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Cleavable Ortho Ester Type Surfactants

  • P.-E. Hellberg and C. G. van Ginkel
Published/Copyright: May 8, 2013
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 41 Issue 6

Abstract

With the focus on quaternary ammonium compounds, this paper describes how the ortho ester chemistry can be used as a versatile tool for synthesis of cleavable surfactants of various types. This class of chemodegradable surfactants hydrolyzes rapidly under mild acidic conditions at the same time as they are long-term stable in alkaline aqueous solutions.

Further, the rate of cleavage can be modified by varying the structure of the surfactant. An additional feature is the possibility to design surface active compounds that release a daughter surfactant with different properties upon cleavage. Ortho ester-based surfactants could be of use in a large number of applications as exemplified in the paper.

Good biodegradation data are of importance for virtually all types of surfactants nowadays. However, there actually seem to exist very few, if any, investigations regarding the biodegradation of cleavable surfactants under both hydrolytical and non-hydrolytical conditions.

Data from the initial part of such a study on cationic ortho ester surfactants are presented and discussed in this paper. The results strongly indicate rapid biodegradation for this class of compounds under varying conditions.

Kurzfassung

Mit dem Schwerpunkt quaternärer Ammoniumverbindungen beschreibt diese Arbeit, wie die Ortho-Esterchemie als ein vielseitiges Werkzeug für die Synthese verschiedener Arten von spaltbaren Tensiden genutzt werden kann. Diese Gruppe der chemisch abbaubaren Tenside hydrolysiert schnell unter leicht-sauren Bedingungen und ist dagegen in alkalisch-wässrigen Lösungen über längere Zeit stabil. Darüber hinaus kann die Spaltungsrate durch Variation der Tensidstruktur modifiziert werden. Eine zusätzliche Möglichkeit ist die Darstellung von oberflächenaktiven Substanzen, die bei der Spaltung Tochter-Tenside mit unterschiedlichen Eigenschaften freisetzen. In dieser Arbeit werden Beispiele für einer Vielzahl von Anwendungen von Tensiden auf Ortho-Ester-Basis gegeben.

Eine gute biologische Abbaubarkeit ist heutzutage für praktisch alle Arten von Tensiden von hoher Bedeutung. Tatsächlich scheint es jedoch nur sehr wenige Untersuchungen zu geben, die die biologische Abbaubarkeit von spaltbaren Tensiden unter hydrolytischen und nicht-hydrolytischen Bedingungen betrachten. Einige der Daten einer Erstuntersuchung über kationische Ortho-Ester-Tenside werden in dieser Arbeit vorgestellt und besprochen. Die Resultate zeigen für diese Kategorie von Verbindungen eine ausgezeichnete und schnelle biologische Abbaubarkeit unter verschiedenen Bedingungen.

Keywords:: Surfactant; ortho ester; cleavable; cationic; biodegradation
Schlüsselwörter: Tenside; Ortho-Ester; Spaltbarkeit; kationische Tenside; biologische Abbaubarkeit
3Per-Erik Hellberg, Akzo Nobel Surface Chemistry AB, SE-444 85 Stenungsund, Sweden, E-mail:

C. G. van Ginkel received his Ph.D in microbiology from Agricultural University, Wageningen, the Netherlands in 1987. He has worked as an environmental scientist in the chemical industry (Akzo Nobel) since graduation. His major research activities have focused on the environmental fate of chemicals used in detergents.

Per-Erik Hellberg, received his M.Sc. in Chemical Engineering from Chalmers University of Technology, Gothenburg in 1986 and his Licentiate of Engineering in Chemistry from the same university in 2002. In 1987 he joined Akzo Nobel Surface Chemistry AB (then Berol Kemi AB), where he presently keeps a position as R&D Specialist. He has worked with new surfactants for Enhanced Oil Recovery (EOR) for a number of years in the end of the 80's and beginning of the 90's while the main interest since 1994 has been in the field of cleavable surfactants.

References

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Received: 2004-8-18
Published Online: 2013-05-08
Published in Print: 2004-12-01

© 2004, Carl Hanser Publisher, Munich

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  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Application
  6. Nonionic Tenside Ligands and its Application in Biphasic Catalysis
  7. Detergent Ingredient
  8. Synthesis of δ Layered Sodium Disilicate with High Framework Stability
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https://doi.org/10.3139/113.100233
Keywords for this article
Surfactant; ortho ester; cleavable; cationic; biodegradation

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Application
  6. Nonionic Tenside Ligands and its Application in Biphasic Catalysis
  7. Detergent Ingredient
  8. Synthesis of δ Layered Sodium Disilicate with High Framework Stability
  9. Novel Surfactants
  10. Cleavable Ortho Ester Type Surfactants
  11. GDCH Special Group Meeting
  12. Development and Analytic of Odor Absorber
  13. Enzymatic Production of Care Specialties Based on Fatty Acid Esters
  14. Are Oxygen Demands Relevant for Today's Environmental Assessment of Detergents?
  15. 30th Anniversary of the Expert Group Detergent Chemistry: From an Isolated Problem Solving to Sustainable Responsibility
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