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4,4'-Oxydianiline

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4,4'-Oxydianiline
Names
IUPAC name
4,4'-oxydianiline
Other names
4,4'-diaminodiphenyl ether; 4-aminophenyl ether; 4,4'-oxybisbenzenamine; bis(4-aminophenyl) ether; 4,4'-ODA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.707 Edit this at Wikidata
KEGG
  • InChI=1S/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2 checkY
    Key: HLBLWEWZXPIGSM-UHFFFAOYSA-N checkY
  • InChI=1/C12H12N2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2
    Key: HLBLWEWZXPIGSM-UHFFFAOYAM
  • O(c1ccc(N)cc1)c2ccc(cc2)N
Properties
C12H12N2O
Molar mass 200.24 g/mol
Appearance Colorless crystalline solid
Melting point 188 to 192 °C (370 to 378 °F; 461 to 465 K)
Boiling point 219 °C (426 °F; 492 K)
Insoluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
2
Flash point 219 °C (426 °F; 492 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

4,4’-Oxydianiline is an organic compound with the formula O(C6H4NH2)2. It is an ether derivative of aniline. This colourless solid is a useful monomer and cross-linking agent for polymers, especially the polyimides, such as Kapton.

Uses

4,4’-Oxydianiline is used in the production of a wide variety of polymer resins. The primary use lies in the production of polyimide and poly(ester)imide resins. These resins are used for their temperature-resistant properties and are utilized in products including wire enamels, coatings, film, adhesives, insulating varnishes, coated fabrics, flame-retardant fibers, oil sealants and retainers, insulation for cables and printed circuits, and laminates and composite for aerospace vehicles.

Other applications of 4,4’-oxydianiline include the production of poly(amide)imide resins (which are used in the manufacture of heat-resistant wire enamels and coatings), as an intermediate in the manufacture of epoxy resins and adhesives, and in the production of aromatic polyether imides.[1]

A specific reaction involving industrial use of 4,4’-oxydianiline is in the production of thermostable poly(amideurea) acids, which can be prepared from 4,4’-oxydianiline, pyromellitic dianhydride, and diisocyanates. These poly(amideurea) acids can be used as intermediates in the syntheses of poly(imideurea)s:[2]

References

  1. ^ 11th ROC: 4,4'-Oxydianiline
  2. ^ Chiria, C.I; Tanasã, F. (2000). "Polyureas". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. doi:10.1002/14356007.d21_d01.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  • MSDS Material Safety Data Sheet provided by Sigma-Aldrich.