Triethanolamine ester quats

At present, triethanolamine ester quats (TEAEQ), with a formal structure of (RC02CH2CH2)2N+(CH3)CH2CH2OH-CH3SC>4 are the fabric softeners of choice in Europe and elsewhere, replacing the imidazolinium and dialkyldimethyl ammonium types. 

Chem. Descrip. Dioleic acid triethanolamine ester quat ionic Nature Cationic Uses Surfactant, softener Properties Liq. 90% act. 

Chem. Descrip. Ditallow acid triethanolamine ester quat... 

Chem. Descrip. Triethanolamine ester quat Ionic Nature Cationic Uses Surfactant for softeners Properties Wax-like 90% act. 

The main product used to be ditallow dimethyl am-monitim chloride as a fabric softener in household products and in industrial applications. Because it has shown substantial toxicity to fish, it has been replaced by products with ester groups ( ester quats ), which are readily Itydrolyzed in water. They are obtained by alkylation of difatty acid esters of triethanolamine with dimethylsulfate ... 

Wilkes, A. J., C. Jacobs, G. Walraven, J. M. Talbot, Quatemized triethanolamine esters (ester-quats) by HPLC, HRCGC, and NMR, World Surfactants Congr.,4th, 19%, /, 389-412. 

FIG. 8 Normal phase HPLC analysis of a crude ester quat based on quatemized tallow triethanolamine esters. Peak identies 1, fatty acid methyl ester 2, free fatty acid 3, unquatemized triesteram-ine 4, tetraoctylammonium bromide internal standard 5, diesteramine 6, triesterquat 7, diesterquat 8, monoesteramine 9, monoesterquat. ELS detection. (Reprinted with the author s permission from Ref. 288.)... 

Proton NMR of ester quats (made by quaternization of a mixture of mono-, di-, and triesters of triethanolamine) with a 300-MHz instrument allows determination of unsaturation, ester number, molecular weight, and degree of quaternization all of these, of course, are average values (49). 

Ester quat—Quaternized tallow triethanolamine esters unquater-nized mono-, di-, and triesteramine impurities and fatty acid impurities separated triester-quat, diesterquat, and monoester-quat resolved elution according to decreasing alkyl character Distearyldimethylammonium chloride, cocoalkyldimethylbenzylam-monium chloride, cetyltrimethylammonium bromide, and a quaternary imidazoline compound resolved from J S V S ier environmental analysis... 

The new quats generation presents readily biodegradable surfactants the long chains of which are interrupted by ester groups, thus named "esterquats" [102, 108]. Esterquats are derived frequently from the diester of triethanolamines and the partially hydrogenated tallow or oleic acid followed by a diester quaternisation. The final product, N-methyl-N,N-di[2-(Ci6-i8-acyIoxy)-ethyl]-N-(2-hydroxyethyl)ammonium methosulphate (VIII), of the formula... 

Quatemized esteramines are usually derived from fat or fatty acid which is reacted with an alkanolamine to give an intermediate esteramine. The esteramines are then quatemized. A typical reaction scheme for the preparation of a diester quat is given in Figure 14.8. Two moles of fatty acid methyl ester are reacted with one mole of triethanolamine at 75-115°C in the presence of sodium methoxide catalyst. The resultant esteramine is then quatemized with dimethyl sulfate. Free fatty acids and glycerides have been used in place of the fatty acid methyl ester. 

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