Enhancement of Thermal and Mechanical Properties of Bismaleimide Using a Graphene Oxide Modified by Epoxy Silane
Abstract
:1. Introduction
2. Experimental
2.1. Raw Materials
2.2. Preparation of Specimens
2.3. Characterization and Measurements
3. Results and Discussion
3.1. Characterization of ES-GO
3.2. Thermal Stability Analysis
3.3. Dynamicmechanical Analysis
3.4. Mechanical Properties
3.5. Damp Heat Resistance
3.6. Properties of Composites
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Liu, M.; Duan, Y.; Wang, Y.; Zhao, Y. Diazonium functionalization of graphene nanosheets and impact response of aniline modified graphene/bismaleimide nanocomposites. Mater. Des. 2014, 53, 466–474. [Google Scholar] [CrossRef]
- Pham, Q.T.; Yu, F.E.; Hsu, J.M.; Pan, J.P.; Wang, T.H.; Chern, C.S. Polymerization kinetics of reactive N, N′-bismaleimide-4, 4′-diphenylmethane/barbituric acid based microgel particles. Thermochim. Acta 2014, 597, 1–7. [Google Scholar] [CrossRef]
- Jin, W.; Yuan, L.; Liang, G.; Gu, A. Multifunctional cyclotriphosphazene/hexagonal boron nitride hybrids and their flame retarding bismaleimide resins with high thermal conductivity and thermal stability. ACS Appl. Mater. Int. 2014, 6, 14931–14944. [Google Scholar] [CrossRef] [PubMed]
- Qiu, L.; Guo, P.; Yang, X.; Ouyang, Y.; Feng, Y.; Zhang, X.; Zhao, J.; Zhang, X.; Li, Q. Electro curing of oriented bismaleimide between aligned carbon nanotubes for high mechanical and thermal performances. Carbon 2019, 145, 650–657. [Google Scholar] [CrossRef]
- Wu, G.; Kou, K.; Chao, M.; Zhuo, L.; Zhang, J.; Li, N. Preparation and characterization of bismaleimide-triazine/epoxy interpenetrating polymer networks. Thermochim. Acta 2012, 537, 44–50. [Google Scholar] [CrossRef]
- Wang, Y.; Kou, K.; Wu, G.; Zhuo, L.; Li, J.; Zhang, Y. The curing reaction of benzoxazine with bismaleimide/cyanate ester resin and the properties of the terpolymer. Polymer 2015, 77, 354–360. [Google Scholar] [CrossRef]
- Shanmugam, K.V.; Parent, J.S.; Whitney, R.A. Design, synthesis, and characterization of bismaleimide co-curing elastomers. Ind. Eng. Chem. Res. 2012, 51, 8957–8965. [Google Scholar] [CrossRef]
- Xiong, X.; Ren, R.; Chen, P.; Yu, Q.; Wang, J.; Jia, C. Preparation and properties of modified bismaleimide resins based on phthalide-containing monomer. J. Appl. Polym. Sci. 2013, 130, 1084–1091. [Google Scholar] [CrossRef]
- Iredale, R.J.; Ward, C.; Hamerton, I. Modern advances in bismaleimide resin technology: A 21st century perspective on the chemistry of addition polyimides. Prog. Polym. Sci. 2017, 69, 1–21. [Google Scholar] [CrossRef] [Green Version]
- Gouzman, I.; Atar, N.; Grossman, E.; Verker, R.; Bolker, A.; Pokrass, M.; Sultan, S.; Sinwani, O.; Wagner, A.; Lück, T.; et al. 3D printing of bismaleimides: From new ink formulation to printed thermosetting polymer objects. Adv. Mater. Technol. 2019, 4, 1900368. [Google Scholar] [CrossRef]
- Takeichi, T.; Saito, Y.; Agag, T.; Muto, H.; Kawauchi, T. High-performance polymer alloys of polybenzoxazine and bismaleimide. Polymer 2008, 49, 1173–1179. [Google Scholar] [CrossRef]
- Hannoda, Y.; Akasaka, Y.; Shibata, M. Bio-based thermosetting bismaleimide resins using cardany linolenate and allyl cardanyl ether. React. Funct. Polym. 2015, 97, 96–104. [Google Scholar] [CrossRef]
- Yu, F.E.; Hsu, J.M.; Pan, J.P.; Wang, T.H.; Chern, C.S. Kinetics of Michael addition polymerizations of n,n′-bismaleimide-4,4′-diphenylmethane with barbituric acid. Polym. Eng. Sci. 2013, 53, 204–211. [Google Scholar] [CrossRef]
- Yu, F.E.; Hsu, J.M.; Pan, J.P.; Wang, T.H.; Chiang, Y.C.; Lin, W.; Jiang, J.C.; Chern, C.S. Effect of solvent proton affinity on the kinetics of michael addition polymerization of n,n′-bismaleimide-4,4′-diphenylmethane with barbituric acid. Polym. Eng. Sci. 2014, 54, 559–568. [Google Scholar] [CrossRef]
- Zeng, X.; Yu, S.; Lai, M.; Sun, R.; Wong, C.P. Tuning the mechanical properties of glass fiber-reinforced bismaleimide–triazine resin composites by constructing a flexible bridge at the interface. Sci. Technol. Adv. Mat. 2013, 14, 065001. [Google Scholar] [CrossRef] [PubMed]
- Xiong, X.; Chen, P.; Yu, Q.; Zhu, N.; Wang, B.; Zhang, J.; Li, J. Synthesis and properties of chain-extended bismaleimide resins containing phthalide cardo structure. Polym. Int. 2010, 59, 1665–1672. [Google Scholar] [CrossRef]
- Ding, Z.; Yuan, L.; Guan, Q.; Gu, A.; Liang, G. A reconfiguring and self-healing thermoset epoxy/chain-extended bismaleimide resin system with thermally dynamic covalent bonds. Polymer 2018, 147, 170–182. [Google Scholar] [CrossRef]
- Xiong, X.; Ma, X.; Chen, P.; Zhou, L.; Ren, R.; Liu, S. New chain-extended bismaleimides with aryl-ether-imide and phthalide cardo skeleton (I): Synthesis, characterization and properties. React. Funct. Polym. 2018, 129, 29–37. [Google Scholar] [CrossRef]
- Liu, C.; Yan, H.; Lv, Q.; Li, S.; Niu, S. Enhanced tribological properties of aligned reduced graphene oxide-Fe3O4@polyphosphazene/bismaleimides composites. Carbon 2016, 102, 145–153. [Google Scholar] [CrossRef]
- Liu, C.; Yan, H.; Chen, Z.; Yuan, L.; Liu, T. Enhanced tribological properties of bismaleimides filled with aligned graphene nanosheets coated with Fe3O4 nanorods. J. Mater. Chem. A 2015, 3, 10559–10565. [Google Scholar] [CrossRef]
- Uchida, S.; Ishige, R.; Ando, S. Enhancement of thermal diffusivity in phase-separated bismaleimide/poly (ether imide) composite films containing needle-shaped ZnO particles. Polymers 2017, 9, 263. [Google Scholar] [CrossRef]
- Marcano, D.C.; Kosynkin, D.V.; Berlin, J.M.; Sinitskii, A.; Sun, Z.; Slesarev, A.; Alemany, L.B.; Lu, W.; Tour, J.M. Improved synthesis of graphene oxide. ACS Nano 2010, 4, 4806–4814. [Google Scholar] [CrossRef]
- Chen, L.; Shi, G.; Shen, J.; Peng, B.; Zhang, B.; Wang, Y.; Bian, F.; Wang, J.; Li, D.; Qian, Z.; et al. Ion sieving in graphene oxide membranes via cationic control of interlayer spacing. Nature 2017, 550, 380–383. [Google Scholar] [CrossRef]
- De-Silva, K.K.; Huang, H.H.; Joshi, R.K.; Yoshimura, M. Chemical reduction of graphene oxide using green reductants. Carbon 2017, 119, 190–199. [Google Scholar] [CrossRef]
- Hang, C.; Guangbao, M.; Peijie, L.; Xu, H.; Chunxiao, C. Microstructure and Tensile Properties of Graphene-Oxide-Reinforced High-Temperature Titanium-Alloy-Matrix Composites. Materials 2020, 13, 3358. [Google Scholar] [CrossRef]
- Xiaoxiao, H.; Peiquan, X.; Hongying, G.; Guotao, Y. Synthesis and Characterization of WO3/Graphene Nanocomposites for Enhanced Photocatalytic Activities by One-Step In-Situ Hydrothermal Reaction. Materials 2018, 11, 147. [Google Scholar] [CrossRef] [Green Version]
- Zejun, P.; Penglun, Z.; Yu, Z. Poly (3,4-Ethylenedioxythiophene) (PEDOT) Nanofibers Decorated Graphene Oxide (GO) as High-Capacity, Long Cycle Anodes for Sodium Ion Batteries. Materials 2018, 11, 2032. [Google Scholar] [CrossRef] [Green Version]
- Politano, G.G.; Vena, C.; Desiderio, G.; Versace, C. Variable Angle Spectroscopic Ellipsometry Characterization of Reduced Graphene Oxide Stabilized with Poly (Sodium 4-Styrenesulfonate). Coatings 2020, 10, 743. [Google Scholar] [CrossRef]
- Kosowska, K.; Domalik-Pyzik, P.; Krok-Borkowicz, M.; Chłopek, J. Synthesis and characterization of chitosan/reduced graphene oxide hybrid composites. Materials. 2019, 12, 2077. [Google Scholar] [CrossRef] [Green Version]
- Smith, A.T.; LaChance, A.M.; Zeng, S.; Liu, B.; Sun, L. Synthesis, properties, and applications of graphene oxide/reduced graphene oxide and their nanocomposites. Nano Mater. Sci. 2019, 1, 31–47. [Google Scholar] [CrossRef]
- Zhang, J.; Zhang, Z.; Jiao, Y.; Yang, H.; Li, Y.; Zhang, J.; Gao, P. The graphene/lanthanum oxide nanocomposites as electrode materials of supercapacitors. J. Power Sources 2019, 419, 99–105. [Google Scholar] [CrossRef]
- Alam, S.N.; Sharma, N.; Kumar, L. Synthesis of graphene oxide (GO) by modified hummers method and its thermal reduction to obtain reduced graphene oxide (rGO). Graphene 2017, 6, 1–18. [Google Scholar] [CrossRef] [Green Version]
- Shi, Y.; Yu, B.; Zheng, Y.; Yang, J.; Duan, Z.; Hu, Y. Design of reduced graphene oxide decorated with DOPO-phosphanomidate for enhanced fire safety of epoxy resin. J. Colloid Interface Sci. 2018, 521, 160–171. [Google Scholar] [CrossRef]
- Fang, F.; Ran, S.; Fang, Z.; Song, P.; Wang, H. Improved flame resistance and thermo-mechanical properties of epoxy resin nanocomposites from functionalized graphene oxide via self-assembly in water. Compos. B Eng. 2019, 165, 406–416. [Google Scholar] [CrossRef]
- Lin, Q.; Qu, L.; Lü, Q.; Fang, C. Preparation and properties of graphene oxide nanosheets/cyanate ester resin composites. Polym. Test. 2013, 32, 330–337. [Google Scholar] [CrossRef]
- Xu, W.; Zhang, B.; Wang, X.; Wang, G.; Ding, D. The flame retardancy and smoke suppression effect of a hybrid containing CuMoO4 modified reduced graphene oxide/layered double hydroxide on epoxy resin. J. Hazard. Mater. 2018, 343, 364–375. [Google Scholar] [CrossRef]
- Li, Z.; González, A.J.; Heeralal, V.B.; Wang, D.Y. Covalent assembly of MCM-41 nanospheres on graphene oxide for improving fire retardancy and mechanical property of epoxy resin. Compos. B Eng. 2018, 138, 101–112. [Google Scholar] [CrossRef]
- Fang, F.; Song, P.; Ran, S.; Guo, Z.; Wang, H.; Fang, Z. A facile way to prepare phosphorus-nitrogen-functionalized graphene oxide for enhancing the flame retardancy of epoxy resin. Compos. Commun. 2018, 10, 97–102. [Google Scholar] [CrossRef]
- Azimi, R.; Roghani-Mamaqani, H.; Gholipour-Mahmoudalilou, M. Grafting poly (amidoamine) dendrimer-modified silica nanoparticles to graphene oxide for preparation of a composite and curing agent for epoxy resin. Polymer 2017, 126, 152–161. [Google Scholar] [CrossRef]
- Tang, X.; Zhou, Y.; Peng, M. Green preparation of epoxy/graphene oxide nanocomposites using a glycidylamine epoxy resin as the surface modifier and phase transfer agent of graphene oxide. ACS Appl. Mater. Int. 2016, 8, 1854–1866. [Google Scholar] [CrossRef]
- Li, J.; Fan, W.; Ma, Y.; Xue, L.; Yuan, L.; Dang, W.; Meng, J. Influence of Reinforcement Structures and Hybrid Types on Inter-Laminar Shear Performance of Carbon-Glass Hybrid Fibers/Bismaleimide Composites under Long-Term Thermo-Oxidative Aging. Polymers 2019, 11, 1288. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Guo, L.; Yan, H.; Chen, Z.; Liu, Q.; Feng, Y.; Ding, F.; Nie, Y. Amino functionalization of reduced graphene oxide/tungsten disulfide hybrids and their bismaleimide composites with enhanced mechanical properties. Polymers 2018, 10, 1199. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Xu, M.; Lei, Y.; Ren, D.; Chen, L.; Li, K.; Liu, X. Thermal stability of allyl-functional phthalonitriles-containing benzoxazine/bismaleimide copolymers and their improved mechanical properties. Polymers 2018, 10, 596. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Polgar, L.M.; Hagting, E.; Koek, W.J.; Picchioni, F.; Van-Duin, M. Thermoreversible cross-linking of furan-containing ethylene/vinyl acetate rubber with bismaleimide. Polymers 2017, 9, 81. [Google Scholar] [CrossRef] [Green Version]
- Liu, C.; Dong, Y.; Lin, Y.; Yan, H.; Zhang, W.; Bao, Y.; Ma, J. Enhanced mechanical and tribological properties of graphene/bismaleimide composites by using reduced graphene oxide with non-covalent functionalization. Compos. B Eng. 2019, 165, 491–499. [Google Scholar] [CrossRef]
- Ma, W.S.; Li, J.; Deng, B.J.; Zhao, X.S. Preparation and characterization of long-chain alkyl silane-functionalized graphene film. J. Mater. Sci. 2013, 48, 156–161. [Google Scholar] [CrossRef]
- Yu, J.W.; Jung, J.; Choi, Y.M.; Choi, J.H.; Yu, J.; Lee, J.K.; You, N.H.; Goh, M. Enhancement of the crosslink density, glass transition temperature, and strength of epoxy resin by using functionalized graphene oxide co-curing agents. Polym. Chem. 2016, 7, 36–43. [Google Scholar] [CrossRef]
- Jiang, H.; Wang, R.; Farhan, S.; Zheng, S. Improved thermosets obtained from diglycidyl ether of bisphenol A/4,4′-diaminodiphenylsulfone based on a new epoxy-terminated hyperbranched polymer. Polym. Int. 2015, 64, 1794–1800. [Google Scholar] [CrossRef]
- Jiang, H.; Wang, R.; Farhan, S.; Zhang, D.; Zheng, S. Curing behavior and thermal and mechanical properties enhancement of tetraglycidyl-4,4′-diaminodiphenylmethane/4,4′-diaminodiphenyl- sulfone using a liquid crystalline epoxy. Polym. Int. 2016, 65, 430–438. [Google Scholar] [CrossRef]
- Wan, Y.J.; Gong, L.X.; Tang, L.C.; Wu, L.B.; Jiang, J.X. Mechanical properties of epoxy composites filled with silane-functionalized graphene oxide. Compos. Part A Appl. Sci. Manuf. 2014, 64, 79–89. [Google Scholar] [CrossRef]
- Liu, Y.; Wu, K.; Luo, F.; Lu, M.; Xiao, F.; Du, X.; Zhang, S.; Liang, L.; Lu, M. Significantly enhanced thermal conductivity in polyvinyl alcohol composites enabled by dopamine modified graphene nanoplatelets. Compos. Part A Appl. Sci. Manuf. 2019, 117, 134–143. [Google Scholar] [CrossRef]
- Yarahmadi, E.; Didehban, K.; Sari, M.G.; Saeb, M.R.; Shabanian, M.; Aryanasab, F.; Zarrintaj, P.; Paran, S.M.R.; Mozafari, M.; Rallini, M.; et al. Development and curing potential of epoxy/starch-functionalized graphene oxide nanocomposite coatings. Prog. Org. Coat. 2018, 119, 194–202. [Google Scholar] [CrossRef]
ES-GO Content (wt.%) | Thermogravimetric Analysis (TGA) Data | Tg (°C) | HDT (°C) | |||
---|---|---|---|---|---|---|
T0.05 (°C) | Tmax (°C) | Char Yield at 850 °C (%) | DSC | DMA | ||
0 | 446 | 535 | 28.6 | 287 | 305 | 269 |
0.1 | 449 | 566 | 31.2 | 300 | 313 | 274 |
0.3 | 448 | 582 | 32.4 | 310 | 325 | 290 |
0.5 | 450 | 590 | 35.6 | 316 | 332 | 292 |
ES-GO Content (wt.%) | Flexural Strength (MPa)/Retention Rate | Shear Strength (MPa)/Retention Rate | ||||
---|---|---|---|---|---|---|
A | B | C | A | B | C | |
0 | 638 | 551/86.3% | 611/95.7% | 58.4 | 49.2/84.2% | 54.7/93.6% |
0.1 | 692 | 591/87.4% | 656/95.8% | 61.5 | 50.6/86.3% | 56.1/94.3% |
0.3 | 791 | 645/87.6% | 740/96.7% | 68.8 | 53.2/87.8% | 60.8/95.4% |
0.5 | 757 | 688/88.3% | 793/96.5% | 62.6 | 56.9/88.2% | 65.8/95.9% |
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Jiang, H.; Ji, Y.; Gan, J.; Wang, L. Enhancement of Thermal and Mechanical Properties of Bismaleimide Using a Graphene Oxide Modified by Epoxy Silane. Materials 2020, 13, 3836. https://doi.org/10.3390/ma13173836
Jiang H, Ji Y, Gan J, Wang L. Enhancement of Thermal and Mechanical Properties of Bismaleimide Using a Graphene Oxide Modified by Epoxy Silane. Materials. 2020; 13(17):3836. https://doi.org/10.3390/ma13173836
Chicago/Turabian StyleJiang, Hao, Yanyan Ji, Jiantuo Gan, and Lei Wang. 2020. "Enhancement of Thermal and Mechanical Properties of Bismaleimide Using a Graphene Oxide Modified by Epoxy Silane" Materials 13, no. 17: 3836. https://doi.org/10.3390/ma13173836