The effect of bismaleimide on thermal,mechanical,and dielectric properties of allyl-functional bisphthalonitrile/bismaleimide system

Abstract

Allyl-functional phthalonitrile (DBPA-Ph) and bismaleimide (BMI) have been considered as advanced composite-matrix resins applied in various fields. In this work, self-promoted polymerization behavior and processability of DBPA-Ph/BMI system were investigated in detail. To further reveal the effect of BMI on the properties of DBPA-Ph/BMI system, the blends and the prepolymers of DBPA-Ph/BMI were prepared in different proportions. Their curing and rheological behaviors were investigated by differential scanning calorimetry and dynamic rheological analysis. The results further confirmed the possible reaction mechanisms and demonstrated that DBPA-Ph/BMI prepolymers exhibited good processability, which included wide processing window (approximately 75°C), low melting viscosity (<0.2 Pa·s), and better reactivity. The copolymers exhibited satisfactory thermal stabilities (T _5% > 421°C, char yield at 600°C >70%). Moreover, the DBPA-Ph/BMI/glass fiber composite laminates were prepared and the effect of the curing temperature and BMI content on mechanical properties and dielectric properties were also investigated. The results show that the composite laminates exhibit favorable mechanical properties and weak frequency dependence of dielectric properties over a wide frequency range. Above all, the research on DBPA-Ph/BMI system could expand its applications in industry, especially in the areas, which require high temperature resistance and excellent mechanical and dielectric properties.

Keywords

Phthalonitrile bismaleimide processability mechanical properties dielectric properties

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References

Liu

Wang

. Preparation and properties of film materials of poly(aryl ether ketone)-based phthalonitrile resins. Polym Eng Sci 2015; 55(10): 2313–2321.

Nair

CPR

Mathew

Ninan

. New polymerization techniques and synthetic methodologies. Adv Polym Sci 2001; 155: 1–99.

Ambika Devi

Reghunadhan Nair

Ninan

. Diallyl bisphenol A-novolac epoxy system cocured with bispheno-A-bismaleimide-cure and thermal properties. J Appl Polym Sci 2007; 106(2): 1192–1200.

Zhu

Yuan

Liang

. Green flame retarding bismaleimide resin with simultaneously good processing characteristics, high toughness and outstanding thermal stability based on a multi-functional organic boron compound. Polym Degrad Stabil 2015; 118: 33–44.

Yuan

Huang

Jiao

. Characterization of modified bismaleimide resin. J. Appl Polym Sci 1996; 62(3): 459–464.

Liu

Chen

. Novel thermosetting resins based on 4-(N-maleimidophenyl) glycidylether: II. Bismaleimides and polybismaleimides. Polymer 2004; 45(6): 1797–1804.

Zhang

. Advance in research on toughening modification of bismaleimide resin. Adhes In China 2004; 2: 012.

Gaina

. New bismaleimide-epoxy resin system. Polym-plast Technol 2009; 48(5): 525–529.

Chandra

Rajabi

. Recent advances in bismaleimides and epoxy-lmide/ bismaleimide formulations and composites. J Macromol Sci Polym Rev 1997; 37(1): 61–96.

10.

Jiang

Jia

. Copolymerization of self-catalyzed phthalonitrile with bismaleimide toward high-temperature-resistant polymers with improved processability. High Perform Polym 2016; 28(8): 895–907.

11.

Huang

Jiang

. Curing behavior and processability of BMI/3-APN system for advanced glass fiber composite laminates. J Appl Polym Sci 2016; 133(27): 43640.

12.

Cheng

Xie

. Synthesis of a bismaleimide/cyanate ester copolymer containing phenolphthalein functional group with excellent dielectric properties and thermally stable. J Polym Res 2014; 21(12): 1–8.

13.

Liang

. A new bismaleimide system for resin transfer molding. Polym Compos 1997; 18(1): 151–155.

14.

Phelan

Sung

CSP

. Fluorescence characteristics of cure products in bis (maleimide)/diallylbisphenol A resin. Macromolecules 1997; 30(22): 6837–6844.

15.

Kumar

KSS

Nair

CPR

Radhakrishnan

. Bis allyl benzoxazine: synthesis, polymerisation and polymer properties. Eur Polym J 2007; 43(6): 2504–2514.

16.

Wang

Zhao

Ran

. Research on curing mechanism and thermal property of bis-allyl benzoxazine and N,N′-(2,2,4-trimethylhexane-1,6-diyl) dimaleimide blend. React Funct Polym 2013; 73(4): 668–673.

17.

Zou

Jia

. Copolymerizing behavior and processability of ally-functional bisphthalonitrile/bismaleimide system. Polym Compos 2015. DOI: 10.1002/pc.23726.16.

18.

Zou

Jia

. Synthesis, polymerization, and properties of the allyl-functional phthalonitrile. J Appl Polym Sci 2014; 131(23).

19.

Pan

Shiau

Lin

. Effect of barbituric acid on the self-polymerization reaction of bismaleimides. J Appl Polym Sci 1992; 45(1): 103–109.

20.

Donnellan

Roylance

. Relationships in a bismaleimide resin system. Part I: Cure mechanisms. Polym Eng Sci 1992; 32(6): 409–414: 41203.

21.

Nair

CPR

Bindu

Ninan

. Recent advances in phenolic resins. Met Mater Process 1997; 9(2): 179–200.

22.

Sastri

Keller

. Phthalonitrile polymers: cure behavior and properties. J Polym Sci Part A: Polym Chem 1999; 37(13): 2105–2111.

23.

Gouri

Nair

CPR

Ramaswamy

. Thermal decomposition characteristics of Alder-ene adduct of diallyl bisphenol A novolac with bismaleimide: effect of stoichiometry, novolac molar mass and bismaleimide structure. Eur Polym J 2002; 38(3): 503–510.

24.

Stenzenberger

Heinen

Hummel

. Thermal degradation of poly (bismaleimides). J Polym Sci: Polym Chem Edit 1976; 14(12): 2911–2925.

25.

Chandran

Krishna

Rai

. Cure kinetics and activation energy studies of modified bismaleimide resins. ISRN Polym Sci 2012; 2012(4); DOI: 10.5402/2012/309861.

26.

King

Chaudhari

Zahir

. A new BMI system for high performance applications. 29th SAMPE Symp 1984; 29: 392.

27.

Stenzenberger

Addition polyimides. Berlin/Heidelberg: Springer, 1994, pp. 165–220

28.

Nair

CPR

. Advances in addition-cure phenolic resins. Prog Polym Sci 2004; 29(5): 401–498.

29.

Liang

. Preparation and properties of mesoporous silica/bismaleimide/diallylbisphenol composites with improved thermal stability, mechanical and dielectric properties. Exp Polym Lett 2011; 5(6): 555–568.

30.

Krishnadevi

Selvaraj

Prasanna

. Thermal, mechanical and antibacterial properties of cyclophosphazene incorporated benzoxazine blended bismaleimide composites. RSC Adv 2015; 5(2): 913–921.

31.

Ursache

Gaina

. High performance bismaleimide resins modified by novel allyl compounds based on polytriazoles. J Polym Res 2012; 19(10): 1–9.

32.

Meng

Zhao

Zhan

. Design of thorn-like micro/nanofibers: fabrication and controlled morphology for engineered composite materials applications. J Mater Chem 2011; 21(41): 16385–16390.

33.

Meng

Ishida

Liu

. Introduction of benzoxazine onto the graphene oxide surface by click chemistry and the properties of graphene oxide reinforced polybenzoxazine nanohybrids. RSC Adv 2014; 4(19): 9471–9475.

34.

Chen

Meng

. Super-high thermal conductivity of polyamide-6/graphene-graphene oxide composites through in situ polymerization. High Perform Polym 2017; 29(5): 585–594.