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Hydrolytic degradation of ROMP thermosetting materials catalysed by bio-derived acids and enzymes: from networks to linear materials

Hou, S.; Hoyle, D.M.; Blackwell, C.J.; Haernvall, K.; Perz, V.; Guebitz, G.M.; Khosravi, E.

Hydrolytic degradation of ROMP thermosetting materials catalysed by bio-derived acids and enzymes: from networks to linear materials Thumbnail


Authors

S. Hou

D.M. Hoyle

C.J. Blackwell

K. Haernvall

V. Perz

G.M. Guebitz

E. Khosravi



Abstract

This paper reports the first example of degradable ROMP thermosetting materials catalysed by bio-derived acids and cutinase from Thermobifida cellulosilytica (Thc_Cut1). The ROMP thermosetting materials are based on norbornene dicarboximides containing acetal ester groups only in the crosslinking moiety. The insoluble cross-linked materials were subjected to acid-catalysed hydrolysis using bio-derived acetic and citric acids as well as enzymatic degradation using Thc_Cut1, resulting in the materials becoming completely soluble in dichloromethane. 1H NMR and rheological analysis performed on materials after acid-catalysed hydrolysis showed characteristics indistinguishable to those of the linear polymer analogues. These analyses confirmed the cleavage of the crosslinking moiety upon degradation with the main backbone chains remaining intact. The glass transition temperatures of the polymer materials after acid-catalysed hydrolysis were the same as those observed for the linear polymer analogues. TGA showed that the cross-linked polymers were thermally stable to 150 °C, beyond which they showed weight losses due to the thermal cleavage of the acetal ester linkages.

Citation

Hou, S., Hoyle, D., Blackwell, C., Haernvall, K., Perz, V., Guebitz, G., & Khosravi, E. (2016). Hydrolytic degradation of ROMP thermosetting materials catalysed by bio-derived acids and enzymes: from networks to linear materials. Green Chemistry, 18(19), 5190-5199. https://doi.org/10.1039/c6gc00378h

Journal Article Type Article
Acceptance Date Jun 7, 2016
Online Publication Date Jun 22, 2016
Publication Date Oct 7, 2016
Deposit Date Jun 23, 2016
Publicly Available Date Jun 7, 2017
Journal Green Chemistry
Print ISSN 1463-9262
Electronic ISSN 1463-9270
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 18
Issue 19
Pages 5190-5199
DOI https://doi.org/10.1039/c6gc00378h

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