Imide-DOPO derivative endows epoxy resin with excellent flame retardancy and fluorescence without losing glass transition temperature

He, Lihua; Chen, Tao; Zhang, Yi; Hu, Lianrui; Wang, Ting; Han, Rui; He, Jialin; Luo, Wei; Liu, Zhiguo; Deng, Jiao-Yu; Chen, Mingjun

doi:10.1016/j.compositesb.2021.109553

Cited by 65 publications

(22 citation statements)

References 51 publications

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“…DOPO and its derivatives with voluminous phosphaphenanthrene groups in their structures have appeared as a solution to the development of polymers with increased solubility and thermal stability due to the presence of the P–O–C bond [ 10 , 11 , 12 ]. Furthermore, interesting optical properties have been reported for such DOPO-containing high performance polymers [ 13 , 14 , 15 , 16 ]. To our knowledge, DOPO-containing polyimides have rarely been developed into flexible thin films as a consequence of the bulky nature of DOPO, which may prevent molecular packing [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

“…Aromatic polyimide derivatives containing –CH 3 or –CF 3 groups have effectively higher solubility, free volume, inherent fire-resistant properties, increased thermal stability, and high polarizability, which are essential for industrial applications. Recently, He et al [ 16 ] synthesized an imide-DOPO derivative with excellent flame retardancy and aggregation-induced emission enhancement, simultaneously exhibiting fluorescence properties without losing their glass transition temperature. In another study, Jiang et al [ 23 ] studied the effects of cardanol-based co-curing agents with different phosphorus structures on the mechanical and flame-retardant properties of bismaleimide resin.…”

Section: Introductionmentioning

confidence: 99%

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Optical and Flame-Retardant Properties of a Series of Polyimides Containing Side Chained Bulky Phosphaphenanthrene Units

Homocianu¹,

Serbezeanu²,

Lisă

et al. 2022

IJMS

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Among the multitude of polymers with carbon-based macromolecular architectures that easily ignite in certain applications where short circuits may occur, polyimide has evolved as a class of polymers with high thermal stability while exhibiting intrinsic flame retardancy at elevated temperatures via a char-forming mechanism. However, high amounts of aromatic rings in the macromolecular backbone are required for these results, which may affect other properties such as film-forming capacity or mechanical properties; thus, much work has been done to structurally derivatize or make hybrid polyimide systems. In this respect, flexible polyimide films (PI(1–4)) containing bulky 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) units have been developed starting from commercial dianhydrides and an aromatic diamine containing two side chain bulky DOPO groups. The chemical structure of PI(1–4)) was characterized by 1H NMR, 13C NMR and 31P NMR spectroscopy. The optical properties, including absorption and luminescence spectra of these polymers, were analyzed. All polyimides containing DOPO derivatives emitted blue light with an emission maxima in the range of 340–445 nm, in solvents such as N,N-dimethylformamide, N-methyl-2-pyrrolidone, chloroform, and N,N-dimethylacetamide, while green light emission (λem = 487 nm for PI-4) was evidenced in a thin-film state. The thermal decomposition mechanism and flame-retardant behavior of the resulting materials were investigated by pyrolysis-gas-chromatography spectrometry (Py-GC), scanning electron microscopy (SEM), EDX maps and FTIR spectroscopy. The residues resulting from the TGA experiments were examined by SEM microscopy images and FTIR spectra to understand the pyrolysis mechanism.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Optical and Flame-Retardant Properties of a Series of Polyimides Containing Side Chained Bulky Phosphaphenanthrene Units

Homocianu¹,

Serbezeanu²,

Lisă

et al. 2022

IJMS

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“…[23][24][25] For instance, He et al synthesized an imine DOPO derivative, called BMP, and applied it to EP. 26 When BMP content was 10%, EP/BMP achieved UL-94V-0 and high LOI values of 35%. Meantime, the T g of EP/BMP was not reduced due to the spatial hindrance and intermolecular interactions (π-π stacking) of BMP, which caused only slight damage to tensile and impact strength.…”

mentioning

confidence: 93%

A novel epoxy resin system containing bismaleimide and DOPO‐based flame retardant with excellent flame retardancy and toughness

Liu

Zhang

Jia

et al. 2023

J of Applied Polymer Sci

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Abstract9,10‐dihydro‐9‐oxo‐10‐phosphaphenanthrene‐10‐oxide (DOPO) and special tetra functional epoxy resin (EP) AG‐601 were combined to synthesize a reactive flame retardant (FREP) and then incorporated into EP, obtaining the flame retardant material EP/FREP. To achieve EPs with higher flame retardancy and mechanical properties, a new intrinsically flame retardant EP system named EP/FRDM was produced by modifying EP/FREP with high thermal resistance bismaleimide (BDM). In the presence of a distinct FRDM structure comprising phosphaphenanthrene/nitrogen, the EP possessed superior flame retardancy and impact toughness. The curing process of EP/FRDM was investigated using Real‐Time Fourier‐transform Infrared. In terms of fire performance, the limiting oxygen index of the EP/FRDM‐3 was raised from 31.4% to 38.2%, and the vertical burning rating was improved after BDM was added to the EP/FREP system. It was discovered that EP/FRDM exhibited a classic two‐phase flame retardant influence by analyzing the residual carbon morphology and pyrolysis behavior. Simultaneously, the glass transition temperature (Tg) of EP/FRDM remained essentially stable, and the char residue yield rose markedly, which indicated that the system had outstanding thermal stability, according to the results of the dynamic mechanical analysis and thermogravimetric analysis tests. Notably, the EP/FRDM experienced an internal chain expansion reaction when BDM was added, giving flame retardant materials excellent flexural and impact strengths and promising future application opportunities.

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“…Epoxy resin (EP), one of the most used thermosets, has been an indispensable basic material for high-end manufacturing industries such as 5G communications and rail transit, thanks to its excellent comprehensive performances including thermal stability, mechanic strength, chemical resistance, and transparency. However, like many other petroleum-based polymer matrices, the EP also suffers from intrinsic flammability with serious melt-dripping because of the organic characteristics, which restricts the broad application in the fields requiring harsh fire safety [ 1 , 2 ]. It is well-known that fires as one of common accidents threaten seriously human security and the environment and bring about annual costs of tens of billions of dollars globally [ 3 ].…”

Section: Introductionmentioning

confidence: 99%

A Nitrogen-Rich DOPO-Based Derivate for Increasing Fire Resistance of Epoxy Resin with Comparable Transparency

Cai

et al. 2023

Materials

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To endow synergistically epoxy resin (EP) with excellent fire resistance and high optical transparency, a nitrogen-rich DOPO-based derivate (named as FATP) was synthesized and incorporated into EP. It showed that the incorporation of the FATP reduced the fire hazard of the EP, as demonstrated by the fact that the EP/4% FATP blends gained a UL-94 V-0 rating and an LOI value of 35%, with the lowest values of the THR (86.7 MJ/m2), the PHRR (1059.3 kW/m2), and the TSP (89.6 MJ/m2). The presence of the FATP also reduced the thermal stability and the crosslinking density whilst improving the curing reaction and the storage modulus of the EP/FATP blends. The TG-FTIR spectra showed that •HPO/•PO free radicals and some nonflammable gases (HN3 and NH3) were produced during the pyrolysis, and the characterization (SEM, Raman spectroscopy, and XPS) of char residues confirmed that the FATP facilitated the formation of continuous and compact carbon layers of greater graphitization degree. It was thus concluded that the FATP played the flame-retardant roles in both the gas and condensed phases. Furthermore, the FREPs kept almost identical transparency as the pristine EP, and mechanical properties were also slightly enhanced. The FREPs presented in this work show promising applications in the fields of advanced optical technology.

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Imide-DOPO derivative endows epoxy resin with excellent flame retardancy and fluorescence without losing glass transition temperature

Cited by 65 publications

References 51 publications

Optical and Flame-Retardant Properties of a Series of Polyimides Containing Side Chained Bulky Phosphaphenanthrene Units

Optical and Flame-Retardant Properties of a Series of Polyimides Containing Side Chained Bulky Phosphaphenanthrene Units

A novel epoxy resin system containing bismaleimide and DOPO‐based flame retardant with excellent flame retardancy and toughness

A Nitrogen-Rich DOPO-Based Derivate for Increasing Fire Resistance of Epoxy Resin with Comparable Transparency

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