No full-text available
To read the full-text of this research,
you can request a copy directly from the author.
Sulfosuccinates as Mild Surfactants
Abstract
Sulfosuccinate type anionic surfactants have been the workhorse surfactants as mild cleanser. Sulfosuccinates makeup around 49% of all anionic surfactants. Sulfosuccinates are the sodium salts of alkyl ester of sulfosuccinic acid. These surfactants having two long lipophile chains are similar to the alkyl sulfonates. In general, sulfosuccinate surfactants have been used in the cosmetic industry to improve the mildness of personal care products. This paper attempts to review the chemistry, types, synthesis, properties and distinguishing features of sulfosuccinates. The various applications of sulfosuccinate type anionic surfactants have also been discussed in detail.
... Both mono-and dialkyl sulfosuccinates are one of the main anionic emulsifiers used in E-PVC [9-12They have excellent wetting, emulsifying, dispersing, and foaming properties. [11][12]. Typically, di-alkyl sulfosuccinate emulsifier groups are used as viscosity depressant in emulsion PVC [10]. ...
... Also from literature it is understood that emulsifiers from sulfosuccinate group give medium size particles [9]. Sodium di-isodecyl sulfosuccinate (SDIDS) is an anionic double-chain sulfonate emulsifier with long side-chain length (around 10 carbons) in hydro-alcoholic solutions that are widely used in the E-PVC [10][11][12]. ...
... Isopropyl alcohol is a commonly used solvent in the synthesis of SDIDS [11,12]. It is a common process in industry that the chemical source providers change the concentration of this alcohol occasionally in their products for different reasons. ...
The condition of oligo-micelle formation of sodium di-isodecyl sulfosuccinate (SDIDS) emulsifier in hydro-alcoholic solutions is used to study particle formation of vinyl chloride emulsion polymerization in a batch reactor. The change on micellization behavior was investigated by critical micelle concentration (CMC) and zeta potential parameters. To detect the occurrence of secondary nucleation or particle aggregation, or both, the particle size and number of particles were investigated as a criterion for the particle nucleation and growth process. The results showed the alcohol content as a co-solvent has a strong effect on the oligo-micelles formation and emulsion polymerization performance. Namely, decreasing the alcohol content and increasing the anion content in the SDIDS samples increased the overall reaction rate and latex stability. This also decreased the chain growth rate, the particle size, and the coarse particle formation. Also, the results showed that different condition of oligo-micelle formation would lead to different particle growth history.
... Flexible spacers (such as methylene chains) allow the head groups to move relative to one another and to adopt a preferred separation distance and orientation based on solvation energetic and entropic consideration [2,3]. Sulfosuccinate anionic surfactants are mild among all the anionic surfactants [4]. Sulfosuccinate surfactants have extraordinary performance properties such as foaming, strong wetting, emulsifying, solubilizing properties, and excellent surface active properties, viz. ...
... Tables 1, 2, 3, and 4 exhibited the experimental outcomes, which demonstrated that the interaction between our 1,4 in the presence of inorganic and organic salts examined gemini surfactants, viz. BSGSLA's and BSGSCA's, and the counter-ions was found to be increased with elongated spacer chain length. ...
... The results shown in Fig. 6 revealed the maximum foam stability of gemini surfactants with shorter (CH 2 ) 4 spacer length in all synthesized lauryl and cetyl alcohol-based gemini surfactants, viz. BSGSLA 1,4 and BSGSCA 1,4 , in contrast to other prepared gemini surfactants having longer spacer groups. The results revealed the reduced foam stability with elongated spacer group for BSGSLA 1,8 and BSGSCA 1,8 . ...
Current communication reports the inorganic and organic salt behavior towards the surface active properties of lauryl and cetyl alcohol-based bis-sulfosuccinate anionic gemini surfactant (BSGSLA’s and BSGSCA’s) having different spacer and alkyl chain lengths by means of tensiometric measurements. The results revealed the enhanced surface activity and reduced critical micelle concentration (CMC) of gemini surfactants with the interaction of different salts as well as with increased salt concentration. The CMC reduction pattern reflects the profound influence of different salts of bis-sulfosuccinate anionic gemini surfactants and considerably noticed as sodium salicylate > sodium benzoate > potassium chloride > sodium chloride. This finding divulged the superior interaction behavior of organic salts in contrast to inorganic salts. The outcome of these investigations pointed out towards the improvement scrutinized in surface activity of bis-sulfosuccinate gemini surfactants with different salts which evidently supported with the eyecatching reduction in CMC with various factors including, viz. enhanced salt concentration, elongated spacer group as well as enlarged alkyl chains of gemini surfactants. The results also confirmed that the synthesized anionic bis-sulfosuccinate gemini surfactants, viz. BSGSLA’s and BSGSCA’s, exhibited promising performance properties.
... Salts of the monoester of sulfosuccinic acid are in general obtained by reacting maleic acid, fumaric acid, or maleic anhydride with fatty alcohol, alkoxylated fatty alcohol, or fatty acid alkanolamides. The resulting butanedioic acid half ester is sulfonated with sulphite, pyrosulfite or bisulfite of alkaline earth metal to get the desired salts of monoester of sulfosuccinic acid [2][3][4]. ...
... Because of their solubility in water, organic solvents and even hydrocarbons, diester sulfosuccinate are also used in dry-cleaning formulations. Different types of sulfosuccinates and their synthesis, properties, and industrial applications are reviewed in the literature [2,3]. Most of the succinate monoesters are synthesized by reacting maleic anhydride with primary alcohol, and there are very few reports wherein secondary alcohol was reacted with maleic anhydride to synthesize branched succinate monoester [2][3][4][5][6]. ...
... Different types of sulfosuccinates and their synthesis, properties, and industrial applications are reviewed in the literature [2,3]. Most of the succinate monoesters are synthesized by reacting maleic anhydride with primary alcohol, and there are very few reports wherein secondary alcohol was reacted with maleic anhydride to synthesize branched succinate monoester [2][3][4][5][6]. The present work is directed towards the synthesis of branched succinate monoester, which may provide an ideal building block for newer surfactants. ...
Sulfosuccination of castor oil-derived methyl ricinoleate and methyl 12-hydroxy stearate have been carried out in the present work. Synthesis involves malenization of secondary alcohol of methyl ricinoleate/methyl 12-hydroxy stearate followed by sulfonation of maleic monoester to generate double-headed dianionic surfactant with carboxylate and sulfosuccinate functionalities in the head group region. Various reaction conditions were optimized for maximum production of these two sulfosuccinates. Both compounds were evaluated for surface and detergency properties. The surface tension study indicated that the critical micelle concentration of sulfosuccinated methyl ricinoleate and methyl 12-hydroxy stearate is 0.26 and 0.11 mM, respectively. The detergency property of these two surfactants indicated that they were excellent in wetting time emulsification and Ca-tolerance. However, these two surfactants exhibited very poor foam height and foam stability.
... These ingredients are also the salts of alkyl PEG, monoesters of sulfosuccinic acid, and are collectively referred to as alkyl PEG sulfosuccinates, even though none of the INCI names includes PEG. 5 For example, disodium laureth sulfosuccinate consists of a 12-carbon alkyl chain (lauryl), connected to the sulfosuccinate core via a PEG chain, wherein the average number of ethoxy repeat units (n) is between 1 and 4 (ie, laureth-1 through laureth-4; Figure 1). ...
... Sulfosuccinate monoesters contain a hydrophobic end that consists of a fatty alcohol chain. 5 The chain length and degree of saturation of the fatty acid may vary this hydrophobicity. The level of hydrophobicity imparted by the fatty alcohol is also affected by the different degrees of ethoxylation of the Water solubility is also increased when the structure contains branched chains. ...
... The synthesis of these ingredients occurs according to a 2-step procedure. 5 In the first step, maleic anhydride is reacted with an ethoxylated fatty alcohol. The second step involves sulfonation of the resulting maleic ester. ...
The Cosmetic Ingredient Review (CIR) Expert Panel (Panel) reviewed the safety of alkyl polyethylene glycol (PEG) sulfosuccinates, which function in cosmetics mostly as surfactants/cleansing agents. Although these ingredients may cause ocular and skin irritation, dermal penetration is unlikely because of the substantial polarity and molecular size of these ingredients. The Panel considered the negative oral carcinogenicity and reproductive and developmental toxicity data on chemically related laureths (PEG lauryl ethers) and negative repeated dose toxicity and skin sensitization data on disodium laureth sulfosuccinate supported the safety of these alkyl PEG sulfosuccinates in cosmetic products, but. The CIR Expert Panel concluded that the alkyl PEG sulfosuccinates are safe in the present practices of use and concentration when formulated to be nonirritating.
... In current production processes, maleic anhydride is reacted with any variety of hydroxyl containing lipophilic compounds in a ring opening followed by sulfonation of the double bond on the maleic ester [20]. The reaction conditions can be controlled such that the mono-or diester is the preferred product, and it is possible to tailor the properties of the monoesters by changing the chain length or saturation of the alkyl group or by using an ethoxylated fatty alcohol or alkanolamides of fatty acids. ...
... The reaction conditions can be controlled such that the mono-or diester is the preferred product, and it is possible to tailor the properties of the monoesters by changing the chain length or saturation of the alkyl group or by using an ethoxylated fatty alcohol or alkanolamides of fatty acids. For the diesters it is possible to change the properties by using either linear, branched or cyclic alkyl groups [20]. ...
IntroductionExisting and Potential Classes of Surfactants from Biologically Derived MetabolitesFermentation-Based Building Blocks with Large Existing MarketsNew Fermentation-Based Building BlocksConclusion
References
... The maleic acid monoester thus formed then reacts with aqueous sodium sulphite at 75-90 °C forming the sulphosuccinate. For the preparation of sulphosuccinic acid diesters, the ring-opening and esterification of Ma is Sulphosuccinic acid monoesters of fatty alcohol polyglycol ethers are used as foam-active, mild cosmetic surfactants for shampoos 125 (including "no more tears" baby shampoos) and, as well as dihexyl and dioctylsulphosuccinate, as emulsifiers for the preparation of polymer dispersions by emulsion polymerisation. 126 Furthermore, dioctylsulphosuccinate is characterised by its pronounced wetting properties and low dynamic surface tension, and is therefore used as a wetting agent in industrial high-speed processes in the paper and textile industries as well as in plastic packaging, in pressuresensitive adhesive applications, and ink-jet printing. ...
... Surfactants are amphiphilic substances with lipophilic as well as hydrophilic properties and are extensively utilized for the rejuvenation of polluted environmental sites (Gautam & Tyagi, 2006;Paria, 2008). Detergents, such as alkylbenzene sulfonates (Petrovic et al., 2002), fatty acid-based soaps (Johansson & Svensson, 2001), foaming agents, including lauryl sulfate (Granero, Ramachandran, & Amidon, 2005), lignosulfonates-based dispersants (Rana, Neale, & Hornof, 2002), and wetting agents, such as di-alkyl sulfosuccinate (Tyagi, 2006) are the most common surfactants used to reduce surface tension. However, these surfactants are toxic to the environment and other beneficial microbes in the contaminated sites, as they are fabricated via hazardous chemicals (Rebello, Asok, Mundayoor, & Jisha, 2014). ...
The application of biosurfactants has been observed to be most widely utilized in different industrial sectors including food and agriculture, medical and for environmental rejuvenation. Therefore, as effective mass production of biosurfactants as sustainable biomolecules depends largely on their ease of production on a large economic scale, the use cheap agro-waste are being explored as alternative sources of substarate. At present, biosurfactants do not compete with the chemical surfactants when viewed from the economic perspective. This is because the commonly used substrates for the production of biosurfactants are expensive and the overall yields from them are relatively low. Therefore, this chapter intends to provide detailed information on the sustainable biotechnologies that explores the application cheaper agricultural resources for effective mass production of biosurfactants.
... Generally, the literature describes a wide range of anionic surfactants which are considered as mild-acting [1,9,14,15]. Such compounds include sulphosuccinates [180], isethionates [35,36], sarcosinates [155], acylated protein hydrolysates and their salts [181], alkyl ether carboxylates [157], glutamic acid derivatives [38] and certain salts of alkyl ether sulphates (magnesium and zinc) [97,159]. ...
One of the primary causes of skin irritation is the use of body wash cosmetics and household chemicals, since they are in direct contact with the skin, and they are widely available and frequently used. The main ingredients of products of this type are surfactants, which may have diverse effects on the skin. The skin irritation potential of surfactants is determined by their chemical and physical properties resulting from their structure, and specific interactions with the skin. Surfactants are capable of interacting both with proteins and lipids in the stratum corneum. By penetrating through this layer, surfactants are also able to affect living cells in deeper regions of the skin. Further skin penetration may result in damage to cell membranes and structural components of keratinocytes, releasing proinflammatory mediators. By causing irreversible changes in cell structure, surfactants can often lead to their death. The paper presents a critical review of literature on the effects of surfactants on the skin. Aspects discussed in the paper include the skin irritation potential of surfactants, mechanisms underlying interactions between compounds of this type and the skin which have been proposed over the years, and verified methods of reducing the skin irritation potential of surfactant compounds. Basic research conducted in this field over many years translate into practical applications of surfactants in the cosmetic and household chemical industries. This aspect is also emphasized in the present study.
... Consequently, the bioactivity of modified lutein should be taken into consideration in food and medicinal fields. In this paper, a novel aqueous derivative of lutein, the disulfosuccinate sodium salt of lutein (Ldss), was successfully prepared based on a serial of chemical modifications of lutein ( Figure 1), 16,17 with the improved aqueous solubility, stability and radical scavenging ability. At first, lutein was modified into dimaleic acid ester of lutein with the combination of maleic anhydride, by esterification. ...
The disulfosuccinate sodium salt of lutein (Ldss) was prepared for the first time and an obvious blue shift appeared in the UV absorption spectra of its aqueous solution due to the formation of substantial H-type aggregates. The experimental results reflected the improved properties of Ldss, including excellent stability to alkaline solution at ambient temperature in the dark as well as better aqueous solubility and radical scavenging ability compared with those of lutein and the disodium disuccinate of lutein.
... The most used anionic surfactant class for baby or children shampoos is the sulfosuccinate based on lauryl alcohol ethers. Disodium laureth sulfosuccinate and disodium PEG-4 cocamido MIPA-sulfosuccinate are employed in mild skin and hair products, while disodium ricinoleamido MEA-sulfosuccinate and disodium sitosteareth-14 sulfosuccinate are used in baby shampoos (20). ...
This article aimed a review about a new market category that is children’s products. Nowadays the United States and Brazil lead this market. These products are for particular age groups such as baby (0-2 years), children (3-7 years), pre-teens (8-12 years) and teenagers (above 12 years). The child's skin is more hydrated, sensitive, has a pH around neutrality, the epidermis is thinner than an adult skin. To ensure the safety, they should be formulated with regard to children's skin that is more permeable and present increased susceptibility to skin infections. Restrictions of these products are regulated in each country so that the effectiveness and safety of these products are guaranteed.
... These esters often have improved properties for solubilization, wetting, foaming, and dispersing relative to other anionic surfactants. Moreover, they have wide applications in dry-cleaning solvents, printing, textile dying, paints and coatings, emulsion polymerization, cosmetics and shampoos [3][4][5][6][7]. ...
... These esters often have improved properties for solubilization, wetting, foaming, and dispersing relative to other anionic surfactants. Moreover, they have wide applications in dry-cleaning solvents, printing, textile dying, paints and coatings, emulsion polymerization, cosmetics and shampoos [3][4][5][6][7]. ...
... These esters often have improved properties for solubilization, wetting, foaming, and dispersing relative to other anionic surfactants. Moreover, they have wide applications in dry-cleaning solvents, printing, textile dy- ing, paints and coatings, emulsion polymerization, cos- metics and shampoos [3][4][5][6][7]. ...
... These esters often have improved properties for solubilization, wetting, foaming, and dispersing relative to other anionic surfactants. Moreover, they have wide applications in dry-cleaning solvents, printing, textile dying, paints and coatings, emulsion polymerization, cosmetics and shampoos [3][4][5][6][7]. ...
Sulfonated acrylate esters have been synthesized by using renewable raw materials such as fatty alcohols of Al-Ceder oil. Mixed fatty acids were isolated from Al-Ceder oil by hydrolysis; both saturated and un-saturated fatty acids were isolated from the mixed fatty acids. The methyl esters of mixed fatty acid, saturated and unsaturated acids of Al-Cedre oil were subjected to reduction with (LiAlH4) to give the corresponding fatty alcohols. The products of the reduction process were saponified and the hydroxyl values were estimated to further confirm the reduction occurrence. The acrylate esters were synthesized by esterification of acrylic acid with fatty alcohols of C 16:0 , C 18:0 , C 18:1 , and C 18:2 mixed saturated, mixed unsaturated and mixed fatty acids of Al-Cedre oil, respectively. This esterification was followed by addition of NaHSO 3 to form bisulfite adducts. The structures of the prepared surfactants were characterized by IR and 1 HNMR spectroscopy. A series of useful surface parameters, stability towards acids and base hydrolysis and calcium stability have been determined.
... Because flexible spacers (such as methylene chains) allow to the head groups to move relative to one another, and to adopt a preferred separation distance and orientation based on solvation energetic and entropic consideration [2]. Sulfosuccinate anionic surfactants are mild amongst all the anionic surfactants [3]. Sulfosuccinate surfactants have extraordinary performance properties such as foaming, strong wetting, emulsifying, solubilizing properties and excellent surface active properties viz. ...
In this research work, fluorescence technique has been utilized to investigate the association/aggregation properties of aqueous solution of pure lauryl alcohol based bis-sulfosuccinate anionic gemini surfactant (BSGSLA1,8) having flexible methylene (CH2)8 as spacer. As well as fluorescence interaction behavior of mixed surfactant solutions of BSGSLA1,8 with conventional surfactants, anionic viz. sodium dodecyl sulphate (SDS), cationic viz. cetyl trimethyl ammonium bromide (CTAB) and non-ionic surfactant viz. Triton X 100 for industrial utility purpose of surfactant formulations was also studied. Aggregation number and micropolarity of pure and mixed surfactants systems were investigated by using steady-state fluorescence spectroscopy technique. Electrolyte effect of sodium chloride (NaCl) on account of aggregation number and micropolarity was also explored for pure BSGSLA1,8 at different concentration of NaCl. The best synergism behavior of BSGSLA1,8 has been noticed with SDS as compared to CTAB and Triton X 100. The maximum reduction of pyrene intensity ratio (I1/I3) was noticed for BSGSLA1,8 and SDS mixed surfactant solution. The enhanced I1/I3 value of mixed gemini with Triton X 100 shows that mixed system is not as compact as pure BSGSLA1,8 surfactant micelles due to nonionic surfactant.
... In an effort to identify the compound(s) responsible of this inhibition, we performed infrared spectral analyses and identified sodium laureth-1 sulfate, Alipol HF-433 and Dowfox 2A1 as molecules released by nylon flocked swabs treated with ethylene oxide. Sodium laureth-1 sulfate is a surfactant [12] and detergent used mainly in skin cleansers, gel shampoos or shower products. This molecule is closely related to sodium dodecyl sulfate widely used in molecular biology for its protein denaturing property. ...
Objective
Skin cleansing products are among the main reasons for the development of hand eczema. Therefore, a mild but effective skin cleansing product is of particular interest, especially in the work place, where various contaminations frequently have to be removed from hands.
Methods
In this study, the potential of laureth‐23 as a primary surfactant was evaluated and compared to other fatty alcohol ethoxylates (FAEO). Also, different laureth‐23 surfactant combinations were compared to each other. Therefore, transepidermal water loss, erythema and visual scoring were measured after occlusive patch testing in 24 healthy subjects (aged 18–55). Afterwards, the results were ranked from low to high irritant potential and an irritation score was calculated. Furthermore, the cleaning performance was tested using an automated cleansing device in 10 healthy subjects (aged 18–55).
Results
The results confirmed the low irritant potential of laureth‐23 and blends thereof. Within the different laureth‐23 surfactant combinations, the combination of laureth‐23 with a mild amphoteric and a mild anionic surfactant was superior to other laureth‐23 surfactant combinations like laureth‐23/anionic/anionic regarding skin compatibility as well as cleaning performance.
Conclusion
In conclusion, laureth‐23 showed very good performance as a primary surfactant. Especially, the combination of laureth‐23, cocamidopropyl betaine and disodium laureth sulfosuccinate was mild to the skin while also showing good cleansing performance.
Understanding the potential impact of organic contaminants on male fertility is crucial, yet limited studies have examined these chemicals in semen, with most focusing on urine and blood. To address this gap, we developed and validated a robust LC-HRMS methodology for semen analysis, with a focus on polar and semipolar chemicals. Our methodology enables the quantitative (or semiquantitative) analysis of >2000 chemicals being compatible with suspect and nontarget strategies and providing unprecedented insights into the occurrence and potential bioaccumulation of diverse contaminants in this matrix. We comprehensively analyzed exogenous organic chemicals and associated metabolites in ten semen samples from Spanish participants collected in an area with a large presence of the chemical industry included in the LED-FERTYL Spanish study cohort. This investigation revealed the presence of various contaminants in semen, including plastic additives, PFAS, flame retardants, surfactants, and insecticides. Notably, prevalent plastic additives such as phthalic acid esters and bisphenols were identified, indicating potential health risks. Additionally, we uncovered previously understudied chemicals like the tire additive 2-mercaptobenzothiazole and specific organophosphate flame retardants. This study showcases the potential of our methodology as a valuable tool for large-scale cohort studies, providing insights into the association between contaminant exposure and the risk of male fertility impairments.
Surfactants are a group of amphiphilic molecules (i.e., having both hydrophobic and hydrophilic domains) that are a vital part of nearly every contemporary industrial process such as in agriculture, medicine, personal care, food, and petroleum. In general surfactants can be derived from (i) petroleum-based sources or (ii) microbial/plant origins. Petroleum-based surfactants are obvious results from petroleum products, which lead to petroleum pollution and thus pose severe problems to the environment leading to various ecological damages. Thus, newer techniques have been suggested for deriving surfactant molecules and maintaining environmental sustainability. Biosurfactants are surfactants of microbial or plant origins and offer much added advantages such as high biodegradability, lesser toxicity, ease of raw material availability, and easy applicability. Thus, they are also termed "green surfactants". In this regard, this review focused on the advantages of biosurfactants over the synthetic surfactants produced from petroleum-based products along with their potential applications in different industries. We also provided their market aspects and future directions that can be considered with selections of biosurfactants. This would open up new avenues for surfactant research by overcoming the existing bottlenecks in this field.
Hydrophobic ion pairing is a promising strategy to raise the lipophilic character of therapeutic peptides and proteins. In past studies, docusate, an all-purpose surfactant with a dialkyl sulfosuccinate structure, showed highest potential as hydrophobic counterion. Being originally not purposed for hydrophobic ion pairing, it is likely still far away from the perfect counterion. Thus, within this study, docusate analogues with various linear and branched alkyl residues were synthesized to derive systematic insights into which hydrophobic tail is most advantageous for hydrophobic ion pairing, as well as to identify lead counterions that form complexes with superior hydrophobicity. The successful synthesis of the target compounds was confirmed by FT-IR, ¹H-NMR, and ¹³C-NMR. In a screening with the model protein hemoglobin, monostearyl sulfosuccinate, dioleyl sulfosuccinate, and bis(isotridecyl) sulfosuccinate were identified as lead counterions. Their potential was further evaluated with the peptides and proteins vancomycin, insulin, and horseradish peroxidase. Dioleyl sulfosuccinate and bis(isotridecyl) sulfosuccinate significantly increased the hydrophobicity of the tested peptides and proteins determined as logP or lipophilicity determined as solubility in 1-octanol, respectively, in comparison to the gold standard docusate. Dioleyl sulfosuccinate provided an up to 8.3-fold higher partition coefficient and up to 26.5-fold higher solubility in 1-octanol than docusate, whereas bis(isotridecyl) sulfosuccinate resulted in an up to 6.7-fold improvement in the partition coefficient and up to 44.0-fold higher solubility in 1-octanol. The conjugation of highly lipophilic alkyl tails to the polar sulfosuccinate head group allows the design of promising counterions for hydrophobic ion pairing.
Statement of Significance
Hydrophobic ion pairing enables efficient incorporation of hydrophilic molecules into lipid-based formulations by forming complexes with hydrophobic counterions. Docusate, a sulfosuccinate with two branched alkyl tails, has shown highest potential as anionic hydrophobic counterion. As it was originally not purposed for hydrophobic ion pairing, its structure is likely still far away from the perfect counterion. To improve its properties, analogues of docusate with various alkyl tails were synthesized in the present study. The investigation of different alkyl residues allowed to derive systematic insights into which tail structures are most favorable for hydrophobic ion pairing. Moreover, the lead counter ions dioleyl sulfosuccinate and bis(isotridecyl) sulfosuccinate bearing highly lipophilic alkyl tails provided a significant improvement in the hydrophobicity of the resulting complexes.
Disodium lauryl sulfosuccinate (diSLSS) is an anionic surfactant, wherein a dodecyl chain and sodium sulfosuccinate are ester-bonded. The surfactant has two hydrophilic groups—sulfonic and carboxylic acid. The diSLSS reduced the surface tension of water to 26 mN m⁻¹. However, an inflection point indicating the critical micelle concentration in the surface-tension curve was not observed. According to dynamic light scattering measurements, the diSLSS formed ca. 160 nm of aggregates, and its zeta potential changed from −80 to −55 mV in the concentration range of 0.1–15 mmol L⁻¹. The aggregate exhibited a vesicle shape when imaged with a transmission electron microscope. In general, single-chain hydrocarbon-based surfactants rarely form vesicles in aqueous solutions. Therefore, the vesicle membranes were analyzed via small-angle X-ray scattering. The interlayer distance with the water layer for multilamellar vesicles was estimated to be 3 nm in a 15 mmol L⁻¹ diSLSS solution. Because the molecular length of diSLSS is approximately 2.2 nm, the molecular membrane for multilamellar vesicles is considered as an alternate layer, rather than an extended bilayer structure. Additionally, the strong electrostatic repulsion between the large hydrophilic groups indicates the existence of an alternate layer. The diSLSS has the merit that vesicles can be easily formed with the one component of surfactant from low concentration to 17 mmol L⁻¹.
Liquid-liquid equilibrium data were obtained for aqueous two-phase systems (ATPS) formed by polyethylene glycol (4000 or 6000 g mol⁻¹) + potassium phosphate (K2HPO4/H3PO4 or K2HPO4) + water. The effect of adding (0.05%) [w/w] of the dioctyl sulfosuccinate sodium (AOT) to the polymeric solution was studied. ATPS were determined using the turbidimetric method, at two pH values (7.0 and 9.3) and 298.15 K. Three tie-lines (TL) were determined using the lever rule. The effect of the variables pH, polymer molar mass and presence of the surfactant on binodal curves and TL were evaluated. In order to study the capacity of phase formation and the salting-out ability of the system-forming components, the salting-out effect and effective volume (EEV) of exclusion were determined. An increase in the biphasic region at the highest values of pH and molar mass of PEG was verified. Such results were correlated with the values of the parameters coefficient salting-out (k) and EEV. The increase in the system global composition caused an increase on the tie-lines length, varying in the range of (0.243–0.415). The different conditions determined had little effect on the tie-lines slope (STL). It was found that the presence of AOT in these ATPS caused a decrease in the EEV values of the systems (4285.916 − 6987.256).
Non-aqueous phase liquid (NAPL) remediation techniques using surfactants, such as enhanced pump and treat (also known as Surfactant-Enhanced Aquifer Remediation, "SEAR") and micellar flooding provide a faster and more efficient way to recover NAPL from the subsurface. Micellar flooding is a recovery technique that relies on the ability of surfactants to mobilize the NAPL phase by reducing the interfacial tension between the aqueous phase and the NAPL. The application of micellar flooding for NAPL recovery has been limited to laboratory studies and some pilot-scale field applications primarily due to concerns that the technology might lead to uncontrolled movement of NAPL. This paper presents results from a full-scale field application of the micellar flood process designed to mobilize and recover an LNAPL (Jet fuel) from a surficial sandy aquifer located at a tank facility in western Jutland, Denmark. Phase behavior and flow experiments were conducted with field samples to identify suitable surfactant formulations. A field-scale simulation model was developed that indicated that a line-drive pattern with hydraulic control wells would be optimal for NAPL recovery. In addition to monitoring during the field implementation, monitoring was conducted immediately after and for a period of >1 year. The field implementation resulted in >90% recovery (approximately 36,000 Kg of LNAPL) based on the mass balance using laser-induced fluorescence (LIF) and chemical soil analysis (total petroleum hydrocarbon or TPH and BTEX) data. Post-surfactant flood site monitoring consisted of sampling water from multi-levels and from recovery wells. Groundwater samples were analyzed for total petroleum hydrocarbon (TPH) and benzene, toluene, ethylbenzene and xylene (BTEX). The pre-treatment and post-treatment mass discharges were also monitored, which led to a relationship between mass discharge with the mass reduction in the source zone. Also, the mass discharge Γ-model commonly used for DNAPL modeling was successfully implemented for LNAPL remediation. Studies of field applications of surfactant remediation processes are not readily available; it is especially rare to present a study of micellar flooding implementation for full-scale remediation processes.
Sulfonation and sulfation are chemical reactions in which sulfur trioxide moiety is introduced into organic entities. These processes are utilized industrially for the manufacturing of chemical products that are used to produce anionic surfactants, cyclic intermediates, dyes, pigments, medicines, pesticides, sweeteners, lubricant additives, and polymeric specialty chemicals.
The focus in this article is on industrial processes suitable for the manufacturing of sulfated and sulfonated products. Considering the chemistry involved, processes are dependent on the choice of reagents, physical properties of feedstocks and derived products, product volume requirements, operational mode (batch, continuous), quality of derived products, by‐products and their disposal, and equipment and operating and equipment investment costs. Recent advances in sulfonation and sulfation technologies, including microchannel reactor technology as well as economic and environmental considerations are also discussed.
To develop an environmentally friendly and cost-effective water-based inorganic coating process for hydrophobic, polyolefin-based microporous separators, the effect of surfactants in an aqueous inorganic coating solution comprising alumina (Al2O3) on polyethylene (PE)-based microporous separators is investigated. By using a selected surfactant, i.e., disodium laureth sulfosuccinate (DLSS), the aqueous Al2O3 coating solution maintained a dispersed state over time and facilitated the formation of a uniform Al2O3 coating layer on PE separator surfaces. Due to the hydrophilic nature of the Al2O3 coating layers, the as-prepared, ceramic-coated PE separators had better wetting properties, greater electrolyte uptake, and larger ionic conductivities compared to those of the bare PE separators. Furthermore, half cells (LiMn2O4/Li metal) containing Al2O3-coated PE separators showed improved capacity retention over several cycles (93.6% retention after 400 cycles for Al2O3 coated PE separators, compared to 89.2% for bare PE separators operated at C/2) and rate capability compared to those containing bare PE separators. Moreover, because the Al2O3-coated layers are more thermally stable, the coated separators had improved dimensional stability at high temperatures (140 °C).
The present research work is associated with the fluorescence investigations of binary aqueous mixed surfactants solutions of anionic bis-sulfosuccinate gemini surfactant (BSGSMA1,8) and three different conventional surfactants anionic viz. sodium dodecyl sulphate (SDS), cationic viz. cetyl trimethyl ammonium bromide (CTAB) and non-ionic surfactant viz. Triton × 100. Steady-state fluorescence spectroscopy technique has been utilized to examine the micellization behavior of aqueous solution of pure myristyl alcohol based bis-sulfosuccinate anionic gemini surfactant (BSGSMA1,8) having flexible methylene chain [(CH2)8] as spacer group. Critical micelle concentration (CMC), Aggregation number (N) and micropolarity of pure and mixed surfactants systems were explored during the investigations. The results revealed the best synergism behavior of prepared gemini BSGSMA1,8 with SDS as compared to CTAB and Triton × 100. The maximum reduction in the value of pyrene intensity ratio (I1/I3) was observed for gemini and SDS mixed surfactant solution. On the other hand, the increased I1/I3 value of mixed gemini with Triton × 100 exhibited that mixed surfactant system of anionic gemini BSGSMA1,8 with non-ionic Triton × 100 is not as compact as other mixed surfactant systems. Aggregation number increased and micropolarity decreased with increased concentration of gemini surfactants.
Sulfosuccinate type anionic surfactants are classical ingredients for industrial applications. They are of great interest because of their excellent surfactant properties. Fatliquors prepared from sulfosuccinates have been effectively utilized in the leather industry, where the degree of sulfonation of the surfactant plays a crucial role in deciding performance. This paper reports on the study of factors such as the addition of phase transfer catalyst, non-ionic wetting emulsifier and co-solvent on the degree of sulfonation. Emusification power, zeta potential, surface tension and particle size were measured. Reaction conditions were optimized, based on the results. Fatliquors were prepared using different sulfosuccinates and applied on leather. The properties of resultant leathers were studied qualitatively and quantitatively, and SEM studies were carried out for the treated leathers. This work provides a basis for the development of better fatliquoring agents.
Sulfosuccinate esters are vastly used in different formulations as wetting agents and dispersants. Hemi-ester, diester, ethoxylated, and ethoxylated ester derivatives of maleic anhydride, maleic acid, and fumaric acid are converted to the saturated or corresponding sulfosuccinates by the reaction of the double bond with sodium bisulfite in basic media. The roles of anionic, cationic and non-ionic surfactants have been investigated. Appropriate surfactants have been applied in the absence of a peroxide initiator. The results obtained show increased reaction rates. Characterization of the products was performed by FTIR and 1HNMR spectroscopy. Ethoxylated isooctyl maleate derivative was used as the starting material and the sulfonation agents used were sodium bisulfite and meta bisulfite.
A series of cetyl alcohol based anionic bis-sulfosuccinate gemini surfactants (BSGSCA1,4; BSGSCA1,6 and BSGSCA1,8) with different spacer lengths was prepared using dibromoalkanes. The surfactant structure was elucidated using elemental analysis, Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR). Surface tension measurements were used to determine the critical micelle concentration (CMC), the surface tension at the CMC (γ
CMC), surface pressure at the CMC (π
CMC) and efficiency of adsorption (pC20). On the basis of surface studies, the CMC and γ
CMC decreases with increasing length of the spacer group. The micelle aggregation number, determined by fluorescence quenching studies, increases with increasing surfactant concentration above the CMC. The micropolarity in the micelle increases with increasing length of the spacer and decreases with increasing surfactant concentration.
A series of bis-sulfosuccinate anionic gemini surfactants were synthesized from meristyl alcohol (BSGSMA1,4; BSGSMA1,6 and BSGSMA1,8) containing 4, 6 and 8 methylene chains as different flexible spacer lengths. The chemical structures of synthesized geminis were confirmed by using spectroscopic analytical techniques viz. elemental analysis, fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy (NMR). Investigations were carried out to examine the effect of different spacer length and different salts (organic and inorganic) on surface and fluorescence properties of prepared gemini surfactants. The results of surface properties shown that surface tension at CMC (ϒCMC) and critical micelle concentration (CMC) were reduced and pC20 value was enhanced with increased spacer length. Fluorescence investigations were also revealed the significance of longer spacer with the concluded remarks of higher aggregation number and reduced micropolarity for BSGSMA1,8 having elongated flexible spacer. The results of salts studies had shown the better results for organic salts as compared to inorganic salts.
An effort has been made to synthesize, characterize and evaluate the fluorescence and surface active properties of dodecanol based bis-sulfosuccinate anionic gemini surfactants using α,ω-dibromo alkanes (BSGSLA1,4 ; BSGSLA1,6 and BSGSLA1,8). The authenticity of the chemical structures of the synthesized surfactants were confirmed by spectroscopic analytical techniques viz. elemental analysis, fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance spectroscopy(NMR). Numerous surface active properties viz. surface tension at cmc (ϒcmc), critical micelle concentration (cmc), efficiency of adsorption of surfactant (pC20), surface pressure at the cmc (πcmc), adsorption amount of surfactant (Гmax) and minimum area per molecule(Amin) were determined for synthesized surfactants. Low cmc value, larger pC20 consequently higher surface activity, higher Гmax value and lower Amin values for the surfactants with higher flexible spacer length [(CH2)8 ] were observed. The experimental data indicated that gemini surfactant with a larger hydrophobic flexible spacer [(CH2)8 ] was more readily able to form micelle which leads to a lower cmc value, larger aggregation number, and a more closely packed micelle structure. The results also indicated that greater aggregation number and higher micropolarity can be achieved when concentration of gemini surfactants was increased.
A new synthetic route to a mild surfactant disodium lauryl glucoside sulfosuccinate (AG-SS) containing two hydrophilic groups is described and its measured physicochemical properties reported. AG-SS was synthesized from lauryl glucoside reacted with maleic acid anhydride, and then sulfonated with sodium sulfite. The structure and composition of the product were defined by Fourier transform infrared spectroscopy and liquid chromatography–mass spectrometry. The surface activity measurement showed that the critical micelle concentration (CMC) and that the surface tension at CMC (γ
CMC) of AG-SS were 2.59 × 10−4 mol/L and 35.21 mN/m at 25 °C, respectively. AG-SS exhibited excellent water solubility eliminating the disadvantage of lauryl glucoside; its foaming ability was also remarkable.
The equilibrium and dynamic surface tension of three sulfosuccinate surfactants at the air/aqueous solution interface were investigated. Wilhelmy plate method was used to determine critical micelle concentration (CMC) and the equilibrium surface tension (γ
eq). The dynamic surface tensions in the range 10–100 s were measured by maximum bubble pressure method. The well-known Ward–Tordai equation was employed to analyze the adsorption of the sulfosuccinate surfactants. The parameters and effective diffusion coefficients (D
eff) of dynamic surface tension have been calculated and analyzed. The equilibrium surface tension results showed that disodium laureth (3) sulfosuccinate (AEO3-SS), disodium laureth (6) sulfosuccinate (AEO6-SS) and disodium alkyl ethoxy glucoside sulfosuccinate (AEG-SS) are surfactants possessing strong surface activity, adsorbing to the interface rapidly and their γ
eq values were in the range 25–32 mN/m. CMC of the three surfactants increases with the number of hydrophilic groups and AEO3-SS has the lowest CMC. According to the values of some dynamic surface tension parameters, AEG-SS is the most hydrophilic surfactant of them and AEO3-SS is energetically more favorable to adsorb to the interface than the others. According to Ward–Tordai equation, the D
eff values were calculated, the adsorption mechanism was diffusion controlled at short times and toward the end good evidence was found for an activated-diffusion mechanism with an energy barrier.
The oil spill dispersant, COREXIT 9500, used in the BP Deepwater Horizon oil spill, was analyzed by high-performance liquid chromatography-ion trap mass spectrometry with electrospray ionization. Two components present in the mixture, dioctyl sodium sulfonate (DOSS) and dipropylene glycol butyl ether (DGBE), were recovered from spiked ocean water samples. Compounds were isolated from ocean water spiked with COREXIT 9500 by solid phase extraction using C-18 cartridges prior to separation with high performance liquid chromatography-ion trap mass spectrometry using an acetonitrile and 0.1% formic acid gradient. Both compounds were identified using a simultaneous extraction procedure. Dioctyl sodium sulfonate is identified by negative electrospray-ion mode, and dipropylene glycol butyl ether by positive electrospray-ion mode. This method identifies trace levels of dispersants used in oil-spill cleanup efforts through the identification of two major components, which could provide validation for the correct identification of a dispersant mixture. This method was validated by recovering COREXIT components from spiked natural ocean water samples collected in the Gulf of Mexico. Oil-impacted ocean water samples were collected in Grand Isle, Louisiana at an oil-impacted beach, but no traces of COREXIT were identified.
The entitled monohydrolysis products, also known as α-ethylhexyl and β-ethylhexyl sulfosuccinate (EHSS), of the surfactant diisooctyl sulfosuccinate (DOSS) were synthesized in stable isotope-labelled form from [13C]4-maleic anhydride. Sodium [13C]4-1-carboxy-2-(2-ethylhexyloxycarbonyl)ethanesulfonate (α-EHSS) was prepared by the method of Larpent by reaction of 2-ethylhexan-1-ol with [13C]4-maleic anhydride followed by regioselective conjugate addition of sodium bisulfite to the resulting monoester (38% overall yield). The regiochemical outcome of bisulfite addition was confirmed by a combination of 13C/13C (incredible natural abundance double quantum transfer) and 1H/13C (heteronuclear multiple-bond correlation (HMBC)) NMR spectral correlation experiments. Sodium [13C]4-2-carboxy-1-(2-ethylhexyloxycarbonyl)ethanesulfonate (β-EHSS) was prepared in four steps by reaction of 4-methoxybenzyl alcohol with [13C]4-maleic anhydride, regioselective sodium bisulfite addition, N,N′-dicyclohexylcarbodiimide-mediated esterification with 2-ethylhexan-1-ol, and p-methoxybenzyl ester deprotection with trifluoroacetic acid (13% overall yield). The regiochemical outcome of the second synthesis was confirmed by a combination of 1JCC scalar coupling constant analysis and 1H/13C (HMBC) NMR spectral correlation. The materials prepared are required as internal standards for the liquid chromatography–mass spectrometry (LC-MS)/MS trace analysis of the degradation products of DOSS, the anionic surfactant found in Corexit, the oil dispersant used during emergency response efforts connected to the Deepwater Horizon oil spill of April 2010. Copyright
Furfural obtained from pentose containing biomass such as hemicelluloses is subjected to photooxygenation. The resulting hydroxyfuranone obtained in high yields undergoes acetalization with fatty alcohols. Using NaHSO3, surfactants are obtained by addition of a sulfonate group to α,β-unsaturated carboxyl or carbonyl compounds. Addition occurred either at the CC double bond (6) or at the aldehyde function (7). Compared to conventional surfactants of this type, the resulting compounds possess similar good detergent properties. In the case of compound family 6 and when compared to the corresponding alkylsulfate and alkylsulfonate surfactants, even lower critical micelle concentrations (CMC) are observed. Biodegradation of the new surfactants was determined according to the OECD Test guideline 301 F. Compounds of family 6 are biodegradable. Biodegradation of compounds of family 7 stopped after 10 days.
New gemini anionic surfactants were prepared from sodium salts of monoalkyl sulfosuccinate esters of ethylene glycol having variably long tails (C12, C16, C18) and dichloroethane. The chemical structures of the prepared surfactants were confirmed using different spectroscopic techniques. The surfaces tension values of the synthesized surfactants were measured at 25 °C individually or mixing at different molar fractions with ethoxylated alkylphenol. In all cases, mixed micellar aggregates were formed and critical micellar concentrations of binary mixtures containing different mole fractions of the surfactants were measured. The micellization processes of the individual and mixed surfactants were investigated. The effect of different alkyl chains of gemini anionic surfactants on properties of binary systems and molar ratio in the mixed aggregates were deduced. The critical micelle concentration of mixed surfactants shifted to lower values compared to those of the single surfactants. Effectiveness values increased with decreases in the mole fraction of gemini anionic surfactants. The negative values of interaction parameter (β) increased with increases in the chain length of anionic surfactants. The activity coefficient (f
1, f
2) and total minimum surface area of mixed solution were calculated. Also, the gemini anionic surfactants prepared have moderate antimicrobial activity towards bacteria and not active towards fungi.
Handbook of Surfactant
- . G Broze