Synthesis, kinetics, and characterization of bio-based thermosets obtained through polymerization of a 2,5-furandicarboxylic acid-based bis(2-oxazoline) with sebacic acid

Carolus H. R. M. Wilsens, Nino J. M. Wullems, Erik Gubbels, Yefen Yao, Sanjay Rastogi, Bart A. J. Noordover*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Web of Science)

Abstract

The synthesis of renewable 2,5-furandicarboxylic acid-based cross-linked poly(ester amide)s via the polymerization of a 2,5-furandicarboxylic acid based bis(2-oxazoline) monomer (2,5-bis(4,5-dihydrooxazol- 2-yl) furan, 2,5-FDCAox) with sebacic acid is reported in this work. It is demonstrated that the amide groups in the 2,5-furandicarboxamide moiety are susceptible to participation in a branching reaction with 2-oxazoline rings. The corresponding enhanced reaction rate decreases the curing times for the preparation of cross-linked polymers compared to systems containing the isophthalic acid based alternative, 1,3-bis(4,5-dihydrooxazol-2-yl) benzene (IAox). The increased tendency to form branches or cross-links in 2,5-FDCAox based systems is attributed to the occurrence of intra-molecular hydrogen bonding of the 2,5-furandicarboxamide moiety. Such an intra-molecular hydrogen bond increases the nucleophilicity of the furanic amide group and makes it more susceptible to participation in an addition reaction with a 2-oxazoline ring. Furthermore, it is demonstrated that the rate of the branching reaction can be enhanced by the addition of triphenyl phosphite as catalyst, resulting in a further decrease of the curing times of the poly(ester amide) s synthesized in this study. Preliminary coating studies indicate that 2,5-furandicarboxylic acid based crosslinked poly(ester amide) s synthesized via the 2-oxazoline ring opening addition reactions with dicarboxylic acids are good candidates for the development of fully renewable cross-linked poly(ester amide)s.
Original languageEnglish
Pages (from-to)2707-2716
JournalPolymer Chemistry
Volume6
Issue number14
DOIs
Publication statusPublished - 2015

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