Soap-based detergent formulations: XVIII. Effect of structure variations on surface-active properties of sulfur containing amphoteric surfactants

Quaternary ammonium amphoteric surfactants have been found in the past to be excellent lime soap dispersing agents and detergents but exhibit unusual solubility behavior. In search of a relationship between chemical structure and surface-active properties, compounds having the following general formula were synthesized: ZN⁺(CH₃)₂(CH₂)_nX⁻, where Z is C₁₂H₂₅-, C₁₄H₂₉-, C₁₆H₃₃-, or C₁₅H₃₁CONHC₃H₆-, n is 2, 3, or 4 and X is SO₃- or OSO₃-. Tertiary amines were converted to sulfobetaines (X=SO₃-) by reaction with (a) butanesultone (n=4), (b) propanesultone (n=3), or (c) sodium 2-bromoethanesulfonate (n=2). An alternate synthesis for the sulfoethylbetaines (n=2) involved the reaction of the tertiary amines with ethylene bromide, followed by treatment with sodium sulfite. All sulfated quaternary ammonium compounds (X=OSO₃-) were synthesized by treatment of the tertiary amine with the appropriate chloroalcohol, followed by sulfation with chlorosulfonic acid. The sulfated quaternary ammonium amphoterics are stable to acid hydrolysis, and alkaline stability improves with increasing bridge chain length. Sulfoethyl amphoterics are less water soluble than sulfobutyl, which in turn are less soluble than sulfopropyl derivatives of the same alkyl chain length. For the most part, the sulfated amphoterics are insoluble but are solubilized by soap. The lime soap dispersing properties improve as the carbon chain bridge length increases for both the sulfates and sulfonates. Formulations of tallow soap, amphoteric surfactant, and sodium silicates gave good detergency in most cases. Presented at the AOCS meeting, Dallas, April 1975.     

Soap-based detergent formulations: XVII. Synthesis and surface active properties of alkylbenzene derived amine oxides

Amine oxides C_nH_2n+1C₆H₄SO₂NH(CH₂)₃-NMe₂—O⁻ were prepared for testing as lime soap dispersing agents in phosphate free, soap-based, sodium silicate built laundry detergents. These amine oxides were synthesized via a three step route from a variety of pure 1-phenylalkanes and also from a commerical detergent alkylate mixture. The process included (a) the sulfonation of the phenylalkane with chlorosulfonic acid, (b) reaction of the resulting alkarylsulfonyl chloride with H₂N(CH₂)₃NMe₂ or with H₂N(CH₂)₃N(CH₂CH₂OH)₂ under anhydrous conditions, and (c) oxidation with aqueous H₂O₂. The amine oxides were water soluble and in some instances isolable as crystalline hydrates. They were found to be thermally stable below 125 C and highly surface active. Optimum detergency and lime soap dispersability were achieved by the model compound of alkyl chain length n=8. This was in contrast to the behavior of the related amphoteric sulfobetaine series C_nH_2n+1C₆H₄SO₂NH(CH₂)₃NMe₂(CH₂)₃-SO₃ ⁻, whose optimum detergency and lime soap dispersability previously had been observed to reach a maximum at chain length n=12. Detergency screening tests showed that soap-based detergents formulated with the sulfobetaines outperformed the ones formulated with the amine oxides. Presented at the AOCS Meeting, Dallas, April 1975.     

Soap-based detergent formulations: II. Oxyethylated fatty amides as lime soap dispersing agents

Nonionic surface active agents with two oxyalkyl chains were prepared from the triethylamine catalyzed reaction of ethylene oxide with diethanolamides of palmitic, stearic and tallow fatty acids. The addition of 4 moles of ethylene oxide was required to render these diethanolamides water soluble, whereas 9 moles were required to make the corresponding monoethanolamide soluble. Efficiency of lime soap dispersion increased as oxyethyl chain length was increased. Best detergency of soap-nonionic combinations was achieved when the oxyethyl chain length was at the minimum required for water solubility. Theγ-hydroxyethanolamides and -diethanolamides were prepared by the uncatalyzed reaction of the corresponding amines withγ-stearolactone. These compounds became water soluble at lower levels of oxyethylation, but the lime soap dispersing power and detergency were not improved over those of corresponding compounds derived from stearic acid. Presented at the AOCS Meeting, Los Angeles, April 1972. E. Market. Nutr. Res. Div., ARS, USDA.     

Synthesis and Surface Active Properties of tri[(N‐alkyl‐N‐ethyl‐N‐Sodium carboxymethyl)‐2‐Ammonium bromide ethylene] Amines

Trimeric betaine surfactants tri[(N‐alkyl‐N‐ethyl‐N‐sodium carboxymethyl)‐2‐ammonium bromide ethylene] amines were prepared with raw materials containing tris(2‐aminoethyl) amine, alkyloyl chloride, lithium aluminium hydride, sodium chloroacetate, and bromoethane by alkylation, Hoffman degradation reaction, carboxymethylation and quaternary amination reaction. The chemical structures of the prepared compounds were confirmed by FTIR, ¹H NMR, MS and elemental analysis. With the increasing length of the carbon chain, the values of their critical micelle concentration initially decreased. Surface active properties of these compounds were superior to general carboxylate surfactants C₁₀H₂₁CHN⁺(CH₃)₂COONa. The minimum cross‐sectional area per surfactant molecule (A_min), standard Gibbs free energy adsorption (ΔG_ads) and standard Gibbs free energy micellization (ΔG_mic) are notably influenced by the chain length n, and the trimeric betaine surfactants have greater ability to adsorb at the air/water interface than form micelles in solution. The efficiency of adsorption at the water/air interface (pC₂₀) of these surfactants increased with the increasing length of the alkyl chain. Their foaming properties, wetting ability of a felt chip, and lime‐soap dispersing ability were also investigated.     

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. Presented at the fall meeting, American Oil Chemists' Society, Chicago, October 30–November 1, 1961. Eastern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.     

Performance characteristics of sucrose ester detergents

Standard heavy duty household laundering formulations were prepared from a series of well-characterized sucrose ester surfactants. The detergency and redeposition performance of these formulations was measured by the soil accumulation method, using for comparison standard formulations based on sulfated and sulfonated surfactants. Also measured were the lime soap dispersing power, and the tendency to leave residual adsorbed deposits on the fabric. The sucrose ester series as a whole performed at least as well in detergency as the standard anionics, and retained their effectiveness at lower concentrations. They showed about the same, or slightly less, tendency than the anionic controls to build up organic residues on the fabric, both series being much superior to soap in this respect. In redeposition performance and lime soap dispersion the sucrose esters were outstandingly better than any of the standard anionic controls. Within the sucrose ester series, the C₁₈ esters gave generally better performance than the shorter chain esters, and the saturated esters tended to be better than the unsaturated.     

A redox poly(ionic liquid) hydrogel: Facile method of synthesis and electrochemical sensing

In this article, a redox-responsive poly(ionic liquid) (redox-PIL) hydrogel Poly(1-vinyl-3-propionate imidazole phenothiazine sulfonic acid)-chitosan [Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻)-CS] was produced by using chitosan (CS) crosslinking with redox-PIL Poly(1-vinyl-3-propionate imidazole phenothiazine sulfonic acid [Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻)]. The incorporation of redox-active counter anions 3-(phenothiazine-10-yl) propane 1-sulfonic acid anions (PTZ-(CH₂)₃SO₃⁻) into cationic PIL-polyimidazole rendered Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻) with electron catalytic ability, ionic conductivity, and electron conductivity. Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻)-CS combines the properties of hydrogel and redox-PIL, thus offering intrinsic porous conducting frameworks and promoting the transport of charges, ions, and molecules, leading hydrogel with excellent electrochemical properties. The crosslinking occurrence of Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻) and CS resulting from the synthetic process of hydrogel was verified by differential scanning calorimetry and thermogravimetric analysis. A three-dimensional polymer network hydrogel with good biocompatibility and permeability was formed after crosslinking. In addition, only 64% weight loss within 600 °C was observed in Poly(VPI⁺PTZ-(CH₂)₃SO₃⁻)-CS representing its thermally stable performance. When used as an electrochemical sensor, the hydrogel-modified gold electrode improved the electrocatalytic oxidation of cysteine. Differential pulse voltammetry results indicated that the detection range was from 5 × 10⁻⁸ to 5 × 10⁻³ M and the limit of detection was 6.64 × 10⁻⁸ M. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136, 48051.     

How the Influence of Different Salts on Interfacial Properties of Surfactant–Oil–Water Systems at Optimum Formulation Matches the Hofmeister Series Ranking

In this work, we present the effects of salts on sodium dodecyl benzene sulfonate micellization and on the interfacial performance of a sodium dodecyl benzene sulfonate–heptane–brine system at optimum formulation, i.e., hydrophilic–lipophilic deviation (HLD) = 0. In order to do that, interfacial tension and dilational interfacial rheology properties of surfactant–heptane–water systems at optimum formulation are measured using an interfacial spinning drop tensiometer with an oscillating velocity, which can accurately measure interfacial rheology properties at both low and ultralow interfacial tensions. The brines used contain one of the following salts: MgCl₂, CaCl₂, NaCl, NH₄Cl, NaNO₃, CH₃COONa, or Na₂SO₄. We performed a one-dimensional salinity scan with each of these salts to achieve an optimum formulation. In relation to the Hofmeister series, we found that, at optimum formulation, systems with chaotropic ions (NH₄⁺, NO₃⁻) present interfaces with ultralow interfacial tensions, very low dilational modulus, and a low phase angle, whereas kosmotropic ions (Mg²⁺, Ca²⁺, SO₄⁻²) generate high interfacial tension and high rigidity monolayers. Intermediate ions in the Hofmeister series (Na⁺, CH₃COO⁻, Cl⁻) present interfaces with intermediate properties. Furthermore, according to the Hofmeister series, interfaces can be respectively ordered from higher to lower rigidity for surfactant counterions Mg²⁺ > Ca²⁺ > Na⁺ > NH₄⁺ and coions SO₄²⁻ > CH₃COO^– > Cl⁻ > NO₃⁻, which correspond to a salting-out (highest rigidity) and salting-in (lowest rigidity) effect. We observed that counterions have a more significant effect on surfactant–oil–water system properties than those that act as coions.     

Soap-based detergent formulations: VI. Alkylaryl sulfonamide derivatives as lime soap dispersing agents

Alkylbenzenes, such as industrial detergent alkylates, as well as pure 1-phenylalkanes whose side chain lengths varied C₈−C₁₂, were converted into the corresponding alkylbenzenensulfonyl chlorides with chlorosulfonic acid. Surface active sulfonamides were obtained from the reaction of the sulfonyl chlorides with various low mol wt aminosulfonic acids, such as N-methyltaurine, or with aminoalkyl esters of sulfuric acid, such as 2-aminoethyl hydrogen sulfate. The hydrolytic stability of the resulting surface active sulfonamide derivatives was investigated. As expected, the sulfonates were quite resistant to acid or alkaline hydrolysis, while the sulfates were more susceptible to hydrolysis. Hydrolytic stability of the sulfonamides was compared with that of the analogous fatty acid amide sulfactants. All of the compounds were excellent lime soap dispersing agents giving Borhetty-Bergman values of 4–10. The compounds were evaluated for detergency either alone or formulated either with tallow soap or with tallow soap and sodium silicate (Na₂O/SiO₂ ratio of 1∶1.6) The derivatives of the pure hydrocarbons which gave the best overall detergency were those of 1-phenyldecane and 1-phenyldodecane, whereas those of 1-phenyloctane exhibited poor detergency. This ranking was observed when the compounds were tested alone as well as when formulated. The sulfonamide derivatives of the detergent alkylate type of alkylbenzenes exhibited excellent detergency characteristics and showed substantial potentiation of detergency when mixed with soap or with a soap-sodium silicate blend. The detergency performance of some of these formulated detergents was equal to that of a commercial household detergent used as a control.     

Counterion effects on the aqueous solution viscosity of cationic surfactants

The effect of varying counterion structure on the aqueous solution viscosity of various cationic surfactants was systematically examined for compounds of the type: CH₃(CH₂) _x N(CH₃)₃YAr. Ar = functionally substituted aryl moieties and Y = carboxylate (CO₂ ⁻), sulfinate (SO₂ ⁻) or sulfonate (SO₃ ⁻). Aqueous solution viscosity, which is assumed to be a measure of ion pair stability, is clearly affected by anion and cation structure, temperature, concentration and stoichiometry. An ortho substituent to the anionic functionality, e.g. hydroxyl, substantially increases ion pair stabilization. Ion pair stability is also enhanced by increasing the solution concentration, decreasing temperature, increasing cation/anion ratio or by increasing the alkyl (x) chain length.     

Unique Solubility of Switchable Alkyl-Amine Surfactants in Water

Because many amine surfactants are soluble in both water and CO₂ phases, they attract interest with regard to stabilizing CO₂-in-water dispersion systems. In our recent research, we find that the solubility of alkyl-amine surfactant in water can be significantly enhanced by salts, even though the salts are usually “salting-out” to other surfactants. The influence of various anions (NO₃⁻, Br⁻, Cl⁻, and SO₄²⁻) and cations (Na⁺, Ca²⁺, and Mg²⁺) on the alkyl-amine surfactants is investigated. The results are contrary to Hofmeister series and show that all the anions can enhance the solubility (salting-in) in the order of: NO₃⁻ > Br⁻ > Cl⁻ > SO₄²⁻, while the impact of the cations is insignificant. A physical–chemistry model based on the switchable property of the surfactant is proposed and well explains the experimental results. Therefore, the switchable alkyl-amine surfactants have potential to be applied under high-salinity and high-temperature conditions, for example, in enhanced oil recovery processes for a hot and salty carbonate reservoir.     

New amphoteric surfactants containing a 2-hydroxyalkyl group: IV. Performance of amphoteric surfactant/soap blends

The performance of new amphoteric surfactants,N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines (HAA) and their oxyethylated derivatives (HAA-nEO) was studied in blends with a fatty acid soap. The solubility, foaming power and fabric detergency were measured for blends of (Na-HAA or Na-HAA-nEO)/soap. Furthermore, lime soap dispersing power, toxicity to fish and biodegradability for HAA or HAA-nEO homologs were examined and evaluated. The blend of tallow soap and not less than 10% of C_12–14-Na-HAA exhibited better solubility behavior than tallow soap or tallow/coconut oil soap alone. Fabric detergency was improved by blending Na-HAA with soap. Soil deposition in Na-HAA/soap or Na-HAA/soap/Na₂CO₃ solution was measured. On the basis of the results for: (a) the measurements of redeposition; (b) interfacial tension between oil and water and (c) contact angle between oil and fabric in water, it was presumed that since Na-HAA adsorbed more or less in preference to soap on the surface of fabric in water, soil redeposition would be prevented in the Na-HAA/soap detergent solution.     

Synthesis and Properties of Alkoxyethyl β‐d‐Xylopyranoside

In order to improve the water solubility of sugar‐based surfactants, alkyl β‐d‐ xylopyranosides, novel sugar‐based surfactants, 1,2‐trans alkoxyethyl β‐d‐ xylopyranosides, with alkyl chain length n = 6–12 were stereoselectively prepared by the trichloroacetimidate method. Their properties including hydrophilic–lipophilic balance (HLB) number, water solubility, surface tension, emulsification, foamability, thermotropic liquid crystal, and hygroscopicity were investigated. The results indicated that their HLB number decreased with increase of alkyl chain, the water solubility improved since the hydrophilic oxyethene (─OCH₂CH₂─) fragment was introduced. The dissolution process was entropy driven at 25–45 °C for alkyl chain length n = 6–10. Octyloxyethyl β‐d‐ xylopyranoside had the best foaming ability. Nonyloxyethyl β‐d‐ xylopyranoside had the best foam stability and the emulsifying ability was better in toluene/water system than in rapeseed oil/water system. The surface tension of in aqueous solution dropped to 27.8 mN m^?1 at the critical micelle concentration, and it also showed the most distinct thermotropic liquid phases with cross pattern texture upon heating and the fan schlieren texture on cooling. Hexyloxyethyl β‐d‐ xylopyranoside possessed the strongest hygroscopicity. Based on the effective improvement of water solubility, the prepared alkoxyethyl β‐d‐ xylopyranosides showed excellent surface activity and are expected to develop their practical application as a class of novel sugar‐based surfactants.     

Performance of sulfoxylated fatty acid methyl esters

Sulfoxidation of fatty acid methyl esters with SO₂, O₂, and ultraviolet light of appropriate wavelength has led to the synthesis of methyl esters sulfonates or sulfoxylates known as Φ-MES because of the possible random position of SO₃ group in the alkyl chain. This work describes experimental measurements of physical properties such as solubility and viscosity of sodium Φ-MES water solutions. Amphipathic properties such as surface tension, critical micelle concentration, wetting and foaming powers were measured as well and compared to linear alkylbenzene sodium sulfonate (LAS). Finally, stability to water hardness, dishwashing test, and detergency performance were evaluated. Expectedly, these products may be used as LAS partners either in heavy-duty powders or in hand dishwashing liquids. Experimental results on Φ-MES of varying carbon number indicate that C₁₆ is the optimal carbon chain length.     

Rapid formation of methane hydrates with compact agglomeration via regulating the hydrophilic groups of nanopromoters

Gas hydrates have been endowed with great potential as the medium for natural gas storage & transportation. In this work, we prepared novel nanopromoters by grafting hydrophilic groups ( SO₃⁻,  COO⁻ and  N[CH₃]₃⁺) covalently on polystyrene nanospheres (Group@PSNS), and for the first time achieved rapid formation of methane hydrates together compact agglomeration by regulating the hydrophilic groups on the surface of nanopromoters. When  SO₃⁻@PSNS was used, methane hydrates formed rapidly but loosely in the reactor; while for  COO⁻@PSNS and  N(CH₃)₃⁺@PSNS, even the hydrate formation rate was seriously reduced, the formed hydrates agglomerated compactly in the reactor bottom. Interestingly, when both  SO₃⁻ and  COO⁻ were fixed on the nanospheres, both the hydrate growth rate and agglomeration compactness were controlled. Especially, the nanopromoter with the  SO₃⁻/ COO⁻ molar ratio of 2:1 resulted in the formation of methane hydrates with compact agglomeration morphology within 1–2 hr and with the storage capacity reaching 140–145 vol/vol.     

Synthesis of stimuli-responsive ionic cyclopolymers in search of phosphorous-free antiscalants

Ammonium persulfate-initiated cyclopolymerization of maleic acid (HO₂CC=CCO₂H) (MA) with diallylamine (–NR₂, R = CH₂ = CH-CH₂) derivatives (DADs): R₂NH⁺CH₂CO₂⁻ ( I ), R₂NCH₂CO₂⁻Na⁺ ( II ), R₂NCH₂CO₂Et ( III ), R₂NH⁺(CH₂)₃CO₂⁻ ( IV ), R₂N(CH₂)₃CO₂Et ( V ), R₂NH⁺(CH₂)₃SO₃⁻ ( VI ) and R₂N(CH₂)₃SO₃⁻Na⁺ ( VII ) gave a series of new pH-responsive alternate copolymers: –[(DAD-alt-MA)]_n– VIII - XIV , respectively. Homopolymers XV and XVI of the corresponding monomers IV and V ·HCl were also synthesized. The evaluation of the synthesized polymers as potential antiscalants in reverse osmosis (RO) plants was examined. An effective scale inhibitor must arrest the formation of scale for a residence time (≈15 min) of feed water in the RO chamber. R₂NH⁺(CH₂)₃CO₂⁻ ( IV )-alt-MA copolymer XI at a concentration of 5 ppm imparted 99% scale inhibition for 360 min, while at 2.5 and 1 ppm concentrations, the CaSO₄ scale inhibitions were found to be 99% and ≈ 100% during 120 and 20 min, respectively, at 40°C. Homopolymers XV and XVI , at a 20-ppm concentration, demonstrated ≈ 95% efficiency in inhibiting mild steel corrosion in 1 M HCl. In some important oilfield applications, requirement of simultaneous scale and corrosion inhibition make these polymers potential candidates for desalination and oilfield applications.     

Synthesis and properties of novel alkyl sulfate gemini surfactants

Four anionic gemini surfactants of the sulfate type C₁₂C_nC₁₂, where n is the spacer chain length (n = 3, 4, 6, and 10) were synthesized. The structures of these surfactants were confirmed by FT‐IR, ¹H NMR, ESI mass spectra (ESI‐MS), and elemental analysis. The surface‐active properties of these compounds were investigated by means of surface tension, electrical conductivity, and fluorescence measurements. Premicellar aggregations were found for the four gemini surfactants, as revealed by the conductivity measurement. The formation of premicellar aggregates may account for the discrepancy between the critical micelle concentration (cmc) obtained by the surface tension and conductivity measurement. The cmc values of these gemini surfactants were much lower than that of sodium dodecylsulfate (SDS) and decreased monotonously with the increase of spacer chain length from 3 to 10. The effect of spacer chain length on the performance properties like foaming, emulsion stability, and lime soap dispersing ability were also studied and discussed. Practical applications : Alkyl sulfate surfactants are one of the most widely used surfactants. The new alkyl sulfate gemini surfactants synthesized in our study are more surface‐active than sodium dodecylsulfate. These gemini surfactants possess low critical micelle concentrations, high emulsion stability, and excellent lime soap dispersing ability. They have potential applications in the fields of cosmetics, detergents, etc.     

Oxypropylation of fatty alcohols,and the sulfation products

Reaction of propylene oxide, rather than ethylene oxide, with fatty alcohols, gives a higher yield (50%) of mono-oxyalkylation product because the secondary alcohol formed is less reactive than the primary alcohol formed with ethylene oxide. Rate of further reaction is about half the rate of the parent primary alcohol. Distributuon of propylene oxide reaction products follows the Weibull-Nycander equation. Analysis of reaction products was accomplished by gas-liquid chromatography of the acetylated ether alcohol mixtures. Pure mono-oxypropylated alcohols ROCH₂CHOHCH₃ and in some cases dioxypropylated alcohols R[OCH₂CH(CH₃)]₂OH were separated by fractional distillation. Individual ether alcohols and products with a known average number of oxypropyl groups were sulfated and evaluated in terms of Krafft point, critical micelle concentration, detergency, foam height and lime soap dispersing properties. Incorporation of one oxypropyl group was more effective than the same degree of oxyethylation, and improved solubility with no significant loss in foaming and detergency. Ether alcohol sulfates from propylene oxide are stable to alkaline hydrolysis and nearly equal to the sulfates from ethylene oxide in their stability to acid hydrolysis. Presented at the AOCS Meeting in Cincinnati, 1965. E. Utiliz. Res. Dev. Div., ARS. USDA.     

Soap-based detergent formulations: XII. Alternate syntheses of surface active sulfobetaines

Sulfopropylated amphoteric surfactants, previously reported in this journal, displayed excellent surface active properties and were good detergents in combination with soap. New synthetic routes were investigated for the preparation of such types of compounds to provide a more economical process and eliminate the hazards due to propanesultone, which was used in the previously reported synthetic procedure. A series of 2-hydroxy-3-sulfopropyl amphoteric surfactants was prepared by reacting sodium 3-chloro-2-hydroxy-1-propanesulfonate (the addition product of sodium bisulfite to epichlorophydrin) with various primary fatty amines as well as with fat derived N,N-dimethylalkylamines. Quaternary sulfobetaines not possessing a hydroxyl group were obtained from tertiary amines by reaction with allyl chloride followed by bisulfite addition. The solubility behavior (Krafft points) of these compounds indicated that they were not identical with the sulfobetaines prepared with the aid of propanesultone. The secondary and quaternary ammonium compounds exhibited limited water solubility but were good lime soap dispersing agents. They displayed good detergency in combination with soap. The quaternary ammonium derivatives were particularly effective on cottonpolyester blend fabrics. Presented at the AOCS Meeting, Philadelphia, September 1974.     

Sulfated diglycolamides

Pure sulfated diglycolamides were prepared by the sulfation of products from the alkali-catalyzed reaction of diglycolamide with fatty methyl esters. Products containing 70% of methyl-substituted diglycolamides were obtained by the addition of 1 mole of propylene oxide to a mole of hydroxyethylamide under alkaline catalysis. Sulfated monooxypropylated hydroxyethylstearamide C₁₇H₃₅ CONHC₂H₄OCH₂CH(GH₃)OSO₃Na, and sulfated diglycolstearamide, C₁₇H₃₅CONH (C₂H₄O)₂-SO Na, have good solubility, lime soap dispersing power and detergency. Presented at the ISF-AOCS Meeting, Chicago, Illinois, September 1970. Eastern Marketing and Nutrition Research Division, ARS, USDA.