Design of epoxy resin with sustainability, high adhesion and excellent flame retardancy based on bio-based molecules
Source abstract
Abstract
The preparation of bio-based epoxy resin with excellent thermal properties and flame retardant properties from green renewable resources had attracted extensive attention in recent years. Starting from the driving structural properties, the purpose of this study is to prepare multifunctional triglycidylester- diphenolic acid- bio-based epoxy (TDBE) with diphenolic acid (DPA), triglycidyl isocyanurate (TGIC), and 9,10-dihydro-9-oxa-10-phosphophenanthrene 10 oxide (DOPO) as raw materials. TDBE/DDM and bisphenol A epoxy resin curing agent (DGEBA/DDM) was prepared with 4,4 `- diaminodiphenylmethane (DDM) as curing agent. TDBE/DDM has excellent fire safety. LOI value rose from 24.5 to 42.0%, and the UL-94 test level passes V-0 level. In the cone calorimeter test, the peak heat release rate (pHRR) is decreased by 69.3%. Besides, the lap shear TDBE adhesive strength was 42.9 MPa, which increased by 62.5%. This new multifunctional bio-based flame retardant epoxy resin provides a broader application prospect for high-performance materials.
Source: expertdata · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Flame retardant materials and properties · Polymer composites and self-healing · Carbon dioxide utilization in catalysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (41)
Show source-provided references
1. Ahmadi Z (2019) Nanostructured epoxy adhesives: a review. Prog Org Coat 135:449–453. https://doi.org/10.1016/j.porgcoat.2019.06.02810.1016/j.porgcoat.2019.06.028 ↗
2. Khagokpam GKS, Halder S (2018) Paraffin wax microsphere embedded epoxy composites for potential thermal management in electronic devices. High Perform Polym 31(7):767–777. https://doi.org/10.1177/095400831879298410.1177/0954008318792984 ↗
3. Yang X, Zhu J, Yang D, Zhang J, Guo Y, Zhong X et al (2020) High-efficiency improvement of thermal conductivities for epoxy composites from synthesized liquid crystal epoxy followed by doping BN fillers. Compos B Eng 185:107784. https://doi.org/10.1016/j.compositesb.2020.10778410.1016/j.compositesb.2020.107784 ↗
4. Pourchet S, Sonnier R, Ben-Abdelkader M, Gaillard Y, Ruiz Q, Placet V et al (2019) New Reactive Isoeugenol Based Phosphate Flame Retardant: Toward Green Epoxy Resins. ACS Sustain Chem Eng 7(16):14074–14088. https://doi.org/10.1021/acssuschemeng.9b0262910.1021/acssuschemeng.9b02629 ↗
5. Shibata M, Ohkita T (2017) Fully biobased epoxy resin systems composed of a vanillin-derived epoxy resin and renewable phenolic hardeners. Eur Polymer J 92:165–173. https://doi.org/10.1016/j.eurpolymj.2017.05.00710.1016/j.eurpolymj.2017.05.007 ↗
6. Ecochard Y, Decostanzi M, Negrell C, Sonnier R, Caillol S (2019) Cardanol and Eugenol Based Flame Retardant Epoxy Monomers for Thermostable Networks. Molecules. 24(9):1818. https://doi.org/10.3390/molecules2409181810.3390/molecules24091818 ↗
7. Zhang J, Mi X, Chen S, Xu Z, Zhang D, Miao M et al (2020) A bio-based hyperbranched flame retardant for epoxy resins. Chem Eng J 381:122719. https://doi.org/10.1016/j.cej.2019.12271910.1016/j.cej.2019.122719 ↗
8. Fang F, Huo S, Shen H, Ran S, Wang H, Song P et al (2020) A bio-based ionic complex with different oxidation states of phosphorus for reducing flammability and smoke release of epoxy resins. Compos Commun 17:104–108. https://doi.org/10.1016/j.coco.2019.11.01110.1016/j.coco.2019.11.011 ↗
9. Jian X-Y, An X-P, Li Y-D, Chen J-H, Wang M, Zeng J-B (2017) All Plant Oil Derived Epoxy Thermosets with Excellent Comprehensive Properties. Macromolecules 50(15):5729–5738. https://doi.org/10.1021/acs.macromol.7b0106810.1021/acs.macromol.7b01068 ↗
10. Faye I, Decostanzi M, Ecochard Y, Caillol S (2017) Eugenol bio-based epoxy thermosets: from cloves to applied materials. Green Chem 19(21):5236–5242. https://doi.org/10.1039/C7GC02322G10.1039/C7GC02322G ↗
11. Jiang H, Sun L, Zhang Y, Liu Q, Ru C, Zhang W et al (2019) Novel biobased epoxy resin thermosets derived from eugenol and vanillin. Polym Degrad Stab 160:45–52. https://doi.org/10.1016/j.polymdegradstab.2018.12.00710.1016/j.polymdegradstab.2018.12.007 ↗
12. Fache M, Viola A, Auvergne R, Boutevin B, Caillol S (2015) Biobased epoxy thermosets from vanillin-derived oligomers. Eur Polymer J 68:526–535. https://doi.org/10.1016/j.polymdegradstab.2018.12.00710.1016/j.polymdegradstab.2018.12.007 ↗
13. Ma S, Liu X, Jiang Y, Fan L, Feng J, Zhu J (2013) Synthesis and properties of phosphorus-containing bio-based epoxy resin from itaconic acid. Sci China Chem 57(3):379–388. https://doi.org/10.1007/s11426-013-5025-310.1007/s11426-013-5025-3 ↗
14. Ma S, Liu X, Jiang Y, Tang Z, Zhang C, Zhu J (2013) Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers. Green Chem 15(1):245–254. https://doi.org/10.1039/C2GC36715G10.1039/C2GC36715G ↗
15. Jaillet F, Darroman E, Ratsimihety A, Auvergne R, Boutevin B, Caillol S (2014) New biobased epoxy materials from cardanol. Eur J Lipid Sci Technol 116(1):63–73. https://doi.org/10.1002/ejlt.20130019310.1002/ejlt.201300193 ↗
16. Nguyen TKL, Livi S, Soares BG, Barra GMO, Gérard J-F, Duchet-Rumeau J (2017) Development of Sustainable Thermosets from Cardanol-based Epoxy Prepolymer and Ionic Liquids. ACS Sustain Chem Eng 5(9):8429–8438. https://doi.org/10.1021/acssuschemeng.7b0229210.1021/acssuschemeng.7b02292 ↗
17. Feng X, East AJ, Hammond WB, Zhang Y, Jaffe M (2011) Overview of advances in sugar-based polymers. Polym Adv Technol 22(1):139–150. https://doi.org/10.1002/pat.185910.1002/pat.1859 ↗
18. Hong J, Radojčić D, Ionescu M, Petrović ZS, Eastwood E (2014) Advanced materials from corn: isosorbide-based epoxy resins. Polym Chem 5(18):5360–5368. https://doi.org/10.1039/c4py00514g10.1039/c4py00514g ↗
19. Gu J, Yang X, Lv Z, Li N, Liang C, Zhang Q (2016) Functionalized graphite nanoplatelets/epoxy resin nanocomposites with high thermal conductivity. Int J Heat Mass Transf 92:15–22. https://doi.org/10.1016/j.ijheatmasstransfer.2015.08.08110.1016/j.ijheatmasstransfer.2015.08.081 ↗
20. Wang S, Ma S, Xu C, Liu Y, Dai J, Wang Z et al (2017) Vanillin-derived high-performance flame retardant epoxy resins: facile synthesis and properties. Macromolecules 50(5):1892–1901. https://doi.org/10.1021/acs.macromol.7b0009710.1021/acs.macromol.7b00097 ↗
21. Qian Z, Zheng Y, Li Q, Wang L, Fu F, Liu X (2021) Amidation way of diphenolic acid for preparing biopolybenzoxazine resin with outstanding thermal performance. ACS Sustain Chem Eng 9(12):4668–4680. https://doi.org/10.1021/acssuschemeng.1c0055410.1021/acssuschemeng.1c00554 ↗
22. Dai J, Peng Y, Teng N, Liu Y, Liu C, Shen X et al (2018) High performing and fire resistant biobased epoxy resin from renewable sources. ACS Sustain Chem Eng 6(6):7589–7599. https://doi.org/10.1021/acssuschemeng.8b0043910.1021/acssuschemeng.8b00439 ↗
23. Deng L, Shen M, Yu J, Wu K, Ha C (2012) Preparation, characterization, and flame retardancy of novel rosin-based siloxane epoxy resins. Ind Eng Chem Res 51(24):8178–8184. https://doi.org/10.1021/ie201364q10.1021/ie201364q ↗
24. Ménard R, Negrell C, Fache M, Ferry L, Sonnier R, David G (2015) From a bio-based phosphorus-containing epoxy monomer to fully bio-based flame-retardant thermosets. RSC Adv 5(87):70856–70867. https://doi.org/10.1039/c5ra12859e10.1039/c5ra12859e ↗
25. Mauerer O (2005) New reactive, halogen-free flame retardant system for epoxy resins. Polym Degrad Stab 88(1):70–73. https://doi.org/10.1016/j.polymdegradstab.2004.01.02710.1016/j.polymdegradstab.2004.01.027 ↗
26. Chao P, Li Y, Gu X, Han D, Jia X, Wang M et al (2015) Novel phosphorus–nitrogen–silicon flame retardants and their application in cycloaliphatic epoxy systems. Polym Chem 6(15):2977–2985. https://doi.org/10.1021/ie500874510.1021/ie5008745 ↗
27. Liu L, Xu Y, Xu M, Li Z, Hu Y, Li B (2019) Economical and facile synthesis of a highly efficient flame retardant for simultaneous improvement of fire retardancy, smoke suppression and moisture resistance of epoxy resins. Compos B Eng 167:422–433. https://doi.org/10.1016/j.compositesb.2019.03.01710.1016/j.compositesb.2019.03.017 ↗
28. Zhao B, Liang W-J, Wang J-S, Li F, Liu Y-Q (2016) Synthesis of a novel bridged-cyclotriphosphazene flame retardant and its application in epoxy resin. Polym Degrad Stab 133:162–173. https://doi.org/10.1016/j.polymdegradstab.2016.08.01310.1016/j.polymdegradstab.2016.08.013 ↗
29. Tao X, Duan H, Dong W, Wang X, Yang S (2018) Synthesis of an acrylate constructed by phosphaphenanthrene and triazine-trione and its application in intrinsic flame retardant vinyl ester resin. Polym Degrad Stab 154:285–294. https://doi.org/10.1016/j.polymdegradstab.2018.06.01510.1016/j.polymdegradstab.2018.06.015 ↗
30. Xu M-J, Xu G-R, Leng Y, Li B (2016) Synthesis of a novel flame retardant based on cyclotriphosphazene and DOPO groups and its application in epoxy resins. Polym Degrad Stab 123:105–114. https://doi.org/10.1016/j.polymdegradstab.2015.11.01810.1016/j.polymdegradstab.2015.11.018 ↗
31. Jin S, Qian L, Qiu Y, Chen Y, Xin F (2019) High-efficiency flame retardant behavior of bi-DOPO compound with hydroxyl group on epoxy resin. Polym Degrad Stab 166:344–352. https://doi.org/10.1016/j.polymdegradstab.2019.06.02410.1016/j.polymdegradstab.2019.06.024 ↗
32. Chi Z, Guo Z, Xu Z, Zhang M, Li M, Shang L et al (2020) A DOPO-based phosphorus-nitrogen flame retardant bio-based epoxy resin from diphenolic acid: synthesis, flame-retardant behavior and mechanism. Polym Degrad Stab 176:109151. https://doi.org/10.1016/j.polymdegradstab.2020.10915110.1016/j.polymdegradstab.2020.109151 ↗
33. Lu C, Ye R, Yang Y, Ren X, Cai X (2010) Chemical modification of polyamide 6 by chain extension with terephthaloyl-biscaprolactam. J Macromol Sci Part B 50(2):350–362. https://doi.org/10.1080/0022234100377222510.1080/00222341003772225 ↗
34. Xu MJ, Liu HC, Ma K, Li B, Zhang ZY (2018) New strategy towards flame retardancy through design, synthesis, characterization, and fire performance of a chain extender in polyamide 6 composites. Polym Eng Sci. 59:E206–E215. https://doi.org/10.1002/pen.2503010.1002/pen.25030 ↗
35. Cui M, Zhang L, Lou P, Zhang X, Han X, Zhang Z et al (2020) Study on thermal degradation mechanism of heat-resistant epoxy resin modified with carboranes. Polym Degrad Stab 176:109143. https://doi.org/10.1016/j.polymdegradstab.2020.10914310.1016/j.polymdegradstab.2020.109143 ↗
36. Wang P, Cai Z (2017) Highly efficient flame-retardant epoxy resin with a novel DOPO-based triazole compound: Thermal stability, flame retardancy and mechanism. Polym Degrad Stab 137:138–150. https://doi.org/10.1016/j.polymdegradstab.2017.01.01410.1016/j.polymdegradstab.2017.01.014 ↗
37. Qi Y, Wang J, Kou Y, Pang H, Zhang S, Li N et al (2019) Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock. Nat Commun 10(1):2107. https://doi.org/10.1038/s41467-019-10178-010.1038/s41467-019-10178-0 ↗
38. Kasemsiri P, Neramittagapong A, Chindaprasirt P (2015) Curing kinetic, thermal and adhesive properties of epoxy resin cured with cashew nut shell liquid. Thermochim Acta 600:20–27. https://doi.org/10.1016/j.tca.2014.11.03110.1016/j.tca.2014.11.031 ↗
39. Xu G-R, Xu M-J, Li B (2014) Synthesis and characterization of a novel epoxy resin based on cyclotriphosphazene and its thermal degradation and flammability performance. Polym Degrad Stab 109:240–248. https://doi.org/10.1016/j.polymdegradstab.2014.07.02010.1016/j.polymdegradstab.2014.07.020 ↗
40. Fu X-L, Wang X, Xing W, Zhang P, Song L, Hu Y (2018) Two-dimensional cardanol-derived zirconium phosphate hybrid as flame retardant and smoke suppressant for epoxy resin. Polym Degrad Stab 151:172–180. https://doi.org/10.1016/j.polymdegradstab.2018.03.00610.1016/j.polymdegradstab.2018.03.006 ↗
41. Liu B-W, Zhao H-B, Tan Y, Chen L, Wang Y-Z (2015) Novel crosslinkable epoxy resins containing phenylacetylene and azobenzene groups: from thermal crosslinking to flame retardance. Polym Degrad Stab 122:66–76. https://doi.org/10.1016/j.polymdegradstab.2015.10.00910.1016/j.polymdegradstab.2015.10.009 ↗