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Utilizing thiol-ene coupling kinetics in the design of renewable thermoset resins based on D-limonene and polyfunctional thiols
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.ORCID iD: 0000-0003-0663-0751
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-3201-5138
2014 (English)In: RSC Advances, ISSN 2046-2069, Vol. 4, no 20, 10317-10329 p.Article in journal (Refereed) Published
Abstract [en]

An extended model is developed to predict the free-radical thiol-ene reaction dynamics between D-limonene, as a renewable diolefin, and a monothiol compound (iso-tridecyl 3-mercaptopropionate) in bulk liquid conditions. Thermally and photo-initiated reactions of the two monomers showed favored thiol-ene coupling at the exo-isopropenyl alkene structure when reacted at 1 : 1 and 1 : 0.5 mole ratios. Experimental kinetic data obtained from the two stoichiometries were well reproduced numerically via the simulation software COPASI by introducing a multi-route mechanistic scheme with propagation-chain-transfer steps accounting for primary (mono-additions) and secondary (di-addition) modes of coupling. The differences in intrinsic double-bond reactivity enable synthesis of limonene-terminated resins (mono-versus poly-disperse) as multifunctional network precursors. Off-stoichiometry manipulations in the initial mole ratio, assisted by numerical simulations, offer a convenient approach to visualize the overall reaction system kinetics irrespective of temporal effects, thus being regarded as an important guiding tool for chemists aiming at designing thiol-ene systems based on limonene.

Place, publisher, year, edition, pages
2014. Vol. 4, no 20, 10317-10329 p.
Keyword [en]
Acrylate Photopolymerizations, Cross-Linking, Polymerization, Chemistry, Monomers, Terpene
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-144011DOI: 10.1039/c3ra47922fISI: 000332061300059ScopusID: 2-s2.0-84894242321OAI: diva2:709994
Swedish Research Council, 621-2007-5723

QC 20140404

Available from: 2014-04-04 Created: 2014-04-04 Last updated: 2014-04-04Bibliographically approved

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