Alkanolamides fatty

Alkanolamides are produced by condensation of fatty esters or acids with an alkanolamine. The monoalkanolamides account for 30% of market while diethanolamides account for the bulk of the rest with the balance being made up of a few specialised materials. 

The monoethanolamides are not soluble in water and are hard waxy solids, which render them useful in laundry detergent powders since they give easier flowing powders than the sticky diethanolamides and improve the foam and foam stability properties. The simple chemistry is given below  

The simplest method of preparation involves heating equimolar quantities of acid and the monoalkanolamine and distilling off the water. However there are competing reactions [34, 35] leading to several potential co-products  

These are minimised by avoiding excess acid and a longer reaction time with cook down temperature of typically 150°C. 

Preparation from the methyl ester rather than free acid gives a product with much less of the unwanted side products. Commercial grades of monoethanolamides are relatively complex mixtures and with 60 trade names there is likely to be variation in properties depending on the exact manufacturing procedures employed. The dialkanolamides are prepared by similar chemistry which seems even more complicated  

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Alcohol ether sulfates are used in mixture with sulfonates, either alkyl-benzenesulfonates or a-olefinsulfonates, and other surfactants, such as fatty alkanolamides, in manual liquid dishwashing detergents and light-duty detergents. These combinations show the excellent emulsifying and foaming properties required in dishwashing. 

Alkanolamides are nonionic surface active agents that hnd application in a multitude of uses. There are four major groups of fatty alkanolamides (1) mono-ethanolamides (MEA), (2) diethanolamides (DEA), (3) monoisopropanolamides (MIPA), and (4) ethoxylated or PEG alkanolamides. Each group has its own specific functions and uses in formulations. 

Fatty alkanolamides are mainly used as foam stabilizers, but they can also have a large effect on the viscosity of an LDLD formulation, usually increasing it. Other viscosity modifiers include hydrotropes such as alcohol, SXS, SCS, urea, and water-soluble polymers. However, not all of these have the same magnitude of effect, which depends on the surfactant system in the product. 

Fatty alkanolamides are another class of commonly employed nonionic surfactants. These are used in shampoos to enhance lather and viscosity. The most frequently used alkanolamides are cocoamide DEA (diethanolamide) and... 

An important reason besides cleaning for using combinations of primary and secondary surfactants is to improve the quality and volume of foam. As discussed in Section II.A.2, some secondary surfactants such as betaines, amine oxides, and fatty alkanolamides also act as foam modifiers. They change the foams from a loose lacy structure generated by lauryl and laureth sulfates to rich and creamy foams. 

Condensate 6117,7S09, CC. [Manufacturers Chems.] Fatty alkanolamides emulsifier, dei ent, wetting agent, dye assistant... 

Emid . [Henkel/Emery Henkel/Cospha] Fatty alkanolamides foam boostei/sta-bilizer, thickener, emulsifier for shampoos, detergents, textiles. 

Progasol . [Rhone-Poulenc/Textile Rubber] Fatty alkanolamide or sulfonate wetting, leveling, and scouring agent, emulsifier f(v textiles, detergents. 

MAJOR USES Used in the production process of lubricants for textiles, organic synthesis, cosmetics, pharmaceuticals, shampoos, cleaners, polishes, gas conditioning agent used as a chemical intermediate for fatty alkanolamides, liquid detergents, morpholine, rubber chemicals, humectants. 

Fatty acid ethanolamides and isopropanolamides are solid or waxy products insoluble in water. Diethanolamides are usually pastes or liquids and show better dispersibility in water. In institutional and household formulations, shampoos, bath and shower preparations, fatty alkanolamides play the role of foam stabiliser, thickener, corrosion inhibitor, and ancillary agent that improves the skin compatibility of anionic surfactants. Undecylenic ethanolamide and undecylenic diethanolamide act as fungicides also [47]. Use of diethanolamine derivatives has legislative limitations today in some countries (but not its amides) because they are proved to be precursors of carcinogenic nitrosoamines. The probability of the nitrosoamine formation is assumed to increase in the presence of formaldehyde and formaldehyde-releasing preservatives [44-46]. 

Over 50% of the consumption of traditional blooming antistatic agents consists of ethoxylated amines and glyceryl monostearate (GMS), and much of the rest consists of alkyl sulfonates, fatty alkanolamides and amide ethoxylates. Films containing amide antistats usually pass the American Mil-B-81705C (commonly known as Mil spec) test for electrostatic dissipation when the film is a few days old, but not after three or four weeks. This has been attributed to the formation of crystallites of the antistatic agent. 

Fatty alkanolamides have many different applications, such as detergents, foam boosters, viscosity builders, and stabilizers. These are mostly in liquid formulations in applications such as dishwashing and shampoos. The fatty alkanolamides have also been evaluated as alternatives to nonylphenol ethoxylates [1],... 

The total amount of fatty alkanolamides produced in 1989 was 107,0001 declining to -60,000 metric tons in 2001. The prediction for the world market for 2006 was around 55,0001, declining especially in personal care applications (about -5 to -7%) based on calculations of Bizzari [2]. 

These data should be taken today just as an indication for process economics better reaction and separation technology increased the quality and economics of fatty alkanolamide production (Figure 13.1). 

Bizzari, S. N., Fatty alkanolamides, CEH data summary. Chemical Economics Handbook, SRI International, Menlo Park, CA, 2002. 

Surfactants Are the most important components improve the wetting ability of water, emusify and remove soil particles Alkylbenzene sulfates, e.g. linear alkylbenzene sidfonate (LAS) Alcohol sulfates, e.g. Fatty alcohol sulfates (FAS) Alcohol ether sulfates ot-Olefin sulfonates Alcohol ethoxylates Alkylphenol ethoxylates Fatty alkanolamides Fatty amine oxides Alkylpolyglucucosides Betaines Imidazolinium salts Quaternary ammonium compounds ... 

GAF CHEMICALS CORP. ALKAHIDE Fatty Alkanolamides (Continued) ... 

Fatty alkanolamide, modified Active % 100 Light color paste... 

Modified fatty alkanolamide Fatty Acid Proprietary % Free Fatty Acid 19.0 % Free Amine 19.0 Liquid NINOL 1301 ... 

Modified fatty alkanolamide Fatty Acid Proprietary Paste... 

Some variants of sulfosuccinates are derived from other substituted fatty molecules such as fatty alcohol ethoxylates, fatty amines, or fatty alkanolamides the recourse to amines (yielding sulfosuccinamates) is, however, less frequent. When using equimolar ratios, monoesters (sometime called half-esters ) are obtained, whereas with excess alcohol (or other substituted fatty molecules), diesters are obtained. 

Fatty alkanolamides are sulfated by treatment with chlorosulfonic acid in the presence of a low molecular weight alcohol, e.g. methanol or isopropanol (15-20%), to give a co-sulfate of the alcohol and the alkanolamide. For instance, this was achieved by heating tallow isopropanolamide with methanol and chlorosulfonic acid at 45... 

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