Lactic Acid-Based Functionalized Polymers via Copolymerization and Chemical Modification

✍ Scribed by Benjamin Saulnier; Stephanie Ponsart; Jean Coudane; Henry Garreau; Michel Vert

• Book ID: 102466888
• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 136 KB
• Volume: 4
• Category: Article
• ISSN: 1616-5187
• DOI: 10.1002/mabi.200300087

✦ Synopsis

Abstract

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.

Example of chemical modifications of hydroxyl‐bearing PLA‐type polymers derived from gluconic and glycolic acids (via gluconolactone) and lactic acid (via lactide).

imageExample of chemical modifications of hydroxyl‐bearing PLA‐type polymers derived from gluconic and glycolic acids (via gluconolactone) and lactic acid (via lactide).