Home Physical Sciences Synthesis and Properties of Alkyl Bis-Guanidinium Acetates Surfactants
Article
Licensed
Unlicensed Requires Authentication

Synthesis and Properties of Alkyl Bis-Guanidinium Acetates Surfactants

  • Yongbo Song, Senior engineer, Taiyuan Institute of Technology, China. He received Ph.D. from Shanxi University, China. His research interests are focused on the synthesis, physicochemical property and theoretical research of cationic surfactants.

    EMAIL logo
    ,

    Hongyan Zheng, Senior engineer of Taiyuan Institute of Technology. Her research field is focused on the application investigation of surfactants.

    ,

    Yulan Niu, Dean of department of chemistry and chemical engineering, Taiyuan Institute of Technology, China. His research interests are focused on the engineering development related to manufactures of fine chemical.

    ,

    Ying Yao, Lecturer, Taiyuan Institute of Technology, China. Her research field is focused on the theoretical investigation of surfactants.

    and

    Rongqian Meng, Lecturer, Taiyuan Institute of Technology, China. Her research field is focused on the analysis and detection of surfactants.

Published/Copyright: March 13, 2021
Become an author with De Gruyter Brill

Abstract

Novel surfactants with double hydrophilic groups (cocopropane and tallowpropane bis-guanidinium acetates), were synthesized and tested to evaluate both the basic surfactant properties and the unique application performance. Surface tension, conductivity and contact angle measurements were used to study the self-aggregation behavior in aqueous solution. Aggregation parameters were calculated such as adsorption efficiency and effectiveness (pC20 and CAC/C20), the maximum surface excess concentration (Гmax) and minimum surface area permolecule (Amin). The thermodynamic parameters of aggregation based conductivity measurements revealed that the aggregation process was spontaneous and entropy-driven. Compared to DTAC and CTAC, the alkyl bis-guanidinium acetates showed a higher emulsification capacity with both liquid kerosene and soybean oil. The evaluation of antimicrobial activity showed that the alkyl bisguanidinium acetates exhibited strong antibacterial activity against the tested strains at a concentration of 50 ppm.

Abstract

Synthese und Eigenschaften von Alkylbiguanidinacetat-Tensiden. Es wurden neuartige Tenside mit doppelten hydrophilen Gruppen (Kokospropan- und Rindertalgpropan-Biguanidinacetat) synthetisiert und getestet, um sowohl die grundlegenden oberflächenaktiven Eigenschaften als auch die einzigartige Anwendungsleistung zu bewerten. Oberflächenspannung, Leitfähigkeit und Kontaktwinkelmessungen wurden zur Untersuchung des Selbstaggregationsverhaltens in wässriger Lösung verwendet. Es wurden Aggregationsparameter wie die Adsorptionseffizienz und -effektivität (pC20 und CAC/C20), die maximale Oberflächen-Überschusskonzentration (Гmax) und der minimale Oberflächenbedarf pro Tensidmolekül (Amin) berechnet. Die thermodynamischen Parameter der Aggregation, die aus den Leitfähigkeitsmessungen berechnet wurden, zeigten, dass der Aggregationsprozess spontan und entropiegetrieben war. Im Vergleich zu DTAC und CTAC wiesen die Alkylbiguanidinacetate ein stärkeres Emulgiervermögen sowohl mit Flüssigparaffin als auch mit Sojaöl auf. Die Bewertung der antimikrobiellen Aktivität ergab, dass die Alkylbiguanidinacetate bei einer Konzentration von 50 ppm eine starke antibakterielle Aktivität gegen die getesteten Stämme aufwiesen.


Tel.: 086-351-3569476

About the authors

Dr. Yongbo Song

Yongbo Song, Senior engineer, Taiyuan Institute of Technology, China. He received Ph.D. from Shanxi University, China. His research interests are focused on the synthesis, physicochemical property and theoretical research of cationic surfactants.

Hongyan Zheng

Hongyan Zheng, Senior engineer of Taiyuan Institute of Technology. Her research field is focused on the application investigation of surfactants.

Yulan Niu

Yulan Niu, Dean of department of chemistry and chemical engineering, Taiyuan Institute of Technology, China. His research interests are focused on the engineering development related to manufactures of fine chemical.

Ying Yao

Ying Yao, Lecturer, Taiyuan Institute of Technology, China. Her research field is focused on the theoretical investigation of surfactants.

Rongqian Meng

Rongqian Meng, Lecturer, Taiyuan Institute of Technology, China. Her research field is focused on the analysis and detection of surfactants.

Acknowledgements

The authors acknowledge the financial supports by Science and Technology Innovation Project of Higher Education Institutions in Shanxi (No. 2019L0930).

References

1 Jiang, Y., Geng, T. and Li, Q.: Synthesis of Quaternary Ammonium Salts with Novel Counterions, J. Surf. Det. 15 (2012) 67–71. DOI:10.1007/s11743-011-1289-910.1007/s11743-011-1289-9Search in Google Scholar

2 Quagliotto, P., Barbero, N., Barolo, C., Artuso, E., Compari, C., Fisicaro, E. and Viscardi, G.: Synthesis and Properties of Cationic Surfactants with Tuned Hydrophylicity, J. Colloid Interface Sci. 340 (2009) 269–275. PMid:19815228; DOI:10.1016/j.jcis.2009.09.00910.1016/j.jcis.2009.09.009Search in Google Scholar PubMed

3 Li, Y., Li, Q., Zhi, L. and Zhang, M.: Synthesis, Characterization and Surface-Activity of Hydroxyethyl Group-Containing Quaternary Ammonium Surfactants, J. Surf. Det. 14 (2011) 529–533. DOI:10.1007/s11743-011-1279-y10.1007/s11743-011-1279-ySearch in Google Scholar

4 Ismail A. A., Abdelfatah M. B., Mohammed M. E., Abdallah A. E. and Ahmed I. A.: Synthesis and Biocidal Activity of Some Naphthalene-Based Cationic Surfactants, J. Colloid Interface Sci. 15 (2012) 223–234. PMid:22389580; DOI:10.1007/s11743-011-1286-z10.1007/s11743-011-1286-zSearch in Google Scholar PubMed PubMed Central

5 Chauhan,V., Singh, S. and Bhadani A.: Synthesis, Characterization and Surface Properties of Long Chain b-Hydroxy-c-Alkyloxy-N-Methylimidazolium Surfactants, Colloids Surf. A. 395 (2012) 1–9. 10.1016/j.colsurfa.2011.11.022Search in Google Scholar

6 Cornellas, A., Perez, L., Comelles, F., Ribosa, I., Manresa, A. and Garcia, M. T.: Self-Aggregation and Antimicrobial Activity of Imidazolium and Pyridinium Based Ionic Liquids in Aqueous Solution, J. Colloid Interface Sci. 355 (2011) 164–171. PMid:21186035; DOI:10.1016/j.jcis.2010.11.06310.1016/j.jcis.2010.11.063Search in Google Scholar PubMed

7 Inoue, T., Ebina, H., Dong, B. and Zheng, L.: Electrical Conductivity Study on Aggregate Formation of Long-Chain Imidazolium Ionic Liquids in Aqueous Solution, J. Colloid Interface Sci. 314 (2007) 236–241. PMid:17574264; DOI:10.1016/j.jcis.2007.05.05210.1016/j.jcis.2007.05.052Search in Google Scholar PubMed

8 Vanyúr, R., Biczók, L. and Miskolczy, Z.: Micelle Formation of 1-Alkyl-3-Methylimidazolium Bromide Ionic Liquids in Aqueous Solution, Colloids Surf. A. 299 (2007) 256–261. 10.1016/j.colsurfa.2006.11.049Search in Google Scholar

9 Miyake, M. and Oyama, N.: Effect of Amidoalkyl Group as Spacer on Aggregation Properties of Guanidine-Type Surfactants, J. Colloid Interface Sci. 330 (2009) 180–185. PMid:18990404; DOI:10.1016/j.jcis.2008.10.04710.1016/j.jcis.2008.10.047Search in Google Scholar PubMed

10 Miyake, M., Yamada, K. and Oyama, N.: Self-Assembling of Guanidine-Type Surfactant, Langmuir. 24 (2008) 8527–8532. PMid:18627192; DOI:10.1021/la801115y10.1021/la801115ySearch in Google Scholar PubMed

11 Fukui, H., Hatano, K., Kamio, K., Miyake, M., Tamura, T. and Hayakawa: Cooperative Binding and the Conformation of Poly(L-Glutamic Acid) in Guanidinium Salts with an Alkanoylamidoalkyl Group, J. Phys. Chem. B. 107 (2003) 8218–8222. DOI:10.1021/jp027178n10.1021/jp027178nSearch in Google Scholar

12 Hu, Y., Du, Y., Yang, J., Kennedy, J. F., Wang, X. and Wang, L.: Synthesis, Characterization and Antibacterial Activity of Guanidinylated Chitosan, Carbohydrate Polym. 67 (2007) 66–72. DOI:10.1016/j.carbpol.2006.04.01510.1016/j.carbpol.2006.04.015Search in Google Scholar

13 Sercheli, R., Vargas, R. M. and Schuchardt, U.: Alkylguanidine-Catalyzed Heterogeneous Transesterification of Soybean Oil, J. Am. Oi. Chem. Soc. 76 (1999) 1207–1210. DOI:10.1007/s11746-999-0095-210.1007/s11746-999-0095-2Search in Google Scholar

14 Bhattacharya, S. and Samanta, S. K.: Surfactants Possessing Multiple Polar Heads. A Perspective on Their Unique Aggregation Behavior and Applications, J. Phys. Chem. Lett. 2 (2011) 914–920. PMid:26295628; DOI:10.1021/jz200163410.1021/jz2001634Search in Google Scholar PubMed

15 Zhou, T., Ao, M., Xu, G., Liu, T. and Zhang, J.: Interactions of Bovine Serum Albumin with Cationic Imidazolium and Quaternary Ammonium Gemini Surfactants: Effects of Surfactant Architecture, J. Colloid Interface Sci. 389 (2013) 175–181. PMid:23044272; DOI:10.1016/j.jcis.2012.08.06710.1016/j.jcis.2012.08.067Search in Google Scholar PubMed

16 Di Michele, A., Brinchi, L., Di Profio, P., Germani, R., Savelli, G. and Onori, G.: Effect of Head Group Size, Temperature and Counterion Specificity on Cationic Aggregates, J. Colloid Interface Sci. 358 (2011) 160–166. PMid:21440896; DOI:10.1016/j.jcis.2010.12.02810.1016/j.jcis.2010.12.028Search in Google Scholar PubMed

17 Bhattacharya, S. and Haldar, J.: Thermodynamics of Micellization of Multi-headed Single-Chain Cationic Surfactants, Langmuir. 20 (2004) 7940–7947. PMid:15350056; DOI:10.1021/la049543310.1021/la0495433Search in Google Scholar PubMed

18 Bhattacharya, S. and Haldar, J.: Microcalorimetric and Conductivity Studies with Aggregates Prepared from Multi-Headed Pyridinium Surfactants, Langmuir. 21 (2005) 5747–5751. PMid:15952818; DOI:10.1021/la047072e10.1021/la047072eSearch in Google Scholar PubMed

19 Dong, B., Gao, Y., Su, Y., Zheng, L., Xu, J. and Inoue, T.: Self-Aggregation Behavior of Fluorescent Carbazole-Tailed Imidazolium Ionic Liquids in Aqueous Solutions, J. Phys. Chem. B. 114 (2009) 340–348. PMid:19845319; DOI:10.1021/jp908136f10.1021/jp908136fSearch in Google Scholar PubMed

20 Kang, E.-K., Lee, B. M., Wang, H. A. and Lim, J. C.: A Novel Cationic Surfactant Having Two Quaternary Ammonium Ions, J. Ind. Eng. Chem. 17 (2011) 845–852. DOI:10.1016/j.jiec.2011.09.00110.1016/j.jiec.2011.09.001Search in Google Scholar

21 Mohamed, A. S. and Mohamed, M. Z.: Preparation of Novel Cationic Surfactants from Epichlorohydrin: Their Surface Properties and Biological Activities, J. Surf. Det. 13 (2010) 159–163. DOI:10.1007/s11743-009-1141-710.1007/s11743-009-1141-7Search in Google Scholar

22 Nyuta, K., Yoshimura, T. and Esumi, K.: Surface Tension and Micellization Properties of Heterogemini Surfactants Containing Quaternary Ammonium Salt and Sulfobetaine Moiety, J. Colloid Interface Sci. 301 (2006) 267–273. PMid:16730355; DOI:10.1016/j.jcis.2006.04.07510.1016/j.jcis.2006.04.075Search in Google Scholar PubMed

23 Hou, Y., Cao, M., Deng, M. and Wang, Y.: Highly-Ordered Selective Self-Assembly of a Trimeric Cationic Surfactant on a Mica Surface, Langmuir. 24 (2008) 10572–10574. PMid:18781783; DOI:10.1021/la802021b10.1021/la802021bSearch in Google Scholar PubMed

24 Davey, T. W., Ducker, W. A. and Hayman, A. R.: Aggregation of x-Hydroxy Quaternary Ammonium Bolaform Surfactants, Langmuir. 16 (2000) 2430–2435. DOI:10.1021/la971303i10.1021/la971303iSearch in Google Scholar

25 Samanta, S. K., Bhattacharya, S. and Maiti, P. K.: Coarse-Grained Molecular Dynamics Simulation of the Aggregation Properties of Multiheaded Cationic Surfactants in Water, J. Phys. Chem. B. 113 (2009) 13545–13550. PMid:19775096; DOI:10.1021/jp902376y10.1021/jp902376ySearch in Google Scholar PubMed

26 Caillier, L., de Givenchy, E. T., Levy, R., Vandenberghe, Y., Géribaldi, S. and Guittard, F.: Synthesis and Antimicrobial Properties of Polymerizable Quaternary Ammoniums, Eur. J. Med. Chem. 44 (2009) 3201–3208. PMid:19380184; DOI:10.1016/j.ejmech.2009.03.03110.1016/j.ejmech.2009.03.031Search in Google Scholar PubMed

27 Skrzela, R., Para, G., Warszyníski, P. and Wilk, K. A.: Experimental and Theoretical Approach to Nonequivalent Adsorption of Novel Dicephalic Ammonium Surfactants at the Air/Solution Interface, J. Phys. Chem. B. 114 (2010) 10471–10480. PMid:20666437; DOI:10.1021/jp104980910.1021/jp1049809Search in Google Scholar PubMed

28 Srinivasa Rao, K., Singh, T., Trivedi, T. J. and Kumar, A.: Aggregation Behavior of Amino Acid Ionic Liquid Surfactants in Aqueous Media, J. Phys. Chem. B. 115 (2011) 13847–13853. PMid:22029384; DOI:10.1021/jp207627510.1021/jp2076275Search in Google Scholar PubMed

29 Song, Y., Li, Q. and Li, Y.: Self-Aggregation and Antimicrobial Activity of Alkylguanidinium Salts, Colloids Surf. A. 393 (2012) 11–16. 10.1016/j.colsurfa.2011.10.015Search in Google Scholar

30 Song, Y., Li, Q. and Li, Y.: Effect of Temperature and Added Counter Ions on Aggregate Formation of Guanidine Surfactants, Tenside Surf. Det. 49 (2012) 390–393. DOI:10.3139/113.11020710.3139/113.110207Search in Google Scholar

31 Song, Y., Li, Q., Li, Y. and Zhi, L.: Surface and Aggregation Properties of Heterogemini Surfactants Containing Quaternary Ammonium and Guanidine Moiety, Colloids Surf. A. 417 (2013) 236–242. 10.1016/j.colsurfa.2012.11.004Search in Google Scholar

32 Song, Y., Li, Q., Li, Y. and Zhi, L.: Synthesis and Properties of Dicephalic Cationic Surfactants Containing a Quaternary Ammonium and a Guanidine Group, J. Surf. Det. 16 (2013) 71–76. DOI:10.1007/s11743-012-1417-110.1007/s11743-012-1417-1Search in Google Scholar

33 Song, Y., Li, Q., Li, Y. and Zhi, L.: Biological Behaviors of Guanidine-Based Cationic Surfactants, J. Surf. Det. 17 (2014) 459–464. DOI:10.1007/s11743-013-1560-310.1007/s11743-013-1560-3Search in Google Scholar

34 Cabral, J. P. S. and Smith, A. R. W.: Determination of the Critical Aggregate Concentration of Dodecylguanidine Monoacetate (Dodine), J. Colloid Interface Sci. 149 (1992) 27–33. DOI:10.1016/0021-9797(92)90387-210.1016/0021-9797(92)90387-2Search in Google Scholar

35 Alonso-Moreno, C., Carrillo-Hermosilla, F., Garcs, A., Otero, A., Loípez-Solera, I., Rodriíguez, A. M. and Antiñolo, A.: Simple, Versatile, and Efficient Catalysts for Guanylation of Amines, Organometallics. 29 (2010) 2789–2795. DOI:10.1021/om100312210.1021/om1003122Search in Google Scholar

36 Zhang, Y., Li, Y., Song, Y. and Li, J.: Synthesis and Aggregation Behaviors of Tail-Branched Surfactant Guerbet-Cetyl Trimethyl Ammonium Chloride, Colloid Polym. Sci. 294 (2016) 271–279. DOI:10.1007/s00396-015-3771-910.1007/s00396-015-3771-9Search in Google Scholar

Received: 2019-12-07
Accepted: 2020-01-16
Published Online: 2021-03-13

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 19.3.2026 from https://www.degruyterbrill.com/document/doi/10.1515/tsd-2019-2241/html
Scroll to top button