Synthesis and properties of bismaleimide resin containing dicyclopentadiene or dipentene. VI

Abstract

New aromatic bismaleimides (BMIs), bis(4-maleimidophenoxy-3,5-dimethylphenyl)dicyclopentadiene (DCPDBMI) and bis(4-maleimido-phenoxy-3,5-dimethylphenyl)dipentene (DPBMI), containing a large dicyclopentadiene (DCPD) or dipentene (DP) and aryl ether linkage, were synthesized from diamine bis(4aminophenoxy-3,5-dimethylphenyl)dicyclopentadiene (DCPDA) or bis(4-aminophenoxy-3,5-dimethylphenyl)dipentene(DPA) and maleic anhydride by the usual two-step procedure that included ring-opening addition to give bismaleamic acid, followed by cyclodehydration to bismaleimide. The monomers were characterized by Fourier transform infrared spectroscopy, proton NMR, elemental analyses, and mass spectra. Their thermal polymerization was investigated by DSC. The presence of a large cycloaliphatic moiety in the backbone of the bismaleimide increased the curing temperature and reduced the reactivity of the maleimide bond. Thermal and electrical properties of cured bismaleimide resins were studied using a dielectric analyzer, dynamic mechanical analyzer, and thermal gravimetric analyzer. These data were compared with that of commercial 4,4bismaleimidodiphenylmethane (DDMBMI). The cured DCPDBMI or DPBMI exhibits a lower dielectric constant, dissipation factor and moisture absorption than those of DDMBMI.

Soluble asymmetric bismaleimide with low molten viscosity and its high glass transition temperature polymer

“…The obtained E a , A and n values are listed in Table III. The resulting activation energies for the melt treated EBA-BMI, MBA-BMI, and PBA-BMI are 104, 120, and 153 kJ mol 21 , respectively, which are compared well with the literature values. 37 The high E a implies that the curing of the bismaleimide monomers needs more energy.…”

“…Differential scanning calorimetry (DSC) was measured using a TA Q200 calorimeter under nitrogen atmosphere at a heating rate of 10 8C min 21 . Dynamic mechanical analysis (DMA) was carried out on a TA Q800 analyzer in three-point bending mode at a heating rate of 3 8C min 21 with a frequency of 1 Hz.…”

“…Another effective strategy is the modification of BMI's chemical structure. A number of new chain‐extended BMIs have been designed and synthesized, such as those containing amide, ester, naphthalene, phosphorus, silicon, 1,3,4‐oxadiazole, biphenylene, dicyclopentadiene or dipentene, fluorenyl, parabanic, allyl, s‐triazine, phenylindane, azobenzene, epoxy backbone, and metal complex . Based on the structure–properties relationships, the unsymmetrical chemical structure can hinder the ordered packing or crystallization of the molecules, hence improve the solubility of the monomers.…”

Synthesis and characterization of multifunctional propenyl-endcapped aromatic co-monomers and their use as bismaleimide modifiers

“…[1][2][3] Bismaleimide (BMI) resins, in particular, exhibit characteristics such as excellent thermal oxidation stabilities, dielectric properties, humidity and corrosion resistance. [4] Therefore, BMI-based resins have become one of the most versatile highperformance thermosetting materials with a wide range of applications in both microelectronics and aerospace. Examples include multilayer printed circuit boards, advanced composites for aerospace industries as well as structural adhesives.…”

Synthesis and properties of chain‐extended bismaleimide resins containing phthalide cardo structure

“…In recent years, great efforts have been made to modify chemically the structure of BMI monomers with the aim of improving their solubility, lowering their melting points and enhancing the fracture toughness of the corresponding cured resins. As a result, a number of new chain‐extended BMI monomers have emerged, including those containing naphthalene,6–8 phosphorus,9–12 silicon,13, 15 1,3,4‐oxadiazole,14, 15 biphenylene,16 dicyclopentadiene or dipentene17 and fluorenyl cardo groups 18. Nevertheless, aside from Varma et al and Camelia and Constantin, who have reported on 3,3‐bis( p ‐aminophenyl)phthalide‐based BMI and ester BMI monomer with phthalein moieties, respectively,19, 20 few researchers have paid special attention to the investigation of BMIs containing the phthalide structure.…”