Thermosetting bismaleimide resins generating covalent and multiple hydrogen bonds

Abstract

Prepolymerizations of 4,4 0 -bismaleimidodiphenylmethane (BMI), diallyl isocyanurate (DAIC), and melamine (ML) at 160-1708C and subsequent compression molding at 200-2808C yielded cured BMI/DAIC/ML resins with feed molar ratios of 4/1/1, 3/1/1, and 2/1/1 (BMI-DAIC-ML411, 311, and 211). Similarly, cured BMI/DAIC 1/1 and BMI/ML 3/1 resins (BMI-DAIC11 and BMI-ML31) were prepared. The FT-IR analysis revealed that the maleimide and allyl groups were almost consumed for all the cured resins, and the hydrogen bonding interaction became stronger with decreasing BMI contents for BMI-DAIC-MLs. Based on the cured structures elucidated from the FT-IR result, the numbers of multiple hydrogen bonds and cross-linking covalent bonds (N MHB and N CB ), and total cross-linking bond energy (E TB ) were evaluated to be 0, 7.92, and 618 for BMI-DAIC-ML411, 0.71, 7.81, and 627 for BMI-DAIC-ML311, and 0.95 mol kg 21, 7.61 mol kg 21, and 617 kcal kg 21 for BMI-DAIC-ML211, respectively. A higher order of glass transition and 5% weight loss temperatures for BMI-DAIC-MLs was 411 > 311 > 211 in accordance with a higher order of N CB . BMI-DAIC-MLs displayed a weak tan d peak at 70-1508C due to dissociation of the hydrogen bonds. The flexural strength and modulus of BMI-DAIC-ML311 were higher than those of BMI-DAIC-ML411 in accordance with the difference of E TB . V C 2015 Wiley Periodicals, Inc. J. Appl. Polym.Sci. 2016, 133, 43121.

Self-healing high-performance thermosets utilizing furan/maleimide Diels–Alder, epoxy/amine nucleophilic ring-opening, and maleimide/amine Michael reactions

“…In this study, a polyaddition oligomer of furfurylamine (FA) and DGEBA at a molar ratio of 1/1 (denoted as FADGEBA) was cured with BMI and melamine (ML) by the DA and Michael addition reactions of maleimide and amino groups (Scheme 1). We previously synthesized a cured product of BMI and ML at a molar ratio of 3/1 by the Michael addition reaction that exhibited excellent thermal and mechanical properties [20]. Therefore, it is expected that the combination of the DA reaction of FADGEBA/BMI and the Michael addition reaction of BMI/ML would lead to the development of thermosetting bismaleimide resins that exhibit improved thermal, mechanical, and healing properties compared to the previously reported cured products of BFSI/BMI/ S4P and FABMI/BMI/XDA (Scheme 2).…”

Nitrogen-Rich Perylene Nanosheet Enhanced Bismaleimide Resin

“…In order to study the changes of chemical structure during the curing process, FT-IR technique was adopted to investigate the possible curing reactions of pure BMI and 0.25 Dianiline +0.1 P-DCD/BMI resin, and the FTIR spectrum is shown in Figure 3a. As shown in Figure 3a, the absorption peaks of located at 2922 cm , and the characteristic absorption peak at 688cm -1 is=C-H [28]. With the proceeding of curing reaction, the characteristic peaks of the N-H at 3749 and 3628 cm -1 , as well as C≡N characteristic peaks at 2000cm -1 emerge.…”

Vinyl-terminated butadiene acrylonitrile improves the toughness, processing window, and thermal stability of bismaleimide resin

“…The remarkably high performance of thermosetting structural resins and resin-based composites has been documented. 1,2 An outstanding and popular thermosetting resin is bismaleimide (BMI), which exhibits unique features such as high glass transition temperature (T g ), corrosion resistance, nonflammability, stable electrical properties over a wide temperature range, and excellent mechanical performance. [3][4][5] In particular, BMI resins retain their physical properties at elevated temperatures and wet conditions, moreover, they exhibit epoxy-like processing and a high service temperature.…”