diglycidyl aniline

• Diglycidylaniline
• N,N-Diglycidylaniline
• N,N-bis(oxiran-2-ylmethyl)aniline{{Cite web |last=PubChem |title=N,N-bis(oxiran-2-ylmethyl)aniline |url=https://pubchem.ncbi.nlm.nih.gov/substance/464389778 |access-date=2022-08-04 |website=pubchem.ncbi.nlm.nih.gov |language=en}}
• Oxiranemethanamine, N-(oxiranylmethyl)-N-phenyl-{{Cite web |last=PubChem |title=2095-06-9 |url=https://pubchem.ncbi.nlm.nih.gov/substance/404798334 |access-date=2022-08-04 |website=pubchem.ncbi.nlm.nih.gov |language=en}}
• Bis(epoxypropyl)phenylamine
• Bis(2,3-epoxypropyl)aniline
• Bis(oxiranylmethyl)benzenamine
• Benzenamine, bis(oxiranylmethyl)-

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.{{Cite journal |last=Crivello |first=James V. |date=2006 |title=Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization |url=https://doi.org/10.1002/pola.21761 |journal=Journal of Polymer Science Part A: Polymer Chemistry |volume=44 |issue=21 |pages=6435–6448 |doi=10.1002/pola.21761 |bibcode=2006JPoSA..44.6435C |issn=0887-624X}} This diglycidyl compound being basic and nitrogen based, does not need this type of catalyst.{{Cite book |last=Panda |first=Dr H |title=Epoxy Resins Technology Handbook (Manufacturing Process, Synthesis, Epoxy Resin Adhesives and Epoxy Coatings |publisher=Asia Pacific Business Press Inc |year=2019 |isbn=978-8178331829 |edition=2nd |pages=38}}{{Cite journal |last1=Jung |first1=Woo-Hyuk |last2=Ha |first2=Eun-Ju |last3=Chung |first3=Il doo |last4=Lee |first4=Jang-Oo |date=2008-08-01 |title=Synthesis of aniline-based azopolymers for surface relief grating |url=https://doi.org/10.1007/BF03218555 |journal=Macromolecular Research |language=en |volume=16 |issue=6 |pages=532–538 |doi=10.1007/BF03218555 |s2cid=94372490 |issn=2092-7673}} One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight in addition to viscosity.

The use of the diluent in epoxy systems affects the mechanical properties and microstructure of epoxy resins.{{Cite journal |last1=Pastarnokienė |first1=Liepa |last2=Jonikaitė-Švėgždienė |first2=Jūratė |last3=Lapinskaitė |first3=Neringa |last4=Kulbokaitė |first4=Rūta |last5=Bočkuvienė |first5=Alma |last6=Kochanė |first6=Tatjana |last7=Makuška |first7=Ričardas |date=2023-07-01 |title=The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings |url=https://doi.org/10.1007/s11998-022-00737-4 |journal=Journal of Coatings Technology and Research |language=en |volume=20 |issue=4 |pages=1207–1221 |doi=10.1007/s11998-022-00737-4 |s2cid=256749849 |issn=1935-3804}}{{Cite journal |last1=Matějka |first1=Libor |last2=Dušek |first2=Karel |last3=Dobáš |first3=Ivan |date=1985-10-01 |title=Curing of epoxy resins with amines |url=https://doi.org/10.1007/BF00254954 |journal=Polymer Bulletin |language=en |volume=14 |issue=3 |pages=309–315 |doi=10.1007/BF00254954 |s2cid=92434408 |issn=1436-2449}}{{Cite journal |last1=Khalina |first1=Morteza |last2=Beheshty |first2=Mohammad Hosain |last3=Salimi |first3=Ali |date=2019-08-01 |title=The effect of reactive diluent on mechanical properties and microstructure of epoxy resins |url=https://doi.org/10.1007/s00289-018-2577-6 |journal=Polymer Bulletin |language=en |volume=76 |issue=8 |pages=3905–3927 |doi=10.1007/s00289-018-2577-6 |s2cid=105389177 |issn=1436-2449}}{{Cite journal |last1=Roşu |first1=D |last2=Caşcaval |first2=C. N |last3=Mustątǎ |first3=F |last4=Ciobanu |first4=C |date=2002-02-07 |title=Cure kinetics of epoxy resins studied by non-isothermal DSC data |url=https://www.sciencedirect.com/science/article/pii/S0040603101006724 |journal=Thermochimica Acta |language=en |volume=383 |issue=1 |pages=119–127 |doi=10.1016/S0040-6031(01)00672-4 |issn=0040-6031}}{{Cite journal |last1=Klee |first1=Joachim |last2=Flammersheim |first2=Hans Jurgen |title=Linear Addition Polymers and Cyclic Oligomers of N,N-Diglycidyl Aniline and Amines -Uncrosslinked Epoxide Amine Addition Polymers |journal=Macromolecular Chemistry and Physics |year=2002 |volume=203 |pages=100–108 |doi=10.1002/1521-3935(20020101)203:1<100::AID-MACP100>3.0.CO;2-J |url=https://onlinelibrary.wiley.com/doi/epdf/10.1002/1521-3935%2820020101%29203%3A1%3C100%3A%3AAID-MACP100%3E3.0.CO%3B2-J |edition=203}} The kinetics of cure of this Diglycidyl amine with epoxy resin networks have been studied.{{Cite journal |last1=John |first1=N. A. St |last2=George |first2=G. A. |date=1994-01-01 |title=Diglycidyl amine — epoxy resin networks: Kinetics and mechanisms of cure |url=https://dx.doi.org/10.1016/0079-6700%2894%2990032-9 |journal=Progress in Polymer Science |language=en |volume=19 |issue=5 |pages=755–795 |doi=10.1016/0079-6700(94)90032-9 |issn=0079-6700}} It has also been used to synthesize other materials including ion-exchange resins.{{Cite journal |last1=Ergozhin |first1=E. E. |last2=Begenova |first2=B. E. |last3=Chalov |first3=T. K. |date=2007-03-01 |title=Synthesis and study of physicochemical, acid-base, and complexing properties of ion exchangers based on glycidyl derivatives of aromatic compounds and polyamines |url=https://doi.org/10.1134/S1070427207030238 |journal=Russian Journal of Applied Chemistry |language=en |volume=80 |issue=3 |pages=472–476 |doi=10.1134/S1070427207030238 |s2cid=92895375 |issn=1608-3296}}{{Cite journal |last1=Johncock |first1=P. |last2=Cunliffe |first2=A. V. |date=1992-01-01 |title=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 |url=https://dx.doi.org/10.1016/0032-3861%2892%2990533-3 |journal=Polymer |language=en |volume=33 |issue=11 |pages=2392–2401 |doi=10.1016/0032-3861(92)90533-3 |issn=0032-3861}}{{Cite journal |last1=John |first1=N. A. St |last2=George |first2=G. A. |date=1994-01-01 |title=Diglycidyl amine — epoxy resin networks: Kinetics and mechanisms of cure |url=https://dx.doi.org/10.1016/0079-6700%2894%2990032-9 |journal=Progress in Polymer Science |language=en |volume=19 |issue=5 |pages=755–795 |doi=10.1016/0079-6700(94)90032-9 |issn=0079-6700}}

The toxicity profile has been studied and published.{{Cite journal |last=Seiler |first=J.P. |date=March 1984 |title=The mutagenicity of mono- and di-functional aromatic glycidyl compounds |url=https://linkinghub.elsevier.com/retrieve/pii/0165121884901162 |journal=Mutation Research/Genetic Toxicology |language=en |volume=135 |issue=3 |pages=159–167 |doi=10.1016/0165-1218(84)90116-2|pmid=6369127 }}

{{reflist}}

• {{Cite book|url=https://www.worldcat.org/oclc/182890|title=Epoxy resin technology.|date=1968|publisher=Interscience Publishers|others=Paul F. Bruins, Polytechnic Institute of Brooklyn|isbn=0-470-11390-1|location=New York|oclc=182890}}
• {{Cite book|last=Flick|first=Ernest W.|url=https://www.worldcat.org/oclc/915134542|title=Epoxy resins, curing agents, compounds, and modifiers : an industrial guide|date=1993|isbn=978-0-8155-1708-5|location=Park Ridge, NJ|oclc=915134542}}

• [http://www.accatalysts.com/DOCS/TECHNIREZ/TechnirezR_GAN_TDS_Final.pdf Technical Data Sheet]
• [https://www.gabrielchem.com/product/royoxy-rad-104/ Huntsman commercial product]
• [https://www.parchem.com/chemical-supplier-distributor/Diglycidyl-ether-based-on-aniline-017685.aspx Diglycidyl ether based on aniline Parchem.com ]

Category:Reactive diluents