Reversibly Crosslinked Polyurethane Fibres from Sugar-Based 5-Chloromethylfurfural: Synthesis, Fibre-Spinning and Fibre-to-Fibre Recycling

Niklas Warlin; Maria Nelly Garcia Gonzalez; Rafael N L de Menezes; Andras Karajos; Emma Olsson; Caroline Almqvist; Mahmoud Sayed; Smita V Mankar; Nitin G Valsange; Omar Y Abdelaziz; Christian P Hulteberg; Fredrik G Bäcklund; Zengwei Guo; Nicola Rehnberg; Stefan Lundmark; Rajni Hatti-Kaul; Patric Jannasch; Baozhong Zhang

doi:10.1002/cssc.202402067

Reversibly Crosslinked Polyurethane Fibres from Sugar-Based 5-Chloromethylfurfural: Synthesis, Fibre-Spinning and Fibre-to-Fibre Recycling

ChemSusChem. 2024 Oct 1:e202402067. doi: 10.1002/cssc.202402067. Online ahead of print.

Authors

Niklas Warlin^{1

2}, Maria Nelly Garcia Gonzalez³, Rafael N L de Menezes¹, Andras Karajos¹, Emma Olsson¹, Caroline Almqvist¹, Mahmoud Sayed⁴, Smita V Mankar¹, Nitin G Valsange¹, Omar Y Abdelaziz^{5

6}, Christian P Hulteberg⁷, Fredrik G Bäcklund⁸, Zengwei Guo⁸, Nicola Rehnberg^{1

9}, Stefan Lundmark¹⁰, Rajni Hatti-Kaul⁴, Patric Jannasch¹, Baozhong Zhang¹

Affiliations

¹ Department of Chemistry, Centre for Analysis and Synthesis, Lund University, SE-221 00, Lund, Sweden.
² Department of Chemistry, Stanford University, Stanford, 94305-5080, California, United States.
³ Environmental and Energy Systems Studies, Department of Technology and Society, Lund University, SE-221 00, Lund, Sweden.
⁴ Division of Biotechnology, Department of Chemistry, Lund University, SE-221 00, Lund, Sweden.
⁵ Department of Chemical Engineering, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia.
⁶ Interdisciplinary Research Center for Refining & Advanced Chemicals, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia.
⁷ Division of Chemical Engineering, Department of Process and Life Science Engineering, Lund University, SE-221 00, Lund, Sweden.
⁸ Division Materials and Production, Department of Polymers Fibers and Composites, RISE Research Institutes of Sweden, SE-43153, Mölndal, Sweden.
⁹ Bona Sweden AB, SE-200 21, Malmö, Sweden.
¹⁰ Perstorp AB, Perstorp Industrial Park, SE-284 80, Perstorp, Sweden.

PMID: 39352793
DOI: 10.1002/cssc.202402067

Abstract

The development of recyclable crosslinked thermosetting fibres is a challenging research topic. In the present work, we have designed and synthesized polyurethane fibres from fructose-derived 5-chloromethylfurfural (CMF) and lignin-derived monomeric phenols. The greenhouse gas emissions associated with the production of CMF showed comparable results to that of 5-hydroxymethylfurfural (HMF), a high potential sugar-based platform molecule. The wet-spun biobased polyurethane fibres produced could be conveniently crosslinked using Diels-Alder chemistry to effectively enhance the glass transition temperature and mechanical properties. At a mildly elevated temperature (140 °C), the chemically crosslinked fibres could be effectively de-crosslinked, which enabled complete separation from a mixture with poly(ethylene terephthalate) (PET) and cotton fibres. These results outline a potential strategy to design and fabricate new biobased fibres with reversible crosslinking, which may enable fibre-to-fibre recycling.

Keywords: Bio-based molecules; Chemical recycling; Fibre spinning; Life cycle assessment; Polyurethane.

Abstract

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