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http://hdl.handle.net/1942/30887
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DC Field | Value | Language |
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dc.contributor.author | Stouten, Jules | - |
dc.contributor.author | VANPOUCKE, Danny E.P. | - |
dc.contributor.author | Van Assche, Guy | - |
dc.contributor.author | Bernaerts, Katrien, V | - |
dc.date.accessioned | 2020-03-30T12:08:44Z | - |
dc.date.available | 2020-03-30T12:08:44Z | - |
dc.date.issued | 2020 | - |
dc.date.submitted | 2020-03-30T11:55:12Z | - |
dc.identifier.citation | MACROMOLECULES, 53 (46) , p. 1388 -1404 | - |
dc.identifier.uri | http://hdl.handle.net/1942/30887 | - |
dc.description.abstract | The controlled polymerization of a new biobased monomer, 4-oxocyclopent-2-en-1-yl acrylate (4CPA), was established via reversible addition-fragmentation chain transfer (RAFT) (co)polymerization to yield polymers bearing pendent cyclopentenone units. 4CPA contains two reactive functionalities, namely, a vinyl group and an internal double bond, and is an unsymmetrical monomer. Therefore, competition between the internal double bond and the vinyl group eventually leads to gel formation. With RAFT polymerization, when aiming for a degree of polymerization (DP) of 100, maximum 4CPA conversions of the vinyl group between 19.0 and 45.2% were obtained without gel formation or extensive broadening of the dispersity. When the same conditions were applied in the copolymerization of 4CPA with lauryl acrylate (LA), methyl acrylate (MA), and isobornyl acrylate, 4CPA conversions of the vinyl group between 63 and 95% were reached. The additional functionality of 4CPA in copolymers was demonstrated by model studies with 4-oxocyclopent-2-en-1-yl acetate (1), which readily dimerized under UV light via [2 + 2] photocyclodimerization. First-principles quantum mechanical simulations supported the experimental observations made in NMR Based on the calculated energetics and chemical shifts, a mixture of head-to-head and head-to-tail dimers of (1) were identified. Using the dimerization mechanism, solvent-cast LA and MA copolymers containing 30 mol % 4CPA were cross-linked under UV light to obtain thin films. The cross-linked films were characterized by dynamic scanning calorimetry, dynamic mechanical analysis, IR, and swelling experiments. This is the first case where 4CPA is described as a monomer for functional biobased polymers that can undergo additional UV curing via photodimerization. | - |
dc.description.sponsorship | J.S., D.E.P.V., and K.V.B. acknowledge the project D-NL-HIT carried out in the framework of INTERREG-Program Deutschland-Nederland, which is co-financed by the European Union; the MVVIDE NRW; the Ministerie van Economische Zaken en Klimaat; and the provinces of Limburg, Gelderland, NoordBrabant, and Overijssel. The computational resources and services used in this work were provided by the VSC (Flemisch Supercomputer Center), funded by the Research Foundation Flanders (FWO) and the Flemisch Government department EWI. | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.rights | This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. | - |
dc.subject.other | Enzymatic Kinetic Resolution | - |
dc.subject.other | Fragmentation Chain Transfer | - |
dc.subject.other | Extending Hirshfeld-I | - |
dc.subject.other | Radical Polymerization | - |
dc.subject.other | Melting Transitions | - |
dc.subject.other | Bis-Isoxazolines | - |
dc.subject.other | Photodimerization | - |
dc.subject.other | Copolymers | - |
dc.subject.other | Conversion | - |
dc.subject.other | Anthracene | - |
dc.title | UV-Curable Biobased Polyacrylates Based on a Multifunctional Monomer Derived from Furfural | - |
dc.type | Journal Contribution | - |
dc.identifier.epage | 1404 | - |
dc.identifier.issue | 46 | - |
dc.identifier.spage | 1388 | - |
dc.identifier.volume | 53 | - |
local.format.pages | 17 | - |
local.bibliographicCitation.jcat | A1 | - |
dc.description.notes | Bernaerts, KV (reprint author), Maastricht Univ, Fac Sci & Engn, AMIBM, NL-6167 RD Geleen, Netherlands. | - |
dc.description.notes | katrien.bernaerts@maastrichtuniversity.nl | - |
dc.description.other | Bernaerts, KV (reprint author), Maastricht Univ, Fac Sci & Engn, AMIBM, NL-6167 RD Geleen, Netherlands. katrien.bernaerts@maastrichtuniversity.nl | - |
local.publisher.place | 1155 16TH ST, NW, WASHINGTON, DC 20036 USA | - |
local.type.refereed | Refereed | - |
local.type.specified | Article | - |
dc.source.type | Article | - |
dc.identifier.doi | 10.1021/acs.macromol.9b02659 | - |
dc.identifier.pmid | 32116389 | - |
dc.identifier.isi | WOS:000517351100028 | - |
dc.contributor.orcid | Vanpoucke, Danny/0000-0001-5919-7336; Bernaerts, | - |
dc.contributor.orcid | Katrien/0000-0002-2939-2963 | - |
dc.identifier.eissn | 1520-5835 | - |
local.provider.type | wosris | - |
local.uhasselt.uhpub | yes | - |
item.accessRights | Open Access | - |
item.validation | ecoom 2021 | - |
item.contributor | Stouten, Jules | - |
item.contributor | VANPOUCKE, Danny E.P. | - |
item.contributor | Van Assche, Guy | - |
item.contributor | Bernaerts, Katrien, V | - |
item.fulltext | With Fulltext | - |
item.fullcitation | Stouten, Jules; VANPOUCKE, Danny E.P.; Van Assche, Guy & Bernaerts, Katrien, V (2020) UV-Curable Biobased Polyacrylates Based on a Multifunctional Monomer Derived from Furfural. In: MACROMOLECULES, 53 (46) , p. 1388 -1404. | - |
crisitem.journal.issn | 0024-9297 | - |
crisitem.journal.eissn | 1520-5835 | - |
Appears in Collections: | Research publications |
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File | Description | Size | Format | |
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stouten.pdf | Published version | 4.42 MB | Adobe PDF | View/Open |
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