Lignosulfonate-based polyurethane materials via cyclic carbonates: preparation and characterization
-
Vebi Mimini
,
Robert Bischof
Abstract
Usage of lignin and its derivatives as chemical and carbon source, i.e. in processes other than burning, is one of the most active fields in renewable resource chemistry today. In this study, the synthesis of lignosulfonate (LS)-based polyurethane (PU) materials from non-toxic reagents and through environmentally friendly processes is presented. LS, modified with bio-based (glycerin-derived) cyclic carbonate moieties, was reacted with 1,6-hexamethylenediamine (HMDA) to form characteristic PU material. For mechanistic studies and reaction optimization, cyclic carbonates and 1,2-diol derivatives of vanillyl alcohol (VA), as a simplifying lignin model compound, were employed. An LS-bound cyclic carbonate can be formed in one pot without a transesterification step, which simplifies the route toward non-isocyanate lignin-based PU materials. Attenuated total reflection-Fourier transform infrared (ATR-FTIR) spectra showed typical linkages of cyclic carbonates and 1,2-diols on LS. Further analytical characterization, in both the model compound and the LS polymer case, was provided by liquid-state nuclear magnetic resonance (NMR) spectroscopy [one-dimensional (1D), two-dimensional (2D) and 31P] and 13C solid-state (ss) NMR. The production of PU materials from sulfonated lignin and glycerol carbonate, synthesized through a non-isocyanate reaction pathway, confirms the good potential of LS utilization in the development of PU composites based on renewable resources.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Financial support to WOOD Kplus was provided by the Austrian government, the provinces of lower Austria, upper Austria and Carinthia, as well as by Lenzing AG. We also express our gratitude to the University of Natural Resources and Life Sciences Vienna (BOKU Vienna), the Johannes Kepler University Linz and Lenzing AG for their in-kind contributions.
Employment or leadership: None declared.
Honorarium: None declared.
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Articles in the same Issue
- Frontmatter
- Editorial
- The 15th European Workshop on Lignocellulosics and Pulp (EWLP) in Aveiro, Portugal (June 26–29, 2018)
- Review
- Extractives and biological activities of Lamiaceae species growing in Uzbekistan
- Original Articles
- New drum-chipping technology for a more uniform size distribution of wood chips
- Characterization of enzyme-resistant xylooligosaccharides extracted from hardwood chips by pre-hydrolysis and further depolymerized by enzymatic treatment
- Stabilising mannose using sodium dithionite at alkaline conditions
- Xylan accessibility of bleached eucalypt pulp in alkaline solutions
- Investigation of eucalypt and pine wood acid-soluble lignin by Py-GC-MS
- The reaction of lignin model compounds during enzymatic bleaching with a Curvularia verruculosa haloperoxidase: impact on chlorination
- Molecular weight-based fractionation of lignin oils by membrane separation technology
- Phenol-formaldehyde resins with suitable bonding strength synthesized from “less-reactive” hardwood lignin fractions
- Impact of birch xylan composition and structure on film formation and properties
- Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol
- Lignosulfonate-based polyurethane materials via cyclic carbonates: preparation and characterization
- Bioconversion of pine stumps to ethanol: pretreatment and simultaneous saccharification and fermentation
- Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin
- Short Note
- Lignin analysis with benchtop NMR spectroscopy
Articles in the same Issue
- Frontmatter
- Editorial
- The 15th European Workshop on Lignocellulosics and Pulp (EWLP) in Aveiro, Portugal (June 26–29, 2018)
- Review
- Extractives and biological activities of Lamiaceae species growing in Uzbekistan
- Original Articles
- New drum-chipping technology for a more uniform size distribution of wood chips
- Characterization of enzyme-resistant xylooligosaccharides extracted from hardwood chips by pre-hydrolysis and further depolymerized by enzymatic treatment
- Stabilising mannose using sodium dithionite at alkaline conditions
- Xylan accessibility of bleached eucalypt pulp in alkaline solutions
- Investigation of eucalypt and pine wood acid-soluble lignin by Py-GC-MS
- The reaction of lignin model compounds during enzymatic bleaching with a Curvularia verruculosa haloperoxidase: impact on chlorination
- Molecular weight-based fractionation of lignin oils by membrane separation technology
- Phenol-formaldehyde resins with suitable bonding strength synthesized from “less-reactive” hardwood lignin fractions
- Impact of birch xylan composition and structure on film formation and properties
- Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol
- Lignosulfonate-based polyurethane materials via cyclic carbonates: preparation and characterization
- Bioconversion of pine stumps to ethanol: pretreatment and simultaneous saccharification and fermentation
- Selective recovery of polyphenols from MDF process waters by adsorption on a macroporous, cross-linked pyrrolidone-based resin
- Short Note
- Lignin analysis with benchtop NMR spectroscopy
