Bridged DOPO derivatives as flame retardants for PA6

Buczko, Aleksandra; Stelzig, Timea; Bommer, Lea; Rentsch, Daniel; Heneczkowski, Maciej; Gaan, Sabyasachi

doi:10.1016/j.polymdegradstab.2014.05.017

Cited by 134 publications

(101 citation statements)

References 28 publications

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“…Thus, the value of T 5 was of about 386˝C, the decomposition process registered a single stage with a reduction of 20˝C in the value of T max (430˝C), while the char yield had a value of 0.9 wt %. Similar data, regarding the influence of the additive on thermal stability, were obtained for different polymers and FR based on DOPO derivatives [26][27][28]. The incorporation of various DOPO-based FR additives led to a decrease in thermal stability of the corresponding polymers.…”

Section: Thermal Stabilitysupporting

confidence: 72%

“…Melamine also destabilizes PA6 and increases the dripping behavior of the polymer; therefore, the fuel source is removed from the combustion zone [22]. Concerning the phosphorous-containing flame retardants, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and its derivatives could be an attractive FR solution for PA6 due to their relatively higher thermal stability [25][26][27][28]. DOPO and its derivatives are known to predominantly act by a gas-phase mechanism, through the formation of PO¨radicals, which might also be assisted by a condensed-phase activity via the incorporation of specific functionalities at the DOPO moiety [25,29].…”

Section: Introductionmentioning

confidence: 99%

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Effect of Meltable Triazine-DOPO Additive on Rheological, Mechanical, and Flammability Properties of PA6

et al. 2015

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Through a straightforward approach, a new meltable, halogen-free, nitrogen-phosphorus-based flame retardant (FR), 6-(2-(4,6-diamino-1,3,5-triazin-2-yl)ethyl) dibenzo [c,e][1,2]oxaphosphinine 6-oxide (DTE-DOPO) was synthesized and incorporated in polyamide 6 (PA6).It was proved that a very low phosphorus content of 1.46 wt % for DTE-DOPO additive improved the flame retardancy of PA6, leading to a non-flammable material. The performance of the new additive was compared to that of the commercially-available Exolit OP 1230. The PA6 formulations were evaluated by measuring the rheological, mechanical, and flammability behavior. Using compounding by melt extrusion, 17 wt % additives was introduced into PA6 matrix and the corresponding formulations were characterized. The results evidenced a higher homogeneity of DTE-DOPO with PA6, a high thermal stability with a catalyzing decomposition effect on PA6 caused by the presence of the new developed FR, enhanced elasticity for the PA6/DTE-DOPO formulation and a V0 rating for both formulations. Thermal and fire analysis indicated a primary gas-phase activity, combined with a complete suppression of the self-sustained burning for the PA6/DTE-DOPO formulation.Polymers 2015, 7 1542

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Section: Thermal Stabilitysupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Effect of Meltable Triazine-DOPO Additive on Rheological, Mechanical, and Flammability Properties of PA6

et al. 2015

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“…It has been reported that using DOPO-derivatives (DiDopoMeO [6-((6- [73]. On contrary, when DiDopoEDA [6,6'-(ethane-1,2-diylbis(azanediyl))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide)] was used, the peak heat release rate increased.…”

Section: Pyrolysis Combustion Flow Calorimetry (Pcfc) and It Modificamentioning

confidence: 99%

An Overview of Mode of Action and Analytical Methods for Evaluation of Gas Phase Activities of Flame Retardants

et al. 2015

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Abstract:The latest techniques used to prove, describe and analyze the gas phase activity of a fire retardant used in polymeric materials are briefly reviewed. Classical techniques, such as thermogravimetric analysis or microscale combustion calorimetry, as well as complex and advanced analytical techniques, such as modified microscale combustion calorimeter (MCC), molecular beam mass spectroscopy and vacuum ultra violet (VUV) photoionization spectroscopy coupled with time of flight MS (TOF-MS), are described in this review. The recent advances in analytical techniques help not only in determining the gas phase activity of the flame-retardants but also identify possible reactive species responsible for gas phase flame inhibition. The complete understanding of the decomposition pathways and the flame retardant activity of a flame retardant system is essential for the development of new eco-friendly-tailored flame retardant molecules with high flame retardant efficiency.

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“…Namely, proper chemical bridge bonds, linking different characteristic structures or groups, potentially benet to endow bi-group or multigroup compound with higher ame-retardant efficiency, resulting from the changed and even optimized pyrolysis route of ame retardant structures or groups. [34][35][36][37][38] In this work, to adjust the pyrolysis route of phosphaphenanthrene and increase additional source of phenoxy derivative radicals, a novel bi-group compound TOD, containing two different chemical bridge bonds (aliphatic and aromatic bridge bonds) between phosphaphenanthrene and triazine-trione groups, was synthesized via the addition reactions between epoxy group/P-H bond and epoxy group/ phenolic hydroxyl group in sequence. The ame-retardant effect and mechanism of TOD were investigated in the diglycidyl ether of bisphenol-A cured with 4,4 0 -diamino-diphenyl methane (EP).…”

Section: Introductionmentioning

confidence: 99%

Flame-retardant effect of a novel phosphaphenanthrene/triazine-trione bi-group compound on an epoxy thermoset and its pyrolysis behaviour

Qiu

Qian

2016

RSC Adv.

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A novel phosphaphenanthrene/triazine-trione bi-group flame retardant TOD containing two different chemical bridge bonds between phosphaphenanthrene and triazine-trione groups was synthesized through the addition reaction of 1,3,5-triglycidyl isocyanurate (TGIC), 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and 10-(2,5-dihydroxyphenyl)-10-H-9-oxa-10-phosphaphenanthrene-10-oxide (ODOPB) three raw materials in turn. TOD was then applied to prepare the flame-retardant epoxy thermoset in the diglycidyl ether of bisphenol-A cured with 4,4 0 -diamino-diphenyl methane (EP). By a limited oxygen index (LOI) measurement, UL94 vertical burning test and cone calorimeter test, TOD was observed to efficiently endow the EP thermoset with a higher LOI value, higher UL94 rating, and reduced total heat release in combustion. The introduction of 4 wt% TOD endowed the EP thermoset with a LOI value of 35.9%, UL94 V-0 rating, 42.4% decreased peak of heat release rate, 46.5% decreased total heat release, and slightly elevated char yields. The analyses of the thermal and combustion behaviors of the epoxy thermoset as well as the pyrolysis behavior of TOD together revealed that the free radical quenching effect, inert volatile diluting effect, charring effect, and char layer barrier jointly caused the high-efficiency flame retardant mechanism of TOD in the epoxy thermoset. This suggests a possibility to further improve the flame retardant efficiency of bi-or multi-group compounds by selecting proper bridge-linking between functional groups.

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Bridged DOPO derivatives as flame retardants for PA6

Cited by 134 publications

References 28 publications

Effect of Meltable Triazine-DOPO Additive on Rheological, Mechanical, and Flammability Properties of PA6

Effect of Meltable Triazine-DOPO Additive on Rheological, Mechanical, and Flammability Properties of PA6

An Overview of Mode of Action and Analytical Methods for Evaluation of Gas Phase Activities of Flame Retardants

Flame-retardant effect of a novel phosphaphenanthrene/triazine-trione bi-group compound on an epoxy thermoset and its pyrolysis behaviour

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