient candidates for pharmaceuticals formulations [ 44 ].…”

Section: Introductionmentioning

confidence: 99%

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Neubauer

Jaśkiewicz

Bauer

et al. 2021

IJMS

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Ultrashort cationic lipopeptides (USCLs) and gemini cationic surfactants are classes of potent antimicrobials. Our recent study has shown that the branching and shortening of the fatty acids chains with the simultaneous addition of a hydrophobic N-terminal amino acid in USCLs result in compounds with enhanced selectivity. Here, this approach was introduced into arginine-rich gemini cationic surfactants. l-cystine diamide and l-lysine amide linkers were used as spacers. Antimicrobial activity against planktonic and biofilm cultures of ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) strains and Candida sp. as well as hemolytic and cytotoxic activities were examined. Moreover, antimicrobial activity in the presence of human serum and the ability to form micelles were evaluated. Membrane permeabilization study, serum stability assay, and molecular dynamics were performed. Generally, critical aggregation concentration was linearly correlated with hydrophobicity. Gemini surfactants were more active than the parent USCLs, and they turned out to be selective antimicrobial agents with relatively low hemolytic and cytotoxic activities. Geminis with the l-cystine diamide spacer seem to be less cytotoxic than their l-lysine amide counterparts, but they exhibited lower antibiofilm and antimicrobial activities in serum. In some cases, geminis with branched fatty acid chains and N-terminal hydrophobic amino acid resides exhibited enhanced selectivity to pathogens over human cells.

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Section: Introductionmentioning

confidence: 99%

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Neubauer

Jaśkiewicz

Bauer

et al. 2021

IJMS

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“…In Table , the α value of C25‐6‐C25 is 0.67 and that of counterion binding β is 0.33. Compared with the β value of 22:1‐6‐22:1, that of C25‐6‐C25 increases with an increasing tail length of surfactant. Zhu et al .…”

Section: Resultsmentioning

confidence: 87%

“…The results are shown in Table , which shows that the value of a min of C25‐6‐C25 is larger than that of 22:1‐6‐22:1 (0.75 nm 2 ) . A possible explanation for this is that longer hydrophobic chains are more prone to curling, thereby increasing the value of a min …”

Section: Resultsmentioning

confidence: 93%

“…The elemental analysis calculated for C 60 H 120 Br 2 N 4 O 2 was as follows: (C 66.25, H 11.13, N 5.15), found: (C 66.23, H 11.10, N 5.17). Figure (c) shows the 1 H NMR spectrum of C25‐6‐C25 in which all expected signals appeared as follows: 0.86 (t, 6H, CH 3 ), 1.24 (m, 56H, CH 2 ), 1.65–1.47 (m, 8H, COCCH 2 , spacer N + CCCH 2 ), 1.99 (dd, 16H, N + CCH 2 , CCCH 2 ), 2.26 (t, 4H, COCH 2 ), 3.26 (s, 12H, N + CH 3 ), 3.35 (t, 4H, spacer N + CH 2 ), 3.63 (t, 4H, N + CH 2 ), 3.78–3.68 (t, 4H, NCH 2 ), and 5.47–5.21 (t, 4H, HCCH), δ = 7.72 (br, 2H, NH) . Therefore, C25‐6‐C25 was successfully synthesized.…”

Section: Resultsmentioning

confidence: 99%

“…The CMC of C25‐6‐C25 is 32.96 μmol L −1 . Li et al . synthesized a similar gemini surfactant (22:1‐6‐22:1).…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Self‐assembly properties of ultra‐long‐chain gemini surfactant with high performance in a fracturing fluid application

Yang

Zhang

et al. 2016

J of Applied Polymer Sci

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A new cationic gemini surfactant (C25‐6‐C25), which had a special structure consisting of ultra‐long hydrophobic chains and amide groups, was synthesized using a main feedstock source obtained from rapeseed for thickening purposes. The 12 mmol L−1 C25‐6‐C25 fluid containing 0.19 mol L−1 potassium chloride (KCl) exhibited highly elastic properties at the angular frequency of 0.04–10 rad s−1. Its viscosity could be maintained at 55 mPa s for 1.5 h under a shear rate of 170 s−1 at 110 °C and it also showed a good proppant‐suspending property. C25‐6‐C25/KCl fluid exhibited high viscoelasticity and good performance, which were attributed to intermolecular forces, hydrogen bonding, and the shielding effect of electrostatic repulsion by KCl. Thus, C25‐6‐C25 is a very promising candidate for fracturing. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44602.

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A Review of Gemini Surfactants: Potential Application in Enhanced Oil Recovery

Kamal

2015

J Surfact & Detergents

268

151

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Gemini surfactants are a group of novel surfactants with more than one hydrophilic head group and hydrophobic tail group linked by a spacer at or near the head groups. Unique properties of gemini surfactants, such as low critical micelle concentration, good water solubility, unusual micelle structures and aggregation behavior, high efficiency in reducing oil/water interfacial tension, and interesting rheological properties have attracted the attention of academic researchers and field experts. Rheological characterization and determination of the interfacial tension are two of the most important screening techniques for the evaluation and selection of chemicals for enhanced oil recovery (EOR). This review deals with rheology, wettability alteration, adsorption and interfacial properties of gemini surfactants and various factors affecting their performance. The review highlights the current research activities on the application of gemini surfactants in EOR.

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Synthesis and solution properties of cationic gemini surfactants with long unsaturated tails

Cited by 12 publications

References 28 publications

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers

Self‐assembly properties of ultra‐long‐chain gemini surfactant with high performance in a fracturing fluid application

A Review of Gemini Surfactants: Potential Application in Enhanced Oil Recovery

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