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Synthesis and Properties of Sugar-Based Gemini Surfactants

  • J. Shi , Q.-D. Li und X.-C. Xia
Veröffentlicht/Copyright: 31. März 2013
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 43 Heft 4

Abstract

A series of new gemini surfactants having hydrophilic glucosides were synthesized from glucose via two different synthesis roads, including N,N′-didodecyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl)-p-phthaloyl amide [B(DG)PA], N,N′-didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-2,5-dicarboxylate p-phthaloyl amide [B(DGC)PA], N,N′-didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl) ethylenediamine [B(DG)EA], and N,N′-didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl) hexanediamine [B(DG)HA]. The final products were characterized by IR and NMR spectral measurements and by interfacial tension measurements. The critical micellar concentrations (cmc) of these gemini surfactants were determined to be 2.49 × 10−6, 1.93 × 10−6, 2.47 × 10−6 and 1.66 × 10−6 mol L−1, respectively, which are about one order of magnitude lower than the corresponding monomeric surfactants (GHPDA). The results showed that these synthesized sugar-based gemini surfactants had high abilities to reduce the surface or oil-water interface tension. The high surface activity of these synthesized molecules was attributed to their unique structure where two optimally spaced hydrophobic chains and hydrophilic groups were present.

Kurzfassung

Eine Reihe von neuen Gemini-Tensiden mit hydrophilen Glycosiden wurde auf zwei verschiedenen Wegen aus Glukose synthetisiert, dazu gehören N,N′-Didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-p-phthaloylamid [B(DG)PA], N,N′Didodecyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)-2,5-dicarboxylat-p-phthaloylamid [B(DGC)PA], N,N′-Didodecanoyl-N,N′-bis(1-glucosyl-2-hydroxyl-propyl)ethylendiamin [B(DG)EA] und N,N′-Didodecanoyl-N,N′-bis-(1-glucosyl-2-hydroxyl-propyl)hexandiamin [B(DG)HA]. Die Endprodukte wurden durch IR- und NMR-Spektralmessungen sowie Messungen der Grenzflächenspannung charakterisiert. Die kritischen Mizellbildungskonzentrationen (cmc) dieser Gemini-Tenside wurden zu 2,49 × 10−6, 1,93 × 10−6, 2,47 × 10−6 und 1,66 × 10−6 mol L−1 bestimmt, die jeweils eine Größenordnung niedriger sind als die entsprechenden monomeren Tenside (GHPDA). Die Ergebnisse zeigen, dass diese zuckerbasierten Gemini-Tenside ein hohes Vermögen zur Reduzierung der Oberflächen- oder Öl-Wasser-Grenzflächenspannung besitzen. Die hohe Oberflächenaktivität dieser synthetisierten Moleküle ist auf die vorliegende einzigartige Struktur, mit zwei räumlich optimierten hydrophoben Ketten und hydrophilen Gruppen, zurückzuführen.

Key words:: Gemini surfactants; glucoside; synthesis; properties; cmc
Stichwörter:: Gemini-Tenside; Glucoside; Synthese; Eigenschaften; cmc
∗ Jun Shi, Department of Chemistry, College of Chemistry & Chemical Engineering, Xi'an Shiyou University, 710065 Xi'an, P.R. China, Tel.: +86(0)2988382697, Fax: +86(0)2988234429. E-mail:

Jun Shi, born in 1963, is an associate professor in the College of Chemistry & Chemical Engineering at Xi'an Shiyou University, China. He is specialized in the area of synthesis and analysis of fine chemicals, and has published more than 30 papers in the related area in recent years. Jun Shi can be reached by telephone: +862988382697 (o), +862988383869 (h) or email: .

Qianding Li, born in 1959, is a professor in the college of Chemistry & Chemical Engineering at Xi'an Shiyou University, China. He is mainly engaged in the research of applied chemistry and administrative job, and has published more than 50 papers in the related area in recent years. Qianding Li can be reached by telephone: +862988382321 (o), or email: .

Xiaochun Xia, born in 1976, is an engineer in the China Oilfield Services Limited. Now he is specialized in the research of oilfield chemistry. Xiaochun Xia can be reached by telephone: +861084522115, or email: .

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Received: 2006-04-06
Accepted: 2006-05-16
Published Online: 2013-03-31
Published in Print: 2006-09-01

© 2006, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Analysis
  6. Analysis of the Sucrose Fatty Acid Esters by Atmospheric-pressure Ionization MS with Electrospray Ionization Spectrometry
  7. Application
  8. Influence of Natural and Synthetic Additives on Calcium Carbonate Precipitation and Crystal Morphology
  9. Physical Chemistry
  10. Effect of Micelles on the Dynamic Surface Tension of Zwitterionic Surfactants
  11. Microemulsions Using Hexaethylene Glycol Mono-n-dodecyl Ether Nonionic Surfactant and Small Amount of Ionic Surfactants
  12. Synthesis
  13. Synthesis and Properties of Sugar-Based Gemini Surfactants
  14. Synthesis and Properties of Al-δ Layered Sodium Disilicate with High Framework Stability
https://doi.org/10.3139/113.100309
Schlagwörter für diesen Artikel
Gemini surfactants; glucoside; synthesis; properties; cmc

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Analysis
  6. Analysis of the Sucrose Fatty Acid Esters by Atmospheric-pressure Ionization MS with Electrospray Ionization Spectrometry
  7. Application
  8. Influence of Natural and Synthetic Additives on Calcium Carbonate Precipitation and Crystal Morphology
  9. Physical Chemistry
  10. Effect of Micelles on the Dynamic Surface Tension of Zwitterionic Surfactants
  11. Microemulsions Using Hexaethylene Glycol Mono-n-dodecyl Ether Nonionic Surfactant and Small Amount of Ionic Surfactants
  12. Synthesis
  13. Synthesis and Properties of Sugar-Based Gemini Surfactants
  14. Synthesis and Properties of Al-δ Layered Sodium Disilicate with High Framework Stability
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