Lauric diethanolamide

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). 

Part C.—The upper organic layer was removed and diluted with about 100 mL. of chlorinated solvent and azeotropically distilled until substantially all water had been removed. The cooled anhydrous solution was then filtered to remove precipitated salts and soaps after which the clear filtrate was distilled, the last traces of solvent being removed under reduced pressures, e. g., about 10 mm. mercury and at a temperature not exceeding 100° C. The pale liquid residue crystallized to a low-melting waxy material containing about 96% lauric diethanolamide, about 3% lauric acid, and about 1% diethanolamine ester. Source Krems 1954... 

The active ingredient for selenium sulfide lotion is selenium sulfide 2.5% w/v in aqueous suspension it also contains bentonite, lauric diethanolamide, ethylene glycol... 

Secondary surfactants are used for foam modihers, to enhance cleaning or even for viscosity enhancement. The principle secondary surfactants used in shampoos are amides such as cocodiethanolamide, lauric diethanolamide, or cocomonoethanolamide (see Table 5-3). Betaines are excellent foam modihers, and cocamidopropylbetaine is the most widely... 

Lauric diethanolamide Lauroyl diethanolamide Lauryl diethanolamide Definition Mixture of ethanolamides of lauric acid Empiricai C16H33NO3 Formuia CH3(CH2)ioCON(CH2CH20H)2 Properties M.w. 287.50 1 1 type wh. cryst. solid nonionic... 

Croda argues that ethoxylated amides (as opposed to ethoxy lated amines) are effective antistatic agents in polyethylene, but not necessarily in polypropylene. They are said to be faster-acting and more persistent than GMS. The higher molecular weight varieties are free from the volatility associated with another blooming antistat, lauric diethanolamide. 

Only primary thickeners are listed. Thickeners that depend on interaction with another component of a formulation are excluded. Thus, cosurfactants, such as lauric diethanolamide, are not listed because these should be categorized as cosurfactants that alter micelle structure. They are not primary thickeners. 

Occasionally it is found that an additive that has been extracted from a plastic will undergo a chemical change upon reaction with the extract. A case in point is that of the antistatic additive lauric diethanolamide which upon reaction with aqueous extraction liquids is hydrolysed to diethanolamine and lauric acid. In these circumstances it is not only the toxicity of lauric diethanolamide that must be considered but also that of the two hydrolysis products. In fact, it has been ascertained that during a 14 day extraction test on PP carried out at 60 "C some 100% of the extracted diethanolamide is hydrolysed ... 

Continuous process. Methyl laurate and diethanolamine (1 1.1) containing ca. 0.2% of a soln. of Na in methanol passed at 149 /125 mm through a thin-film reactor with high speed rotor allowing a residence time of ca. 10 sec. lauric diethanolamide. Y and purity ca. 9T%. J. A. Monick, J. Am. Oil Chemists Soc. 59,213 (1962). 

Additives used in final products Antistatics carbon black, copper complex of polyacrylic add, ethoxylated amines, fatty diethanol amines, glycerol monostearate, graphite, ionomer, lauric diethanolamide, polyethylene glycol, quaternary ammonium compound, trineoalkoxy zirconate Antiblocking diatomaceous earth, natural silica, slloxane spheres, synthetic silica, talc, zeolite Blowing agents Release stearyl erucamide Slip erucamide, ethylene bisoleamide, oleamide Process aid Thermal stibullzers UV stabilizers ... 

In order to give an idea of the care with which such methods have to be developed several detailed examples are given of previously unpublished methods developed in the Author s laboratories for the determination of particular types of extractables in extraction liquids, e.g., dilaurylthiodipropionate, Nonox Cl, antioxidants and Ethylon (lauric diethanolamide). 

Examples of the possibility of a degradation of an additive and its effect on the design of the analytical procedure are supported next by means of an example, i.e., the antistatic additive lauric diethanolamide which has been used in foodgrade polyolefin and polystyrene formulations. Lauric diethanolamide upon migration... 

In fact any of this additive which extracts from a polymer into distilled water at 60 °C is hydrolysed fairly completely within a few days. The analytical problem, resolves itself, therefore, into the determination of traces of DBA degradation product in the presence of relatively small concentrations of lauric diethanolamide. A method for the determination of lauric diethanolamide and DBA in the aqueous and alcoholic extraction liquids of the British Plastics Bederation (BPB) test conditions and in liquid paraffin is described next. 

Determination of Lauric Diethanolamide and its Degradation Products in Aqueous Fatty Extraction Liquids... 

Lauric diethanolamide is a fairly unreactive substance. A likely approach to the problem of determining low concentrations of this substance involved hydrolysing it to DBA and fatty acid and determining the former by a conventional iodometric method. The lauric diethanolamide content of the extractant could then be calculated from the amount of DBA produced upon complete hydrolysis. It is more appropriate to determine DBA rather than the fatty acid, as it was possible that the extractant could contain fatty acids originating from sources other than hydrolysis of the dialkanolamide, (e.g., free fatty acids or their metal salts or fatty acid esters, all of which might be present in the original polymer). 

To estimate lauric diethanolamide it is first necessary to hydrolyse it to DBA, which can then be determined by the periodic acid method. Tests to determine the conditions necessary to completely hydrolyse lauric diethanolamide (Table 13.1) showed that it hydrolyses quite slowly. In fact, a reflux period of approximately 20 hours with 0.03 N acid is needed to hydrolyse the dialkanolamide completely. The effect of increasing... 

Sulfuric acid, reflux time (h) Recovery (% of added amount of lauric diethanolamide) ... 

Table 13.2 Investigation of hydrolysis conditions required for the conversion of lauric diethanolamide to DEA...

Using commercial lauric diethanolamide which had been twice recrystallised from methanol (assumed to be 100% lauric diethanolamide for the purpose of calculating results). 

Determination of Lauric Diethanolamide and DEA in the Distilled Water Extractant... 

The results in Table 13.3 confirm that lauric diethanolamide is indeed hydrolysed by contact with distilled water for 10 days at 60 °C. To estimate free DEA, one portion of the extractant was analysed directly by the periodic acid procedure. The other portion of extractant was refluxed with 0.1 N sulfuric acid for 6 hours to hydrolyse... 

Table 13.3 Hydrolysis of lauric diethanolamide in distilled water during 10 days at 60 °C ...

Lauric diethanolamide (g/100 ml test solution) % of original lauric diethanolamide addition ... 

As lauric diethanolamide is extensively hydrolysed to DEA by distilled water, (i.e., heating for 10 days at 60 C) it would be expected that even more extensive hydrolysis of the additive might occur under the alkaline conditions prevailing in the case of the 5% w/v sodium carbonate extractant. The results in Table 13.4 show that lauric diethanolamide is almost completely hydrolysed to DEA and fatty acid in aqueous sodium carbonate when heated to 60 °C for 10 days. 

In the 50% wiv aqueous ethyl alcohol extractant, lauric diethanolamide is not completely hydrolysed to DEA when refluxed in the presence of 0.1 N sulfuric acid for periods of up to 8 hours, (i.e., low total recoveries obtained). 

The results in Table 13.5 show that the low lauric diethanolamide recoveries must be due to a slowing down in the rate of hydrolysis of lauric diethanolamide to DEA, brought about by the presence of ethyl alcohol during the preliminary reflux with... 

Experiments on synthetic solutions of lauric diethanolamide in the 50% w/v ethyl alcohol aqueous extractant showed (Table 13.6) (rows 1-5) that in the absence of ethyl alcohol a recovery of between 100% and 120% of the added amount of lauric diethanolamide is obtained by the periodic acid method following hydrolysis with either 0.1 N or 1 N sulfuric acid for 6 to 8 hours. However, in the presence of ethyl alcohol, the lauric diethanolamide recoveries obtained following hydrolysis with 0.1 N sulfuric acid (row 6) are only about two-thirds of the expected value, but when the acid strength during hydrolysis is increased to 1 N, a quantitative lauric diethanolamide recovery is obtained (row 7-8). Thus, the low lauric diethanolamide recoveries observed earlier can be overcome by increasing the sulfuric acid strength during hydrolysis from 0.1 to 1.0 N. 

No. Dilution of extraction liquid with distilled watCT CcHiceDtration of lauric diethanolamide in original 200 ml extraction liquid (ppm) Volume of diluted extraction liquid used for determination of lauric diethanolamide (ml) Concentration of ethyl alcohol in diluted extraction liquid during reflux with sulfuric add (% wAf) Concentration of sulfuric add in diluted extraction liquid during reflux (N) Volume of distilled water added to extraction liquid immediately prior to iodine back titration (ml) Recovery of added lauric diethanol-amide (%)... 

Synthetic solution of lauric diethanolamide (0.0080 g)" in 5% citric add, (200 ml heated under BPF test conditions, i.e., 10 days at 60 °C) before appKcation of barium carbonate precipitation and ion-exchange procedures. ... 

The weight of lauric diethanolamide (0.0080 g) taken would, upon complete hydrolysis yield 0.0029 g diethanolamine. The fact that this weight of DEA was obtained in the column effluent indicated that lauric diethanolamide is completely hydrolysed by 5% citric acid during 10 days at 60 i.e., the sulfuric acid... 

Although complete or partial hydrolysis of lauric diethanolamide to DEA occurs with the four aqueous extractants, no such hydrolysis was expected in the case of a solution of lauric diethanolamide in the liquid paraffin extractant. 

---