Dithiocyanurates and thiocyamelurates: Thermal thiyl radical generators as flame retardants in polypropylene

Höhne, Carl‐Christoph; Posern, Christian; Böhme, Uwe; Eichler, Franziska; Kroke, Edwin

doi:10.1016/j.polymdegradstab.2019.05.004

Cited by 13 publications

(37 citation statements)

References 20 publications

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“…Path a : Cyameluric chloride reacts immediately with H 2 S at room temperature in a toluene solution in the presence of N , N ‐diisopropylethylamine. No reaction can be observed without the amine base which is already known for the reaction of cyameluric chloride with octylthiol and isopropylthiol . A reaction with sodium sulfide or lithium sulfide does not give the respective thiocyameluric acid salt, either.…”

Section: Resultsmentioning

confidence: 89%

“…In contrast to triphenylthiocyamelurate (decomposition T Onset 393 °C) the decomposition temperature of 2 is much lower and similar to the analogous s ‐triazine derivative…”

Section: Resultsmentioning

confidence: 90%

“…Other measurements have shown that the substituent on the sulfur atom has a strong influence on the fluorescence . Enhanced fluorescence was reported for arylthiocyamelurates dissolved in polypropylene, compared to powder samples of the same s ‐hepatzine compounds …”

Section: Resultsmentioning

confidence: 98%

“…In previous work we described triaryl‐ and trialkylthiocyamelurates as sulfur analogues . While aromatic thiols react easily with cyameluric chloride the nucleophilicity of alkyl thiols is too low for the reaction.…”

Section: Introductionmentioning

confidence: 99%

“…The reaction with sulfenyl chlorids leads to dithiocyanurates. These compounds proved to be promising flame retardants for polypropylene . The s ‐heptazine derivatives show flame retardant effects, but the high thermal stability is assumed to prevent the release of higher amounts of flame retarding thiyl radical species during the decomposition of polypropylene matrix.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Posern

Höhne

Böhme

et al. 2019

Chemistry A European J

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Thiocyameluric acidC 6 N 7 S 3 H 3 ,the tri-thio analogue of cyameluric acid, is ak ey compound for the synthesis of new s-heptazine (tri-s-triazine) derivatives. Here, two different routes for the synthesis of thiocyamelurica cid and its reaction to tris(aryldithio)-and tris(alkyldithio)cyamelurates C 6 N 7 (SSR) 3 are reported as well as transformation to alkali metal thiocyamelurates M 3 [C 6 N 7 S 3 ], M= Na, K. Thesec ompoundsw ere characterisedb yF TIR, Raman, solution 13 Ca nd 1 HNMR spectroscopies, thermal gravimetric analysis( TGA) and elementala nalysis. The three (de)protonation steps of thiocyamelurica cid were investigated by acid-base titration followed via UV/Vis absorptions pectroscopy.W hile it was not possible to determine the three pK a values, it could be postulated that the acid strength probably increases in the following order:cyanuric acid (C 3 N 3 O 3 H 3 ) < thiocyanuric acid (C 3 N 3 S 3 H 3 ) < cyameluric acid (C 6 N 7 O 3 H 3 ) < thiocyameluric acid (C 6 N 7 S 3 H 3 ). Single crystalso fN a 3 [C 6 N 7 S 3 ]·10 H 2 Oa nd K 3 [C 6 N 7 S 3 ]·6 H 2 Ow ere obtained and the structures analyzed by single crystal X-ray diffraction. Additionally,q uantum chemicalc alculationsw ere performed to get insights into the electronic structure of thiocyameluric acid and to clarify the thiol-thione tautomerism.B ased on ac omparison of calculated and measuredv ibrational spectra it can be concluded that thiocyamelurica cid and the di-and mono-protonated anionsexist in the thione form.Scheme1.Principalstructures of the s-triazine derived cyanurates [C 3 N 3 O 3 ] 3À ,a nd the s-heptazine derived cyamelurates [C 6 N 7 O 3 ] 3À and their thio analogues. For ab etterc omparisonw ith cyameluricacid andcyamelurates we named 2,5,8-trimeracpto-tri-s-triazine and its derivatives thiocyameluric acid, thiocyameluratesa nd the disulfidesa re named dithiocyamelurates.[a] C.Supporting Information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.org/10.

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Section: Resultsmentioning

confidence: 89%

“…In contrast to triphenylthiocyamelurate (decomposition T Onset 393 °C) the decomposition temperature of 2 is much lower and similar to the analogous s ‐triazine derivative…”

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Posern

Höhne

Böhme

et al. 2019

Chemistry A European J

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Other Non‐Halogenated Flame Retardants and Future Fire Protection Concepts & Needs

Morgan

Cusack

Wilkie

2021

Non‐Halogenated Flame Retardant Handbook 2 Nd Edition

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Effect of phosphorylated lignin on flame retardancy of polypropylene‐based composites

Lee

Jang

Yang

et al. 2022

J of Applied Polymer Sci

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Polypropylene (PP) is a synthetic polymer with excellent physical properties useful for various industries. However, its flammability in air limits its applications. In the present work, lignin filler was modified by phosphorylation, and characterized through chemical, structural, thermal, and morphological analyses. The resultant products were incorporated into PP to increase the flame retardancy of PP-based composites. Although, the mechanical properties of the PP composites containing 30 wt% filler deteriorated, the tensile strength was maintained. An addition of phosphorylated lignin (pL) into PP decreased the heat release rate from 1136.5 to 777.2 kW/m 2 and the total smoke release from 25.1 to 9.6 m 2 /m 2 . Furthermore, scanning electron microscopy images of the pL incorporated composites after the combustion test revealed that the solid char formed on the composites acted as a protective layer for PP. Thus, incorporating pL into PP is a feasible approach for improving its flame retardancy.

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Dithiocyanurates and thiocyamelurates: Thermal thiyl radical generators as flame retardants in polypropylene

Cited by 13 publications

References 20 publications

Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Other Non‐Halogenated Flame Retardants and Future Fire Protection Concepts & Needs

Effect of phosphorylated lignin on flame retardancy of polypropylene‐based composites

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Dithiocyanurates and thiocyamelurates: Thermal thiyl radical generators as flame retardants in polypropylene

Cited by 13 publications

References 20 publications

Synthesis of Thiocyameluric Acid C6N7S3H3, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Synthesis of Thiocyameluric Acid C6N7S3H3, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Other Non‐Halogenated Flame Retardants and Future Fire Protection Concepts & Needs

Effect of phosphorylated lignin on flame retardancy of polypropylene‐based composites

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Product

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Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

Synthesis of Thiocyameluric Acid C₆N₇S₃H₃, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates