N-(4-Anilinophenyl)maleimide

• CAS: 32099-65-3
• Catalog Number: ACM32099653
• Category: Main Products
• Molecular Weight: 264.28
• Molecular Formula: C₁₆H₁₂N₂O₂
• Synonyms: N-(4-ANILINOPHENYL)MALEIMIDE;Nsc39744;1H-Pyrrole-2,5-dione, 1-[4-(phenylaMino)phenyl]-;Antioxidant MC;MC (antioxidant);N-(p-Anilinophenyl)maleimide;N-[p-(Phenylamino)phenyl]maleimide
• IUPAC Name: 1-(4-anilinophenyl)pyrrole-2,5-dione
• SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)N3C(=O)C=CC3=O
• InChI Key: KPNYFXUDBVQRNK-UHFFFAOYSA-N
• Boiling Point: 466ºC at 760mmHg
• Melting Point: 161-163°C
• Flash Point: 235.7ºC
• Density: 1.346g/cm³
• Exact Mass: 264.09000

Case Study

N-(4-Anilinophenyl)maleimide as a Multifunctional Graftable Antioxidant for Enhanced Polyethylene Performance

Zhang, Chengcheng, et al. IEEE Transactions on Dielectrics and Electrical Insulation 28.2 (2021): 541-549.

Polyethylene (PE) is widely used as an insulating material in high-voltage DC applications, but space-charge accumulation and antioxidant migration can degrade dielectric performance and long-term thermal stability. Herein, N-(4-Anilinophenyl)maleimide (MC) was selected as a reactive, multifunctional hindered-amine antioxidant that can be covalently grafted onto PE. MC was chosen because it combines four useful attributes in a single molecule: (1) a hindered-amine moiety that provides intrinsic antioxidative action; (2) a maleimide group that enables radical grafting to PE without facile homopolymerization; (3) polar functionalities that introduce immobile deep-trap states in the polymer matrix; and (4) a high boiling point that minimizes volatilization and air-bubble defects during melt processing.
Preparation Method: PE grafted with MC (denoted PE-g-MC) was prepared by melt radical grafting using dicumyl peroxide (DCP) as initiator. PE pellets were melted at 110 °C, MC was added and blended, then 0.2 phr DCP was incorporated and mixed briefly. The mixture was hot-compression moulded and then subjected to a further thermal step at 175 °C to complete grafting.
Performance of MC-grafted PE: Grafted MC showed significantly higher retention after acetone extraction compared to conventional antioxidants. The material exhibitd enhanced dielectric properties, including effective suppression of space charge accumulation, reduced DC conductivity, and improved DC breakdown strength. Excellent thermal oxidation stability confirmed by oxidative induction time measurements.

Application of N-(4-Anilinophenyl)maleimide in Developing a Multifunctional Additive for Styrene-Butadiene Rubber

Luo, Kaiqiang, et al. Polymer Degradation and Stability 177 (2020): 109181.

N-(4-Anilinophenyl)maleimide (MC) is a widely utilized antioxidant in rubber compounds for thermo-oxidative stabilization. However, its direct application in styrene-butadiene rubber (SBR) can negatively impact vulcanization efficiency. This work used N-(4-anilinophenyl)maleimide as the antioxidant building block for a thiol-ene coupling with 2-mercaptobenzothiazole (MBT) to produce an accelerator-modified antioxidant (termed BTC). The study compared SBR formulations containing MBT, MC, and the BTC adduct and found that BTC delivered the best balance of vulcanization efficiency, mechanical performance, and thermo-oxidative stabilization.
BTC Synthesis Procedure: BTC was synthesized via a thiol-ene click reaction between MC and 2-mercaptobenzothiazole (MBT). In a typical procedure, MC (4.0 g) and MBT (2.6 g, slightly excess) were dissolved in tetrahydrofuran (THF, ~80 mL) with triethylamine (TEA, 1.6 mL) as a catalyst. The mixture was heated at 55°C for 8 hours under a nitrogen atmosphere. The crude solid product was obtained after solvent removal via rotary evaporation. Unreacted MBT was eliminated using a NaOH/water solution, leveraging MBT's solubility in alkaline conditions. The purified BTC was washed repeatedly with deionized water until neutral pH and dried thoroughly in a vacuum oven at 50°C.
Key Performance: Converting MC into the higher-molecular-weight BTC adduct reduced the negative impact on cure and in fact accelerated vulcanization relative to the MC-containing system. The BTC molecule, which contains aromatic amino and thioether functionalities, contributed significantly to improved resistance against thermo-oxidative aging in SBR composites. The BTC/SBR composites demonstrated an optimal combination of cure efficiency, mechanical performance, and long-term stabilization compared with MBT/SBR and MBT+MC/SBR systems.