Abstract
A series of high performance fluorinated bismaleimide-triazine (BT) resins were prepared from 2, 2′-Bis(4-cyanatophenyl) propane (CY-1), 2′-Bis[4-(4-maleimidephenoxy) phenyl] hexafluoropropane (6FBMP) and diallyl hexafluorobisphenol A (6FDABPA). The effect of the fluorinated groups on the curing behavior, thermal stability, mechanical and dielectric properties was studied. Dielectric constant of the fluorinated BT resin was 2.89–2.94 and the dielectric loss could reach 0.002–0.004 at 1 MHz, which were dramatically improved compared with the reported cyanate ester resins. The fluorinated BT resins also exhibited excellent thermal stability, with a high glass transition temperature above 220 °C and 5% weight loss thermal decomposition temperature (Td5) exceeding 400 °C. Meanwhile, the impact strength of the fluorinated BT resins could reach 20 kJ/m2 and the flexural strength was 120 MPa. Small dipole, low polarizability, high bond energy of the carbon-fluorine (C-F) bond and symmetrical hexafluoroisopropyl group were the reason for the enhanced properties. This work suggested that the fluorinated BT resins had great potential to be used as the matrix of the advanced structural and functional composites.
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References
Zeng X, Yu S, Sun R (2013) Thermal behavior and dielectric property analysis of boron nitride-filled bismaleimide-triazine resin composites. J Appl Polym Sci 128(3):1353–1359
Fan J, Hu X, Yue CY (2003) Dielectric properties of self-catalytic interpenetrating polymer network based on modified bismaleimide and cyanate ester resins. J Polym Sci B Polym Phys 41(11):1123–1134
Gu A (2006) High performance bismaleimide/cyanate ester hybrid polymer networks with excellent dielectric properties. Compos Sci Technol 66(11–12):1749–1755
Hu X, Fan J, Yue CY (2001) Rheological study of crosslinking and gelation in bismaleimide/cyanate ester interpenetrating polymer network. J Appl Polym Sci 80(13):2437–2445
Gouri C, Reghunadhan Nair CP, Ramaswamy R (2001) Reactive Alder-ene blend of diallyl bisphenol A novolac and bisphenol A bismaleimide: synthesis, cure and adhesion studies. Polym Int 50(4):403–413
Hu X, Meng J (2005) Effect of organoclay on the curing reactions in bismaleimide/diallyl bisphenol a resin. J Polym Sci Part A: Polym Chem 43(5):994–1006
Koh HCY, Dai J, Tan E (2006) Curing behavior and thermal mechanical properties of cyanate ester blends. J Appl Polym Sci 102(5):4284–4290
Koh HCY, Dai J, Tan E, Liang W (2006) Catalytic effect of 2,2′-diallyl bisphenol A on thermal curing of cyanate esters. J Appl Polym Sci 101(3):1775–1786
Nagai A, Takahashi A, Suzuki M, Mukoh A (1992) Thermal behavior and cured products of fluorine-containing bismaleimides. J Appl Polym Sci 44(1):159–164
Shu WJ, Ho JC (2014) Studies of fluorine-containing bismaleimide resins. Part I: synthesis and characteristics of model compounds. Polym Sci Ser B 56(4):530–537
R-S TSAIW-JSA (2014) Studies on fluorine-containing bismaleimide resins part II: preparation and characteristics of reactive blends of fluorine-containing bismaleimide and epoxy. J Polym Mater 30(1):49–62
Wang Z-Y, Ho J-C, Shu W-J (2012) Studies of fluorine-containing bismaleimide resins part I: synthesis and characteristics of model compounds. J Appl Polym Sci 123(5):2977–2984
Hwang H-J, Li C-H, Wang C-S (2005) Dielectric behavior and properties of a cyanate ester containing dicyclopentadiene. I. J Appl Polym Sci 96(6):2079–2089
Hwang H-J, Lin C-Y, Wang C-S (2008) Flame retardancy and dielectric properties of dicyclopentadiene-based benzoxazine cured with a phosphorus-containing phenolic resin. J Appl Polym Sci 110(4):2413–2423
Reghunadhan Nair CP, Francis T (1999) Blends of bisphenol A-based cyanate ester and bismaleimide: cure and thermal characteristics. J Appl Polym Sci 74(14):3365–3375
Reghunadhan Nair CP, Francis T, Vijayan TM, Krishnan K (1999) Sequential interpenetrating polymer networks from bisphenol A based cyanate ester and bimaleimide: properties of the neat resin and composites. J Appl Polym Sci 74(11):2737–2746
Hwang H-J, Shieh J-Y, Li C-H, Wang C-S (2007) Dielectric and thermal properties of polymer network based on bismaleimide resin and cyanate ester containing dicyclopentadiene or dipentene. III. J Appl Polym Sci 103(3):1942–1951
Apeldorn T, Keilholz C, Wolff-Fabris F, Altstädt V (2013) Dielectric properties of highly filled thermoplastics for printed circuit boards. J Appl Polym Sci 128(6):3758–3770
Lin CH, Hsiao CN, Li CH, Wang CS (2004) Low dielectric thermoset. IV. Synthesis and properties of a dipentene-containing cyanate ester and its copolymerization with bisphenol A dicyanate ester. J Polym Sci A Polym Chem 42(16):3986–3995
Zhang Z, Yu R, Wang F, Wang J, Jiao Y (2011) Synthesis and properties of novel dicyanate with low dielectric and water absorption performance. J Appl Polym Sci 120(6):3716–3723
Guenthner AJ, Yandek GR, Wright ME, Petteys BJ, Quintana R, Connor D, Gilardi RD, Marchant D (2006) A new silicon-containing Bis(cyanate) Ester resin with improved thermal oxidation and moisture resistance. Macromolecules 39(18):6046–6053
Hu J-t, Gu A, Liang G, Zhuo D, Yuan L (2012) Synthesis of mesoporous silica and its modification of bismaleimide/cyanate ester resin with improved thermal and dielectric properties. Polym Adv Technol 23(3):454–462
Hu J-t, Gu A, Liang G, Zhuo D, Yuan L (2012) Preparation and properties of maleimide-functionalized hyperbranched polysiloxane and its hybrids based on cyanate ester resin. J Appl Polym Sci 126(1):205–215
Huang P, Gu A, Liang G, Yuan L (2011) Curing behavior and dielectric properties of hyperbranched poly(phenylene oxide)/cyanate ester resins. J Appl Polym Sci 121(4):2113–2122
Maier G (2001) Low dielectric constant polymers for microelectronics. Prog Polym Sci 26(1):3–65
Guo Y, Han Y, Liu F, Zhou H, Chen F, Zhao T (2015) Fluorinated bismaleimide resin with good processability, high toughness, and outstanding dielectric properties. J Appl Polym Sci 132(46):42791
Gu A, Liang G (2004) Preparation and properties of a novel high-performance resin system with low injection temperature for resin transfer moulding. Polym Int 53(9):1388–1393
Ren Z, Cheng Y, Li Y, Xiao F Preparation and characterization of soluble bismaleimide-triazine resins based on asymmetric bismaleimide. J Appl Polym Sci 134(9):44519
Fan J, Hu X, Yue CY (2001) Interpenetrating polymer networks based on modified cyanate ester resin. Plast Rubber Compos 30(10):448–454
Fan J, Hu X, Yue CY (2003) Thermal degradation study of interpenetrating polymer network based on modified bismaleimide resin and cyanate ester. Polym Int 52(1):15–22
Tao L, Yang H, Liu J, Fan L, Yang S (2009) Synthesis and characterization of highly optical transparent and low dielectric constant fluorinated polyimides. Polymer 50(25):6009–6018
Zhou C, Gu A, Liang G, Xia Y (2015) Tough silica-hybridized epoxy resin/anhydride system with good corona resistance and thermal stability for permanent magnet synchronous wind-driven generators through vacuum pressure impregnation. Ind Eng Chem Res 54(28):7102–7112
Acknowledgements
The authors gratefully acknowledge the financial support of the National Natural Science Foundation of China (No.51403218 & No.51473171 & No.21604090). The authors gratefully thanks the Young Elite Scientist Sponsorship Program by CAST (YESS) and the Youth Innovation Promotion Association of CAS (No. 2017047).
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Guo, Y., Chen, F., Han, Y. et al. High performance fluorinated Bismaleimide-Triazine resin with excellent dielectric properties. J Polym Res 25, 27 (2018). https://doi.org/10.1007/s10965-017-1407-0
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DOI: https://doi.org/10.1007/s10965-017-1407-0