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.     

Detergency of binary mixtures of LAS/STPP and LAS/Zeolites: influence of (Ca++) on the washing liquor

The influence of sodium tripolyphosphate (STPP) or zeolites on the detergency performance of linear alkylbenzene sulfonate (LAS) has been evaluated at different water hardness levels. This study demonstrates that STPP or zeolite behaves either as a sequestrant or through an important synergism with LAS, showing a minimum and a maximum in detergency performance, depending on the water hardness level. There is an optimum LAS/builder ratio for each individual water hardness level. This optimum has to be determined experimentally as it will not always necessarily coincide with the highest surfactant and/or builder concentrations.     

Studies on replacement of phosphate builders in laundry detergents using radiolabeled soils

The fabric detergency performance of systems containing different types of surfactants and several builders of reduced phosphate content has been compared using a radiolabeled sebum-clay soil. Use of this soil allows quantitative measurement of both sebum and clay removal from soiled swatches, generally cotton and permanent press Dacron-cotton. One study compared alkylbenzene sulfonate (LAS), alcohol sulfate (AS), alcohol ethoxysulfate (AEOS) and alcohol ethoxylate (AEO) as surfactants in formulations containing from 0–45% sodium tripolyphosphate (STPP). Especially under hard water conditions, the AEO and AEOS considerably out-perform the LAS and AS at equal use concentrations and are less sensitive to phosphate reduction. Tests with cotton swatches soiled with five different carbon black-oil mixtures generally rank the surfactants in the same order, although individual responses of the cloths vary considerably. A further study compares the effect of replacing STPP with sodium nitrilotriacetate (NTA) in formulations containing varying amounts of AEO or LAS. Detergency improves significantly with increasing surfactant concentration, particularly with AEO, and declines as builder strength is reduced. AEO exceeds LAS considerably in performance under the test conditions even at relatively high concentrations of LAS. Another study compares the performance of AEO and LAS at equal concentrations in formulations containing a variety of builders. AEO is generally superior to LAS in removing both sebum and clay soils and is less sensitive to builders and water hardness. The builders generally rank in this order: STPP > NTA = citrate > carbonate > sulfate. Presented at the AOCS Short Course, “Update on Detergents and Raw Materials,” Lake Placid, N.Y., June 1971.     

Interactions between LAS and nonionic surfactants

Physicochemical interactions between linear alkylbenzene sulfonate (LAS) and various linear alcohol nonionics (NI) have been investigated. The effect of adding nonionic to LAS on critical micelle concentration (cmc), surface tension, water hardness sensitivity and detergency performance depends on both hydrophobe and hydrophile structure. The addition of low levels of a lauryl range-high EO nonionic surfactant significantly lowers cmc and causes the formation of micelles containing predominantly nonionic molecules. These mixed micelles improve hard water performance by acting as a sink for LAS and free calcium. Nonionic surfactant enhances LAS hard water performance by preventing the loss of LAS via Ca(LAS)₂ precipitation, not by its own soil removal capabilities. Nonionic surfactant acts as a micelle promotion agent, while LAS remains responsible for surface and interfacial properties. Presented at the AOCS meeting in May 1984 in Dallas, Texas.     

烷基苯磺酸镁盐—产品柔和性和使用性能的改善（英）

已经测出直链烷基苯磺酸镁盐在水溶液中的许多特性,例如：表面张力,临界胶速浓度,比电导率,粘度,溶解性,生物降解性,毒性和对硬水的稳定性等,同时与相应的钠盐作用了对比。     

Effect of carbon chain and phenyl isomer distribution on use properties of linear alkylbenzene sulfonate: A comparison of ‘high’ and ‘low’ 2-phenyl LAS homologs

Phenyl isomer distributions, within current commercial limits of HF and A1C13 linear alkylbenzene sulfonates (LAS), have little effect on dishwashing performance in light-duty liquids (LDL), detergency performance in heavy-duty powders (HDP), and interfacial tension value. The most important factor in determining performance differences among commercial LAS samples is carbon chain homolog distribution. Both HF and A1C1₃ LAS perform equally well and can be used interchangeably in high-performance products. The optimum for foam stability in light-duty liquids shifts towards shorter alkyl chain length as water hardness increases. At 0 ppm water hardness the optimum occurs at C₁₃: at 50–150 ppm the optimum moves to C₁₁ and C₁₂; and above 150 ppm the optimum shifts to include C₁₀, C₁₁ and C,₁₂. The detergency performance optimum range in a phosphate built heavy-duty powder at 50 and 150 ppm water hardness includes the C₁₂, C₁₃ and C₁₄ alkyl chain lengths. In a nonphosphate built powder the optimum is similar at 50 ppm hardness to that of a phosphate built powder, but shifts at 150 ppm hardness to include C₁₁, C₁₂ and C₁₃.     

直链烷基苯磺酸镁的温和作用和应用性能（英）

对直链烷基苯磺酸镁盐（ＬＡＳ２ Ｍｇ） 与钠盐水溶液中诸多性质的对比做了大量研究。例如， 表面张力、临界胶束浓度、比电导、粘度、溶解性、生物降解性、毒性及耐硬水性等。同时， 对ＬＡＳ２ Ｍｇ 的其它性能如Ｚｅｉｎ 试验（ 一种皮肤刺激性试验） ， 润湿性及在盥洗用品和餐具洗涤剂中的应用性能也进行了测试。镁盐的一些特殊性质及其在洗涤剂和化妆品领域中新的应用的可能性得到了证实或确认。     

The interaction of dimethyl ditallow ammonium chloride and sodium linear alkylbenzene sulfonate

The interaction of a commercial sample of dimethyl ditallow ammonium chloride (Adogen? 470E) and sodium alkylbenzene sulfonate (C-550 LAS) in aqueous solution was examined. Interaction was very strong, with the ion pair association constant estimated to be 1 × 10⁶ 1/mol. At laundry use level concentrations, the mixtures were turbid. The highest turbidity was found at equimolar concentrations of C-550 LAS and Adogen? 470E. Turbidity was assumed to be due to the formation of an insoluble 1:1 complex. Both filtered and unfiltered mixtures of C-550 LAS and Adogen? 470E were evaluated for detergency, softening and antistat performance. As the mixtures approached 1:1 stoichiometry, detergency decreased and softening and antistat performance improved. Lower detergency was explained by the loss from solution of LAS to form a 1:1 LAS-dimethyl ditallow ammonium complex. Improved softening and antistat perfromance were explained by adsorption of the insoluble complex on the cloth. Presented May 10, 1988 at the 79th Annual AOCS Meeting, in Phoenix, Arizona.     

脂肪酸甲酯磺酸钠在洗涤剂中的应用性能研究

将脂肪酸甲酯磺酸钠(MES)分别配成液体和粉状洗涤剂,测定不同时间内MES的水解率、表面活性剂的发泡力、表面活性剂和洗涤剂的去污力。结果表明,MES在碱性液体洗涤剂和洗衣粉料浆中容易水解,在10%的碳酸钠溶液中水解率达28.87%;MES在硬水中的发泡力明显好于烷基苯磺酸钠(LAS)。无论是表面活性剂还是在洗涤剂中,MES均显示出超强的去污力,去污力比值是LAS的1.6~1.7倍;MES与LAS复配时,去污力无协同增效作用。     

The influence of sodium tripolyphosphate and zeolites on detergency of linear alkylbenzene sulfonate in the presence of Mg++

The influence of sodium tripolyphosphate (STPP) and zeolites on the detergency performance of linear alkylbenzene sulfonate (LAS) has been evaluated at different water magnesium ion levels. This study demonstrates that LAS/STPP gives better results in the presence of calcium than in the presence of magnesium, whereas the LAS/zeolite mixture gives better results in the presence of magnesium than in the presence of calcium.     

Effect of water hardness ions on the solution properties of an anionic surfactant

The solution characteristics of the system linear alkylbenzene sulfonate (LAS)/Ca⁺⁺/builder were studied using a dynamic surface tension technique. The results showed that the rate of CA⁺⁺/LAS interaction is slower than the CA⁺⁺ binding rate of zeolite A. Consequently, zeolite A is effective in preventing precipitation of LAS by calcium ions. The data obtained from the study of Ca⁺⁺ binding detergent builders on solubilization of Ca(LAS)₂ showed that zeolite A was effective but the rate of solubilization was much slower than that for STPP. Incorporation of a small amount of phosphate with zeolite A in a detergent significantly increases the rate of solubilizing of Ca(LAS)₂.     

Interactions between linear alkylbenzene sulfonates and water hardness ions. I. Effect of calcium ion on surfactant solubility and implications for detergency performance

This paper examines the interactions of linear alkylbenzene sulfonate (LAS) surfactants with calcium ions. Calcium sulfonate precipitation boundary diagrams are given which provide a convenient way to study these interactions over a wide range of surfactant and hardness ion levels. Some implications of these interactions for detergency performance are discussed. Presented at AOCS meeting in Philadelphia, May 1985.     

Performance of straight-chain alkylbenzene sulfonates (LAS) in heavy-duty detergents

The foamability (dishwashing and washing machine) and detergency of LAS in heavy-duty detergents is directly compared with polypropylenė ABS (PPABS) at various mol wt, conen, water hardnesses and temp. In every case a peak in performance is obtained in the C₁₁ to C₁₇ side chain range. The peak is shifted to lower mol wt as water hardness is increased, especially at low detergent conen. LAS opt performance is generally equal to PPABS, except in dishwashing foam in soft water. The LAS peaks, however, are shifted to ca. one carbon lower mol wt than the PPABS. Therefore, best over-all performance is obtained for LAS whose average mol wt corresponds to a 12.5 carbon side chain, whereas PPABS is best with an average 13.5 carbon side chain. Dishwashing foamability is markedly different for the different isomers contained in LAS. When the phenyl group it attached to the middle of the alkyl chain, surprisingly high results are obtained. This dishwashing difference is great enough to be noticeable when the isomer distribution changes in whole products made using different alkylation catalysts. Detergency and washing machine foam are not affected enough to see differences between whole alkylates. LAS solubility is greater than PPABS and is influenced by isomer distribution. Present address: W. Reg. Res. Lab., USDA, Albany, Calif.     

α-Sulfo Fatty Methyl Ester Sulfonate: A Review on Chemistry,Processing Technologies,Performance, and Applications in Laundry Detergents

α-Sulfo fatty methyl ester sulfonate (α-MES) is one of the anionic surfactants that is currently used commercially in the cleaning industry. Although the fundamental studies on α-MES were initiated as far back as the 1950s, it was only recognized as a class of surfactant in the 1980s. In the initial stage of development, α-MES has been associated with many technical impediments, which created a fear factor for the detergent industry to consider this oleo-based anionic surfactant for commercial production. However, all the technical adversities have been resolved after five decades of continuous active research and development activities. This paper will review the history, chemistry, process development, processing technologies, performance, commercial production, and applications of oleo-based based α-MES with special emphasis on palm oil-based α-MES. The paper also will highlight the challenges and adversities faced by the technology developers and product formulators toward the commercialization of α-MES as an active ingredient in the production of powder and liquid laundry detergents.     

Facile Hydrothermal Synthesis of Hierarchical Sodium P Zeolite as a Nonphosphate Detergent Builder

This study reports the preparation of hierarchical NaP zeolite with the aim of obtaining a non-phosphate detergent builder as an alternative for environmental remediation from eutrophication phenomenon. Hierarchically structured NaP zeolite was easily synthesized hydrothermally and under different syntheses conditions. Samples were characterized using several standard techniques such as X-ray diffraction (XRD), scanning electron microscopy (SEM), Fourier transform infrared (FT-IR) spectroscopy, and N₂ adsorption–desorption analysis. Three powder detergents were prepared by mixing main components such as linear alkylbenzene sulfonate, sodium sulfate, sodium silicate, and sodium carbonate as well as different amounts of as-synthesized zeolite and sodium tripolyphosphate in the detergent formulation as potential detergency builders. Some different detergency tests as pH value, water insolubility, foam height, moisture content, alcohol insolubility, and surface tension measurement were carried out for all synthetic detergent samples and two commercial ones. The results demonstrated that the high cleaning performance of the powders was obtained as using eco-friendly zeolite builders in comparison with phosphate-based commercial and synthetic detergent samples.     

Linear alkylbenzene sulfonate detergency behavior in water containing magnesium ions

Detergency performance of linear alkylbenzene sulfonate (LAS) in water containing magnesium ions has been investigated. LAS showed the same behavior with magnesium as with calcium, on a qualitative basis. However, the detergency performance with magnesium is significantly higher than with calcium.     

无机盐对表面活性剂去污力影响的研究

用去污实验机测定了直链烷基苯磺酸钠(LAS)、脂肪醇聚氧乙烯醚硫酸钠、α-烯基磺酸钠、脂肪酸甲酯磺酸钠等阴离子表面活性剂的去污力,考察了无机盐对去污力的影响。结果表明,三聚磷酸钠使这几种表面活性剂的去污值增加了29.11%~121.26%,磷酸三钠使LAS的去污值增加了128.25%;三聚磷酸钠、δ-层状结晶二硅酸钠、4A沸石等软水剂增强去污力的效果最好,碳酸钠和硅酸钠等碱性助剂次之;硫酸钠、氯化钠、磷酸二氢钠和十水四硼酸二钠不适合用作洗涤剂的助洗剂。     

Interactions between linear alkylbenzene sulfonates and water hardness ions. II. Reducing hardness sensitivity by the addition of micelle promotion agents

Agents which promote micellization of linear alkylbenzene sulfonates (LAS) improve LAS hard-water detergency performance by reducing water hardness sensitivity. A model is proposed which correlates micellization and water hardness tolerance. The ability of inorganic salts and cosurfactants to act as micelle promotion agents is discussed. Presented at the AOCS meeting in Philadelphia, May 1985.     

烷基苯磺酸钠／烷基二苯醚双磺酸盐复配体系的洗涤性能研究

主要考察了烷基苯磺酸钠（LAS）与十六烷基二苯醚双磺酸盐（D8390）复配体系在不同复配比、不同浓度、不同水硬度、不同温度条件下对不同种类污布的洗涤能力。结果表明：（1）对于碳黑、皮脂两种污布,单独D8390的洗涤能力不及LAs,LAS／D8390复配体系在w（LAS）：w（D8390）=8：2—7：3范围内洗涤能力最高;（2）对于蛋白污布,单独D8390的洗涤能力明显高于LAS,且在两者复配体系中,随着D8390含量的增加,洗涤能力先快速增大,在w（LAS）：W（D8390）=3：7时达到最高点,之后略降低。（3）在W（LAS）：W（D8390）=7：3的复配体系中,活性物总质量浓度在0．10％-0．20％范围内,质量浓度对碳黑、皮脂两种污布的洗涤能力影响不明显,但随着浓度的降低,对蛋白污布的洗涤能力明显降低;（4）采用LAS与D8390进行复配,可以明显改善体系在高硬度、低温下的洗涤能力。     

Influence of calcium concentration in the washing liquor on detergency performance of linear alkylbenzene sulfonate

The effect of the concentration of linear alkylbenzene sulfonate (LAS) on soil removal efficiency at various water hardnesses was studied. The present investigation indicates that: (i) For each LAS concentration, a calcium ion concentration interval exists, defined by 0.78<(Log(LAS)/Log(Ca))<0.85, where the detergency reaches a maximum; (ii) 24 h after having been prepared, the solutions present either clear solutions (water appearance), milky solutions (without precipitate in the bottom of the bottle), or clear solutions with precipitate in the bottom of the bottle. The milky solutions correspond to the defined interval. The solutions where the relationship LAS/Ca is defined are located, surprisingly in a precise zone of the LAS-calcium solubility diagram. The study has been carried out with and without ionic strength buffering, and the addition of electrolyte moves the maximum detergency performance interval to higher calcium concentrations.