Feature Article

Lactic Acid-Based Functionalized Polymers via Copolymerization and Chemical Modification

  1. Benjamin Saulnier,
  2. Stephanie Ponsart,
  3. Jean Coudane,
  4. Henry Garreau,
  5. Michel Vert*

Article first published online: 22 MAR 2004

DOI: 10.1002/mabi.200300087

Issue

Macromolecular Bioscience

Macromolecular Bioscience

Special Issue: Highlights from the First IUPAC International Conference on Bio-based Polymers (ICBP 2003) in Saitama, Japan

Volume 4, Issue 3, pages 232–237, March 15, 2004

Additional Information

How to Cite

Saulnier, B., Ponsart, S., Coudane, J., Garreau, H. and Vert, M. (2004), Lactic Acid-Based Functionalized Polymers via Copolymerization and Chemical Modification. Macromol. Biosci., 4: 232–237. doi: 10.1002/mabi.200300087

Author Information

  1. Research Centre for Artificial Biopolymers, 5473 CNRS Joint Unit, University Montpellier 1, Faculty of Pharmacy, 15 Ave. Ch. Flahault, BP 14491, F-34093 Montpellier Cedex 5, France

*Research Centre for Artificial Biopolymers, 5473 CNRS Joint Unit, University Montpellier 1, Faculty of Pharmacy, 15 Ave. Ch. Flahault, BP 14491, F-34093 Montpellier Cedex 5, France. Fax: +33 (0) 467 520898

Publication History

  1. Issue published online: 22 MAR 2004
  2. Article first published online: 22 MAR 2004
  3. Manuscript Accepted: 16 DEC 2003
  4. Manuscript Revised: 12 DEC 2003
  5. Manuscript Received: 4 NOV 2003

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Keywords:

  • copolymerization;
  • degradable polymers;
  • lactic acid;
  • modification

Abstract

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Summary: Poly(lactic acid) polymers (PLA) are presently the most attractive compounds in the field of artificial degradable and biodegradable polymers. In order to enlarge the family, and thus the range of accessible properties, stereocopolymers and copolymers with various co-monomers have been synthesized. However, very few are functionalized, i.e. include functional groups attached to the main chains or as part of the side chains. In the search for degradable PLA-type polymers bearing functional groups to serve as intermediates for further chemical modifications, we are exploring two different routes. The first one is copolymerization with a protected hydroxyl-bearing lactide-type monomer, namely 3-(1,2,3,4-tetraoxobutyldiisopropylidene)dioxane-2,5-dione. The second route consists of the formation of a carbanionic site in the α-position to intrachain carbonyl functions by using lithium N,N-diisopropylamide followed by the coupling of electrophiles. Recent advances in this search are presented using several examples. In particular, it is shown that OH-functionalized PLA-type macromolecules can be made fluorescent by chemical coupling. It is also shown that substituents can be attached to PLA-type macromolecules in solution or to the surface of PLA-based devices selectively.

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