Issue 16, 2021

Polyamides containing a biorenewable aromatic monomer based on coumalate esters: from synthesis to evaluation of the thermal and mechanical properties

Abstract

A new biobased alternative for terephthalic acid (TPA) in (semi-)aromatic polyamides is proposed, namely 4-carboxybenzene propionic acid (4CBPA). The difference between both monomers is the additional ethylene segment in 4CBPA, which is therefore an asymmetrical monomer. Because of this, differences in the thermal and mechanical properties between 4CBPA and TPA based polyamides are expected. Herein, thermal stability of a 4CBPA model compound was evaluated, and the reactivity difference between the two carboxylic acids of 4CBPA was observed in model reactions. 4CBPA was polymerized with several aromatic and (cyclo)aliphatic diamines via different synthesis methods. Depending on the amine that was used, a different synthesis method is preferred. From a green chemistry point of view, catalyzed melt condensation is the most preferred. The best polymers were further characterized by NMR spectroscopy, IR spectroscopy, TGA, DSC and MALDI-ToF-MS. Additional evaluation of the synthesized 4CBPA polyamides allowed comparison with TPA equivalents. It was found that 4CBPA polyamides with m-xylylenediamine (MXD) and hexamethylenediamine possessed lowered Tg and Tm compared to their TPA equivalents. In case of 4CBPA polyamides with MXD, crystallinity disappears completely. Finally, the tensile properties of one of the 4CBPA polyamides were evaluated in polyamide 12 blends.

Graphical abstract: Polyamides containing a biorenewable aromatic monomer based on coumalate esters: from synthesis to evaluation of the thermal and mechanical properties

Supplementary files

Article information

Article type
Paper
Submitted
02 Janv. 2021
Accepted
23 Marts 2021
First published
23 Marts 2021

Polym. Chem., 2021,12, 2379-2388

Polyamides containing a biorenewable aromatic monomer based on coumalate esters: from synthesis to evaluation of the thermal and mechanical properties

J. Stouten, A. A. Wróblewska, G. Grit, J. Noordijk, B. Gebben, M. H. M. Meeusen-Wierts and K. V. Bernaerts, Polym. Chem., 2021, 12, 2379 DOI: 10.1039/D1PY00005E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements