Chemistry:Diethyl toluene diamine

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Diethyl toluene diamine
Diethyltoluenediamine.svg
Main component
Names
IUPAC name
2,4-Diethyl-6-methylbenzene-1,3-diamine
Other names
DETDA
Identifiers
3D model (JSmol)
ChemSpider
Properties
C11H18N2
Molar mass 178.279 g·mol−1
Hazards
GHS pictograms GHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Warning
H302, H312, H319, H373, H410
P260, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P273, P280, P301+317Script error: No such module "Preview warning".Category:GHS errors, P302+352, P305+351+338, P317Script error: No such module "Preview warning".Category:GHS errors, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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]

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-" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/74980#section=Safety-and-Hazards. 
  2. ↑ "Diethyltoluenediamine | 68479-98-1". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5511671.htm. 
  3. ↑ PubChem. "Detda" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/24834553. 
  4. ↑ Gantrade. "DETDA: A Liquid that Delivers the Hard and Tough" (in en-us). https://www.gantrade.com/blog/detda-a-liquid-that-delivers-the-hard-and-tough. 
  5. ↑ Babin, Michael (1997). "The uptake and distribution of diethyltoluenediamine in the male sprague dawley rat". https://digitalcommons.lsu.edu/cgi/viewcontent.cgi?article=7379&context=gradschooldisstheses. 
  6. ↑ Nodelman, Neil H., "Process and compositions for production of moldings", EP patent application 0383100, published 1990-08-22, assigned to Mobay Corp., since withdrawn.
  7. ↑ "Classic PU Patent of the Month: Polyurethane-Polyurea RIM Elastomers (Bayer 1976)" (in en). 2014-12-22. https://purpatents.com/2014/12/22/classic-pu-patent-of-the-month-polyurethane-polyurea-rim-elastomers-bayer-1976/. 
  8. ↑ "DETDA (E100) Curing Agent for Spray Polyurea Coating". http://www.exceedchemical.com/sale-9110882-detda-e100-curing-agent-for-spray-polyurea-coating.html. 
  9. ↑ Potter, Terry A.; Peter H. Markusch & David J. Prepelka, "Elastomer polyurethane-polyurea coatings based On bis(4-isocyanatocyclohexyl)methane", US patent 4581433, published 1986-04-08, assigned to Mobay Corp.
  10. ↑ Orphanides, Gus G., "Process for the production of polyurethane urea elastomers", US patent 4482690, published 1984-11-13, assigned to Air Products and Chemicals Inc.
  11. ↑ Zeller, Frank, "Energy absorbing system for vehicles", CA patent 2785900, published 2018-03-06, assigned to Texas Research International Inc.
  12. ↑ Makal, Umit G.; George H. Loeber & Lalith B. Suragani Venu, "Melt processable thermoplastic polyurethane-urea elastomers", EP patent 3433294, 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" (in en). 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. doi:10.1016/j.physb.2014.11.101. ISSN 0921-4526. Bibcode: 2015PhyB..459...58A. https://ui.adsabs.harvard.edu/abs/2015PhyB..459...58A. 
  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. https://onlinelibrary.wiley.com/doi/10.1002/app.41920. 
  16. ↑ Padilla-Acevedo, Angela I.; Ludovic Valette & Michael J. Mullins et al., "Curable resin compositions", US patent 9057002, 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" (in en). Journal of Polymer Engineering 16 (1–2): 51–72. doi:10.1515/POLYENG.1996.16.1-2.51. ISSN 2191-0340. https://www.degruyter.com/document/doi/10.1515/POLYENG.1996.16.1-2.51/html. 
  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, https://arc.aiaa.org/doi/10.2514/6.2010-2814, retrieved 2022-03-24 
  19. ↑ Poynton, Gary (2014). "Multi‐component Epoxy Resin Formulation for High Temperature Applications PhD thesis". https://www.research.manchester.ac.uk/portal/files/54554454/FULL_TEXT.PDF. 
  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" (in en). https://rivercountry.newschannelnebraska.com/story/45148649/global-detda-and-dmtda-market-size-research-with-latest-opportunities-2021-top-growing-factors-market-dynamic-analysis-and-development-suggestions. 
  21. ↑ "DETDA and DMTDA Market Size, Status, Global Outlook and Forecast 2022-2026, COVID-19 Impact, Market Trends, Share, Size" (in EN-US). https://www.marketwatch.com/press-release/detda-and-dmtda-market-size-status-global-outlook-and-forecast-2022-2026-covid-19-impact-market-trends-share-size-2022-03-09. 

External websites



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