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Diglycidyl aniline

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Diglycidyl aniline
Names
IUPAC name
N,N-bis(oxiran-2-ylmethyl)aniline
Other names
Diglycidylaniline; Bis(2,3-epoxypropyl)aniline; Bis(epoxypropyl)phenylamine; Diglycidyl aniline; N,N-Bis(2,3-epoxypropyl)aniline; N,N-Di(2,3-epoxypropyl)aniline; N,N-Diglycidylaniline; N-(Oxiranylmethyl)-N-phenyloxiranemethanamine; N-N-Diglycidylphenylamine; N-(2-oxiranylmethyl)-N-phenyl-2-oxiranemethanamine; N,N-bis(2,3-epoxypropyl)-aniline; N-(oxiranylmethyl)-N-phenyl-oxiranemethanamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.599 Edit this at Wikidata
EC Number
  • 218-259-5
UNII
  • InChI=1S/C12H15NO2/c1-2-4-10(5-3-1)13(6-11-8-14-11)7-12-9-15-12/h1-5,11-12H,6-9H2
    Key: JAYXSROKFZAHRQ-UHFFFAOYSA-N
  • C1C(O1)CN(CC2CO2)C3=CC=CC=C3
Properties
C12H15NO2
Molar mass 205.255 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family.[1] It is used to reduce the viscosity of epoxy resin systems.[2] It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9.[3][4] It is REACH registered in Europe with the EC number 218-259-5.[5] A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.[6][7]

Alternative names

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  • Diglycidylaniline
  • N,N-Diglycidylaniline
  • N,N-bis(oxiran-2-ylmethyl)aniline[8]
  • Oxiranemethanamine, N-(oxiranylmethyl)-N-phenyl-[9]
  • Bis(epoxypropyl)phenylamine
  • Bis(2,3-epoxypropyl)aniline
  • Bis(oxiranylmethyl)benzenamine
  • Benzenamine, bis(oxiranylmethyl)-

Manufacture and synthesis

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Many glycidyl ethers are manufactured by addition of epichlorohydrin to a species with the aid of a Lewis acid as catalyst to form a halohydrin. This process is followed by washing with sodium hydroxide in a dehydrochlorination reaction.[10] This diglycidyl compound being basic and nitrogen based, does not need this type of catalyst.[11][12] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight in addition to viscosity.

Uses

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The use of the diluent in epoxy systems affects the mechanical properties and microstructure of epoxy resins.[13][14][15][16][17] The kinetics of cure of this Diglycidyl amine with epoxy resin networks have been studied.[18] It has also been used to synthesize other materials including ion-exchange resins.[19][20][21]

Toxicity

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The toxicity profile has been studied and published.[22]

References

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  1. ^ "diglycidylaniline - MeSH - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2022-08-04.
  2. ^ Dušek, Karel (1989), Lemstra, P. J.; Kleintjens, L. A. (eds.), "Curing of Epoxy Matrices", Integration of Fundamental Polymer Science and Technology—3, Dordrecht: Springer Netherlands, pp. 265–273, doi:10.1007/978-94-009-1115-4_30, ISBN 978-94-009-1115-4, retrieved 2022-08-04
  3. ^ PubChem. "Diglycidylaniline". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-04.
  4. ^ PubChem. "2095-06-9". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-04.
  5. ^ "Substance Information - ECHA". echa.europa.eu. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
  6. ^ EP 2621994, Hefner, Robert E., "Epoxy resin compositions", published 2013-08-07, assigned to Dow Global Technologies LLC 
  7. ^ Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
  8. ^ PubChem. "N,N-bis(oxiran-2-ylmethyl)aniline". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-04.
  9. ^ PubChem. "2095-06-9". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-04.
  10. ^ Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry. 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN 0887-624X.
  11. ^ Panda, Dr H (2019). Epoxy Resins Technology Handbook (Manufacturing Process, Synthesis, Epoxy Resin Adhesives and Epoxy Coatings (2nd ed.). Asia Pacific Business Press Inc. p. 38. ISBN 978-8178331829.
  12. ^ Jung, Woo-Hyuk; Ha, Eun-Ju; Chung, Il doo; Lee, Jang-Oo (2008-08-01). "Synthesis of aniline-based azopolymers for surface relief grating". Macromolecular Research. 16 (6): 532–538. doi:10.1007/BF03218555. ISSN 2092-7673. S2CID 94372490.
  13. ^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
  14. ^ Matějka, Libor; Dušek, Karel; Dobáš, Ivan (1985-10-01). "Curing of epoxy resins with amines". Polymer Bulletin. 14 (3): 309–315. doi:10.1007/BF00254954. ISSN 1436-2449. S2CID 92434408.
  15. ^ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.
  16. ^ Roşu, D; Caşcaval, C. N; Mustątǎ, F; Ciobanu, C (2002-02-07). "Cure kinetics of epoxy resins studied by non-isothermal DSC data". Thermochimica Acta. 383 (1): 119–127. doi:10.1016/S0040-6031(01)00672-4. ISSN 0040-6031.
  17. ^ Klee, Joachim; Flammersheim, Hans Jurgen (2002). "Linear Addition Polymers and Cyclic Oligomers of N,N-Diglycidyl Aniline and Amines -Uncrosslinked Epoxide Amine Addition Polymers". Macromolecular Chemistry and Physics. 203 (203 ed.): 100–108. doi:10.1002/1521-3935(20020101)203:1<100::AID-MACP100>3.0.CO;2-J.
  18. ^ John, N. A. St; George, G. A. (1994-01-01). "Diglycidyl amine — epoxy resin networks: Kinetics and mechanisms of cure". Progress in Polymer Science. 19 (5): 755–795. doi:10.1016/0079-6700(94)90032-9. ISSN 0079-6700.
  19. ^ Ergozhin, E. E.; Begenova, B. E.; Chalov, T. K. (2007-03-01). "Synthesis and study of physicochemical, acid-base, and complexing properties of ion exchangers based on glycidyl derivatives of aromatic compounds and polyamines". Russian Journal of Applied Chemistry. 80 (3): 472–476. doi:10.1134/S1070427207030238. ISSN 1608-3296. S2CID 92895375.
  20. ^ Johncock, P.; Cunliffe, A. V. (1992-01-01). "Structural features in epoxy networks from N,N-diglycidyl epoxies and amines: 2. Ether ring formation and polymer structure in the reactions of N,N-diglycidylaniline with aniline and substituted anilines". Polymer. 33 (11): 2392–2401. doi:10.1016/0032-3861(92)90533-3. ISSN 0032-3861.
  21. ^ John, N. A. St; George, G. A. (1994-01-01). "Diglycidyl amine — epoxy resin networks: Kinetics and mechanisms of cure". Progress in Polymer Science. 19 (5): 755–795. doi:10.1016/0079-6700(94)90032-9. ISSN 0079-6700.
  22. ^ Seiler, J.P. (March 1984). "The mutagenicity of mono- and di-functional aromatic glycidyl compounds". Mutation Research/Genetic Toxicology. 135 (3): 159–167. doi:10.1016/0165-1218(84)90116-2. PMID 6369127.

Further reading

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External websites

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