Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking

Chao-En Jin; Hua-Mei Zhu; Lei Wang; Fan Wang; Ya-Ping Zhu; Shi-Feng Deng; Hui-Min Qi; Lei Du

doi:10.1007/s10118-024-3173-x

Your Location：

Home >

Browse articles >

Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking

RESEARCH ARTICLE | Updated：2024-11-04

- Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking
- Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking
- 高分子科学（英文版） 2024年42卷第11期页码：1719-1729
- Affiliations：
  
  Key Laboratory of Specially Functional Polymeric Materials and Related Technology of Ministry of Education, School of Materials Science and Engineering, East China University of Science & Technology, Shanghai 200237, China
- Author bio：
  
  qihm@ecust.edu.cn
- Funds：
  
  This work was financially supported by the Key Laboratory of Specially Functional Polymeric Materials and Related Technology of Ministry of Education, East China University of Science & Technology, and the Fundamental Research Funds for the Central Universities (Nos. 50321041918013 and 50321041917001).;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-024-3173-x.
- DOI：10.1007/s10118-024-3173-x
  中图分类号：
- 收稿：2024-03-19，
  
  修回：2024-05-09，
  
  录用：2024-05-22，
  
  网络首发：2024-08-20，
  
  纸质出版：2024-11-30
- Accepted：
Scan QR Code
Jin, C. E.; Zhu, H. M.; Wang, L.; Wang, F.; Zhu, Y. P.; Deng, S. F.; Qi, H. M.; Du, L. Preparation and characterization of cyano-silicon-containing arylacetylene resins and their composites: dual enhancement strategy involving physical interfacial interactions and chemical crosslinking. Chinese J. Polym. Sci. 2024, 42, 1719–1729

Chao-En Jin, Hua-Mei Zhu, Lei Wang, et al. Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking[J]. Chinese Journal of Polymer Science, 2024, 42(11): 1719-1729.
Jin, C. E.; Zhu, H. M.; Wang, L.; Wang, F.; Zhu, Y. P.; Deng, S. F.; Qi, H. M.; Du, L. Preparation and characterization of cyano-silicon-containing arylacetylene resins and their composites: dual enhancement strategy involving physical interfacial interactions and chemical crosslinking. Chinese J. Polym. Sci. 2024, 42, 1719–1729 DOI： 10.1007/s10118-024-3173-x.

Chao-En Jin, Hua-Mei Zhu, Lei Wang, et al. Preparation and Characterization of Cyano-Silicon-Containing Arylacetylene Resins and Their Composites: Dual Enhancement Strategy Involving Physical Interfacial Interactions and Chemical Crosslinking[J]. Chinese Journal of Polymer Science, 2024, 42(11): 1719-1729. DOI： 10.1007/s10118-024-3173-x.

摘要

The cyclization reaction between the cyano and alkyne groups

as well as the strong polarity of the cyano group

provides the cyano-silicon-containing arylacetylene resins with a dual enhancement mechanism of chemical cross-linking and physical interactions

resulting in the mechanical properties of their composites improved while maintaining excellent heat resistance.

Abstract

Silicon-containing arylacetylene (PSA) resins have broad application prospects because of their excellent heat resistance. However

improving their mechanical properties and interfacial bonding with reinforcement fibers while maintaining heat resistance is a challenge in engineering applications. Here

poly(diethynylbenzene-methylsilyl-3-benzonitrile) (DEB-CN) and poly(diethynylbenzene-methylsilyl-3

6-diethynylcarbazole-3-benzonitrile) (DEC-CN) were synthesized

via

an isopropylmagnesium chloride lithium-chloride complex (

-PrMgCl·LiCl)

overcoming the compatibility problem between cyano groups and Grignard reagents. The cyano and alkyne groups in the resin underwent cyclization to form pyridine

catalyzed by the -NH- moiety in DEC-CN

resulting in extremely high thermal stability (5% weight loss temperature: 669.3 °C

glass transition temperature

650 °C). The combination of cyano dipole-dipole pairing and hydrogen bonding greatly enhanced the resin-fiber interface properties

while the generated pyridine promoted stress relief in the crosslinked network

substantially improving the mechanical properties of the cyano-silicon-containing arylacetylene resin composites. The flexural strength of quartz fiber cloth/DEC-CN composites was 298.2 MPa at room temperature and 145.9 MPa at 500 °C

corresponding to 84.0% and 127.6% enhancements

respectively

over the cyano-free counterpart. These cyano-silicon-containing arylacetylene resins exhibited a dual reinforcement mechanism involving physical interfacial interactions and chemical crosslinking

achieving a good balance between thermal stability and mechanical properties.

关键词

Keywords

references

Li, Q.; Chen, L.; Gadinski, M. R.; Zhang, S.; Zhang, G.; Li, H. U.; Iagodkine, E.; Haque, A.; Chen, L. Q.; Jackson, T. N.; Wang, Q. Flexible high-temperature dielectric materials from polymer nanocomposites. Nature 2015 , 523 , 576−579..

Shen, Y.; Wang, S.; Du, G.; Qin, T.; Jiang, S.; Liu, S.; Duan, Z.; Niu, H.; Li, T. Laminated composite fabricated using high-performance polyamine thermoset: ultra heat resistance and excellent mechanical property. Compos. Part B: Eng. 2024 , 272 , 111209..

Tang, L.; Zhang, J.; Wu, C.; Tang, Y.; Ma, H.; Kong, J.; Gu, J. UV etched random copolymer membrane coated PBO fibers/cyanate ester wave-transparent laminated composites. Compos. Part B: Eng. 2021 , 212 , 108680..

Guo, K.; Li, P.; Zhu, Y.; Wang, F.; Qi, H. Thermal curing and degradation behaviour of silicon-containing arylacetylene resins. Polym. Degrad. Stabil. 2016 , 131 , 98−105..

Itoh, M.; Inoue, K.; Iwata, K.; Ishikawa, J.; Takenaka, Y. A heat-resistant silicon-based polymer. Adv. Mater. 1997 , 9 , 1187−1190..

Itoh, M.; Inoue, K.; Iwata, K.; Mitsuzuka, M.; Kakigano, T. New highly heat-resistant polymers containing silicon: poly(silyleneethynylenephenyleneethynylene)s. Macromolecules 1997 , 30 , 694−701..

Itoh, M.; Mitsuzuka, M.; Iwata, K.; Inoue, K. A Novel synthesis and extremely high thermal stability of poly[(phenylsilylene)ethynylene-1,3-phenyleneethynylene ] . Macromolecules 1994 , 27 , 7917−7919..

Lu, L.; Guo, K.; Zhu, J.; Wang, F.; Zhu, Y.; Qi, H. Silicon-containing fluorenylacetylene resins with low curing temperature and high thermal stability. J. Appl. Polym. Sci. 2019 , 136 , 48262..

Zhang, S.; Du, S.; Wang, L.; Lin, J.; Du, L.; Xu, X.; Gao, L. Design of sil icon-containing arylacetylene resins aided by machine learning enhanced materials genome approach. Chem. Eng. J. 2022 , 448 , 137643..

Song, S.; Zhang, S.; Cai, C.; Lin, J.; Du, L. Preparation and performance of poly(silicon-alkyne imide) resins and their composites. J. Funct. Polym. 2021 , 34 , 497−505..

Feng, P.; Ma, L.; Zhou, X.; Li, M.; Zhang, Q.; Zhang, M.; Liu, X.; Jian, X.; Xu, J. Constructing a gradient modulus interface layer on the surface of carbon fibers to enhance the mechanical properties of carbon fiber/epoxy composites at different temperatures. Compos. Part B: Eng. 2024 , 271 , 111190..

Bu, X.; Zhou, Y.; Huang, F. The strengthening and toughening effects of a novel octa(propargyl propyl sulfide) POSS (OPPSP) on silicon-containing arylacetylene (PSA) resin. Mater. Lett. 2016 , 174 , 21−23..

Gao, Y.; Zhou, Y.; Huang, F.; Du, L. Preparation and properties of silicon-containing arylacetylene resin/benzoxazines blends. High Perform. Polym. 2013 , 25 , 445−453..

Li, Q .; Zhou, Y.; Hang, X.; Deng, S.; Huang, F.; Du, L.; Li, Z. Synthesis and characterization of a novel arylacetylene oligomer containing POSS units in main chains. Eur. Polym. J. 2008 , 44 , 2538−2544..

Gao, G.; Zhang, S.; Wang, L.; Lin, J.; Qi, H.; Zhu, J.; Du, L.; Chu, M. Developing highly tough, heat-resistant blend thermosets based on silicon-containing arylacetylene: a material genome approach. ACS Appl. Mater. Interfaces 2020 , 12 , 27587−27597..

Huang, J.; Du, W.; Zhang, J.; Huang, F.; Du, L. Study on the copolymers of silicon-containing arylacetylene resin and acetylene-functional benzoxazine. Polym. Bull. 2009 , 62 , 127−138..

Kimura, H.; Okita, K.; Ichitani, M.; Sugimoto, T.; Kuroki, S.; Ando, I. Structural study of silyl-carborane hybrid diethynylbenzene-silylene polymers by high-resolution solid-state 11 B, 13 C, and 29 Si NMR spectroscopy. Chem. Mater. 2003 , 15 , 355−362..

Li, J.; Zhao, H.; Cao, Q.; Zeng, W.; Zhang, J.; Guo, Y.; Zhao, Y.; Jian, X.; Weng, Z. Synthesis of cyano-containing epoxy precursor from vanillin for engineering multifaceted performance-enhancing resins. ACS Sustainable Chem. Eng. 2023 , 11 , 9528−9539..

Liu, B.; Xu, Z.; Gao, H.; Fan, C.; Ma, G.; Zhang, D.; Xiao, M.; Zhang, B.; Yang, Y.; Cui, C.; Wu, T.; Feng, X.; Liu, W. Stiffness self-tuned shape memory hydrogels for embolization of aneurysms. Adv. Funct. Mater. 2020 , 30 , 1910197..

Chen, Z.; Wang, L.; Lin, J.; Du, L. A theoretical insight into the curing mechanism of phthalonitrile resins promoted by aromatic amines. Phys. Chem. Chem. Phys. 2021 , 23 , 17300−17309..

Peng, W.; Yao, F.; Hu, J.; Liu, Y.; Lu, Z.; Liu, Y.; Liu, Z.; Zeng, K.; Yang, G. Renewable protein-based monomer for thermosets: a case study on phthalonitrile resin. Green Chem. 2018 , 20 , 5158−5168..

Gu, H.; Gao, C.; Du, A.; Guo, Y.; Zhou, H.; Zhao, T.; Naik, N.; Guo, Z. An overview of high-performance phthalonitrile resins: fabrication and electronic applications. J. Mater. Chem. C 2022 , 10 , 2925−2937..

Huo, X.; Guo, K.; Wang, F.; Zhu, Y.; Qi, H. Preparation of hybrid cyanate ester resin in the presence of polysilazane and its properties. High Perform. Polym. 2020 , 33 , 184−195..

Sun, B. G.; Lei, Q.; Guo, Y.; Shi, H. Q.; Sun, J. B.; Yang, K. X.; Zhou, H.; Li, Y. Q.; Hu, N.; Wang, H.; Fu, S. Y. Enhanced mechanical properties at 400 °C of carbon fabric reinforced phthalonitrile composites by high temperature postcure. Compos. Part B: Eng. 2019 , 166 , 681−687..

Tang, L.; Zhang, J.; Tang, Y.; Zhou, Y.; Lin, Y.; Liu, Z.; Kong, J.; Liu, T.; Gu, J. Fluorine/adamantane modified cyanate resins with wonderful interfacial bonding strength with PBO fibers. Compos. Part B: Eng. 2020 , 186 , 107827..

Wang, G.; Guo, Y.; Han, Y.; Li, Z.; Ding, J.; Jiang, H.; Zhou, H.; Zhao, T. Enhanced properties of phthalonitrile resins reinforced by novel phthalonitrile-terminated polyaryl ether nitrile containing fluorene group. High Perform. Polym. 2019 , 32 , 3−11..

Zhou, Z. X.; Li, Y.; Zhong, J.; Luo, Z.; Gong, C. R.; Zheng, Y. Q.; Peng, S.; Yu, L. M.; Wu, L.; Xu, Y. High-performance cyanate ester resins with interpenetration networks for 3D printing. ACS Appl. Mater. Interfaces 2020 , 12 , 38682−38689..

Wang, M.; Ning, Y. Oligosilylarylnitrile: The thermoresistant thermosetting resin with high comprehensive properties. ACS Appl. Mater. Interfaces 2018 , 10 , 11933−11940..

Hashimoto, T.; Kato, K.; Yano, R.; Natori, T.; Miura, H.; Takeuchi, R. Iridium-catalyzed synthesis of acylpyridines by [2+2+2 ] cycloaddition of diynes with acyl cyanides. J. Org. Chem. 2016 , 81 , 5393−5400..

Medas, K. M.; Lesch, R. W.; Edioma, F. B.; Wrenn, S. P.; Ndahayo, V.; Mulcahy, S. P. Metal-catalyzed cyclotrimerization reactions of cyanamides: synthesis of 2-aryl- α -carbolines. Org. Lett. 2020 , 22 , 3135−3139..

Wang, C. S.; Sun, Q.; García, F.; Wang, C.; Yoshikai, N. Robust cobalt catalyst for nitrile/alkyne [2+2+2 ] cycloaddition: synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics. Angew. Chem. Int. Ed. 2021 , 60 , 9627−9634..

Li, C.; Ma, M.; Tang, J.; Yuan, Q.; Huang, F. Enhanced properties of poly(silylene phenylether arylacetylene) by a side cyano group. Polym. Eng. Sci. 2022 , 62 , 2900−2908..

Chen, F.; Dong, S.; Zhao, C.; Hu, W.; Wang, G.; Hu, Y.; Deng, S. A novel one-step synthesis of silicon-containing arylacetylene resin catalyzed by Et 2 Zn with excellent processability and thermal properties. ChemistrySelect 2022 , 7 , e202200133..

Jiang, J.; Yin, C.; Xing, S.; Wu, N.; Zhang, F.; Tang, J. Amine-containing phthalonitrile catalyst for cyanate esters with high catalytic activity and low side effects. ACS Appl. Polym. Mater. 2023 , 5 , 7899−7906..

Ye, J.; Li, Q.; Zhang, S.; Liu, X. Melamine modified phthalonitrile resins: synthesis, polymerization and properties. Polymer 2022 , 256 , 125156..

Zhu, Z.; He, X.; Tan, W.; Hong, J.; Liao, S.; Lv, J.; Zeng, K.; Hu, J.; Yang, G. A new class of high-performance thermoset resins using dicyanoimidazole (DCI) as crosslinking group: a key demo of synthesis, curing behavior and thermal properties. Polymer 2021 , 235 , 124264..

Zhou, J.; Guo, K.; Wang, F.; Zhu, Y.; Qi, H. Cure behavior and mechanism of cyanate ester with aromatic amines at room temperature. High Perform. Polym. 2023 , 35 , 977−990..

Wan, L.; Guo, K.; Zhu, J.; Wang, F.; Zhu, Y.; Deng, S.; Qi, H. Improvement of the oxidation resistanceof silicon-containing arylacetylene resins upon the introduction of carbazoles. J. Appl. Polym. Sci. 2021 , 138 , 49642..

Liu, X.; Ma, M.; Li, C.; Tang, J.; Yuan, Q.; Huang, F. Effect of side groups on the properties of silicon-containing arylacetylene resins. Polym. Eng. Sci. 2022 , 62 , 793−801..

Tinson, R. A. J.; Hughes, D. L.; Ward, L.; Stephenson, G. R. Unusual nucleophilic addition of grignard reagents in the synthesis of 4-amino-pyrimidines. ACS Omega 2018 , 3 , 8937−8944..

Krasovskiy, A.; Knochel, P. A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides. Angew. Chem. Int. Ed. 2004 , 43 , 3333−3336..

Piller, F. M.; Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel, P. Convenient preparation of polyfunctional aryl magnesium reagents by a direct magnesium insertion in the presence of LiCl. Angew. Chem. Int. Ed. 2008 , 47 , 6802−6806..

Dong, S.; Hu, X.; Yuan, Q.; Huang, F. An easy-to-process poly(silylene-acetylene) terminated by reactive ethynylphenyl: synthesis, properties and composites. React. Funct. Polym. 2022 , 170 , 105099..

Ke, H.; Zhao, L.; Zhang, X.; Qiao, Y.; Wang, G.; Wang, X. Performance of high-temperature thermosetting polyimide composites modified with thermoplastic polyimide. Polym. Test. 2020 , 90 , 106746..

Lin, D.; Li, R.; Li, T.; Zi, Y.; Qi, S.; Wu, D. Effects of pre-imidization on rheological behaviors of polyamic acid solution and thermal mechanical properties of polyimide film: an experiment and molecular dynamics simulation. J. Mater. Sci. 2021 , 56 , 14518−14530..

Pu, Y.; Xie, H.; He, X.; Lv, J.; Zhu, Z.; Hong, J.; Zeng, K.; Hu, J.; Yang, G. The curing reaction of phthalonitrile promoted by sulfhydryl groups with high curing activity. Polymer 2022 , 252 , 124948..

Zhan, S. Y.; Han, Y.; Wu, Y. H.; Ding, J. N.; Liu, X.; Guo, Y.; Zhou, H.; Zhao, T. Bo ron-containing phthalonitrile resin: Synthesis, curing behavior, and thermal properties. Chinese J. Polym. Sci. 2022 , 40 , 1349−1359..

You, X.; Deng, S.; Huang, Y.; Liu, Z.; Hu, Y. Thermosetting mechanism study of silicon-containing polyarylacetylene via in situ FTIR and solid-state NMR spectroscopy. J. Appl. Polym. Sci. 2019 , 136 , 47301..

Liu, Y.; Yue, Z.; Gao, J. Synthesis, characterization, and thermally activated polymerization behavior of bisphenol-S/aniline based benzoxazine. Polymer 2010 , 51 , 3722−3729..

Chen, M.; Xiong, P.; Zhou, Q.; Ni, L.; Wang, G. Synthesis, curing behavior and thermal properties of silicon-containing hybrid polymers with Si−C≡C units. Polym. Int. 2014 , 63 , 1531−1536..

Ryan, M. J.; Yang, N.; Kwac, K.; Wilhelm, K. B.; Chi, B. K.; Weix, D. J.; Cho, M.; Zanni, M. T. The hydrogen-bonding dynamics of water to a nitrile-functionalized electrode is modulated by voltage according to ultrafast 2D IR spectroscopy. Proc. Natl. Acad. Sci. U. S. A. 2023 , 120 , e2314998120..

Jin, C.; Wang, F.; Zhu, Y.; Deng, S.; Qi, H.; Du, L. Thermal oxidation behavior and mechanisms for silicon-containing arylacetylene resins: experimental and reactive force field molecular dynamics simulations. ACS Appl. Polym. Mater. 2024 , 6 , 1962−1972..

Gong, C.; Huang, X.; Li, J.; Lv, S.; Zhou, Y.; Tang, J.; Huang, F. Perfluorocyclobutyl aryl ether-based poly(silylene arylacetylene)s with a low dielectric constant for advanced wave-transparent composites. Eur. Polym. J. 2022 , 181 , 111655..

Gong, C.; Huang, X.; Lv, S.; Li, J.; Tang, J.; Huang, F. Poly(silylene arylacetylene)s containing hexafluoroisopropylidene with attractive mechanical properties and dielectric performance for wave-transparent composites. Mater. Chem. Front. 2023 , 7 , 5015−5027..

浏览量

211

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Improvements of Hydrophobicity and Toughness of Epoxy Coatings Modified with Hydroxyl-terminated Fluororubber

Effects of Different Nucleating Agents, Annealing and Pre-stretching Process on the Crystallinity and Mechanical Properties of Poly(butylene carbonate)

Advancing the Thin-film Mechanics of Conjugated Polymers: Characterization, Modulation, and Innovation

Enhanced Mechanical Properties and Prolonged Recovery Onset Period of Timed Shape Memory Hydrogels via Hydrophobic Interaction

From Molecular Defect to Macroscopic Performance: Manipulating Dichroism and Mechanics in Iodine-doped Poly(vinyl alcohol) via Ethylene Incorporation