A hyperbranched P/N/B-containing oligomer as multifunctional flame retardant for epoxy resins

Composites Part B: Engineering - Tập 234 - Trang 109701 - 2022
Siqi Huo1,2, Ting Sai1,2, Shiya Ran2, Zhenghong Guo2, Zhengping Fang2, Pingan Song3,4, Hao Wang3
1MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China
2Laboratory of Polymer Materials and Engineering, NingboTech University, Ningbo 315100, China
3Center for Future Materials, University of Southern Queensland, Springfield Central 4300, Australia
4School of Agriculture and Environmental Science, University of Southern Queensland, Springfield Central 4300, Australia

Tài liệu tham khảo

Yang, 2021, A nano-TiO2/regenerated cellulose biohybrid enables simultaneously improved strength and toughness of solid epoxy resins, Compos Sci Technol, 212, 108884, 10.1016/j.compscitech.2021.108884 Xu, 2019, Recyclable thermoset hyperbranched polymers containing reversible hexahydro-s-triazine, Nat Sustain, 3, 29, 10.1038/s41893-019-0444-6 Liu, 2022, A reactive copper-organophosphate-MXene heterostructure enabled antibacterial, self-extinguishing and mechanically robust polymer nanocomposites, Chem Eng J, 430, 132712, 10.1016/j.cej.2021.132712 Salasinska, 2020, Synergistic effect between histidine phosphate complex and hazelnut shell for flammability reduction of low-smoke emission epoxy resin, Polym Degrad Stabil, 181, 109292, 10.1016/j.polymdegradstab.2020.109292 Fang, 2020, A bio-based ionic complex with different oxidation states of phosphorus for reducing flammability and smoke release of epoxy resins, Compos Commun, 17, 104, 10.1016/j.coco.2019.11.011 Ma, 2011, Flame retarded polymer nanocomposites: development, trend and future perspective, Sci China Chem, 54, 302, 10.1007/s11426-010-4196-4 Seraji, 2022, Fire-retardant unsaturated polyester thermosets: the state-of-the-art, challenges and opportunities, Chem Eng J, 430, 132785, 10.1016/j.cej.2021.132785 Sai, 2021, Sulfonated block ionomers enable transparent, fire-resistant, tough yet strong polycarbonate, Chem Eng J, 133264 Krishnadevi, 2015, Development of halogen-free flame retardant phosphazene and rice husk ash incorporated benzoxazine blended epoxy composites for microelectronic applications, New J Chem, 39, 6555, 10.1039/C5NJ00364D Seraji, 2021, Phosphazene as an effective flame retardant for rapid curing epoxy resins, React Funct Polym, 164, 104910, 10.1016/j.reactfunctpolym.2021.104910 Liu, 2021, Functionalizing MXene towards highly stretchable, ultra tough, fatigue- and fire-resistant polymer nanocomposites, Chem Eng J, 424, 130338, 10.1016/j.cej.2021.130338 Zhao, 2021, Curing mechanism, thermal and ablative properties of hexa-(4-amino-phenoxy) cyclotriphosphazene/benzoxazine blends, Compos B Eng, 216, 108838, 10.1016/j.compositesb.2021.108838 Jin, 2016, Functionalizing graphene decorated with phosphorus-nitrogen containing dendrimer for high-performance polymer nanocomposites, Compos Part A Appl Sci Manuf, 86, 9, 10.1016/j.compositesa.2016.03.030 Ye, 2021, One-step and green synthesis of a bio-based high-efficiency flame retardant for poly (lactic acid), Polym Degrad Stabil, 192, 109696, 10.1016/j.polymdegradstab.2021.109696 Wang, 2021, A novel DOPO-based flame retardant containing benzimidazolone structure with high charring ability towards low flammability and smoke epoxy resins, Polym Degrad Stabil, 183, 109426, 10.1016/j.polymdegradstab.2020.109426 Huo, 2020, A liquid phosphaphenanthrene-derived imidazole for improved flame retardancy and smoke suppression of epoxy resin, ACS Appl Polym Mater, 2, 3566, 10.1021/acsapm.0c00577 Schmidt, 2018, Novel organophosphorus flame retardants and their synergistic application in novolac epoxy resin, Polym Degrad Stabil, 158, 190, 10.1016/j.polymdegradstab.2018.09.001 Rao, 2021, High strength, low flammability, and smoke suppression for epoxy thermoset enabled by a low-loading phosphorus-nitrogen-silicon compound, Compos B Eng, 211, 108640, 10.1016/j.compositesb.2021.108640 Jian, 2019, Organophosphorus heteroaromatic compound towards mechanically reinforced and low-flammability epoxy resin, Compos B Eng, 168, 458, 10.1016/j.compositesb.2019.03.052 Jian, 2020, Rationally designed zinc borate@ZIF-8 core-shell nanorods for curing epoxy resins along with low flammability and high mechanical property, Compos B Eng, 200, 108349, 10.1016/j.compositesb.2020.108349 Ma, 2022, A lava-inspired micro/nano-structured ceramifiable organic-inorganic hybrid fire-extinguishing coating, Matter, 10.1016/j.matt.2021.12.009 Zhang, 2019, Facile construction of one-component intrinsic flame-retardant epoxy resin system with fast curing ability using imidazole-blocked bismaleimide, Compos B Eng, 177, 107380, 10.1016/j.compositesb.2019.107380 Huo, 2020, Thermal properties and flame retardancy of an intumescent flame-retarded epoxy system containing phosphaphenanthrene, triazine-trione and piperidine, J Therm Anal Calorim, 139, 1099, 10.1007/s10973-019-08467-3 Yang, 2017, Preparation and investigation of flame-retardant epoxy resin modified with a novel halogen-free flame retardant containing phosphaphenanthrene, triazine-trione, and organoboron units, J Appl Polym Sci, 134, 45291, 10.1002/app.45291 Yang, 2016, Synthesis of a novel flame retardant containing phosphorus, nitrogen and boron and its application in flame-retardant epoxy resin, Polym Degrad Stabil, 133, 358, 10.1016/j.polymdegradstab.2016.09.023 Tang, 2019, A novel nitrogen, phosphorus, and boron ionic pair compound toward fire safety and mechanical enhancement effect for epoxy resin, Polym Adv Technol, 31, 885, 10.1002/pat.4823 Wang, 2021, High performance epoxy resin composites modified with multifunctional thiophene/phosphaphenanthrene-based flame retardant: excellent flame retardance, strong mechanical property and high transparency, Compos B Eng, 227, 109392, 10.1016/j.compositesb.2021.109392 Ma, 2020, The versatility of hyperbranched epoxy resins containing hexahydro-s-triazine on diglycidyl ether of bisphenol-A composites, Compos B Eng, 196, 108109, 10.1016/j.compositesb.2020.108109 Battig, 2021, Hyperbranched rigid aromatic phosphorus-containing flame retardants for epoxy resins, Macromol Mater Eng, 306, 2000731, 10.1002/mame.202000731 Ye, 2021, A novel hyperbranched phosphorus-boron polymer for transparent, flame-retardant, smoke-suppressive, robust yet tough epoxy resins, Compos B Eng, 207, 109395, 10.1016/j.compositesb.2021.109395 Ma, 2021, Closed-loop recycling of both resin and fiber from high-performance thermoset epoxy/carbon fiber composites, ACS Macro Lett, 10, 1113, 10.1021/acsmacrolett.1c00437 Ma, 2017, Economical and environment-friendly synthesis of a novel hyperbranched poly(aminomethylphosphine oxide-amine) as co-curing agent for simultaneous improvement of fire safety, glass transition temperature and toughness of epoxy resins, Chem Eng J, 322, 618, 10.1016/j.cej.2017.04.070 Ma, 2018, Facile synthesis of a novel hyperbranched poly(urethane-phosphine oxide) as an effective modifier for epoxy resin, Polym Degrad Stabil, 154, 157, 10.1016/j.polymdegradstab.2018.05.021 Teng, 2022, Hyperbranched flame retardant for epoxy resin modification: simultaneously improved flame retardancy, toughness and strength as well as glass transition temperature, Chem Eng J, 428, 131226, 10.1016/j.cej.2021.131226 Chi, 2020, A DOPO-based phosphorus-nitrogen flame retardant bio-based epoxy resin from diphenolic acid: synthesis, flame-retardant behavior and mechanism, Polym Degrad Stabil, 176, 109151, 10.1016/j.polymdegradstab.2020.109151 Alhwaige, 2015, Interactions, morphology and thermal stability of graphene-oxide reinforced polymer aerogels derived from star-like telechelic aldehyde-terminal benzoxazine resin, RSC Adv, 5, 92719, 10.1039/C5RA16188F Parveen, 2015, Fabrication of highly durable hydrophobic PBZ/SiO2 surfaces, RSC Adv, 5, 43601, 10.1039/C5RA06413A Liang, 2015, Synthesis of novel intumescent flame retardant containing phosphorus, nitrogen and boron and its application in polyethylene, Polym Bull, 72, 2967, 10.1007/s00289-015-1447-8 Halajnia, 2013, Adsorption–desorption characteristics of nitrate, phosphate and sulfate on Mg–Al layered double hydroxide, Appl Clay Sci, 80–81, 305, 10.1016/j.clay.2013.05.002 Qiu, 2018, Toughening effect and flame-retardant behaviors of phosphaphenanthrene/phenylsiloxane bigroup macromolecules in epoxy thermoset, Macromolecules, 51, 9992, 10.1021/acs.macromol.8b02090 Li, 2020, Effects of low-load boron/silicon-based graphene oxide on combustion and thermal degradation of flame-retardant unsaturated polyester resin, Macromol Mater Eng, 305, 2000454, 10.1002/mame.202000454 Liu, 2022, Flame-Retardant multifunctional epoxy resin with high performances, Chem Eng J, 427, 132031, 10.1016/j.cej.2021.132031 Calabrese, 2003, Effect of CTBN rubber inclusions on the curing kinetic of DGEBA–DGEBF epoxy resin, Eur Polym J, 39, 1355, 10.1016/S0014-3057(02)00390-7 Gao, 2013, Synthesis and properties of transparent cycloaliphatic epoxy–silicone resins for opto-electronic devices packaging, Opt Mater, 35, 567, 10.1016/j.optmat.2012.10.023 Huo, 2022, Flame-retardant, transparent, mechanically-strong and tough epoxy resin enabled by high-efficiency multifunctional boron-based polyphosphonamide, Chem Eng J, 427, 131578, 10.1016/j.cej.2021.131578 Pourchet, 2019, New reactive isoeugenol based phosphate flame retardant: toward green epoxy resins, ACS Sustainable Chem Eng, 7, 14074, 10.1021/acssuschemeng.9b02629 Lou, 2021, Fully biobased surface-functionalized microcrystalline cellulose via green self-assembly toward fire-retardant, strong, and tough epoxy biocomposites, ACS Sustainable Chem Eng, 9, 13595, 10.1021/acssuschemeng.1c04718 Huo, 2020, A liquid phosphorus-containing imidazole derivative as flame-retardant curing agent for epoxy resin with enhanced thermal latency, mechanical, and flame-retardant performances, J Hazard Mater, 386, 121984, 10.1016/j.jhazmat.2019.121984 Xu, 2018, Epoxy nanocomposites simultaneously strengthened and toughened by hybridization with graphene oxide and block ionomer, Compos Sci Technol, 168, 363, 10.1016/j.compscitech.2018.10.020 Sai, 2021, Transparent, highly thermostable and flame retardant polycarbonate enabled by rod-like phosphorous-containing metal complex aggregates, Chem Eng J, 409, 128223, 10.1016/j.cej.2020.128223 Monti, 2013, Thermal and combustion behavior of polyethersulfone-boehmite nanocomposites, Polym Degrad Stabil, 98, 1838, 10.1016/j.polymdegradstab.2013.05.010 Ma, 2021, Effect of functional groups of magnolol-based cyclic phosphonate on structure and properties of flame retardant epoxy resin, Polym Degrad Stabil, 190, 109630, 10.1016/j.polymdegradstab.2021.109630 Sun, 2021, Toughening and strengthening epoxy resin with flame retardant molecular structure based on tyrosine, Polymer, 230, 124045, 10.1016/j.polymer.2021.124045 Wang, 2021, Synthesis of a hyperbranched polyamide charring agent and its flame-retarding and toughening behavior in epoxy resin, Polym Degrad Stabil, 184, 109479, 10.1016/j.polymdegradstab.2020.109479 Zhu, 2020, Mesoporous silica via self-assembly of nano zinc amino-tris-(methylenephosphonate) exhibiting reduced fire hazards and improved impact toughness in epoxy resin, J Hazard Mater, 392, 122343, 10.1016/j.jhazmat.2020.122343 Zhang, 2020, A bio-based hyperbranched flame retardant for epoxy resins, Chem Eng J, 381, 122719, 10.1016/j.cej.2019.122719 Ai, 2020, Mechanically strong and flame-retardant epoxy resins with anti-corrosion performance, Compos B Eng, 193, 108019, 10.1016/j.compositesb.2020.108019 Guo, 2021, Phosphorylated cardanol-formaldehyde oligomers as flame-retardant and toughening agents for epoxy thermosets, Chem Eng J, 423, 130192, 10.1016/j.cej.2021.130192 Shi, 2018, Novel phosphorus-containing halogen-free ionic liquid toward fire safety epoxy resin with well-balanced comprehensive performance, Chem Eng J, 354, 208, 10.1016/j.cej.2018.08.023 Yang, 2021, A highly fire-safe and smoke-suppressive single-component epoxy resin with switchable curing temperature and rapid curing rate, Compos B Eng, 207, 108601, 10.1016/j.compositesb.2020.108601 Huo, 2021, Phosphorus-containing flame retardant epoxy thermosets: recent advances and future perspectives, Prog Polym Sci, 114, 101366, 10.1016/j.progpolymsci.2021.101366 Cheng, 2019, Benzimidazolyl-substituted cyclotriphosphazene derivative as latent flame-retardant curing agent for one-component epoxy resin system with excellent comprehensive performance, Compos B Eng, 177, 107440, 10.1016/j.compositesb.2019.107440 Zhu, 2022, Recent advances in fire-retardant rigid polyurethane foam, J Mater Sci Technol, 112, 315, 10.1016/j.jmst.2021.09.062 Afshari, 2021, A novel triazine-based covalent organic framework: enhancement fire resistance and mechanical performances of thermoplastic polyurethanes, Compos Part A Appl Sci Manuf, 147, 106453, 10.1016/j.compositesa.2021.106453