Synthesis and properties of a benzoxazine monomer containing maleimide and biphenyl groups

Abstract

Benzoxazine resin exhibits excellent properties and is widely used in many fields. Herein, the synthesis of a novel compound, the bis(2,4-dihydro-2 H-3-(4- N-maleimido)phenyl-1,3-benzoxazinyl)biphenyl (BMIPBB), has been reported, which was synthesized by reacting N-(4-aminophenyl)maleimide (APMI), formaldehyde, and 4,4’-dihydroxybiphenyl. 1,3,5-three(4-(maleimido)phenyl)-1,3,5-triazine (TMIPT) was formed as an intermediate during the reaction. The proton nuclear magnetic resonance (1H-NMR) and Fourier transform-infrared (FTIR) spectroscopy experiments were conducted to determine the structure of BMIPBB. BMIPBB was obtained as a reddish-brown solid in 40.1% yield. The thermal properties of BMIPBB were investigated using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) techniques. Analysis of the DSC curves revealed that the broad peak representing the release of curing reaction heat appeared in the temperature range of 140–330°C. The peak temperature was 242.59°C and the heat of the reaction was 393.82 J/g, indicating that the rate of the curing reaction was low and the heat of the reaction was high. Analysis of the TGA results revealed that the weight loss rate was 5% at 110°C. The monomer exhibited a significant weight loss in the range of 320–500°C. The compound lost 50% of its weight at a temperature of 427°C.

Phthalide cardo chain extended imine skeletal linked maleimido end capped nanotitania reinforced novel polybenzoxazine (nTiO2/PBZ) hybrid nanocomposites

“…Maleic anhydride, hydrazine hydrate (80%) and 4-hydroxy benzaldeyde were purchased from Loba Chemie, India. N-(4-aminophenyl) maleimide (NPMI) was synthesized according to the procedure 35 and also the nanotitania particles were prepared using the reported method. 43…”

“…The production of hydroxyl terminal phenolphthalein core aromatic diimine was carried out by the condensation of 3, 3-bis-[4-(4-aminophenoxy)-phenyl]-3H-isobenzofuran-1-one and p -hydroxy benzaldehyde. 35,36 Solution of p -hydroxy benzaldehyde 0.22 mol, 2.88 g) prepared with 40 mL of methanol, was added to the solution of 4, 4'-(4-(pyren-1-yl) pyridine-2, 6-diyl) dianiline (0.011 mol, 5.5 g) in 15 mL methanol (Scheme 2). The made up mixture was continuously stirred at the reflux temperature for 4 h. After the reaction was over checked by TLC, ice water-salt mixture was added on the obtained brown colored solution and the brown product precipitated.…”

Multifunctional Biobased Benzoxazines: Synthesis, Copolymerization, and Thermal Stability Studies

“…At present, bisphenol A is the most studied benzoxazine. Researchers have also optimized the performance of benzoxazines by designing and preparing different benzoxazine precursors. , Polymers containing nitrile-based cross-linking sites have excellent thermal and mechanical properties. Benzoxazines containing alkynyl groups have very low heat release capacity and excellent carbon yield, whereas benzoxazines containing olefin functional groups can still maintain a high T g at 350 °C. − …”