Natural surfactants

Current Opinion in Colloid and Interface Science

Volumn 6, Issue 2, 2001, Pages 148-159

  Holmberg, Krister ^a  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Amino acid; Biotechnology; Fatty acid; Natural; Polyol; Sterol; Sugar; Surfactant

Indexed keywords

ALKYL GROUP; AMINO ACID; AMPHOPHILE; ESTER; FATTY ACID; GLUCOSIDE; GLYCOLIPID; PEPTIDE; POLYOL; STEROL; SUGAR; SURFACTANT;

BACTERIUM; CHEMICAL STRUCTURE; ENVIRONMENTAL IMPACT ASSESSMENT; FERMENTATION; HYDROPHOBICITY; MOLECULAR WEIGHT; NONHUMAN; PHYSICAL CHEMISTRY; REVIEW; SYNTHESIS; YEAST;

EID: 0035004007     PISSN: 13590294     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0294(01)00074-7     Document Type: Review

References (55)

1. Kosaric N. Biosurfactants. Surfactant Science Series 48. 1993;Marcel Dekker, New York.
2. Halliday H.L. Controversies: synthetic or natural surfactant. The case for natural surfactant. J Perinatal Med. 24:1996;417-426.
3. Haferburg D., Hommel R., Claus R., Kleber H.-P. Extracellular microbial lipids as biosurfactants. Adv Biochem Eng/Biotechnol. 33:1986;53-93.
4. Weber L., Stach J., Haufe G., Hommel R., Kleber H.-P. Elucidation of the structure of an unusual cyclic glycolipid from Torulopsis apicola. Carbohydrate Res. 206:1990;13-19.
5. Guerra-Santos L.H., Kappeli O., Fiechter A. Dependence of Pseudomonas aeruginosa continuous culture biosurfactant production on nutritional and environmental factors. Appl Microbiol Biotechnol. 24:1986;443-448.
6. Sullivan E.R. Molecular genetics of biosurfactant production. Curr Opin Biotechnol. 9:1998;263-269.
7. Pruthi V., Cameotra S.S. Novel sucrose lipid produced by Serratia marcescens and its application in enhanced oil recovery. J Surf Det. 3:2000;533-537. •Sucrose lipids with excellent ability to emulsify hydrocarbons, including crude oil, were produced. The surfactant was a mixture of two hydroxyalkanoic acid esters of sucrose.
8. Zuber P., Nakano M.M., Marahiel M.A. Peptide antibiotics. Zuber P., Nakano M.M., Marahiel M.A. Bacillus subtilis and other gram-positive bacteria. 1993;897-916 American Society for Microbiology, Washington DC.
9. Sen R., Swaminathan T. Application of response-surface methodology to evaluate the optimal environmental conditions for the enhanced production of surfactin. Appl Microbiol Biotechnol. 47:1997;358-363.
10. Vollenbroich D., Ozel M., Vater J., Kamp R.M., Pauli G. Mechanism of inactivation of enveloped viruses by the biosurfactant surfactin from Bacillus subtilis. Biologicals. 25:1997;289-297.
11. Shinoda K., Carlsson A., Lindman B. On the importance of hydroxyl groups in the polar headgroup of nonionic surfactants and membrane lipids. Adv Colloid Interface Sci. 64:1996;253-271.
12. Garcia M.T., Ribosa I., Campos E., Leal J.S. Ecological properties of alkylglucosides. Chemosphere. 35:1997;545-556.
13. Uppgard L., Sjöström M. Multivariate quantitative structure-activity relationships for the aquatic toxicity of alkyl polyglucosides. Tenside Surf Det. 37:2000;131-138.
14. Busch P., Hensen H., Tesmann H. Alkylpolyglycoside-eine neue Tensidgeneration für die Kosmetik. Tenside Surf Det. 30:1993;116-121.
15. Hill K., von Rybinski W., Stoll G. Alkyl polyglycosides: technology, properties and applications. 1997;VCH, Weinheim, Germany.
16. von Rybinski W. Alkyl glycosides and polyglycosides. Curr Opin Colloid Interface Sci. 1:1996;597.
17. von Rybinski W., Hill K. Alkyl polyglycosides - properties and applications of a new class of surfactants. Angew Chem Int Ed. 14:1998;4699-4709.
18. von Rybinski W., Hill K. Alkyl polyglycosides. Holmberg K. Novel surfactants. 1998;31-85 Marcel Dekker, New York.
19. Söderman O., Johansson I. Polyhydroxyl-based surfactants and their physicochemical properties and applications. Curr Opin Colloid Interface Sci. 4:2000;391-401.
20. Nilsson F., Söderman O., Reimer J. Phase separation and aggregate-aggregate interactions in the C9G1/C10G1 β-alkylglucoside/water system. A phase diagram and NMR self-diffusion study. Langmuir. 14:1998;6396-6404. •The paper discusses the mechanism behind the liquid-liquid phase separation that occurs in the micellar region; this region is split into one concentrated and one dilute phase, both containing micelles.
21. Nilsson F., Söderman O., Johansson I. Four different C8G1 alkylglucosides. Anomeric effects and the influence of straight vs. branched hydrocarbon chains. J Colloid Interface Sci. 203:1998;131-139.
22. Dorfler H.D., Gopfert A. Lyotropic liquid crystals in binary systems n-alkylglucosides/water. J Dispersion Sci Technol. 20:1999;35-58.
23. Hantzschel D., Schulte J. Thermotropic and lyotropic properties of n-alkyl-β-D-glucopyranoside surfactants. PCCP. 1:1999;895-904.
24. Sierra M.L., Svensson M. Mixed micelles containing alkylglycosides: effect of the chain length and the polar head group. Langmuir. 15:1999;2301-2306. •Formation of micelles in mixtures of alkylglycosides and a conventional surfactant was studied. A strong negative value of the interaction parameter, β, indicating attractive interaction, was obtained for the mixture of alkylglycoside and the cationic surfactant. A somewhat smaller negative β-value was obtained for the mixture of a glycoside surfactant with the anionic surfactant. No interaction was seen for the alkylglycoside-alcohol ethoxylate mixture.
25. Holland P.M., Rubingh D.N. Mixed surfactant systems. ACS Symp Ser 501. 1992;American Chemical Society, Washington.
26. Liljeqvist P., Kronberg B. Comparing decyl β-maltoside and octa(ethylene glycol)mono n-decyl ether in mixed micelles with dodecylbenzene sulphonate-1. Formation of mixed micelles. J Colloid Interface Sci. 222:2000;159-164.
27. Liljeqvist P., Kronberg B. Comparing decyl β-maltoside and octa(ethylene glycol)mono n-decyl ether in mixed micelles with dodecylbenzene sulphonate-2. Interaction of mixed micelles with polyvinylpyrrolidone. J Colloid Interface Sci. 222:2000;165-169.
28. Laughlin R.G., Fu Y.-C., Wireko F.C., Scheibel J.J., Munyon R.L. The physical science of N-dodecanoyl-N-metylglucamine and its aqueous mixtures. Holmberg K. Novel surfactants. 1998;31-85 Marcel Dekker, New York.
29. Zhu Y.-P., Rosen M.J., Vinson P.K., Morral S.W. Surface properties of N-alkanoyl-N-metylglucamines and related materials. J Surf Det. 2:1999;357-362. •The effect of the number of hydroxyl groups in polyol surfactants on physico-chemical parameters such as CMC, area per molecule and Krafft point was investigated. The values of all three parameters were reduced with decreasing number of hydroxyl groups.
30. Allen D.K., Tao B.Y. Carbohydrate-alkyl ester derivatives as biosurfactants. J Surf Det. 2:1999;383-390.
31. Fregapane G., Sarney D.B., Vulfson E.N. Facile chemoenzymatic synthesis of monosaccharide fatty acid esters. Biocatalysis. 11:1994;9-18.
32. Sarney D.B., Kapeller H., Fregapane G., Vulfson E.N. Chemoenzymatic synthesis of disaccharide fatty acid esters. J Am Oil Chem Soc. 71:1994;711-714.
33. Baker I.J.A., Matthews B., Suares H., et al. Sugar fatty acid ester surfactants: structure and ultimate aerobic biodegradation. J Surf Det. 3:2000;1-12. •A series of sugar esters with different sized sugar headgroups were investigated with respect to ultimate aerobic biodegradation. Sugar esters with either a sulfonate or an ethyl group in α-position of the fatty acyl chain were also included. It was found that variations of the sugar headgroup did not much affect the rate of biodegradation. The α substituted surfactants degraded at a lower rate.
34. Baker I.J.A., Willing I., Furlong D.N., Grieser F., Drummond C.J. Sugar fatty acid ester surfactants: biodegradation pathways. J Surf Det. 3:2000;13-28. ••The paper discusses biodegradation pathways for sugar ester surfactants. It was shown that normal nonionic sugar esters degraded via initial ester bond hydrolysis. Sugar ester surfactants with either a sulfonate or an ethyl group in α-position of the fatty acyl chain degraded by another, slower mechanism, ω-oxidation of the acyl chain.
35. Baker I.J.A., Furlong D.N., Grieser F., Drummond C.J. Sugar fatty acid ester surfactants: base-catalyzed hydrolysis. J Surf Det. 3:2000;29-32.
36. Boyd B.J., Drummond C.J., Krodkiewska I., Grieser F. How chain length, headgroup polymerization, and anomeric configuration govern the thermotropic and lyotropic liquid crystalline phase behavior and the air-water interfacial adsorption of glucose-based surfactants. Langmuir. 16:2000;7359-7367. •The effect of alkyl chain length, headgroup polymerization and anomeric configuration of a series of sugar esters on physico-chemical properties were investigated.
37. Gao C., Millqvist-Fureby A., Whitcombe M.J., Vulfson E.N. Regioselective synthesis of dimeric (gemini) and trimeric sugar-based surfactants. J Surf Det. 2:1999;293-302. ••An impressive series of gemini sugar surfactants (and some trimeric surfactants) were synthesized by a combination of enzymatic and organo-chemical routes.
38. Vulfson E. Enzymatic synthesis of surfactants. Holmberg K. Novel surfactants. 1998;279-300 Marcel Dekker, New York.
39. Valivety R., Jauregi P. Chemo-enzymatic synthesis of amino acid-based surfactants. J Am Oil Chem Soc. 74:1997;879-886.
40. Infante M.R., Péres L., Pinazo A. Novel cationic surfactants from arginine. Holmberg K. Novel surfactants. 1998;87-114 Marcel Dekker, New York.
41. Pinazo A., Infante M.R., Izquierdo P., Solans C. Synthesis of arginine-based surfactants in highly concentrated water-in-oil emulsions. J Chem Soc Perkin Trans. 2:2000;1535-1539. ••A highly concentrated water-in-oil emulsion was used as a reaction medium for acylation of arginine methyl ester with dodecanoic acid. It was demonstrated that such emulsions should be seen as an alternative to apropic, polar solvents such as dimethylformamide and also to microemulsions.
42. Clapes P., Moran C., Infante M.R. Enzymatic synthesis of arginine-based cationic surfactants. Biotechnol Bioeng. 63:1999;333-343.
43. Piera E., Dominguez C., Clapes P., Erra P., Infante M.R. Qualitative and quantitative analysis of new alkyl amide arginine surfactants by high performance liquid chromatography and capillary electrophoresis. J Chromatogr A. 852:1999;499-506.
44. Piera E., Infante M.R., Clapes P. Chemo-enzymatic synthesis of arginine-based gemini surfactants. Biotechnol Bioeng. 70:2000;323-331.
45. Pinazo A., Wen X.Y., Perez L., Infante M.R., Franses E.I. Aggregation behavior in water of monomeric and gemini cationic surfactants derived from arginine. Langmuir. 15:2000;3134-3142.
46. Pegiaduo S., Perez L., Infante M.R. Synthesis, characterization and surface properties of 1-N-L-tryptofan-glycerol-ether surfactants. J Surf Det. 3:1999;517-525. •A new type of tryptophan-based surfactants were synthesized and characterized with respect to CMC, surface tension and area per molecule at the air-water interface. The tryptophane surfactants showed very low CMC values.
47. Vives M.A., Macian M., Seguer J., Infante M.R., Vinardell M.P. Hemolytic action of anionic surfactants of the diacyl lysine type. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 118:1997;71-74.
48. Vives M.A., Infante M.R., Garcia E., Selve C., Maugras M., Vinardell M.P. Erythrocyte hemolysis and shape changes induced by new lysine-derivate surfactants. Chem Biol Interact. 118:1999;1-18.
49. Folmer BM, Holmberg K, Gottberg Klingskog E, Bergström K. Fatty amide ethoxylates; synthesis and self-assembly. J Surf Det 2001 (in press). •A series of fatty acid monoethanolamide ethoxylates with varying number of double bonds in the acyl chain and with varying number of oxyethylene groups in the polar headgroup was investigated. The influence of the amide bond and of the unsaturations on adsorption at the air-water interface and on self-assembly was investigated.
50. Folmer BM, Nydén M, Holmberg K. Micellization and adsorption of a series of fatty amide ethoxylates. J Colloid Interface Sci 2001; in press. •A series of fatty acid monoethanolamide ethoxylates with varying number of double bonds in the acyl chain and with varying number of oxyethylene groups in the polar headgroup was investigated. The influence of the amide bond and of the unsaturations on adsorption at a hydrophobic solid surface and on micellization was investigated by ellipsometry and by NMR.
51. Svensson M. Surfactants based on sterols and other alicyclic compounds. Holmberg K. Novel surfactants. 1998;179-200 Marcel Dekker, New York.
52. Folmer BM. Sterol surfactants; from synthesis to applications. In: Karsa DR, editor. Annual surfactant reviews, Vol. 3. Sheffield, UK: Sheffield Academic Press, 2001 (in press).
53. Folmer B.M., Svensson M., Holmberg K., Brown W. The physicochemical behavior of phytosterol ethoxylates. J Colloid Interface Sci. 213:1999;112-120. •A series of sterol ethoxylates was investigated. It was found that the time to reach equilibrium surface tension was very long, more than two hours. This probably reflects both exchange reactions at the surface and a slow reorientation of molecules at the air-water interface.
54. Folmer BM, Nydén M. Structure and dynamics in the micellar and cubic phase of an ethoxylated phytosterol surfactant. Langmuir (submitted).
55. Folmer BM. Ph.D. Thesis. Royal Institute of Technology, Stockholm, Sweden, 2000.