Sulfides and Disulfides of s-Triazine: Potential Thermal Thiyl Radical Generators.

Chemistry

Institut für Anorganische Chemie, TU Bergakademie Freiberg, Leipziger Straße 29, 09599, Freiberg, Germany.

Published: September 2018

AI Article Synopsis

  • A variety of aliphatic and aromatic thioethers and dithioethers of s-triazine were synthesized to investigate their thermal properties, especially focusing on the ability to generate thiyl radicals when exposed to heat.
  • The synthesized compounds included both sulfides and disulfides, with various substituents like phenyl, para-tolyl, ethyl, and tert-butyl groups, and were thoroughly characterized using techniques such as NMR, infrared, and Raman spectroscopy.
  • Thermal analysis revealed that the synthesized disulfides exhibited the best radical generation potential, suggesting their possible application as flame retardants in certain polymers.

Article Abstract

A series of aliphatic and aromatic thioethers and dithioethers of s-triazine were synthesised to study their thermal properties, in particular the thermally induced thiyl radical generation ability. Four symmetric s-triazine sulfides of the type (RS) C N , namely 2,4,6-tris(phenylthio)- (1), 2,4,6-tris(para-tolylthio)- (3), 2,4,6-tris(ethylthio)- (5) and 2,4,6-tris(tert-butylthio)-1,3,5-triazine (7), as well as four symmetric s-triazine disulfides of the type (RSS) C N , namely 2,4,6-tris(phenyldithio)- (2), 2,4,6-tris(para-tolyldithio)- (4), 2,4,6-tris(ethyldithio)- (6) and 2,4,6-tris(tert-butyldithio)-1,3,5-triazine (8) were synthesised. All compounds were comprehensively characterised by H and C NMR, infrared and Raman spectroscopy as well as elemental analyses. Single-crystal X-ray diffraction analyses of 1, 2 and 5 are discussed. The thermal behaviour was studied by thermogravimetric analyses coupled with mass spectrometry (TGA-MS) and quantum chemical calculations. Limiting oxygen index (LOI) flammability tests showed that the disulfides are the most promising radical generators, and are most likely suitable flame retardants for selected polymers.

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http://dx.doi.org/10.1002/chem.201802427DOI Listing

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