Preparation of polyimides containing carborane moiety and the thermal resistance mechanism

HAO Yifan; DONG Jie; ZHAO Xin; ZHANG Qinghua

doi:10.13801/j.cnki.fhclxb.20220124.001

Volume 40 Issue 1

Jan. 2023

Turn off MathJax

Article Contents

Article Navigation > Acta Materiae Compositae Sinica > 2023 > 40(1): 131-140

HAO Yifan, DONG Jie, ZHAO Xin, et al. Preparation of polyimides containing carborane moiety and the thermal resistance mechanism[J]. Acta Materiae Compositae Sinica, 2023, 40(1): 131-140. doi: 10.13801/j.cnki.fhclxb.20220124.001

Citation:

HAO Yifan, DONG Jie, ZHAO Xin, et al. Preparation of polyimides containing carborane moiety and the thermal resistance mechanism[J]. Acta Materiae Compositae Sinica, 2023, 40(1): 131-140. doi: 10.13801/j.cnki.fhclxb.20220124.001

Citation:

PDF( 4804 KB)

Preparation of polyimides containing carborane moiety and the thermal resistance mechanism

doi: 10.13801/j.cnki.fhclxb.20220124.001

State Key Laboratory of Fiber Material Modification, Donghua University, Shanghai 201620, China

Funds: National Natural Science Foundation of China (51903038; 52173196; 21975040)

Received Date: 2021-11-10
Accepted Date: 2022-01-09
Rev Recd Date: 2021-12-20

Available Online: 2022-01-26

Publish Date: 2023-01-15

Abstract

Abstract

A series of polyimide materials were successfully prepared by embedding o-carborane cage structure into polyimide main chains. First, the diamine monomer (DNCB) containing o-carborane unit was designed and synthesized, and then copolymerized with 4,4'-diaminodiphenyl ether (ODA) and 3,3',4,4'-benzophenone tetracarboxylic anhydride (BTDA) to synthesize the polyamic acid (PAA) precursor solution. PAA films were prepared by solution casting method, and then polyimide films containing different contents of carborane unit were obtained after high-temperature thermal imidization. Thermogravimetric analysis (TGA) shows that the addition of DNCB significantly improves the thermal stability and thermal oxidation stability of polyimide materials. When the molar content of DNCB in all diamines reaches 40%, the temperature corresponding to 5wt% mass loss (T_5%) increases by nearly 13℃, T_10% increases by nearly 43℃ and the mass residual rate was as high as 82.6wt%. Under the air atmosphere, T_5% increases by nearly 36℃, T_10% increases by nearly 64℃, and the mass residual rate reaches as high as 83.1wt%. This is due to the oxidation of carborane cage and the formation of multi-layer passivation protective layer on the surface of the film, which prevents the degradation of internal polymer materials in contact with oxygen.
- polyimide,
- carborane,
- organic-inorganic hybrid,
- thermal oxidation stability,
- passivation layer,
- thermal resistance mechanism
Long Abstrsct
Innovation Points

FullText(HTML)

References(22)

References

[1]	QU X M, JI M, FAN L, et al. Thermoset polyimide matrix resins with improved toughness and high T_g for high temperature carbon fiber composites[J]. High Performance Polymers,2011,23(4):281-289. doi: 10.1177/0954008311403839
[2]	KARGER-KOCSIS J, MAHMOOD H, PEGO-RETTI A. Recent advances in fiber/matrix interphase engineering for polymer composites[J]. Progress in Materials Science,2015,73:1-43. doi: 10.1016/j.pmatsci.2015.02.003
[3]	LAU K S Y. High-performance polyimides and high tempera-ture resistant polymers[M]. California: Chemco Systems, Inc., 2014: 297-424.
[4]	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. LIU Yi, MO Song, PAN Lingying, et al. High temperature resistant organic-inorganic hybrid polyimide resin and its composite materials[J]. Aerospace Materials & Technology,2018,48(3):1-5(in Chinese).
[5]	王天琦, 肖国勇, 鲁云华, 等. 镧系金属有机骨架/聚酰亚胺复合材料的制备及其性能[J]. 复合材料学报, 2018, 35(11):2927-2934. WANG Tianqi, XIAO Guoyong, LU Yunhua, et al. Preparation and properties of lanthanide metal-organic frameworks/polyimide composites[J]. Acta Materiae Compositae Sinica,2018,35(11):2927-2934(in Chinese).
[6]	LIU Z Y, LIU Y, QIU W L, et al. Molecularly engineered 6FDA-based polyimide membranes for sour natural gas separation[J]. Angewandte Chemie International Edition,2020,59(35):14877-14883. doi: 10.1002/anie.202003910
[7]	WU A X, DRAYTON J A, RODRIGUEZ K M, et al. Influence of aliphatic and aromatic fluorine groups on gas permeability and morphology of fluorinated polyimide films[J]. Macromolecules,2020,53(13):5085-5095. doi: 10.1021/acs.macromol.0c01024
[8]	PARK Y S, JEE M H, BAIK D H. Preparation and characterization of electrospun multi-layered polyimide nanoweb with enhanced mechanical properties[J]. Fibers and Polymers, 2021, 23(2): 360-365.
[9]	QIAN G T, CHEN H Q, SONG G L, et al. Superheat-resistant polyimides with ultra-low coefficients of thermal expansion[J]. Polymer,2020,196:188482.
[10]	LIAN R H, LEI X F, XUE S Y, et al. Janus polyimide films with outstanding AO resistance, good optical transparency and high mechanical strength[J]. Applied Surface Science,2021,535:147654. doi: 10.1016/j.apsusc.2020.147654
[11]	LIU Y W, TANG A, TAN J H, et al. Structure and gas barrier properties of polyimide containing a rigid planar fluorene moiety and an amide group: Insights from molecular simulations[J]. ACS Omega,2021,6(6):4273-4281. doi: 10.1021/acsomega.0c05278
[12]	LIU T Q, ZHENG F, MA X R, et al. High heat-resistant polyimide films containing quinoxaline moiety for flexible substrate applications[J]. Polymer,2020,209:122963. doi: 10.1016/j.polymer.2020.122963
[13]	MEKURIA T D, WANG L, ZHANG C H, et al. Synthesis and characterization of high strength polyimide/silicon nitride nanocomposites with enhanced thermal and hydrophobic properties[J]. Chinese Journal of Chemical Engineering,2021,32:446-453. doi: 10.1016/j.cjche.2020.09.066
[14]	OU X H, CHEN S S, LU X M, et al. Enhancement of thermal conductivity and dimensional stability of polyimide/boron nitride films through mechanochemistry[J]. Composites Communications,2021,23:100549. doi: 10.1016/j.coco.2020.100549
[15]	OTHMAN M B H, RAMLI R, ARIFF Z M, et al. Thermal properties of polyimide system containing silicone segments[J]. Journal of Thermal Analysis and Calorimetry,2012,109(3):1515-1523. doi: 10.1007/s10973-011-1893-y
[16]	LI X M, WU J Y, TANG C Y, et al. High temperature resistant polyimide/boron carbide composites for neutron radiation shielding[J]. Composites Part B: Engineering,2019,159:355-361. doi: 10.1016/j.compositesb.2018.10.003
[17]	VINOGRADOVA S V, VALETSKII P M, KABACHII Y A. Polymers with arylenedicarbadodecaborane fragments in the chain[J]. Russian Chemical Reviews,1995,64(4):365-388. doi: 10.1070/RC1995v064n04ABEH000155
[18]	ENDO Y, SONGKRAM C, YAMASAKI R, et al. Molecular construction based on icosahedral carboranes and aromatic N,N'-dimethylurea groups. Aromatic layered molecules and a transition metal complex[J]. Journal of Organometallic Chemistry,2002,657(1):48-58.
[19]	HUANG X, ZHANG Q H, MENG Z, et al. Greatly enhanced thermo-oxidative stability of polybenzoxazine thermoset by incorporation of m-carborane[J]. Journal of Polymer Science Part A: Polymer Chemistry,2015,53(8):973-980. doi: 10.1002/pola.27525
[20]	LI N, ZENG F L, QU D Z, et al. Synthesis and characterization of carborane-containing polyester with excellent thermal and ultrahigh char yield[J]. Journal of Applied Polymer Science,2016,133(46):44202.
[21]	CUI M L, ZHANG L L, LOU P P, et al. Study on thermal degradation mechanism of heat-resistant epoxy resin modified with carboranes[J]. Polymer Degradation and Stability,2020,176:10913.
[22]	GOYAL S, FORRESTER M J, COVERDELL D, et al. High-temperature-performance cyanate ester composites with carboranes[J]. Macromolecules,2021,54(19):9155-9164. doi: 10.1021/acs.macromol.1c01410