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Exploiting Ring-Opening Aminolysis–Condensation as a Polymerization Pathway to Structurally Diverse Biobased Polyamides
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0001-7304-6737
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0002-5850-8873
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: urn:nbn:se:kth:diva-225835DOI: 10.1021/acs.biomac.8b00322ISI: 000432476800020PubMedID: 29584417Scopus ID: 2-s2.0-85047009192OAI: oai:DiVA.org:kth-225835DiVA, id: diva2:1196104
Funder
Swedish Research Council, 621201356 25
Note

QC 20180418

Available from: 2018-04-09 Created: 2018-04-09 Last updated: 2018-06-18Bibliographically approved
In thesis
1. Ring-opening Approaches to Functional Renewable Polymers
Open this publication in new window or tab >>Ring-opening Approaches to Functional Renewable Polymers
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:nbn:se:kth:diva-227039 (URN)978-91-7729-781-9 (ISBN)
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

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