Synthesis and characterisation of polyamides based on 2,5-furandicarboxylic acid as a sustainable building block for engineering plastics†

Muhammad Kamran, Matthew Davidson, Sicco de Vos, Vasilios Tsanaktsis, Bahar Yeniad

Research output: Contribution to journalArticlepeer-review

7 Citations (SciVal)

Abstract

Polyphthalamides (PPAs) are promising engineering thermoplastics employed in several demanding applications. At present, most of the commercially available PPAs are based on non-renewable petroleum derived resources. Herein, we investigated the synthesis of a semi-aromatic polyamide, poly(hexamethylene furanamide) (PA6F), based on a bio-based monomer, 2,5-furandicarboxylic acid (FDCA), using melt polycondesation in the presence of two catalysts: Ti-isopropoxide (TIPT) and Ti-citrate (TIC). Initial experimentation and optimisation conducted in a thin-film reactor led to PA6F having number-average molecular weight (Mn) of 14 000 g mol−1 at very low catalyst loading (400 ppm TIPT). The reaction was scaled-up to further assess the catalytic activity of these catalysts. Both catalysts displayed strong selectivity for the ester amidation reaction compared to the uncatalysed system, resulting in PA6Fs with improved molecular weights and glass transition temperatures. Incorporating a slight excess (4.5 mol%) of hexamethylenediamine (HMDA) in the feed, resulted in further enhancement in the glass transition temperature; an increase of up to 10 °C was observed. The polymer structure and properties were extensively investigated with the help of a range of analytical techniques. The resultant polymer showed high glass transition temperature (130 °C) and elastic modulus (3.5 GPa), and comparable thermal stability to its structural analogue poly(hexamethylene terephthalamide) (PA6T). For the uncatalysed system, MALDI-ToF mass spectrometry revealed a series of methylated chain ends at both oligomerisation and polycondensation steps, inhibiting molecular weight growth.
Original languageEnglish
Pages (from-to)3433-3443
Number of pages11
JournalPolymer Chemistry
Volume13
Issue number23
Early online date16 May 2022
DOIs
Publication statusPublished - 21 Jun 2022

Bibliographical note

This project has received funding from the European Union's Horizon 2020 Research and Innovation Programme under the Marie Skłodowska-Curie grant agreement no. 665992 and from Corbion Biochem B.V. (PhD studentship for MK). UK Catalysis Hub is kindly thanked for resources and support provided via our membership of the UK Catalysis Hub Consortium and funded by EPSRC grant EP/R027129/1. The authors gratefully acknowledge the contributions of Taco Visser, Jessica Kraak and Stefan van Berkel from Corbion for their assistance in GPC analysis and for their helpful discussions.

ASJC Scopus subject areas

  • Bioengineering
  • Biochemistry
  • Polymers and Plastics
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and characterisation of polyamides based on 2,5-furandicarboxylic acid as a sustainable building block for engineering plastics†'. Together they form a unique fingerprint.

Cite this