Anionic surfactants derivatives

Evidence presented thus far for the putative role played by the photoliberated surfactants has been somewhat circumstantial. Conventional infrared and ultraviolet spectroscopy establish that the photolabile protecting group is photolyzed and the surfactant released under photolysis acid-base indicators, when added to the photosensitive coating, confirm the release of acid for the anionic surfactant derivatives. The surface sensitive spectroscopic techniques of ESCA (Electron Spectroscopy for Chemical Analysis) and RAIR (Reflection-Absorption Infrared) spectroscopy establish the involvement of the surfactant more unequivocally. 

The glycosylating L-iduronic acid derivatives 4 and 5 proved to be equally effective as donors and were much better than the corresponding 5-ethyl or 5-phenyl thioglycosides or glycosyl fluorides. The uronosides 6 and 7, which are anionic surfactants derived from glucose, are inhibitors of HIV. ... 

Anionic surfactants with the general structure RpCONH-X-COONa (e.g., X = -(0112)5-) have been reported in the patent literature. These surfactants are synthesized from the corresponding isopropyl ester and 6-amino-hexanoic acid sodium or ammonium salt (H2N(CH2) 5COOM). Another class of anionic surfactants derived from PFCA derivatives are perfluoroacylbenzenesulfo-nates (Scheme 18.11). This group of surfactants is synthesized by Friedel-Crafts acylation of benzene with a PFCA halide (e.g., perfluorooctanoyl chloride) in the presence of at least one equivalent of a Lewis acid (e.g., anhydrous aluminum chloride). This reaction proceeds smoothly and in good yields at subambient or ambient temperatures. The perfluoroacylbenzene is sulfonated with oleum or sulfur trioxide and neutralized with a base (e.g., sodium hydroxide). 

Field, J. A., J. A. Leenheer, K. A. Thom, L. B. Barber, II, C. Rostad, D. L. Macalady, S. R. Daniel, Persistent anionic surfactant-derived chemicals in. sewage effluent and groundwater,/. Contam. HydroL, 1992,9,55-78. 

A selection of important anionic surfactants is displayed in table C2.3.1. Carboxylic acid salts or tire soaps are tire best known anionic surfactants. These materials were originally derived from animal fats by saponification. The ionized carboxyl group provides tire anionic charge. Examples witlr hydrocarbon chains of fewer tlran ten carbon atoms are too soluble and tliose witlr chains longer tlran 20 carbon atoms are too insoluble to be useful in aqueous applications. They may be prepared witlr cations otlrer tlran sodium. 

Lignites and lignosulfonates can act as o/w emulsifiers, but generally are added for other purposes. Various anionic surfactants, including alkylarylsulfonates and alkylaryl sulfates and poly(ethylene oxide) derivatives of fatty acids, esters, and others, are used. Very Httle oil is added to water-base muds in use offshore for environmental reasons. A nonionic poly(ethylene oxide) derivative of nonylphenol [9016-45-9] is used in calcium-treated muds (126). 

Ethoxylation of alkyl amine ethoxylates is an economical route to obtain the variety of properties required by numerous and sometimes smaH-volume industrial uses of cationic surfactants. Commercial amine ethoxylates shown in Tables 27 and 28 are derived from linear alkyl amines, ahphatic /-alkyl amines, and rosin (dehydroabietyl) amines. Despite the variety of chemical stmctures, the amine ethoxylates tend to have similar properties. In general, they are yellow or amber Hquids or yellowish low melting soHds. Specific gravity at room temperature ranges from 0.9 to 1.15, and they are soluble in acidic media. Higher ethoxylation promotes solubiUty in neutral and alkaline media. The lower ethoxylates form insoluble salts with fatty acids and other anionic surfactants. Salts of higher ethoxylates are soluble, however. Oil solubiUty decreases with increasing ethylene oxide content but many ethoxylates with a fairly even hydrophilic—hydrophobic balance show appreciable oil solubiUty and are used as solutes in the oil phase. 

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. 

Surface-active compounds, especially the anionic surfactants, are derived from fossil raw materials as well as from recent raw materials. The portion of the biomass on the production of anionic surfactants is about 75% if the soap, the quantitatively most important anionic surfactant, is included. Considering only the synthetic surfactants, the syndets, the portion of fossil raw materials in the production of these surfactants, is about 75%. Without the lignosulfonates (and the petroleum sulfonates) this portion is about 90%. Due to strong efforts... 

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. 

Many other products can be used as softeners but are less important commercially because of greater cost and/or inferior properties. Examples are anionic surfactants such as long-chain (C16-C22) alkyl sulphates, sulphonates, sulphosuccinates and soaps. These have rather low substantivity and are easily washed out. Nonionic types of limited substantivity and durability, usually applied by padding, include polyethoxylated derivatives of long-chain alcohols, acids, glycerides, oils and waxes. They are useful where ionic surfactants would pose compatibility problems and they exhibit useful antistatic properties, but they are more frequently used as lubricants in combination with other softeners, particularly the cationics. 

At the end of the 1990s statistics show that the non-ionic surfactants achieved the highest growth in production rates world-wide, though anionic surfactants (anionics) maintained the dominant position in the surfactant market. Today they are produced in a larger variety by the petrochemical industry than all other types of surfactants. Their production spectrum covers alkyl sulfates (ASs), secondary alkane sulfonates (SASs) and aryl sulfonates and carboxylates via derivatives of partly fluorinated or perfluorinated alkyl surfactants to compounds with an alkylpolyglycolether substructure combined with an anionic moiety such as alkylether sulfates (AESs), phosphates, phosphonates or carboxylates. 

While APEO cannot be ionised successfully under negative conditions and consequently for identification MS-MS(—) is not informative, the identification of all anionic APEO derivatives is possible in the negative ionisation mode. For some derivatives, negative as well as positive ionisation can be applied. The loss of the anionic moiety, however, must be taken into account if ionisation is performed in the positive mode. Di-NPEC surfactant homologues submitted to negative CID resulted in the prominent di-alkyl-phenolate ion at m/z 345 (Fig. 2.11.18(a) as shown with the homologue m/z 799 under CID conditions). Therefore, the application of the parent ion scan of m/z 345 in the negative ESI and APCI-FIA-MS-MS mode is very specific for the detection of all anionic derivatives of di-NPEO comparable in... 

Fluorinated phosphinic and phosphonic acid derivatives Perfluoro derivatives of alkyl phosphonic acid CnF2n+1-P(0)(0H)2 and alkyl phosphinic acid CnF2n+i(CmF2m+1)-P(0)0H (n = m or n m) shown with their general structural formulae in Fig. 2.11.29(1) and (II) were examined by negative ESI- and APCI-FIA-MS. These anionic surfactant compounds contained perfluoro alkyl chains [2,22,25]. By analogy with their behaviour in the TSI-FIA-MS(—) process [25], the phosphonic acid formed [M — H] ions at m/z 399 and 499... 

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