Skip to main content
SpringerLink
Log in

Glycosilicones

  • Conference paper
Silicon Based Polymers

Abstract

This article reviews the methods described to date for the preparation of polysiloxanes with well-defined structures containing sugar groups either as sidechain groups, end-groups or included in the main chain.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. T.K. Lindhorst, “Essentials of Carbohydrate Chemistry and Biochemistry”, 2007, Wiley VCH Ed., Chap 6, 213–237.

    Google Scholar 

  2. Patent A.J. O’Lenick, US 5,428,142 (27/06/1995)

    Google Scholar 

  3. J. Fitremann, Unpublished results.

    Google Scholar 

  4. e.g. patents WO 02/088456 (07/11/2002), WO 2006/127924 (30/11/2006).

    Google Scholar 

  5. K. Beppu, Y. Kaneko, J-I. Kadokawa, H. Mori, T. Nishikawa, Polymer J., 2007, 39(10), 1065–1070. “Synthesis of sugar-polysiloxane hybrids having rigid main-chain and formation of their nano -aggregates”

    Google Scholar 

  6. R. Wagner, L. Richter, R. Wersig, G. Schmaucks, B. Weiland, J. Weissmueller, J. Reiners, Appl. Organometal. Chem., 1996, 10(6), 421–435. “Silicon-modified carbohydrate surfactants. I. Synthesis of siloxanyl moieties containing straight-chained glycosides and amides.”

    Article  CAS  Google Scholar 

  7. R. Wagner, L. Richter, B. Weiland, J. Reiners, J. Weissmüller, Appl. Organometal. Chem., 1996, 10(6), 437–450. “Silicon-modified carbohydrate surfactants. II. Siloxanyl moieties containing branched structures.”

    Article  CAS  Google Scholar 

  8. R. Wagner, L. Richter, B. Weiland, J. Weissmüller, J. Reiners, W. Kraemer, Appl. Organometal. Chem., 1997, 11(6), 523–538. “Silicon-modified carbohydrate surfactants.III. Cationic and anionic compounds.”

    Article  CAS  Google Scholar 

  9. T. Dietz, B. Gruning, P. Lersch, C. Weitemeyer, US 5,891,977, 06/04/1999. “Organopolysiloxanes comprising polyhydroxorganyl radicals and polyoxyalkylene radicals”.

    Google Scholar 

  10. G. Torres, G. Wajs, FR 2646672, 11/09/1990. “Elastomère de silicone mouillable convenant à la fabrication de lentilles de contact”.

    Google Scholar 

  11. R. Wersig, G. Sonnek, C. Niemann, Appl. Organomet. Chem. 1992, 6, 701–708. “Novel nonionic siloxane surfactants”

    Article  CAS  Google Scholar 

  12. G. Jonas, R. Stadler, Makromol. Chem., Rapid Commun. 1991, 12, 625 “Polysiloxanes with statistically distributed glucose and galactose units, 1: Synthesis and thermal characterization”

    Google Scholar 

  13. G. Jonas, R. Stadler, Acta Polymer., 1994, 45, 14–20. “Carbohydrate modified polysiloxanes II. Synthesis via hydrosilation of mono-, di-and oligosaccharide allylglycosides”.

    Google Scholar 

  14. K. Loos, G. Jonas, R. Stadler, Macromol. Chem. Phys. 2001, 202, 3210–3218, “Carbohydrate Modified Polysiloxanes, 3. Solution Properties of carbohydrate-Polysiloxane conjugates in Toluene”.

    Article  CAS  Google Scholar 

  15. V. von Braunmühl, R. Stadler, Polymer, 1998, 65, 1617. “Synthesis of aldonamide siloxanes by hydrosilylation”.

    Article  Google Scholar 

  16. T. Akimoto, K. Kawahara, Y. Nagase, T. Aoyagi, Macromol. Chem. Phys., 2000, 201(18), 2729–2734. “Preparation of oligodimethylsiloxanes with sugar moiety at a terminal group as a transdermal penetration enhancer”.

    Article  Google Scholar 

  17. T. Akimoto, K. Kawahara, Y. Nagase, T. Aoyagi, J. Control. Release, 2001, 77, 49–51. “Polymeric transdermal drug penetration enhancer: The enhancing effect of oligodimethylsiloxane containing a glucopyranosyl end group”.

    Article  CAS  Google Scholar 

  18. T. Akimoto, Y. Nagase, J. Control. Release, 2003, 88, 243–252. “Novel transdermal drug penetration enhancer: synthesis and enhancing effect of alkyldisiloxane compounds containing glucopyranosyl group”.

    Google Scholar 

  19. M. Haupt, S. Knaus, T. Rohr, H. Gruber, J. Macromol. Sci. Pure Appl. Chem. 2000, A37(4), 323–341. “Carbohydrate modified polydimethylsiloxanes. Part 1. Synthesis and Characterization of carbohydrate silane and siloxane building blocks”

    CAS  Google Scholar 

  20. D. Henkensmeier, B. C. Abele, A. Candussio, J. Thiem, Macromol. Chem. Phys., 2004, 205, 1851–1857. “Synthesis and characterization of terminal carbohydrate modified polydimethylsiloxanes”.

    Article  CAS  Google Scholar 

  21. C. Racles, T. Hamaide, Macromol. Chem. Phys., 2005, 206, 1757–1768. “Synthesis and characterization of water soluble saccharide functionalized polysiloxanes and their use as polymer surfactants for the stabilization of polycaprolactone nanoparticles.”

    Article  CAS  Google Scholar 

  22. C. Racles, T. Hamaide, A. Ioanid, Appl. Organometal. Chem. 2006, 20(4), 235–245. “Siloxane surfactants in polymer nanoparticles formulation.”

    Article  CAS  Google Scholar 

  23. E. Fleury, Patent WO 2005 087843, 22/09/2005. “Grafted polymers comprising a polyorganosiloxane backbone and glycoside units”.

    Google Scholar 

  24. ISPO International Symposium, Montpellier (Mèze, France), juin 2007.

    Google Scholar 

  25. E. Fleury, S. Halila, H. Driguez, S. Cottaz, T. Hamaide, S. Fort, FR 2 900 931, 16/11/2007. “Hybrid compounds based on silicones and at least one another polymer or nonpolymer molecular entity bonded to the silicone chains by nitrogen-containing rings, their preparation process, and their applications.”

    Google Scholar 

  26. T. Ogawa, J. Polymer Sci., Part A: Polymer Chem. 2003, 41(21), 3336–3345. “Simplified synthesis of carbohydrate-functional siloxanes via transacetalation. I. Glucose-functional siloxanes”.

    Article  CAS  Google Scholar 

  27. T. Ogawa, Macromol. 2003, 36(22), 8330–8335. “Simplified Synthesis of Amphiphilic Siloxanes with Methyl Gluconyl Glycinate Functionalities via Transacetalation”.

    Article  CAS  Google Scholar 

  28. V. von Braunmühl, G. Jonas, R. Stadler, Macromol., 1995, 28, 17–24. “Enzymatic grafting of amylose from polydimethylsiloxanes”.

    Article  Google Scholar 

  29. V. v. Braunmühl, R. Stadler, Macromol. Symp. 1996, 103, 141–148. “Polydimethylsiloxanes with amylose side chains by enzymatic polymerization”

    Google Scholar 

  30. B. Sahoo, K.F. Brandstadt, T.H. Lane, R.A. Gross, Organic Lett. 2005, 7(18), 3857–3860. “Sweet Silicones”: Biocatalytic Reactions to Form Organosilicon Carbohydrate Macromers”.

    Article  CAS  Google Scholar 

  31. B. Sahoo, K.F. Brandstadt, T.H. Lane, R.A. Gross, in “Polymer Biocatalysis and Biomaterials”, ACS Symposium Series, 2005, 900, 182–190. “Sweet silicones”: Biocatalytic reactions to form organosilicon carbohydrate macromers”.

    Article  CAS  Google Scholar 

  32. D. Henkensmeier, B. C. Abele, A. Candussio, J. Thiem, Polymer, 2004, 7053–7059, -“Synthesis, characterisation and degradability of polyamides derived from aldaric acids and chain end functionalised polydimethylsiloxanes”.

    Google Scholar 

  33. A. Domschke, D. Lohmann, J. Höpken, EP 0826158, 15/09/1999.

    Google Scholar 

  34. R. Wagner,; Y. Wu, L. Richter, T. Pfohl, S. Siegel, J. Weissmueller, J. Reiners, Appl. Organometal. Chem., 1996, 10(6), 421–435. “Silicon containing structures at interfaces. The wetting behavior of carbohydrate-modified Si surfactants on perfluorinated surfaces and the modification of rough metal surfaces by hydrophilic polysiloxane networks.”

    Article  CAS  Google Scholar 

  35. R. Wagner, L. Richter, Y. Wu, J. Weissmuller, J. Reiners, K.-D. Klein, D. Schaefer, S. Stadtmuller, in Organosilicon Chemistry III: From Molecules to Materials, N. Auner, J. Weis, Eds, 1998, 510–514.“Carbohydrate-modified siloxane surfactants: The effect of substructures on the wetting behavior on non polar solid surfaces.

    Google Scholar 

  36. R. Wagner, L. Richter, Y. Wu, J. Weissmuller, A. Kleewein, E. Hengge, Appl. Organometal. Chem., 1998, 12(4), 265–276. “Silicon-modified carbohydrate surfactants. VII: Impact of different silicon substructures on the wetting behavior of carbohydrate surfactants on low-energy surfaces – distance decay of donor-acceptor forces.”

    Article  CAS  Google Scholar 

  37. R. Wagner, Y. Wu, L. Richter, S. Siegel, J. Weissmuller, J. Reiners, Appl. Organometal. Chem., 1998, 12(12), 843–853. “Silicon-modified carbohydrate surfactants IX: dynamic wetting of a perfluorinated solid surface by solutions of a siloxane surfactant above and below the critical micelle concentration.”

    Article  CAS  Google Scholar 

  38. R. Wagner, Y. Wu, L. Richter, J. Reiners, J. Weissmuller, A. De Montigny, Appl. Organometal. Chem., 1999, 13(1), 21–28. “Silicon-modified carbohydrate surfactants. VIII. equilibrium wetting of perfluorinated solid surfaces by solutions of surfactants above and below the critical micelle concentration-surfactant distribution between liquid-vapor and solid-liquid interfaces.”

    Google Scholar 

  39. Eur. Polymer J., 2004, 40, 165–170.

    Google Scholar 

  40. Carbohydr. Polymers, 2006, 65, 321–326.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire des Interactions Moléculaires et Réactivité Chimique et Photochimique, Université de Toulouse, UMR 5623 CNRS – Université Paul Sabatier, Bâtiment 2R1, 118 Route de Narbonne, F-31062, Toulouse Cedex 9, France

    Juliette Fitremann, Waêl Moukarzel & Monique Mauzac

Authors
  1. Juliette Fitremann
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Waêl Moukarzel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Monique Mauzac
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Juliette Fitremann .

Editor information

Editors and Affiliations

  1. Ecole Nationale Supérieure de Chimie de Montpellier, UMR 5253 - Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, 8 rue de l’Ecole Normale, 34296, Montpellier CX 05, France

    François Ganachaud

  2. Institut de Chimie et des Matériaux, Paris-Est (ICMPE) SPC-CNRS, 2 à 8 rue Henri Dunant, 94320, Thiais, France

    Sylvie Boileau

  3. Université Montpellier II, Institut Charles Gerhardt, Chimie Moléculaire et organisation du solide, place Eugène Bataillon, 34095, Montpellier CX 05, France

    Bruno Boury

Rights and permissions

Reprints and permissions

Copyright information

© 2008 Springer Science+Business Media B.V.

About this paper

Cite this paper

Fitremann, J., Moukarzel, W., Mauzac, M. (2008). Glycosilicones. In: Ganachaud, F., Boileau, S., Boury, B. (eds) Silicon Based Polymers. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8528-4_13

Download citation

Publish with us

Policies and ethics

Search

Navigation