Renewable sulfur-containing thermoplastics via AB-type thiol-ene polyaddition

Abstract

Polythioethers with molar masses up to 40 kDa were prepared by UV-or thermal initiated thiolene polyaddition polymerization of an aliphatic α-olefinic ω-thiol, an AB-type monomer derived from 10-undecenoic acid, which is a bio-sourced building block obtained from castor oil. The low polarity of the starting compound and the stability of the thioether functions formed during polymerization allowed for the synthesis of polymers with similar structures to existing bulk and engineering plastics such as polyethylene. The presence of the thioether functions offered the opportunity to oxidize these polyethylene analogues by hydrogen peroxide into sulfone linkages, resulting in polysulfones, which are valuable as engineering plastic in several application fields.Thermal analysis demonstrated the increased thermal stability and melting temperature (175°C) of these polysulfones.

Fatty Acid–Derived Aliphatic Long Chain Polyethers by a Combination of Catalytic Ester Reduction and ADMET or Thiol‐Ene Polymerization

“…Interestingly, the melting point for silylated P2f barely increased from 64.0 to 65.8 °C. In general, DSC analysis of P2a – P2e showed two close melting peaks, which is common for oxidized thiol‐ene polymers and known from literature . Such behavior is indicative of the recrystallization of different crystal forms in polar polymeric materials and also observed, for instance, for Nylon 6.6 .…”

Fully biobased triblock copolyesters from l-lactide and sulfur-containing castor oil derivatives: Preparation, oxidation and characterization

“…Sulfones exhibit a high polarity and thus, changes in thermal behaviour and crystallinity of the related polymers are expected [30]. It was found that hydrogen peroxide is able to selectively oxidize the thioether to sulfoxide or to sulfone groups depending on the reaction temperature [31].…”

Protected thiol strategies in macromolecular design

“…Du Prez and co-workers [195] used thioacetates in the preparation of bio-sourced polythioethers. Starting from 10-undecenoic acid as a renewable resource, it was possible to prepare an α-olefinic ω-thiol monomer.…”