Industrial grade98%，N,N'-1,3-Phenylene bismaleimide CA 3006-93-7

What is N,N'-1,3-Phenylene bismaleimide? How does it work? What are its industrial applications?

1. What is N,N'-1,3-Phenylene bismaleimide? How does it work?

N,N'-1,3-Phenylene bismaleimide, also known as m-phenylene bismaleimide, is a bifunctional compound with two maleimide rings bridged by a meta-phenylene group. Its chemical formula is C14H8N2O4, and its CAS number is 3006-93-7. It is a yellow to yellowish-brown crystalline powder. The molecule contains two highly reactive maleimide double bonds, allowing it to be co-vulcanized with rubber peroxide systems and also to self-polymerize at high temperatures to form a heat-resistant resin network. This makes it widely used in rubber vulcanization aids, heat-resistant modification of plastics, high-temperature resins and composites, insulation and electronic materials, and other industrial fields. Its trade name, such as HVA-2, is widely known in the rubber industry.

Basic information : Chinese name: N,N'-1,3-Phenylene bismaleimide (also known as N,N'-1,3-Phenylidene bismaleimide, 1,3-phenylene dimaleimide); English name: N,N'-1,3-Phenylene bismaleimide (abbreviation BMI); CAS number: 3006-93-7; Molecular formula: C14H8N2O4; Molecular weight: 268.23; Appearance: yellow to yellowish-brown crystalline powder; Insoluble in water, soluble in organic solvents such as acetone, dimethylformamide, and xylene; Melting point: approximately 200℃; Synonyms: Antioxidant PM, sulfurizing agent PM, HVA-2, VANAX MBM, etc.

Structurally , m-phenylenebismaleimide consists of two maleimide rings (2,5-pyrroledione) bridged by meta-(1,3) phenylene groups: each maleimide ring contains a carbon-carbon double bond conjugated with two carbonyl groups and an imine nitrogen atom, with the nitrogen atoms of the two rings connected to the 1 and 3 positions of the benzene ring, respectively. The molecule has a rigid planar framework containing two symmetrical reactive double bonds—this is a manifestation of its bifunctional structure and the structural basis for its co-vulcanization with rubber and thermal polymerization to form a heat-resistant network.

physical properties , m-phenylenebismaleimide is a yellow to yellowish-brown crystalline powder with no special odor; it is insoluble in water but soluble in organic solvents such as acetone, dimethylformamide, and xylene; its melting point is about 200℃; it is chemically stable at room temperature and needs to be stored in a sealed container away from light and moisture; as a powder additive, it has good dispersibility and is easy to add to rubber and resin formulations.

Chemically , m-phenylenebismaleimide is a bifunctional maleimide: its two electron-deficient carbon-carbon double bonds are highly reactive, capable of Michael addition with amines, and can participate in free radical polymerization and high-temperature self-polymerization; it acts as a co-crosslinking agent in rubber peroxide vulcanization systems to increase crosslinking density; it self-polymerizes at high temperatures to form a heat-resistant crosslinking network; the maleimide ring can be hydrolyzed and opened under strong alkali or prolonged high-temperature conditions; its overall chemical properties are stable, and it belongs to the category of heat-resistant organic intermediates.

Why does N,N'-1,3-Phenylene bismaleimide play these roles in industrial fields such as rubber vulcanization, plastic modification, high-temperature resistant resins, and insulating materials? Its mechanism of action mainly includes the following:

Electron-deficient double bond reactivity mechanism : The carbon-carbon double bond of maleimide is conjugated with two carbonyl groups and is in an electron-deficient state, making it highly reactive with free radicals and nucleophiles—this is the basis for its participation in sulfurization, crosslinking and polymerization reactions.

Bifunctional crosslinking mechanism : The molecule contains two reactive double bonds, which can be simultaneously connected to two polymer chains to form a network structure with high crosslinking density—the basis for rubber co-vulcanization and thermosetting molding.

Rigid aromatic ring heat resistance mechanism : The m-phenylene aromatic ring skeleton and the five-membered imide ring endow the molecule with high rigidity, and after cross-linking, a dense high-temperature resistant network is formed - the basis for heat-resistant modification and high-temperature resistant resin applications.

Free radical capture and stabilization mechanism : Maleimide can capture excess free radicals generated during peroxide vulcanization and form stable adducts, inhibiting side reactions, improving crosslinking efficiency, and improving the heat resistance and compression set of rubber.

Thermal polymerization network mechanism : Maleimide double bonds can self-polymerize at high temperatures without a catalyst, forming a dense network with a high glass transition temperature—the source of the high-temperature resistance of BMI resin.

II. All applications of industrial-grade N,N'-1,3-Phenylene bismaleimide

1. Rubber industry

Peroxide vulcanization co-crosslinking agent

It is used in combination with peroxides as a rubber co-crosslinking agent to increase crosslinking density and improve heat resistance and compression set.

Corresponding products: Rubber products such as EPDM, nitrile rubber, hydrogenated nitrile rubber, and chlorinated polyethylene.

Heat-resistant rubber products

Used for seals, hoses, and transmission components in high-temperature environments, extending their service life.

Corresponding products: heat-resistant sealing rings, high-temperature hoses, transmission belts, etc.

2. Plastics Modification Field

Heat-resistant modification of ABS and AS resins

It can be used as a heat-resistant modifier to increase the heat distortion temperature of resins such as ABS and AS, thereby improving their heat resistance.

Corresponding products: heat-resistant ABS, appliance housings, automotive interior parts, etc.

Heat-resistant modification of PVC and polypropylene

Improve the heat resistance and rigidity of plastics such as PVC and polypropylene, and expand the application temperature range.

Corresponding products: heat-resistant PVC products, modified polypropylene, etc.

3. High-temperature resistant resins and composite materials

BMI high-temperature resistant resin matrix

Bismaleimide resin has a high glass transition temperature and excellent heat resistance, making it suitable as a matrix for high-performance composite materials.

Corresponding products: BMI resin, prepreg, composite material components, etc.

Copper clad laminate and circuit board substrate

It is used as a substrate resin for copper-clad laminates and in high-performance printed circuit boards.

Corresponding products: copper clad laminates, PCB substrates, electronic substrates, etc.

Fiber reinforced composite materials

Combined with glass fiber and carbon fiber, high-temperature resistant structural materials are prepared.

Corresponding products: carbon fiber composite materials, fiberglass components, etc.

4. Adhesives and Insulation Materials

High-temperature resistant adhesives

It is used as a component of high-temperature resistant adhesives for structural bonding in high-temperature environments.

Corresponding products: high-temperature resistant adhesives, structural adhesives, etc.

Electrical insulation and electronic packaging

Used in heat-resistant insulating varnishes and electronic packaging materials to ensure the temperature resistance and reliability of electrical and electronic devices.

Corresponding products: insulating varnish, electronic packaging materials, heat-resistant insulating components, etc.

III . Summary

N,N'-1,3-Phenylene bismaleimide (CAS 3006-93-7) is a bifunctional compound consisting of two maleimide rings bridged by a meta-phenylene group. The two electron-deficient double bonds allow it to efficiently co-crosslink with rubber peroxide systems and also to self-polymerize at high temperatures into heat-resistant resin networks. The rigid aromatic ring skeleton endows the crosslinked products with excellent heat resistance. In rubber factories, it acts as a vulcanizing agent to make seals more heat-resistant; in plastic modification, it makes ABS appliance casings more temperature-resistant; in composite materials and copper-clad laminates, it constructs high-temperature resistant matrices; and in insulating varnishes and encapsulation materials, it safeguards electrical reliability—quietly supporting the rubber, plastics, electronics, and composite materials industries as an industrial additive and resin raw material. Understanding its bismaleimide structure and the reactivity of its double bonds is key to understanding why it has become a perennial and crucial monomer in the world of heat-resistant polymer materials.