412805

4,4′-Methylenebis(N,N-diglycidylaniline)

• Synonym(s): 4,4′-Methylenebis[N ,N -bis(oxiranylmethyl)aniline], 4,4′-Methylenedianiline tetraglycidyl ether, N ,N ,N ′,N ′-Tetraglycidyl-4,4′-methylenebisbenzenamine, N ,N ,N ′,N ′-Tetraglycidyl-4,4′-methylenedianiline, Bis[4-(diglycidylamino)phenyl]methane
• Empirical Formula (Hill Notation): C₂₅H₃₀N₂O₄
• CAS Number: 28768-32-3
• Molecular Weight: 422.52
• EC Number: 249-204-3
• MDL number: MFCD00661161
• UNSPSC Code: 12162002
• PubChem Substance ID: 24865824
• NACRES: NA.23

Properties

• form: viscous liquid
• refractive index: n20/D 1.601 (lit.)
• density: 1.15 g/mL at 25 °C (lit.)
• SMILES string: C1OC1CN(CC2CO2)c3ccc(Cc4ccc(cc4)N(CC5CO5)CC6CO6)cc3
• InChI: 1S/C25H30N2O4/c1-5-20(26(10-22-14-28-22)11-23-15-29-23)6-2-18(1)9-19-3-7-21(8-4-19)27(12-24-16-30-24)13-25-17-31-25/h1-8,22-25H,9-17H2
• InChI key: FAUAZXVRLVIARB-UHFFFAOYSA-N

Description

General description

4,4′-Methylenebis(N,N-diglycidylaniline) (MDGA) is a bifunctional monomer possessing two epoxy groups (glycidyl groups) and two amine groups. It is commonly used as a monomer in the production of thermosetting polymers, particularly epoxy resins. MDGA-based epoxy resins can exhibit desirable properties such as high strength, chemical resistance, and thermal stability, which makes them suitable for a wide range of applications such as adhesives, coatings, composites, and electronic encapsulation.

Application

4,4′-Methylenebis(N,N-diglycidylaniline) can be used:

• As a starting material to synthesize UV-curable tetra-functional epoxy acrylate (EA4), which is used as a crosslinker for UV-curable resins.
• In the synthesis of bismaleimide/diallyl bisphenol A (BMI/DBA)–epoxy interpenetrating network resins, which have potential applications in the aerospace and automotive industries because of their high thermal stability and low activation energy.
• As a crosslinking agent in the production of biocompatible materials, such as hydrogels and other tissue engineering scaffolds. Its ability to form strong and stable crosslinks makes it valuable in the creation of medical devices, implants, and drug delivery systems. Additionally, it is utilized in the synthesis of biocompatible polymers and materials with tailored properties for biomedical applications.

4,4′-Methylenebis(N,N-diglycidylaniline) can be also used as a precursor to synthesize:

• Poly(hexamethylene biguanide) based polymer networks which are applicable as catalysts for the transesterification of vegetable oils.
• Tetra-functional epoxy-acrylate UV curable resins.

It can also be used as a crosslinker to functionalize carbon nanotubes to improve their mechanical strength.

Safety Information

• Pictograms: GHS08,GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H317,H341,H411
• Precautionary Statements: P202 - P261 - P273 - P280 - P302 + P352 - P308 + P313
• Hazard Classifications: Aquatic Chronic 2 - Muta. 2 - Skin Sens. 1
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 2
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves