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

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4,4′-Methylenebis(N,N-diglycidylaniline)
TGDDM structure
Names
IUPAC name
4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-N,N-bis(oxiran-2-ylmethyl)aniline[3][4]
Other names
TGDDM; tetraglycidyl-4,4′-methylenedianiline[1][2]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.044.717 Edit this at Wikidata
EC Number
  • 249-204-3
UNII
  • 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[5][3][4]
  • C1C(O1)CN(CC2CO2)C3=CC=C(C=C3)CC4=CC=C(C=C4)N(CC5CO5)CC6CO6[5][3][4]
Properties
C25H30N2O4[5][3][4]
Molar mass 422.52 g/mol
Appearance Yellow sticky liquid[6]
Density 1.15 g/cm3 (25 °C)[1]
Boiling point 619.3 °C (760 mm Hg)[1]
log P 2.4854[1]
Vapor pressure 2.9×10−15 mm Hg (25 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4,4′-Methylenebis(N,N-diglycidylaniline), commonly abbreviated as 4-DGA or TGDDM,[7] is a tetrafunctional aniline-based epoxy resin monomer. It can undergo ring-opening polymerization with various acid anhydride curing agents—such as methyl tetrahydrophthalic anhydride (MTHPA), methylhexahydrophthalic anhydride (MHHPA), maleic anhydride, and glutaric anhydride—to form highly crosslinked thermosetting networks. TGDDM not only contributes rigid aromatic rings that help adjust the glass transition temperature (Tg) of the network but also provides tertiary amine groups that can catalyze the virtrification process and transesterification reactions.[8]

References

[edit]
  1. ^ a b c d e "4,4'-Methylenebis(N,N-diglycidylaniline)". chemsrc.com. Retrieved 2025-05-17.
  2. ^ "4,4'-Methylenebis(N,N-diglycidylaniline) | 28768-32-3". ChemicalBook. Retrieved 2025-05-17.
  3. ^ a b c d "4,4′-Methylenebis[N,N-bis(2-oxiranylmethyl)aniline]". ChemSpider. Retrieved 2025-05-17.
  4. ^ a b c d "4,4'-methylenebis[N,N-bis(2,3-epoxypropyl)aniline]". European Chemicals Agency. Retrieved 2025-05-17.
  5. ^ a b c "PubChemLite - 28768-32-3 (C25H30N2O4)". pubchemlite.lcsb.uni.lu. Retrieved 2025-05-17.
  6. ^ ChemicalBook. "4,4′-Methylenebis(N,N-diglycidylaniline)". ChemicalBook. Retrieved 2025-05-17.
  7. ^ Rocks, Jens; George, Graeme A; Vohwinkel, Friedrich (November 2003). "Curing kinetics and thermomechanical behaviour of co-anhydride cured aminoglycidyl epoxy resins". Polymer International. 52 (11): 1758–1766. doi:10.1002/pi.1286. ISSN 0959-8103. Retrieved 2025-05-17.
  8. ^ Giebler, Michael; Sperling, Clemens; Kaiser, Simon; Duretek, Ivica; Schlögl, Sandra (2020-05-17). "Epoxy-Anhydride Vitrimers from Aminoglycidyl Resins with High Glass Transition Temperature and Efficient Stress Relaxation". Polymers. 12 (5): 1148. doi:10.3390/polym12051148. ISSN 2073-4360. PMC 7284387. PMID 32429574.
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