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Dendronized Hydroxypropyl Cellulose: Synthesis and Characterization of Biobased Nanoobjects
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
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: 0000-0002-8348-2273
2007 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 8, no 12, 3815-3822 p.Article in journal (Refereed) Published
Abstract [en]

Dendronized polymers containing a cellulose backbone have been synthesized with the aim of producing complex molecules with versatile functionalization possibilites and high molecular weight from biobased starting materials. The dendronized polymers were built by attaching premade acetonide-protected 2,2-bis(methylol)propionic acid functional dendrons of generation one to three to a hydroxypropyl cellulose backbone. Deprotection or functionalization of the end groups of the first generation dendronized polymer to hydroxyl groups and long alkyl chains was performed, respectively. The chemical structures of the dendronized polymers were confirmed through analysis using H-1 NMR and FT-IR spectroscopies. From SEC analysis, the dendronized polymers were found to have an increasing polystyrene-equivalent molecular weight up to the second generation (M-n = 50 kg mol(-1)), whereas the polystyrene-equivalent molecular weight for the third generation was lower than for the second, although the same grafting density was obtained from H-1 NMR spectroscopy for the second and third generations. Tapping-mode atomic force microscopy was used to characterize the properties of the dendronized polymers in the dry state, exploring both the effect of the polar substrate mica and the less polar substrate highly oriented pyrolytic graphite (HOPG). It was found that the molecules were in the size range of tens of nanometers and that they were apt to undertake a more elongated conformation on the HOPG surfaces when long alkyl chains were attached as the dendron end-groups.

Place, publisher, year, edition, pages
2007. Vol. 8, no 12, 3815-3822 p.
Keyword [en]
Characterization; Molecular weight; Molecules; Structure (composition); Synthesis (chemical); Cellulose backbone; Dendronized polymers; Nanoobjects; alkyl group; graphite; hydroxyl group; hydroxypropylcellulose; nanoparticle; polystyrene; propionic acid derivative; article; atomic force microscopy; carbon nuclear magnetic resonance; chemical modification; chemical structure; complex formation; conformational transition; controlled study; dendronization; gel permeation chromatography; infrared spectroscopy; molecular weight; priority journal; proton nuclear magnetic resonance; synthesis; Biocompatible Materials; Cellulose; Nanostructures; Hydroxypropyl Cellulose; Molecular Weight; Synthesis
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-7709DOI: 10.1021/bm7007394ISI: 000251547600019Scopus ID: 2-s2.0-38049034907OAI: oai:DiVA.org:kth-7709DiVA: diva2:12814
Note
QC 20100826Available from: 2007-11-23 Created: 2007-11-23 Last updated: 2010-08-26Bibliographically approved
In thesis
1. Tuning Properties of Surfaces and Nanoscopic Objects using Dendronization and Controlled Polymerizations
Open this publication in new window or tab >>Tuning Properties of Surfaces and Nanoscopic Objects using Dendronization and Controlled Polymerizations
2007 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

In this study, dendronization and grafting via controlled polymerization techniques, atom transfer radical polymerization (ATRP) and ring-opening polymerization (ROP), have been explored. Modification of surfaces and cellulose using these techniques, which enable grafting of well-defined polymer architectures, has been investigated. The interest in using cellulose stems from its renewability, biocompatibility, high molecular weight, and versatile functionalization possibilities.

Dendronization was performed using disulfide-cored didendrons of 2,2-bis(methylol)propionic acid (bis-MPA) on gold surfaces, for the formation of self-assembled monolayers. It was found that the height of the monolayer increased with increasing dendron generation and that the end-group functionality controlled the wettability of the modified surface.

Superhydrophobic cellulose surfaces could be obtained when a ‘graft-on-graft’ architecture was obtained using ATRP from filter paper after subsequent post-functionalized using a perfluorinated compound. The low wettability could be explained by a combination of a high surface roughness and the chemical composition.

Biobased dendronized polymers were synthesized through the ‘attach to’ route employing dendronization of soluble cellulose, in the form of hydroxypropyl cellulose (HPC). The dendronized polymers were studied as nanosized objects using atomic force microscopy (AFM) and it was found that the dendron end-group functionality had a large effect on the molecular conformation on surfaces of spun cast molecules.

ATRP of vinyl monomers was conducted from an initiator-functionalized HPC and an initiator-functionalized first generation dendron, which was attached to HPC. The produced comb polymers showed high molecular weight and their sizes could be estimated via AFM of spun cast molecules on mica and from dynamic light scattering in solution, to around 100-200 nm. The comb polymers formed isoporous membranes, exhibiting pores of a few micrometers, when drop cast from a volatile solvent in a humid environment. HPC was also used to initiate ROP of ε-caprolactone, which was chain extended using ATRP to achieve amphiphilic comb block copolymers. These polymers could be suspended in water, cross-linked and were able to solubilize a hydrophobic compound.

Place, publisher, year, edition, pages
Stockholm: KTH, 2007. 70 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2007:83
Keyword
Dendrimers, dendronized polymers, cellulose, Atom Transfer Radical Polymerization, Ring-Opening Polymerization, surface modification, grafting, superhydrophobic, amphiphilic polymer, block copolymer, Atomic Force Microscopy
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4550 (URN)978-91-7178-820-7 (ISBN)
Public defence
2007-12-14, D3, Huvudbyggnaden, Lindstedtsvägen 5, Stockholm, 14:00
Opponent
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Note
QC 20100826Available from: 2007-11-23 Created: 2007-11-23 Last updated: 2010-08-26Bibliographically approved

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Malmström, Eva

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