Fragmentation mechanisms in mass spectrometry of Chemical Weapons Convention related spiro alkylphosphonates and alkyldioxaphosphinane oxides

Saeidian, Hamid; Babri, Mehran; Mirjafary, Zohreh; Naseri, Mahmood; Sarabadani, Mansour; Ashrafi, Davood; Faraz, Seyyed Sajjad Mousavi

doi:10.1016/j.ijms.2014.06.003

Cited by 14 publications

(7 citation statements)

References 18 publications

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“…The fragmentation of the spirobis(phosphate) and spirobis(phosphonate) flame retardant in TG‐MS analysis is different. The fragmentation of spirocyclic phosphonates in MS experiments is already investigated and described in the literaure . Some found fragments of the decomposition of PCO 910 are in accordance with the decomposition pathway described in the literature.…”

Section: Resultssupporting

confidence: 70%

Flame retardant polyester by combination of organophosphorus compounds and an NOR radical forming agent

Goedderz

Weber

Markert

et al. 2019

J of Applied Polymer Sci

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Polymer materials with different surface-to-volume ratios require different mechanisms of flame retardants regarding condensed phase and gas phase activity. The flame retardant formulations in poly(ethylene terephthalate) (PET) are investigated regarding a condensed phase and gas phase activity by using thermogravimetric analysis (TGA), TG-mass spectrometry (MS), TG-Fourier transform infrared (FTIR), UL94, cone calorimeter and scanning electron microscopy-energy-dispersive X-ray spectrometer measurements. The flame retardant formulations containing phosphates, phosphonates, and phosphinates as flame retardants are analyzed by using a simultaneous analysis consisting of a differential thermal analysis-TGA device which is in situ coupled to FTIR and MS. All analysis methods show a gas phase activity for the phosphonate (PCO 910), a condensed phase activity for the phosphate (3,9-bis(phenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro-5,5-undecane-3,9-dioxide, (SPDPP) and a mixed condensed and gas phase activity for the new synthesized phosphate and 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide containing flame retardant 3, 4,8,. The fire behavior of PCO 910 can be improved by adding O,O'-Terephthaloyl-bis-N,N'-naphthalimide ester as NOR radical-forming agent (NOR-RF) reaching a total amount of 3 wt % of both active agents for a UL94 V-0 classification in PET.

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Section: Resultssupporting

confidence: 70%

Flame retardant polyester by combination of organophosphorus compounds and an NOR radical forming agent

Goedderz

Weber

Markert

et al. 2019

J of Applied Polymer Sci

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“…The fragmentation pattern of spiro alkylphosphonates is well described in the literature and can be applied on the spiro phosphate of FR 1. [34] Therefore, it is obvious that the decomposition of FR 1 leads to lots of very small fragments in comparison to FR 2-4.…”

Section: Synthesis and Characterization Of The Flame Retardantsmentioning

confidence: 99%

Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

et al. 2020

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Novel polymeric acrylate-based flame retardants (FR 1–4) containing two phosphorus groups in different chemical environments were synthesized in three steps and characterized via nuclear magnetic resonance (NMR) spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and mass spectrometry (MS). Polylactic acid (PLA) formulations with the synthesized compounds were investigated to evaluate the efficiency of these flame retardants and their mode of action by using TGA, UL94, and cone calorimetry. In order to compare the results a flame retardant polyester containing only one phosphorus group (ItaP) was also investigated in PLA regarding its flame inhibiting effect. Since the fire behavior depends not only on the mode of action of the flame retardants but also strongly on physical phenomena like melt dripping, the flame retardants were also incorporated into PLA with higher viscosity. In the UL94 vertical burning test setup, 10% of the novel flame retardants (FR 1–4) is sufficient to reach a V-0 rating in both PLA types, while a loading of 15% of ItaP is not enough to reach the same classification. Despite their different structure, TGA and cone calorimetry results confirmed a gas phase mechanism mainly responsible for the highly efficient flame retardancy for all compounds. Finally, cone calorimetry tests of the flame retardant PLA with two heat fluxes showed different flame inhibiting efficiencies for different fire scenarios.

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“…The molecular masses of these compounds were confirmed by GC/ MS(CI) (SF 41-43). Furthermore, fragments from the cleavage of the P-C bond were also absent from the spectra, whereas this dissociation was detected in the mass spectra of α-amino phosphonates [41] and spiro alkylphosphonates [42]. Again, the nature of the halogen atom (X) plays a crucial role in the fragmentation pathway of compounds 13-24.…”

Section: Resultsmentioning

confidence: 99%

GC-MS Study of Mono- and Bishaloethylphosphonates Related to Schedule 2.B.04 of the Chemical Weapons Convention: The Discovery of a New Intramolecular Halogen Transfer

Picazas-Márquez

Sierra

Nova

et al. 2016

J. Am. Soc. Mass Spectrom.

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Fragmentation mechanisms in mass spectrometry of Chemical Weapons Convention related spiro alkylphosphonates and alkyldioxaphosphinane oxides

Cited by 14 publications

References 18 publications

Flame retardant polyester by combination of organophosphorus compounds and an NOR radical forming agent

Flame retardant polyester by combination of organophosphorus compounds and an NOR radical forming agent

Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

GC-MS Study of Mono- and Bishaloethylphosphonates Related to Schedule 2.B.04 of the Chemical Weapons Convention: The Discovery of a New Intramolecular Halogen Transfer

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