Anionic surfactants ester carboxylates

The reaction product with monoethanolamine acts as a thickening agent [41,101] and with alcohols as an emollient [40]. Also reaction products with amino acids and oligo- or polypeptides for use in cosmetic formulations are known [43]. Sorbitan esters from ether carboxylates are described as emulsifiers or mild surfactants in cosmetic formulations [39] and alkyl ether carboxylic acid taurides as nonirritant anionic surfactants for cosmetic cleaners in particular [44]. Using unsaturated ether carboxylates it is possible to make viscous formulations based on combinations of unsaturated and saturated ether carboxylates [111]. Highly purified alkyl ether carboxylates based on alcohol ethoxylates with low free alcohol content have also been described [112]. 

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 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. 

Some carboxylate surfactants, such as long-chain fatty acids or their anionic esters with Coenzyme A, are precipitated in the presence ( fCSmd M + (Constantinides and Steim, 1986). Measurements of CMC in the presence of divalent ions should be avoided since the insoluble surfactant could introduce serious artifacts. Traces of transition-metal ions can catalyze autooxidation of some polyoxyethylene surfactants. In a recent article by Xiao (Xiao, 2006), interactions between anionic surfactant (SDS) micellar solutions and several familiar metal salt solutio b. 

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. 

Acyl Isethionates are ester-type anionic surfactants formed by monocarboxylic acids and isethionic acid HOCH2CH2SO3H. The latter is formed by reaction of 30 % aqueous sodium bisulphite and ethylene oxide at 70 C [66]. All commercial isethionates (as sodium cocoyl isethionate) are esters derived from natural carboxylic acids by esterification of the acids or acyl chlorides with sodium isethionate ... 

The kinetics of 2,4-dinitrophenyl-acetate hydrolysis catalyzed by polymers containing imidazole, carboxylic acid, oxidation groups and their complexes with surfactants, such as 1-cetylpyridinium chloride and cetylundecyldimethylammonium bromide, was determined by spectrophotometry [57]. Catalytic rate constants of the second-order-rate increase with a rise in the surfactant concentration until they reach a plateau at a polymer/surfactant ratio of 1 6. Anionic surfactant does not accelerate the polymer-catalyzed hydrolysis. The catalytic mechanism of a polymer/surfactant complex enables the penetration of the substrate into a pseudophase of a soluble complex. This leads to an increase of the ester concentration in the neighbourhood of a polymer imidazole fragment and accelerates the process. Such a pseudophase promotes the protonation of imidazole rings. 

ANIONIC SURFACTANTS Carboxylic acid salts Sulfonic acid salts Sulfuric acid ester salts Phosphoric and polyphosphoric acid esters Perfluorinated anionics... 

Structurally, amino acid-based surfactants may be depicted as shown nearby. The fundamental stmctures may be considered as (1) N-acylated amino acid, which is essentially an anionic surfactant, or modified as in (b), where the carboxylic group is converted to ester or amide, as seen in cationic surfactants. The structures in (c) and (d) represent those of amphoteric surfactants, in which both amino and carboxyl groups represent hydrophilic moieties. 

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... 

Nonionic surfactants are amphiphilic compounds the lyophilic (in particular hydrophilic) part of which does not dissociate into ions and hence has no charge. However, there are nonionics, for example such as tertiary amine oxides, which are able to acquire a charge depending on the pH value. Even polyethers, such as polyethylene oxides, are protonated under acidic conditions and exist in cationic form. Long-chain carboxylic acids are nonionic under neutral and acidic conditions whereas they are anionics under basic conditions. So, the more accurate definition is as follows nonionics are surfactants that have no charge in the predominant working range of pH. The main part of nonionics can be classified into alcohols, polyethers, esters, or their combinations. 

Sulfur in oxidation state IV can be used to produce a variety of anionic snUbnates, as depicted in Scheme 1.5. Sodium bisulfite can be used to prepare sulfonates of a,b-unsaturated acids and esters, such as those prepared from maleic anhydride. The mechanism involves Michael addition to the activated double bond by the more nucleophilic sulfur atom, and is conducted in an aqueous two-phase system where, for example, a maleate half acid ester or diester is dispersed and heated under narrowly controlled pH conditions to minimize ester hydrolysis and avoid competitive hydroxide addition to the double bond. The resulting classes of surfactants include sulfosuccinates (which are in fact carboxylate sulfonate disalt surfactants) prepared from the maleic half acid esters of fatty alcohols or alcohol ethoxylates. Diesters of maleic are sulfonated by the same type of process to produce surfactants such as the ubiquitous dioctyl sulfosuccinate (DOSS) from the diester of 2-ethylhexyl alcohol and maleic anhydride. 

Van Os, N.M., Haak, J.R., Rupert, L.M.A. (Eds.) Physico-Chemical Properties of Selected Anionic, Cationic and Nonionic Surfactants, Elsevier Amsterdam, 1993. Iglesias, E. Ethyl cyclohexanone-2-carboxylate in aqueous micellar solutions. 1. Ester hydrolysis in cationic and nonionic micelles. J. Phys. Chem. B2001,105(42), 10287-10294. 

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