Improved flame retardancy by synergy between cyclotetrasiloxane and phosphaphenanthrene/triazine compounds in epoxy thermoset

Qiu, Yong; Wachtendorf, Volker; Klack, Patrick; Qian, Lijun; Liu, Zhen; Schartel, Bernhard

doi:10.1002/pi.5466

Cited by 25 publications

(14 citation statements)

References 44 publications

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“…However, halogenated retardants can produce lots of smoke and toxic gases when they are burning, which have many negative effects on the environment and human . In recent years, researchers have developed many types of halogen‐free flame retardants, such as boron, phosphorus, silicon, sulfur, graphene and nitrogen‐containing compounds . Among them, phosphorus‐containing flame retardant is the most widely used because of its good gaseous phase effect .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of DOPO‐based pyrazine derivative and its effect on flame retardancy and thermal stability of epoxy resin

Tang

Zhu

Chen

et al. 2019

Polymers for Advanced Techs

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A novel DOPO-based pyrazine derivative 6-((2-hydroxyphenyl)(pyrazin-2-ylamino) methyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide (DHBAP) was triumphantly synthesized by a two-step addition reaction using 2-aminopyrazine, 2hydroxybenzaldehyde and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) as reactants, and characterized by Fourier-transform infrared (FTIR), 31 P nuclear magnetic resonance (NMR) and 1 H NMR. Afterwards, the addition type flame retardant (DHBAP) was utilized to modify epoxy resin (EP) by blending method.When the content of DHBAP in neat EP was 8 wt%, it reached to the V-0 rating and the limited oxygen index (LOI) value up to 34.0%. Furthermore, according to the cone calorimeter (CC) test results, the heat release rate (HRR), total heat release (THR), smoke produce rate (SPR) and total smoke production (TSP) of EP/8% DHBAP decreased by 26.3%, 21.3%, 37.0% and 60.9% when compared with neat EP, respectively, indicating that DHBAP had good inhibition on heat and smoke releases. Eventually, the flame-retardant mechanism of DHBAP was further explored by X-ray photoelectron spectroscopy (XPS), Raman spectroscopy, and pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). The results showed that DHBAP had good flame-retardant activity in the gasous-condensed two phases. KEYWORDSDOPO, epoxy resin, flame retardancy, mechanism, pyrazine 1 | INTRODUCTION Epoxy resin (EP) has extensive applications in automotive, defense, aerospace, and electrical industry because of good mechanical properties and chemical stability. 1-4 Unfortunately, EP is a flammable material, which limits its further application. Consequently, it is an important task to impart flame retardancy of EPs.So as to improve its flame-retardant properties, the combination of flame retardant with EP has been recognized to be an effective way.Traditionally, halogen-containing flame retardants are widely utilized because of their gaseous phase activity. 5-7 However, halogenated retardants can produce lots of smoke and toxic gases when they are burning, which have many negative effects on the environment and human. 8,9 In recent years, researchers have developed many types of halogen-free flame retardants, such as boron, 10-13 phosphorus, [14][15][16][17][18][19] silicon, 20-22 sulfur, 23-26 graphene 27,28 and nitrogen-containing compounds. 29-31 Among them, phosphorus-containing flame retardant is the most widely used because of its good gaseous phase effect. 15,[32][33][34] Currently, DOPO and its derivatives are widely concerned for their excellent flame-retardant efficiency. Since DOPO has an active P-H group, it is easy to cleave to form H· and DOPO radicals, and can be used as an antioxidant by quenching oxygen radicals. 35,36 Due to the active group in DOPO, DOPO can react with compounds containg unsaturated bonds, such as schiff base, carbon carbon double bond and ketone, leading to various approaches to synthesize new DOPO derivatives. 37 Schäfer et al added DOPO to the EP, and the sample passed the V-0 rating, whereas the phosp...

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Section: Introductionmentioning

confidence: 99%

Synthesis of DOPO‐based pyrazine derivative and its effect on flame retardancy and thermal stability of epoxy resin

Tang

Zhu

Chen

et al. 2019

Polymers for Advanced Techs

View full text Add to dashboard Cite

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“…Epoxy resins play an indispensable role in almost every industry including aerospace, electric information, insulation, new energy and many other areas owing to their excellent adhesion, chemical resistance and mechanical and dielectric properties. They take about 70% of the market share of thermosetting resins and thus belong to one of the most important species of petrochemical products.…”

Section: Introductionmentioning

confidence: 99%

Biobased epoxy resin derived from eugenol with excellent integrated performance and high renewable carbon content

Miao

Yuan

Guan

et al. 2018

Polymer International

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Developing biobased epoxy resin with high renewable carbon content and outstanding integrated performance is beneficial for both sustainable development and applications in cutting-edge fields. Herein, a biobased epoxy monomer (TEUP-EP) with high renewable carbon content (100%) was synthesized from renewable eugenol with a sustainable process; TEUP-EP was then blended with 4,4 ′ -diaminodiphenylmethane (DDM) to develop a new biobased epoxy resin (TEUP-EP/DDM). The integrated performance of TEUP-EP/DDM resin was studied and compared with that of petroleum-based diglycidyl ether of bisphenol A (DGEBA)/DDM resin. Compared with DGEBA/DDM resin, TEUP-EP/DDM resin has much better integrated performance and not only exhibits a glass transition temperature about 26 ∘ C higher and a 24.4% or 57% increased flexural strength or modulus, but also shows outstanding flame retardancy. Specifically, the limiting oxygen index increases from 26.5% to 31.4% and the UL-94 grade improves from no rating to the V-0 level; moreover, the peak heat release rate and total heat release decreased by 63.1% and 57.4%, respectively. All these results fully prove that TEUP-EP/DDM is a novel biobased high performance epoxy resin. The mechanism behind these attractive integrated performances is discussed intensively.

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“…That showed the inhibition effect of TGD on the combustion behavior of epoxy thermoset samples. TGD, which had been confirmed flame retardancy in epoxy thermosets, has better gas‐phase flame retardant effect than condensed‐phase one. In contrast, the results of 3%OMMT/EP sample demonstrated that the addition of OMMT significantly promote the progression of combustion, because of the higher pk‐HRR and av‐EHC values.…”

Section: Resultsmentioning

confidence: 89%

“…The introduction of OMMT caused negative influence for three flame retardant effects aforementioned on 3%OMMT/EP. Differently, because of the stronger flame retardant effect of TGD in gas phase, 3%TGD/EP sample showed a superior flame inhibition effect, but almost no charring effect and worse barrier and protective effect. Comparing with the two samples with only one additive mentioned above, 0.5%OMMT/2.5%TGD/EP sample exhibited the most positive results in all three main effects of flame retardancy, indicating a synergistic effect between OMMT and TGD.…”

Section: Resultsmentioning

confidence: 90%

Strengthen flame retardancy of epoxy thermoset by montmorillonite particles adhering phosphorus‐containing fragments

Liu

Qiu

Qian

et al. 2019

J of Applied Polymer Sci

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Phosphaphenanthrene derivative tri-(3-DOPO-2-hydroxypropan-1-yl)-1,3,5-triazine-2,4,6-trione (TGD) and organo-modified montmorillonite (OMMT) were jointly introduced into the diglycidyl ether of bisphenol A cured by 4,4-diamino-diphenylmethane (EP) to investigate their flame retardant behaviors. With only addition of 0.5%OMMT and 2.5%TGD, epoxy thermoset achieved a limiting oxygen index value of 33.7% and passed UL 94 V-0 rating test. Compared with the combustion behaviors of 3%OMMT/EP and 3%TGD/EP, an obvious synergistic flame retardant effect between OMMT and TGD can be concluded in OMMT/TGD/EP. Meanwhile, the FTIR spectra of gas-phase and condensed-phase products further proved this synergistic effect working in a physical way. On one hand, the co-existence of hydroxyl-containing TGD enabled montmorillonite (MMT) particles to filtrate and adhere more smoke fragments. On the other hand, the co-action of MMT help the polar phosphorus-containing fragments from TGD better strengthened char layer, enhancing the barrier and protective effect of residue. The synergistic flame retardant effect from OMMT/TGD system endowed themselves with higher flame retardant efficiency, and epoxy thermoset with better flame retardant performance.

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Improved flame retardancy by synergy between cyclotetrasiloxane and phosphaphenanthrene/triazine compounds in epoxy thermoset

Cited by 25 publications

References 44 publications

Synthesis of DOPO‐based pyrazine derivative and its effect on flame retardancy and thermal stability of epoxy resin

Synthesis of DOPO‐based pyrazine derivative and its effect on flame retardancy and thermal stability of epoxy resin

Biobased epoxy resin derived from eugenol with excellent integrated performance and high renewable carbon content

Strengthen flame retardancy of epoxy thermoset by montmorillonite particles adhering phosphorus‐containing fragments

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