Diethanolamides

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). 

Alkyl(R) length RCONHj Amide RCONHCH2CH2OH Monoethanolamide RC0N(CH2CH20H)2 Diethanolamide ... 

Another subclass of substituted amides that is of great commercial value is the ethoxylated amides. They can be synthesized from alkanolamides by chain extending with ethylene or propylene oxide or by ethoxylation directly from the primary amide (46—48). It was originally beheved that the stepwise addition of ethylene oxide (EO) would produce the monoethano1 amide and then the diethanolamide when sufficient ethylene oxide was added (49), but it has been discovered that only one hydrogen of the amide is substituted with ethylene oxide (50—53). As is typical of most ethylene oxide adducts, a wide distribution of polyethylene oxide chain length is seen as more EO is added. A catalyst is necessary to add ethylene oxide or propylene oxide to a primary or an ethoxylated amide or to ethoxylate a diethoxy alkanolamide synthesized from diethanolamine (54). 

Sulfated Acids, Amides, and Esters. Reaction with sulfuric acid may be carried out on fatty acids, alkanolamides, and short-chain esters of fatty acids. The disodium salt of sulfated oleic acid is a textile additive and an effective lime soap dispersant. A typical sulfated alkanolamide stmcture is CiiH23C0NHCH2CH20S03Na. Others include the sulfates of mono and diethanolamides of fatty acids in the detergent range. The presence of... 

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. 

The presence of the large excess of diethanolamine and its derivatives in regular diethanolamides increases water solubiUty compared to... 

Table 22. Physical Form and Solubility of Fatty Acid Diethanolamides...

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). 

Monoa.lka.nola.mine Condensates. Coco, lauric, oleic, and stearic monoethanolamides and monoisopropanolamides are the principal surfactants ia the monoalkano1 amide group (Table 24). Monoalkanolamides are generally water-iasoluble soHds that are easily solubilized by hydrophilic surfactants. Except for solubiUty and viscosity, properties and uses are similar to the diethanolamides. Manufacturing processes and yields have been described (96). 

Nonionic surfactants perform well in nonpolar polymers such as polyethylene and polypropylene. Examples of nonionic surfactants ate ethoxylated fatty amines, fatty diethanolamides, and mono- and diglycetides (see Amines, fatty amines Alkanolamines). Amphoteric surfactants find Httle use in plastics (134). 

Coconut fatty acid monoethanolamide coconut fatty acid diethanolamide coconut fatty acid triethanolamide N-coco alkyl derivatives... 

The performance of AOS vs. the other surfactants was tested with three foam boosters, namely, amide oxide (AO), lauryl myristic monoethanol amide (LMMEA), and coco diethanolamide (coco DEA) at 90 10 anionic/booster ratio. Blends were evaluated at 0.025% active, 41 °C, and 140 ppm vegetable shortening oil. The results in Fig. 21 show that AOS blends outperform the reference standard whereas the other blends were of equal or less performance. The AOS/LMMEA blend gave superior performance. It was further shown that the addition of a small amount of AES (10% on total actives) further enhanced the performance of the AOS system (see Fig. 22). AOS when formulated with AES and amide therefore has outstanding dishwashing performance and is an attractive candidate for use in formulating light-duty liquids. 

Sodium a-sulfomethylmyristate is used together with the sodium salt of hardened beef tallow fatty acid to produce a soap with little skin irritation [88]. Shampoos for application to hair as well as skin comprise a-sulfo fatty acid ester salts, fatty acid dialkanolamides, and citric acid. For example, a shampoo that consists of 15% sodium a-sulfoethylmyristate, 3% lauric acid diethanolamide, 0.5% citric acid, and 81.5% water is very effective even in hard water and only slightly irritating to the skin [89]. 

The alkanephosphonic acid dichlorides obtained by these methods are converted with amines, with all reactions carried out in solvents such as acetone, benzene, or diethyl ether at 10°C with triethylamine as HC1 captor. The conversion runs quantitatively followed by a purification with the help of column chromatography with chloroform/methanol in a ratio of 9 1 as mobile phase. The alkanephosphonic acid bisdiethanolamides could be obtained as pure substances with alkane residues of C8, C10, C12, and Ci4. The N-(2-hydroxyethane) alkanephosphonic acid 0,0-diethanolamide esters were also prepared in high purity. The obtained surfactants are generally stable up to 100°C. Only the alkanephosphonic acid bismonomethylamides are decomposed beneath this temperature forming cyclic compounds. 

Antistatic agents Ethoxylated amines, lauric acid diethanolamide, glycerol monostearate... 

Coconut, fatty acid composition, 5 56t Coconut diethanolamide... 

Monod kinetic relationship, 25 898 Monoethanolamine (MEA) physical properties of, 2 123t specifications, 2 132t Monoethanolamine carbonate, 4 812 Monoethanolamine lauryl sulfate, effect of coconut diethanolamide on foaming, 2 453t... 

The GC analysis of silylated derivatives of ethoxylated amines and fatty acid diethanolamides, among other non-ionic surfactants, has been described for many years and reviewed recently [43]. However, most of the determinations deal with the use of old packed columns for the characterisation of commercial blends and there are no applications of GC to their study in the environment. 

Fatty acid and unsaturated fatty acid mono- and diethanolamides Fatty acid mono- (FAMA) and diethanol amides (FADA) with the general formula (C,32n+1-C(0)N(HyCH2-CH2-0H)2 x = l or 0) are presented with their general structural formulae in Fig. 2.9.28(a) and (b). These surfactants have found a widespread application in household and personal care formulations because of their quite good... 

A commercial blend of this FADA derivative was examined by MS-MS. The application ofESI-FIA-MS(+)tothis very pure blend resulted in a single [M + H]+ ion at m/z 370. Then ESI-FIA-MS-MS(+) was performed and the diethanolamide derivative of this unsaturated fatty acid showed a comparable behaviour to that observed with saturated diethanolamides [16], i.e. fragments with m/z 88, 106, 352 and (370-61 = 309) as shown in the CID spectrum in Fig. 2.9.33 were generated, which can then be explained as presented in the inset [24]. 

Fig. 2.9.33. ESI-FIA-MS-MS(+) (CID) product ion mass spectrum of parent ion with m/z 370 of industrial blend of unsaturated FADA surfactant compound could be identified as diethanolamide derivative of oleic acid (CH3-C7H14-CH=CH-C7H14-C(0)-N(CH2-CH2-OH)2) (inset) fragmentation scheme observed under CID conditions [16].

Based on their use in industrial and domestic applications and abundance in environmental samples, six surfactants were selected by the participants of interlaboratory study I. Two different standard mixture solutions (standards II and 12) were distributed to all participants for the preparation of the calibration graphs. Standard II contained Arkopal N100 (NPEO), Marlamid DF 1218 (coconut fatty acid diethanolamide, CDEA) and Marlon A 350 (linear alkylbenzene sulfonate, LAS) at 1000 mg L-1 for each compound, while standard 12 contained Rewopol NOS 5 (nonylphenol ethoxylate sulfate, NPEO-SO4),... 

Fatty acid diethanolamides (FADAs) are used in certain household textile washing and hand dish-washing formulations. The presence of coconut diethanolamides (CDEAs) with an alkyl chain between 7 and 15 C units has been reported in municipal wastewaters in Germany at levels of 111—124 i,g L 1 [31] in influent and 14 i,gL 1 in effluent indicating approximately 90% elimination, while the monitoring of CDEAs in a Swedish WWTP indicated significantly lower removal (about 40%). Other studies [8,29,32,33] reported levels up to 470 xg L-1 in raw influents (Table 6.1.7). Very low concentrations found in effluents indicate efficient elimination (>96%), whereas nothing is known about the formation of persistent metabolites. 

DEQ DM DTD MAC EO FADA LAB LAS M MBAS MCPEG Lever s diester quat dialkyldimethyl ammonium ditallow dimethylammonium chloride ethylene oxide fatty acid diethanolamide linear alkylbenzene linear alkylbenzene sulfonate R3S1O0.5 methylene blue active substances mono carboxylated PEG... 

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