Fatty diamines

Chem. Descrip. Diamine fatty acid condensate ionic Nature Cationic Uses Softener for textile finishing Properties Paste Michelene15 [M. Michel ]... 

Dimer diamine (- fatty amines) is produced from the acid. 

Primary amines, diamines, - fatty amine ethoxy-lates and - quaternary ammonium compounds are used as emulsifiers in bituminous emulsions used in road coverings (7% of total amine market) 0.5-1% are added to form the asphalt emulsion, which is broken in contact with the negatively charged aggregate and simultanously improves adhesion to it. 

Collectors can be further divided into two categories. Cationic collectors, used for such minerals as iron ore, silicates and potash are based on - fatty amines, fatty diamines, fatty ether amines and diamines, - quaternary ammonium compounds, ester quats and diamines. 

In the area of moleculady designed hot-melt adhesives, the most widely used resins are the polyamides (qv), formed upon reaction of a diamine and a dimer acid. Dimer acids (qv) are obtained from the Diels-Alder reaction of unsaturated fatty acids. Linoleic acid is an example. Judicious selection of diamine and diacid leads to a wide range of adhesive properties. Typical shear characteristics are in the range of thousands of kilopascals and are dependent upon temperature. Although hot-melt adhesives normally become quite brittle below the glass-transition temperature, these materials can often attain physical properties that approach those of a stmctural adhesive. These properties severely degrade as the material becomes Hquid above the melt temperature. 

Bisamides. Methylenebisamides are prepared by the reaction of the primary fatty amide and formaldehyde in the presence of an acid catalyst. AijAT-Methylenebisoleamide has been made via this route without the use of refluxing solvent (55). Polymethylenebisamides can be made from fatty acid, esters, or acid haUdes with diamines while producing water, alcohol, or mineral acid by-products. Eatty acids and diamines, typically ethylenediamine, have been condensed in the presence of NaBH and NaH2P02 to yield bisamides (56). When stearic acid, ethylenediamine, and methyl acetate react for 6 h at... 

Gyanoethylation. The reaction of primary fatty amines with acrylonitrile followed by hydrogenation produces diamines and ttiamines (4,7,31,32,37,38). 

Skin and Eye Irritation. Fatty alkylamines are generally considered to be irritating to both the skin and eyes (83). The severity or degree of irritation is usually dependent on the type of alkylamine, concentration of the chemical, time of exposure to the chemical, and sensitivity to the chemical. A small percentage of the population who come into contact with fatty amines may develop a skin hypersensitivity to certain amines and diamines. 

Alkylamines and diamines are generally classified as corrosive to the skin based on results from laboratory animal (rabbit) studies performed in accordance with the Department of Transportation (DOT) test method (84) rabbits are considered to be especially sensitive to alkylamines which even at low concentrations can induce skin redness and swelling. Oleylamine has been shown to induce mild to moderate skin irritation in laboratory rats when appHed at a concentration of 0.3% in mineral oil (Chemical Manufacturer s Association, 1985). Fatty amines which contain alkyl chains of 10—14 carbons are considered more irritating than related products which contain alkyl chains of 14—18 carbon atoms. Ethoxylation generally decreases the irritation potential of alkylamines. 

Mdogen Fatty Mmines, Diamines QNMmides, Product Bulletin, Sherex Chemical Company, Inc., DubUn, Ohio, 1989. 

Castor esters have been found to be nonirritating and noncomedogenic to the skin. Cetyl ricinoleate was found to be an effective noncomedogenic moisturizer (118). Castor-based quaternaries prepared by reaction of a castor fatty acid and a tertiary diamine are used for hair care. The ricinoleic quaternium is incorporated into clear shampoo formulations for foam enhancement and conditioning (119,120). 

Polyamide Resins. Another class of polyamide resins, in addition to the Hquid resins used as epoxy hardeners, are the thermoplastic type, prepared generaHy by the condensation reaction of polyamines with polybasic fatty acids. These resins find use in certain hot-melt adhesives, coatings, and inks. Diamines, typicaHy EDA (233), are the principal amine reactant however, tri- and tetramines are sometimes used at low levels to achieve specific performance. 

Most of the inhibitors in use are organic nitrogen compounds and these have been classified by Bregman as (a) aliphatic fatty acid derivatives, b) imidazolines, (c) quaternaries, (d) rosin derivatives (complex amine mixtures based on abietic acid) all of these will tend to have long-chain hydrocarbons, e.g. CigH, as part of the structure, (e) petroleum sulphonic acid salts of long-chain diamines (preferred to the diamines), (/) other salts of diamines and (g) fatty amides of aliphatic diamines. Actual compounds in use in classes (a) to d) include oleic and naphthenic acid salts of n-tallowpropylenediamine diamines RNH(CH2) NH2 in which R is a carbon chain of 8-22 atoms and x = 2-10 and reaction products of diamines with acids from the partial oxidation of liquid hydrocarbons. Attention has also been drawn to polyethoxylated compounds in which the water solubility can be controlled by the amount of ethylene oxide added to the molecule. 

Because of their surfactant and filming properties fatty amines such as coco-alkylamine acetate (and more especially diamines, such as tallow propylenediamine) are also occasionally employed in other types of water treatment programs. For example, they may be used as corrosion inhibitors for steel cooling systems, especially those smaller units where minimal operational control is provided. The amines must be continuously dosed to ensure good film formation (and thus corrosion protection), typically at 5 to 10 ppm active amine. They also tend to have good biostatic control properties, which provide a benefit of algal and bacterial control at no extra cost. 

The MFAs on heating (during the vulcanization process) decompose into two constituents— the diamine part functions as an accelerator while the fatty acid part acts as a flow promoter-cum-lubricant. 

Fatty acid amides of isophorone diamine, 2,5-diaminonorbomylene, and 2,2,4-trimethyl-1,6-diaminohexane are particularly suitable for high-tempera-ture and high-pressure applications [971],... 

Quatemized imidazolines with an amido moiety are suitable formulations for general oil and gas field applications. The synthesis of such compounds is detailed in the literature [1218]. For aqueous systems that contain sulfide compounds, a mixture has been described [262] that consists of an aqueous solution of an alcohol such as diethylene glycol monobutyl ether, butyl cellosolve, additional orthophosphoric acid, a fatty acid (from tall oil), substituted imidazoline, an ethoxylated fatty diamine (polyamines such as ethylenediamine, diethylenetriamine, etc.), and a molybdate compound. 

Polyesters may be used [27-30,223] instead of a fatty acid modifier for imidazoline. Thus a corrosion inhibitor with film-forming and film-persistency characteristics can be produced by first reacting, in a condensation reaction, a polybasic acid with a polyalcohol to form a partial ester. The partial ester is reacted with imidazoline or fatty diamines to result in a salt of the ester. Oil-soluble, highly water-dispersible corrosion inhibitor or oil-dispersible. 

H. Wirtz, H. Hoffmann, W. Ritschel, M. Hofinger, M. Mitzlafif, and D. Wolter. Optionally quatemized fatty esters of alkoxylated alkyl-alkylene diamines (Gegebenenfalls quatemierte Fettsaureester von oxyalkylierten Alkyl-Alkylendiaminen). Patent EP 320769, 1989. 

FAME Fatty acid methyl esters phenylene diamine... 

Albone, E.S. and Perry, G.C. (1975) Anal sac secretion of the red fox, Vulpes vulpes volatile fatty acids and diamines Implications for a fermentation hypothesis of chemical recognition. J. Chem. Ecol. 2, 101-111. 

C. W. Glankler, J. Am. Oil Chem. Soc. 56, 802A-805A (1979) . .Nitrogen Derivatives of Fatty Acids, Secondary and Tertiary Amines, Quaternary Salts, Diamines, Imidazolines". 

ASTM D 2073-92, Standard Test Methods for Total, Primary, Secondary, and Tertiary Amine Values of Fatty Amines, Amidoamines and Diamines by Referee Poten-tiometric Method, ASTM, Philadelphia, PA, 1992. 

Fabric softeners - [ALKANOLAMOSIES - ALKANOLAMINES FROM OLEFIN OXIDES AND AMMONIA] (Vol 2) - [AMINES - FATTY AMINES] (Vol 2) - [SUGARALCOHOLS] (Vol 23) -from polyamines [DIAMINES AND HIGHER AMINES ALIPHATIC] (Vol 8)... 

The mechanochemical polycondensation reaction has been studied using heterochain polymer systems—polyethylene terephthalate poly-(e-caprolactam), cellulose, etc.—characterized by end groups that can be activated to increase their own number by mechanochemical destruction of corresponding polymers. The mechanochemical destruction was done in the presence of some suitable condensing agents, such as aliphatic and aromatic diamines and fatty acid dichlorides. 

Formulations containing fatty amines and, more especially, diamines are occasionally used in cooling systems as corrosion inhibitors for steel. These are film-forming inhibitors, and they require continuous dosing for good corrosion protection, at typically 5 to 10 ppm active ingredient. 

These fatty acids and oils, as well as their derivatives, are applied in a broad range of products such as surfactants, lubricants and coatings, and, obviously, biodiesel. Upon epoxidation of the double bonds of the unsaturated fatty acids, very important compounds for the polymer industry are produced, which are used as plasticizers and stabilizers for a broad range of polymers such as polyvinyl chloride (PVC), polyesters, and polyurethanes [71]. Another interesting application has been found in the conversion of epoxidized soybean oil to carbonated soybean oil that can be reacted with ethylene diamine to obtain a polyurethane with interesting properties [72], Traditionally, stoichiometric reagents are used for the epoxidation of these oils and fats, albeit in some cases, with limited results. Therefore, the MTO/H2O2 system has been explored to epoxidize unsaturated fatty acids and oils. 

Catalytic hydrogenation of nitriles has long been used for the preparation of various amines. It is performed over metallic catalysts mostly in the liquid phase. The method is also of industrial importance and has been applied to the commercial production of various amines, for example, various aliphatic amines from fatty acid nitriles, hexa-methylenediamine (1,6-hexanediamine) from adiponitrile, and xylene-a,a -diamines [bis(aminomethyl)benzenes] from the corresponding phthalonitriles. 

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