Synthesis and Property of Bismaleimide Resins Containing Fluorene Cardo and Cyano Groups

doi:10.11901/1005.3093.2018.327

Chinese Journal of Materials Research

2018, Vol. 32

Issue (11): 820-826 DOI: 10.11901/1005.3093.2018.327

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Synthesis and Property of Bismaleimide Resins Containing Fluorene Cardo and Cyano Groups

Siyang LIU¹, Ping CHEN¹(

), Xuhai XIONG², Qi YU²

1 State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China
2 Liaoning Key Laboratory of Advanced Polymer Matrix Composites, Shenyang Aerospace University, Shenyang 110136, China

Cite this article:

Siyang LIU, Ping CHEN, Xuhai XIONG, Qi YU. Synthesis and Property of Bismaleimide Resins Containing Fluorene Cardo and Cyano Groups. Chinese Journal of Materials Research, 2018, 32(11): 820-826.

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Abstract

One novel oligomeric BMI monomer of n ≈1 containing fluorene cardo and cyano groups (PFCBMI) was synthesized with 9,9′-bis[4-(4-maleimidophenoxy)phenyl] fluorine and dichlorobenzonitrile as raw materials. The chemical structure as well as the curing behavior and the thermal stability of the BMIs were characterized by means of 1H NMR spectroscopy and Fourier transform infrared spectroscopy (FTIR) as well as dynamic differential scanning calorimeter (DSC) and thermogravimetric analysis (TGA). In addition, the copolymerizations of PFCBMI/BDM resins were investigated. Results show that the characteristic parameters of DSC curves for PFCBMI/BDM resin system increased with the increase of PFCBMI; The increase of PFCBMI leads to the decrease of the crosslink density and thus the decrease of the characteristic parameters for PFCBMI/BDM resins. Furthermore, the PFCBMI/BDM composites present excellent heat resistance with the storage modulus about 10 GPa and the glass transition temperature above 470°C.

Key words: organic polymer materials fluorene cardo group cyano group bismaleimide curing behavior heat resistance

Received: 16 May 2018

ZTFLH:

TQ332.4

Fund: Supported by National Defense Fundamental Research Key Program (No. A35201XXXXX), National Natural Science Foundation of China (Nos. 51303107 & 51703003), Fundamental Research Funds for the Central Universities (No. DUT18GF107), Natural Science Foundation of Liaoning Province (No. 201602149)

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	Siyang LIU
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https://www.cjmr.org/EN/10.11901/1005.3093.2018.327 OR https://www.cjmr.org/EN/Y2018/V32/I11/820

Fig.1 Chemical structure of BDM

Fig.2 Synthetic route to BMI containing fluorene cardo and cyano groups

Fig.3 FTIR spectra of PFCBMI

Fig.4 1H-NMR spectra of PFCBMI

Table 1 The solubility of PFCBMI

Fig.5 DSC curves of PFCBMI

Fig.6 TG curves of PFCBMI

Fig.7 Possible curing reactions between BDM and PFCBMI

Fig.8 DSC curves of PFCBMI /BMDM resin system

Table 2 Characterstic data of DSC curves for PFCBMI/BDM resin system

Fig.9 TGA and DTG curves of PFCBMI/BDM system

Table 3 Characterstic data of thermal decomposition for PFCBMI/BDM resin system

Fig.10 DMA thermogram of composites based on PFCBMI/BDM

Table 4 Characterstic data of DMA for composites based on PFCBMI/BDM

[1]	Chen P, Liao M Y.Science of Synthetic Polymer Materials [M]. 3rd ed. Beijing: Chemical Industry Press, 2011(陈平, 廖明义. 高分子合成材料学 [M]. 3版. 北京: 化学工业出版社, 2017)
[2]	Iredale R J, Ward C, Hamerton I.Modern advances in bismaleimide resin technology: A 21st century perspective on the chemistry of addition polyimides[J]. Prog. Polym. Sci., 2017, 69: 1
[3]	Wu W, Wang D, Ye C.Preparation and characterization of bismaleimide-diamine prepolymers and their thermal-curing behavior[J]. J. Appl. Polym. Sci., 1998, 70: 2471
[4]	Liu X Y, Yu Y F, Li S J.Study on cure reaction of the blends of bismaleimide and dicyanate ester[J]. Polymer, 2006, 47: 3767
[5]	Xiong X H, Chen P, Zhang J X, et al.Preparation and properties of high performance phthalide-containing bismaleimide modified epoxy matrices[J]. J. Appl. Polym. Sci., 2011, 121: 3122
[6]	Sultan J N, Mcgarry F J.Effect of rubber particle size on deformation mechanisms in glassy epoxy[J]. Polym. Eng. Sci., 1973, 13: 29
[7]	Qin H H, Mather P T, Baek J B, et al.Modification of bisphenol-A based bismaleimide resin (BPA-BMI) with an allyl-terminated hyperbranched polyimide (AT-PAEKI)[J]. Polymer, 2006, 47: 2813
[8]	Xiong X H, Chen P, Yu Q, et al.Synthesis and properties of chain-extended bismaleimide resins containing phthalide cardo structure[J]. Polym. Int., 2010, 59: 1665
[9]	Xia L L, Zhai X J, Xiong X H, et al.Synthesis and properties of 1,3,4-oxadiazole-containing bismaleimides with asymmetric structure and the copolymerized systems thereof with 4,4’-bismaleimidodiphenylmethane[J]. RSC Adv., 2014, 4: 4646
[10]	Varma I K, Tiwari R.Thermal characterization of bismaleimide blends[J]. J. Therm. Anal., 1987, 32: 1023
[11]	Yang C P, Chiang H C.Organosoluble and light-colored fluorinated polyimides based on 9,9-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]fluorene and aromatic dianhydrides[J]. Colloid Polym. Sci., 2004, 282: 1347
[12]	Wang J, Wu M Q, Liu W B.Synthesis, curing behavior and thermal properties of fluorene containing benzoxazines[J]. Eur. Polym. J., 2010, 46: 1024-1031
[13]	Stille J K, Harris R M, Padaki S M.Polyquinolines containing fluorene and anthrone cardo units: synthesis and properties[J]. Macromolecules, 1981, 14: 486
[14]	Suresh S, Gulotty R J Jr, Bales S E, et al. A novel polycarbonate for high temperature electro-optics via azo bisphenol amines accessed by Ullmann coupling[J]. Polymer, 2003, 44: 5111
[15]	Hu Z Q, Li S J, Zhang C H.Synthesis and characterization of novel chain-extended bismaleimides containing fluorenyl cardo structure[J]. J. Appl. Polym. Sci., 2008, 107: 1288
[16]	Zhang L Y, Chen P, Gao M B, et al.Synthesis, characterization, and curing kinetics of novel bismaleimide monomers containing fluorene cardo group and aryl ether linkage[J]. Des. Monomers Polym., 2014, 17: 637
[17]	Chen P, Xiong X H, Xia L L, et al.Synthesis and properties of chain-extended bismaleimides with aromatic hetero-cycle structure[J]. Acta Polym. Sin., 2017, (3): 399(陈平, 熊需海, 夏连连等. 链延长型芳杂环双马来酰亚胺树脂的合成及性能[J]. 高分子学报, 2017, (3): 399)
[18]	Chen P, Xiong X H.Aromatic Heterocyclic Bismaleimide Resin [M]. Beijing: Chemical Industry Press, 2016(陈平, 熊需海. 含芳杂环结构双马来酰亚胺树脂 [M]. 北京: 化学工业出版社, 2016)
[19]	Liou G S, Chang C W, Yen H J, et al.Pentaaryldiamine-containing bismaleimide compound and producing method thereof[P]. US Pat, 20100168442, 2010
[20]	Han Y, Wu D M, Zeng K, et al.Synthesis and properties of N-substituted phenyl maleimide with cyano-group[J]. Polym. Mater. Sci. Eng., 2007, 23(3): 96(韩勇, 武迪蒙, 曾科等. 含氰基的N-取代苯基马来酰亚胺的合成及性能[J]. 高分子材料科学与工程, 2007, 23(3): 96)
[21]	Chen P, Liu S Y, Xiong X H, et al.Bismaleimide resin with cyano groups and fluorenyl and method for preparing bismaleimide resin [P]. Chin Pat, 201710153814.2, 2017(陈平, 刘思扬, 熊需海等. 含氰基和芴基双马来酰亚胺树脂及其制备方法 [P]. 中国专利, 201710153814.2, 2017)

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