Novel organophosphorus flame retardants and their synergistic application in novolac epoxy resin

Schmidt, Christian; Ciesielski, Michael; Greiner, Lara; Döring, Manfred

doi:10.1016/j.polymdegradstab.2018.09.001

Cited by 85 publications

(39 citation statements)

References 48 publications

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“…This is also consistent with previously published data showing that R‐(DDPO) 2 does not pass the UL94V test even with a phosphorus load of 3.0 wt% and a phosphorus content of 1.6 wt% provided by R(DOPO) 2 achieves a V0 rating 3 . Compared to similar FR systems this cannot be surpassed neither by the cyclic phosphazene [NP(OPh) 2 ] 3 which leads to a V0 rating at a minimum phosphorus concentration of 1.4 wt% nor by the nitrogen free mixed phosphorus compound DOPO–PEPA which fails when incorporated with a phosphorus content of 1.5 wt% 17,20 …”

Section: Resultsmentioning

confidence: 99%

“…[26][27][28] Recently phosphazenic compounds including phosphazene based oligomeric epoxy resins and phosphazene-DOPO adducts have been investigated as flame retardants for epoxy resins. 17,[29][30][31] In this work, the flame-retardant properties of the Nphosphorylated iminophosphoranes DOPO N PPh 3 and DOPO N P(OPh) 3 ( Figure 2) were investigated incorporating these compounds in two different epoxy resin systems, which differ fundamentally not only in their material and structural properties but also in their burning behavior.…”

Section: Introductionmentioning

confidence: 99%

“…To date there are only limited examples of their use as flame retardants for polymeric materials, for example, the N ‐(thio)phosphorylated iminophosphoranes with R  R” 2  C 6 H 5 25 and some heterocyclic iminophosphoranes 26–28 . Recently phosphazenic compounds including phosphazene based oligomeric epoxy resins and phosphazene‐DOPO adducts have been investigated as flame retardants for epoxy resins 17,29–31 …”

Section: Introductionmentioning

confidence: 99%

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N‐phosphorylated Iminophosphoranes based on 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide and their flame‐retardant behavior in epoxy resins

Weinert

Döring

2020

J of Applied Polymer Sci

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Two novel N-phosphorylated iminophosphoranes based on 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) were evaluated as flame retardant (FR) additives. They were incorporated in two different epoxy resin systems (EP) based on diglycidyl ether of bisphenol A (DGEBA) and a novolac glycidyl ether (DEN438) both cured with dicyandiamide/fenuron (D/F). Decomposition temperatures and char yields of the cured EP were evaluated and compared to the corresponding neat EP as well as to structurally related compounds. The flame-retardant properties were investigated using the UL-94 V test and further verified with cone calorimetry. The N-phosphorylated iminophosphoranes with DOPO moieties exhibit distinctive flame-retardant effects in DGEBA/D/F and DEN438/D/F, depending on the chemical environment around the second phosphorus atom, even with low FR content. If the iminophosphorane is triphenyl phosphite based the mode of action is assigned to act mainly in the condensed phase hence being advantageous in DGEBA/ D/F compared to the triphenylphosphine-based iminophosphorane, which in turn is more active in the gas phase resulting in superiority in DEN438/D/F.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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N‐phosphorylated Iminophosphoranes based on 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide and their flame‐retardant behavior in epoxy resins

Weinert

Döring

2020

J of Applied Polymer Sci

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“…One of the most common and effective ways to achieve enhancement in the properties of polymers, including flame retardant properties and thermal stability, is the incorporation of fillers of an inorganic and organic nature into epoxy resin [7][8][9][10][11][12]. In recent years, special attention was paid to the use of nanodispersed materials as fillers.…”

Section: Introductionmentioning

confidence: 99%

Thermal Behavior and Flammability of Epoxy Composites Based on Multi-Walled Carbon Nanotubes and Expanded Graphite: A Comparative Study

et al. 2020

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Reduction of flammability and improvement of thermal stability of polymers during heating can be achieved by the introduction of fillers. Epoxy composites filled with different loadings of multi-walled carbon nanotubes (MWCNTs) and expanded graphite (EG) were prepared. The thermal oxidation stability of the prepared samples was investigated under heating in an oxidizing atmosphere using thermal analysis. The hardness was measured using the Shore D hardness test. The flammability of the prepared composites was evaluated by the ignition temperature and time-to-ignition. It was found that there was a rise in temperature corresponding to a 5% weight loss during heating for both epoxy/MWCNT and epoxy/EG composites compared to neat epoxy resin. The Shore D hardness of epoxy/MWCNT composites increased with content growth up to 0.1 wt.% and decreased with further concentration rise. The addition of MWCNTs and EG leads to an increase in the ignition temperature. It has been shown that MWCNTs improve the thermal behavior of epoxy resin in a low temperature region (below ~ 300 °C) whereas EG shows almost the same thermal behavior above 300 °C. The improvement of thermal properties can be achieved using MWCNTs and EG as fillers.

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“…Less often, reactive flame retardant compounds are covalently incorporated into the polymer during polymerization. This is a particularly attractive approach for suitably-modified vinyl monomers [6][7][8][9][10][11]. Many flame retardants function by promoting the formation of protective char layer at the surface of the degrading polymer, while others release volatile components to the gas phase which scavenge combustion-propagating radicals [12].…”

Section: Introductionmentioning

confidence: 99%

Incorporation of Comonomer exo-5-(Diphenylphosphato)Isosorbide-2-endo-Acrylate to Generate Flame Retardant Poly(Styrene)

Howell

Daniel

2019

Polymers

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A phosphorus containing acrylate monomer has been constructed from isosorbide, a renewable biomaterial. Treatment of isosorbide with diphenylchlorophosphate generates a mixture of phosphorus esters from which exo-5-(diphenylphosphato)isosorbide-2-endo-ol may be isolated using column chromatography. Conversion of the alcohol to the corresponding acrylate by treatment with acroyl chloride provides a reactive acryloyl monomer containing a diphenylphosphato unit. Copolymerization of this monomer, at levels to provide 1% or 2% phosphorus incorporation, with styrene generates a polymer with substantially diminished flammability compared to that for styrene homopolymer.

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Novel organophosphorus flame retardants and their synergistic application in novolac epoxy resin

Cited by 85 publications

References 48 publications

N‐phosphorylated Iminophosphoranes based on 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide and their flame‐retardant behavior in epoxy resins

N‐phosphorylated Iminophosphoranes based on 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide and their flame‐retardant behavior in epoxy resins

Thermal Behavior and Flammability of Epoxy Composites Based on Multi-Walled Carbon Nanotubes and Expanded Graphite: A Comparative Study

Incorporation of Comonomer exo-5-(Diphenylphosphato)Isosorbide-2-endo-Acrylate to Generate Flame Retardant Poly(Styrene)

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