2,4,6-Tris(dimethylaminomethyl)phenol

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2,4,6-Tris(dimethylaminomethyl)phenol
Names
IUPAC name
2,4,6-Tris[(dimethylamino)methyl]phenol
Identifiers
3D model (JSmol)
  • CN(C)CC1=CC(=C(C(=C1)CN(C)C)O)CN(C)C
Properties
C15H27N3O
Molar mass 265.401 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,6-Tris(dimethylaminomethyl)phenol is an aromatic organic chemical that has tertiary amine and phenolic hydroxyl functionality in the same molecule.[1] The formula is C15H27N3O and the CAS Registry Number is 90-72-2. It is REACH registered and the European Community Number is 202-013-9.[2][3][4]

Uses[edit]

A key use is as a catalyst for epoxy resin chemistry. It can be used as a homopolymerization catalyst for epoxy resins and also as an accelerator with epoxy resin curing agents. It is then further used in coatings, sealants, adhesives[5] and elastomers.[6] It has been stated that it is probably the most widely used room temperature accelerator for two-component epoxy resin systems.[7][8] The kinetics of curing with and without this accelerator have been extensively studied.[9][10] It is the usual benchmark or control used when other catalysts and accelerators are being developed and tested.[11] This includes its use in composite applications.[12]

In addition to its use in epoxy chemistry, it is also used in polyurethane chemistry for example by grafting the molecule into the polymer backbone.[13] It is also used as a trimerization catalyst with polymeric MDI.[14]

Polyether ether ketones may also be grafted with the molecule which then finds use in lithium batteries.[15]

The high functionality of the molecule means it can be used to complex some transition metals and this has also been studied.[16]

Often cited weaknesses are yellowing and odor.[17]

Manufacture[edit]

The material is a Mannich base and is manufactured by reacting phenol, formaldehyde and dimethylamine in a reactor under vacuum and removing the water produced.

Toxicity[edit]

It is classed as a high volume chemical and as such, its toxicity profile has been extensively studied.[18][19][20]

Further reading[edit]

  • Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.{{cite book}}: CS1 maint: others (link)
  • Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.{{cite book}}: CS1 maint: location missing publisher (link)
  • Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.

References[edit]

  1. ^ "Human Metabolome Database: Showing metabocard for 2,4,6-Tris(dimethylaminomethyl)phenol (HMDB0247627)". hmdb.ca. Retrieved 2024-06-04.
  2. ^ PubChem. "2,4,6-Tris(dimethylaminomethyl)phenol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-06-05.
  3. ^ "Registration Dossier - ECHA". echa.europa.eu. Retrieved 2024-06-05.
  4. ^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2024-06-05.
  5. ^ Schlechte, Jay S. (2023), "Advances in epoxy adhesives", Advances in Structural Adhesive Bonding, Elsevier, pp. 3–67, doi:10.1016/b978-0-323-91214-3.00030-2, ISBN 978-0-323-91214-3, retrieved 2024-06-05
  6. ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 15 Master of Science Thesis April 1997 Imperial College London
  7. ^ Seo, Jiae; Yui, Nobuhiko; Seo, Ji-Hun (January 2019). "Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin". Chemical Engineering Journal. 356: 303–311. doi:10.1016/j.cej.2018.09.020. ISSN 1385-8947.
  8. ^ Chen, Fengjun; Liu, Fan; Du, Xiaogang (2023-01-10). "Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator". Journal of Applied Polymer Science. 140 (2). doi:10.1002/app.53302. ISSN 0021-8995.
  9. ^ Yevtushenko, G.T.; Moshinskii, L.Ya.; Beletskaya, T.V. (January 1974). "Kinetics of hardening of ED-5 epoxy resins with anhydrides in the presence of 2.4,6-Tris-(Dimethylaminomethyl)phenol". Polymer Science U.S.S.R. 16 (6): 1557–1562. doi:10.1016/0032-3950(74)90421-3. ISSN 0032-3950.
  10. ^ Hesabi, Mohammadnabi; Salimi, Ali; Beheshty, Mohammad Hosain (May 2017). "Effect of tertiary amine accelerators with different substituents on curing kinetics and reactivity of epoxy/dicyandiamide system". Polymer Testing. 59: 344–354. doi:10.1016/j.polymertesting.2017.02.023. ISSN 0142-9418.
  11. ^ Fedtke, Manfred (January 1987). "Acceleration mechanisms in curing reactions involving model systems". Makromolekulare Chemie. Macromolecular Symposia. 7 (1): 153–168. doi:10.1002/masy.19870070114. ISSN 0258-0322.
  12. ^ Niazi, Mina; Beheshty, Mohammad Hosain (2019-04-01). "A new latent accelerator and study of its effect on physical, mechanical and shelf-life of carbon fiber epoxy prepreg". Iranian Polymer Journal. 28 (4): 337–346. doi:10.1007/s13726-019-00704-8. ISSN 1735-5265.
  13. ^ Chung, Yong-Chan; Kim, Ji Young; Park, Ji Eun; Chun, Byoung Chul (2021-04-01). "Hydrophilic Modification of a Polyurethane Surface Using Grafted 2,4,6-Tris(dimethylaminomethyl) Phenol". Fibers and Polymers. 22 (4): 904–915. doi:10.1007/s12221-021-1406-y. ISSN 1875-0052.
  14. ^ Imai, Yoshio; Hidai, Takao; Inukai, Takao; Nakanishi, Takehisa (January 1986). "Study on Isocyanurate-Modified MDI. 1 — Preparation". Cellular Polymers. 5 (1): 13–23. doi:10.1177/026248938600500102. ISSN 0262-4893.
  15. ^ Kumar, Sonu; Bhushan, Mani; Shahi, Vinod K. (February 2020). "Cross-linked amphoteric membrane: Sulphonated poly(ether ether ketone) grafted with 2,4,6-tris(dimethylaminomethyl)phenol using functionalized side chain spacers for vanadium redox flow battery". Journal of Power Sources. 448: 227358. doi:10.1016/j.jpowsour.2019.227358. ISSN 0378-7753.
  16. ^ Romashkina, E. P.; Ilyukhin, A. B.; Strashnova, S. B.; Koval’chukova, O. V.; Palkina, K. K.; Sergienko, V. S.; Zaitsev, B. E. (2011-03-01). "Complex compounds of some p, d, and f metals with 2,4,6-tris(N,N-dimethylaminomethyl)phenol (HL): Crystal and molecular structure of H4L(NO3)3 · H2O and H4LCl3 · 3H2O". Russian Journal of Inorganic Chemistry. 56 (3): 350–356. doi:10.1134/S0036023611030193. ISSN 1531-8613.
  17. ^ Chiang, Tzu Hsuan; Hsieh, Tsung‐Eong (December 2007). "Effect of tertiary amines on yellowing of UV‐curable epoxide resins". Polymer International. 56 (12): 1544–1552. doi:10.1002/pi.2300. ISSN 0959-8103.
  18. ^ Kanekrva, Lasse; Estlander, Tuula; Jolanki, Riitta (December 1996). "OCCUPATIONAL ALLERGIC CONTACT DERMATITIS CAUSED BY 2,4,6‐TRIS‐(DIMETHYLAMINOMETHYL)PHENOL, AND REVIEW OF SENSITIZING EPOXY RESIN HARDENERS". International Journal of Dermatology. 35 (12): 852–856. doi:10.1111/j.1365-4362.1996.tb05050.x. ISSN 0011-9059.
  19. ^ Aalto‐Korte, Kristiina; Pesonen, Maria; Suuronen, Katri (December 2015). "Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sensitizing products, and diagnosis". Contact Dermatitis. 73 (6): 336–342. doi:10.1111/cod.12445. ISSN 0105-1873.
  20. ^ Geier, Johannes; Dickel, Heinrich; Schröder‐Kraft, Claudia; Gina, Michal; Simon, Dagmar; Weisshaar, Elke; Lang, Claudia; Brans, Richard; Bauer, Andrea; Löffler, Harald; Schubert, Steffen; for the IVDK (April 2023). "2,4, 6‐Tris (dimethylaminomethyl)phenol: The allergen which came in from the cold". Contact Dermatitis. 88 (4): 316–318. doi:10.1111/cod.14268. ISSN 0105-1873.
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