Diethylenetriamine

Diethylenetriamine is a colorless liquid, completely miscible with water and many organic solvents. It is a solvent for sulfur, ocid goses, numerous naturol resins ond dyes. It Is also used in organic synthesis ond as a saponification agent for acidic materiols. 

Tetraethyienepentamine is a viscooS/ hygroscopic and high-boiling liquid. It is miscible with water and many arganic solvents, and is o solvent for dyes, resins, sulfur, and acid gases. It also forms soaps with fatty acids and it is employed in the synthesis of emulsifiers, plastics, and in rubber reclaiming. 

Propyienediamine is a water-while liquid with on ammaniocal odor. It is miscible with water and mony organic solvents, among them being benzene ond nophtha. It does not form a constant-bailing mixture with woter. It is a solvent for such substances as cellulose nitrate, castor ail, shellac, pine oil, copal gum, rosin, and dyes. 

It behaves much like ethylenediamine but it is considered superior in solvent power. 

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The two-part epoxy adhesive, readily available in hardware stores or other consumer outlets, comes in two tubes. One tube contains the epoxy resin, the other contains an amine hardener. Common diamine room temperature epoxy curing agents are materials such as the polyamides, available under the trade name Versamid. These polyamides are the reaction products of dimer acids and aUphatic diamines such as diethylenetriamine [111-40-0] ... 

Polyamines, such as diethylenetriamine [111 0-0] are used at times ia the syathesis of microporous weak base resias to achieve significantly higher capacity. However, these resias geaerally have lower physical and chemical stabiHty than resias prepared from primary or secoadary amines. 

Process Raw Material. Industrial solvents are raw materials in some production processes. Eor example, only a small proportion of acetone is used as a solvent, most is used in producing methyl methacrylate and bisphenol A. Alcohols are used in the manufacture of esters and glycol ethers. Diethylenetriamine is also used in the manufacture of curing agents for epoxy resins. Traditionally, chlorinated hydrocarbon solvents have been the starting materials for duorinated hydrocarbon production. 

Eig. 1. Types of chelates where (1) represents a tetracoordinate metal having the bidentate chelant ethylenediamine and monodentate water (2), a hexacoordinate metal bound to two diethylenetriamines, tridentate chelants (3), a hexacoordinate metal having triethylenetetramine, a tetradentate chelant, and monodentate water and (4), a porphine chelate. The dashed lines iadicate coordinate bonds. 

Reactive Polyamide Resins. Another significant commercial appHcation of dimer acids is in reactive polyamide resins. These are formed by the reaction of dimer acids with polyamines such as diethylenetriamine to form polyamides containing reactive secondary amine groups (see DiAMlNES AND HIGHER AMINES, aliphatic). In contrast to nonreactive polyamides, these materials are generally Hquids at 25°C. 

Comparisons of the properties of solvent-free Hquid coatings based on unmodified bisphenol A epoxies cured with varying amine hardeners are shown in Table 6. Examples include diethylenetriamine [111-40-0] H2NC2H4NHC2H4NH2 (7), triethylenetetramine [112-24-3] ... 

It is thus seen that as a class the primarily aliphatic amines provide fast-curing hardeners for use at room temperatures. With certain exceptions they are skin sensitisers. The chemical resistance of the hardened resins varies according to the hardener used but in the case of the unmodified amines is quite good. The hardened resins have quite low heat distortion temperatures and except with diethylenetriamine seldom exceed 100°C. The number of variations in the properties obtainable may be increased by using blends of hardeners. 

Many other amines are catalytic in their action. One of these, piperidine, has been in use since the early patents of Castan. 5-7 pts phr of piperidine are used to give a system with a pot life of about eight hours. A typical cure schedule is three hours at 100°C. Although it is a skin irritant it is still used for casting of larger masses than are possible with diethylenetriamine and diethylaminopropylamine. 

Interesting amine flexibilisers have also been described. These materials are made by cyanoethylation of amine hardeners such as diethylenetriamine, to such an extent that only two reactive hydrogens remain and the material is only difunctional, e.g. Figure 26.21. 

Epichlorohydrin with bisphenol A. The curing agents may pose significant health hazards, e.g. amines (triethylamine, p-phenylenediamine, diethylenetriamine) or acid anhydrides (pyromellitic dianhydride)... 

Diethylene glycol Diethylene glycol ether Di-(2 ethyl hexyl) phthalate Diethylenetriamine Difluorodibromomethane Difluorodichloromethane Diglycidyl ether of Bisphenol A Dihydrocapsaicin... 

This may be crystallized from aqueous solution and, by the addition of diethylenetriamine, (H3dien)2[M07O24].4H2O has been obtained as two distinct polymorphs. Both contain discrete [Mo7024] ions but differ in the way these are packed in the crystals. 

Figure 3.33 The structure of complexes of tridentate amines such as diethylenetriamine.

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