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Synthesis and Ring Opening Polymerization of a New Functional Lactone, α ‐Iodo‐ ε ‐caprolactone: A Novel Route to Functionalized Aliphatic Polyesters
Author(s) -
Habnouni Sarah El,
Darcos Vincent,
Coudane Jean
Publication year - 2009
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.200800596
Subject(s) - ring opening polymerization , caprolactone , lithium diisopropylamide , polymer chemistry , polyester , polymerization , monomer , chemistry , lactone , nucleophile , molar mass distribution , electrophile , anionic addition polymerization , catalysis , materials science , organic chemistry , polymer , ion , deprotonation
A new functional lactone, α ‐iodo‐ ε ‐caprolactone ( α I ε CL), was synthesized from ε ‐caprolactone by anionic activation using a non‐nucleophilic strong base (lithium diisopropylamide) followed by an electrophilic substitution with iodine chloride. Ring‐opening (co)polymerizations of the resulting monomer with ε ‐caprolactone were carried out using tin 2‐ethylhexanoate as a catalyst in toluene at 100 °C. Homopolymerization of α I ε CL was achieved, and poly( α I ε CL) was fully characterized by SEC, 1 H NMR and elemental analysis. Random copolymerizations of α I ε CL with ε CL were controlled with experimental molecular weights close to the theoretical values, narrow molecular weight distributions and a good agreement between experimental and theoretical molar compositions of α I ε CL.