Diethyl toluene diamine

Diethyl toluene diamine (DETDA) is a liquid aromatic organic molecule[2] with formula C11H18N2. It is chemically an aromatic diamine and has the CAS Registry number of 68479-98-1. It has more than one isomer and the mixture of the two main isomers is given a different CAS number of 75389-89-8.[3] It is often marketed as a less toxic version of 4,4'-methylenedianiline (MDA). It is also used to replace the more toxic 4,4'-methylenebis(2-chloroaniline) (MOCA).[4] The toxicology is reasonably well understood.[5]

Diethyl toluene diamine

Main component
Names
IUPAC name
2,4-Diethyl-6-methylbenzene-1,3-diamine
Other names
DETDA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.064.414
  • InChI=1S/C11H18N2/c1-4-8-6-7(3)10(12)9(5-2)11(8)13/h6H,4-5,12-13H2,1-3H3
    Key: PISLZQACAJMAIO-UHFFFAOYSA-N
  • CCC1=C(C(=C(C(=C1)C)N)CC)N
Properties
C11H18N2
Molar mass 178.279 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H312, H319, H373, H410
P260, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P317, P319, P321, P330, P337+P317, P362+P364, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

DETDA is an industrial chemical used in the injection molding industry.[6] One of the reasons it is used in RIM is because it gives very short demold times.[7] It is also used extensively in polyurethanes and in both spray polyureas[8] and elastomers.[9][10] When used in elastomer production these can be used as an energy absorbing system in automobiles.[11] It is a diamine and thus in polymer science terms is a Chain extender rather than a chain terminator. Chain extenders (f = 2) and cross linkers (f ≥ 3) are low molecular weight amine terminated compounds that play an important role in polyurea compounds, elastomers and adhesives. DETDA is one such amine and is used extensively in reaction injection molding (RIM) and in polyurethane and polyurea elastomer formulations.[12]

Pyrolysis in combination with other materials can produce a carbon-based molecular sieve.[13] Carbon nanotubes have also been produced and studied with the material.[14] There are other more specialist uses for the material too.[15]

As it is an aromatic amine, its rate of cure is much slower than aliphatic amines and thus used with epoxy resin systems to lengthen the working time or potlife.[16] These are then used in adhesives, sealants, and paints or coatings.[17] It is often used with epoxy resins for its excellent mechanical properties.[18] Epoxy formulations based on DETDA also tend to have good high temperature properties.[19]

Supply

DETDA is produced globally and is thus fairly strategically important.[20][21]

See also

References
  1. "1,3-Benzenediamine, 2,4-diethyl-6-methyl-". pubchem.ncbi.nlm.nih.gov. Retrieved 27 March 2022.
  2. "Diethyltoluenediamine | 68479-98-1". www.chemicalbook.com. Retrieved 2022-03-24.
  3. PubChem. "Detda". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-24.
  4. Gantrade. "DETDA: A Liquid that Delivers the Hard and Tough". www.gantrade.com. Retrieved 2022-03-24.
  5. Babin, Michael (1997). "The uptake and distribution of diethyltoluenediamine in the male sprague dawley rat". Louisiana State University.
  6. EP application 0383100, Nodelman, Neil H., "Process and compositions for production of moldings", published 1990-08-22, assigned to Mobay Corp., since withdrawn.
  7. "Classic PU Patent of the Month: Polyurethane-Polyurea RIM Elastomers (Bayer 1976)". Innovation in Polyurethanes. 2014-12-22. Retrieved 2022-03-24.
  8. "DETDA (E100) Curing Agent for Spray Polyurea Coating". www.exceedchemical.com. Retrieved 2022-03-24.
  9. US 4581433, Potter, Terry A.; Markusch, Peter H. & Prepelka, David J., "Elastomer polyurethane-polyurea coatings based On bis(4-isocyanatocyclohexyl)methane", published 1986-04-08, assigned to Mobay Corp.
  10. US 4482690, Orphanides, Gus G., "Process for the production of polyurethane urea elastomers", published 1984-11-13, assigned to Air Products and Chemicals Inc.
  11. CA 2785900, Zeller, Frank, "Energy absorbing system for vehicles", published 2018-03-06, assigned to Texas Research International Inc.
  12. EP 3433294, Makal, Umit G.; Loeber, George H. & Suragani Venu, Lalith B., "Melt processable thermoplastic polyurethane-urea elastomers", published 2021-09-01, assigned to Lubrizol Advanced Materials Inc.
  13. Fu, Shilu; Wenz, Graham B.; Sanders, Edgar S.; Kulkarni, Sudhir S.; Qiu, Wulin; Ma, Canghai; Koros, William J. (2016-12-15). "Effects of pyrolysis conditions on gas separation properties of 6FDA/DETDA:DABA(3:2) derived carbon molecular sieve membranes". Journal of Membrane Science. 520: 699–711. doi:10.1016/j.memsci.2016.08.013. ISSN 0376-7388.
  14. Ajori, S.; Ansari, R. (2015-02-01). "Vibrational characteristics of diethyltoluenediamines (DETDA) functionalized carbon nanotubes using molecular dynamics simulations". Physica B: Condensed Matter. 459: 58–61. Bibcode:2015PhyB..459...58A. doi:10.1016/j.physb.2014.11.101. ISSN 0921-4526.
  15. Ren, Shitong (2015-01-16). "Synthesis, characterization, and polymerization of a novel benzoxazine based on diethyltoluenediamine". Journal of Applied Polymer Science. 132 (17). doi:10.1002/app.41920.
  16. US 9057002, Padilla-Acevedo, Angela I.; Valette, Ludovic & Mullins, Michael J. et al., "Curable resin compositions", published 2015-06-16, assigned to Dow Global Technologies LLC
  17. J-C. Huang; Y-T. Chu (1996-03-01). "Blend-Curing of Epoxies with Jeffamine® and Diethyltoluenediamine". Journal of Polymer Engineering. 16 (1–2): 51–72. doi:10.1515/POLYENG.1996.16.1-2.51. ISSN 2191-0340. S2CID 138046510.
  18. Komuves, Francis; Kelkar, Ajit; Mohan, Ram; Kelkar, Vinaya (2010-04-12), "Prediction of Mechanical Properties of EPON 862 (DGEBF)-W (DETDA) Using MD Simulations", 51st AIAA/ASME/ASCE/AHS/ASC Structures, Structural Dynamics, and Materials Conference, Structures, Structural Dynamics, and Materials and Co-located Conferences, American Institute of Aeronautics and Astronautics, doi:10.2514/6.2010-2814, ISBN 978-1-60086-961-7, retrieved 2022-03-24
  19. Poynton, Gary (2014). "Multi‐component Epoxy Resin Formulation for High Temperature Applications PhD thesis" (PDF). Manchester University (UK).
  20. "Global DETDA and DMTDA Market - Size Research with Latest Opportunities 2021: Top Growing Factors, Market Dynamic Analysis and Development Suggestions, Emerging Technologies Forecast to 2026". rivercountry.newschannelnebraska.com. Retrieved 2022-03-24.
  21. "DETDA and DMTDA Market Size, Status, Global Outlook and Forecast 2022-2026, COVID-19 Impact, Market Trends, Share, Size". MarketWatch. Retrieved 2022-03-24.

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