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Preparation of Clickable Poly(3‐hydroxyalkanoate) (PHA): Application to Poly(ethylene glycol) (PEG) Graft Copolymers Synthesis
Author(s) -
Babinot Julien,
Renard Estelle,
Langlois Valérie
Publication year - 2010
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200900803
Subject(s) - ethylene glycol , copolymer , amphiphile , side chain , peg ratio , polymer chemistry , propargyl alcohol , grafting , propargyl , click chemistry , reactivity (psychology) , chemistry , materials science , organic chemistry , catalysis , polymer , medicine , alternative medicine , finance , pathology , economics
A new synthesis of amphiphilic biodegradable copolymers consisting of hydrophobic poly(3‐hydroxyalkanoate) (PHA) backbone and hydrophilic poly(ethylene glycol) (PEG) units as side chains is described. Poly[(3‐hydroxyoctanoate)‐ co ‐(3‐hydroxyundecenoate)] (PHOU) was first methanolyzed and its unsaturated side chains were quantitatively oxidized to carboxylic acid. Esterification with propargyl alcohol led to an alkyne‐containing “clickable” PHA in 71% conversion. Its reactivity was successfully demonstrated by grafting azide‐terminated PEG chains of 550 and 5 000 g · mol −1 , respectively. All products were fully characterized using GPC, 1 H, and COSY NMR.