Skip to main content
Log in

Synthesis and Characterization of Cationic Surfactants Based on N-Hexamethylenetetramine as Active Microfouling Agents

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

Four cationic surfactants of quaternary hexammonium silane chloride based on hexamethylenetetramine and alkyl chloride were synthesized. The chemical structures of the prepared cationic surfactants were elucidated using Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry analysis. The surface and thermodynamic properties of the prepared surfactants were also studied. The performance of these cationic surfactants as microfouling agents against two strains of Gram-negative bacteria, namely, Pseudomonas aeruginosa and Escherichia coli, and two strains of Gram-positive bacteria, namely, Staphylococcus aureus and Bacillus subtilis, were evaluated as antimicrobial agents. The results showed that the maximum antimicrobial activity was detected for N-hexamethylenetetramine-N-ethyl silane ammonium trichloride (Ah). The maximum and minimum antimicrobial activities were 73 and 60 % against S. aureus and E. coli, respectively, at a concentration of 5 mg/l, pH 7, and 37 °C.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Yebra DM, Kiil S, Dam JK (2004) Antifouling technology—past, present and future steps towards efficient and environmentally friendly antifouling coatings. Prog Org Coat 50:75–104

    Article  CAS  Google Scholar 

  2. Goncharov VI, Smolin VN (2007) Biofouling of equipment in waste treatment systems. Chem Technol Fuels Oils 43:252–253

    Article  CAS  Google Scholar 

  3. Lee AK, Newman DK (2003) Microbial iron respiration: impacts on corrosion processes. Appl Microbiol Biotechnol 62:134–139

    Article  CAS  Google Scholar 

  4. Jass J, Walker JT (2000) Biofilms and biofouling. In: Walker JT, Surman S, Jass J (eds) Industrial biofouling: detection, prevention and control. Wiley, New York, pp 1–12

    Google Scholar 

  5. Cloete TE, Jacobs L, Brozel VS (1998) The chemical control of biofouling in industrial water systems. Biodegradation 9:23–37

    Article  CAS  Google Scholar 

  6. Shirai A, Sumitomo T, Kurimoto M, Maseda H, Kourai H (2009) The mode of the antifungal activity of gemini-pyridinium salt against yeast. Biocontrol Sci 14:13–20

    Article  CAS  Google Scholar 

  7. Hoque J, Akkapeddi P, Yarlagadda V, Uppu DS, Kumar P, Haldar J (2012) Cleavable cationic antibacterial amphiphiles: synthesis, mechanism of action, and cytotoxicities. Langmuir 28:12225–12234

    Article  CAS  Google Scholar 

  8. McCarron PA, Donnelly RF, Marouf W, Calvert DE (2007) Anti-adherent and antifungal activities of surfactant-coated poly(ethylcyanoacrylate) nanoparticles. Int J Pharm 340:182–190

    Article  CAS  Google Scholar 

  9. Domagk G (1935) Dtsch Med Wochenschr 24:829–832

    Article  Google Scholar 

  10. Klarmann W (1946) Soap Sanit Chemicals 22:125

  11. Brunt KD (1987) In: Hill HC (ed) Biocides for the oil industry. Wiley, New York, pp 201–207

  12. Rozga-Wijas K, Mizerska U, Fortuniak W, Chojnowski J, Hałasa R, Werel W (2007) Quaternary ammonium salts (QAS) modified polysiloxane biocide supported on silica materials. J Inorg Organomet Polym 17:605–613

    Article  CAS  Google Scholar 

  13. Dizman B, Elasri MO, Mathias LJ (2006) Synthesis and antibacterial activities of water-soluble methacrylate polymers containing quaternary ammonium compounds. J Polym Sci Part A Polym Chem 44:5965–5973

    Article  CAS  Google Scholar 

  14. Kugler R, Boulossa O, Rondelez F (2005) Evidence of a charge-density threshold for optimum efficiency of biocidal cationic surfaces. Microbiol 151:1341–1348

    Article  CAS  Google Scholar 

  15. Arnt L, Nusslein K, Tew GN (2004) Nonhemolytic abiogenic polymers as antimicrobial peptide mimics. J Polym Sci Part A Polym Chem 48:3860–3864

    Article  Google Scholar 

  16. Gabrielska J, Sarapuk J, Przestalski S, Wroclaw P (1994) Tenside Surfact Deterg 31:296

    CAS  Google Scholar 

  17. Kawabata N, Nishiguchi M (1988) Antibacterial activity of soluble pyridinium-type polymers. Appl Environ Microbiol 54:2532–2535

    CAS  Google Scholar 

  18. Caillier L, de Givenchy ET, Levy R, Vandenberghe Y, Géribaldi S, Guittard F (2009) Synthesis and antimicrobial properties of polymerizable quaternary ammoniums. Eur J Med Chem 44:3201–3208

    Article  CAS  Google Scholar 

  19. Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken HR (1995) Manual of clinical microbiology, 6th edn. ASM Press, Washington, pp 15–18

    Google Scholar 

  20. Olurinola PF (1996) A laboratory manual of pharmaceutical microbiology. Idu, Abuja, pp 69–105

    Google Scholar 

  21. Kaya O, Akçam F, Yaylı G (2012) Investigation of the in vitro activities of various antibiotics against Brucella melitensis strains. Turk J Med Sci 42:145–148

    CAS  Google Scholar 

  22. Noor El-Din MR, Al-Sabagh AM, Hegazy MA (2012) Study of the inhibition efficiency for some novel surfactants on the carbon steel (Type H-11) pipelines in 0.5 M HCl solution by potentiodynamic technique. J Dispersion Sci Technol 33:1444–1451

    Article  CAS  Google Scholar 

  23. Sayem Alam M, Asit BM (2012) Thermodynamic studies on mixed micellization of amphiphilic drug amitriptyline hydrochloride and nonionic surfactant Triton X-100. J Mol Liq 168:75–79

    Article  Google Scholar 

  24. Pavlikova-Moricka M, Lacko I, Devinsky F, Masarova L, Milynarcik D (1994) Quantitative relationships between structure and antimicrobial activity of new “soft” bisquaternary ammonium salts. J Folia Microbiol (Praha) 39:176–180

    Article  CAS  Google Scholar 

  25. Nikaido H (1996) Outer membrane. In: Neidhardt FC (ed) Escherichia coli and Salmonella typhimurium, cellular and molecular biologym. American Society for Microbiology Press, Washington, DC

    Google Scholar 

  26. Gao Y, van Belkum MJ, Stiles ME (1999) The outer membrane of Gram negative bacteria inhibits antibacterial activity of brochocin-C. Appl Environ Microbiol 65:4329–4333

    CAS  Google Scholar 

  27. Badawi AM, Hafiz AA (2007) Synthesis and immunomodulatory activity of some novel amino acid germinates. J Iran Chem Soc 4:107–113

    Article  CAS  Google Scholar 

  28. Argyropoulou I, Geronikaki A, Paola V, Zani F (2009) Synthesis the biological evalution of sulfonamide thiazole and benzothiazole deriviatives as antimicrobial agents. Arkivoc 4:89–102

    Article  Google Scholar 

  29. Santhakumar K, Kumaraguru N, Arumugham MN, Arunachalam S (2006) Metallomicelles of Co(III) coordination complexes-synthesis, characterization and determination of CMC values. Polyhedron 25:1507–1513

    Article  CAS  Google Scholar 

  30. Rosen MJ (2004) Surfactants and interfacial phenomena, 3rd edn. Wiley, New York

  31. Badawi AW, El-Bayouki KhA, Zakria VR (1985) Acetanilide sulphonyl hydrazides and hadrazones of biological activity. Oriental J Chem 1:78

    CAS  Google Scholar 

  32. Rosen MJ (1989) Surfactants and interfacial phenomena, 2nd edn. Wiley, New York

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mahmoud R. Noor El-Din.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 381 kb)

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohareb, R.M., Badawi, A.M., Noor El-Din, M.R. et al. Synthesis and Characterization of Cationic Surfactants Based on N-Hexamethylenetetramine as Active Microfouling Agents. J Surfact Deterg 18, 529–535 (2015). https://doi.org/10.1007/s11743-014-1662-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-014-1662-6

Keywords

Navigation