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Alkenyl-Functionalized Precursors for Renewable Hydrogels Design
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0002-1631-1781
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
2009 (English)In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 47, no 14, 3595-3606 p.Article in journal (Refereed) Published
Abstract [en]

A library of crosslinking chemistries for the hydrogel synthesis based on the hemicellulose acetylated galactoglucomannan (AcGGM) has been developed, demonstrated, and evaluated. A three-step route was elaborated including (1) the carbonyldiimidazole activation of primary hydroxylated vinylic molecules such as acrylates, vinyl alcohols, and vinyl ethers, (2) the covalent coupling of the alkenyl precursors to the polysaccharide backbone hydroxyls, and (3) the radical crosslinking of pendant vinyl functionalities affording a hydrophilic network. Crosslinking strategies explored include redox initiation and photo initiation, with an effort to adapt the suggested synthesis routes to benign conditions. The different functionalization strategies were shown to influence the resulting gel's properties. Varying the crosslinking media was found to be a strong tool to tune the properties of the gels. Modifications were in all cases verified by means of NMR and FTIR, and the gels were characterized with respect to swelling capacity and rheological parameters. It was shown that by adjusting the synthesis parameters, the resulting properties of the AcGGM gels could be custom-made for a given performance.

Place, publisher, year, edition, pages
2009. Vol. 47, no 14, 3595-3606 p.
Keyword [en]
crosslinking, galactoglucomannan, hemicellulose, hydrogels, polysaccharides, swelling, hemicellulose-based hydrogels, biodegradable polymers, delivery, softwood, water
National Category
Other Materials Engineering
Identifiers
URN: urn:nbn:se:kth:diva-18552DOI: 10.1002/pola.23444ISI: 000267444200011Scopus ID: 2-s2.0-67650669939OAI: oai:DiVA.org:kth-18552DiVA: diva2:336599
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Functional and Renewable Galactoglucomannan-based Hydrogels
Open this publication in new window or tab >>Functional and Renewable Galactoglucomannan-based Hydrogels
2009 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

Polysaccharides represent an important resource for a variety of products, from food via fuel supply to functional materials of every kind. Here they are, due to their natural diversity found in many special applications, e.g. in the biomedical sector.

Lately, a fairly unused group of polysaccharides, so called hemicelluloses, attracts more and more attention due to its high availability and promising properties.

This thesis presents the utilization of the water-soluble species O-acetyl-galactoglucomannan (AcGGM),   derived from softwood, as raw material for the synthetic design of functional hydrogels. AcGGM was used thanks to its great availability and high hydrophilicity rendering it an excellent material for hydrogels design.

For this purpose, a three-step-method was devised consisting of (1) the carbonyldiimidazole activation of primary hydroxylated vinylic compounds, (2) the substitution of hydroxyl groups of the AcGGM backbone with vinylic functions, and (3) radical crosslinking yielding in a hydrophilic three-dimensional network – a hydrogel.

Crosslinking strategies were varied from photo-crosslinking in DMSO to redox-initiated crosslinking in H2O with the objective of adapting the synthesis to benign conditions. Varying the crosslinking-species as well as the media was found to have a significant influence on the resulting gels’ properties, such as swelling capacity and G-modulus.  Here, swelling capacity could be affected to vary between ~0.6 to ~23 times of the gels self-weight and the G-modulus ranged from 0.4 to 145 kPa.

AcGGM and 2-hydroxy ethyl methacrylate (HEMA) gels were studied further and evaluated for their suitability as drug delivery systems for two model drugs (caffeine and Vitasyn Blue) varying in size, polarity and hydrophilicity. Here, the gels’ composition as well as a second modification with maleic acid anhydride was proved to affect the release properties significantly.

Based on our findings we conclude that the presented library is an important step to the promising future of these hydrogels based on the renewable resource AcGGM.

Place, publisher, year, edition, pages
Stockholm: Fiber- och polymerteknologi, 2009. iii, 48 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:22
Keyword
Polysaccharides, hydrogels, swelling, crosslinking, hemicellulose, release, polysackarider, hemicellulosa, hydrogel, läkemedelsfrisättning, förnyelsebar, tvärbindning.
National Category
Other Materials Engineering
Identifiers
urn:nbn:se:kth:diva-10474 (URN)978-91-7415-350-7 (ISBN)
Presentation
2009-05-10, K1, KTH, Teknikringen 56, Stockholm, 10:00 (English)
Opponent
Supervisors
Projects
Gröna MaterialPulp Mill Biorefinery
Available from: 2009-05-26 Created: 2009-05-18 Last updated: 2010-11-03Bibliographically approved
2. Chemical Pathways for Galactoglucomannan-based Materials
Open this publication in new window or tab >>Chemical Pathways for Galactoglucomannan-based Materials
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Polysaccharides are an important resource for a variety of products, from food via fuel supply to functional materials of every kind. Due to their natural diversity they can be found in many special applications, e.g. in the biomedical sector and are the major renewable resource for materials of many kinds.

Recently, a fairly unused group of polysaccharides, so called

hemicelluloses, have attracted increasing attention due to their high availability and promising properties in combination with renewability and a potentially low price.

This thesis presents pathways for the chemical modification of the water-soluble hemicellulose

acetylated galactoglucomannan (AcGGM), enabling this raw material to be utilized in the synthetic design of new classes of materials.

Based on the chemical modification of the hydroxyl groups with crosslinkable groups in combination with the naturally high hydrophilicity, synthetic pathways for the production of functional hydrogels are presented. Thanks to the great availability and the native properties of AcGGM, this material was found to be an outstanding candidate in this respect and was adjudged to be a cheap and green resource for hydrogel design.

For this purpose, a three-step method was devised consisting of (1) the carbonyldiimidazole activation of primary hydroxylated vinylic compounds, (2) the substitution of hydroxyl groups of the AcGGM backbone with vinylic functions, and (3) radical crosslinking yielding a hydrophilic three-dimensional network – a hydrogel.

Crosslinking strategies were varied from photo-crosslinking in dimethyl sulfoxide (DMSO) to redox-initiated crosslinking in H

2O, with the objective of adapting the synthesis to benign conditions. Varying the crosslinking species as well as the medium was found to have a significant influence on the resulting gels’ properties, such as swelling capacity and G-modulus. Swelling capacity could be varied between ~0.6 and ~23 times the gel’s own weight and the G-modulus ranged from 0.4 to 145 kPa.

AcGGM and 2-hydroxy ethyl methacrylate (HEMA) gels were studied further and evaluated for their suitability as drug delivery systems for two model drugs (caffeine and Vitasyn Blue) varying size, polarity, and hydrophilicity of the drug to be II

released. It was found that the gels composition as well as a second modification with maleic acid anhydride affects the release properties.

Taking well-studied polysaccharide modification chemistry one step further and combining it with state of the art polymer synthesis, graft-copolymers of AcGGM were successfully synthesized via single-electron-transfer living-radical polymerization (SET-LRP). For this purpose, a macroinitiator was derived from AcGGM to enable a grafting of diverse hydrophilic and hydrophobic monomers from the AcGGM under benign conditions. Hybrid materials of the natural polymer AcGGM as a backbone with synthetic poly(methyl acrylate), poly(methyl methacrylate), poly(acrylamide), and poly(N-isopropyl acrylamide) graft-copolymers with a brush-like architecture were successfully synthesized, yielding molecular weights of up to 240∙10³ g ∙ mol

-1. As expected, the solubility and thermal properties were significantly altered, opening a wider range of potential applications.

We conclude that the presented chemical pathways are important steps towards a promising future for hemicelluloses as raw materials and their derivatives as shown for the resource AcGGM.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. viii, 76 p.
Series
Trita-CHE-Report, ISSN 1654-1081
Keyword
Polysaccharides, hemicelluloses, galactoglucomannan, renewable, chemical modification, hydrogels, swelling, crosslinking, release, SET-LRP, living polymerization, grafting, hybrid materials
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-34007 (URN)978-91-7415-989-9 (ISBN)
Public defence
2011-06-14, F3, Lindstedtsvägen 26, KTH, Stockholm, 09:00 (English)
Opponent
Supervisors
Note
QC 20110530Available from: 2011-05-30 Created: 2011-05-23 Last updated: 2011-05-30Bibliographically approved

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