Diethanolamine fatty acids

Edible ester-type surfactants can be based on glycerol, sorbitol, or propylene glycol. The foam stabilization and viscosity-thickening properties of diethanolamine-fatty acid condensates are related directly to their diethanolamide content on the other hand, solubility in water is shown only by the 2 1 condensate. 

Both quaternized triethanolamine fatty acid esters [167,168] and methyl-diethanolamine fatty acid esters [169-174] have found new industrial uses in the paper softening area. Quaternized triethanolamine fatty acid esters are described for use as softeners or debonders for the manufacture of soft paper tissues and paper towels. These new softeners/debonders are claimed to exhibit premium water absorbency and give an improved softness to the paper [68,168,175,176]. 

Chem. Descrip. Diethanolamine fatty acid condensate Uses Surfactant for all-purpose cleaners, liq. dishwashing, rug shampoos, laundry detergents, rinse acids grease emulsifier soil dispersant Features Can be compounded with liq. soaps and other syn. detergents Properties Liq. 

Hlkanolamides. The fatty acid alkanolamides are used widely ia shampoo formulations as viscosity and lather builders. They are formed by the condensation of a fatty acid with a primary or secondary alkanolamine. The early amides were compositions of 2 1 alkanolamine to fatty acid. Available technology allows the formation of amides with a 1 1 ratio of these additives. These amides are classified as superamide types. The typical amide used ia shampoo preparations usually contains the mono- or diethanolamine adduct, eg, lauric diethanolamide [120-40-1] (see Amides, fatty acid). 

Cosmetics and Personal Care Products. Alkanolamines ate important taw materials in the manufacture of creams (95—97), lotions, shampoos, soaps, and cosmetics. Soaps (98) formed from triethanolamine and fatty acids ate mild, with low alkalinity and excellent detergency. Triethanolamine lauryl sulfate is a common base for shampoos (99—101) and offers significant mildness over sodiumlauryl sulfate. Diethanolamine lauryl sulfate and fatty acid soaps of mono- and trietban olamine can also be used in shampoos and bubble bath formulations. Chemistry similar to that used in soluble oils and other emulsifiers is appUcable to cleansing creams and lotions (102,103). Alkanolamides or salts ate added to the shampoo base to give a smooth, dense foam (104). 

The second type of diethanolamide is the 1 1 or superamide which contains components of the reaction of one mole fatty acid and one mole diethanolamine. A typical superamide composition is >90% diethanolamide, 7% unreacted diethanolamine, and 2.5% amine and amide ester. 

Regular fatty acid diethanolamides are prepared by heating fatty acid with diethanolamine at 160—180°C for 2—4 h. Superamides are prepared by heating a fatty acid methyl ester with an equimolar amount of diethanolamine at 100—110°C for 2—4 h the methanol formed is distilled off (Table 23). 

These ingredients are made from fatty acids in coconut oils, reacted with diethanolamine, or its mono- or triethanolamine relatives. 

A cooling, lubricating, and cleaning agent for use by the metalworking industry has been patented. It is produced by the condensation reaction of an excess diethanolamine or monoethanolamine with boric acid and an ether carboxylic acid or mixtures of ether carboxylic acids and fatty acids [46]. An advantage of these products is that they prevent the deposition of lime soaps. 

Amine salts of a-sulfonated fatty acids and esters are also used as antistatic agents. Mixtures of alkyl a-sulfo fatty acid ester diethanolamine salts and hexa-decyl stearate or butyl stearate are coated onto nylon yarn after fiber formation and before stretching [97]. Polypropylene can be made antistatic with an amine salt of a-sulfolauric acid [C10H21CH(SO3Na)COO +NH(CH2CH(OH) CH3)3] [98]. 

The criteria for choosing inhibitors in this study were the ability to compete with diethanolamine for the nitrite and lack of toxicity. An attempt was made to cover as broad a group as possible within the limits of feasibility. Ascorbic acid in its water soluble form and its oil soluble form, the palmitate, represent the enediols, Sorbate is a diene fatty acid which has been shown to inhibit nitrosation (10), Since the pK of sorbic acid is 4,76, at the pH of these experiments, both water soluble sorbate ion and oil soluble sorbic acid are present in significant amounts. Sodium bisulfite is a strong inorganic reducing agent which has an acceptable lack of toxicity at the concentration... 

Since a-tocopherol destroys nitrite in the system in absence of the oil phase, we may postulate that the ineffectiveness of these two oil soluble inhibitors resulted from their absence from the aqueous phase. Diethanolamine is miscible with water and presumably its nitrosation occurs in the aqueous phase. There is a significant difference in the solubility characteristics of ascorbyl palmitate. The reducing portion of the molecule is water soluble. Thus the ascorbate moiety may be in the aqueous phase while the fatty acid tails may lie within the oil globules. The a-tocopherol and the BHA may well be effective if they are dispersed in the aqueous phase after preparation of the emulsion. This will be investigated in future experiments. 

A solution of a surfactant mixture in liquid paraffin, containing oil-soluble oxyethylated alkylphenol, having the formula with an Cg to C12 alkyl rest, the alkylphosphate of a higher fatty acid alcohol (RO)2PO — OH where R is Cio to C20, and a fatty acid amide of diethanolamine, are suitable for removing oils... 

P. E. Chaplanov, A. D. Chemikov, O. G. Mironov, G. N. Semanov, A. G. Svinukhov, A. G. Yaremenko, F. V. Linchevskij, N. A. Melnik, 1. A. Murashev, and I. S. Akhmetzhanov. Removing oils and petroleum products from water surfaces—using mixture of oxyethylated alkyl-phenol, alkyl-phosphate and fatty acid diethanolamine. Patent SU 1325816-A, 1992. 

FADAs are nitrogen derivatives of coconut oil synthesised from fatty acid and diethanolamine. Equimolar amounts of the two starting compounds yield water-insoluble monoethanolamides, whereas the reaction of two moles of diethanolamine with one of the acids results in water-soluble FADA possessing the typical alkyl chain distribution with the C12/C14 homologues prevailing [33]. 

Free diethanolamine is reported to be a contaminant in fatty acid-diethanolamine condensates (amides of coconut oil acid, oleic acid and lauric acid) at levels ranging from < 1% to nearly 10% (National Toxicology Program, 1999b,c,d). Diethanolamine also occurs as a contaminant in triethanolamine products (National Toxicology Program, 1999e). 

Carboxylic Amides. Carboxylic amide nonionic surfactants are condensation products of fatty adds and hydroxyalkyl amines. They include diethanolamine condensates, monoalkanolamine condensates, and polyoxyethylene fatty acid amides. 

The soaps of the ethanolamines are extensively used in textile treating agents, in shampoos, and emulsifiers. The fatty acid amides of diethanolamine are applied as builders in heavy-duty detergents, particularly those in which alkylaryl sulfonates are the surfactant ingredients. The use of triethanolamine in photographic developing baths promotes fine grain structure in the film when developed. 

The original work by Kritchevsky [36] involved heating equimolar quantities of dietha nolamine and fatty acid. This yielded, as expected, a water insoluble waxy solid. However, when the diethanolamine content was doubled the reaction was modified to produce a liquid, which was soluble in water and foamed and wetted well even in hard water. Its properties were quite unlike a physical blend of the 1 1 diethanolamide with diethanolamine. It became known as a low activity1, a 2 1, Kritchevsky or Ninol type alkanolamide. 

SYNS AMIDES, coco, N,N-BIS(HYDROXYETHYL) CUNDROL 200CGN CUNDROL 202CGN CLINDR-OL SUPERAMIDE lOOCG COCAMIDE DEA COCONUT DIETHANOLAMIDE COCONUT DIETHANOLAMINE COCONUT OIL ACID DIETHANOLAMINE COCONUT OIL ACID DIETHANOLAMINE CONDENSATE ETHYLAN LD N,N-BIS(2-HYDROXYETH-YL)COCOAMIDE N,N-BIS(2-HYDROXYETHYL)-COCONUT FATTY ACID AMIDE N,N-BIS(2-HYDRO-XYETHYL)COCONUT OIL AMIDE NCI-C55312 NINOL2012E... 

Alkanolamides of fatty acids The condensation of fatty acids with mono-thanolamines or diethanolamines yields a group of products called alkanolamides. They usually contain a range of surface-active byproducts such as amino esters. 

Fatty Amides. Cocomonoethanolamide and cocodiethanolamide formed by the reaction of fatty acids or esters with monoethanolamine or diethanolamine are popularly used as foam boosters for shampoos and detergent products. 

A second major type is the Kritchevsky type made from alkanolamine and fatty acids in the ratio of 2 1. Such product contains 60-70% alkanolamide plus byproducts. If diethanolamine is used in addition to the mentioned byproducts, some morpholine and piperazine derivatives are also obtained. The excess alkanolamine renders the product water soluble (29). Both are of commercial importance as detergent and detergent additives. 

Depending on whcih of the four types of alkanolamide is to be produced, the starting material could be either fatty acid, methyl ester, or triglyceride (coconut oil) and monoethanolamine or diethanolamine. Usually, a batch system of manufacturing is employed, as shown in Figure 20. 

If fatty acid is the starting material, a different operating parameter is used to drive off the water formed during the reaction. If superamide is to be produced, cocomethyl ester and diethanolamine can be used as the starting materials in a mole ratio of 1 1. These materials are charged to the reactor with 0.3-0.5% sodium methylate as the catalyst. The reaction is carried at around 100°C and a vacuum of 4-5.3 kPa for a period of 90-120 min. The reaction temperature can be lowered to 70-75°C by employing a vacuum of less than 4 kPa. The reaction time takes longer to enable the maximum vaporization of the methanol byproduct. The methanol is rectified and recycled for use in the transesterification of the coconut oil to produce the methyl ester. 

Diethanolamine is primarily used in pharmaceutical formulations as a buffering agent, such as in the preparation of emulsions with fatty acids. In cosmetics and pharmaceuticals it is used as a pH adjuster and dispersant. 

The manufacture of fatty acid ethanolamides can start from a fatty acid or from the ester, acid chloride or acid anhydride, which is reacted with a monoethanolamine or diethanolamine. Industrially, fatty acids or fatty acid esters are exclusively used. In general, the procedure followed is to take one component and add the other component dropwise. Thereafter the mixture is heated to 130 to 180° and one mol of water or if using the fatty acid ester, one mole of alcohol is driven off per mol of acid. 

Where it is necessary to incorporate the drug into the oil phase of a dispersed o/w system, a hydrophobic drug is required. The drug substance should have a low aqueous solubility and it may be necessary to select a more lipophilic, low melting salt (e.g. a fatty acid ester salt such as stearate or an amine salt such as diethanolamine) or... 

N-Acyl L-Glutamates (AG), RCONHCH(COO M+)CH2CHyCOO M+, M=H+ or Cation Produced by /V-acylation of L-glutamic acid with fatty acid chloride in a mixed solvent of water and water-miscible organic solvent. RCO is usually from coconut and tallow acids. AG is a dibasic acid, so both mono- and di-neutralized materials are possible. The carboxyl group at the a-position is neutralized prior to that at the y-position. The water solubility of monosodium AG is low, so organic amines, i.e., triethanolamine or diethanolamine, or K+ are used as counter-ions. 

The transamidation reactions, usually with diethanolamine, are frequently used to obtain diethanolamides of fatty acids (well known as nonionic surfactants [51-57]). Fatty acid diethanolamides are sometimes used together with other polyols, to obtain rigid PU foams. The fatty acid diethanolamides are bifunctional compounds and improve the compatibility of various polyolic systems very much, with pentanes used as blowing agents for rigid PU foams (reaction 17.15). 

Fatty acids, coco, compds. with diethanolamine. 

Coconut oil acids, diethanolamine salt Coconut oil fatty acids, diethanolamine salt EINECS 263-153-4 Fatty acids, coco, compds. with diethanolamine... 

N,N-Bis(2-hydroxyethyl)(coconut oil alkyl)amine N,N-Bis(hydroxyethyl)oocoamine Coconut fatty acid diethanolamide Diethanolamine coconut fatty acid condensate EINECS 263-163-9 Ethanol, 2,2 -lminobis-, N-cooo alkyl derivs. 

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