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Ring-opening Approaches to Functional Renewable Polymers
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Polymer Technology.ORCID iD: 0000-0001-7304-6737
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
KTH Royal Institute of Technology, 2018.
Series
TRITA-CBH-FOU ; 2018:19
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-227039ISBN: 978-91-7729-781-9 OAI: oai:DiVA.org:kth-227039DiVA, id: diva2:1202930
Public defence
2018-06-05, F3, KTH Royal Institute of Technology, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
Swedish Research Council, 621201356 25Swedish Research Council Formas, 2016-00700_3
Note

QC 20180504

Available from: 2018-05-04 Created: 2018-05-02 Last updated: 2018-05-04Bibliographically approved
List of papers
1. Exploiting Ring-Opening Aminolysis–Condensation as a Polymerization Pathway to Structurally Diverse Biobased Polyamides
Open this publication in new window or tab >>Exploiting Ring-Opening Aminolysis–Condensation as a Polymerization Pathway to Structurally Diverse Biobased Polyamides
2018 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602Article in journal (Refereed) Published
Abstract [en]

A pathway to biobased polyamides (PAs) via ring-opening aminolysis–condensation (ROAC) under benign conditions with diverse structure was designed. Ethylene brassylate (EB), a plant oil-derived cyclic dilactone, was used in combination with an array of diamines of diverse chemical structure, and ring-opening of the cyclic dilactone EB was revealed as a driving force for the reaction. The ROAC reactions were adjusted, and reaction conditions of 100 °C under atmospheric pressure using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst for 24 h were optimal. The structures of the polyamides were confirmed by mass spectroscopy, FTIR, and NMR, and the PAs had viscosity average molecular weights (Mη) of ∼5–8 kDa. Glassy or semicrystalline PAs with glass transition temperatures between 48 and 55 °C, melting temperatures of 120–200 °C for the semicrystalline PAs, and thermal stabilities above 400 °C were obtained and were comparable to the existing PAs with similar structures. As a proof-of-concept of their usage, one of the PAs was shown to form fibers by electrospinning and films by melt pressing. Compared to conventional methods for PA synthesis, the ROAC route portrayed a reaction temperature at least 60–80 °C lower, could be readily carried out without a low-pressure environment, and eliminated the use of solvents and toxic chemicals. Together with the plant oil-derived monomer (EB), the ROAC route provided a sustainable alternative to design biobased PAs.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2018
National Category
Textile, Rubber and Polymeric Materials Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-225835 (URN)10.1021/acs.biomac.8b00322 (DOI)
Note

QC 20180418

Available from: 2018-04-09 Created: 2018-04-09 Last updated: 2018-05-02Bibliographically approved
2. From Food Additive to High-Performance Heavy Metal Adsorbent: A Versatile and Well-Tuned Design
Open this publication in new window or tab >>From Food Additive to High-Performance Heavy Metal Adsorbent: A Versatile and Well-Tuned Design
2016 (English)In: ACS Sustainable Chemistry & Engineering, ISSN 2168-0485Article in journal (Refereed) Published
Abstract [en]

A biosourced, cross-linked hydrogel-type heavy metal adsorbent is presented. Various factors such as the highly efficient chemical interactions, the various network structures, the decreased energy consumption during cross-linking, and the negligible amount of generated waste are considered when designing the adsorbent. The widely applied, naturally occurring food additive δ-gluconolactone is studied as a building block for the adsorbent. Aminolysis reactions were applied to form linear dimer precursors between diamines and δ-gluconolactones. The abundant hydroxyl groups on the dimers from δ-gluconolactone were fully exploited by using them as the cross-linking sites for reactions with ethylenediaminetetraacetic dianhydride, a well-known metal-chelating moiety. The versatility of the adsorbent and its metal-ion binding capacity is well tuned using dimers with different structures and by controlling the feed ratios of the precursors. Buffers with different pH values were used as the conditioning media to examine the swelling properties and the mechanical properties of the hydrogels, revealing that both properties can be controlled. High heavy metal chelating performance of the adsorbent was determined by isothermal adsorption kinetics, titration, and thermal gravimetric analysis. The adsorbent exhibits an outstanding chelating ability toward the three tested heavy metals (Cu(II), Co(II), Ni(II)), and the maximum adsorption capacity (qm ∼ 121 mg·g–1) is higher than that of the majority of the reported biosourced adsorbents.

Place, publisher, year, edition, pages
ACS Publications, 2016
National Category
Polymer Technologies
Research subject
Fibre and Polymer Science
Identifiers
urn:nbn:se:kth:diva-190063 (URN)10.1021/acssuschemeng.6b01109 (DOI)000382713100041 ()2-s2.0-84986305878 (Scopus ID)
Note

QC 20160809

Available from: 2016-08-02 Created: 2016-08-02 Last updated: 2018-05-02Bibliographically approved
3. Isocyanate-Free, UV-Crosslinked Poly(Hydroxyurethane) Networks: A Sustainable Approach toward Highly Functional Antibacterial Gels
Open this publication in new window or tab >>Isocyanate-Free, UV-Crosslinked Poly(Hydroxyurethane) Networks: A Sustainable Approach toward Highly Functional Antibacterial Gels
2017 (English)In: Macromolecular Bioscience, ISSN 1616-5187, E-ISSN 1616-5195Article in journal (Refereed) Published
Abstract [en]

An increased sustainabile awarness has inspired the development of new polymeric networks in a remarkable way and this strive should be combined with environmentally concerned end-uses. Therefore, a UV-crosslinked polyhydroxyurethane film with antibacterial properties is developed. First, a hydroxyurethane precursor is synthesized using aminolysis condensation, circumventing the use of isocyanates. The films are subsequently crosslinked under solvent-free conditions through a UV-triggered thiol-ene mechanism. The reactions are monitored by 1H nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and Raman spectroscopy, and the networks have gel contents above 90%, and are transparent, hydrophilic, and highly flexible. Antibacterial properties are achieved by a controlled quaternization of the network's tertiary-amine and methylation of thiol-ether functionality, resulting in quaternary ammonium compounds (QACs) and sulfonium compounds. The antibacterial properties are evaluated against both Escherichia coli and Staphylococcus aureus using the agar plate diffusion and tube shaking methods. The QAC-loaded films exhibit outstanding bactericide properties (>99.9%) and the antibacterial mechanism is demonstrated to be a dual killing mechanism, i.e., diffusion killing and contact active killing.

Place, publisher, year, edition, pages
John Wiley & Sons, 2017
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-214965 (URN)10.1002/mabi.201700190 (DOI)000415130800012 ()2-s2.0-85033666355 (Scopus ID)
Funder
Swedish Research Council Formas, 2016-00700_3Swedish Research Council, 621201356 25
Note

QC 20171003

Available from: 2017-09-27 Created: 2017-09-27 Last updated: 2018-05-02Bibliographically approved

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The full text will be freely available from 2019-05-04 14:51
Available from 2019-05-04 14:51

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