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412805

Sigma-Aldrich

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

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About This Item

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

form

viscous liquid

Quality Level

100

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

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.

Signal Word

Warning

Hazard Statements

H317,H341,H411

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3783V
WXBF1274V
WXBD6896V
WXBD4367V
WXBD3420V

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L Kanerva et al.
Dermatology (Basel, Switzerland), 201(1), 29-33 (2000-09-06)
Very little is known about allergic contact dermatitis (ACD) from preimpregnated epoxy products (prepregs). To describe a patient with occupational ACD from prepregs, and report new quantitative data on the content of prepregs. A laminator developed work-related vesicular hand dermatitis.
D Burrows et al.
Contact dermatitis, 11(2), 80-82 (1984-08-01)
An outbreak of dermatitis occurred in an aircraft factory using epoxy resin composite material. Of 25 operatives, 14 gave positive patch test reactions to the composite material and/or diglycidylether of bisphenol A (DGEBA), tetraglycidyl-4,4'-methylene dianiline (TGMDA), and o-diglycidyl phthalate. This
F Ayala et al.
Contact dermatitis, 22(5), 262-266 (1990-05-01)
Thin-layer chromatography, column chromatography, mass spectrometry and nuclear magnetic resonance were used to investigate the chemical constituents and haptens responsible in 2 different circumstances where allergic contact dermatitis from composite materials was suspected. In an aircraft factory where epoxy resins
Michael Giebler et al.
Polymers, 12(5) (2020-05-21)
Epoxy-anhydride vitrimers are covalent adaptable networks, which undergo associative bond exchange reactions at elevated temperature. Their service temperature is influenced by the glass transition temperature (Tg) as well as the topology freezing transition temperature (Tv), at which the covalent bond

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