Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins
The functionalisation of lignin-derived phenolics (guaiacol, 4-propylguaiacol, eugenol, isoeugenol, phenol, <i>m</i>-cresol, catechol, syringol, syringaldehyde, and vanillin) for the synthesis of thermoplastic polyurethanes (PUs) and polyester (PE) resins is herein described. Diols were...
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2025-06-01
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| author | Rachele N. Carafa Justin J. S. Kosalka Brigida V. Fernandes Unnati Desai Daniel A. Foucher Guerino G. Sacripante |
| author_facet | Rachele N. Carafa Justin J. S. Kosalka Brigida V. Fernandes Unnati Desai Daniel A. Foucher Guerino G. Sacripante |
| author_sort | Rachele N. Carafa |
| collection | DOAJ |
| description | The functionalisation of lignin-derived phenolics (guaiacol, 4-propylguaiacol, eugenol, isoeugenol, phenol, <i>m</i>-cresol, catechol, syringol, syringaldehyde, and vanillin) for the synthesis of thermoplastic polyurethanes (PUs) and polyester (PE) resins is herein described. Diols were synthesised from phenolics in a one-step reaction using either glycerol carbonate or ethylene carbonate as a greener, solvent-free synthetic route. Nine of the diols were selected for the synthesis of Pus, and two of the diols were used for the synthesis of PE resins, with their physical and thermal properties characterised. Analysis of the PUs by differential scanning calorimetry (DSC) confirmed their amorphous nature, while thermogravimetric analysis (TGA) suggested improved thermal stability for all PUs with the addition of an alkyl or aldehyde substituent on the benzene ring regardless of the diisocyanate used. However, lower PU thermal stabilities were observed with the use of an aliphatic diisocyanate over an aromatic diisocyanate in the absence of an additional substituent. Analysis of the PEs by DSC also confirmed that the clear resins were all amorphous, and gel permeation chromatography (GPC) revealed significantly higher molecular weights and dispersities when an aliphatic diacid was utilised over an aromatic diacid. |
| format | Article |
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| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-be6dcbc123274f82a8f25672b76e9a902025-08-20T03:27:39ZengMDPI AGMolecules1420-30492025-06-013012260410.3390/molecules30122604Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester ResinsRachele N. Carafa0Justin J. S. Kosalka1Brigida V. Fernandes2Unnati Desai3Daniel A. Foucher4Guerino G. Sacripante5Department of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaDepartment of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaDepartment of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaDepartment of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaDepartment of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaDepartment of Chemistry and Biology, Toronto Metropolitan University, 350 Victoria Street, Toronto, ON M5B 2K3, CanadaThe functionalisation of lignin-derived phenolics (guaiacol, 4-propylguaiacol, eugenol, isoeugenol, phenol, <i>m</i>-cresol, catechol, syringol, syringaldehyde, and vanillin) for the synthesis of thermoplastic polyurethanes (PUs) and polyester (PE) resins is herein described. Diols were synthesised from phenolics in a one-step reaction using either glycerol carbonate or ethylene carbonate as a greener, solvent-free synthetic route. Nine of the diols were selected for the synthesis of Pus, and two of the diols were used for the synthesis of PE resins, with their physical and thermal properties characterised. Analysis of the PUs by differential scanning calorimetry (DSC) confirmed their amorphous nature, while thermogravimetric analysis (TGA) suggested improved thermal stability for all PUs with the addition of an alkyl or aldehyde substituent on the benzene ring regardless of the diisocyanate used. However, lower PU thermal stabilities were observed with the use of an aliphatic diisocyanate over an aromatic diisocyanate in the absence of an additional substituent. Analysis of the PEs by DSC also confirmed that the clear resins were all amorphous, and gel permeation chromatography (GPC) revealed significantly higher molecular weights and dispersities when an aliphatic diacid was utilised over an aromatic diacid.https://www.mdpi.com/1420-3049/30/12/2604ligninbiobasedphenolsglycerol carbonateethylene carbonatepolyurethanes |
| spellingShingle | Rachele N. Carafa Justin J. S. Kosalka Brigida V. Fernandes Unnati Desai Daniel A. Foucher Guerino G. Sacripante Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins Molecules lignin biobased phenols glycerol carbonate ethylene carbonate polyurethanes |
| title | Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins |
| title_full | Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins |
| title_fullStr | Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins |
| title_full_unstemmed | Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins |
| title_short | Functionalisation of Lignin-Derived Diols for the Synthesis of Thermoplastic Polyurethanes and Polyester Resins |
| title_sort | functionalisation of lignin derived diols for the synthesis of thermoplastic polyurethanes and polyester resins |
| topic | lignin biobased phenols glycerol carbonate ethylene carbonate polyurethanes |
| url | https://www.mdpi.com/1420-3049/30/12/2604 |
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