Photoinduced thiol-ene crosslinking of globalide/e-caprolactone copolymers : curing performance and resulting thermoset properties

M. Claudino, I. Meulen, van der, S. Trey, M. Jonsson, A. Heise, M. Johansson

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Scopus)
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Abstract

The increasing demand for bioderived polymers led us to investigate the potential use of the macrolactone globalide in thermoset synthesis via the photoinduced thiol–ene reaction. A series of six lipase-catalyzed poly(globalide-caprolactone) copolyesters bearing internal main-chain unsaturations ranging from 10 to 50 and 100 mol % were successfully crosslinked in the melt with equal amounts of thiol groups from trimethylolpropane-trimercapto propionate affording fully transparent amorphous elastomeric materials with different thermal and viscoelastic properties. Three major conclusions can be drawn from this study: (i) high thiol–ene conversions (>80%) were easily attained for all cases, while maintaining the cure behavior, and irrespective of functionality at reasonable reaction rates; (ii) parallel chain-growth homopropagation of the ene monomer is insignificant when compared with the main thiol–ene coupling route; and (iii) high ene-density copolymers result in much lower extracted sol fractions and high Tg values as a result of a more dense and homogeneous crosslinked network. The thiol–ene system evaluated in this contribution serve as model example for the sustainable use of naturally occurring 1,2-disubstituted alkenes in making semisynthetic polymeric materials in high conversions with a range of properties
Original languageEnglish
Pages (from-to)16-24
Number of pages9
JournalPolymer Chemistry
Volume50
Issue number1
DOIs
Publication statusPublished - 2011

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