Polyetheramines
File:Triethylene glycol diamine.svg
Polyetheramines are a group of chemicals that are aliphatic organic species based on both ether and amine groups. They are produced by reacting either ethylene oxide or propylene oxide with polyols and then aminating them. There are a number of commercially available molecules with different CAS numbers and molecular weights. They often come with a prefix of M, D or T for monofunctional, difunctional and trifunctional respectively. D-230 would mean difunctional with a molecular weight of 230.{{Cite web |title=Epoxy formulations using polyetheramines |url=https://polymerinnovationblog.com/wp-content/uploads/2020/08/Huntsman-epoxy_formulations_using_jeffamine_polyetheramines.pdf}} A key use is for curing epoxy resins.
Use as epoxy resin curatives
One of the primary uses of polyether amines is as an epoxy curing agent.{{Cite journal |last1=Zhao |first1=Heng |last2=Xu |first2=Shuangshuang |last3=Guo |first3=Anru |last4=Li |first4=Jie |last5=Liu |first5=Dong |date=2021-08-01 |title=The Curing Kinetics Analysis of Four Epoxy Resins Using a Diamine Terminated Polyether as Curing Agent |url=https://www.sciencedirect.com/science/article/pii/S0040603121001283 |journal=Thermochimica Acta |volume=702 |pages=178987 |doi=10.1016/j.tca.2021.178987 |s2cid=237730621 |issn=0040-6031|url-access=subscription }} They are commercially available as mono, di and tri-functional.{{Cite journal |last1=McAninch |first1=Ian M. |last2=Palmese |first2=Giuseppe R. |last3=Lenhart |first3=Joseph L. |last4=La Scala |first4=John J. |date=2013-11-05 |title=Characterization of epoxies cured with bimodal blends of polyetheramines |url=https://onlinelibrary.wiley.com/doi/10.1002/app.39322 |journal=Journal of Applied Polymer Science |language=en |volume=130 |issue=3 |pages=1621–1631 |doi=10.1002/app.39322 |issn=0021-8995|url-access=subscription }} Difunctional versions tend to give flexibility and thus toughness to epoxy resin systems.{{Cite journal |last1=Su |first1=Shunsheng |last2=Wang |first2=Haiqing |last3=Zhou |first3=Chuanjian |last4=Wang |first4=Yanxiang |last5=Liu |first5=Jianjun |date=2018-09-01 |title=Study on epoxy resin with high elongation-at-break using polyamide and polyether amine as a two-component curing agent |url=https://www.degruyter.com/document/doi/10.1515/epoly-2017-0252/html |journal=E-Polymers |language=en |volume=18 |issue=5 |pages=433–439 |doi=10.1515/epoly-2017-0252 |s2cid=139697130 |issn=1618-7229|doi-access=free }}{{Cite journal |last1=Abdollahi |first1=H. |last2=Salimi |first2=A. |last3=Barikani |first3=M. |last4=Samadi |first4=A. |last5=Hosseini Rad |first5=S. |last6=Zanjanijam |first6=A. R. |date=2019-03-05 |title=Systematic investigation of mechanical properties and fracture toughness of epoxy networks: Role of the polyetheramine structural parameters |url=https://onlinelibrary.wiley.com/doi/10.1002/app.47121 |journal=Journal of Applied Polymer Science |language=en |volume=136 |issue=9 |doi=10.1002/app.47121 |s2cid=139177635 |issn=0021-8995|url-access=subscription }}{{Cite journal |last1=Jamshidi |first1=Hajar |last2=Akbari |first2=Reza |last3=Beheshty |first3=Mohammad Hosain |date=2015-05-01 |title=Toughening of dicyandiamide-cured DGEBA-based epoxy resins using flexible diamine |url=https://doi.org/10.1007/s13726-015-0332-5 |journal=Iranian Polymer Journal |language=en |volume=24 |issue=5 |pages=399–410 |doi=10.1007/s13726-015-0332-5 |s2cid=137162229 |issn=1735-5265|url-access=subscription }} Studies have been done on the cured properties of epoxy systems using different functionality polyetheramines.{{Cite journal |last1=Wan |first1=Jintao |last2=Li |first2=Cheng |last3=Bu |first3=Zhi-Yang |last4=Xu |first4=Cun-Jin |last5=Li |first5=Bo-Geng |last6=Fan |first6=Hong |date=2012-04-15 |title=A comparative study of epoxy resin cured with a linear diamine and a branched polyamine |url=https://www.sciencedirect.com/science/article/pii/S1385894712001763 |journal=Chemical Engineering Journal |volume=188 |pages=160–172 |doi=10.1016/j.cej.2012.01.134 |issn=1385-8947|url-access=subscription }} As epoxy curatives, they may then be further formulated into CASE applications: coatings, adhesives, sealants, and elastomers.
A key component of a Mannich base apart from formaldehyde and a phenolic species, is an amine. Polyetheramines can undergo the Mannich reaction and thus may be used to make Mannich bases.{{Cite journal |last1=Lin |first1=J. J. |last2=Speranza |first2=G. P. |last3=Waddill |first3=H. G. |date=1997-12-19 |title=Synthesis and reactivity of Mannich-derived polyoxyethylene amines as epoxy curing agents |url=https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1097-4628(19971219)66:123.0.CO;2-V |journal=Journal of Applied Polymer Science |language=en |volume=66 |issue=12 |pages=2339–2346 |doi=10.1002/(SICI)1097-4628(19971219)66:12<2339::AID-APP15>3.0.CO;2-V |issn=0021-8995|url-access=subscription }}
Use as a fuel additive
Sludge and other deposits build up in internal combustion engines especially gasoline powered versions. Fuel additives and detergents are thus often employed to help remove these or at least minimize them. Polyetheramines are one such additive.{{Cite journal |last1=Wang |first1=Wenying |last2=Wang |first2=Wei |last3=Zhu |first3=Zhongpeng |last4=Hu |first4=Xiaoming |last5=Qiao |first5=Fulin |last6=Yang |first6=Jing |last7=Liu |first7=Dan |last8=Chen |first8=Pu |last9=Zhang |first9=Qundan |date=2023-04-15 |title=Quantitation of polyetheramines as the active components of detergent additives in gasoline by the ninhydrin reaction |url=https://www.sciencedirect.com/science/article/pii/S0016236122040996 |journal=Fuel |volume=338 |pages=127275 |doi=10.1016/j.fuel.2022.127275 |issn=0016-2361|url-access=subscription }}{{Cite journal |last1=Kuo |first1=Chung-Hao |last2=Smocha |first2=Ruth |last3=Loeper |first3=Paul |last4=Mukkada |first4=Nicholas |last5=Simpson Green |first5=Felicia |date=2022-08-30 |title=Aftermarket Fuel Additives and their Effects on GDI Injector Performance and Particulate Emissions |url=https://doi.org/10.4271/2022-01-1074 |journal=SAE Technical Paper Series |volume=1 |language=en |location=400 Commonwealth Drive, Warrendale, PA, United States |publisher=SAE International |doi=10.4271/2022-01-1074|s2cid=251964600 |url-access=subscription }}{{Cite journal |last1=Zerda |first1=T. W |last2=Yuan |first2=X |last3=Moore |first3=S. M |date=2001-08-01 |title=Effects of fuel additives on the microstructure of combustion engine deposits |url=https://www.sciencedirect.com/science/article/pii/S0008622300002876 |journal=Carbon |volume=39 |issue=10 |pages=1589–1597 |doi=10.1016/S0008-6223(00)00287-6 |issn=0008-6223|url-access=subscription }}{{Cite web |title=A Brief Look at Polyetheramine - A Unique and Powerful Fuel Additive |url=https://www.irocoatingadditive.com/polyetheramine/a-brief-look-at-polyetheramine-a-unique-and-powerful-fuel-additive.html |access-date=2023-11-16 |website=www.irocoatingadditive.com}}{{Cite report |url=https://www.sae.org/publications/technical-papers/content/2020-01-2100/ |title=Sludge and Varnish Evaluation of Polyether Amine Gasoline Fuel Additives at "Complete Fuel System Cleaner" Aftermarket Fuel Additive Concentrations |last=Smocha |first=Ruth |date=2020-09-15 |publisher=SAE Technical Paper |issue=2020–01–2100 |location=Warrendale, PA |language=English}}