2,4,6-Tris(dimethylaminomethyl)phenol

Aromatic organic chemical 2,4,6-Tris(dimethylaminomethyl)phenol.svg 180px 2,4,6-Tris[(dimethylamino)methyl]phenol 90-72-2 correct CAS 1887090 6759 202-013-9 7026 2AGN35QF4W 2735 1S/C15H27N3O/c1-16(2)9-12-7-13(10-17(3)4)15(19)14(8-12)11-18(5)6/h7-8,19H,9-11H2,1-6H3 AHDSRXYHVZECER-UHFFFAOYSA-N CN(C)CC1=CC(=C(C(=C1)CN(C)C)O)CN(C)C 15 27 3 1 0.974 at 15°C 05 07 Danger 302 315 319 260 261 264 264+265 270 272 273 280 301+317 301+330+331 302+352 302+361+354 304+340 305+351+338 305+354+338 316 317 321 330 332+317 333+317 337+317 362+364 363 405 501 2,4,6-Tris(dimethylaminomethyl)phenol is an aromatic organic chemical that has tertiary amine and phenolic hydroxyl functionality in the same molecule.Human Metabolome Database: Showing metabocard for 2,4,6-Tris(dimethylaminomethyl)phenol (HMDB0247627) https://hmdb.ca/metabolites/HMDB0247627 2024-06-04 hmdb.ca 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.PubChem 2,4,6-Tris(dimethylaminomethyl)phenol https://pubchem.ncbi.nlm.nih.gov/compound/7026 2024-06-05 pubchem.ncbi.nlm.nih.gov enRegistration Dossier - ECHA https://echa.europa.eu/registration-dossier/-/registered-dossier/13928 2024-06-05 echa.europa.eu en-GBCAS Common Chemistry https://commonchemistry.cas.org/detail?cas_rn=90-72-2 2024-06-05 commonchemistry.cas.org Uses 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,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 sealants, composites,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 https://doi.org/10.1007/s13726-019-00704-8 Iranian Polymer Journal en 28 4 337–346 10.1007/s13726-019-00704-8 1735-5265 subscription adhesivesSchlechte Jay S. Advances in epoxy adhesives 2023 Advances in Structural Adhesive Bonding 3–67 https://doi.org/10.1016/B978-0-323-91214-3.00030-2 2024-06-05 Elsevier 10.1016/b978-0-323-91214-3.00030-2 978-0-323-91214-3 subscription and elastomers. It has been stated that it is probably the most widely used room temperature accelerator for two-component epoxy resin systems.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 https://doi.org/10.1016/j.cej.2018.09.020 Chemical Engineering Journal 356 303–311 10.1016/j.cej.2018.09.020 2019ChEnJ.356..303S 1385-8947 subscription Chen Fengjun Liu Fan Du Xiaogang 2023-01-10 Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator https://onlinelibrary.wiley.com/doi/10.1002/app.53302 Journal of Applied Polymer Science en 140 2 10.1002/app.53302 0021-8995 subscription The kinetics of curing with and without this accelerator have been extensively studied.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 https://doi.org/10.1016/0032-3950(74)90421-3 Polymer Science U.S.S.R. 16 6 1557–1562 10.1016/0032-3950(74)90421-3 0032-3950 subscription 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 https://doi.org/10.1016/j.polymertesting.2017.02.023 Polymer Testing 59 344–354 10.1016/j.polymertesting.2017.02.023 0142-9418 subscription It is the usual benchmark or control used when other catalysts and accelerators are being developed and tested.Fedtke Manfred January 1987 Acceleration mechanisms in curing reactions involving model systems https://onlinelibrary.wiley.com/doi/10.1002/masy.19870070114 Makromolekulare Chemie. Macromolecular Symposia en 7 1 153–168 10.1002/masy.19870070114 0258-0322 subscription 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.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 https://doi.org/10.1007/s12221-021-1406-y Fibers and Polymers en 22 4 904–915 10.1007/s12221-021-1406-y 1875-0052 subscription It is also used as a trimerization catalyst with polymeric MDI.Imai Yoshio Hidai Takao Inukai Takao Nakanishi Takehisa January 1986 Study on Isocyanurate-Modified MDI. 1 — Preparation http://journals.sagepub.com/doi/10.1177/026248938600500102 Cellular Polymers en 5 1 13–23 10.1177/026248938600500102 0262-4893 subscription Polyether ether ketones may also be grafted with the molecule which then finds use in lithium batteries.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 https://doi.org/10.1016/j.jpowsour.2019.227358 Journal of Power Sources 448 227358 10.1016/j.jpowsour.2019.227358 2020JPS...44827358K 0378-7753 subscription The high functionality of the molecule means it can be used to complex some transition metals and this has also been studied.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 https://doi.org/10.1134/S0036023611030193 Russian Journal of Inorganic Chemistry en 56 3 350–356 10.1134/S0036023611030193 1531-8613 subscription Often cited weaknesses are yellowing and odor.Chiang Tzu Hsuan Hsieh Tsung-Eong December 2007 Effect of tertiary amines on yellowing of UV-curable epoxide resins https://onlinelibrary.wiley.com/doi/10.1002/pi.2300 Polymer International en 56 12 1544–1552 10.1002/pi.2300 0959-8103 subscription Manufacture 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 It is classed as a high volume chemical and as such, its toxicity profile has been extensively studied.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 https://onlinelibrary.wiley.com/doi/10.1111/j.1365-4362.1996.tb05050.x International Journal of Dermatology en 35 12 852–856 10.1111/j.1365-4362.1996.tb05050.x 8970840 0011-9059 subscription Aalto-Korte Kristiina Pesonen Maria Suuronen Katri December 2015 Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sensitizing products, and diagnosis https://onlinelibrary.wiley.com/doi/10.1111/cod.12445 Contact Dermatitis en 73 6 336–342 10.1111/cod.12445 26230376 0105-1873 subscription 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 en 88 4 316–318 10.1111/cod.14268 36524787 0105-1873 free References Further reading Epoxy resin technology. 1968 Interscience Publishers Paul F. Bruins, Polytechnic Institute of Brooklyn 0-470-11390-1 New York 182890 Flick Ernest W. Epoxy resins, curing agents, compounds, and modifiers : an industrial guide 1993 978-0-8155-1708-5 Park Ridge, NJ 915134542 Lee Henry Handbook of epoxy resins 1967 McGraw-Hill Kris Neville 0-07-036997-6 [2nd, expanded work] New York 311631322 Category:Tertiary amines Category:Phenols Category:Catalysts Category:Dimethylamino compounds