Anionic surfactants phosphate esters

Tr i ton QS-44 Surfactant Phosphate ester, acid form, anionic (80% active) Union Carb... 

Inspired by the many hydrolytically-active metallo enzymes encountered in nature, extensive studies have been performed on so-called metallo micelles. These investigations usually focus on mixed micelles of a common surfactant together with a special chelating surfactant that exhibits a high affinity for transition-metal ions. These aggregates can have remarkable catalytic effects on the hydrolysis of activated carboxylic acid esters, phosphate esters and amides. In these reactions the exact role of the metal ion is not clear and may vary from one system to another. However, there are strong indications that the major function of the metal ion is the coordination of hydroxide anion in the Stem region of the micelle where it is in the proximity of the micelle-bound substrate. The first report of catalysis of a hydrolysis reaction by me tall omi cell es stems from 1978. In the years that... 

Cationic, anionic, and amphoteric surfactants derive thek water solubiUty from thek ionic charge, whereas the nonionic hydrophile derives its water solubihty from highly polar terminal hydroxyl groups. Cationic surfactants perform well in polar substrates like styrenics and polyurethane. Examples of cationic surfactants ate quaternary ammonium chlorides, quaternary ammonium methosulfates, and quaternary ammonium nitrates (see QuARTERNARY AMMONIUM compounds). Anionic surfactants work well in PVC and styrenics. Examples of anionic surfactants ate fatty phosphate esters and alkyl sulfonates. 

Ether carboxylates are used not only in powdered detergents but in liquid laundry detergents for their hard water stability, lime soap dispersibility, and electrolyte stability they improve the suspension stability and rheology of the electrolyte builder [130,131]. Formulations based particularly on lauryl ether carboxylate + 4.5 EO combined with fatty acid salt and other anionic surfactants are described [132], sometimes in combination with quaternary compounds as softeners [133,163]. Ether carboxylates show improved cleaning properties as suds-controlling agents in formulations with ethoxylated alkylphenol or fatty alcohol, alkyl phosphate esters or alkoxylate phosphate esters, and water-soluble builders [134]. 

The development of monoalkyl phosphate as a low-skin-irritating anionic surfactant is accented in a review with 30 references on monoalkyl phosphate salts, including surface-active properties, cutaneous effects, and applications to paste- and liquid-type skin cleansers, and also on phosphorylation reactions from the viewpoint of industrial production [26]. The preparation and industrial applications of phosphate esters as anionic surfactants were discussed [27]. 

A review of the preparation, properties, the uses of surface-active anionic phosphate esters prepared by the reactions of alcohols or ethoxylates with tetra-phosphoric acid or P4O10 is given in Ref. 3. The preparation and industrial applications of phosphate esters as anionic surfactants were also discussed in Ref. 31. 

In order to obtain anionic polyoxyethylene phosphate surfactants, either the terminal hydroxy group of a polyoxyethylated hydrophobic substance is reacted with a phosphorylating agent or a phosphate ester is oxalkylated. Most often aliphatic and aliphatic-aromatic alcohols are first treated with an alkylene oxide and afterward with one of the phosphorylating agents, such as P4OI0, POCl3, phosphoric acid, or polyphosphoric acid [39-48]. 

Solubilizing activity are also used in enhanced oil recovery. Tar and extremely viscous hydrocarbons are recovered by the injection of an aqueous solution of an anionic orthophosphate ester surfactant into a petroleum formation, retaining the surfactant in the formation for about 24 h, and displacing the solubilized hydrocarbons toward a recovery well. The surfactant forms an oil microemulsion with the hydrocarbons in the formation. An anionic monoorthophosphate ester surfactant which is a free acid of an organic phosphate ester was dissolved in water. The input of surfactant solution was 2-25% of the pore volume of the formation [250]. To produce a concentrate for the manufacture... 

The development of monoalkyl phosphate as a low skin irritating anionic surfactant is accented in a review with 30 references on monoalkyl phosphate salts, including surface-active properties, cutaneous effects, and applications to paste and liquid-type skin cleansers, and also phosphorylation reactions from the viewpoint of industrial production [26]. Amine salts of acrylate ester polymers, which are physiologically acceptable and useful as surfactants, are prepared by transesterification of alkyl acrylate polymers with 4-morpholinethanol or the alkanolamines and fatty alcohols or alkoxylated alkylphenols, and neutralizing with carboxylic or phosphoric acid. The polymer salt was used as an emulsifying agent for oils and waxes [70]. Preparation of pharmaceutical liposomes with surfactants derived from phosphoric acid is described in [279]. Lipid bilayer vesicles comprise an anionic or zwitterionic surfactant which when dispersed in H20 at a temperature above the phase transition temperature is in a micellar phase and a second lipid which is a single-chain fatty acid, fatty acid ester, or fatty alcohol which is in an emulsion phase, and cholesterol or a derivative. 

Phosphate esters (9.20) represent a different class of hydrophile-characterised anionic surfactants mono- or di-esters can be formed depending on whether one or two alkyl groups are present. Most phosphate esters are based on alcohols and especially their ethoxylates,... 

A wide range of anionic surfactants (Fig. 23) has been classified into groups, including alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), alcohol sulfates (AS), alcohol ether sulfates (AES), alkyl phenol ether sulfates (APES), fatty acid amide ether sulfates (FAES), alpha-olefin sulfates (AOS), paraffin sulfonates, alpha sulfonated fatty acids and esters, sulfonated fatty acids and esters, mono- and di-ester sulfosuccinates, sulfosuccinamates, petroleum sulfonates, phosphate esters, and ligno-sulfonates. Of the anionic surfactants, ABS and LAS continue to be the major products of anionic surfactants [314, 324]. Anionic surfactants have been extensively monitored and characterized in various environmental matrices [34,35,45,325-329]. 

The major subgroups of anionic surfactants include the alkali carboxylates (soaps), sulfates, sulfonates, and to a smaller degree, phosphates. The esterification of alcohol with sulfuric acid yields probably the best-studied surfactant, sodium dodecylsulfate or SDS. SDS, a sulfate ester, is an extremely effective emulsifier because of its high-electrostatic repulsion. Other sulfates are, for example, sulfated esters from fatty acids, sulfated ethers, and sulfated fats and oils. Sulfonates stem from the reaction of sulfonic acid with suitable substrates. Members of the class of sulfonates are, for example, sulfonic acid salts or aliphatic sulfonates. Other anionic surfactants include substances such as carboxylated soaps and esters of phosphoric acid. 

Monoalkyl phosphate and phosphate esters are special types of phosphoms-contain-ing anionic surfactants that are of great industrial importance. They are used for flameproofing, as antistatic for textiles, for foam inhibition, as an extreme pressure (EP) lubricant additive, as a surfactant component for alkaline, and as acid cleaners and for special cosmetic preparations (5). The commercially available phosphate ester products are complex mixtures of monoester and diester, free phosphoric acid, and free nonionic. 

The resulting product is a mixture of dialkyl and monoalkyl phosphate esters. These products also contain small amounts of condensed phosphates and phosphoric acid. Neutralization of the acids with bases like alkali hydroxides, ammonia, or amines produces water-soluble anionic surfactants and emulsifiers. 

Monoalkyl phosphates inhibit the foam generation of other anionic and nonionic surfactants. The composition of the phosphate ester greatly affects the functional properties of the product. 

The formation of foam during the automatic dishwashing cycle is detrimental to the mechanical washing efficiency of the machine. To prevent foaming, LADD products often contain defoamers. The most commonly used hypochlorite-stable defoamers in LADDs are anionic surfactants such as alkyl phosphate esters and ethoxylated esters [41-43] and silicone oils [44], The structures of the first two types are shown in Figure 9.5. Also described in the patent literature is the use of aliphatic alcohols or acids as defoamers [45],... 

Chem. Descrip. Aromatic acid phosphate ester Uses Surfactant lubricant antirust antistat good emulsification detergency pigment dispersant polymerization emulsifier Features Acid and alkali resist. sol. to high cone, electrolyte Iiq. Properties Transparent Iiq. sp.gr. 1.11 pH 2.0 (3% aq.) anionic 100% solids... 

Definition Sodium salt of a complex mixture of phosphate esters of laureth-4 Properties Anionic Toxicoiogy TSCA listed Uses Emulsifier, surfactant for cosmetics detergent for household and industrial applies. textile antistat, lubricant, emulsifier vise, builder for creams and lotions polymerization and stabilization of latexes Trade Name Synonyms Chemphos TR-510S t[Chemron http //www.chemron.com]-, Rhodafac MC-470 [Rhodia HPCII http //WWW. rhodia-hpeii. com]... 

Long-chain alcohols, as well as traces of water in the alcohol or from P4O10, lead to a higher proportion of monoalkyl esters. Alkyl phosphates are described as being low-skin-irritant anionic surfactants, and are used in paste- and liquid-type skin cleansers. However, there are also some specific routes for the syntheses of defined primary or secondary esters. 

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