J. K. Weil

Soap based detergent formulations. V. Amphoteric lime soap dispersing agents

A series of amphoteric surfactants was prepared by the reaction of 1,3-propanesultone with fat derived primary amines, N-methylalkylamines, N,N-dimethylalkylamines, and N-acyl-N′,N′-dimethyl-1,3-propanediamines. Both mono- and disulfopropylated derivatives of the primary amines were synthesized. All compounds were found to be excellent lime soap dispersing agents. The quaternary sulfobetaines were found to possess the best detergency properties both by themselves and when formulated with tallow soap with or without sodium silicate builder. The detergency performance of such formulations is ca. the same as that of a commercial phosphate-built detergent.

Long chain alkanesulfonates and 1-hydroxy-2-alkanesulfonates: Structure and property relations

Even chain sodium alkanesulfonates from the Strecker reaction, odd chain sodium alkanesulfonates from the alkaline decarboxylation of α-sulfo acids, and sodium 1-hydroxy-2-alkanesulfonates from the reduction of esters of α-sulfo acids were compared with respect to Krafft point, critical micelle concentration, detergency and foam height. Sodium alkanesulfonates and crude fusion products from the α-sulfo acids (mixtures of alkanesulfonates of one less carbon atom with a lesser amount of a soap of two less carbon atoms) are more soluble and have better detergent and foaming properties. Sodium 1-hydroxy-2-alkanesulfonates resemble monosodium salts of α-sulfo acids.Alkanesulfonic acids and 1-hydroxy-2-alkane-sulfonic acids obtained from the sodium salts by ion exchange have lower Krafft points and are more readily soluble. The critical micelle concentrations of 1-hydroxy-2-alkanesulfonic acids and α-sulfo acids are nearly the same and about equal to those of alkanesulfonic acids of one less carbon atom.

Sodium salts of alkyl esters ofa-sulfo fatty acids. Wetting, lime soap dispersion, and related properties

A series of esters of the general formula RCH(SO3Na)-CO2R′ of 14–19 carbon atoms prepared by the α-sulfonation of propionic, butyric, pelargonic, lauric, myristic, palmitie, and stearic acids and esterification with normal primary alcohols were compared for critical micelle concentration, surface and interfacial tension, Ca++ stability, wetting properties, foam height, detergency, and lime soap dispersing properties. Comparison of position isomers showed that as the hydrophilic portion moved from the center toward either end, cmc and wetting efficiency decreased, surface and interfacial tension increased, and Ca++ stability and lime soap dispersing properties improved.A coconut oil fatty acid forerun sulfonated with SO3 vapor and esterified with 2-ethylhexanol gave a product with useful wetting properties in soft and hard water.

Soap-based detergent formulations I. Comparison of soap-lime soap dispersing agent formulations with phosphate built detergents

Blends of soap with small amounts of lime soap dispersing agents are efficient detergents in hard water and require little or no tripolyphosphate builder. Lime soap dispersing agents examined include sulfated ethoxylated fatty alcohols, sulfated N-(2-hydroxyethyl) fatty amides, methyl esters of α-sulfo fatty acids, 2-sulfoethyl fatty acid esters and N-methyl-N-(2-sulfoethyl) fatty amides as well as nonionics derived from tallow alcohols. Detergency evaluations were carried out with three commercial soiled cotton cloths as well as by a laboratory multi-wash technique. Formulations containing 80% soap, 10% lime soap dispersing agent and 10% builder gave optimum detergency values. Builder effectiveness was rated tripolyphosphate>silicate (1:1.6)> metasilicate = citrate = oxydiacetate = nitrilotriacetate>carbonate≫sulfate. The detergency of soap-lime soap dispersed combinations compared favorably with a standard brand household heavy duty granular detergent in 50, 150 and 300 ppm hardness water on three soiled cloths.

Disodium 2-sulfohexadecyl and 2-sulfoɆctadecyl sulfates

Disodium 2-sulfoalkyl sulfates RCH (SO3Na) CH2OSO3Na were prepared from esters ofa-sulfo acids by metal borohydride reduction of the ester group to a primary alcohol, and subsequent sulfation. Disodium 2-sulfoöctadecyl sulfate resembles disodium 2-sulfoethyla-sulfostearate in general structure and properties, particularly in the fact that both are excellent lime soap dispersing agents.

Synthetic detergents from animal fats. Disodium alpha-sulfopalmitate and sodium oleyl sulfate

SummaryDisodium α-sulfopalmitate and homologous compounds were prepared by sulfonation of the fat acid with liquid sulfur trioxide. Sodium oleyl sulfate was prepared in an estimated 95% purity by sulfation of oleyl alcohol with pyridine-sulfur trioxide. The solubility, surface tension, wetting, foaming, and detergent properties of these and related compounds were measured.Disodium α-sulfopalmitate is potentially inexpensive, has adequate surface active properties, is a good detergent in hard and soft water, but has limited solubility at room temperature (0.25% at 25°C.). The lauric and myristic homologs are less surface active, but more soluble. Disodium α-sulfostearate is less soluble.Sodium oleyl sulfate has excellent solubility, and surface active properties and is an excellent detergent in soft water. It is not quite so efficient in hard water although no insoluble calcium salts are formed.The future of the two compounds will depend upon successful formulation with builders or combinations with soap or other detergents.

Synthetic detergents from animal fats. X. Sulfated, ethenoxylated tallow alcohols

SummarySulfated ethenoxylated tallow alcohols of average composition corresponding to the formulas C16H33(OC2H4)2OSO3Na, C18H37(OC2H4)2OSO3Na, and C18H37(OC2H4)10OSO3Na, were prepared by ethenoxylation and sulfation of hexadecanol and octadecanol.The incorporation of two ethenoxy groups improved solubility without loss in detergency compared to the corresponding sodium hexadecyl and octadecyl sulfates. With consideration also of economy in the number of ethenoxy groups, two appear to be near the optimum. The product with 10 ethenoxy groups was an even more readily soluble but less effective detergent.Of the sulfated ethenoxylated tallow alcohols, sodium hexadecyloxyethoxyethyl sulfate [C16H33(OC2H4)2OSO3Na] had the lowest surface-tension and the best foaming properties; sodium octadecyloxyethoxyethyl sulfate [C18H37(OC2H4)2OSO3Na] was the best emulsifying agent; and the product with 10 ethenoxy groups [C18H37(OC2H4)10OSO3Na] had the greatest stability in regard to metallic ions and to acid hydrolysis.All three were excellent lime-soap dispersing agents with good or excellent emulsifying properties and stability in regard to metallic ions.

Sodium alkyl α-sulfopelargonates, C7H15CH(SO3Na)CO2R. Wetting and related properties

A series of sodium alkyl α-sulfopelargonates prepared from sodium α-sulfopelargonic acid and alcohols of from 2 to 12 carbon atoms were examined for surface active properties. Esters with the hydrophilic portion in the middle of the molecule, as in sodium hexyl, heptyl octyl, capryl (or 2-octyl) and 2-ethylhexyl α-sulfopelargonate were very efficient wetting agents with good foaming properties and a c.m.c. of from 2 to 7 millimoles per liter. The presence of the α-sulfo group inhibits hydrolysis of the ester linkage, apparently by steric hindrance. Sodium capryl α-sulfopelargonate, an ester of a secondary alcohol, was particularly stable to acid and alkaline hydrolysis. The esters are easily soluble in water, organic solvents and mineral oil.

The a-sulfonation of pelargonic, stearic, and substituted stearic acids

Direct sulfonation of higher fatty acids with sulfur trioxide or chlorosulfonic acid, without use of solvent, is possible, but the product must then be isolated as the sodium salt. Use of a chlorinated solvent permits isolation of the α-sulfo acid. Sulfonation with dioxane sulfur trioxide in place of sulfur trioxide gave a nearly colorless α-sulfostearic acid.Substituted stearic acids derived from oleic or elaidic acids (phenyl-, 9,10-dichloro-, and 9,10-dihydroxystearic acids) were α-sulfonated with dioxane sulfur trioxide. Solubility, detergent, and surface-active properties were examined and related to structure.The surface-active properties of sodium α-sulfopelargonic acid are not very evident, but the octyl ester, with a much lower critical micelle concentration (0.08% compared to 1.00%), was found to be a very efficient wetting agent.

Arylstearic acids from oleic acid. Variables affecting the yield and properties

SummaryTwenty-six aromatic compounds were compared in the synthesis of arylstearic acids from oleic acid by the Friedel and Crafts reaction. Xylylstearic acid was the arylstearic acid obtained in the highest yield (92.4%) from technical m-xylene and commerical oleic acid. The various side reactions are disussed including the possible conversion of oleic acid into products which on vacuum distillation of the crude arylstearic acid appear as a forerun and as a still residue. Oleic acid of about 98% purity did not improve the yield but resulted in nearly colorless, rather than yellow viscous oils.Crystalline arylstearic acids have for first time been isolated from the reaction products but only in small yields.