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A Novel Approach for the Synthesis of Thermo‐Responsive Co‐Polyesters Incorporating Reversible Diels–Alder Adducts
Author(s) -
Banella Maria Barbara,
Giacobazzi Greta,
Vannini Micaela,
Marchese Paola,
Colonna Martino,
Celli Annamaria,
Gandini Alessandro,
Gioia Claudio
Publication year - 2019
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.201900247
Subject(s) - polyester , maleimide , copolyester , copolymer , adduct , condensation polymer , polymer chemistry , depolymerization , phthalic anhydride , diels–alder reaction , chemistry , materials science , monomer , organic chemistry , polymer , catalysis
The proof of concept for a new copolymerization approach taking advantage of the thermally reversible aptitude of the furan/maleimide Diels–Alder (DA) adducts is reported here. A new monomer bearing two carboxylic acids as end‐groups and a Diels–Alder adduct within its structure is synthesized using benign and mild reaction conditions. Two polyesters are then fabricated from the DA‐diacid and 1,6‐hexanediol and 1,4‐benzenedimethanol, respectively, and characterized by 1 H‐NMR, GPC, DSC, and TGA. Kinetic studies of these polyesters, performed by 1 H‐NMR spectroscopy at variable temperatures, establish the appropriate conditions for their controlled depolymerization, through the retro Diels–Alder reaction (rDA), and their re‐construction through the DA reaction, showing moreover the reproducibility of this rDA/DA cycle. Finally, by exploiting this peculiar feature, a copolyester is successfully synthesized from the concomitant treatment of the two homopolymers, demonstrating the effectiveness of the method. The present approach provides a new method for the fabrication of multicomponent copolymers based on the DA/rDA strategy that is extendable to a variety of other polycondensation materials, such as polyesters, polyamides, polyurethanes, and epoxies, allowing the establishment of a library of novel architectures through this one‐pot approach.