Top

Journal of Materials Science

Published in:

02-07-2022 | Polymers & biopolymers

Design of epoxy resin with sustainability, high adhesion and excellent flame retardancy based on bio-based molecules

Authors: Ruihang Xie, Yexin Yuan, Pengbo Sun, Zhe Liu, Jinpeng Ma, Guorui Yang, Kui Wang, Ming Li, Lei Shang, Yuhui Ao

Published in: Journal of Materials Science | Issue 27/2022

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

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.

Graphical Abstract

previous article Fractal water structures affected by softener agent in cotton cloths

next article Highly compressible and hydrophobic anisotropic cellulose-based aerogel fabricated by bidirectional freeze-drying for selective oil absorption

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Ahmadi Z (2019) Nanostructured epoxy adhesives: a review. Prog Org Coat 135:449–453. https://doi.org/10.1016/j.porgcoat.2019.06.028CrossRef

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/10.1177/0954008318792984CrossRef

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.2020.107784CrossRef

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.9b02629CrossRef

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.2017.05.007CrossRef

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/molecules24091818CrossRef

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.2019.122719CrossRef

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.2019.11.011CrossRef

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.7b01068CrossRef

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/C7GC02322GCrossRef

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.2018.12.007CrossRef

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.2018.12.007CrossRef

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/s11426-013-5025-3CrossRef

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/C2GC36715GCrossRef

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.201300193CrossRef

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.7b02292CrossRef

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.1859CrossRef

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/c4py00514gCrossRef

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.2015.08.081CrossRef

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.7b00097CrossRef

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.1c00554CrossRef

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.8b00439CrossRef

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/ie201364qCrossRef

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/c5ra12859eCrossRef

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.2004.01.027CrossRef

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/ie5008745CrossRef

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.2019.03.017CrossRef

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.2016.08.013CrossRef

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.2018.06.015CrossRef

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.2015.11.018CrossRef

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.2019.06.024CrossRef

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.2020.109151CrossRef

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/10.1080/00222341003772225CrossRef

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.25030CrossRef

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.2020.109143CrossRef

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.2017.01.014CrossRef

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/s41467-019-10178-0CrossRef

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.2014.11.031CrossRef

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.2014.07.020CrossRef

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.2018.03.006CrossRef

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.2015.10.009CrossRef

Title: Design of epoxy resin with sustainability, high adhesion and excellent flame retardancy based on bio-based molecules
Authors: Ruihang Xie
Yexin Yuan
Pengbo Sun
Zhe Liu
Jinpeng Ma
Guorui Yang
Kui Wang
Ming Li
Lei Shang
Yuhui Ao
Publication date: 02-07-2022
Publisher: Springer US
Published in: Journal of Materials Science / Issue 27/2022
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI: https://doi.org/10.1007/s10853-022-07399-y

Springer Professional

Abstract

Graphical Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 27/2022

Alendronate-loaded gelatin microparticles as templating agents for macroporous magnesium phosphate-based bone cements

Unveiling mechanism of surface-guided platinum nanowire growth

An electrically conductive polyvinyl alcohol/poly (acrylic acid-co-acrylamide)/polydopamine-decorated carbon nanotubes composite hydrogel with appropriate mechanical properties for human movement monitoring

Advantageous optical characteristics of tantalum vanadium oxide as counter electrode in electrochromic devices

Fractal water structures affected by softener agent in cotton cloths

Tailoring the surface morphology of nanostructured cobalt oxide for high-sensitivity CO sensor

Premium Partners