An overview of some recent advances in DOPO-derivatives: Chemistry and flame retardant applications

Salmeia, Khalifah A.; Gaan, Sabyasachi

doi:10.1016/j.polymdegradstab.2014.12.014

Cited by 312 publications

(216 citation statements)

References 59 publications

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“…The three novel compounds were designed in order to possess improved flame retardation potential, but also for a wide range of applications based on their higher melting points and increased stability, which are prerequisites for their use in the production of plastic materials (Buczko et al 2014; Gaan et al 2013, 2015; Neisius et al 2014; Salmeia and Gaan 2015; Salmeia et al 2015; Qiang et al 2011). In contrast to the current practice of investigating the potential harmful properties of flame retardants after their introduction into the market, we applied here a series of human in vitro screening assays to allow a fundamental toxicological classification before the production and application of halogen-free bis -DOPO compounds on an industrial scale.…”

Section: Discussionmentioning

confidence: 99%

“…In order to improve its flame retardation potential and influence its physico-chemical parameters, such as its melting point, to allow industrial application in different plastic materials, novel phosphonamidate and phosphonate and phosphinate derivatives of DOPO have been developed (Gaan et al 2009, 2013, 2015; Buczko et al 2014; Neisius et al 2014; Salmeia and Gaan 2015; Salmeia et al 2015), but have not been evaluated with respect to their toxicological potential. In the combustion process, phosphonamidate DOPO derivatives primarily act in the vapor phase by forming phosphorus-containing radical species (PO · ) (Salmeia and Gaan 2015; Salmeia et al 2015), which interact with · OH or H · radicals (Eq. 1) formed during combustion and therefore lead to a reduction in the release of heat, favoring the extinguishing of the flame.…”

Section: Introductionmentioning

confidence: 99%

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Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Hirsch

Striegl²,

Mathes

et al. 2016

Arch Toxicol

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Halogen-free organophosphorus flame retardants are considered as replacements for the phased-out class of polybrominated diphenyl ethers (PBDEs). However, toxicological information on new flame retardants is still limited. Based on their excellent flame retardation potential, we have selected three novel 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) derivatives and assessed their toxicological profile using a battery of in vitro test systems in order to provide toxicological information before their large-scale production and use. PBDE-99, applied as a reference compound, exhibited distinct neuro-selective cytotoxicity at concentrations ≥10 µM. 6-(2-((6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)amino)ethoxy)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide (ETA-DOPO) and 6,6′-(ethane-1,2-diylbis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) (EG-DOPO) displayed adverse effects at concentrations >10 µM in test systems reflecting the properties of human central and peripheral nervous system neurons, as well as in a set of non-neuronal cell types. DOPO and its derivative 6,6′-(ethane-1,2-diylbis(azanediyl))bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) (EDA-DOPO) were neither neurotoxic, nor did they exhibit an influence on neural crest cell migration, or on the integrity of human skin equivalents. The two compounds furthermore displayed no inflammatory activation potential, nor did they affect algae growth or daphnia viability at concentrations ≤400 µM. Based on the superior flame retardation properties, biophysical features suited for use in polyurethane foams, and low cytotoxicity of EDA-DOPO, our results suggest that it is a candidate for the replacement of currently applied flame retardants.Electronic supplementary materialThe online version of this article (doi:10.1007/s00204-016-1680-4) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Hirsch

Striegl²,

Mathes

et al. 2016

Arch Toxicol

Self Cite

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“…[116] Some of the hydrogen phosphonates or phosphinates can readily be incorporated into epoxy resins [117] as the P-H bond can add across an epoxy group with the consequent ring-opening. This option is widely used to introduce DOPO-type units into the epoxies [118] suitable for electronic applications [18] . There are two other ways to prepare DOPOcontaining flame-retardant epoxies.…”

Section: Another Polymeric Curing Agent Based On α-Aminophosphinate Wmentioning

confidence: 99%

Reactive Modification of Thermoplastic and Thermoset Polymers using Flame Retardants: An Overview

Wazarkar

Kathalewar

Sabnis

2015

Polymer-Plastics Technology and Engineering

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Flame retardants are the chemicals used in thermoplastics, thermosets, textiles and coatings to arrest the spread of fire. There are basically two ways to improve flame retardancy, namely additive and reactive. It was observed that the reactive modification enhances flame retardancy of polymer to the greater extent than the additive route. Hence in this review, more emphasis is given to the reactive approach. Following review depicts various flame retardants that can be incorporated to thermoplastic and thermosetting polymers, their mechanism of action and their combined effect on flame retardant properties of polymer system in which they are incorporated in.

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“…Thus, phosphoric esters can act as plasticizers, reducing the heat resistance of the material [7]; they are also poorly compatible with epoxy polymers [8,9]. In addition, most industrial phosphorus-containing flame retardants have a relatively low degradation temperature and limited chemical resistance [5,6,10,11]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Resorcinol-Based Phosphazene-Containing Epoxy Oligomers

et al. 2019

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Phosphazene-containing epoxy-resorcinol oligomers (PERO) are synthesized in one stage with the direct interaction of hexachlorocyclotriphosphazene (HCP), resorcinol, and epichlorohydrin in the presence of solid NaOH. Depending on the initial ratio of HCP:resorcinol, PERO contains from 20 to 50 wt.% phosphazene component (2.0–4.8% of phosphorus) and have an epoxy group content up to 30 %. Products are characterized using 1H and 31P NMR spectroscopy, MALDI-TOF mass spectrometry, and elemental analysis. According to mass spectrometry, the phosphazene fractions of PERO include up to 30 individual compounds with a predominance of cyclotriphosphazenes with one unsubstituted chlorine atom and four or five glycidyl groups. PERO has a lower viscosity in comparison with similar resins based on bisphenol A, which can simplify their use as a binder for polymer composites, adhesives, and paints.

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An overview of some recent advances in DOPO-derivatives: Chemistry and flame retardant applications

Cited by 312 publications

References 59 publications

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Multiparameter toxicity assessment of novel DOPO-derived organophosphorus flame retardants

Reactive Modification of Thermoplastic and Thermoset Polymers using Flame Retardants: An Overview

Synthesis of Resorcinol-Based Phosphazene-Containing Epoxy Oligomers

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