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Thiolated hemicellulose as a versatile platform for one-pot click-type hydrogel synthesis
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0001-5910-1226
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0002-1631-1781
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.
2015 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, no 2, 667-674 p.Article in journal (Refereed) Published
Abstract [en]

A one-pot synthetic methodology for the thiolation of O-acetyl-galactoglucomannan (AcGGM) was developed to merge hemicellulose chemistry with "click" chemistry. This was realized by the AcGGM-mediated nucleophilic ring-opening of γ-thiobutyrolactone via the activation of the polysaccharide pendant hydroxyl groups. The incorporation of thiol functionalities onto the hemicellulose backbone was visualized by 1H and 13C NMR spectroscopy and was assessed by an Ellman's reagent assay of the thiol groups. The versatility of the thiolated AcGGM was elaborated and demonstrated by conducting several postmodification reactions together with hydrogel formation utilizing thiol-ene and thiol-Michael addition "click" reactions. The one-pot synthesis of thiolated AcGGM is a straightforward approach that can expand the applications of hemicelluloses derived from biomass by employing "click" chemistry.

Place, publisher, year, edition, pages
2015. Vol. 16, no 2, 667-674 p.
Keyword [en]
Addition reactions, Hydrogels, Nuclear magnetic resonance spectroscopy, Galactoglucomannan, Hydrogel formation, Hydroxyl groups, Michael additions, Nucleophilic ring opening, One-pot synthesis, Post-modification, Synthetic methodology
National Category
Polymer Technologies
Identifiers
URN: urn:nbn:se:kth:diva-161070DOI: 10.1021/bm5018468ISI: 000349273000026Scopus ID: 2-s2.0-84922511118OAI: oai:DiVA.org:kth-161070DiVA: diva2:793604
Note

QC 20150309

Available from: 2015-03-09 Created: 2015-03-09 Last updated: 2017-12-04Bibliographically approved
In thesis
1. Chemical Pathways to Hemicellulose-rich Biomass Hydrogels
Open this publication in new window or tab >>Chemical Pathways to Hemicellulose-rich Biomass Hydrogels
2015 (English)Licentiate thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 52 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:12
National Category
Polymer Technologies
Identifiers
urn:nbn:se:kth:diva-161072 (URN)978-91-7595-452-3 (ISBN)
Presentation
2015-03-13, K2, Teknikringen 28, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20150309

Available from: 2015-03-09 Created: 2015-03-09 Last updated: 2015-03-09Bibliographically approved
2. Synthesis of AcGGM Polysaccharide Hydrogels
Open this publication in new window or tab >>Synthesis of AcGGM Polysaccharide Hydrogels
2016 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Lignocellulosic biomass is believed to serve a prominent role in tomorrow’s sustainable energy and material development. Among the polysaccharide fractions of lignocellulosic biomass, the potential of hemicelluloses as a valuable material resource is increasingly recognized. Thanks to their hydrophilic structure, hemicelluloses are suitable substrates for hydrogel design. The work summarized in this thesis aims to develop feasible strategies for the conversion of O-acetyl galactoglucomannan (AcGGM), an ample hemicellulose in softwood, into hydrogels. Within this framework, four synthetic pathways targeting the formation of crosslinked hydrogel networks from pure or unrefined AcGGM fractions were developed.

 

Aqueous AcGGM-rich and lignin-containing side-stream process liquors of forest industry, known as softwood hydrolysates (SWHs) were formulated into highly swellable hydrogels by: i) allyl-functionalization of AcGGM chains of crude SWH to obtain a viable precursor for hydrogel synthesis via free-radical crosslinking, ii) directly incorporating unmodified SWH fractions into semi-interpenetrating polymer networks (semi-IPNs). SWH hydrogels and semi-IPNs were characterized with appreciable maximum swelling ratios of Qeq = 170 and Qeq = 225, respectively.

 

Rapid crosslinking of AcGGM through thiol-click chemistry was addressed by first imparting thiol functionality onto pure AcGGM chains in a one-pot procedure. The thiolated AcGGM proved to be a suitable substrate for the synthesis of hemicellulose hydrogels via thiol-ene and thiol Michael addition reactions. Finally, sequential full IPNs were developed by subjecting single network hydrogels of pure AcGGM to a second network formation. IPNs obtained through either free radical crosslinking or thiol-ene crosslinking exhibited higher shear storage moduli than their single network counterparts. 

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2016. 69 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2016:37
Keyword
hemicellulose, O-acetyl-galactoglucomannan, wood hydrolysate, hydrogel, radical polymerization, interpenetrating polymer network, click chemistry, thiol-ene, Michael addition
National Category
Polymer Technologies Polymer Chemistry
Research subject
Fibre and Polymer Science
Identifiers
urn:nbn:se:kth:diva-195091 (URN)978-91-7729-155-8 (ISBN)
Public defence
2016-12-16, Kollegiesalen, Brinellvägen 8, KTH-campus, Stockholm, 10:30 (English)
Opponent
Supervisors
Note

QC 20161102

Available from: 2016-11-02 Created: 2016-11-01 Last updated: 2016-12-16Bibliographically approved

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Maleki, LalehEdlund, Ulrica

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