Ammonium detergents

Balias, N., Zakay, N., Sela, I., and Loyter, A., Liposome bearing a quaternary ammonium detergent as an efficient vehicle for functional transfer of TMV-RNA into plant protoplast, Biochimica et Biophysica Acta, 1988, 939, 8-18. 

Pinnaduwage, P., Schmitt, L., and Huang, L., Use of a quaternary ammonium detergent in liposome mediated DNA transfection of mouse L-cells, Biochimica et Biophysica Acta, 1989, 985, 33-37. 

Avigad and Milner224 used a turbidimetric method based on the measurement of residual turbidity caused by complexing the acid polysaccharide with such quaternary ammonium detergents as cetyl-pyridinium bromide. The activity unit was expressed as the amount of enzyme bringing about a decrease of absorbance at 400 nm of 0.01/min. 

Similar delivery systems have been designed using other cationic polymers, including lipopolyamines (161), amphipathic peptides (162), polylysine lipids (163), cholesterol (164), quaternary ammonium detergents (165), polyamidoamines called dendrimers, polyethylenimines or chitosan, diethylaminoethyl dextran (DEAE dextran), and polybrene. 

This discussion emphasizes the need to understand the nature of the compound to interpret its sorption behavior. Many compounds of environmental significance are nonpolar and one tends to relate sorption to aqueous solubihty. The herbicide, Paraquat, by contrast shows a A oc of 1 x 10 despite having a high aqueous solubility (>600 gL ). This compound is a bipyridinium salt and the high tendency to sorb would be due to cation exchange not partitioning. A comparable response would be expected with quaternary ammonium detergents. 

Valko and DuBois made the interesting observation that bacteria apparently killed by cationic quaternary ammonium detergent germicides may be revived by the addition of a high molecular weight anion, provided that the application of the latter occurs within a period of 10-30 min. 

Palmitic acid (hexadecanoic acid) is the source of the hexadecyl (cetyl) group in the following compounds. Each is a mild surface-acting germicide and fungicide and is used as a topical antiseptic and disinfectant. They are examples of quaternary ammonium detergents, commonly called "quats."... 

The most widely used alkyl sulfate in shampoo preparation is lauryl sulfate. The alkyl component of this sulfate ranges from C-10 to C-18 with a predominance of the C-12 (lauryl) component. By distillation of the fatty alcohol, certain cuts can be obtained which offer the best effects in foaming, cleansing, and rinsing properties for the alkyl sulfate preparation. The range which appears to be most desirable is between C-12 and C-16. Lauryl sulfate detergents are available in various salt forms with the sodium, ammonium, and triethanolamine types being used most frequently in shampoos. 

Ammonium lauryl sulfate [2235-54-3] is available as an approximately 28% active, clear, Hquid form. It has greater solubiHty than the sodium salt and is more likely to be used in formulating clear shampoos. Systems using this detergent show their best stabiHty at pH between 6 and 7. Lower pH would tend to hydrolyze the detergent, eventually releasing ammonia. 

About 264,000 metric tons of elemental capacity is available in North America, plus another 79,000 t (P equivalent) of purified wet phosphoric acid (14). About 85% of the elemental P is burned to P2 5 hydrated to phosphoric acid. Part of the acid (ca 21%) is used direcdy, but the biggest part is converted to phosphate compounds. Sodium phosphates account for 47% calcium, potassium, and ammonium phosphates account for 17%. Pinal apphcations include home laundry and automatic dishwasher detergents, industrial and institutional cleaners, food and beverages, metal cleaning and treatment, potable water and wastewater treatment, antifree2e, and electronics. The purified wet acid serves the same markets. 

Sulfation by sulfamic acid has been used ia the preparation of detergents from dodecyl, oleyl, and other higher alcohols. It is also used ia sulfating phenols and phenol—ethylene oxide condensation products. Secondary alcohols react ia the presence of an amide catalyst, eg, acetamide or urea (24). Pyridine has also been used. Tertiary alcohols do not react. Reactions with phenols yield phenyl ammonium sulfates. These reactions iaclude those of naphthols, cresol, anisole, anethole, pyrocatechol, and hydroquinone. Ammonium aryl sulfates are formed as iatermediates and sulfonates are formed by subsequent rearrangement (25,26). 

Eor use in paint strippers, one of its first appHcations, methylene chloride is blended with other chemical components to maximi2e its effectiveness against specific coatings. Typical additives include alcohols, acids, amines or ammonium hydroxide, detergents, and paraffin wax. Paint stripping formulations without methylene chloride have not as yet been shown to be as effective as those with methylene chloride. 

Several cleaning formulations for specific uses contain unreacted polyamines. Examples include mixtures of ammonium alkylbenzenesulfonate, solvents, and PIP which give good cleaning and shine performance on mirrors and other hard surfaces without rinsing (305), and a hard-surface cleaner composed of a water-soluble vinyl acetate—vinyl alcohol copolymer, EDA, cyclohexanone [108-94-1] dimethyl sulfoxide [67-68-5] a surfactant, and water (306). TEPA, to which an average of 17 moles of ethylene oxide are added, improves the clay sod removal and sod antiredeposition properties of certain hquid laundry detergents (307). 

Miscellaneous Derivatives. Fimehc acid is used as an intermediate in some pharmaceuticals and in aroma chemicals ethylene brassylate is a synthetic musk (114). Salts of the diacids have shown utUity as surfactants and as corrosion inhibitors. The alkaline, ammonium, or organoamine salts of glutaric acid (115) or C-5—C-16 diacids (116) are useflil as noncorrosive components for antifreeze formulations, as are methylene azelaic acid and its alkah metal salt (117). Salts derived from C-21 diacids are used primarily as surfactants and find apphcation in detergents, fabric softeners, metal working fluids, and lubricants (118). The salts of the unsaturated C-20 diacid also exhibit anticorrosion properties, and the sodium salts of the branched C-20 diacids have the abUity to complex heavy metals from dilute aqueous solutions (88). 

Acid Detergent Fiber. The ground sample is heated for 1 h under reflux in a solution of 2% cetyltrimethyl ammonium bromide [57-09-0] in IN sulfuric acid [7664-93-9]. The acid hydrolyzes and dissolves the nonceUulosic polysaccharides. The insoluble residue, relatively free of hemiceUuloses and containing aU the ceUulose and lignin, is filtered, dried, and corrected for ash to give the ADF value. 

Ammonium sulfate detergents SIL G 25 detergent plate (M acherey-N agel) [200, 201]... 

The zinc. salts of these acids are extensively used as additives to lubricating oils to improve their extreme-pressure properties. The compounds also act as antioxidants, corrosion inhibitors and detergents. Short-chain dialkyl dithiophosphates and their sodium and ammonium salts are used as flotation agents for zinc and lead sulfide ores. The methyl and ethyl derivatives (RO)2P(S)SH and (RO)2P(S)CI are of particular interest in the large-scale manufacture of pesticides such as parathion, malathion, dimethylparathion, etc. For example parathion. which first went into production as an insecticide in Germany in 1947. is made by the following reaction sequence ... 

Cationic quaternary ammonium compounds such as distearyldimethylammonium-chloride (DSDMAC) used as a softener and as an antistatic, form hydrated particles in a dispersed phase having a similar structure to that of the multilayered liposomes or vesicles of phospholipids 77,79). This liposome-like structure could be made visible by electron microscopy using the freeze-fracture replica technique as shown by Okumura et al. 79). The concentric circles observed should be bimolecular lamellar layers with the sandwiched parts being the entrapped water. In addition, the longest spacings of the small angle X-ray diffraction pattern can be attributed to the inter-lamellar distances. These liposome structures are formed by the hydrated detergent not only in the gel state but also at relatively low concentrations. 

When ammonium lauryl sulfate is reacted with ethylene oxide, the result is the larger molecule ammonium laureth sulfate. This molecule has the same detergent and surfactant qualities, but it is larger consequently it does not penetrate the skin and hair as easily. The term laureth is actually a contraction of lauryl ether. The full name is ammonium lauryl ether sulfate. 

The most common ingredient in shampoos is also the most common detergent in use in other products a class of surfactants known as straight-chain alkyl benzene sulfonates. Examples are ammonium lauryl sulfate, its sodium relative, and the slightly larger but related molecule ammonium lauryl ether sulfate (sometimes abbreviated as ammonium laureth sulfate). 

Sodium lauryl sarcosinate is very similar to the lauryl sulfate class of detergents and surfactants. The sulfate group is replaced with the amino acid sarcosinic acid, and the ammonium group is replaced with a sodium atom. The result is a detergent that is milder on the skin and oral membranes, and can be used in toothpastes without causing irritation of the gums. 

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