Organic-acid mediated bulk polymerization of ε-caprolactam and its copolymerization with ε-caprolactone

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dc.contributor.authorSanchez-Sanchez, Ana
dc.contributor.authorBasterretxea, Andere
dc.contributor.authorMantione, Daniele
dc.contributor.authorEtxeberria, Agustin
dc.contributor.authorElizetxea, Cristina
dc.contributor.authorde la Calle, Amaia
dc.contributor.authorGarcía-Arrieta, Sonia
dc.contributor.authorSardon, Haritz
dc.contributor.authorMecerreyes, David
dc.contributor.institutionPOLIMEROS
dc.date.accessioned2024-07-24T12:02:04Z
dc.date.available2024-07-24T12:02:04Z
dc.date.issued2016-08-01
dc.descriptionPublisher Copyright: © 2016 Wiley Periodicals, Inc.
dc.description.abstractPolyamides (PA) constitute one of the most important classes of polymeric materials and have gained strong position in different areas, such as textiles, fibers, and construction materials. Whereas most PA are synthesized by step-growth polycondensation, PA 6 is synthesized by ring opening polymerization (ROP) of ε-caprolactam (ε-CLa). The most popular ROP methods involve the use of alkaline metal catalyst difficult to handle at large scale. In this article, we propose the use of organic acids for the ROP of ε-CLa in bulk at 180 °C (below the polymer's melting point). Among evaluated organic acids, sulfonic acids were found to be the most effective for the polymerization of ε-CLa, being the Brønsted acid ionic liquid: 1-(4-sulfobutyl)−3-methylimidazolium hydrogen sulfate the most suitable due to its higher thermal stability. End-group analysis by 1H nuclear magnetic resonance and model reactions provided mechanistic insights and suggested that the catalytic activity of sulfonic acids was a function of not only the acid strength, but of the nucleophilic character of conjugate base as well. Finally, the ability of sulfonic acid to promote the copolymerization of ε-CLa and ε-caprolactone is demonstrated. As a result, poly(ε-caprolactam-co-ε-caprolactone) copolymers with considerably randomness are obtained. This benign route allows the synthesis of poly(ester amide)s with different thermal and mechanical properties.en
dc.description.sponsorshipThe authors acknowledge the financial support of Euskampus Fundazioa, the Spanish Ministery of Economy and Competition through project CTQ2014-53458-1 and the European Commission through project SUSPOL-EJD 642671 and FP7-PEOPLE-212-ITN 316832-OLIMPIA (D. Mantione). Haritz Sardon gratefully acknowledges financial support from MINECO through project FDI 16507. A. Sanchez-Sanchez thanks “Convocatoria de Contratación para la especialización de personal investigador doctor en la UPV/EHU” for financial support. The SGIKER UPV/EHU for the NMR facilities of Gipuzkoa campus are acknowledged.
dc.description.statusPeer reviewed
dc.format.extent9
dc.identifier.citationSanchez-Sanchez , A , Basterretxea , A , Mantione , D , Etxeberria , A , Elizetxea , C , de la Calle , A , García-Arrieta , S , Sardon , H & Mecerreyes , D 2016 , ' Organic-acid mediated bulk polymerization of ε-caprolactam and its copolymerization with ε-caprolactone ' , Journal of Polymer Science, Part A: Polymer Chemistry , vol. 54 , no. 15 , pp. 2394-2402 . https://doi.org/10.1002/pola.28114
dc.identifier.doi10.1002/pola.28114
dc.identifier.issn0887-624X
dc.identifier.urihttps://hdl.handle.net/11556/3214
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=84979493845&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofJournal of Polymer Science, Part A: Polymer Chemistry
dc.relation.projectIDEuskampus Fundazioa
dc.relation.projectIDSpanish Ministery of Economy and Competition, CTQ2014-53458-1
dc.relation.projectIDSeventh Framework Programme, FP7, 316832-642671
dc.relation.projectIDEuropean Commission, EC
dc.relation.projectIDMinisterio de Economía y Competitividad, MINECO, FDI 16507
dc.relation.projectIDEuskal Herriko Unibertsitatea, EHU
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject.keywordsbiodegradable polymers
dc.subject.keywordscopolymerization
dc.subject.keywordsorganocatalysis
dc.subject.keywordspoly(ester amide)s
dc.subject.keywordspolyamides
dc.subject.keywordspolyesters
dc.subject.keywordsring-opening polymerization
dc.subject.keywordssulfonic acids
dc.subject.keywordsPolymers and Plastics
dc.subject.keywordsOrganic Chemistry
dc.subject.keywordsMaterials Chemistry
dc.titleOrganic-acid mediated bulk polymerization of ε-caprolactam and its copolymerization with ε-caprolactoneen
dc.typejournal article
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