Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights

By using a combination of bio-based monomers (sorbitol, 1,10-decanediol and a range of dicarboxylic acids), a series of novel sorbitol-based polyesters was prepared by solvent-free enzymatic polycondensation using an immobilized form of Candida antarctica lipase B (Novozyme 435). The aim was to prep...

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Published in:European Polymer Journal
Main Authors: Gustini, L., Noordover, B.A.J., Gehrels, C., Dietz, C.H.J.T., Koning, C.E.
Format: Article in Journal/Newspaper
Language:English
Published: 2015
Subjects:
Online Access:https://research.tue.nl/en/publications/864f1f16-4f69-436f-8e5c-39bf9a19c718
https://doi.org/10.1016/j.eurpolymj.2014.12.025
https://pure.tue.nl/ws/files/3910117/897220855726406.pdf
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spelling ftuniveindcris:oai:pure.tue.nl:publications/864f1f16-4f69-436f-8e5c-39bf9a19c718 2024-09-09T19:10:25+00:00 Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights Gustini, L. Noordover, B.A.J. Gehrels, C. Dietz, C.H.J.T. Koning, C.E. 2015 application/pdf https://research.tue.nl/en/publications/864f1f16-4f69-436f-8e5c-39bf9a19c718 https://doi.org/10.1016/j.eurpolymj.2014.12.025 https://pure.tue.nl/ws/files/3910117/897220855726406.pdf eng eng https://research.tue.nl/en/publications/864f1f16-4f69-436f-8e5c-39bf9a19c718 info:eu-repo/semantics/openAccess Gustini , L , Noordover , B A J , Gehrels , C , Dietz , C H J T & Koning , C E 2015 , ' Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights ' , European Polymer Journal , vol. 67 , pp. 459-475 . https://doi.org/10.1016/j.eurpolymj.2014.12.025 /dk/atira/pure/sustainabledevelopmentgoals/affordable_and_clean_energy name=SDG 7 - Affordable and Clean Energy article 2015 ftuniveindcris https://doi.org/10.1016/j.eurpolymj.2014.12.025 2024-08-07T23:41:55Z By using a combination of bio-based monomers (sorbitol, 1,10-decanediol and a range of dicarboxylic acids), a series of novel sorbitol-based polyesters was prepared by solvent-free enzymatic polycondensation using an immobilized form of Candida antarctica lipase B (Novozyme 435). The aim was to prepare linear polyesters with pendant, curable hydroxyl groups along the polymer backbone. To achieve this, the polyester molecular weight was controlled by tuning the reaction time, enzyme loading and reaction stoichiometry. Extensive molecular and thermal characterization was performed, showing that the obtained polyesters were semi-crystalline materials with a low Tg. The presence of sorbitol in the polyesters was confirmed through a qualitative investigation using MALDI-ToF-MS. The quantification of the sorbitol content in the polymers was achieved by inverse-gated decoupling 13C NMR spectroscopy, while 31P NMR provided information regarding the selectivity of CALB for the primary vs. the secondary hydroxyl groups. Moreover, 31P NMR and potentiometric titration were utilized for the quantitative determination of the amount of carboxylic groups and hydroxyl functional groups present in the polyesters. The obtained hydroxyl-functional polyesters had suitable properties to be applied as solvent-borne coatings in terms of their molecular weight, functionality and thermal characteristics. Cross-linked coatings were prepared using different conventional curing agents, including two renewable diisocyanates (ethyl ester l-lysine diisocyanate and dimer fatty acid-based diisocyanate). The resulting poly(ester urethane) coatings were tested in terms of solvent resistance, hardness and resistance against rapid deformation, showing the beneficial effect of the implemented sorbitol on network formation. Article in Journal/Newspaper Antarc* Antarctica Eindhoven University of Technology research portal European Polymer Journal 67 459 475
institution Open Polar
collection Eindhoven University of Technology research portal
op_collection_id ftuniveindcris
language English
topic /dk/atira/pure/sustainabledevelopmentgoals/affordable_and_clean_energy
name=SDG 7 - Affordable and Clean Energy
spellingShingle /dk/atira/pure/sustainabledevelopmentgoals/affordable_and_clean_energy
name=SDG 7 - Affordable and Clean Energy
Gustini, L.
Noordover, B.A.J.
Gehrels, C.
Dietz, C.H.J.T.
Koning, C.E.
Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
topic_facet /dk/atira/pure/sustainabledevelopmentgoals/affordable_and_clean_energy
name=SDG 7 - Affordable and Clean Energy
description By using a combination of bio-based monomers (sorbitol, 1,10-decanediol and a range of dicarboxylic acids), a series of novel sorbitol-based polyesters was prepared by solvent-free enzymatic polycondensation using an immobilized form of Candida antarctica lipase B (Novozyme 435). The aim was to prepare linear polyesters with pendant, curable hydroxyl groups along the polymer backbone. To achieve this, the polyester molecular weight was controlled by tuning the reaction time, enzyme loading and reaction stoichiometry. Extensive molecular and thermal characterization was performed, showing that the obtained polyesters were semi-crystalline materials with a low Tg. The presence of sorbitol in the polyesters was confirmed through a qualitative investigation using MALDI-ToF-MS. The quantification of the sorbitol content in the polymers was achieved by inverse-gated decoupling 13C NMR spectroscopy, while 31P NMR provided information regarding the selectivity of CALB for the primary vs. the secondary hydroxyl groups. Moreover, 31P NMR and potentiometric titration were utilized for the quantitative determination of the amount of carboxylic groups and hydroxyl functional groups present in the polyesters. The obtained hydroxyl-functional polyesters had suitable properties to be applied as solvent-borne coatings in terms of their molecular weight, functionality and thermal characteristics. Cross-linked coatings were prepared using different conventional curing agents, including two renewable diisocyanates (ethyl ester l-lysine diisocyanate and dimer fatty acid-based diisocyanate). The resulting poly(ester urethane) coatings were tested in terms of solvent resistance, hardness and resistance against rapid deformation, showing the beneficial effect of the implemented sorbitol on network formation.
format Article in Journal/Newspaper
author Gustini, L.
Noordover, B.A.J.
Gehrels, C.
Dietz, C.H.J.T.
Koning, C.E.
author_facet Gustini, L.
Noordover, B.A.J.
Gehrels, C.
Dietz, C.H.J.T.
Koning, C.E.
author_sort Gustini, L.
title Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
title_short Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
title_full Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
title_fullStr Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
title_full_unstemmed Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
title_sort enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights
publishDate 2015
url https://research.tue.nl/en/publications/864f1f16-4f69-436f-8e5c-39bf9a19c718
https://doi.org/10.1016/j.eurpolymj.2014.12.025
https://pure.tue.nl/ws/files/3910117/897220855726406.pdf
genre Antarc*
Antarctica
genre_facet Antarc*
Antarctica
op_source Gustini , L , Noordover , B A J , Gehrels , C , Dietz , C H J T & Koning , C E 2015 , ' Enzymatic synthesis and preliminary evaluation as coating of sorbitol-based, hydroxy-functional polyesters with controlled molecular weights ' , European Polymer Journal , vol. 67 , pp. 459-475 . https://doi.org/10.1016/j.eurpolymj.2014.12.025
op_relation https://research.tue.nl/en/publications/864f1f16-4f69-436f-8e5c-39bf9a19c718
op_rights info:eu-repo/semantics/openAccess
op_doi https://doi.org/10.1016/j.eurpolymj.2014.12.025
container_title European Polymer Journal
container_volume 67
container_start_page 459
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