Bismaleimide (BMI) resins are widely used in microelectronics and aerospace materials due to their excellent thermal properties, dielectric performance, and flame retardancy. However, their brittleness, high curing temperature, and narrow processing window limit their applications. In this study, the benzoxazine resin precursor derived from melamine and furylamine (MBF) was synthesized and used to modify BMI. The results indicate that the reactive secondary amine groups in MBF enhance the curing reactivity of the resin system, while the triazine ring structure contributes to the reduction of the dielectric constant. At 1 MHz, the dielectric constant of poly (BDM-10MBF) is the lowest value of 2.85. Moreover, the modified resin exhibits the highest thermal decomposition temperature (Td5) of 462°C and a maximum char yield (at 800°C) of 52.7%. Furthermore, the resin was compounded with glass fibers to prepare high-strength composites. The flexural modulus of PP(BDM-MBF) is 73.10 GPa, representing a 24% increase compared to PP(BDM). Additionally, its flexural strength reaches 827.0 MPa, which is 104% higher than that of PP(BDM).
WangYYuanLLiangG, et al.Achieving ultrahigh glass transition temperature, halogen-free and phosphorus-free intrinsic flame retardancy for bismaleimide resin through building network with diallyloxydiphenyldisulfide. Polymer2020; 203: 122769.
2.
GeMLiangGGuA. A facile strategy and mechanism to achieve biobased bismaleimide resins with high thermal-resistance and strength through copolymerizing with unique propargyl ether-functionalized allyl compound. React Funct Polym2023; 186: 105570.
3.
IredaleRJWardCHamertonI. Modern advances in bismaleimide resin technology: a 21st century perspective on the chemistry of addition polyimides. Prog Polym Sci2017; 69: 1–21.
4.
ZhangZZhangKXieK, et al.Improvement in toughness and flame retardancy of bismaleimide/diallyl bisphenol A resin with a eugenol allyl ether-grafted polysiloxane. Eur Polym J2022; 180: 111594.
5.
ZhouXQiuSCaiW, et al.Construction of hierarchical MoS2@TiO2 structure for the high performance bimaleimide system with excellent fire safety and mechanical properties. Chem Eng J2019; 369: 451–462.
6.
DerradjiMMehelliOLiuW, et al.Sustainable and ecofriendly chemical design of high performance bio-based thermosets for advanced applications. Front Chem2021; 9: 691117.
7.
ZhaoQLiXTianZ, et al.Controlling degradation and recycling of carbon fiber reinforced bismaleimide resin composites via selective cleavage of imide bonds. Composites Part B2022; 231: 109595.
8.
RenZDHaoSJXingY, et al.Asymmetric bismaleimide-based high-performance resins with improved processability and high Tg over 400 C. High Perform Polym2019; 31: 1132–1139.
9.
HuHXLiCWangCJ, et al.Curing kinetics, thermal and erosive wear characteristics of bismaleimide blends modified by polyaryletherketone. High Perform Polym2022; 35: 126–141.
10.
ZhouXQiuSHeL, et al.Bifunctional linear polyphosphazene decorated by allyl groups: synthesis and application as efficient flame-retardant and toughening agent of bismaleimide. Composites Part B2022; 233: 109653.
11.
JiangXChuFLuoX, et al.Exploring the effects of cardanol-based co-curing agents with different phosphorus structures on the mechanical and flame-retardant properties of bismaleimide resin. Composites Part B2022; 241: 110047.
12.
HanXYuanLGuA, et al.Development and mechanism of ultralow dielectric loss and toughened bismaleimide resins with high heat and moisture resistance based on unique amino-functionalized metal-organic frameworks. Composites Part B2018; 132: 28–34.
13.
ZhouXChuFQiuS. Effects of phenylphosphonate and aliphatic phosphonate structures on the flame retardant performance of bismaleimide. Polym Degrad Stabil2022; 205: 110143.
14.
JiangXChuFZhouX, et al.Construction of bismaleimide resin with enhanced flame retardancy and mechanical properties based on a novel DOPO-derived bismaleimide monomer. J Colloid Interface Sci2022; 614: 629–641.
15.
GeMMiaoJYuanL, et al.Building and origin of bio-based bismaleimide resins with good processability, high thermal, and mechanical properties. J Appl Polym Sci2018; 135: 45947.
16.
ZhouXQiuSLiuJ, et al.Construction of porous g-C3N4@PPZ tubes for high performance BMI resin with enhanced fire safety and toughness. Chem Eng J2020; 401: 126094.
17.
KaracaN. A novel carbazole based bismaleimide monomer: synthesis, characterization, thermal and optical properties. High Perform Polym2023; 35: 581–592.
18.
QuCChangJLiuC, et al.Novel allyl and propenyl monomers for modification of the bismaleimide resins, with excellent dielectric properties and high glass transition temperatures. High Perform Polym2020; 32: 116–126.
19.
YuanZWangLLiuC, et al.Bismaleimide resins modified by a novel vanillin‐derived allyl compounds: synthesis, curing behavior, and thermal properties. Polym Eng Sci2023; 63: 1668–1677.
20.
JiangXChuFLiuW, et al.An individualized core–shell architecture derived from covalent triazine frameworks: toward enhancing the flame retardancy, smoke release suppression, and toughness of bismaleimide resin. ACS Mater Lett2023; 5: 630–637.
21.
LiXHuXLiuX, et al.A novel approach to obtain low-dielectric materials: changing curing mechanism of bismaleimide–triazine resin with ZIF-8. J Mater Sci2021; 56: 15767–15781.
22.
ShaXFeiPShenB, et al.Solvent-free synthesis of alkynyl-based biobased benzoxazine resins with excellent heat resistance. ACS Appl Polym Mater2023; 5: 3015–3022.
23.
LuALinHYuanM, et al.Preparation of biphenyl-containing polybenzoxazines with low dielectric constants and high thermal stability. Polymer2023; 280: 126018.
24.
DingHWangXSongL, et al.Recent advances in flame retardant bio-based benzoxazine resins. J Renew Mater2022; 10: 871–895.
25.
LuYPengYYangY, et al.Low-temperature terpolymerizable benzoxazine monomer bearing norbornene and furan groups: synthesis, characterization, polymerization, and properties of its polymer. Molecules2023; 28: 3944.
26.
ZhangLMaoJLWangS, et al.Synthesis and thermal properties of phenol- and amine-capped main-chain benzoxazine oligomers with multiple methyl substitutions. High Perform Polym2020; 32: 823–834.
27.
BerrouaneADerradjiMKhiariK, et al.Sustainable synthesis of a novel bio-based low temperature curable benzoxazine monomer from quercetin: synthesis, curing reaction and thermal properties. High Perform Polym2023; 36: 3–16.
28.
LyuJJiBWuN, et al.The effect of substituent group in allyl benzoxazine on the thermal, mechanical and dielectric properties of modified bismaleimide. React Funct Polym2023; 191: 105673.
29.
HaoBWangJZhangY, et al.Chrysin-based bio-benzoxazine: a copolymerizable green additive for lowering curing temperatures and improving thermal properties of various thermosetting resins. ACS Appl Polym Mater2022; 4: 1286–1297.
30.
YeJFanZZhangS, et al.Improved curing reactivity, thermal resistance and mechanical properties of furylamine‐based benzoxazine using melamine as an amine source. Polym Adv Technol2023; 34: 1253–1264.
OzawaT. A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn1965; 38: 1881–1886.
33.
YeJLiQZhangS, et al.Melamine modified phthalonitrile resins: synthesis, polymerization and properties. Polymer2022; 256: 125156.
34.
RameshSSivasamyAKimJSynthesis and characterization of maleimide-functionalized polystyrene-SiO2/TiO2 hybrid nanocomposites by sol–gel process. Nanoscale Res Lett2012; 7: 350.
JiangMXuMJiaK, et al.Copolymerization of self-catalyzed phthalonitrile with bismaleimide toward high-temperature-resistant polymers with improved processability. High Perform Polym2016; 28: 895–907.
37.
WangJWLiJXZhangJ, et al.High-performance reversible furan-maleimide resins based on furfuryl glycidyl ether and bismaleimides. Polymers2023; 15: 3470.
38.
WangYKouKWuG, et al.The curing reaction of benzoxazine with bismaleimide/cyanate ester resin and the properties of the terpolymer. Polymer2015; 77: 354–360.
39.
ZhangXChiQTangC, et al.Achieving high-temperature resistance and excellent insulation property of epoxy by introducing triazine ring structure. J Mater Sci Mater Electron2023; 34: 638.
40.
WanJZhaoJGanB, et al.Ultrastiff biobased epoxy resin with high tg and low permittivity: from synthesis to properties. ACS Sustainable Chem Eng2016; 4: 2869–2880.
41.
ZhangYHLiuXZhuM, et al.Dielectric properties of carbon-nanotube/amino-functionalized poly(arylene ether ketone) composites. High Perform Polym2012; 24: 173–179.
