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Licensed Unlicensed Requires Authentication Published by De Gruyter February 17, 2021

Preparation of a Gemini Surfactant from Mixed Fatty Acid and its Use in Cosmetics

Herstellung eines Geminitensids aus gemischter Fettsäure und seine Verwendung in Kosmetika
  • Kirti Datir

    Ms. Kirti Datir, completed M. Tech. (Oils, Oleochemicals and Surfactants Technology) from Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India. At present perusing Ph.D. (Tech.) from Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India., Research interest- Green surfactants, applications in pharma and biomedical

    , Harshada Shinde

    Ms. Harshada Shinde, perusing M.Sc. (Analytical Chemistry) from K. J. Somaiya College of Science and Commerce, Mumbai, Maharashtra, India. Research interest-Organic/enzymatic synthesis of surfactants, analytical method development etc.

    and Amit P. Pratap

    Professor (Dr.) Amit P. Pratap, completed graduation and post graduation in Technology of Oils, Oleochemicals and Surfactants and obtained Ph.D. (Tech.) from ICT. At present working as Professor and Head of the Department of Oils, Oleochemicals and Surfactants Technology at Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India. Research interest-Organic/enzymatic synthesis of surfactants, Microbial biosurfactants, specialty products and applications, Biolubricants etc.

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Abstract

Among the surfactants, dimeric surfactants represent a niche group with multifunctional properties. In this work a modified gemini surfactant was synthesized using symmetrical fatty acids. Due to the spacers used to combine the two symmetrical monomers, the synthesized gemini surfactant is cationic. The structure of the compound was confirmed with 1H-NMR. The most advantageous property of the gemini surfactant is that it has a lower surface tension, i. e. less than 35 mNm–1 at 25°C, compared to monomeric surfactants. The surface tension was determined with a Kyowa tensiometer. The CMC (critical micelle formation concentration) was calculated according to the pyrene method and detected by UV spectroscopy at 25°C. The very low CMC is another market advantage of the gemini surfactant. Hydrophobicity and hydrophilicity of the synthesized compound were checked by the emulsification method. The ability of the synthesized gemini surfactant to wet and foam and the emulsification index at different pH values were tested. Based on the results, the gemini surfactant was used in formulations for hair and skin care. Conditioners and creams were prepared with the synthesized compound and the properties were analyzed at different concentrations of the gemini surfactant in the respective formulation.

Abstract

Unter den Tensiden stellen dimere Tenside eine Nischengruppe mit multifunktionellen Eigenschaften dar. In dieser Arbeit wurde ein modifiziertes Geminitensid unter Verwendung symmetrischer Fettsäuren synthetisiert. Aufgrund der Spacer, die für die Verbindung der zwei symmetrischen Monomeren verwendet wurden, ist das synthetisierte Geminitensid kationisch. Die Struktur der Verbindung wurde mit 1H-NMR bestätigt. Die vorteilhafteste Eigenschaft des Geminitensids ist, dass es im Vergleich zu monomeren Tensiden eine niedrigere Oberflächenspannung, d. h. kleiner als 35 mNm–1 bei 25°C, aufweist. Die Oberflächenspannung wurde mit einem Kyowa-Tensiometer bestimmt. Die CMC (kritische mizellare Mizellenbildungskonzentration) wurde nach der Pyren-Methode berechnet und UV-spektroskopisch bei 25°C nachgewiesen. Die sehr geringe CMC ist ein weiterer Marktvorteil des Geminitensids. Hydrophobie und Hydrophile der synthetisierten Verbindung wurden mit der Emulgierungsmethode überprüft. Die Fähigkeit des synthetisierten Geminitensids zur Benetzung und zur Schaumbildung sowie der Emulgierungs-index bei verschiedenen pH-Werten wurden getestet. Aufgrund der Ergebnisse wurde das Geminitensid in Formulierungen für die Haar- und Hautpflege eingesetzt. Conditioner und Cremes wurden mit der synthetisierten Verbindung wurden hergestellt, und die Eigenschaften wurden bei verschiedenen Konzentrationen des Geminitensids in der jeweiligen Formulierung analysiert.


Professor Dr. Amit P. Pratap Department of Oils, Oleochemicals and Surfactants Technology Institute of Chemical Technology, (University under Section 3 of UGC Act 1956 Maharashtra Government’s "Elite Status and Center of Excellence" Formerly UDCT/UICT, University of Mumbai) Nathalal Parekh Road Matunga (East), Mumbai-400 019 India Tel.: 91-22-3361 2556 Fax: 91-22-3361 1020 Cell: 91-92210 48682, 99300 40853 E-Mail: ap.pratap@ictmumbai.edu.in

About the authors

Kirti Datir

Ms. Kirti Datir, completed M. Tech. (Oils, Oleochemicals and Surfactants Technology) from Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India. At present perusing Ph.D. (Tech.) from Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India., Research interest- Green surfactants, applications in pharma and biomedical

Harshada Shinde

Ms. Harshada Shinde, perusing M.Sc. (Analytical Chemistry) from K. J. Somaiya College of Science and Commerce, Mumbai, Maharashtra, India. Research interest-Organic/enzymatic synthesis of surfactants, analytical method development etc.

Professor Dr. Amit P. Pratap

Professor (Dr.) Amit P. Pratap, completed graduation and post graduation in Technology of Oils, Oleochemicals and Surfactants and obtained Ph.D. (Tech.) from ICT. At present working as Professor and Head of the Department of Oils, Oleochemicals and Surfactants Technology at Institute of Chemical Technology, Matunga (East), Mumbai – 400 019, Maharashtra, India. Research interest-Organic/enzymatic synthesis of surfactants, Microbial biosurfactants, specialty products and applications, Biolubricants etc.

References

1 Rosen, J. M. and Tracy, J. D.: Gemini Surfactant JSD. 1 (1998) 547–554. DOI:10.1007/s11743-998-0057-810.1007/s11743-998-0057-8Search in Google Scholar

2 Weinberger, R.: Capillary Zone Electrophoresis – Secondary Equilibrium, Micelles, Cyclodextrins, and Related Reagents. Pract Capill Electrophor. (2000) 139–208. DOI:10.1016/B978-012742356-2/50006-710.1016/B978-012742356-2/50006-7Search in Google Scholar

3 Danino, D., Talmon, Y. and Zana, R.: Vesicle-to-micelle transformation in systems containing dimeric surfactants. J Colloid Interface Sci. 185 (1997) 84–93. PMid:9056307; DOI:10.1006/jcis.1996.454510.1006/jcis.1996.4545Search in Google Scholar PubMed

4 https://www.cosmeticsandtoiletries.com/formulating/function/surfactant/30582274.htmlSearch in Google Scholar

5 Rhein, L. D.: editor. Surfactants in Personal Care Products and Decorative Cosmetics. 3rded. Boca Raton: CRC Press; (2007) 480 p. (Surfactant science series).10.1201/9781420016123Search in Google Scholar

6 Lakra, J., Tikariha, D., Yadav, T., Das, S., Ghosh, S., Satnami, M. L. and Ghosh, K. K.: Mixed micellization of gemini and cationic surfactants: Physicochemical properties and solubilization of polycyclic aromatic hydrocarbons. Colloids Surfaces A Physicochem Eng Asp 451 (2014) 56–65. 10.1016/j.colsurfa.2014.03.037Search in Google Scholar

7 Castro, M. J. L., Ojeda, C. and Cirelli, A. F. : Advances in surfactants for agrochemicals. Environ Chem Lett 12 (2014) 85–95. DOI:10.1007/s10311-013-0432-410.1007/s10311-013-0432-4Search in Google Scholar

8 Athas, J. C., Jun., K., McCafferty, C., Owoseni, O., John, V. T. and Raghavan, S. R.: An effective dispersant for oil spills based on food-grade amphiphiles. Langmuir 30 (2014) 9285–9294. PMid:25072867; DOI:10.1021/la502312n10.1021/la502312nSearch in Google Scholar PubMed

9 Song, D.: Development of High Efficient and Low Toxic Oil Spill Dispersants based on Sorbitol Derivants Nonionic Surfactants and Glycolipid Biosurfactants. J Environ Prot (Irvine, Calif) 04 (2013) 16–22. DOI:10.4236/jep.2013.41b00410.4236/jep.2013.41b004Search in Google Scholar

10 Schramm, L. L., Stasiuk, E. N. and Marangoni, D. G.: Surfactants and their applications. Annu Reports Prog Chem – Sect C 99 (2003) 3–48. DOI:10.1039/B208499F10.1039/B208499FSearch in Google Scholar

11 Lukáč, M., Lacko, I., Bukovskyý, M., Kyselová, Z., Karlovská, J., Horváth, B. and Devínsky, F.: Synthesis and antimicrobial activity of a series of optically active quaternary ammonium salts derived from phenylalanine. Cent Eur J Chem 8 (2010) 194–201. DOI:10.2478/s11532-009-0126-810.2478/s11532-009-0126-8Search in Google Scholar

12 Damen, M., Cristóbal-Lecina, E., Sanmartí, G. C., VanDongen, S. F. M., García, Rodríguez, C, L., Dolbnya, I, P., Nolte, R. J. M. and Feiters, M. C.: Structure-delivery relationships of lysine-based gemini surfactants and their lipoplexes. Soft Matter 10 (2014) 5702–5714. PMid:24969740; DOI:10.1039/c4sm00881b10.1039/c4sm00881bSearch in Google Scholar PubMed

13 Menger, F. M., Keiper, J. S. and Azov, V.: Gemini surfactants with acetylenic spacers. Langmuir 16 (2000) 2062–2067. DOI:10.1021/la991057610.1021/la9910576Search in Google Scholar

14 Wattebled, L., Note, C. and Laschewsky, A.: Structure-Property relationships of \Gemini" surfactants and synergism with Hydrotropes. Tenside Surfactants Deterg (2007) 25–33. DOI:10.3139/113.10032510.3139/113.100325Search in Google Scholar

15 Xie, Y., Liu, J., Liu, F. and Xu, H.: Synthesis and properties of a novel gemini surfactants with Bis-piperidinium. Tenside SurfactantsDeterg 54 (5) (2017) 437–442. DOI:10.3139/113.11052110.3139/113.110521Search in Google Scholar

16 Niu, R., Wang, C., Song, H., Wang, J., Wang, D. and Ren, W.: Synthesis and Surface/Interfacial properties of novel dialkyl disulfonate gemini surfactants derived from 1,3,5-triazine. Tenside SurfactantsDeterg 53(6) (2016) 595–600. DOI:10.3139/113.11046610.3139/113.110466Search in Google Scholar

17 Han, P., He, Y., Chen, C., Yu, H., Liu, F., Yang, H., Ma, Y. and Zheng, Y.: Study on synergistic mechanism of inhibitor mixture based on electron transfer behavior. Sci Rep 6 (2016) 1–10. PMid:27671332; DOI:10.1038/srep3325210.1038/srep33252Search in Google Scholar PubMed PubMed Central

18 Li, H., Yu, C., Chen, R., Li, J. and Li, J.: Novel ionic liquid-type Gemini surfactants: Synthesis, surface property and antimicrobial activity. Colloids Surfaces A Physicochem Eng Asp 395 (2012) 116–124. 10.1016/j.colsurfa.2011.12.014Search in Google Scholar

19 Xu, Q., Wang, L. and Xing, F.: Synthesis and properties of dissymmetric gemini surfactants. J Surfactants Deterg 14 (2011) 85–90. PMid:21841907; DOI:10.1007/s11743-010-1207-610.1007/s11743-010-1207-6Search in Google Scholar PubMed PubMed Central

20 Sharma, T., Dohare, N., Kumari, M., Singh, U. K., Khan, A. B., Borse, M. S. and Patel, R.: RSC Advances and its monomeric counterpart on the. RSC Adv 7 (2017) 16763–16776. DOI:10.1039/C7RA00172J10.1039/C7RA00172JSearch in Google Scholar

21 Ahtikari, J., Bansal, A., Jackson, P. H. and Solanki, Y.: Emulsification with nature based ingredients for personal care. Househ Pers Care Today 9 (2014) 22–25.Search in Google Scholar

22 García, M. T., Campos, E., Sánchez-Leal, J. and Comelles, F.: Structure-activity relationships for sorption of alkyl trimethyl ammonium compounds on activated sludge. Tenside, Surfactants, Deterg 41 (2004) 235–239. DOI:10.3139/113.10022910.3139/113.100229Search in Google Scholar

23 Brycki, B, E., Kowalczyk, I. H., Szulc, A., Kaczerewska, O. and Pakiet, M.: Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications. Appl Charact Surfactants. (2017). DOI:10.5772/intechopen.6875510.5772/intechopen.68755Search in Google Scholar

24 Bhadani, A., Tani, M., Endo, T., Sakai, K., Abe, M. and Sakai, H.: New ester based gemini surfactants: the effect of different cationic headgroups on micellization properties and viscosity of aqueous micellar solution. Phys Chem Chem Phys 17 (2015) 19474–19483. PMid:26145125; DOI:10.1039/c5cp02115d10.1039/c5cp02115dSearch in Google Scholar PubMed

25 Tanhaei, B., Saghatoleslami, N., Chenar, M. P., Ayati, A., Hesampour, M. and Mänttäri, M.: Experimental study of CMC evaluation in single and mixed surfactant systems, using the UV-Vis spectroscopic method. J Surfactants Deterg 16 (2013) 357–362. DOI:10.1007/s11743-012-1403-710.1007/s11743-012-1403-7Search in Google Scholar

26 Fu, J., Cai, Z., Gong, Y., O’Reilly, S. E., Hao, X. and Zhao, D.: A new technique for determining critical micelle concentrations of surfactants and oil dispersants via UV absorbance of pyrene. Colloids Surfaces A Physicochem Eng Asp 484 (2015) 1–8. 10.1016/j.colsurfa.2015.07.039Search in Google Scholar

27 Tofani, L., Feis, A., Snoke, R. E., Berti, D., Baglioni, P. and Smulevich, G.: Spectroscopic and interfacial properties of myoglobin/surfactant complexes. Biophys J 87 (2004) 1186–1195. PMid:15298921; DOI:10.1529/biophysj.104.04173110.1529/biophysj.104.041731Search in Google Scholar PubMed PubMed Central

28 Laschewsky, A., Wattebled, L., Arotçaréna, M., Habib-Jiwan, J. L. and Rakotoaly, R.: H. Synthesis and properties of cationic oligomeric surfactants. Langmuir 21 (2005) 7170–7179. PMid:16042438; DOI:10.1021/la050952o10.1021/la050952oSearch in Google Scholar PubMed

29 Liu, J., Chen, Y., Xu, R. and Jia, Y.: Screening and Evaluation of Biosurfactant-Producing Strains Isolated from Oilfield Wastewater. Indian J Microbiol 53 (2013) 168–174. PMid:24426104; DOI:10.1007/s12088-013-0379-y10.1007/s12088-013-0379-ySearch in Google Scholar PubMed PubMed Central

30 Chime, S. A., Kenechukwu, F. C. and Attama, A. A.: Nanoemulsions – Advances in Formulation, Characterization and Applications in Drug Delivery. Appl Nanotechnol Drug Deliv.(2014). DOI:10.5772/5867310.5772/58673Search in Google Scholar

31 Paez. A., Howe, A. and Goldschmidt, D.: Corporation C Cationic emulsifiers?: an emerging trend in skin care.(1999) 67–71.Search in Google Scholar

32 Puchta, R.: Cationic surfactants in laundry detergents and laundry after treatment aids. 61 (1984) 367–368. DOI:10.1007/BF0267879610.1007/BF02678796Search in Google Scholar

Received: 2020-05-08
Accepted: 2020-10-04
Published Online: 2021-02-17
Published in Print: 2021-01-27

© 2021 Walter de Gruyter GmbH, Berlin/Boston, Germany

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