Amino acid-based surfactants

Infante, M. R.; Pérez, Lourdes; Pinazo, Aurora; Clapés, Pere; Morán, María Carmen; Angelet, Marta; Garcı́a, Marı́a Teresa; Vinardell, M. Pilar

doi:10.1016/j.crci.2004.02.009

Cited by 145 publications

(53 citation statements)

References 49 publications

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“…This allows a more compact organisation at the interface and thus a higher surface concentration which is directly linked to surface tension. Similar tendencies have been frequently reported in the literature [22][23][24].…”

Section: Influence Of the Chain Length Of The Fatty Acid (8 12 Or 14)supporting

confidence: 90%

Surface properties of new virginiamycin M1 derivatives

Nott

Paquot

Dufour

et al. 2009

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tThree kinds of derivatives of the M 1 factor of virginiamycin have been synthesised: esters with long chain fatty acids, oximes with modified polar amino acids and bis-derivatives with both the ester and oxime function. The study of the surface tension time dependence of M 1 and its derivatives has shown that it is necessary to enhance simultaneously the hydrophobicity and the hydrophilicity of M 1 to render M 1 surface-active. A structure/function relationship study of the surface-active bis-derivatives has shown that enhancing the hydrophobicity of the molecule led to slower adsorption kinetics, higher stability of the monolayers formed and a better capacity to penetrate a membrane model. The repulsive electrostatic forces due to the presence of charges on the amino acids linked to M 1 lead to higher surface tensions, a greater molecular area at the interface and lower penetration into a membrane model. This study has demonstrated that modifying systematically the hydrophobicity and hydrophilicity of a non surface-active molecule allows the production of surface-active derivatives.

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Section: Influence Of the Chain Length Of The Fatty Acid (8 12 Or 14)supporting

confidence: 90%

Surface properties of new virginiamycin M1 derivatives

Nott

Paquot

Dufour

et al. 2009

Colloids and Surfaces B: Biointerfaces

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“…On the other hand, anionic surfactants are used as detergents, and then the interaction of anionic surfactants with phospholipid vesicles might be a good research model for the influence of detergent on skin [18][19][20][21] . Particularly Nacyl amino acids, which are anionic amino acid-type surfactants, are very valuable because of their biodegradability and low toxicity 22,23) . In spite of the interest in their low toxicity, there are few studies on the interaction between amino acid-type surfactants and phospholipid vesicles from the standpoint of their physicochemical properties, except for those concerning their antimicrobial activity [24][25][26] .…”

Section: Introductionmentioning

confidence: 99%

Effect of Functional Groups on Incorporation Behavior of Amino Acid-Type Surfactant into Phospholipid Vesicle Membrane

et al. 2009

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The incorporation behaviors of some N-dodecanoyl amino acid-type surfactants into L-adipalmitoylphosphatidylcholine (DPPC) vesicles in aqueous solution were investigated. From the leakage measurements of a vesicle-entrapped fluorescence probe, it was found that these surfactants did not affect the DPPC vesicle so much at a very low concentration less than a one-tenth of the critical micelle concentration (CMC), but caused a significant release of the probe form the vesicles even at just below the CMC. The leakage induced by amino acid-type surfactants was promoted by increasing hydrophobicity of the amino acid. However the polarization of DPH embedded in the DPPC membrane was almost unchanged by incorporation of the surfactants at the concentration below the CMC except for the Ndodecanoylphenylalanine system. The binding enthalpy and the binding constant of the surfactant to DPPC vesicles were estimated by isothermal titration calorimetry. While the binding enthalpy was independent of the kind of surfactant, the binding constant increases with increasing hydrophobicity of the amino acid species in the surfactants. The molar ratio of bound surfactant to DPPC molecule in the saturated state was much greater than that for sodium dodecyl sulfate system. Further the ratio was not influenced by the structure of the amino acid side chain.

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“…They are now very commonly used in house cleaning products [4,5], food industry, pharmaceutical applications, and foam flotation, textile and leather industry, but seldom in oil recovery.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of diacyl amino acid surfactant and evaluation of its potential for surfactant–polymer flooding

Ren

Shi

Song³

et al. 2015

Appl Petrochem Res

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Diacyl amino acid surfactant was prepared using lauroyl chloride and L-lysine. The structure of the synthesized surfactant was confirmed by infrared spectroscopy and mass spectroscopy. The ultralow interfacial tension could be achieved when the diacyl amino acid surfactant is mixed with sulfonate in the presence of polymer as well as absence of polymer. Core flood experiments showed that 17.8 % additional oil could be recovered by injection of 0.3 pore volume of surfactantpolymer solution, making the total oil recovery reach 66.1 %.

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Amino acid-based surfactants

Cited by 145 publications

References 49 publications

Surface properties of new virginiamycin M1 derivatives

Surface properties of new virginiamycin M1 derivatives

Effect of Functional Groups on Incorporation Behavior of Amino Acid-Type Surfactant into Phospholipid Vesicle Membrane

Synthesis of diacyl amino acid surfactant and evaluation of its potential for surfactant–polymer flooding

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