A P/Si-containing polyethylenimine curing agent towards transparent, durable fire-safe, mechanically-robust and tough epoxy resins

Chemical Engineering Journal - Tập 451 - Trang 138768 - 2023
Cheng Wang1, Siqi Huo2, Guofeng Ye1, Pingan Song3, Hao Wang3, Zhitian Liu1
1Hubei Engineering Technology Research Center of Optoelectronic and New Energy Materials, School of Materials Science & Engineering, Wuhan Institute of Technology, Wuhan 430205, China
2Laboratory of Polymer Materials and Engineering, NingboTech University, Ningbo 315100, China
3Center for Future Materials, University of Southern Queensland, Springfield Central 4300, Australia

Tài liệu tham khảo

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, 10.1016/j.jhazmat.2019.121984 Yang, 2020, A highly fire-safe and smoke-suppressive single-component epoxy resin with switchable curing temperature and rapid curing rate, Compos. Part B Eng., 207 Huo, 2021, Phosphorus-containing flame retardant epoxy thermosets: Recent advances and future perspectives, Prog. Polym. Sci., 114, 101366, 10.1016/j.progpolymsci.2021.101366 Zhang, 2021, A molecularly engineered bioderived polyphosphate for enhanced flame retardant, UV-blocking and mechanical properties of poly(lactic acid), Chem. Eng. J., 411, 10.1016/j.cej.2021.128493 Ye, 2021, A novel hyperbranched phosphorus-boron polymer for transparent, flame-retardant, smoke-suppressive, robust yet tough epoxy resins, Compos. Part B Eng., 227, 10.1016/j.compositesb.2021.109395 Sheng, 2019, Influence of zinc stannate and graphene hybrids on reducing the toxic gases and fire hazards during epoxy resin combustion, Polym. Adv. Technol., 30, 666, 10.1002/pat.4502 Lou, 2021, Fully Biobased Surface-Functionalized Microcrystalline Cellulose via Green Self-Assembly toward Fire-Retardant, Strong, and Tough Epoxy Biocomposites, ACS Sustain. Chem. Eng., 9, 13595, 10.1021/acssuschemeng.1c04718 Zhao, 2020, Novel organophosphorus compound with amine groups towards self-extinguishing epoxy resins at low loading, Mater. Des., 193, 10.1016/j.matdes.2020.108838 Liu, 2021, Cyanate ester resins containing Si-O-C hyperbranched polysiloxane with favorable curing processability and toughness for electronic packaging, Chem. Eng. J., 433 Liu, 2022, Flame-Retardant multifunctional epoxy resin with high performances, Chem. Eng. J., 427, 10.1016/j.cej.2021.132031 Pomázi, 2021, Development of fire retardant epoxy-based gelcoats for carbon fibre reinforced epoxy resin composites, Prog. Org. Coat., 151 Huo, 2016, A phosphorus-containing phenolic derivative and its application in benzoxazine resins: Curing behavior, thermal, and flammability properties, J. Appl. Polym. Sci., 133, 10.1002/app.43403 Huo, 2022, Flame-retardant, transparent, mechanically-strong and tough epoxy resin enabled by high-efficiency multifunctional boron-based polyphosphonamide, Chem. Eng. J., 427, 10.1016/j.cej.2021.131578 Huo, 2019, Synthesis of a phosphaphenanthrene/benzimidazole-based curing agent and its application in flame-retardant epoxy resin, Polym. Degrad. Stabil., 163, 100, 10.1016/j.polymdegradstab.2019.03.003 Bi, 2022, A core–shell-structured APP@COFs hybrid for enhanced flame retardancy and mechanical property of epoxy resin (EP), Adv. Compos. Hybrid Mater., 1 Yang, 2016, Synthesis of a phosphorus/nitrogen-containing compound based on maleimide and cyclotriphosphazene and its flame-retardant mechanism on epoxy resin, Polym. Degrad. Stabil., 126, 9, 10.1016/j.polymdegradstab.2016.01.011 Chen, 2020, Synthesis of chitosan-based flame retardant and its fire resistance in epoxy resin, Carbohydr. Polym., 245, 10.1016/j.carbpol.2020.116530 Sai, 2020, Deposition growth of Zr-based MOFs on cerium phenylphosphonate lamella towards enhanced thermal stability and fire safety of polycarbonate, Compos. Part B Eng., 197, 10.1016/j.compositesb.2020.108064 Huo, 2016, Synthesis of a novel phosphorus-nitrogen type flame retardant composed of maleimide, triazine-trione, and phosphaphenanthrene and its flame retardant effect on epoxy resin, Polym. Degrad. Stabil., 131, 106, 10.1016/j.polymdegradstab.2016.07.013 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 Chen, 2021, Novel phosphorus/nitrogen/boron-containing carboxylic acid as co-curing agent for fire safety of epoxy resin with enhanced mechanical properties, J. Hazard. Mater., 402, 10.1016/j.jhazmat.2020.123769 Shao, 2019, An Excellent Intrinsic Transparent Epoxy Resin with High Flame Retardancy: Synthesis, Characterization, and Properties, Macromol. Mater. Eng., 304, 1900254, 10.1002/mame.201900254 Shao, 2020, Phosphorus/sulfur-containing aliphatic polyamide curing agent endowing epoxy resin with well-balanced flame safety, transparency and refractive index, Mater. Des., 187, 10.1016/j.matdes.2019.108417 Shao, 2018, A novel multi-functional polymeric curing agent: Synthesis, characterization, and its epoxy resin with simultaneous excellent flame retardance and transparency, Chem. Eng. J., 345, 471, 10.1016/j.cej.2018.03.142 Liu, 2011, Efficient accelerating effect of carbonyldiimidazole on epoxy-dicyandiamide curing system, J. Polym. Sci., Part A: Polym. Chem., 49, 250, 10.1002/pola.24448 Zhang, 2019, Eco-friendly flame retardant and electromagnetic interference shielding cotton fabrics with multi-layered coatings, Chem. Eng. J., 372, 1077, 10.1016/j.cej.2019.05.012 Wang, 2019, Colloidal-electrochemical fabrication strategies for functional composites of linear polyethylenimine, J. Colloid Interface Sci., 552, 1, 10.1016/j.jcis.2019.05.039 Shi, 2019, Bi-phase fire-resistant polyethylenimine/graphene oxide/melanin coatings using layer by layer assembly technique: Smoke suppression and thermal stability of flexible polyurethane foams, Polymer, 170, 65, 10.1016/j.polymer.2019.03.008 Li, 2019, Highly efficient multielement flame retardant for multifunctional epoxy resin with satisfactory thermal, flame-retardant, and mechanical properties, Polym. Adv. Technol., 31, 146, 10.1002/pat.4758 Huo, 2018, Synergistic effect between a novel triazine-based flame retardant and DOPO/HPCP on epoxy resin, Polym. Adv. Technol., 29, 2774, 10.1002/pat.4400 Chen, 2018, Study on properties of flame-retardant cyanate esters modified with DOPO and triazine compounds, Polym. Adv. Technol., 29, 2574, 10.1002/pat.4368 Wang, 2006, A Novel Phosphorus-Containing Poly(ethylene terephthalate) Nanocomposite with Both Flame Retardancy and Anti-Dripping Effects, Macromol. Mater. Eng., 291, 638, 10.1002/mame.200600017 Zhan, 2021, Synthesis of a bio-based flame retardant via a facile strategy and its synergistic effect with ammonium polyphosphate on the flame retardancy of polylactic acid, Polym. Degrad. Stabil., 191, 10.1016/j.polymdegradstab.2021.109684 Qiu, 2018, Toughening Effect and Flame-Retardant Behaviors of Phosphaphenanthrene/Phenylsiloxane Bigroup Macromolecules in Epoxy Thermoset, Macromolecules, 51, 9992, 10.1021/acs.macromol.8b02090 Ai, 2020, Multifunctional Phosphorus-Containing Triazolyl Amine toward Self-Intumescent Flame-Retardant and Mechanically Strong Epoxy Resin with High Transparency, Ind. Eng. Chem. Res., 59, 11918, 10.1021/acs.iecr.0c01277 Xing, 2011, Synthesis and thermal behavior of a novel UV-curable transparent flame retardant film and phosphorus-nitrogen synergism of flame retardancy, Polym. Adv. Technol., 22, 2123, 10.1002/pat.1732 Yu, 2022, Interface nanoengineering of a core-shell structured biobased fire retardant for fire-retarding polylactide with enhanced toughness and UV protection, J. Cleaner Prod., 336, 10.1016/j.jclepro.2022.130372 Ye, 2020, Facile synthesis of lithium containing polyhedral oligomeric phenyl silsesquioxane and its superior performance in transparency, smoke suppression and flame retardancy of epoxy resin, Compos. Sci. Technol., 189, 10.1016/j.compscitech.2020.108004 Seraji, 2022, Fire-retardant unsaturated polyester thermosets: The state-of-the-art, challenges and opportunities, Chem. Eng. J., 430, 10.1016/j.cej.2021.132785 Huo, 2022, A hyperbranched P/N/B-containing oligomer as multifunctional flame retardant for epoxy resins, Compos. Part B Eng., 234, 10.1016/j.compositesb.2022.109701 Zhang, 2020, A bio-based hyperbranched flame retardant for epoxy resins, Chem. Eng. J., 381, 10.1016/j.cej.2019.122719 Hou, 2022, The P/Si synergistic effect enduing epoxy resin with improved flame retardancy and outstanding mechanical properties, High Perform. Polym., 34, 545, 10.1177/09540083221080661 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 Jana, 2021, Accessing the Next Generation of Synthetic Mussel-Glue Polymers via Mussel-Inspired Polymerization, Angew. Chem., Int. Ed., 60, 6408, 10.1002/anie.202015833 Lv, 2020, Robust icephobic epoxy coating using maleic anhydride as a crosslinking agent, Prog. Org. Coat., 142 Ma, 2022, A lava-inspired micro/nano-structured ceramifiable organic-inorganic hybrid fire-extinguishing coating, Matter, 5, 1, 10.1016/j.matt.2021.12.009 He, 2022, P, N-decorated halloysite nanotubes for flame retardancy enhancement of polyamide 6/aluminum diethylphosphinate, Polym. Degrad. Stabil., 196, 10.1016/j.polymdegradstab.2022.109847 Jian, 2022, Facile construction of lamellar-like phosphorus-based triazole-zinc complex for high-performance epoxy resins, J Colloid Interface Sci., 609, 513, 10.1016/j.jcis.2021.11.054 Feng, 2022, A Si-containing polyphosphoramide via green chemistry for fire-retardant polylactide with well-preserved mechanical and transparent properties, Chem. Eng. J., 431, 10.1016/j.cej.2021.134259 Fu, 2019, Flame-retarding nanoparticles as the compatibilizers for immiscible polymer blends: simultaneously enhanced mechanical performance and flame retardancy†, J. Mater. Chem. A, 7, 4903, 10.1039/C8TA12233D Sai, 2021, Fabrication and Mechanism Study of Cerium-Based P, N-Containing Complexes for Reducing Fire Hazards of Polycarbonate with Superior Thermostability and Toughness, ACS Appl. Mater. Inter., 13, 30061, 10.1021/acsami.1c07153 Gupta, 2021, Effect of Montmorillonite Clay Content on the Mechanical and Thermal Properties of Flame Retardant Epoxy Nanocomposites, Int. J. Sci. Res. Mech. Mater. Eng., 5, 22 Wang, 2016, Synthesis of a novel phosphorus-containing epoxy curing agent and the thermal, mechanical and flame-retardant properties of the cured products, Polym. Degrad. Stabil., 130, 143, 10.1016/j.polymdegradstab.2016.06.002 Li, 2019, Influence of eco-friendly calcium gluconate on the intumescent flame-retardant epoxy resin: Flame retardancy, smoke suppression and mechanical properties, Compos. Part B Eng., 176, 10.1016/j.compositesb.2019.107200 Vu, 2020, Effects of DOPO-Grafted Epoxidized Soybean Oil on Fracture Toughness and Flame Retardant of Epoxy Resin/Rice Husk Silica Hybrid, Macromol. Res., 28, 826, 10.1007/s13233-020-8102-4 Mamani, 2017, A study on mechanical, thermal and flame retardant properties of epoxy/expandable graphite composites, Pigm. Resin Technol., 46, 131, 10.1108/PRT-11-2015-0112 Nguyen, 2020, MWCNT grafted with POSS-based novel flame retardant-filled epoxy resin nanocomposite: fabrication, mechanical properties, and flammability, Compos. Interfaces, 28, 843, 10.1080/09276440.2020.1816068 Nguyen, 2021, Banana Fiber-Reinforced Epoxy Composites: Mechanical Properties and Fire Retardancy, Int. J. Chem. Eng., 2021, 1 Smith, 2018, Environmentally Benign Halloysite Nanotube Multilayer Assembly Significantly Reduces Polyurethane Flammability, Adv. Funct. Mater., 28, 1703289, 10.1002/adfm.201703289 Huang, 2021, Multifunctional graphene-based nano-additives toward high-performance polymer nanocomposites with enhanced mechanical, thermal, flame retardancy and smoke suppressive properties, Chem. Eng. J., 410, 10.1016/j.cej.2020.127590 Nabipour, 2021, Organic-inorganic hybridization of isoreticular metal-organic framework-3 with melamine for efficiently reducing the fire risk of epoxy resin, Compos. Part B Eng., 211, 10.1016/j.compositesb.2021.108606 Wu, 2019, An intramolecular hybrid of metal polyhedral oligomeric silsesquioxanes with special titanium-embedded cage structure and flame retardant functionality, Chem. Eng. J., 374, 1304, 10.1016/j.cej.2019.06.027 Ye, 2021, One-step and green synthesis of a bio-based high-efficiency flame retardant for poly (lactic acid), Polym. Degrad. Stabil., 192, 10.1016/j.polymdegradstab.2021.109696 Wang, 2020, Exfoliated and functionalized boron nitride nanosheets towards improved fire resistance and water tolerance of intumescent fire retardant coating, J. Appl. Polym. Sci., 138, 50177, 10.1002/app.50177 Zhu, 2022, Recent advances in fire-retardant rigid polyurethane foam, J. Mater. Sci. Technol., 112, 315, 10.1016/j.jmst.2021.09.062