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

• Published in: European polymer journal 2013-04, Vol.49 (4), p.804-812
• Main Authors: van den Berg, Otto, Dispinar, Tugba, Hommez, Bart, Du Prez, Filip E.
• Format: Article
• Language: English
• Subjects: 10-Undecenoic acid; Aliphatic compounds; Applied sciences; Castor oil; Exact sciences and technology; Hydrogen peroxide; Melting; Monomers; Organic polymers; Physicochemistry of polymers; Polarity; Polycondensation; Polyethylenes; Polymerization; Polymers and radiations; Polysulfone; Polysulfone resins; Polythioether; Preparation, kinetics, thermodynamics, mechanism and catalysts; Thiol-ene
• ISSN: 0014-3057; 1873-1945
• DOI: 10.1016/j.eurpolymj.2012.12.007

[Display omitted] ► Synthesis of a biosourced AB-type thiol-ene monomer. ► Polymerization of aliphatic α-olefinic ω-thiol via thiol-ene polyaddition. ► Post-polymerization oxidative modification of polythioether to polysulfone. Polythioethers with molar masses up to 40kDa were prepared by UV- or thermal initiated thiol-ene 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.