2,4,6-Tris(dimethylaminomethyl)phenol

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,{{Cite journal |last1=Niazi |first1=Mina |last2=Beheshty |first2=Mohammad Hosain |date=2019-04-01 |title=A new latent accelerator and study of its effect on physical, mechanical and shelf-life of carbon fiber epoxy prepreg |url=https://doi.org/10.1007/s13726-019-00704-8 |journal=Iranian Polymer Journal |language=en |volume=28 |issue=4 |pages=337–346 |doi=10.1007/s13726-019-00704-8 |issn=1735-5265|url-access=subscription }} adhesives{{Citation |last1=Schlechte |first1=Jay S. |title=Advances in epoxy adhesives |date=2023 |work=Advances in Structural Adhesive Bonding |pages=3–67 |url=https://doi.org/10.1016/B978-0-323-91214-3.00030-2 |access-date=2024-06-05 |publisher=Elsevier |doi=10.1016/b978-0-323-91214-3.00030-2 |isbn=978-0-323-91214-3|url-access=subscription }} and elastomers. It has been stated that it is probably the most widely used room temperature accelerator for two-component epoxy resin systems.{{Cite journal |last1=Seo |first1=Jiae |last2=Yui |first2=Nobuhiko |last3=Seo |first3=Ji-Hun |date=January 2019 |title=Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin |url=https://doi.org/10.1016/j.cej.2018.09.020 |journal=Chemical Engineering Journal |volume=356 |pages=303–311 |doi=10.1016/j.cej.2018.09.020 |bibcode=2019ChEnJ.356..303S |issn=1385-8947|url-access=subscription }}{{Cite journal |last1=Chen |first1=Fengjun |last2=Liu |first2=Fan |last3=Du |first3=Xiaogang |date=2023-01-10 |title=Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator |url=https://onlinelibrary.wiley.com/doi/10.1002/app.53302 |journal=Journal of Applied Polymer Science |language=en |volume=140 |issue=2 |doi=10.1002/app.53302 |issn=0021-8995|url-access=subscription }} The kinetics of curing with and without this accelerator have been extensively studied.{{Cite journal |last1=Yevtushenko |first1=G.T. |last2=Moshinskii |first2=L.Ya. |last3=Beletskaya |first3=T.V. |date=January 1974 |title=Kinetics of hardening of ED-5 epoxy resins with anhydrides in the presence of 2.4,6-Tris-(Dimethylaminomethyl)phenol |url=https://doi.org/10.1016/0032-3950(74)90421-3 |journal=Polymer Science U.S.S.R. |volume=16 |issue=6 |pages=1557–1562 |doi=10.1016/0032-3950(74)90421-3 |issn=0032-3950|url-access=subscription }}{{Cite journal |last1=Hesabi |first1=Mohammadnabi |last2=Salimi |first2=Ali |last3=Beheshty |first3=Mohammad Hosain |date=May 2017 |title=Effect of tertiary amine accelerators with different substituents on curing kinetics and reactivity of epoxy/dicyandiamide system |url=https://doi.org/10.1016/j.polymertesting.2017.02.023 |journal=Polymer Testing |volume=59 |pages=344–354 |doi=10.1016/j.polymertesting.2017.02.023 |issn=0142-9418|url-access=subscription }} It is the usual benchmark or control used when other catalysts and accelerators are being developed and tested.{{Cite journal |last1=Fedtke |first1=Manfred |date=January 1987 |title=Acceleration mechanisms in curing reactions involving model systems |url=https://onlinelibrary.wiley.com/doi/10.1002/masy.19870070114 |journal=Makromolekulare Chemie. Macromolecular Symposia |language=en |volume=7 |issue=1 |pages=153–168 |doi=10.1002/masy.19870070114 |issn=0258-0322|url-access=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.{{Cite journal |last1=Chung |first1=Yong-Chan |last2=Kim |first2=Ji Young |last3=Park |first3=Ji Eun |last4=Chun |first4=Byoung Chul |date=2021-04-01 |title=Hydrophilic Modification of a Polyurethane Surface Using Grafted 2,4,6-Tris(dimethylaminomethyl) Phenol |url=https://doi.org/10.1007/s12221-021-1406-y |journal=Fibers and Polymers |language=en |volume=22 |issue=4 |pages=904–915 |doi=10.1007/s12221-021-1406-y |issn=1875-0052|url-access=subscription }} It is also used as a trimerization catalyst with polymeric MDI.{{Cite journal |last1=Imai |first1=Yoshio |last2=Hidai |first2=Takao |last3=Inukai |first3=Takao |last4=Nakanishi |first4=Takehisa |date=January 1986 |title=Study on Isocyanurate-Modified MDI. 1 — Preparation |url=http://journals.sagepub.com/doi/10.1177/026248938600500102 |journal=Cellular Polymers |language=en |volume=5 |issue=1 |pages=13–23 |doi=10.1177/026248938600500102 |issn=0262-4893|url-access=subscription }}

Polyether ether ketones may also be grafted with the molecule which then finds use in lithium batteries.{{Cite journal |last1=Kumar |first1=Sonu |last2=Bhushan |first2=Mani |last3=Shahi |first3=Vinod K. |date=February 2020 |title=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 |url=https://doi.org/10.1016/j.jpowsour.2019.227358 |journal=Journal of Power Sources |volume=448 |pages=227358 |doi=10.1016/j.jpowsour.2019.227358 |bibcode=2020JPS...44827358K |issn=0378-7753|url-access=subscription }}

The high functionality of the molecule means it can be used to complex some transition metals and this has also been studied.{{Cite journal |last1=Romashkina |first1=E. P. |last2=Ilyukhin |first2=A. B. |last3=Strashnova |first3=S. B. |last4=Koval’chukova |first4=O. V. |last5=Palkina |first5=K. K. |last6=Sergienko |first6=V. S. |last7=Zaitsev |first7=B. E. |date=2011-03-01 |title=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 |url=https://doi.org/10.1134/S0036023611030193 |journal=Russian Journal of Inorganic Chemistry |language=en |volume=56 |issue=3 |pages=350–356 |doi=10.1134/S0036023611030193 |issn=1531-8613|url-access=subscription }}

Often cited weaknesses are yellowing and odor.{{Cite journal |last1=Chiang |first1=Tzu Hsuan |last2=Hsieh |first2=Tsung-Eong |date=December 2007 |title=Effect of tertiary amines on yellowing of UV-curable epoxide resins |url=https://onlinelibrary.wiley.com/doi/10.1002/pi.2300 |journal=Polymer International |language=en |volume=56 |issue=12 |pages=1544–1552 |doi=10.1002/pi.2300 |issn=0959-8103|url-access=subscription }}

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.

It is classed as a high volume chemical and as such, its toxicity profile has been extensively studied.{{Cite journal |last1=Kanekrva |first1=Lasse |last2=Estlander |first2=Tuula |last3=Jolanki |first3=Riitta |date=December 1996|title=OCCUPATIONAL ALLERGIC CONTACT DERMATITIS CAUSED BY 2,4,6-TRIS-(DIMETHYLAMINOMETHYL)PHENOL, AND REVIEW OF SENSITIZING EPOXY RESIN HARDENERS |url=https://onlinelibrary.wiley.com/doi/10.1111/j.1365-4362.1996.tb05050.x |journal=International Journal of Dermatology |language=en |volume=35 |issue=12 |pages=852–856 |doi=10.1111/j.1365-4362.1996.tb05050.x |pmid=8970840 |issn=0011-9059|url-access=subscription }}{{Cite journal |last1=Aalto-Korte |first1=Kristiina |last2=Pesonen |first2=Maria |last3=Suuronen |first3=Katri |date=December 2015 |title=Occupational allergic contact dermatitis caused by epoxy chemicals: occupations, sensitizing products, and diagnosis |url=https://onlinelibrary.wiley.com/doi/10.1111/cod.12445 |journal=Contact Dermatitis |language=en |volume=73 |issue=6 |pages=336–342 |doi=10.1111/cod.12445 |pmid=26230376 |issn=0105-1873|url-access=subscription }}{{Cite journal |last1=Geier |first1=Johannes |last2=Dickel |first2=Heinrich |last3=Schröder-Kraft |first3=Claudia |last4=Gina |first4=Michal |last5=Simon |first5=Dagmar |last6=Weisshaar |first6=Elke |last7=Lang |first7=Claudia |last8=Brans |first8=Richard |last9=Bauer |first9=Andrea |last10=Löffler |first10=Harald |last11=Schubert |first11=Steffen |last12=for the IVDK |date=April 2023 |title=2,4, 6-Tris (dimethylaminomethyl)phenol: The allergen which came in from the cold |url=https://onlinelibrary.wiley.com/doi/10.1111/cod.14268 |journal=Contact Dermatitis |language=en |volume=88 |issue=4 |pages=316–318 |doi=10.1111/cod.14268 |pmid=36524787 |issn=0105-1873|doi-access=free }}

• {{Cite book|url=https://www.worldcat.org/oclc/182890|title=Epoxy resin technology.|date=1968|publisher=Interscience Publishers|author=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}}
• {{Cite book|last=Lee|first=Henry|url=https://www.worldcat.org/oclc/311631322|title=Handbook of epoxy resins|date=1967|publisher=McGraw-Hill|others=Kris Neville|isbn=0-07-036997-6|edition=[2nd, expanded work]|location=New York|oclc=311631322}}

{{DEFAULTSORT:Tris(dimethylaminomethyl)phenol, 2, 4, 6-}}

Category:Tertiary amines

Category:Phenols

Category:Catalysts

Category:Dimethylamino compounds