Polyhedral oligomeric silsesquioxane hybrided with <scp>DOPO</scp> and phenylboronic acid for flame‐retarded epoxy resin

Zeng, Birong; Zhou, Rui-Rui; Zheng, Xiaotong; Ye, Jianyu; Chen, Jinmei; Xu, Yiting; Yuan, Conghui; Dai, Lizong

doi:10.1002/pat.5262

Cited by 9 publications

(7 citation statements)

References 35 publications

(34 reference statements)

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“…Nuclear magnetic resonance hydrogen spectroscopy ( 1 H-NMR, Bruker AV500 M, DMSO as solvent) could identify the difference in the chemical environment of hydrogen atoms. In the result of DOPO (Figure 2b), the characteristic peak at 8.63 ppm should be attributed to P-H (Zeng et al ., 2021; Peng et al ., 2021; Li et al ., 2020). In the curve of HOMP (Figure 2b), the peak at 8.63 ppm vanished totally.…”

Section: Resultsmentioning

confidence: 95%

Synthesis of an efficient phosphorus and triazine ring-containing reactive flame retardant for epoxy resin

Meng

Wang

et al. 2023

MMMS

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PurposeIn order to find an appropriate method to synthesize a new high-efficiency flame retardant for epoxy resin.Design/methodology/approachIn this work, a flame retardant with heterocyclic groups, HOMP, was acquired after removing the obstacle from triazines which was not readily soluble. The molecular structure, thermal and flame retardant properties were fully characterized and analyzed. Also, the mechanism was researched through multi-methodologies. As well, the authors evaluated the effects of HOMP on mechanical properties.FindingsThe results suggested that HOMP helped extinguish the combustion of specimens and could reach an LOI value of 29.2% and the V0 level in the UL-94 test with a phosphorus content of only 0.6wt%. With respect to the mechanism, HOMP was a gas-phase flame retardant and helped generate a thicker carbon protective coating. However, for the mechanical properties, the addition of HOMP enhanced the compressibility, while the tensile strength decreased significantly.Originality/valueThe approach not only simplified the operations but also obtained HOMP with excellent flame retardant properties.

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Section: Resultsmentioning

confidence: 95%

Synthesis of an efficient phosphorus and triazine ring-containing reactive flame retardant for epoxy resin

Meng

Wang

et al. 2023

MMMS

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“…The new peak at 947 cm −1 was ascribed to Si-O-Zr bond in Figure 2g confirming the "corner-opening" and "corner-capping" reactions. The absorption peak of P-H around 2386 cm −1 from DOPO unit and the absorption peak of -NH 2 around 1607 cm −1 disappeared in the FTIR of Zr-POSS-bisDOPO, the peak at 903 cm −1 attributed to P-O-C bond, [14] and the signal of Si-O-Si were remained in Figure 2h, all of which indicated the successful "Kabachnik-Fields" reaction between DOPO and Zr-POSS. The target product of Zr-POSS-bisDOPO was synthesized successfully.…”

Section: Synthesis Of Zr-poss-bisdopomentioning

confidence: 93%

Zirconium‐Embedded Polyhedral Oligomeric Silsesquioxane Containing Phosphaphenanthrene‐Substituent Group Used as Flame Retardants for Epoxy Resin Composites

Zeng

et al. 2021

Macro Materials & Eng

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A zirconium hybrid polyhedral oligomeric silsesquioxane derivative (Zr-POSS-bisDOPO) is synthesized by the corner-capping and Kabachnik-Fields reactions. It is characterized by Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (NMR), and then used as a flame retardant in diglycidyl ether of bisphenol A (DGEBA) to endow epoxy resin (EP) with flame retardancy. The flame retardancy, thermal stability, and mechanical properties of the cured EP/Zr-POSS-bisDOPO composites are investigated. The results show that when Zr-POSS-bisDOPO is added by 5-7 wt%, the EP/Zr-POSS-bisDOPO composites pass the UL-94 V-0 rating test. In addition, they have a better flame-retardant effect than pure EP. The combination of Zr atom embedded in the Si-O cubic cage and the two phosphaphenanthrene substituent groups in one corner of cubic cage is expected to realize the Zr/Si/P ternary intramolecular hybrid synergistic effect and achieve the possibility of dispersing metal-POSS cages at a sub-micrometer-scale level into polymer matrix. It also proves that Zr-POSS-bisDOPO produces phosphorus-containing free radicals and terminates the chain reactions in gas phase. Meanwhile the Si-O-Si and Zr-O units are retained in the solid phase, which promote the char formation and enhance the flame retardancy. This kind of Zr-doped POSS will be helpful for developing the new metal-POSS hybrid flame-retardant and polymer composites.

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“…They are flexible and versatile, and with the exploration of new fields by researchers to extend the preparation of new solutions. 12,13 Unlike inorganic phosphorus flame retardants, organic phosphorus flameretardant molecules contain a large number of carbon atoms, and when these carbon atoms show different chemical states, the flame retardancy of the molecules under the same phosphorus content varies greatly, for example, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) is a commonly used synthesized intermediates of high-efficiency organic phosphorus flame retardants. 14,15 DOPO is a novel flame-retardant intermediate containing very active P H bonds, and the active P H bonds can react with aldehyde-ketone, 16,17 quinone, 18 C C, 19,20 and C N [21][22][23] unsaturated groups, and then react to produce many DOPO derivatives with high flameretardant efficiency.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of phosphaphenanthrene derivatives as flame retardants and their properties in epoxy resin composites

Qi,

Huan,

et al. 2024

J of Applied Polymer Sci

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In order to further improve the flame‐retardant properties of epoxy resins (EPs), two hydroxyl‐containing phospha‐phenanthrene derivatives, DOPO‐PHBA and DOPS‐PHBA, were prepared from the molecular structure design by using 9,10‐dihydro‐9‐oxa‐10‐phospha‐phenanthrene‐10‐oxide (DOPO), 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐sulfide (DOPS), and 4‐hydroxybenzaldehyde (PHBA) as the raw materials. These composites of DOPO‐PHBA/EP and DOPS‐PHBA/EP were prepared by melt blending. The results showed that UL‐94 V‐0 was achieved with an LOI of 31.9% when just 7.5% DOPS‐PHBA was added to EP, while a limited oxygen index of 35.2% was achieved with 10% DOPO‐PHBA/EP. Moreover, in comparison with 7.5% DOPO‐PHBA/EP, 7.5% DOPS‐PHBA/EP has the lower peak of heat release rates, total heat release values, and fire growth rate, demonstrating that the flame‐retardant DOPS‐PHBA is more effective at reducing heat release, enhancing the material's flame retardancy, and lessening the intensity of EP burning. The Thermogravimetric‐infraredspectrometry (TG‐IR) results showed that the phosphorus‐containing radicals generated by DOPS‐PHBA/EP pyrolysis trapped the free radicals, such as H˙, O˙, or HO˙, thus providing free radical quenching. Furthermore, combining the macro and micro Scanning electron microscopy (SEM) test results, DOPS‐PHBA/EP has a better char formation ability and a denser char layer, which can play a better role in heat and oxygen insulation.

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Polyhedral oligomeric silsesquioxane hybrided with DOPO and phenylboronic acid for flame‐retarded epoxy resin

Cited by 9 publications

References 35 publications

Synthesis of an efficient phosphorus and triazine ring-containing reactive flame retardant for epoxy resin

Synthesis of an efficient phosphorus and triazine ring-containing reactive flame retardant for epoxy resin

Zirconium‐Embedded Polyhedral Oligomeric Silsesquioxane Containing Phosphaphenanthrene‐Substituent Group Used as Flame Retardants for Epoxy Resin Composites

Synthesis of phosphaphenanthrene derivatives as flame retardants and their properties in epoxy resin composites

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