Preparation and characterization of bis-[1,3,5]triazinyl diazenes and their utilization as flame retardants in polypropylene films

Teija Tirri, Melanie Aubert, Weronika Pawelec, Carl-Eric Wilen, Rudolf Pfaendner, Holger Hoppe, Michael Roth, Jari Sinkkonen

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    Abstract

    A series of bis-[1,3,5]triazinyl diazenes and two metal complexes thereof were synthesized and tested as new flame retardants in polypropylene films. It was observed that electron withdrawing triazinyl ring substituent (i.e., Cl and phenyl moieties) improved the thermal stability of diazene compounds, whereas electron donating groups (i.e., methoxy, dimethylamino, and ethylthio moieties) had a destabilizing effect. TGA, DTA/DSC, NMR, and ATR-FTIR were used for the characterization. Quantum mechanical modeling (Gaussian 09) was also utilized to facilitate the interpretation of the NMR data. Bis-(4,6-dichloro-[1,3,5]triazin-2-yl)-diazene 1 and bis-(4,6-dimethoxy-[1,3,5]triazin-2-yl)-diazene 2 were found to be effective flame retardants in polypropylene films and DIN4102-1 B2 classification was reached already at a loading of 0.5 wt %. Interestingly, the copper complex of 2 showed even higher fire retardant activity than its precursor 2, whereas the corresponding zinc complex exhibited lower flame retardant efficacy than its precursor.
    Original languageUndefined/Unknown
    Pages (from-to)
    JournalJournal of Applied Polymer Science
    Volume131
    Issue number12
    DOIs
    Publication statusPublished - 2014
    MoE publication typeA1 Journal article-refereed

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