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Issue 20, 2014
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Utilizing thiol–ene coupling kinetics in the design of renewable thermoset resins based on D-limonene and polyfunctional thiols

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Abstract

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.

Graphical abstract: Utilizing thiol–ene coupling kinetics in the design of renewable thermoset resins based on d-limonene and polyfunctional thiols

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Publication details

The article was received on 23 Dec 2013, accepted on 31 Jan 2014 and first published on 03 Feb 2014


Article type: Paper
DOI: 10.1039/C3RA47922F
Citation: RSC Adv., 2014,4, 10317-10329
  • Open access: Creative Commons BY license
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    Utilizing thiol–ene coupling kinetics in the design of renewable thermoset resins based on D-limonene and polyfunctional thiols

    M. Claudino, M. Jonsson and M. Johansson, RSC Adv., 2014, 4, 10317
    DOI: 10.1039/C3RA47922F

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