Polyetheramines

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Chemical structure of triethylene glycol diamine, one of the simplest polyetheramines Triethylene glycol diamine.svg
Chemical structure of triethylene glycol diamine, one of the simplest polyetheramines

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. [1] A key use is for curing epoxy resins.

Contents

Use as epoxy resin curatives

One of the primary uses of polyether amines is as an epoxy curing agent. [2] They are commercially available as mono, di and tri-functional. [3] Difunctional versions tend to give flexibility and thus toughness to epoxy resin systems. [4] [5] [6] Studies have been done on the cured properties of epoxy systems using different functionality polyetheramines. [7] 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. [8]

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. [9] [10] [11] [12] [13]


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<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

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In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups. The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, three and four hydroxyl groups are diols, triols, and tetrols, respectively.

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<span class="mw-page-title-main">Hexamethylenediamine</span> Chemical compound

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<span class="mw-page-title-main">Aminoethylpiperazine</span> Chemical compound

Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.

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n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

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<span class="mw-page-title-main">Isophorone diamine</span> Chemical compound

Isophorone diamine (usually shortened to IPDA) is a chemical compound and specifically a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). It is a colorless liquid. It is a precursor to polymers and coatings.

Polyurethane dispersion, or PUD, is understood to be a polyurethane polymer resin dispersed in water, rather than a solvent, although some cosolvent maybe used. Its manufacture involves the synthesis of polyurethanes having carboxylic acid functionality or nonionic hydrophiles like PEG incorporated into, or pendant from, the polymer backbone. Two component polyurethane dispersions are also available.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used, it usually describes all resins which have water as the main carrying solvent. The resin could be water-soluble, water reducible or water dispersed.

<span class="mw-page-title-main">2-Methylpentamethylenediamine</span> Chemical compound

2-Methylpentamethylenediamine is an organic compound part of the amine family with the formula H2NCH2CH2CH2CH(CH3)CCH2NCH2. A colorless liquid, this diamine is obtained by the hydrogenation of 2-methylglutaronitrile. It is better known by the trade name "Dytek A".

<span class="mw-page-title-main">Diethyl toluene diamine</span> Chemical compound

Diethyl toluene diamine (DETDA) is a liquid aromatic organic molecule 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. 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). The toxicology is reasonably well understood.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. It has the formula C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane, and the CAS number 14228-73-0. It is REACH registered in Europe. It is an industrial chemical and a key use is in the reduction of viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">Poly(propylene glycol) diglycidyl ether</span> Chemical compound

Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. They have the formula (C3H6O)n.C6H10O3 and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer. It is REACH registered.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

References

  1. ↑ "Epoxy formulations using polyetheramines" (PDF).
  2. ↑ Zhao, Heng; Xu, Shuangshuang; Guo, Anru; Li, Jie; Liu, Dong (2021-08-01). "The Curing Kinetics Analysis of Four Epoxy Resins Using a Diamine Terminated Polyether as Curing Agent". Thermochimica Acta. 702: 178987. doi:10.1016/j.tca.2021.178987. ISSN   0040-6031. S2CID   237730621.
  3. ↑ McAninch, Ian M.; Palmese, Giuseppe R.; Lenhart, Joseph L.; La Scala, John J. (2013-11-05). "Characterization of epoxies cured with bimodal blends of polyetheramines". Journal of Applied Polymer Science. 130 (3): 1621–1631. doi:10.1002/app.39322. ISSN   0021-8995.
  4. ↑ Su, Shunsheng; Wang, Haiqing; Zhou, Chuanjian; Wang, Yanxiang; Liu, Jianjun (2018-09-01). "Study on epoxy resin with high elongation-at-break using polyamide and polyether amine as a two-component curing agent". E-Polymers. 18 (5): 433–439. doi: 10.1515/epoly-2017-0252 . ISSN   1618-7229. S2CID   139697130.
  5. ↑ Abdollahi, H.; Salimi, A.; Barikani, M.; Samadi, A.; Hosseini Rad, S.; Zanjanijam, A. R. (2019-03-05). "Systematic investigation of mechanical properties and fracture toughness of epoxy networks: Role of the polyetheramine structural parameters". Journal of Applied Polymer Science. 136 (9). doi:10.1002/app.47121. ISSN   0021-8995. S2CID   139177635.
  6. ↑ Jamshidi, Hajar; Akbari, Reza; Beheshty, Mohammad Hosain (2015-05-01). "Toughening of dicyandiamide-cured DGEBA-based epoxy resins using flexible diamine". Iranian Polymer Journal. 24 (5): 399–410. doi:10.1007/s13726-015-0332-5. ISSN   1735-5265. S2CID   137162229.
  7. ↑ Wan, Jintao; Li, Cheng; Bu, Zhi-Yang; Xu, Cun-Jin; Li, Bo-Geng; Fan, Hong (2012-04-15). "A comparative study of epoxy resin cured with a linear diamine and a branched polyamine". Chemical Engineering Journal. 188: 160–172. doi:10.1016/j.cej.2012.01.134. ISSN   1385-8947.
  8. ↑ Lin, J. J.; Speranza, G. P.; Waddill, H. G. (1997-12-19). "Synthesis and reactivity of Mannich-derived polyoxyethylene amines as epoxy curing agents". Journal of Applied Polymer Science. 66 (12): 2339–2346. doi:10.1002/(SICI)1097-4628(19971219)66:12<2339::AID-APP15>3.0.CO;2-V. ISSN   0021-8995.
  9. ↑ Wang, Wenying; Wang, Wei; Zhu, Zhongpeng; Hu, Xiaoming; Qiao, Fulin; Yang, Jing; Liu, Dan; Chen, Pu; Zhang, Qundan (2023-04-15). "Quantitation of polyetheramines as the active components of detergent additives in gasoline by the ninhydrin reaction". Fuel. 338: 127275. doi:10.1016/j.fuel.2022.127275. ISSN   0016-2361.
  10. ↑ Kuo, Chung-Hao; Smocha, Ruth; Loeper, Paul; Mukkada, Nicholas; Simpson Green, Felicia (2022-08-30). "Aftermarket Fuel Additives and their Effects on GDI Injector Performance and Particulate Emissions". SAE Technical Paper Series. 400 Commonwealth Drive, Warrendale, PA, United States: SAE International. 1. doi:10.4271/2022-01-1074. S2CID   251964600.{{cite journal}}: CS1 maint: location (link)
  11. ↑ Zerda, T. W; Yuan, X; Moore, S. M (2001-08-01). "Effects of fuel additives on the microstructure of combustion engine deposits". Carbon. 39 (10): 1589–1597. doi:10.1016/S0008-6223(00)00287-6. ISSN   0008-6223.
  12. ↑ "A Brief Look at Polyetheramine - A Unique and Powerful Fuel Additive". www.irocoatingadditive.com. Retrieved 2023-11-16.
  13. ↑ Smocha, Ruth (2020-09-15). Sludge and Varnish Evaluation of Polyether Amine Gasoline Fuel Additives at "Complete Fuel System Cleaner" Aftermarket Fuel Additive Concentrations (Report). Warrendale, PA: SAE Technical Paper.
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