Volume 40 Issue 1
Jan.  2023
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LIU Yi, MO Song, XU Xiaozhou, et al. Organic/inorganic hybrid polyimide matrix resins with high temperature resistance[J]. Acta Materiae Compositae Sinica, 2023, 40(1): 62-71. doi: 10.13801/j.cnki.fhclxb.20220415.002
Citation: LIU Yi, MO Song, XU Xiaozhou, et al. Organic/inorganic hybrid polyimide matrix resins with high temperature resistance[J]. Acta Materiae Compositae Sinica, 2023, 40(1): 62-71. doi: 10.13801/j.cnki.fhclxb.20220415.002

Organic/inorganic hybrid polyimide matrix resins with high temperature resistance

doi: 10.13801/j.cnki.fhclxb.20220415.002
  • Received Date: 2022-01-18
  • Accepted Date: 2022-04-10
  • Rev Recd Date: 2022-03-25
  • Available Online: 2022-04-19
  • Publish Date: 2023-01-15
  • Thermosetting polyimide resin matrix composites have been widely used in aerospace industry, but the heat resistance of traditional organic polyimide matrix resins is gradually insufficient to satisfy the design and application requirement of the aircrafts, with the development of aerospace technology. Therefore, novel organic/inorganic hybrid polyimides resistant to higher temperature have become the focus of research. In this paper, the recent progress of organic/inorganic hybrid polyimide matrix resins was summarized. The synthetic pathway, structure design, performance control, curing process and degradation behavior of polyhedral oligomeric silsesquioxane-containing polyimide, carborane-containing polyimide and siloxane-containing polyimide were reviewed, providing a detailed description of the characteristics and thermo-resistant mechanism of the organic/inorganic hybrid polyimide resins. The challenges and opportunities for the future development of organic/inorganic hybrid polyimide resins were also discussed and analyzed.

     

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  • [1]
    LIAW D J, WANG K L, HUANG Y C, et al. Advanced polyimide materials: Syntheses, physical properties and applications[J]. Progress in Polymer Science,2012,37(7):907-974. doi: 10.1016/j.progpolymsci.2012.02.005
    [2]
    GOUZMAN I, GROSSMAN E, VERKER R, et al. Advances in polyimide-based materials for space applications[J]. Advanced Materials,2019,31(18):1807738. doi: 10.1002/adma.201807738
    [3]
    赵伟栋, 王磊, 潘玲英, 等. 聚酰亚胺复合材料研究进展[J]. 宇航材料工艺, 2013, 43(4):14-19. doi: 10.3969/j.issn.1007-2330.2013.04.004

    ZHAO Weidong, WANG Lei, PAN Lingying, et al. Recent advances in polyimide matrix structural composites[J]. Aerospace Materials and Technology,2013,43(4):14-19(in Chinese). doi: 10.3969/j.issn.1007-2330.2013.04.004
    [4]
    赵云峰, 潘玲英. 航天先进结构复合材料及制造技术研究进展[J]. 宇航材料工艺, 2021, 51(4):29-36. doi: 10.12044/j.issn.1007-2330.2021.04.004

    ZHAO Yunfeng, PAN Lingying. Research progress of aerospace advanced polymer matrix composites and manufacturing technology[J]. Aerospace Materials and Technology,2021,51(4):29-36(in Chinese). doi: 10.12044/j.issn.1007-2330.2021.04.004
    [5]
    包建文, 陈祥宝. 发动机用耐高温聚酰亚胺树脂基复合材料的研究进展[J]. 航空材料学报, 2012, 32(6):1-13. doi: 10.3969/j.issn.1005-5053.2012.6.001

    BAO Jianwen, CHEN Xiangbao. Advance in high temperature polyimide resin matrix composites for aeroengine[J]. Journal of Aeronautical Materials,2012,32(6):1-13(in Chinese). doi: 10.3969/j.issn.1005-5053.2012.6.001
    [6]
    邢丽英, 包建文, 礼嵩明, 等. 先进树脂基复合材料发展现状和面临的挑战[J]. 复合材料学报, 2016, 33(7):1327-1338.

    XING Liying, BAO Jianwen, LI Chongming, et al. Development status and facing challenge of advanced polymer matrix composites[J]. Acta Materiae Compositae Sinica,2016,33(7):1327-1338(in Chinese).
    [7]
    阎敬灵, 孟祥胜, 王震, 等. 热固性聚酰亚胺树脂研究进展[J]. 应用化学, 2015, 32(5):9-17.

    YAN Jingling, MENG Xiangsheng, WANG Zhen, et al. Progress in thermosetting polyimide resins[J]. Chinese Journal of Applied Chemistry,2015,32(5):9-17(in Chinese).
    [8]
    高禹, 李洋洋, 王柏臣, 等. 先进树脂基复合材料在航空发动机上的应用及研究进展[J]. 航空制造技术, 2016(21):16-21.

    GAO Yu, LI Yangyang, WANG Bochen, et al. Application of advaced resin matrix composites in aeroengine and its research progress[J]. Aeronautical Manufacturing Technology,2016(21):16-21(in Chinese).
    [9]
    王倩倩, 周燕萍, 郑会保, 等. 耐高温聚酰亚胺树脂及其复合材料的研究及应用[J]. 工程塑料应用, 2019, 47(8):144-147. doi: 10.3969/j.issn.1001-3539.2019.08.030

    WANG Qianqian, ZHOU Yanping, ZHENG Huibao, et al. Research and application of high temperature polyimide and its composite materials[J]. Engineering Plastics Application,2019,47(8):144-147(in Chinese). doi: 10.3969/j.issn.1001-3539.2019.08.030
    [10]
    薛书宇, 雷星锋, 连如贺, 等. 高性能热固性聚酰亚胺树脂研究进展[J]. 高分子材料科学与工程, 2021, 37(5):149-162.

    XUE Shuyu, LEI Xingfeng, LIAN Ruhe, et al. Progress of high-performance thermosetting polyimide resins[J]. Polymer Materials Scinece and Engineering,2021,37(5):149-162(in Chinese).
    [11]
    HADDAD T S, LICHTENHAN J D. Hybrid organic-inorganic thermoplastics: Styryl-based polyhedral oligomeric silsesquioxane polymers[J]. Macromolecules,1996,29(22):7302-7304. doi: 10.1021/ma960609d
    [12]
    TSUCHIDA A, BOLLN C, SERNETZ F G, et al. Ethene and propene copolymers containing silsesquioxane side groups[J]. Macromolecules,1997,30(10):2818-2824. doi: 10.1021/ma960846g
    [13]
    WRIGHT M E, SCHORZMAN D A, FEHER F J, et al. Synthesis and thermal curing of aryl-ethynyl-terminated coPOSS imide oligomers: New inorganic/organic hybrid resins[J]. Chemisty of Materials,2003,15(1):264-268. doi: 10.1021/cm020238h
    [14]
    NEYERTZ S, BROWN D, RAAIJMAKERS M J T, et al. A molecular characterization of hyper-cross-linked hybrid polyPOSS-imide networks[J]. Computational Materials Science,2016,117:338-353. doi: 10.1016/j.commatsci.2016.02.015
    [15]
    HUANG J C, HE C B, XIAO Y, et al. Polyimide/POSS nanocomposites: Interfacial interaction, thermal properties and mechanical properties[J]. Polymer,2003,44(16):4491-4499. doi: 10.1016/S0032-3861(03)00434-8
    [16]
    LEE A. Durability characterization of POSS-based polyimides and carbon-fiber composites for air force-related applications, ADA482151[R]. Washington: NASA, 2007.
    [17]
    SEURER B, VIJ V, HADDAD T, et al. Thermal transitions and reaction kinetics of polyhederal silsesquioxane containing phenylethynyl-phthalimides[J]. Macromolecules,2010,43(22):9337-9347. doi: 10.1021/ma101640q
    [18]
    FINA A, TABUANI D, CARNIATO F, et al. Polyhedral oligomeric silsesquioxanes (POSS) thermal degradation[J]. Thermochimica Acta,2006,440(1):36-42. doi: 10.1016/j.tca.2005.10.006
    [19]
    MOORE L M J, ZAVALA J J, LAMB J T, et al. Bis-phenylethynyl polyhedral oligomeric silsesquioxanes: New high-temperature, processable thermosetting materials[J]. RSC Advances,2018,8(48):27400-27405. doi: 10.1039/C8RA05954C
    [20]
    刘仪, 莫松, 潘玲英, 等. 耐高温有机无机杂化聚酰亚胺树脂及其复合材料[J]. 宇航材料工艺, 2018, 48(3):1-5. doi: 10.12044/j.issn.1007-2330.2018.03.001

    LIU Yi, MO Song, PAN Lingying, et al. Organic/inorganic hybrid polyimides and their composites with high temperature resistance[J]. Aerospace Materials and Technology,2018,48(3):1-5(in Chinese). doi: 10.12044/j.issn.1007-2330.2018.03.001
    [21]
    VIJ V, HADDAD T S, YANDEK G R, et al. Synthesis of aromatic polyhedral oligomeric silsesquioxane (POSS) dianilines for use in high-temperature polyimides[J]. Silicon,2012,4(4):267-280. doi: 10.1007/s12633-012-9130-2
    [22]
    PINSON D M, YANDEK G R, HADDAD T S, et al. Thermosetting poly(imide silsesquioxane)s featuring reduced moisture affinity and improved processability[J]. Macromolecules,2013,46(18):7363-7377. doi: 10.1021/ma401347q
    [23]
    BREGADZE V I. Dicarba-closo-dodecaboranes C2B10H12 and their derivatives[J]. Chemical Reviews,1992,92(2):209-223. doi: 10.1021/cr00010a002
    [24]
    OHTA K, GOTO T, ENDO Y. New synthetic method of 1, 2-diaryl-1, 2-dicarba-closo-dodecaboranes employing aromatic nucleophilic substitution (SNAr) reaction[J]. Tetrahedron Letters,2005,46(3):483-485. doi: 10.1016/j.tetlet.2004.11.074
    [25]
    WU Y N, FENG C, YANG J P, et al. High thermally stable thermosetting polyimides derived from a carborane-containing tetramine[J]. High Performance Polymers,2019,31(5):548-556. doi: 10.1177/0954008318779429
    [26]
    YUE J, LI Y T, LI H, et al. Thermal curing of novel carborane-containing phenylethynyl terminated imide oligomers[J]. RSC Advances,2015,5(119):98010-98019. doi: 10.1039/C5RA15743A
    [27]
    YUE J, LI Y T, ZHAO Y, et al. Thermal degradation behavior of carborane-containing phenylethynyl terminated imide systems[J]. Polymer Degradation and Stability,2016,129:286-295. doi: 10.1016/j.polymdegradstab.2016.05.006
    [28]
    WU Y N, YANG J P, CHEN G. Synthesis and characterization of a carborane-containing monofunctional imide monomer as a modifier for imide oligomer[J]. High Performance Polymers,2018,30(7):812-820. doi: 10.1177/0954008317731504
    [29]
    CHENG S L, HAN J H, WANG X, et al. Oxidatively stable thermosets derived from thermal copolymerization of acetylene-terminated imide monomer with an acetylenic monomer containing carborane[J]. Polymer,2017,115:96-105. doi: 10.1016/j.polymer.2017.02.070
    [30]
    WU Y E, CHEN G, FENG C, et al. High Tg and thermo-oxidatively stable thermosetting polyimides derived from a carborane-containing diamine[J]. Macromolecular Rapid Communications,2018,39(21):1800484. doi: 10.1002/marc.201800484
    [31]
    WU Y E, CHEN G, ZHAN M S, et al. High heat resistant carbon fiber/polyimide composites with neutron shielding performance[J]. Progress in Organic Coatings,2019,132:184-190. doi: 10.1016/j.porgcoat.2019.03.047
    [32]
    ZHANG X L, DAI H M, YAN H, et al. B—H···π interaction: A new type of nonclassical hydrogen bonding[J]. Journal of the American Chemical Society,2016,138(13):4334-4337. doi: 10.1021/jacs.6b01249
    [33]
    KRISHNAMACHARI P, LOU J Z, SANKAR J, et al. Characterization of fourth-generation high-temperature discontinuous fiber molding compounds[J]. International Journal of Polymer Analysis Characterization,2009,14(7):588-599. doi: 10.1080/10236660903225452
    [34]
    LIU Y, MO S, HE M H, et al. Phenylethynyl-terminated oligoimides based on bis(p-aminophenoxy)dimethyl silane: Effect of siloxane structure on processability and thermal stability[J]. High Performance Polymers,2019,31(6):651-661. doi: 10.1177/0954008318780211
    [35]
    TIWARI A, NEMA A K, DAS C K, et al. Thermal analysis of polysiloxanes, aromatic polyimide and their blends[J]. Thermochimica Acta,2004,417(1):133-142. doi: 10.1016/j.tca.2003.10.003
    [36]
    刘仪, 许晓洲, 莫松, 等. 含硅氧烷结构聚酰亚胺树脂的耐热稳定性及高温结构演变[J]. 高等学校化学学报, 2019, 40(1):187-194. doi: 10.7503/cjcu20180342

    LIU Yi, XU Xiaozhou, MO Song, et al. Thermal stability of polyimide resins containing siloxane structure and their high temperature structural evolution[J]. Chemical Journal of Chinese Universites,2019,40(1):187-194(in Chinese). doi: 10.7503/cjcu20180342
    [37]
    LINCOLN J E, HOUT S, FLAHERTY K, et al. High temperature organic/inorganic addition cure polyimide composites, part 1: Matrix thermal properties[J]. Journal of Applied Polymer Science,2008,107(6):3557-3367. doi: 10.1002/app.27463
    [38]
    LINCOLN J E, MORGAN R J, CURLISS D B. Effect of matrix chemical structure on the thermo-oxidative stability of addition cure poly(imide siloxane) composites[J]. Polymer Composites,2008,29(6):585-596. doi: 10.1002/pc.20428
    [39]
    高龙飞, 李松, 肖沅谕, 等. 纤维增强PMR型聚酰亚胺复合材料研究概况[J]. 玻璃钢/复合材料, 2018(9):106-110.

    GAO Longfei, LI Song, XIAO Yuanyu, et al. Research overview of fiber reinforced PMR polyimide matrix composites[J]. Fiber Reinforced Plastics/Composites,2018(9):106-110(in Chinese).
    [40]
    PEI X L, CHEN G F, FANG X Z. Synthesis and properties of poly(imide siloxane) block copolymers with different block lengths[J]. Journal of Applied Polymer Science,2013,129(6):3718-3727. doi: 10.1002/app.38918
    [41]
    GHOSH A, BANERJEE S. Structure-property co-relationship of fluorinated poly(imide-siloxane)s[J]. Polymers for Advanced Technologies,2008,19(11):1486-1494.
    [42]
    XU J L, LI H, ZENG K, et al. Curing kinetics and thermal stability of novel siloxane-containing benzoxazines[J]. Thermochimica Acta,2019,671:119-126. doi: 10.1016/j.tca.2018.11.016
    [43]
    BABANZADEH S, MAHJOUB A R, MEHDIPOUR-ATAEI S. Novel soluble thermally stable silane-containing aromatic polyimides with reduced dielectric constant[J]. Polymer Degradation and Stability,2010,95(12):2492-2498. doi: 10.1016/j.polymdegradstab.2010.08.001
    [44]
    FANG X M, XIE X Q, SIMONE C D, et al. A solid-state 13C NMR study of the cure of 13C-labeled phenylethynyl end-capped polyimides[J]. Macromolecules,2000,33(5):1671-1681. doi: 10.1021/ma991197m
    [45]
    GRASSIE N, MACFARLANE I G. The thermal degradation of polysiloxanes-I poly(dimethylsiloxane)[J]. European Polymer Journal,1978,14(11):875-884. doi: 10.1016/0014-3057(78)90084-8
    [46]
    XU X Z, LIU Y, LAN B W, et al. High thermally stable and melt processable polyimide resins based on phenylethynyl-terminated oligoimides containing siloxane structure[J]. Materials,2020,13(17):3742. doi: 10.3390/ma13173742
    [47]
    LIU Y, FAN L, XU X, et al. Melt fluidity and thermal property of thermosetting siloxane-containing polyimide resins and their organic/inorganic hybrid characteristics[J]. Materials Today Communications,2020,25:101443. doi: 10.1016/j.mtcomm.2020.101443
    [48]
    LIU Y, XU X Z, MO S, et al. Long-term thermo-oxidative degradation modeling of a carbon fiber reinforced polyimide composite: Multistep degradation behaviors and kinetics[J]. Chinese Journal of Polymer Science,2020,38:1202-1213. doi: 10.1007/s10118-020-2425-7
    [49]
    LIU Y, XU X Z, MO S, et al. Kinetic study of the multistep thermo-oxidative degradation of thermosetting siloxane-containing polyimide and unmodified polyimide[J]. Journal of Applied Polymer Science,2020,137:e49021. doi: 10.1002/app.49021
    [50]
    刘仪, 莫松, 张国栋, 等. 苯乙炔基封端含硅氧烷结构聚酰亚胺树脂的热稳定性研究[C]//2017年全国高分子学术论文报告会. 成都: 中国化学会, 2017: 29.

    LIU Y, MO S, ZHANG G D, et al. Research on the thermal stability of the siloxane containing polyimides [C]// Proceedings of the 2017 National Polymer Academic Paper Conference. Chengdu: Chinese Chemical Society, 2017: 29(in Chinese).
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