Development of Antioxidant Poly(thioether-Ester) Nanoparticles

Abstract

Poly(Thioether-Ester) nanoparticles synthetized via thiol-ene polymerization from a renewable castor oil monomer are produced by miniemulsion polymerization and emulsification/evaporation of pre-formed polymer. Its antioxidant activity, probably due to the oxidation of sulfide groups, is confirmed by 2,2-diphenyl-1picryl hydrazyl (DPPH) free radical-scavenging and β-carotene/linoleic acid assays, with an amount of polymer required to reduce the initial concentration of DPPH• radicals by 50% of ~195 µg.ml-1 promoting hydrogen or electron exchange and the capability to prevent lipid peroxidation of ~55%. The results show a promising application in food packing.

γ-Thiobutyrolactone – ethylene carbonate decarboxylative copolymerization, an original pathway to prepare aliphatic oxidizable poly(γ-thioether ester)

“…31 PTE nanoparticles have been prepared by thiol-ene mini-emulsion polymerization, 32,33 and have various properties, such as in vitro bio-compatibility, degradability by enzymes 34 or anti-oxidant activity. 35 Some examples of biobased PTE have also been described using lignin-derived phenolic compounds, 36 furfural-derived compound, 37 or 10-undecenoic acid/isosorbide/butanedithiol. 38 Our group is interested in the use of thiolactones for macromolecular engineering 39,40 and developed an easy-to-implement synthetic routes for the preparation of well-defined functional PTE by alternating ringopening polymerization of thiolactone and epoxide monomers.…”

Droplet nucleation in miniemulsion thiol–ene step photopolymerization

“…12 However, unlike thiol-ene photopolymers, the share hold by thiol-ene latexes has remained limited, and no commercial product has emerged yet. 13,14 The main examples result from a miniemulsion photopolymerization, [15][16][17][18][19][20][21][22][23][24] and to a less extent, dispersion 25,26 and emulsion 12,27 (photo)polymerizations. Suspension photopolymerization has been also described, [28][29][30][31][32] but this process does not result in polymer colloids (average particle diameter < 1 µm), but in micrometre solid beads (0.1 -10 mm).…”

“…The most used process in this field is miniemulsion thiolene polymerization. [15][16][17][18][19][20][21][22][23][24] Involving smaller and therefore less scattering monomer droplets (50 -500 nm) than an emulsion polymerization, it has the added advantage of imparting greater radiation penetration within the reactor. In addition, Please do not adjust margins Please do not adjust margins the desired particle nucleation mode occurs via radical capture into the monomer droplets, subsequently converted into polymer particles.…”