Abstract
Sodium N-dodecanoyl sarcosinate (SDDS), a novel amino-acid based surfactant, has immense biological and industrial importance. Although it is being used in a number of cosmetic formulations, systematic analysis of the bulk and interfacial properties of the surfactant is scarce in the literature. In this study, effects of salt, temperature, and pH on the self-association and related properties of SDDS have been examined in detail using methods such as tensiometry, conductometry, fluorimetry, pH-metry, spectrophotometry, calorimetry, and circular dichroism. The nature of amphiphilic packing and the aggregation numbers of the assemblies have been deciphered. Properties of the acid form of the surfactant have also been explored. The results have been conceptually rationalized and systematically presented together with associated energetics of the interfacial adsorption and self-aggregation of the surfactant in the bulk.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs11743-008-1105-3/MediaObjects/11743_2008_1105_Fig1_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs11743-008-1105-3/MediaObjects/11743_2008_1105_Fig2_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs11743-008-1105-3/MediaObjects/11743_2008_1105_Fig3_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs11743-008-1105-3/MediaObjects/11743_2008_1105_Fig4_HTML.gif)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1007%2Fs11743-008-1105-3/MediaObjects/11743_2008_1105_Fig5_HTML.gif)
Similar content being viewed by others
Abbreviations
- HDDS:
-
Dodecanoyl sarcosinic acid
- MDGA:
-
N-methyl-N-decanoyl glucamide
- SDS:
-
Sodium dodecyl sulfate
- SDDS:
-
Sodium N-dodecanoyl sarcosinate
References
Miyagishi S, Ishibai Y, Asakawa T, Nishida M (1985) Critical micelle concentration in mixtures of N-acyl amino acid surfactants. J Colloid Interface Sci 103:164–169
Valivety T, Jauregi P, Gill IS, Vulfson EN (1997) Chemo-enzymatic synthesis of amino acid-based surfactants. J Am Oil Chem Soc 74:879–886
Valivety R, Gill IS, Vulfson EN (1998) Application of enzymes to the synthesis of amino acid-based bola and gemini surfactants. J Surf Deterg 1:177–185
Moran MC, Pinazo A, Perez L, Clapes P, Angelet M, Garcia MT, Vinardell MP, Infante MR (2004) “Green” amino acid-based surfactants. Green Chem 6:233–240
George A, Modi J, Jain N, Bahadur P (1998) A Comparative study on the surface activity and micellar behavior of some N-acylamino acid based surfactants. Indian J Chem 37:985–992
Varade D, Bahadur P (2005) Interaction in mixed micellization of sodium N-tetradecanoylsarcosinate with ionic and nonionic surfactants. J Dispers Sci Technol 26:549–554
Spivack JD (1976) In: Linfield WM (ed) Anionic surfactants. Marcel Dekker, New York
Lanigan RS (2001) Final report on the safety assessment of cocoyl sarcosine, lauroyl sarcosine, myristoyl sarcosine, oleoyl sarcosine, stearoyl sarcosine, sodium cocoyl sarcosinate, sodium lauroyl sarcosinate, sodium myristoyl sarcosinate, ammonium cocoyl sarcosinate and ammonium lauroyl sarcosinate. Int J Toxicol 20(Suppl. 1):1–14 Published by Informa Healthcare
Castillo EJ, Han WW, Gerson SH (2000) Use of certain anionic amino acid based surfactants to enhance antimicrobial effectiveness of topically administrable pharmaceutical compositions. United States Patent 6,146,622
Orr TV, Sabatelli AD (1992) Skin conditioning composition and method. European Patent EP0283165
Schmidt et al (1986) European Patent Application No.0194097EP assigned to Procter and Gamble mentions sodium lauroyl sarcosinate as the mild anionic surfactant utilized in an aerosol skin-cleansing and moisturizer mousse
Ecochem, Ingredients of eco-solutions
Tsubone K, Rosen MJ (2001) Structural effect on surface activities of anionic surfactants having N-acyl-N-methylamide and carboxylate groups. J Colloid Interface Sci 244:394–398
Fuguet E, Rafóls C, Róses M, Bosch E (2005) Critical micelle concentration of surfactants in aqueous buffered and unbuffered systems. Anal Chim Acta 548:95–100
Sehgal P, Doe H, Bakshi M (2004) Interfacial and micellar properties of binary mixtures of surfactant and phospholipid in an aqueous medium. Colloid Polym Sci 281:275–282
Dan A, Chakraborty I, Ghosh S, Moulik SP (2007) Interfacial and bulk behavior of sodium dodecylsulfate in isopropanol–water and in isopropanol–poly (Vinylpyrrolidone)–water media. Langmuir 23:7531–7538
Chatterjee A, Moulik SP, Sanyal SK, Mishra BK, Puri PM (2001) Thermodynamics of micelle formation of ionic surfactants: a critical assessment for sodium dodecyl sulfate, cetyl pyridinium chloride and dioctyl sulfosuccinate (Na salt) by microcalorimetric, conductometric and tensiometric measurements. J Phys Chem B 105:12823–12831
Chatterjee A, Maiti S, Sanyal SK, Moulik SP (2002) Micellization and related behaviors of N-cetyl-N-ethanolyl-N, N-dimethyl and N-cetyl-N, N-diethanolyl-N-methyl ammonium bromide. Langmuir 18:2998–3004
Prasad M, Chakraborty I, Rakshit AK, Moulik SP (2006) A critical evaluation of micellization behavior of a nonionic surfactant MEGA 10 in comparison with an ionic surfactant tetradecyltriphenylphosphonium bromide studied by microcalorimetric method in aqueous medium. J Phys Chem B 110:9815–9821
Da Graca Miguel M, Eidelman O, Ollivon M, Walter A (1989) Temperature dependence of the vesicle-micelle transition of egg phosphatidylcholine and octyl glucoside. Biochemistry 28:8921–8928
Keller M, Kerth A, Blume A (1997) Thermodynamics of interaction of octyl glucoside with phosphatidylcholine vesicles: partitioning and solubilization as studied by high sensitivity titration calorimetry. Biochim Biophys Acta 1326:178–192
Chatterjee A, Dey T, Sanyal SK, Moulik SP (2001) Thermodynamic of micelle formation and surface chemical behavior of p-tert-octylphenoxypolyoxyethylene ether (TritonX-100) in aqueous medium. J Surf Sci Tech 17:1–16
Becher P (1967) In: Schick MJ (ed) Nonionic surfactants. Marcel Dekker, New York ch. 15
La Messa C (1990) Dependence of critical micelle concentrations on intensive variables: a reduced variable analysis. J Phys Chem 94:323–326
Abu-Hamdiyyah M, Al-Mansour L (1979) Effect of butylurea on the critical micelle concentration of sodium lauryl sulfate in water at different temperatures. J Phys Chem 83:2236–2243
Benrraou M, Bales BL, Zana R (2003) Effect of the nature of the counterion on the properties of anionic surfactants.1. Cmc, ionization degree at the CMC and aggregation number of micelles of sodium, cesium, tetramethylammonium, tetraethylammonium, tetrapropylammonium, and tetrabutylammonium dodecyl sulfates. J Phys Chem B 107:13432–13440
Ribiero ACF, Lobo VMM, Valente AJM, Azevedo EFG, da Graca Miguel M, Burrows HD (2004) Transport properties of alkyltrimethylammonium bromide surfactants in aqueous solutions. Colloid Polym Sci 283:277–283
Delisi R, Inglese A, Milioto S, Pellerito A (1997) Demixing of mixed micelles. Thermodynamics of perfluorooctanoate-sodium dodecanoate mixtures in water. Langmuir 13:192–202
Basu Ray G, Chakraborty I, Ghosh S, Moulik SP, Palepu R (2005) Self-aggregation of alkyltrimethylammonium bromides (C10–, C12–, C14–, and C16TAB) and their binary mixtures in aqueous medium: a critical and comprehensive assessment of interfacial behavior and bulk properties with reference to two types of micelle formation. Langmuir 21:10958–10967
Basu Ray G, Chakraborty I, Ghosh S, Moulik SP (2007) A critical and comprehensive assessment of interfacial and bulk properties of aqueous binary mixtures of anionic surfactants, sodium dodecylsulfate, and sodium dodecylbenzenesulfonate. Colloid Polym Sci 285:457–469
Basu Ray G, Chakraborty I, Ghosh S, Moulik SP (2007) On mixed binary surfactant systems comprising MEGA 10 and alkyltrimethylammonium bromides: a detailed physicochemical study with a critical analysis. J Colloid Interface Sci 307:543–553
Buckingham SA, Garvey CJ, Warr GG (1993) Effect of head-group size on micellization and phase behavior in quaternary ammonium surfactant systems. J Phys Chem 97:10236–10244
Kale KM, Cussler EL, Evans DF (1980) Characterization of micellar solutions using surfactant ion electrodes. J Phys Chem 84:593–598
Bandyopadhyay A, Moulik SP (1988) Counterion binding behavior of micelles of sodium dodecyl sulphate and bile salts in the pure state, in mutually mixed states and mixed with a nonionic surfactant. Colloid Polym Sci 266:455–461
Chakraborty I, Moulik SP (2007) Self-aggregation of ionic C10 surfactants having different headgroups with special reference to the behavior of decyltrimethylammonium bromide in different salt environments: a calorimetric study with energetic analysis. J Phys Chem B 111:3658–3664
Moroi Y (1992) Micelle: theoretical and applied aspects. Plenum, New York
Kresheck GC (1998) Comparison of the calorimetric and van’t Hoff enthalpy of micelle formation for a nonionic surfactant in H2O and D2O Solutions from 15 to 40 °C. J Phys Chem 102:6596–6600
Kresheck GC, Hargraves WA (1974) Thermometric titration studied of the effect of head group, chain length, solvent, and temperature on the thermodynamics of micelle formation. J Colloid Interface Sci 48:481–493
Israelachvili JN (1991) Intermolecular and surface forces, chapter 17, 2nd edn. Academic Press, London, p 370
Tanford C (1980) The hydrophobic effect: formation of micelles and biological membranes. Wiley, New York
Hart JR (1979) N-acyl sarcosine surfactants. Cosmet Toiletries 94:74–76
Zhang Y, Cremer PS (2006) Interaction between macromolecules and ions: the Hoffmeister series. Curr Opin Chem Biol 10:658–663
**aodong M, Pawlik M (2006) Adsorption of guar gums onto quartz from dilute mixed electrolyte solutions. J Colloid Interface Sci 298:609–614
Corrin ML, Harkins WD (1947) The effect of salts on the critical concentration for the formation of micelles in colloidal electrolytes. J Am Chem Soc 69:683–688
Fujio K (1998) The salt-induced sphere-rod transition of micelles of 1-tetradecylpyridinium bromide in aqueous NaBr solutions. Bull Chem Soc Jpn 71:83–89
Fujio K, Ikeda S (1991) Size of spherical micelles of dodecylpyridinium bromide in aqueous NaBr solutions. Langmuir 7:2899–2903
Haldar J, Aswal VK, Goyal PS, Bhattacharya S (2005) Micellar association in simultaneous presence of organic salts/additives. J Colloid Interface Sci 282:156–161
Kim W-J, Yang S-M (2000) Unusual micellar properties of multiheaded cationic surfactants in the presence of strong charge neutralizing salts. J Colloid Interface Sci 232:225–234
Kumar S, Khan ZA, Kabir-ud-din (2002) Effects of sodium salicylate on the microstructure of an aqueous micellar solution and its rheological response. J Surf Deterg 5:55–59
Leontidis E (2002) Hoffmeister anion effects on surfactant self-assembly and the formation of mesoporous solids. Curr Opin Colloid Interface Sci 7:81–91
Bostrom M, Williams DR, Ninham BW (2004) Why the properties of proteins in salt solutions follow a Hoffmeister series. Curr Opin Colloid Interface Sci 9:48–52
Rakshit PC (1988) In: Rakshit SC (ed) Physical chemistry. Sarat Book House, Kolkata, India
Aswal VK, Goyal PS (2000) Counterions in the growth of ionic micelles in aqueous electrolyte solutions: a small-angle neutron scattering study. Phys Rev E 61:2947–2953
Okawauchi M, Hagio M, Ikawa Y, Sugihara G, Murata Y, Tanaka M (1987) A light-scattering study of temperature effect on micelle formation of N-alkanoyl-N-methylglucamines in aqueous solution. Bull Chem Soc Jpn 60:2719–2725
Prasad M, Moulik SP, Mc Donald A, Palepu R (2004) Self-aggregation of alkyl (C10–, C12–, C14–, C16–) triphenyl phosphonium bromides and their 1:1 molar mixtures in aqueous medium: a thermodynamic study. J Phys Chem B 108:355–362
Basu Ray G, Chakraborty I, Ghosh S, Moulik SP, Holgate C, Glenn K, Palepu RM (2007) Studies on binary and ternary amphiphile combinations of tetradecyl trimethylammonium bromide (C14TAB), tetradecyltriphenylphosphonium bromide (C14TPB), and tetradecylpyridinium bromide (C14PB). A critical analysis of their interfacial and bulk behaviors. J Phys Chem B 111:9828–9837
Akisada H, Kuwahara J, Kunisaki M, Nishikawa K, Akagi S, Wada M, Kuwata A, Iwamoto S (2004) A circular dichroism study of the interaction between n-decanoyl-N-methylglucamide and surface active agents in mixed micelles. Colloid Polym Sci 283:169–173
Acknowledgments
G. Basu Ray thanks the CSIR, Govt. of India, for a Research Fellowship and SPM thanks the INSA for a Honorary Scientist position to perform this work. SG thanks DST (SR/FTP/CS-35/2006) for support with a first track project. The authors also thank Ms. D. Mitra and Mr. A. Dan for calorimetric and fluorometric measurements.
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Ray, G.B., Ghosh, S. & Moulik, S.P. Physicochemical Studies on the Interfacial and Bulk Behaviors of Sodium N-Dodecanoyl Sarcosinate (SDDS). J Surfact Deterg 12, 131–143 (2009). https://doi.org/10.1007/s11743-008-1105-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11743-008-1105-3