Thermoreversible Diels–Alder Cross-Linking of BHMF-Based Polyesters: Synthesis, Characterization and Rheology

IF 7.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Cornelis Post, Paul van den Tempel, Paula Herrera Sánchez, Dina Maniar, Ranjita K. Bose, Vincent S. D. Voet, Rudy Folkersma, Francesco Picchioni, Katja Loos
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引用次数: 0

Abstract

2,5-Bis(hydroxymethyl)furan (BHMF)-based polyesters are an interesting new class of biobased and potentially biodegradable furanic polymers. However, their thermal properties are currently insufficient, making them unsuitable for potential applications as commodity plastics. To improve this, several polyesters were synthesized using an enzymatic bulk polymerization process with the monomers BHMF and aliphatic dimethyl esters of varying spacer lengths. The BHMF units were subsequently cross-linked with a biobased bismaleimide (BM-689) through a [4 + 2] cycloaddition reaction between the furan and maleimide groups. This approach clearly demonstrated that these furan-based polyesters can be thermoreversibly cross-linked using this bismaleimide. The use of different spacer lengths further allows the variation in relative reaction rates and affects the reversibility and reprocessability of the polymers. In situ 1H NMR spectroscopy revealed the identification of the endo- and exostereoadducts formed by the Diels–Alder reaction. A rheological analysis demonstrated the reprocessability and the thermal properties were further characterized via thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). This study sheds light on the thermal and mechanical enhancement of biobased BHMF-based polyesters, while maintaining their recyclability, which widens the range of potential application of this promising polymer.

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来源期刊
ACS Sustainable Chemistry & Engineering
ACS Sustainable Chemistry & Engineering CHEMISTRY, MULTIDISCIPLINARY-ENGINEERING, CHEMICAL
CiteScore
13.80
自引率
4.80%
发文量
1470
审稿时长
1.7 months
期刊介绍: ACS Sustainable Chemistry & Engineering is a prestigious weekly peer-reviewed scientific journal published by the American Chemical Society. Dedicated to advancing the principles of green chemistry and green engineering, it covers a wide array of research topics including green chemistry, green engineering, biomass, alternative energy, and life cycle assessment. The journal welcomes submissions in various formats, including Letters, Articles, Features, and Perspectives (Reviews), that address the challenges of sustainability in the chemical enterprise and contribute to the advancement of sustainable practices. Join us in shaping the future of sustainable chemistry and engineering.
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