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Hyperbranched Polyamidoamine Surfactants: Synthesis, Characterization and Evaluation as Biocides

  • Tawfik M. Kassem , El-Sayed Ahmed Soliman , Ammona S. Mohamed , Dalia E. Mohamed and Fatma M. Abdelhafiz
Published/Copyright: November 16, 2018
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 55 Issue 6

Abstract

Different generations of cationic hyperbranched quaternary ammonium polyamidoamine dendrimers (PAMAM) with methyl ester end group (G-0.5, G 0.5, G1.5 and G 2.5) were synthesized. Preparation of these dendrimers was carried out via alternative steps of an aza Michael addition reaction (of piperazine as core center molecule) and amidation reaction by ethylene diamine. Each aza Michael addition step was followed by a quaternization step using alkyl bromide with different chain length (4, 8 or 12) carbon atoms. The chemical structures of the prepared dendrimers were confirmed using FTIR, 1H-NMR spectra and elemental analysis for two generations as representative compounds. Also their surface activity has been studied and their surface parameters including surface and interfacial tension, emulsification power, critical micelle concentration, effectiveness, efficiency, maximum surface excess and minimum surface area were determined. The prepared quaternized dendrimers were tested as antimicrobial agents against different strains of bacteria, yeast and fungi. The results showed a significant antimicrobial efficacy of the synthesized surfactants.

Kurzfassung

Verschiedene Generationen von, kationischen, hyperverzweigten quaternären Ammonium-Polyamidoamin (PAMAM)-Dendrimeren mit endständigen Methylestergruppen (G-0,5, G-0,5, G-1,5 und G-2,5) wurden synthetisiert. Die Herstellung dieser Dendrimere erfolgte über alternative Schritte der Aza-Michael-Additionsreaktion (von Piperazin als Kernzentrummolekül) und einer Amidierungsreaktion durch Ethylendiamin. Jedem Aza-Michael-Additionsschritt folgte der Quaternisierungsschritt unter Verwendung von Alkylbromid mit 4, 8 oder 12 Kohlenstoffatomen in der Alkylkette. Die chemischen Strukturen der hergestellten Dendrimere wurden mittels FTIR- und 1H-NMR-Spektren sowie der Elementaranalyse für zwei Generationen als repräsentative Verbindungen bestätigt. Auch ihre Oberflächenaktivität wurde untersucht; ihre Oberflächenparameter (Oberflächen- und Grenzflächenspannung, Emulgiervermögen, kritische Mizellenbildungskonzentration, Wirksamkeit, Effizienz, maximaler Oberflächenüberschuss und minimale Oberfläche) wurden bestimmt. Die hergestellten quaternisierten Dendrimere wurden als antimikrobielle Mittel gegen verschiedene Bakterien-, Hefe- und Pilzstämme getestet. Die Ergebnisse zeigten eine signifikante antimikrobielle Wirksamkeit der synthetisierten Tenside.

Key words: Piperazine; ethylene diamine; Michael addition reaction; hyperbranched polyamidoamine; antimicrobial agents
Stichwörter: Piperazin; Ethylendiamin; Michael-Additionsreaktion; hyperverzweigte Polyamidoamine; antimikrobielle Verbindungen
*Correspondence address, Prof. Dr. Dalia E. Mohamed, Egyptian Petroleum Research Institute, 11727, Nasr City, Cairo, Egypt

Tawfik M. Kassem received his B.Sc. from Ain Shams University (1964), M.Sc. from Cairo University (1968) and Ph.D. from Ain Shams University (1973). He is Professor of Petrochemicals in the Petrochemicals Department (Egyptian Petroleum Research Institute, EPRI). His interests are focused on the synthesis and evaluations of surfactants in several fields including, biocidal application and solubilization.

El-Sayed Ahmed Soliman received his Ph.D. in organic chemistry from Ain Shams University in 1974. He has been Head of the Chemistry Department (Faculty of Science) at Ain Shams University since 2006, as well as a Professor in Houria Boumediene University for Science and Technology, Institute of Chemistry, Algeria, from 1986 to 1990.

Ammona S. Mohamed received her B.Sc. and M.Sc. from the Suez Canal University and her Ph.D. from Ain Shams University (2000). She is presently Professor of Applied Surfactants in the Petrochemicals Department (Egyptian Petroleum Research Institute, EPRI). Her interests are focused on the synthesis and evaluations of surfactants in several fields including, biocidal application, solubilization, and antitumor activity.

Dalia E. Mohamed received her B.Sc. and M.Sc. from Cairo University and a Ph.D. from Ain Shams University. She is presently associate Professor at the Egyptian Petroleum Research Institute (Surfactants Laboratory). Her research interests are focused on synthesis, properties and applications of new surfactants.

Fatma M. Abdelhafiz received her B.Sc. from Ain Shams University (2006) and M.Sc. from Benha University (2013). She is presently researcher assistant at the Egyptian Petroleum Research Institute (Surfactants Laboratory). Her interests are focused on synthesis, properties and applications of new surfactants in several fields.

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Published Online: 2018-11-16
Published in Print: 2018-11-16

© 2018, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents/Inhalt
  3. Short Communication
  4. Obsolescence of Large Household Appliances in Germany
  5. Review Article
  6. Quaternary Alkylammonium Salts as Cleaning and Disinfectant Agents
  7. Application
  8. Effect of N-dodecyl-N-(propylpiperydinium-3-sulfonate) on Usage Properties of Liquid Soaps for Sensitive Skin
  9. Surfactant Analysis
  10. Characterization of Tween® Surfactants by MALDI TOF-MS and High Performance Liquid Chromatography in a Ternary Mobile Phase
  11. Novel Surfactants
  12. Hyperbranched Polyamidoamine Surfactants: Synthesis, Characterization and Evaluation as Biocides
  13. Fermentative Production of Sophorolipid and Purification by Adsorption Chromatography
  14. Physical Chemistry
  15. A Comparison Study on the Phase Behavior and Solubilization between Cn(Bim)2-2Br-Butyric Acid and CnmimBr-Butyric Acid Microemulsion Systems
  16. Effect of Alkyl Tail Length of Alpha Olefin Sulfonates on Foam Properties
  17. Impact of Spacer and Hydrophobic Tail on Interfacial and Rheological Properties of Cationic Amido-Amine Gemini Surfactants for EOR Application
  18. Environmental Chemistry
  19. Role of Surfactants Cetyl Pyridinium Chloride (CPC) and Cetyltrimethyl Ammonium Bromide (CTAB) in the Reverse Micellar Extraction of Ternary Mixture of Acid Dyes from Textile Effluent
https://doi.org/10.3139/113.110587
Keywords for this article
Piperazine; ethylene diamine; Michael addition reaction; hyperbranched polyamidoamine; antimicrobial agents

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents/Inhalt
  3. Short Communication
  4. Obsolescence of Large Household Appliances in Germany
  5. Review Article
  6. Quaternary Alkylammonium Salts as Cleaning and Disinfectant Agents
  7. Application
  8. Effect of N-dodecyl-N-(propylpiperydinium-3-sulfonate) on Usage Properties of Liquid Soaps for Sensitive Skin
  9. Surfactant Analysis
  10. Characterization of Tween® Surfactants by MALDI TOF-MS and High Performance Liquid Chromatography in a Ternary Mobile Phase
  11. Novel Surfactants
  12. Hyperbranched Polyamidoamine Surfactants: Synthesis, Characterization and Evaluation as Biocides
  13. Fermentative Production of Sophorolipid and Purification by Adsorption Chromatography
  14. Physical Chemistry
  15. A Comparison Study on the Phase Behavior and Solubilization between Cn(Bim)2-2Br-Butyric Acid and CnmimBr-Butyric Acid Microemulsion Systems
  16. Effect of Alkyl Tail Length of Alpha Olefin Sulfonates on Foam Properties
  17. Impact of Spacer and Hydrophobic Tail on Interfacial and Rheological Properties of Cationic Amido-Amine Gemini Surfactants for EOR Application
  18. Environmental Chemistry
  19. Role of Surfactants Cetyl Pyridinium Chloride (CPC) and Cetyltrimethyl Ammonium Bromide (CTAB) in the Reverse Micellar Extraction of Ternary Mixture of Acid Dyes from Textile Effluent
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