Novel thermal curing of cycloaliphatic resins by thiol-epoxy click process with several multifunctional thiols

Polymer InternationalVolume 66, Issue 12 p. 1697-1707 Research Article Novel thermal curing of cycloaliphatic resins by thiol–epoxy click process with several multifunctional thiols Dailyn Guzmán, Dailyn Guzmán Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainSearch for more papers by this authorBlai Mateu, Blai Mateu Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainSearch for more papers by this authorXavier Fernández-Francos, Xavier Fernández-Francos Thermodynamics Laboratory, ETSEIB University Politècnica de Catalunya, SpainSearch for more papers by this authorXavier Ramis, Xavier Ramis Thermodynamics Laboratory, ETSEIB University Politècnica de Catalunya, SpainSearch for more papers by this authorAngels Serra, Corresponding Author Angels Serra angels.serra@urv.cat Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainCorrespondence to: A Serra, Department of Analytical and Organic Chemistry, University Rovira i Virgili, C/ Marcel·lí Domingo s/n, 43007 Tarragona, Spain. E-mail: angels.serra@urv.catSearch for more papers by this author Dailyn Guzmán, Dailyn Guzmán Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainSearch for more papers by this authorBlai Mateu, Blai Mateu Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainSearch for more papers by this authorXavier Fernández-Francos, Xavier Fernández-Francos Thermodynamics Laboratory, ETSEIB University Politècnica de Catalunya, SpainSearch for more papers by this authorXavier Ramis, Xavier Ramis Thermodynamics Laboratory, ETSEIB University Politècnica de Catalunya, SpainSearch for more papers by this authorAngels Serra, Corresponding Author Angels Serra angels.serra@urv.cat Department of Analytical and Organic Chemistry, University Rovira i Virgili, SpainCorrespondence to: A Serra, Department of Analytical and Organic Chemistry, University Rovira i Virgili, C/ Marcel·lí Domingo s/n, 43007 Tarragona, Spain. E-mail: angels.serra@urv.catSearch for more papers by this author First published: 20 January 2017 https://doi.org/10.1002/pi.5336Citations: 23Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract Novel thermosets were prepared by the base-catalysed reaction between a cycloaliphatic resin (ECC) and various thiol crosslinkers. 4-(N,N-Dimethylaminopyridine) (DMAP) was used as base catalyst for the thiol–epoxy reaction. A commercial tetrathiol (PETMP) and three different thiols synthesized by us, 6SH-SQ, 3SH-EU and 3SH-ISO, were tested. 6SH-SQ and 3SH-EU were prepared from vinyl or allyl compounds from renewable resources such as squalene and eugenol, respectively. Thiol 3SH-ISO was prepared starting from commercially available triallyl isocyanurate. A kinetic study of the mixtures was performed using differential scanning calorimetry. Stoichiometric ECC/thiol/DMAP formulations were cured at 120 °C for 1 h, at 150 °C for 1 h and post-cured for 30 min at 200 °C. The materials were characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis and dynamic mechanical thermal analysis. The results revealed that the materials obtained from the synthesized thiols had higher thermal stability and glass transition temperatures than those obtained from the commercial PETMP. In addition, all the materials obtained exhibited very good transparency. This study proves the ability of multifunctional thiols to crosslink cycloaliphatic epoxy resins, leading to more flexible materials than those obtained by cationic homopolymerization of ECC or base-catalysed ECC–anhydride copolymerization. © 2017 Society of Chemical Industry Citing Literature Supporting Information Filename Description pi5336-sup-0001-SuppInfo.docxWord 2007 document , 236.3 KB Figure A 13C NMR spectrum of the trithiol (3SH-ISO) derived from triallyl isocyanurate registered in CDCl3 Figure B. 13C NMR spectrum of the trithiol (3SH-EU) derived from eugenol registered in CDCl3 Figure C. DSC thermograms corresponding to the dynamic curing at 10°C/min of ECC/3SH-ISO stoichiometric mixtures with 2 phr of the different catalysts. Figure D. DSC thermograms corresponding to the dynamic curing at 10°C/min of ECC/3SH-EU stoichiometric mixtures with 2 phr of the different catalysts. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume66, Issue12December 2017Pages 1697-1707 RelatedInformation