Coordination Compounds of 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐Oxide (DOPO) Ligands: Extremely High Thermostability and Ligand Oxidation in the Solid State

Goedderz, Daniela; Schäfer, Timmy; Klitsch, Johannes; Weber, L.; Weber, Bettina; Fuhr, Olaf; Buntkowsky, Gerd; Schönberger, Frank; Döring, Manfred

doi:10.1002/ejic.202000269

Cited by 5 publications

(7 citation statements)

References 31 publications

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“…The phosphorus content of less than 0.4 wt% increased the limiting oxygen index by 2%. Daniela Goedder 7 synthesized metal phosphinate and phosphonate coordination compounds containing different metal atoms based on DOPO and DOPO‐OH. These complexes exhibited high thermal stability with decomposition temperatures above 500°C.…”

Section: Introductionmentioning

confidence: 99%

Effect of microencapsulation flame retardant on flame retardancy and mechanical properties of rigid polyurethane foams

Peng,

Li,

et al. 2023

J of Applied Polymer Sci

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A microencapsulated flame retardant PMDOPO was synthesized by solution blending method using EGDMA as initiator and AIBN as cross‐linking agent. Rigid polyurethane foams were prepared in a one‐step process. PMDOPO was incorporated into the foams by blending with polycarbonate diols (PCDL) and foaming additives. The results of Fourier transform infrared spectroscopy (FTIR) and scanning electron microscopy (SEM) showed that PMDOPO was well formed and uniformly dispersed in the foam. The pore size and density of the foams first increased and then decreased with the addition of PMDOPO. X‐ray photoelectron spectroscopy (XPS), vertical combustion test, and thermogravimetric analysis (TGA) showed that the PMDOPO content was directly proportional to the flame retardancy and the thermal stability. The major weight loss shifted to higher temperature intervals. The amount of residual char of RPUF/PMDOPO‐25 was enhanced 50 times to 10.63% compared to pure RPUF. In addition, SEM and Raman analyses of the combustion residual char revealed that a phosphorus‐containing char layer was formed during thermal degradation. The dense charcoal layer helps to insulate heat and suppress combustion. The universal testing machine showed that RPUF with 15 wt% content had the best compression resistance, with an enhancement of 1.8 MPa over pure RPUF.

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Section: Introductionmentioning

confidence: 99%

Effect of microencapsulation flame retardant on flame retardancy and mechanical properties of rigid polyurethane foams

Peng,

Li,

et al. 2023

J of Applied Polymer Sci

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“…Therefore, the DOPO moiety is used in many syntheses as a building block to achieve gas phase activity [30][31][32][33][34][35][36][37]. While most organic DOPO-containing flame retardants are thermally not stable enough to be used in PA 66, some inorganic analogous have thermal stabilities >300 • C [38]. Therefore, the Zn salt based on the phosphonate analogue DOPOx structure will be investigated in the scope of the present paper.…”

Section: Introductionmentioning

confidence: 99%

“…The DOPOx structure has been selected as the phosphinate analogue Zn-DOPO already exhibits a mass loss below the extrusion temperature of PA 66. The different chemical structures of the phosphinate salt (Zn-DOPO) and phosphonate salt (Zn-DOPOx) are reported in the literature [38] and are shown in Scheme 1. The synthesis of metal salts based on DOPO/DOPOx was first described in 1977 [39].…”

Section: Introductionmentioning

confidence: 99%

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Mode of Action of Zn-DOPOx and Melamine Polyphosphate as Flame Retardants in Glass Fiber-Reinforced Polyamide 66

Klitsch

Pfaendner²,

Fasel³

et al. 2022

Polymers

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In this study, the flame retardant effect of the Zn salt of 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (Zn-DOPOx), melamine polyphosphate (MPP) and their mixture was investigated towards the mode of action in glass fiber-reinforced polyamide 66 (PA 66 GF). The flammability was evaluated using UL 94 V and cone calorimetry. Influence on char formation was analyzed by SEM. Thermal decomposition of Zn-DOPOx and MPP was studied by TGA and ATR-FTIR. The release of gaseous PA 66 decomposition products was investigated using TGA-DTA-FTIR. Combining Zn-DOPOx and MPP leads to an improvement in flame retardancy, most pronounced for equal parts of weight. Mode of action changes significantly for Zn-DOPOx:MPP (1:1) compared to the sole components and a strong interaction between Zn-DOPOx and MPP is revealed, resulting in a more open char structure. Fuel dilution as well as less exothermic decomposition are essential for the mode of action of the combination. Through low HRR values and high CO/CO2 ratio during cone calorimetry measurements, a significant increase in gas phase activity was proven. Therefore, it is concluded that Zn-DOPOx:MPP (1:1) leads to a significant increase in flame retardancy through a combination of mode of actions in the gas and condensed phase resulting from the change in thermal stability.

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“…Chim., 72 (4), 2021, 13 In recent years, DOPO has attracted interest especially due to the multiple possibilities of structural diversification through functionalization. Thus, the active hydrogen of the DOPO heterocycle can react with various derivatives having groups deficient in electrons, leading to a wide range of phosphaphenanthrenic compounds [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Study on Thermal and Flame Retardant Properties of Phosphorus-containing Polyimides

Serbezeanu¹,

Vlad‐Bubulac²,

Hamciuc³

et al. 2021

Rev. Chim.

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The present study aimed to design macromolecular architectures having imide core in the main chain and bearing two 9,10-dihydro-oxa-10-phosphaphenanthrene-10-oxide heterocycles in the side chain of each structural units as a synergetic two components key factor to induce attractive flame retardant properties in the resulted materials. The synthesis pathway consisted in the classical polycondensation reaction strategy using a phosphorus-containing diamine synthesized in the laboratory and three commercial dianhydrides co-monomers. The chemical structure confirmation of the phosphorus-containing polyimides has been performed by means of FTIR and NMR spectroscopy. The thermal stability of the products was introspected through TGA analysis. The char yields measured at 900oC ranged between 35% and 54%. Using these parameters limiting oxygen index values were theoretically calculated. Also, the microscale combustion calorimetry measurements have been conducted, in order to investigate the combustion mechanism of the synthesized phosphorus-containing polyimides.

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Coordination Compounds of 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐Oxide (DOPO) Ligands: Extremely High Thermostability and Ligand Oxidation in the Solid State

Cited by 5 publications

References 31 publications

Effect of microencapsulation flame retardant on flame retardancy and mechanical properties of rigid polyurethane foams

Effect of microencapsulation flame retardant on flame retardancy and mechanical properties of rigid polyurethane foams

Mode of Action of Zn-DOPOx and Melamine Polyphosphate as Flame Retardants in Glass Fiber-Reinforced Polyamide 66

Study on Thermal and Flame Retardant Properties of Phosphorus-containing Polyimides

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