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Vinylsulfide‐Containing Polyesters and Copolyesters from Fatty Acids: Thiol‐yne Monomer Synthesis and Thiol‐ene Functionalization
Author(s) -
Beyazkilic Zeynep,
Lligadas Gerard,
Ronda Juan Carlos,
Galià Marina,
Cádiz Virginia
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201400191
Subject(s) - polymer chemistry , copolymer , polyester , surface modification , condensation polymer , polymerization , thiol , monomer , chemistry , ene reaction , polymer , thermal stability , organic chemistry
The synthesis of a vinylsulfide‐containing hydroxy acid (VSHA) from undecylenic fatty acid via thiol‐yne monoaddition is described. Metal‐ and enzymatic‐catalyzed polycondensation of VSHA is investigated to obtain functional polyesters with a view to further modification. Higher molecular weights are obtained when using enzymatic polymerization. Random copolymers are prepared by direct enzymatic copolymerization of VSHA and ε‐caprolactone (CL) and triblock CL‐VSHA‐CL copolymers are obtained by consecutive VSHA self‐condensation and ring‐opening polymerization. The copolymers display semicrystalline behavior and a good thermal stability with no significant weight loss below 300 °C. Thiol‐ene chemistry‐type crosslinking and surface functionalization are employed to open new application fields. Evidence of the successful reactions is obtained by NMR, IR, and fluorescence measurements.