Surfactants quaternary ammonium compounds

Cationic surfactants Quaternary ammonium compounds (QACs)h ... 

Uses of quaternary ammonium compounds range from surfactants to germicides and encompass a number of diverse industries (see Table 1). 

Surface Applied Surfactants. Antistat agents can be appHed direcdy to the surface of a plastic part. Usually the antistat is diluted in water or in a solvent. The antistat solution is appHed by spraying, dipping, or wiping on the surface. The water or solvent dries leaving a thin film that attracts moisture. Since it is appHed to the surface, migration through the resin is not a factor. In practice, the quaternary ammonium compounds find the most use. They are soluble in water and effective at low concentrations. 

Quaternary ammonium compounds are cationic surfactants that bind well to anionic surfaces like the protein in hair. The ammonium end sticks to the hair, leaving the long fatty end of the molecule to act as a lubricant. They are slightly conductive, so they reduce the buildup of static electricity. Quats, as they are sometimes called, include compounds like stearalkonium chloride, disteardimonium chloride, quaternium-5, or quaternium-18, polyquaternium-10 and they are all similar in form and function to cetrimonium chloride. These compounds are also widely used as fabric softeners, for all of the same reasons they make good hair conditioners. They are also used to thicken the shampoo. 

Taking into consideration its physico-chemical properties, removal efficiencies, low biodegradability, predicted environmental levels, toxicity, and the need to provide sufficient safety margins for aquatic organisms, the demand for alternative cationic surfactants arose. Since 1991, DTDMAC has been replaced in some European countries due to producer s voluntary initiatives with new quaternary ammonium compounds, the esterquats. These contain an ester function in the hydrophobic chain (Table 1.3) that can be easily cleaved, releasing intermediates that are susceptible to ultimate degradation [24-26]. The effects of the phasing-out and replacement of DTDMAC can be demonstrated by the results of a Swiss study, where the surfactant... 

Paraquat (1,1 dimethyl, 4,4 bipyridyl) is a nonselective contact herbicide. It is used almost exclusively as a dichloride salt and usually is formulated to contain surfactants. Both its herbicidal and toxicological properties are dependent on the ability of the parent cation to undergo a single electron addition, to form a free radical that reacts with molecular oxygen to reform the cation and concomitantly produce a superoxide anion. This oxygen radical may directly or indirectly cause cell death. Diquat, l,T-ethylene-2,2 -dipyridylium, is a charged quaternary ammonium compound often found as the dibromide salt. The structure of diquat dibromide and that of the closely related herbicide paraquat can be seen in Fig. 4.5. 

Fabric Softening. The single largest market for quaternary ammonium compounds is as fabric softeners. The use of quaternary surfactants as fabric softeners and static control agents can be broken down into three main household product types rinse cycle softeners tumble dryer sheets and detergents containing softeners, also known as softergents. 

The quaternary ammonium compounds (qv) are manufactured by the reaction of an alkyl halide with a tertiary amine. The alkyl halide may be short-chain, long-chain, or benzyl. Selection of a long-chain alkyl group yields structures with variable composition and greatly adds to the chemical complexity inherent in this group. Investigation of structure-activity relationships has led to claims for superior efficacy or compatibility, most notedly with anionic surfactants in disinfectant-detergent cleaner systems, of closely related compounds in the family. 

Preservatives such as sodium benzoate, sorbic acid, and methyl and propyl parabens have been used in liquid and semisolid dosage forms. There have been reports that the parabens have been inactivated when used in the presence of various surfactants. This loss of activity was thought to be due to the formation of complexes between the preservative and the surfactant. The interaction between polysorbate (Tween) 80 and the parabens has been demonstrated by a dialysis technique (Ravin and Radebaugh, 1990). It has also been shown that molecular complexes form when the parabens are mixed with polyethylene glycol (PEG) and methylcellulose. The degree of binding was less than that observed with Tween 80. Sorbic acid also interacts with Tweens but does not interact with PEGs. The quaternary ammonium compounds are also bound by Tween 80, which reduces their preservative activity. 

Surfactants, emulsifiers Dissolve lipids, disrupt membranes, denature proteins, and inactivate enzymes in high concentrations, and act as wetting agents Cationic detergents are used to sanitize utensils, anionic detergents are used to launder clothes and clean household objects, and quaternary ammonium compounds are sometimes used as an antiseptic on skin... 

Traina, S.J., D.C. McAvoy, and D.J. Versteeg. 1996. Association of linear alkylbenzenesulfonates with dissolved humic substances and its effects on bioavailability. Environ. Sci. Technol. 30,1300-1309. Urano, K., and M. Saito. 1984. Adsorption of surfactants on microbiologies. Chemosphere 13, 285-293. Versteeg, D.J., and S.J. Shorter. 1992. Effect of organic carbon on the uptake and toxicity of quaternary ammonium compounds to the fathead minnow, Pimephales promelas. Environ. Toxicol. Chem. 11, 571-580. 

Quaternary ammonium compounds. These compounds are cationic surfactants if they contain a hydrocarbon chain of sufficient length. Example cetyltrimethyl-ammonium bromide, CH3(CFl2)isN+(CH3)3Br. See also Cationic Surfactant. 

In 1993, the European Union revised its criteria for classification and labelling of substances and preparations based on their potential to cause ocular lesions [5] and in 1995 new experimental data on the irritation potential of surfactant raw materials became available. This led CESIO, once again, to review its guidance on classification and labelling of anionic and non-ionic surfactants. It resulted in the increase in several classification and labelling recommendations. These revisions, together with the classifications for quaternary ammonium compounds and fatty amines and derivatives which remained unchanged from the 1990 Report, are contained in the latest report published in January 2000 [6]. 

Schomacker compared the use of nonionic microemulsions with phase transfer catalysis for several different types of organic reactions and concluded that the former was more laborious since the pseudo-ternary phase diagram of the system had to be determined and the reaction temperature needed to be carefully monitored [13,29]. The main advantage of the microemulsion route for industrial use is related to the ecotoxicity of the effluent. Whereas nonionic surfactants are considered relatively harmless, quaternary ammonium compounds exhibit considerable fish toxicity. 

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