A Furan-based Phosphaphenanthrene-containing Derivative as a Highly Efficient Flame-retardant Agent for Epoxy Thermosets without Deteriorating Thermomechanical Performances

Hao-Xin Niu; Hong-Liang Ding; Jia-Li Huang; Xin Wang; Lei Song; Yuan Hu

doi:10.1007/s10118-022-2655-y

Your Location：

Home >

Browse articles >

A Furan-based Phosphaphenanthrene-containing Derivative as a Highly Efficient Flame-retardant Agent for Epoxy Thermosets without Deteriorating Thermomechanical Performances

RESEARCH ARTICLE | Updated：2022-03-23

- A Furan-based Phosphaphenanthrene-containing Derivative as a Highly Efficient Flame-retardant Agent for Epoxy Thermosets without Deteriorating Thermomechanical Performances
- Chinese Journal of Polymer Science Vol. 40, Issue 3, Pages: 233-240(2022)
- Affiliations：
  
  State Key Laboratory of Fire Science, University of Science and Technology of China, Hefei 230026, China
- Author bio：
  
  wxcmx@ustc.edu.cn
- Funds：
- DOI：10.1007/s10118-022-2655-y
  CLC：
- Received：21 September 2021，
  
  Revised：2021-10-15，
  
  Accepted：18 October 2021，
  
  Online First：11 January 2022，
  
  Published：01 March 2022
- Accepted：
Scan QR Code
Niu, H. X.; Ding, H. L.; Huang, J. L.; Wang, X.; Song, L.; Hu, Y. A furan-based phosphaphenanthrene-containing derivative as a highly efficient flame-retardant agent for epoxy thermosets without deteriorating thermomechanical performances. Chinese J. Polym. Sci. 2022, 40, 233–240

Hao-Xin Niu, Hong-Liang Ding, Jia-Li Huang, et al. A Furan-based Phosphaphenanthrene-containing Derivative as a Highly Efficient Flame-retardant Agent for Epoxy Thermosets without Deteriorating Thermomechanical Performances[J]. Chinese Journal of Polymer Science, 2022, 40(3): 233-240.
Niu, H. X.; Ding, H. L.; Huang, J. L.; Wang, X.; Song, L.; Hu, Y. A furan-based phosphaphenanthrene-containing derivative as a highly efficient flame-retardant agent for epoxy thermosets without deteriorating thermomechanical performances. Chinese J. Polym. Sci. 2022, 40, 233–240 DOI： 10.1007/s10118-022-2655-y.

Hao-Xin Niu, Hong-Liang Ding, Jia-Li Huang, et al. A Furan-based Phosphaphenanthrene-containing Derivative as a Highly Efficient Flame-retardant Agent for Epoxy Thermosets without Deteriorating Thermomechanical Performances[J]. Chinese Journal of Polymer Science, 2022, 40(3): 233-240. DOI： 10.1007/s10118-022-2655-y.

摘要

Abstract

In order to reduce greenhouse gas emissions

developing flame retardants from bio-based resources has aroused extensive interest in recent years. In this work

we utilized furfural (biomass) and 9

10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) to synthesize a bio-based co-curing agent (FGD) to combine with 4

4’-diaminodiphenyl methane (DDM) for obtaining a low-phosphorus loading flame-retardant epoxy thermosets. The introduction of FGD decreased the activation energy of the curing progress

enhanced the mechanical properties of the epoxy thermosets

and did not affect the glass transition temperature of the epoxy thermosets. EP-5.0 had a lower thermal degradation rate and a doubled char yield compared with EP-0. The phosphorus content of EP-5.0 was only 0.45 wt%

while EP-5.0 reached the UL-94 V-0 rating with a high LOI value of 32%. Compared with EP-0

the PHRR of EP-2.5 and EP-5.0 decreased by 22.3% and 31.3%

respectively. The SEM results showed that the addition of FGD made the char residues more uniform and denser

which could effectively prevent combustible volatiles from escaping from the degradation area to the flame area and isolate the heat transfer so that the epoxy thermosets had an excellent flame-retardant performance.

关键词

Keywords

references

Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J . R.; Murphy, R.; Templer, R.; Tschaplinski, T. The path forward for biofuels and biomaterials . Science , 2006 . 311 484 - 489 . DOI: 10.1126/science.1114736 http://doi.org/10.1126/science.1114736 .

Auvergne, R.; Caillol, S.; David, G.; Boutevin, B.; Pascault, J. P . Biobased thermosetting epoxy: present and future . Chem. Rev. , 2014 . 114 1082 - 1115 . DOI: 10.1021/cr3001274 http://doi.org/10.1021/cr3001274 .

Niu, H.; Nabipour, H.; Wang, X.; Song, L.; Hu, Y . Phosphorus-free vanillin-derived intrinsically flame-retardant epoxy thermoset with extremely low heat release rate and smoke emission . ACS Sustain. Chem. Eng. , 2021 . 9 5268 - 5277 . DOI: 10.1021/acssuschemeng.0c08302 http://doi.org/10.1021/acssuschemeng.0c08302 .

Wang, X.; Niu, H.; Guo, W.; Song, L.; Hu, Y . Cardanol as a versatile platform for fabrication of bio-based flame-retardant epoxy thermosets as DGEBA substitutes . Chem. Eng. J. , 2021 . 421 129738 DOI: 10.1016/j.cej.2021.129738 http://doi.org/10.1016/j.cej.2021.129738 .

Tong, X. L.; Ma, Y.; Li, Y. D . Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes . Appl. Catal. A-Gen. , 2010 . 385 1 - 13 . DOI: 10.1016/j.apcata.2010.06.049 http://doi.org/10.1016/j.apcata.2010.06.049 .

Bozell, J. J.; Petersen, G. R . Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited . Green Chem. , 2010 . 12 539 - 554 . DOI: 10.1039/b922014c http://doi.org/10.1039/b922014c .

Kamm, B.; Gruber, P. R.; Kamm, M . Biorefineries-industrial processes and products . Chemistry International—Newsmagazine for IUPAC , 2008 . 29 25 .

Zhang, Z.; Dong, K.; Zhao, Z . Efficient conversion of furfuryl alcohol into alkyl levulinates catalyzed by an organic-inorganic hybrid solid acid catalyst . ChemSusChem , 2011 . 4 112 - 118 . DOI: 10.1002/cssc.201000231 http://doi.org/10.1002/cssc.201000231 .

Lessard, J.; Morin, J. F.; Wehrung, J. F.; Magnin, D.; Chornet, E . High yield conversion of residual pentoses into furfural via zeolite catalysis and catalytic hydrogenation of furfural to 2-methylfuran . Top. Catal. , 2010 . 53 1231 - 1234 . DOI: 10.1007/s11244-010-9568-7 http://doi.org/10.1007/s11244-010-9568-7 .

Zheng, H. Y.; Zhu, Y. L.; Teng, B. T.; Bai, Z. Q.; Zhang, C. H.; Xiang, H. W.; Li, Y. W . Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran . J. Mol. Catal. A-Chem. , 2006 . 246 18 - 23 . DOI: 10.1016/j.molcata.2005.10.003 http://doi.org/10.1016/j.molcata.2005.10.003 .

Jin, F.L.; Li, X.; Park, S. J . Synthesis and application of epoxy resins: a review . J. Ind. Eng. Chem. , 2015 . 29 1 - 11 . DOI: 10.1016/j.jiec.2015.03.026 http://doi.org/10.1016/j.jiec.2015.03.026 .

Zhou, Y. F.; Chu, F. K.; Qiu, S. L.; Guo, W. W.; Zhang, S. H.; Xu, Z. M.; Hu, W. Z.; Hu, Y . Construction of graphite oxide modified black phosphorus through covalent linkage: an efficient strategy for smoke toxicity and fire hazard suppression of epoxy resin . J. Hazard. Mater. , 2020 . 399 123015 DOI: 10.1016/j.jhazmat.2020.123015 http://doi.org/10.1016/j.jhazmat.2020.123015 .

Gao, C.; Yu, T.; Sun, J.; Gu, X.; Li, H.; Mu, C.; Zhang, S . A phosphate covalent organic framework: synthesis and applications in epoxy resin with outstanding fire performance and mechanical properties . Polym. Degrad. Stabil. , 2021 . 190 109613 DOI: 10.1016/j.polymdegradstab.2021.109613 http://doi.org/10.1016/j.polymdegradstab.2021.109613 .

Wang, M.; Wu, Q.; Feng, Z.; Gu, X.; Li, H.; Sun, J.; Fei, B.; Zhang, S . Surface modification of cellulose microcrystalline with aluminate coupling agent and its effects on flame retardant and mechanical properties of epoxy resin . Fiber Polym. , 2020 . 21 2344 - 2352 . DOI: 10.1007/s12221-020-1353-z http://doi.org/10.1007/s12221-020-1353-z .

Chen, L.; Wang, Y. Z . A review on flame retardant technology in China. Part 1: development of flame retardants . Polym. Adv. Technol. , 2010 . 21 1 - 26 . .

Laoutid, F.; Bonnaud, L.; Alexandre, M.; Lopez-Cuesta, J. M.; Dubois, P . New prospects in flame retardant polymer materials: from fundamentals to nanocomposites . Mater. Sci. Eng. R , 2009 . 63 100 - 125 . DOI: 10.1016/j.mser.2008.09.002 http://doi.org/10.1016/j.mser.2008.09.002 .

Braun, U.; Schartel, B.; Fichera, M. A.; Jaeger, C . Flame retardancy mechanisms of aluminium phosphinate in combination with melamine polyphosphate and zinc borate in glass-fibre reinforced polyamide 6,6 . Polym. Degrad. Stabil. , 2007 . 92 1528 - 1545 . DOI: 10.1016/j.polymdegradstab.2007.05.007 http://doi.org/10.1016/j.polymdegradstab.2007.05.007 .

Martin, C.; Ronda, J. C.; Cadiz, V . Boron-containing novolac resins as flame retardant materials . Polym. Degrad. Stabil. , 2006 . 91 747 - 754 . DOI: 10.1016/j.polymdegradstab.2005.05.025 http://doi.org/10.1016/j.polymdegradstab.2005.05.025 .

Lu, S. Y.; Hamerton, I . Recent developments in the chemistry of halogen-free flame retardant polymers . Prog. Polym. Sci. , 2002 . 27 1661 - 1712 . DOI: 10.1016/S0079-6700(02)00018-7 http://doi.org/10.1016/S0079-6700(02)00018-7 .

van der Veen, I.; de Boer, J . Phosphorus flame retardants: properties, production, environmental occurrence, toxicity and analysis . Chemosphere , 2012 . 88 1119 - 1153 . DOI: 10.1016/j.chemosphere.2012.03.067 http://doi.org/10.1016/j.chemosphere.2012.03.067 .

Wang, X.; Hu, Y.; Song, L.; Xing, W.; Lu, H.; Lv, P.; Jie, G . Flame retardancy and thermal degradation mechanism of epoxy resin composites based on a DOPO substituted organophosphorus oligomer . Polymer , 2010 . 51 2435 - 2445 . DOI: 10.1016/j.polymer.2010.03.053 http://doi.org/10.1016/j.polymer.2010.03.053 .

Levchik, S. V.; Weil, E. D . A review of recent progress in phosphorus-based flame retardants . J. Fire Sci. , 2006 . 24 345 - 364 . DOI: 10.1177/0734904106068426 http://doi.org/10.1177/0734904106068426 .

Qian, X. D.; Song, L.; Yuan, B. H.; Yu, B.; Shi, Y. Q.; Hu, Y.; Yuen, R. K. K . Organic/inorganic flame retardants containing phosphorus, nitrogen and silicon: preparation and their performance on the flame retardancy of epoxy resins as a novel intumescent flame retardant system . Mater. Chem. Phys. , 2014 . 143 1243 - 1252 . DOI: 10.1016/j.matchemphys.2013.11.029 http://doi.org/10.1016/j.matchemphys.2013.11.029 .

Dasari, A.; Yu, Z. Z.; Cai, G. P.; Mai, Y. W . Recent developments in the fire retardancy of polymeric materials . Prog. Polym. Sci. , 2013 . 38 1357 - 1387 . DOI: 10.1016/j.progpolymsci.2013.06.006 http://doi.org/10.1016/j.progpolymsci.2013.06.006 .

Covaci, A.; Harrad, S.; Abdallah, M. A. E.; Ali, N.; Law, R. J.; Herzke, D.; de Wit, C. A . Novel brominated flame retardants: a review of their analysis, environmental fate and behaviour . Environ. Int. , 2011 . 37 532 - 556 . DOI: 10.1016/j.envint.2010.11.007 http://doi.org/10.1016/j.envint.2010.11.007 .

Carja, I. D.; Serbezeanu, D.; Vlad-Bubulac, T.; Hamciuc, C.; Coroaba, A.; Lisa, G.; Lopez, C. G.; Soriano, M. F.; Perez, V. F.; Sanchez, M. D. R . A straightforward, eco-friendly and cost-effective approach towards flame retardant epoxy resins . J. Mater. Chem. A , 2014 . 2 16230 - 16241 . DOI: 10.1039/C4TA03197K http://doi.org/10.1039/C4TA03197K .

Perret, B.; Schartel, B.; Stoss, K.; Ciesielski, M.; Diederichs, J.; Doring, M.; Kramer, J.; Altstadt, V . Novel DOPO-based flame retardants in high-performance carbon fibre epoxy composites for aviation . Eur. Polym. J. , 2011 . 47 1081 - 1089 . DOI: 10.1016/j.eurpolymj.2011.02.008 http://doi.org/10.1016/j.eurpolymj.2011.02.008 .

Shieh, J. Y.; Wang, C. S . Synthesis of novel flame retardant epoxy hardeners and properties of cured products . Polymer , 2001 . 42 7617 - 7625 . DOI: 10.1016/S0032-3861(01)00257-9 http://doi.org/10.1016/S0032-3861(01)00257-9 .

Natarajan, M.; Murugavel, S. C . Cure kinetics of bio-based epoxy resin developed from epoxidized cardanol-formaldehyde and diglycidyl ether of bisphenol-A networks . J. Therm. Anal. Calorim. , 2016 . 125 387 - 396 . DOI: 10.1007/s10973-016-5417-7 http://doi.org/10.1007/s10973-016-5417-7 .

Pan, X.; Sengupta, P.; Webster, D. C . High biobased content epoxy-anhydride thermosets from epoxidized sucrose esters of fatty acids . Biomacromolecules , 2011 . 12 2416 - 2428 . DOI: 10.1021/bm200549c http://doi.org/10.1021/bm200549c .

Xiao, Y. L.; Mu, X. W.; Wang, B. B.; Hu, W. Z.; Wang, J . L.; Zhou, F.; Ma, C.; Hu, Y.; Song, L. A novel phosphorous-containing polymeric compatibilizer: effective reinforcement and flame retardancy in glass fiber reinforced polyamide 6 composites . Compos. Part B-Eng. , 2021 . 205 108536 DOI: 10.1016/j.compositesb.2020.108536 http://doi.org/10.1016/j.compositesb.2020.108536 .

Views

195

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Sliding Dynamics of Ring Chain on a Rod-Coil Block Copolymer in Rotaxane

Tunable Circularly Polarized Luminescence of Helical Poly(phenylacetylene)s via Side-chain-to-Backbone Förster Resonance Energy Transfer

Advances in Polymer-based Circularly Polarized Luminescent Materials

Silk Sericin-inspired Poly-β-homoserine for Protein Protection

Related Author

No data

Related Institution

No data

⁰