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Sulfides and disulfides of s-Triazine: Potential thermal thiyl radical generators

 
: Höhne, C.-C.; Posern, C.; Böhme, U.; Kroke, E.

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Chemistry. A European journal 24 (2018), Nr.51, S.13596-13606
ISSN: 0947-6539
ISSN: 1521-3765
Englisch
Zeitschriftenaufsatz
Fraunhofer ICT ()

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)3C3N3, 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)3C3N3, 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 1H and 13C 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.

: http://publica.fraunhofer.de/dokumente/N-515644.html