Enzymatic Polymerization of Furan-2,5-Dicarboxylic Acid-Based Furanic-Aliphatic Polyamides as Sustainable Alternatives to Polyphthalamides

Furan-2,5-dicarboxylic acid (FDCA)-based furanic-aliphatic polyamides can be used as promising sustainable alternatives to polyphthalamides (semiaromatic polyamides) and be applied as high performance materials with great commercial interest. In this study, poly(octamethylene furanamide) (PA8F), an...

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Bibliographic Details
Published in:Biomacromolecules
Main Authors: Jiang, Yi, Maniar, Dina, Woortman, Albert J. J., van Ekenstein, Gert O. R. Alberda, Loos, Katja
Format: Article in Journal/Newspaper
Language:English
Published: 2015
Subjects:
RING-OPENING POLYMERIZATION
HIGH-PERFORMANCE POLYMERS
ANTARCTICA LIPASE-B
RENEWABLE RESOURCES
EPSILON-CAPROLACTONE
CATALYZED SYNTHESIS
IONIC LIQUIDS
BETA-LACTAM
POLYESTERS
SOLVENT
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11370/f39f31df-e49c-46ae-85f3-46f00de95792
https://research.rug.nl/en/publications/f39f31df-e49c-46ae-85f3-46f00de95792
https://doi.org/10.1021/acs.biomac.5b01172
https://pure.rug.nl/ws/files/83661767/Enzymatic_Polymerization_of_Furan_2_5_Dicarboxylic_Acid_Based_Furanic_Aliphatic.pdf
Description
Summary:Furan-2,5-dicarboxylic acid (FDCA)-based furanic-aliphatic polyamides can be used as promising sustainable alternatives to polyphthalamides (semiaromatic polyamides) and be applied as high performance materials with great commercial interest. In this study, poly(octamethylene furanamide) (PA8F), an analog to poly(octamethylene terephthalamide) (PA8T), is successfully produced via Novozym 435 (N435)-catalyzed polymerization, using a one-stage method in toluene and a temperature-varied two-stage method in diphenyl ether, respectively. The enzymatic polymerization results in PA8F with high weight-average molecular weight ((M-w) over bar) up to 54000 g/mol. Studies on the one-stage enzymatic polymerization in toluene indicate that the molecular weights of PA8F increase significantly with the concentration of N435; with an optimal reaction temperature of 90 degrees C. The temperature-varied, two-stage enzymatic polymerization in diphenyl ether yields PA8F with higher molecular weights, as compared to the one-stage procedure, at higher reaction temperatures. MALDI-ToF MS analysis suggests that eight end groups are present in the obtained PA8F: ester/amine, ester/ester, amine/amine, acid/amine, ester/acid, acid/acid, ester/amide, and no end groups (cyclic). Compared to PA8T, the obtained PA8F possesses a similar T-g and similar crystal structures, a comparable T-d, but a lower T-m.

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