Reduced Glycol Fatty Alcohol Ethoxylates and Reduced Glycol Sulfate Ethoxylated Surfactants

Abstract

A surfactant comprising an ethoxylated fatty alcohol having 100 ppm by weight or less of free glycol.A surfactant comprising a sulfated ethoxylated alcohol having 100 ppm by weight or less of sodium diethylene glycol monosulfate.

Description

[Technical Field]

[0001] This application is directed to a method for producing reduced glycol fatty alcohol ethoxylates, a method for producing reduced glycol sulfate ethoxylated surfactants, surfactants having 100 ppm by weight or less of free glycol, sodium diethylene glycol monosulfate, and products containing same. [Background technology]

[0002] Fatty alcohol ethoxylates are used in many industries.For example, they can be used as nonionic surfactants in detergents and cleansers.They can also be intermediates in the production of other surfactants by processes such as sulfation.Current processes used to produce fatty alcohol ethoxylates can contain unwanted by-products, which remain as part of fatty alcohol ethoxylate materials when sold or used, or can be further processed with fatty alcohol ethoxylates to produce different surfactants, resulting in additional or different unwanted by-products.These by-products can be problematic for the users of fatty alcohol ethoxylate raw materials themselves or the materials produced from fatty alcohol ethoxylate materials. Summary of the Invention [Problem to be solved by the invention]

[0003] Therefore, there is a need for fatty alcohol materials that have a better by-product profile. [Means for solving the problem]

[0004] One exemplary method includes producing a reduced glycol fatty alcohol ethoxylate material, comprising removing at least a portion of the glycols in the fatty alcohol ethoxylate material after formation of the fatty alcohol ethoxylate material.

[0005] Another exemplary method includes reducing the amount of ethylene glycol oligomers in an alcohol ethoxylate material, including extracting the ethylene glycol oligomers from the alcohol ethoxylate material.

[0006] These and other methods can be found in the Detailed Description section below. [Brief explanation of the drawings]

[0007] [Figure 1] 1 is a graph showing dioxane (ppm) formed over time (weeks) in feedstock aged at 30° C. [Figure 2] 1 is a graph showing dioxane (ppm) formed over time (weeks) in feedstock aged at 40° C. [Figure 3] 1 is a graph showing the rate of dioxane formation in ppm / week versus pH for a 15% active SLE1S composition at 50° C. [Figure 4] 1 is a graph showing the effect of pH on dioxane levels in 45% active ST2S feedstock after aging at 65° C. for 20 days. [Figure 5] 1 is a graph showing dioxane (ppm) formed over time (weeks) in feedstock aged at 50° C. [Figure 6] 1 is a graph of dioxane (ppm) formed in personal cleansing compositions (body washes) made with sodium trideceth-2 sulfate scrubbed at various temperatures over time (weeks). [Figure 7] 1 is a graph showing the amount of dioxane (ppm) formed over time (weeks) in three scrubbed 45% active sodium trideceth-2 sulfate surfactant raw material samples. [Figure 8]FIG. 1 is a graph showing normalized peak area concentration versus initial concentration of polyethylene glycol (n) monosulfate in samples of sodium laureth-1 sulfate (SLE1S), sodium laureth-3 sulfate (SLE3S), and sodium trideceth-2 sulfate (ST2S) versus stability sample temperature. [Figure 9] 1 is a graph of dioxane growth over time in a raw material sample plotting dioxane growth in sample, difference from initial (ppm) versus 2 month LCMS count (difference from ambient sample). [Figure 10] 1 is a graph of the glycol primary by-products found in a sample of 2-tridecyl alcohol ethoxylate. DETAILED DESCRIPTION OF THE INVENTION

[0008] Fatty alcohol ethoxylates are a class of compounds used in many different industries. One of the more common uses of this class of compounds is as surfactants. As surfactants, the properties of compounds in this class can vary widely, as they can be made from a wide range of materials. Briefly, fatty alcohol ethoxylates are generally produced by the reaction of fatty alcohols with ethylene oxide. The reaction generally occurs over a basic catalyst, such as an alkali metal hydroxide, allowing ethoxylate units to be continuously added to the fatty alcohol, resulting in a relatively broad distribution of fatty alcohol ethoxylates (FAEs) (n), where n has an average value of about 1 to about 20, and a distribution of ethoxylates for any value of n. The value of n is generally expressed on a molar basis as the ratio of moles of EO added to the reaction to moles of fatty alcohol added.

[0009] For example, specific catalysts can be used to tailor the distribution of ethoxylates for any given value of n to make it narrower and to modify properties. There are large classes of fatty alcohols suitable for ethoxylation, each of which can contribute a fatty alcohol ethoxylate with a different set of properties. The same can be true for the ethylene oxide component, in which case the chain length of this component can affect the properties of the final fatty alcohol ethoxylate. Some examples of fatty alcohol ethoxylates include 2-tridecyl alcohol ethoxylate (TDA-2), alcohol ethoxylate-2 (AE-2), 3-tridecyl alcohol (TDA-3), alcohol ethoxylate-1 (AE-1), alcohol ethoxylate 1.8 (AE-1.8), and combinations thereof.

[0010] The reaction of fatty alcohols with ethylene oxide can also produce by-products, i.e., compounds that are not fatty alcohol ethoxylates. One class of materials that can be by-products of this reaction is free glycols, specifically ethylene glycol oligomers. Free glycols are ethylene oxide addition products, i.e., oligomers of ethylene oxide that are not attached to fatty alcohols. Generally, FAEs can contain about 0.2% to about 1.5% by weight of free glycols, or about 0.5% to about 1% by weight of free glycols. These free glycols can interfere with the ability to incorporate alcohol ethoxylates, particularly when it is desired to limit these types of by-product materials in the final product.

[0011] However, another problem exists. Fatty alcohol ethoxylates may be further reacted with gaseous sulfur trioxide (SO₃) in a falling film reactor (FFR) or with chlorosulfonic acid (HSOCl) in a batch process to produce other compounds, such as alcohol ethoxylated sulfate surfactants (AES), followed immediately by a neutralization step to produce an aqueous surfactant paste or solution having a predetermined pH of about pH 5 to about pH 13. The surfactant is generally neutralized to an active surfactant concentration of about 25% to about 70% by weight. These ethoxylated sulfate surfactants may include, for example, sodium laureth(n) sulfate (SLEnS) and sodium trideceth(n) sulfate (STnS), where n is generally 0.5 to 4. Exemplary SLEnS surfactants can include sodium laureth-1 sulfate, sodium laureth-1.8 sulfate, sodium laureth-2 sulfate, sodium laureth-2.5 sulfate, and sodium laureth-3 sulfate. Exemplary STnS surfactants can include sodium trideceth-2 sulfate and sodium trideceth-3 sulfate.

[0012] During sulfation, primary by-products such as free glycols are sulfated to form secondary by-products, glycol monosulfates and disulfates. In addition, under SO3-rich conditions, cleavage of EO oligomers, whether free glycols, FAEs, or sulfated FAEs, also produces secondary by-products, such as the aforementioned glycol sulfates and disulfates, as well as generally longer glycol mono- and disulfates. Occasionally, cyclization of certain by-products can occur to form secondary by-products, such as 1,4-dioxane. In recent years, there has been a desire to limit the amount of 1,4-dioxane.

[0013] 1,4-dioxane is a known secondary by-product of the combination of ethoxylation process and sulfonation process to form surfactants (see Norman, Sulfonation and Sulfation Processes, The Chemithon Corporation, 1997).Although 1,4-dioxane exists at very low levels in surfactants or surfactant-containing cleansing products, and can often be less than 50 ppm, it is currently desired to further reduce and / or eliminate it from surfactants and / or surfactant-containing products.One process for removing 1,4-dioxane from surfactants is to use a dioxane removal system to scrub 1,4-dioxane from ethoxylated sulfate surfactant raw materials.Some exemplary methods for scrubbing dioxane can be found in, for example, U.S. Application No. 17 / 184634 and U.S. Patent No. 4,285,881. Scrubbing dioxane utilizes specialized equipment that can be expensive and energy intensive, and utilizes additional processing time, all of which results in higher production costs for manufacturers of surfactants and surfactant-containing products.

[0014] Research into the level of 1,4-dioxane in products has led to several findings. First, it is understood that in the production of ethoxylated sulfate surfactants, the sulfation reaction is promoted by using more than one mole of sulfate source to the fatty alcohol feedstock, resulting in a dramatic increase in the production of 1,4-dioxane (see Norman, Sulfonation and Sulfation Processes, The Chemithon Corporation, 1997). To prevent the formation of additional 1,4-dioxane, many surfactant raw material manufacturers may not fully sulfate the FAE feedstock to 100% completion, for example, they may carry out this reaction at a molar ratio of less than about 1.03:1, and carry out the reaction under a set of conditions that result in sulfation completion of only about 96%, 97%, or 98%.

[0015] Second, when ethoxylated sulfate surfactant raw materials are transported at high temperatures or placed in heated tanks at manufacturing plants while waiting for incorporation into products, the level of dioxane can increase substantially. The reason for this was not understood, but the consequences needed to be mitigated. Therefore, to mitigate this phenomenon, such raw materials were assigned a shelf life and used as soon as possible at manufacturing plants. However, this alone is insufficient to meet the current desired level of dioxane in the final product.

[0016] As part of an investigation into potential solutions to meet the desired dioxane level, the pH of the surfactant raw material was studied. SLE1S 70% active surfactant paste was commercially obtained with a pH of 12.97 and an initial dioxane concentration of 5.76 ppm (8.2 ppm at 100% active). A portion of the paste was sealed in a container, and the remaining paste was neutralized to pH 7.8 using citric acid and placed in a sealed container. The container was stored at 50°C or 65°C, and the dioxane was measured periodically. All pH values ​​were obtained using a 10% dilution of the raw material with 90% water at 21°C. As can be seen in Table 1, dioxane growth from the initial time point was substantially lower at the neutral pH of the 70% active surfactant paste. The numbers in parentheses are calculated on a 100% active basis.

[0017] [Table 1]

[0018] Thus, it appears that AES raw materials at pH ≥ approximately 12 generate 1,4-dioxane fairly quickly when stored at typical temperatures (such as 30-40°C). This is especially true when surfactant activity is ≥ 45%; see Figures 1 and 2. However, the same trend can be found, albeit to a lesser extent, at lower concentrations. For example, a 15% active SLE1S paste is subjected to aging at 50°C. The results in Figure 3 show the relationship between pH and the amount of dioxane growth over time; specifically, a sharp increase in dioxane formation begins at approximately pH 9. The problem is also more apparent at higher temperatures (see Figures 1 and 2).

[0019] We found that when the pH of these surfactants was controlled at about 7 to about 8 (as a 10% solution) by adding an organic or inorganic buffer, the growth rate of 1,4-dioxane significantly slowed (see Table 1). This helps ensure that the surfactant pastes can be stored, handled, and transported for much longer periods. For example, this allows the shelf life of these materials to increase from less than four weeks to more than two months, which in turn allows for more flexibility in transporting and storing these surfactant raw materials.

[0020] While a neutral pH of about 7 to about 8 has its advantages, one of the primary reasons that the pH of surfactant pastes is currently maintained at a pH of about 12 or higher is that it is self-preserving and therefore does not require a separate preservative. Looking at the pH curves with reference to Figures 3 and 4, there is a conversion at higher activity percentages of ST2S, and dioxane growth does not continue to increase at a sustained rate up to pH 10.5 and above, still remaining similar to levels seen at pH 9 or pH 11. This allows room to lower the pH to reduce the growth rate of dioxane in the feedstock, while still utilizing a pH that still has some minimal hostility, such as pH 10-11.

[0021] An example of a buffering agent for use in neutralizing or reducing the pH of surfactant raw materials is an organic buffer. Organic buffers may include, for example, organic acids, carbonates, fatty acids, or combinations thereof. Examples of organic acids include citric acid, malic acid, lactic acid, acetic acid, ascorbic acid, tartaric acid, oxalic acid, benzoic acid, sorbic acid, or combinations thereof. Examples of carbonates may include sodium carbonate, sodium bicarbonate, zinc carbonate, potassium carbonate, potassium bicarbonate, or combinations thereof. Examples of fatty acid buffers may include lauric acid, myristic acid, stearic acid, oleic acid, palmitic acid, or combinations thereof. These buffers generally operate in different pH ranges. For example, organic acids operate at about pH 5-8, fatty acids at about pH 6-10, and carbonates at about pH 8-10.5. These buffers may be used to allow for the use of a suitable base (e.g., NaOH) in a practical manner to target the appropriate pH.

[0022] To maintain the ability to use fatty alcohol ethoxylate and ethoxylated sulfate surfactants in cleansing products, as another part of the investigation into potential solutions for meeting the desired dioxane level, raw material scrubs were investigated to determine whether they were sufficient to meet the desired dioxane level. Samples of raw materials such as sodium laureth-1 sulfate (SLE1S), sodium laureth-3 sulfate (SLE3S), and sodium trideceth-2 sulfate (ST2S) at various activity levels were scrubbed using industry standard methods. The samples had a pH of >12 (measured using a 10% aqueous solution of the raw materials). Experimental body washes were formulated with sodium trideceth-2 sulfate surfactant, with dioxane scrubbed out. These samples were then subjected to aging studies to determine whether dioxane levels remained stable over time after scrubbing.

[0023] As can be seen from Figures 1, 2, and 5, three different raw materials (SLE1S, SLE3S, and ST2S) at various activity levels all showed an increase in dioxane over time. Thus, dioxane is produced in significant amounts in the raw materials that were scrubbed. The same is true for the body wash composition formulated with ST2S (9.6% actives) scrubbed at a pH of about 6. This is visually shown in Figure 6.

[0024] With longer storage times and higher temperatures, the rate of dioxane formation slows, suggesting that dioxane may be formed from components in the feedstock that are then used up. The characteristic pattern of regrowth is a plateau, as if using up an unknown reactant (see Figure 7). Because growth is likely caused by components in the feedstock, the reaction by-products of both the ethoxylation and sulfation reactions are reviewed to determine potential unknown reactants that may enable dioxane regrowth. The primary by-products, i.e., from the ethoxylation reaction, are primarily free glycols, such as ethylene glycol oligomers. The structure of ethylene glycol oligomers is generally H—(O—CH2—CH2) n -OH, where n represents the average number of ethylene oxide units in the oligomer chain. Values ​​of n from 2 to 30 may be, for example, primary reaction by-products. The value of n in the oligomer chain may be, for example, from 2 to about 25, from 2 to about 20, from 2 to about 15, from 2 to about 10, or from 2 to about 5.

[0025] As explained above, these may undergo reactions during the sulfation process to produce secondary by-products. Secondary by-products are believed to include, for example, 1,4-dioxane, diethylene glycol monosulfate, diethylene glycol disulfate, and those by-products formed as a result of the dissolution of FAEs and AESs. Secondary by-products are studied to determine those most likely contributing to the increase in dioxane over time in the ethoxylated sulfate surfactant feedstock.

[0026] Because the free glycol remains in the fatty alcohol ethoxylate and the terminal hydroxyl is largely sulfated in the falling film reactor simultaneously with fatty alcohol ethoxylate sulfation, the transition states of potential reactants are compared. As seen in Table 2 below, diethylene glycol monosulfate is the only species that demonstrates a negative ΔG for the diethylene glycol monosulfate to dioxane transition. Therefore, it is the only species identified that demonstrates that this reaction is spontaneous at high pH and is the most likely and most troublesome by-product for dioxane growth in ethoxylated sulfate surfactants.

[0027] [Table 2]

[0028] This is supported by studies of the concentration of free glycol (n) with n values ​​ranging from 2 to 8 after two months of aging at 25-50°C. The observations are plotted in Figure 8 for seven glycol sulfates, for three raw materials (SLE1S, ST2S, and SLE3S), and at four temperatures. As can be seen from Figure 8, the concentrations of the tested glycol (n) monosulfates are relatively stable, suggesting that they are not being used up as reaction products for the formation of dioxane. The one exception is diethylene glycol monosulfate, which shows a significant decrease in concentration over the same period at elevated temperatures compared to the ambient control.

[0029] To further support this mechanism, we investigate the relationship between diethylene glycol monosulfate loss and dioxane growth in the aged feedstock. To demonstrate this, we compare the diethylene glycol monosulfate loss at each temperature relative to its ambient control with the temporal increase in dioxane levels in the same sample. This allows for a direct comparison of diethylene glycol monosulfate loss and dioxane growth over two months of aging. Figure 9 compares the dioxane growth over time for three surfactant feedstocks at different temperatures (temperatures not shown) against the relative loss of diethylene glycol monosulfate at elevated temperatures compared to the ambient aged (control) sample for each surfactant. The relationship in Figure 9 experimentally verifies that diethylene glycol monosulfate spontaneously converts to 1,4-dioxane.

[0030] Now that the likely cause has been identified, what is the solution to preventing unwanted dioxane formation? First, we examine how diethylene glycol monosulfate is formed. It is believed that some diethylene glycol monosulfate forms when the primary glycol by-product from the ethoxylation reaction is sulfated during the sulfation process. We demonstrate this by sulfated a primary linear fatty alcohol mixed with 1 wt% polyethylene glycol 400 (PEG400) (PEG400 represents the free glycol) in an FFR. The results are compared to a similar fatty alcohol ethoxylate, laureth-1, sulfated under the same conditions, as shown in Table 3. The added glycol contributes approximately 2% of the formation of diethylene glycol monosulfate and approximately 30% of the dioxane formed during sulfation.

[0031] [Table 3]

[0032] Therefore, if at least a portion of the glycol is removed from the fatty alcohol ethoxylate before it is used to form the ethoxylated sulfate surfactant, there should be less formation of dioxane itself and dioxane precursors such as diethylene glycol monosulfate and / or diethylene glycol disulfate, and correspondingly less dioxane formation during aging. Removal of at least a portion of the glycol by-products will result in the formation of low-glycol fatty alcohol ethoxylates, i.e., fatty alcohol ethoxylates having less than about 0.25%, 0.2%, 0.15%, and / or 0.1% free glycol.

[0033] One way to remove at least a portion of the free glycol from the fatty alcohol ethoxylate is by an extraction process. Extraction can be carried out, for example, with a solvent. Solvents can include, for example, water, ethanol, and other alcohols, ethyl acetate and other esters, and other polar solvents. The solvent can be added at a level sufficient to solubilize the glycol in the solvent. This can be, for example, about 10% to about 100%, about 10% to about 90%, 15% to about 80%, about 15% to about 70%, about 15% to about 60%, about 25% to about 55%, and / or about 30% to about 50% by weight of the fatty alcohol ethoxylate material. The addition of solvent is a balancing act between the desire to solubilize more glycol and the amount of alcohol ethoxylate lost during the extraction process.

[0034] The extraction may further include the use of electrolytes such as salts. Examples of salts suitable for use during extraction include sodium chloride, potassium chloride, sodium citrate, potassium citrate, and combinations thereof. The addition of salts may aid in the separation of the solvent-containing layer from the surfactant-containing layer.

[0035] The extraction can be carried out at elevated temperatures, such as above the gel point of the fatty alcohol ethoxylate / solvent mixture. The extraction temperature can be, for example, about 65°C to about 90°C, about 67°C to about 88°C, about 70°C to about 90°C, 65°C to about 75°C, about 67°C to about 70°C, about 70°C, and / or about 80°C.

[0036] If the extraction is carried out with a solvent, the solvent may need to be removed from the fatty alcohol ethoxylate raw material. To remove the solvent from the fatty alcohol ethoxylate raw material, for example, the mixture can be dried. The mixture can be dried using an oven, air, heated air, vacuum drying, etc. Exemplary extraction and drying processes can be found below.

[0037] A sample of a commercially available ethoxylated alcohol surfactant, 2-tridecyl alcohol ethoxylate, was measured for glycol, one of its primary by-products. As can be seen in Figure 10, the sample contains a large amount of glycol. While the highest concentration is PEG-12 or greater, PEG-10 through PEG-2 are also present. Because PEG-2 is present in the sample above the detection level but below the limit of quantitation, the PEG-2 value in Figure 10 is an estimate. The sample is then subjected to an extraction process. First, the sample is dissolved in ethyl acetate. The glycol is then extracted with an aqueous solution of sodium chloride. This extraction is repeated three times. As can be seen in Table 4, the glycol level is significantly reduced after only one wash and is undetectable after the second wash. The times are corrected for differences in concentration. Therefore, it is possible to remove at least a portion of the free glycol primary by-product.

[0038] [Table 4]

[0039] Thus, the amount of glycol in a reduced glycol fatty alcohol material can be, for example, from about 0 ppm to about 100 ppm, from about 0 ppm to about 90 ppm, from about 0 ppm to about 80 ppm, from about 0 ppm to about 70 ppm, from about 0 ppm to about 60 ppm, from about 0 ppm to about 50 ppm, from about 0 ppm to about 40 ppm, from about 0 ppm to about 30 ppm, from about 0 ppm to about 20 ppm, and / or from about 0 ppm to about 10 ppm. A reduced glycol fatty alcohol material is one in which the amount of glycol by-products has been reduced after formation of the glycol fatty alcohol material. Thus, a fatty alcohol material within these ranges without undergoing a process to remove at least a portion of the glycol by-products would not be considered a reduced glycol sulfate fatty alcohol material. However, if that same material were to undergo a process to remove at least a portion of the glycol by-products, and that process resulted in a reduction of the by-products, the resulting material would be a reduced glycol fatty alcohol material. The amounts of glycol listed above are adjusted for 100% surfactant activity.

[0040] The amount of glycol in the reduced glycol fatty alcohol material can be at least 10% by weight less, between about 10% by weight and about 100% by weight less, between about 15% by weight and about 95% by weight, between about 15% by weight and about 90% by weight, between about 15% by weight and about 85% by weight, between about 20% by weight and about 95% by weight, between about 20% by weight and about 90% by weight, between about 20% by weight and about 85% by weight, between about 25% by weight and about 95% by weight, between about 25% by weight and about 90% by weight, between about 25% by weight and about 85% by weight, between about 25% by weight and about 75% by weight, between about 30% by weight and about 95% by weight, between about 30% by weight and about 90% by weight, between about 30% by weight and about 85% by weight, and / or between about 30% by weight and about 75% by weight less than that of the fatty alcohol material prior to removal of at least a portion of the glycol.

[0041] In addition to the above, it is believed that removing at least a portion of the glycol in the ethoxylated fatty alcohol prior to sulfation results in an ethoxylated sulfate surfactant with less glycol sulfate, also known as a reduced glycol sulfate ethoxylated sulfate surfactant. Laureth-1 surfactant can be sulfated to produce sodium laureth-1 sulfate (SLE1S). As can be seen in Table 5 below, the SLE1S surfactant (control) made from laureth-1 in which at least a portion of the ethylene glycol oligomers have not been removed prior to sulfation contains more diethylene glycol monosulfate than the SLE1S sample made from laureth-1 in which at least a portion of the ethylene glycol oligomers have been removed by extraction (washing) prior to sulfation.

[0042] [Table 5]

[0043] Thus, a method for producing a reduced glycol sulfate ethoxylated sulfate surfactant may include removing at least a portion of the glycol in the ethoxylated fatty alcohol prior to sulfation to produce a reduced glycol sulfate ethoxylated sulfate surfactant. Another method for producing a reduced glycol sulfate ethoxylated surfactant may include sulfating a reduced glycol fatty alcohol.

[0044] A reduced glycol sulfate ethoxylated sulfate surfactant is one that has less glycol sulfate than would be produced by ethoxylated fatty alcohol surfactants prior to removal of at least a portion of the glycol by-products. The initial amount of glycol sulfate before aging may vary depending on the surfactant. For example, ethoxylated surfactants with only one ethoxylate group will have a lower initial amount of diethylene glycol sulfate after the ethoxylation process than those ethoxylated surfactants with multiple ethoxylate units. In fact, the initial amount of diethylene glycol monosulfate will increase with the addition of each ethoxylate group in the surfactant. The results for exemplary surfactants are shown in Table 6.

[0045] [Table 6]

[0046] Because the initial level of diethylene glycol monosulfate before aging increases as the number of ethoxylate units increases, the ranges of glycol sulfate and diethylene glycol sulfate amounts described below can be adjusted to account for the difference in initial values ​​to reflect the actual reduction from an ethoxylated surfactant that does not remove at least a portion of the glycol by-products. Thus, a surfactant within these ranges without undergoing a process to remove at least a portion of the glycol sulfate by-products would not be considered a reduced glycol sulfate ethoxylated surfactant. However, if that same surfactant were to undergo a process to remove at least a portion of the glycol sulfate by-products, and that process resulted in a reduction of that by-product, the resulting surfactant would be a reduced glycol sulfate ethoxylated sulfate surfactant.

[0047] The reduced glycol sulfate ethoxylated sulfate surfactant may have less than about 100 ppm by weight of diethylene glycol monosulfate. The amount of diethylene glycol monosulfate in the reduced glycol ethoxylated sulfate surfactant is from about 0 ppm to about 100 ppm, from about 0 ppm to about 90 ppm, from about 0 ppm to about 80 ppm, from about 0 ppm to about 70 ppm, from about 0 ppm to about 60 ppm, from about 0 ppm to about 50 ppm, from about 0 ppm to about 40 ppm, from about 0 ppm to about 30 ppm, from about 0 ppm to about 20 ppm, or from about 0 ppm to about 10 ppm.

[0048] The reduced glycol sulfate ethoxylated sulfate surfactant may have less than about 300 ppm by weight of diethylene glycol disulfate. The reduced glycol sulfate ethoxylated sulfate surfactant may have less than about 250 ppm of diethylene glycol disulfate. The reduced glycol sulfate ethoxylated sulfate surfactant may have less than about 400 ppm of total diethylene glycol sulfate (monosulfate and disulfate combined). The amount of diethylene glycol disulfate in the reduced glycol sulfate ethoxylated sulfate surfactant is about 0 ppm to about 300 ppm, about 0 ppm to about 275 ppm, about 0 ppm to about 250 ppm, about 0 ppm to about 200 ppm, about 0 ppm to about 150 ppm, about 0 ppm to about 100 ppm, about 0 ppm to about 75 ppm, or about 0 ppm to about 50 ppm. The ppm amounts of glycol sulfate and diethylene glycol sulfate mentioned above are adjusted to a surfactant activity of 100.

[0049] Another method for producing reduced glycol sulfate ethoxylated surfactants can involve sulfating reduced glycol fatty alcohols to a sulfation completion rate of less than 100%. The completion rate can be, for example, 99%, 98%, 97%, 96%, 95%, 94%, 93%, 92%, 91%, 90%, 89%, 88%, etc. For example, completion can be reduced by utilizing a lower molar ratio of SO3 in the feedstock. The average molecular weight of the feedstock can be determined by measuring its hydroxyl number before sulfation. Because SO3 catalyzes dioxane formation under reactor conditions (see the Chemithon reference cited above), reducing the SO3 molar ratio can minimize excess reactor (FFR) dioxane formation. Reduced glycol fatty alcohols can be produced according to any of the aforementioned methods. For example, reduced glycol fatty alcohols can be made by removing at least a portion of the glycol by-product after the ethoxylation process. This can be done, for example, by extracting at least a portion of the glycol by-product. Glycol by-products are discussed above.

[0050] Reduced glycol sulfate surfactants can include, for example, sodium laureth(n) sulfate and sodium trideceth(n) sulfate. n can have a value of 0.5 to about 4. For example, the value of n can be about 1 to about 3, about 1.8, and / or about 2.5.

[0051] In addition to providing a solution to help combat regrowth, the solution can be used in combination with dioxane removal techniques to both reduce dioxane levels and the likelihood of regrowth. For example, a method for producing a fatty alcohol ethoxylate material can include scrubbing a reduced glycol alcohol ethoxylate to remove at least a portion of the 1,4-dioxane from the fatty alcohol ethoxylate material, thereby producing a scrubbed reduced glycol fatty alcohol ethoxylate. Another example includes a method for producing an ethoxylated sulfate surfactant, which can include scrubbing a reduced glycol sulfate ethoxylated surfactant to remove at least a portion of the 1,4-dioxane from the surfactant, thereby producing a scrubbed reduced glycol sulfate ethoxylated surfactant. Scrubbing can be performed by the processes discussed above or as known in the art.

[0052] Reduced glycol alcohol ethoxylates and reduced glycol sulfate ethoxylated surfactants can be produced as discussed above. For example, after completion of the reaction to form the fatty alcohol ethoxylate material, at least a portion of the glycol by-products are removed from the fatty alcohol ethoxylate material. The glycol can include, for example, ethylene glycol oligomers. Ethylene glycol oligomers include HO(CH2CHO) n H, where n is from 2 to about 30. At least a portion of the glycols can be removed, for example, by extraction.

[0053] Reduced glycol ethoxylated fatty alcohol surfactants, scrubbed glycol ethoxylated fatty alcohol surfactants, reduced glycol sulfate ethoxylated sulfate surfactants, and scrubbed reduced glycol sulfate ethoxylated sulfate surfactants can be used in cleansing compositions. More detailed information regarding exemplary cleansing compositions is below.

[0054] As used herein, diethylene glycol monosulfate and diethylene glycol disulfate refer to the sodium and disodium salts, respectively. The molecular weight of diethylene glycol monosulfate sodium salt is 208.2 g / mol, and that of diethylene glycol disulfate disodium salt is 310.2 g / mol.

[0055] Cleansing Composition 1. Personal cleansing composition Rinse-off personal cleansing compositions can be provided in many forms. For example, the personal cleansing composition can be in a liquid form, such as a body wash, shampoo, conditioning shampoo, shower gel, facial cleanser, cleansing milk, in-shower body moisturizer, liquid hand soap, pet shampoo, shaving preparation, etc. The rinse-off personal cleansing composition can also be in a solid form, such as a bar soap or semi-solid form, or in a semi-solid form, such as a paste or gel. The solid cleansing composition can also be in many shapes, such as a rectangular shape, or in a powder or pellet form. Furthermore, the solid and semi-solid forms can be combined with a substrate to form an article, as described in more detail in U.S. Patent Application Publication Nos. 2012 / 0246851, 2013 / 0043145, 2013 / 0043146, and 2013 / 0043147.

[0056] Rinse-off cleansing compositions generally include a cleansing ingredient, such as a detersive surfactant and / or soap. The amount of cleansing ingredient likely depends on the form, as better described below. Regardless of form, the cleansing composition may contain other ingredients, such as structurants, humectants, fatty acids, inorganic salts, antimicrobial agents, actives, preservatives, etc.

[0057] A. Liquid Personal Cleansing Composition Exemplary liquid rinse-off personal cleansing compositions can include an aqueous carrier, which can be present at a level of about 5% to about 95%, about 10% to about 90%, about 20% to about 80%, about 30% to about 75%, and / or about 40% to about 75%. The aqueous carrier can include water or a miscible mixture of water and an organic solvent. Non-aqueous carrier materials can also be used.

[0058] Such rinse-off personal cleansing compositions may include one or more detersive surfactants. The detersive surfactant component may be included to provide cleaning performance to the product. The detersive surfactant component may then include an anionic detersive surfactant, a zwitterionic detersive surfactant, an amphoteric detersive surfactant, or a combination thereof. A representative, non-limiting list of anionic surfactants for use in the compositions includes ammonium lauryl sulfate, ammonium laureth sulfate, triethylamine lauryl sulfate, triethylamine laureth sulfate, triethanolamine lauryl sulfate, triethanolamine laureth sulfate, monoethanolamine lauryl sulfate, monoethanolamine laureth sulfate, diethanolamine lauryl sulfate, diethanolamine laureth sulfate, lauryl monoglyceride sodium sulfate, sodium lauryl sulfate, sodium laureth sulfate, potassium lauryl sulfate, potassium laureth sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, ammonium lauroyl sulfate, sodium cocoyl sulfate, sodium lauroyl sulfate, potassium cocoyl sulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine cocoyl sulfate, monoethanolamine lauryl sulfate, sodium tridecylbenzenesulfonate, sodium dodecylbenzenesulfonate, sodium cocoyl isethionate, and combinations thereof. In one example, the anionic surfactant may be sodium lauryl sulfate or sodium laureth sulfate. The concentration of the anionic surfactant component in the product may be sufficient to provide the desired cleaning and / or lathering performance, generally ranging from about 2% to about 50%.

[0059] Amphoteric detersive surfactants suitable for use in rinse-off personal cleansing compositions are well known in the art, and include surfactants that are generally described as derivatives of aliphatic secondary and tertiary amines, where the aliphatic radical can be linear or branched, the aliphatic substituent can contain about 8 to about 18 carbon atoms, and one carbon atom can contain an anionic water-solubilizing group, such as carboxy, sulfonate, sulfate, phosphate, or phosphonate.Examples of compounds that fit this definition can be sodium 3-dodecylaminopropionate, sodium 3-dodecylaminopropanesulfonate, N-alkyltaurine, such as that prepared by reacting dodecylamine with sodium isethionate according to the teachings of U.S. Patent No. 2,658,072, N-higher alkylaspartic acid, such as that produced according to the teachings of U.S. Patent No. 2,438,091, and the products described in U.S. Patent No. 2,528,378. Other examples of amphoteric surfactants may include sodium lauroamphoacetate, sodium cocoamphoacetate, disodium lauroamphoacetate, disodium cocoamphoacetate, and mixtures thereof. Amphoacetates and diamphoacetates may also be used.

[0060] Zwitterionic detersive surfactants suitable for use in rinse-off personal cleansing compositions are well known in the art and include surfactants broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, where the aliphatic radical can be straight or branched, the aliphatic substituent can contain from about 8 to about 18 carbon atoms, and one carbon atom can contain an anionic group, such as carboxy, sulfonate, sulfate, phosphate, or phosphonate. Other zwitterionic surfactants can include betaines, including cocoamidopropyl betaine.

[0061] Personal cleansing compositions can include one or more phases. Such personal cleansing compositions can include a cleansing phase and / or a benefit phase (i.e., a single-phase or multi-phase composition). Each of the cleansing phase or benefit phase can include various ingredients. The cleansing phase and benefit phase can be a blend, separate, or a combination thereof. The cleansing phase and benefit phase can also be patterned (e.g., striped).

[0062] The cleansing phase of the personal cleansing composition may include at least one surfactant. The cleansing phase may be an aqueous structured surfactant phase and may be present at about 5% to about 20% by weight of the personal cleansing composition. Such a structured surfactant phase may include sodium trideceth(n) sulfate (hereinafter STnS), where n defines the average moles of ethoxylation. n may range, for example, from about 0 to about 3, from about 0.5 to about 2.7, from about 1.1 to about 2.5, from about 1.8 to about 2.2, or n may be about 2. When n is less than 3, STnS may provide improved stability, improved compatibility of benefit agents within the personal cleansing composition, and increased mildness of the personal cleansing composition; such described benefits of STnS are disclosed in U.S. Pat. No. 9,750,674.

[0063] The cleansing phase may also include at least one of an amphoteric surfactant and a zwitterionic surfactant. Suitable amphoteric or zwitterionic surfactants may include those described in U.S. Patent Nos. 5,104,646 and 5,106,609 (in addition to those cited herein).

[0064] The cleansing phase may include a structuring system, which may optionally include a nonionic emulsifier, optionally from about 0.05% to about 5% by weight of the personal cleansing composition of an associative polymer, and an electrolyte.

[0065] The personal cleansing composition may optionally be free of sodium lauryl sulfate (hereinafter referred to as SLS) and may contain at least 70% lamellar structure. However, the cleansing phase may contain at least one surfactant, and at least one surfactant may include SLS. Suitable examples of SLS are described in U.S. Patent Application Publication No. 2010 / 0322878.

[0066] As described herein, the rinse-off personal cleansing composition may also include a benefit phase. The benefit phase may be hydrophobic and / or anhydrous. The benefit phase may also be substantially free of surfactants. The benefit phase may also include a benefit agent. Specifically, the benefit phase may include from about 0.1% to about 50% benefit agent by weight of the personal cleansing composition. The benefit phase may also include less benefit agent, for example, from about 0.5% to about 20% benefit agent by weight of the personal cleansing composition. Examples of suitable benefit agents may include petrolatum, glyceryl monooleate, mineral oil, natural oils, and mixtures thereof. Additional examples of benefit agents may include water-insoluble or hydrophobic benefit agents. Other suitable benefit agents are described in U.S. Patent No. 9,750,674.

[0067] Non-limiting examples of glycerides suitable for use as hydrophobic skin benefit agents herein may include castor oil, safflower oil, corn oil, walnut oil, peanut oil, olive oil, cod liver oil, almond oil, avocado oil, palm oil, sesame oil, vegetable oil, sunflower seed oil, soybean oil, vegetable oil derivatives, coconut oil and derivatized coconut oil, cottonseed oil and derivatized cottonseed oil, jojoba oil, cocoa butter, and combinations thereof.

[0068] Non-limiting examples of alkyl esters suitable for use as hydrophobic skin benefit agents herein can include isopropyl esters of fatty acids and long chain esters of long chain (i.e., C10-C24) fatty acids, such as cetyl ricinoleate, non-limiting examples of which can include isopropyl palmitate, isopropyl myristate, cetyl riconoleate, and stearyl riconoleate. Other examples may include hexyl laurate, isohexyl laurate, myristyl myristate, isohexyl palmitate, decyl oleate, isodecyl oleate, hexadecyl stearate, decyl stearate, isopropyl isostearate, diisopropyl adipate, diisohexyl adipate, dihexyldecyl adipate, diisopropyl sebacate, acyl isononanoate lauryl lactate, myristyl lactate, cetyl lactate, and combinations thereof.

[0069] Non-limiting examples of polyglycerol fatty acid esters suitable for use as hydrophobic skin benefit agents herein can include decaglyceryl distearate, decaglyceryl diisostearate, decaglyceryl monomyriate, decaglyceryl monolaurate, hexaglyceryl monooleate, and combinations thereof.

[0070] The rinse-off personal cleansing composition may be applied by various means, including by rubbing, scraping, or tapping with hands or fingers, or by an implement and / or delivery-enhancing device. Non-limiting examples of implements include sponges or sponge-tipped applicators, mesh shower puffs, swabs, brushes, wipes (e.g., washcloths), loofahs, and combinations thereof. Non-limiting examples of delivery-enhancing devices include mechanical, electrical, ultrasonic, and / or other energy devices. The use of an implement or device can aid in the delivery of particulate antimicrobial agents to target areas, such as hair follicles and undulations that may be present in the underarms. The rinse-off cleansing product may be sold together with such an implement or device. Alternatively, the implement or device may be sold separately but include labeling indicating that it is to be used with the rinse-off cleansing product. The implement and delivery device may use interchangeable parts (e.g., skin-interacting parts), which may be sold separately or in a kit with the rinse-off cleansing product.

[0071] B. Solid Personal Cleansing Compositions As described herein, personal cleansing compositions can take many forms. One suitable form is that of a solid personal cleansing composition. Solid compositions can take many forms, such as powders, pellets, bars, and the like. While these forms are generally described herein as soap bars, it should be understood that the solid compositions can take other forms or shapes. An example of a bar soap personal cleansing composition can comprise about 0.1% to about 35% water by weight of the personal cleansing composition, about 45% to about 99% soap by weight of the personal cleansing composition, and about 0.01% to about 5% particulate antibacterial agent by weight of the personal cleansing composition. Another suitable antibacterial bar soap can comprise, for example, about 0.1% to about 30% water by weight of the personal cleansing composition, about 40% to about 99% soap by weight of the personal cleansing composition, and about 0.25% to about 3% particulate antibacterial agent by weight of the personal cleansing composition.

[0072] The bar soap composition may be referred to as a conventional solid (i.e., non-flowable) bar soap composition. Some bar soap compositions contain conventional soap, while others contain synthetic surfactants, and still others contain a mixture of soap and synthetic surfactants. The bar composition may contain, for example, from about 0% to about 45% synthetic anionic surfactant. Examples of suitable conventional soaps may include unassembled (i.e., containing about 5% or less water-soluble surfactant builder), milled toilet bars.

[0073] Personal cleansing bar compositions may contain, for example, from about 45% to about 99% or from about 50% to about 75% soap by weight of the personal cleansing composition. Such soaps may include typical soaps, i.e., alkali metal or alkanolammonium salts of alkane or alkene monocarboxylic acids. Sodium, magnesium, potassium, calcium, mono-, di-, and triethanolammonium cations, or combinations thereof, may be suitable for personal cleansing compositions. The soap included in the personal cleansing composition may include sodium soap, or a combination of sodium soap and from about 1% to about 25% ammonium, potassium, magnesium, calcium, or a mixture of these soaps. Furthermore, the soap may be any of the well-known alkali metal salts of alkane or alkenoic acids having from about 12 to about 22 carbon atoms or from about 12 to about 18 carbon atoms. Another suitable soap may be an alkali metal carboxylate salt of an alkyl or alkene hydrocarbon having from about 12 to about 22 carbon atoms. Additional suitable soap compositions are described in U.S. Patent Application Publication Nos. 2012 / 0219610 and 2008 / 0020959.

[0074] The personal cleansing composition may also include soaps with fatty acids. For example, one bar soap composition may contain from about 40% to about 95% C8-C9 soluble alkali metal soaps. 24 or C 10 ~C 20 Fatty acids may be used. The fatty acids may have, for example, the fatty acid distribution of coconut oil, which may provide the lower end of a broad molecular weight range, or the fatty acid distribution of peanut oil or rapeseed oil or their hydrogenated derivatives, which may provide the upper end of a broad molecular weight range. Other such compositions may include the fatty acid distribution of tallow and / or vegetable oil. Tallow is typically 2.5% C 14 , 29%C 16 , 23%C 18tallow may contain a fatty acid mixture that may have an approximate carbon chain length distribution of 2% palmitoleic acid, 41.5% oleic acid, and 3% linoleic acid. Tallow may also contain other mixtures with similar distributions, such as fatty acids derived from various animal tallows and / or lard. In one example, tallow may also be hardened (i.e., hydrogenated) so that some or all of the unsaturated fatty acid moieties may be converted to saturated fatty acid moieties.

[0075] Suitable examples of vegetable oils include palm oil, coconut oil, palm kernel oil, palm stearin, soybean oil, and hydrogenated rice bran oil, or mixtures thereof, as such oils may be more readily available fats. One example of a suitable coconut oil may contain about 85% of fatty acids having at least 12 carbon atoms. Such a ratio may be used in conjunction with mixtures of coconut oil and fats, such as tallow, palm oil, or non-tropical nut oils or fats, where the main chain length is C. 16 The soap included in the personal cleansing composition can be, for example, a sodium soap having a mixture of about 67-68% tallow, about 16-17% coconut oil, about 2% glycerin, and about 14% water.

[0076] The soaps included in the personal cleansing compositions may also be unsaturated according to commercially acceptable standards, for example, the soaps included in the personal cleansing compositions may contain unsaturation in the range of about 37% to about 45% of the saponifiable material.

[0077] Soaps included in personal cleansing compositions can be made, for example, by the classical kettle boiling process or by modern continuous soap making processes, and natural fats and oils, such as tallow or coconut oil or their equivalents, can be saponified with alkali metal hydroxides using procedures well known to those skilled in the art. Soaps can also be made from lauric acid (C 12 ), myristic acid (C 14 ), palmitic acid (C 16 ), or stearic acid (C 18 ), with alkali metal hydroxides or carbonates.

[0078] The soap contained in the personal cleansing composition can also be made by a continuous soap manufacturing process. The soap can be processed into soap noodles through a vacuum flash drying process. One example of a suitable soap noodle contains about 67.2% tallow soap, about 16.8% coconut soap, about 2% glycerin, and about 14% water by weight of the soap noodle. The soap noodle can then be used in a milling process to complete the personal cleansing composition.

[0079] 2. Detergent compositions for fabric and household applications The surfactants or surfactant intermediates described herein can be used to formulate detergent compositions for fabric and home care applications, particularly for laundry and hard surface cleaning.Examples of laundry detergents include granular detergents and liquid laundry detergents, including low-water liquid detergent compositions that are encapsulated in a water-soluble film to form a soluble unit-dose article.Examples of hard surface cleaning detergent compositions include those suitable for cleaning floors, countertops, dishes, etc., and the surfactants and intermediates are particularly suitable for hand-washing dishwashing detergent compositions.

[0080] Suitable laundry detergent compositions may contain non-soap surfactants, including anionic non-soap surfactants and nonionic surfactants. The laundry detergent composition may contain 10% to 60% or 20% to 55% by weight of the laundry detergent composition. The ratio of non-soap anionic surfactant to nonionic surfactant is 1:1 to 20:1, 1.5:1 to 17.5:1, 2:1 to 15:1, or 2.5:1 to 13:1. Suitable non-soap anionic surfactants include linear alkylbenzene sulfonates, alkyl sulfates, or mixtures thereof. The weight ratio of linear alkylbenzene sulfonate to alkyl sulfate may be 1:2 to 9:1, 1:1 to 7:1, 1:1 to 5:1, or 1:1 to 4:1. Suitable linear alkylbenzene sulfonates include C 10 ~C 16 Alkylbenzene sulfonic acid, or C 11~C 14 The alkyl benzene sulfonic acid. Suitable alkyl sulfate anionic surfactants include alkoxylated alkyl sulfates, non-alkoxylated alkyl sulfates, and mixtures thereof. Preferably, the linear alkyl benzene sulfonate surfactant is greater than 50%, preferably greater than 60%, preferably greater than 70% C12, more preferably greater than 75% C12. 12 Materials include: Suitable alkoxylated alkyl sulfate anionic surfactants include ethoxylated alkyl sulfate anionic surfactants that can be derived according to the process of the present invention or from surfactant intermediates according to the present invention. Suitable alkyl sulfate anionic surfactants include ethoxylated alkyl sulfate anionic surfactants having a molar average degree of ethoxylation of 1 to 5, 1 to 3, or 2 to 3. The alkyl alkoxylated sulfates can have a broad or peaked alkoxy distribution. The alkyl moieties of the AES can contain, on average, 13.7 to about 16, or 13.9 to 14.6 carbon atoms. At least about 50% or at least about 60% of the AES molecules can contain alkyl moieties having 14 or more carbon atoms, preferably 14 to 18, or 14 to 17, or 14 to 16, or 14 to 15 carbon atoms. The alkyl sulfate anionic surfactants may include non-ethoxylated alkyl sulfates and ethoxylated alkyl sulfates, and the molar average degree of ethoxylation of the alkyl sulfate anionic surfactants is 1 to 5, 1 to 3, or 2 to 3. The alkyl fraction of the alkyl sulfate anionic surfactants may be derived from fatty alcohols, oxo-synthetic alcohols, Guerbet alcohols, or mixtures thereof. Preferred alkyl sulfates include, optionally, 2-alkyl branched primary alcohol sulfates, particularly 2-branched C 12~15 Primary alcohol sulfates, linear primary alcohol sulfates, especially linear C 12~14Included are primary alcohol sulfates and ethoxylated alcohol sulfates, including mixtures thereof. The laundry detergent composition may comprise from 10% to 50%, or from 15% to 45%, or from 20% to 40%, or from 30% to 40% of the non-soap anionic surfactant, by weight of the laundry detergent composition.

[0081] Suitable nonionic surfactants may be selected from broad or narrow range alkoxylated alcohols, oxo-synthetic alcohol alkoxylates, Guerbet alcohol alkoxylates, alkylphenol alcohol alkoxylates, or mixtures thereof. The laundry detergent composition may comprise from 0.01% to 10%, 0.01% to 8%, 0.1% to 6%, or 0.15% to 5% of nonionic surfactant by weight of the liquid laundry detergent composition.

[0082] The laundry detergent composition comprises from 1.5% to 20%, or from 2% to 15%, or from 3% to 10%, or from 4% to 8%, by weight of the laundry detergent composition, of a soap, such as a fatty acid salt. Such soaps may be amine-neutralized, for example, using an alkanolamine, such as monoethanolamine.

[0083] The laundry detergent composition may comprise adjunct ingredients selected from the group comprising builders including citrates, enzymes, bleaches, bleach catalysts, dyes, hueing dyes, leuco dyes, brighteners, cleaning polymers including alkoxylated polyamines and polyethyleneimines, amphiphilic copolymers, soil release polymers, surfactants, solvents, dye transfer inhibitors, chelating agents, diamines, perfumes, encapsulated perfumes, polycarboxylates, structuring agents, pH adjusters, antioxidants, antibacterial agents, antimicrobial agents, preservatives, and mixtures thereof.

[0084] The laundry detergent composition may have a pH of from 2 to 10, or from 6.5 to 8.9, or from 7 to 8, the pH of the laundry detergent composition being measured at a 10% product concentration in demineralized water at 20°C.

[0085] Liquid laundry detergent compositions may be Newtonian or non-Newtonian, preferably non-Newtonian.

[0086] In liquid laundry detergent compositions, the composition may comprise from 5% to 99%, or from 15% to 90%, or from 25% to 80% water by weight of the liquid detergent composition.

[0087] The liquid laundry detergent composition can also be a low-water liquid detergent composition, comprising less than 15% or less than 12% water by weight of the liquid laundry detergent composition. Such laundry detergent compositions can comprise 10% and 40%, or 15% to 30%, by weight of the liquid laundry detergent composition, of a non-aqueous solvent selected from 1,2-propanediol, dipropylene glycol, tripropylene glycol, glycerol, sorbitol, polyethylene glycol, or mixtures thereof. Such liquid detergent compositions are particularly suitable for encapsulation in a water-soluble film to form a water-soluble unit-dose laundry detergent article.

[0088] At least one water-soluble film can be oriented to create at least one unit-dose inner compartment, with the at least one unit-dose inner compartment containing the detergent composition. The water-soluble film can include a polyvinyl alcohol polymer or copolymer, such as a blend of polyvinyl alcohol polymers and / or polyvinyl alcohol copolymers. The polyvinyl alcohol polymer and / or polyvinyl alcohol copolymer can be selected from sulfonated and carboxylated anionic polyvinyl alcohol copolymers, particularly carboxylated anionic polyvinyl alcohol copolymers, such as blends of polyvinyl alcohol homopolymers and carboxylated anionic polyvinyl alcohol copolymers. The water-soluble film can be supplied by Monosol under product reference numbers M8630, M8900, M8779, and M8310.

[0089] Suitable liquid hand dishwashing detergent compositions are typically aqueous and comprise from 50% to 90%, preferably from 60% to 75%, water by weight of the total composition.

[0090] Hand dishwashing compositions may comprise from 5% to 50%, preferably from 8% to 45%, more preferably from 15% to 40% by weight of the total composition of a surfactant system.

[0091] Such surfactant systems may comprise 60% to 90% by weight, more preferably 70% to 80% by weight, of the anionic surfactant. The alkyl sulfated anionic surfactant is preferably selected from the group consisting of alkyl sulfates, alkyl alkoxy sulfates, preferably alkyl ethoxy sulfates, and mixtures thereof. The alkyl sulfated anionic surfactant preferably has an average alkyl chain length of 8 to 18, preferably 10 to 14, more preferably 12 to 14, and most preferably 12 to 13 carbon atoms. The alkyl sulfated anionic surfactant preferably has an average degree of alkoxylation, preferably an ethoxylation degree, of less than 5, preferably less than 3, more preferably 0.5 to 2.0, and most preferably 0.5 to 0.9. The ethoxylated alkyl sulfate surfactant may be derived according to the process of the present invention / from a surfactant intermediate according to the present invention. The alkyl sulfate anionic surfactant preferably has a weight average degree of branching of more than 10%, preferably more than 20%, more preferably more than 30%, even more preferably 30% to 60%, and most preferably 30% to 50%. Suitable counterions include alkali metal cations, alkaline earth metal cations, alkanolammonium, or ammonium or substituted ammonium, preferably sodium. Suitable examples of commercially available alkyl sulfate anionic surfactants include those derived from alcohols sold by Shell under the brand name Neodol® or by Sasol under the brand names Lial®, Isalchem®, and Safol®, or some of the natural alcohols produced by Procter & Gamble Chemicals.

[0092] The surfactant system may comprise 0.1% to 20%, more preferably 0.5% to 15%, and especially 2% to 10% by weight of the liquid hand dishwashing detergent composition of a co-surfactant. Preferred co-surfactants are selected from the group consisting of amphoteric surfactants, zwitterionic surfactants, and mixtures thereof. The weight ratio of anionic surfactant to co-surfactant may be 1:1 to 8:1, preferably 2:1 to 5:1, more preferably 2.5:1 to 4:1. The co-surfactant is preferably an amphoteric surfactant, more preferably an amine oxide surfactant. Preferably, the amine oxide surfactant is selected from the group consisting of alkyl dimethyl amine oxides, alkylamidopropyl dimethyl amine oxides, and mixtures thereof, most preferably C12-C14 alkyl dimethyl amine oxides. Suitable zwitterionic surfactants include betaine surfactants, preferably cocamidopropyl betaine.

[0093] Preferably, the surfactant system of the present compositions further comprises from 1% to 25%, preferably from 1.25% to 20%, more preferably from 1.5% to 15%, and most preferably from 1.5% to 5% by weight of the surfactant system of a nonionic surfactant. Suitable nonionic surfactants may be selected from the group consisting of alkoxylated nonionic surfactants, alkyl polyglucoside (APG) surfactants, and mixtures thereof. Suitable alkoxylated nonionic surfactants are linear or branched, primary or secondary alkyl alkoxylated, preferably alkyl ethoxylated, nonionic surfactants containing an average of 9 to 15, preferably 10 to 14, carbon atoms in the alkyl chain and an average of 5 to 12, preferably 6 to 10, and most preferably 7 to 8, ethylene oxide units per mole of alcohol. Most preferably, the alkyl polyglycoside surfactants have an average alkyl carbon chain length of 10 to 16, preferably 10 to 14, most preferably 12 to 14, and an average degree of polymerization of 0.5 to 2.5, preferably 1 to 2, most preferably 1.2 to 1.6. C8 to C16 alkyl polyglycosides are commercially available from several sources (e.g., Simusol® surfactants from Seppic Corporation; and Glucopon® 600 CSUP, Glucopon® 650 EC, Glucopon® 600 CSUP / MB, and Glucopon® 650 EC / MB from BASF Corporation).

[0094] The liquid hand dishwashing detergent compositions herein optionally contain builders (e.g., preferably citrate), chelating agents (e.g., preferably GLDA), conditioning polymers, cleaning polymers comprising polyalkoxylated polyalkyleneimines, surface modifying polymers, soil flocculating polymers, foaming polymers comprising EO-PO-EO triblock copolymers, grease cleaning polymers comprising cyclic polyamines, structurants, emollients, humectants, skin rejuvenation actives, enzymes, carboxylic acids, scrubbing particles, bleaches and bleach activators, fragrances, malodor control agents, Many other auxiliary ingredients may be included, such as pigments, dyes, opacifiers, beads, pearlescent particles, microcapsules, organic solvents, inorganic cations such as alkaline earth metals such as Ca / Mg ions, antimicrobial agents, preservatives, viscosity modifiers (e.g., salts such as NaCl and other mono-, di-, and trivalent salts), and pH adjusters and buffering means (e.g., carboxylic acids such as citric acid, HCl, NaOH, KOH, alkanolamines, phosphoric and sulfonic acids, carbonates such as sodium carbonate, bicarbonates, sesquicarbonates, borates, silicates, phosphates, imidazoles, etc.).

[0095] The pH of the hand dishwashing detergent composition, measured at 10% product concentration in demineralized water at 20°C, can be adjusted to 3 to 14, more preferably 4 to 13, more preferably 6 to 12, and most preferably 8 to 10. The hand dishwashing composition can be Newtonian or non-Newtonian, preferably non-Newtonian. The composition can have a viscosity of 10 mPa·s to 10,000 mPa·s, preferably 100 mPa·s to 5,000 mPa·s, more preferably 300 mPa·s to 2,000 mPa·s, or most preferably 500 mPa·s to 1,500 mPa·s. Viscosity is measured at 20°C using a Brookfield RT viscometer with spindle 31 adjusted so that the viscometer RPM achieves 40% to 60% torque. [Example]

[0096] 1. Extraction of glycol by-products from alcohol ethoxylates A drum (approximately 171 kg) of alcohol ethoxylate is added to a vessel containing 115 kg of water. The vessel is agitated for 30 minutes at a temperature of 70-80°C, after which the agitation is stopped, and the aqueous and organic layers are allowed to gravity separate for 1-4 hours before the bottom aqueous layer is drained. This process can be repeated, for example, three times, each time with 115 kg of water, to thoroughly water-wash the alcohol ethoxylate. At the end of the water wash, the alcohol ethoxylate is dried to aid in the removal of the added water, maintaining a bulk temperature of 70-90°C and slowly reducing the vacuum to approximately 15 mmHg to avoid foaming. At the end of the vacuum drying, a nitrogen sparge through the alcohol ethoxylate can be added to further draw off the water to <0.1 wt%, with a target of 0.05 wt% or less. The final yield of washed and dried alcohol ethoxylate is, for example, 97.5% of the starting alcohol ethoxylate weight.

[0097] 2. Extraction of polyethylene glycol from tridecyl alcohol ethoxylate-2 (TDA-2) Add 600g of TDA-2 to a 1L open-head glass reactor equipped with a bottom drain valve. Heat the contents to 50°C while mixing. Add 300mL of water to the TDA-2. Adding water at this temperature can cause the contents of the reactor to gel. If this occurs, increase the temperature. Now heat to 70°C to keep everything fluid. Allow the mixture to mix for 30 minutes. Then, stop mixing and allow the contents to separate into layers. Once two layers are present, drain the bottom layer. The bottom layer is the aqueous layer and contains the polyethylene glycol solubilized in water. Wash the top layer again by adding an additional 300mL of water and repeating the process. This can be repeated as needed. This will result in a total of three washes.

[0098] Once washing is complete, the TDA-2 is dried to remove excess water. This is accomplished by vacuum drying. The vacuum is slowly and incrementally reduced until the desired vacuum level of approximately 17 mmHg is reached to avoid excessive foaming. The vacuum is maintained until the TDA-2 becomes clear and no observable moisture is collected. If the final product has more moisture than desired, the time under vacuum drying can be increased. Additionally, a nitrogen sparge line can be used in addition to the vacuum to remove residual moisture.

[0099] 3. Exemplary Personal Cleansing Compositions [Table 7]

[0100] Personal cleansing compositions A-D of the present invention can be prepared by first premixing the acrylates / C10-30 alkyl acrylate crosspolymer, xanthan gum, and trideceth-3 (trideceth-3 / polymer premix). Water is added to a container, followed by the guar hydroxypropyltrimonium chloride and sodium chloride while mixing. Reduced glycol sulfate trideceth-2 sodium sulfate, cocamidopropyl betaine, and trideceth-3 / polymer premix are then added. Citric acid is then added to adjust the pH to 5.7. Preservatives and fragrance are then added. Mixing is continued until homogeneous. The benefit agent is then added to the surfactant phase using a SpeedMixer and mixed at 2,000 rpm for 1 minute.

[0101] [Table 8]

[0102] Personal cleansing compositions E and F of the present invention can be formed by the following process: DI water is added to a mixing container; Reduced glycol sulfate / scrubbed reduced glycol sulfate sodium laureth-3 sulfate, sodium lauryl sulfate, and cocamidopropyl betaine are added to the mixing container, followed by stirring the contents of the container; Fragrance is then added to the mixture and mixed for at least 10 minutes; Sodium benzoate is then added and allowed to dissolve in the mixture for at least 2 minutes; Citric acid is used to titrate the mixture until a pH of about 6.5 to about 7.5 is reached, followed by the addition of a preservative, followed by the addition of an antibacterial active; The mixture is mixed until homogeneous; Sodium chloride is then added and allowed to dissolve in the mixture for at least 2 minutes; DI water and / or sodium chloride are then added to adjust the viscosity of the mixture to a target range of 4,500 to 7,500 cP.

[0103] 4. Laundry Formulations of the Present Invention The following are exemplary liquid laundry detergent formulations: Ethoxylated alkyl sulfate surfactants may be derived according to the process of the present invention / from surfactant intermediates according to the present invention.

[0104] [Table 9] 1. C12-15 EO2.5S alkyl ethoxy sulfate, the alkyl portion of which contains about 13.9 to about 14.6 carbon atoms. 2 PE-20 commercially available from BASF 3 The nuclease enzyme is as claimed in co-pending European Patent Application No. 19219568.3 4. Antioxidant 1 is 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid, methyl ester [6386-38-5] 5 Antioxidant 2 is Tinogard TS, commercially available from BASF 6 The sanitizing agent is Tinosan HP 100, commercially available from BASF. 7 Defoamer blend supplied by Dow Corning, 80-92% ethylmethyl, methyl(2-phenylpropyl)siloxane, 5-14% MQ resin in octyl stearate, 3-7% modified silica. 8 The optical brightener is 4,4'-bis{[4-anilino-6-morpholino-s-triazin-2-yl]-amino}-2,2'-stilbenedisulfonate or 2,2'-([1,1'-biphenyl]-4,4'-diyldi-2,1-ethenediyl)bis-benzenesulfonic acid disodium salt.

[0105] 5. Water-soluble unit dose formulations of the present invention The following are exemplary water-soluble unit dose formulations. The ethoxylated alkyl sulfate surfactants may be derived from surfactant intermediates according to the process / according to the present invention. The composition may be part of a single-chamber water-soluble unit dose article or may be divided across multiple compartments to yield the following "overall compartment averaged" total article composition:

[0106] [Table 10]

[0107] 6. Liquid hand dishwashing detergent of the present invention The following is an exemplary liquid hand dishwashing detergent formulation. The formulation can be made by standard mixing of the individual components. The ethoxylated alkyl sulfate surfactant can be derived according to the process of the present invention / from a surfactant intermediate according to the present invention.

[0108] [Table 11]

[0109] combination A. A method for producing a reduced glycol fatty alcohol ethoxylate material, the method comprising removing at least a portion of the glycol in the fatty alcohol ethoxylate material after formation of the fatty alcohol ethoxylate material.

[0110] B. The method of paragraph A, wherein the glycol comprises an ethylene glycol oligomer.

[0111] C. Ethylene glycol oligomer is HO(CH2CH2O) n H, wherein n is from 2 to about 30, preferably from 2 to about 25, more preferably from 2 to about 15, even more preferably from 2 to about 10, and most preferably from 2 to about 5.

[0112] D. The method of any of paragraphs A-C, wherein at least a portion of the glycol is removed by extracting the glycol from the fatty alcohol ethoxylate material.

[0113] E. The method of paragraph D, wherein at least a portion of the glycol is extracted with water.

[0114] F. The method of paragraph D or E, wherein the glycol is extracted at a temperature above the gel point of the fatty alcohol ethoxylate water mixture.

[0115] G. The method according to paragraph F, wherein the extraction temperature is from about 65°C to about 90°C, preferably from about 67°C to about 88°C, or more preferably from about 70°C to about 85°C.

[0116] H. The method of paragraph F, wherein the glycol is extracted at a temperature of about 70°C.

[0117] I. The method of any of paragraphs D-H, wherein at least a portion of the glycol is extracted with a combination of water and sodium chloride.

[0118] J. The method of any of paragraphs D-I, wherein the reduced glycol fatty alcohol material is concentrated by drying at least a portion of the water.

[0119] K. The method of any of paragraphs A-J, wherein the amount of glycol in the reduced glycol fatty alcohol material is from about 0 ppm to about 100 ppm, preferably from about 0 ppm to about 90 ppm, more preferably from about 0 ppm to about 80 ppm, even more preferably from about 0 ppm to about 70 ppm, even more preferably from about 0 ppm to about 60 ppm, even more preferably from about 0 ppm to about 50 ppm, even more preferably from about 0 ppm to about 40 ppm, even more preferably from about 0 ppm to about 30 ppm, even more preferably from about 0 ppm to about 20 ppm, and most preferably from about 0 ppm to about 10 ppm.

[0120] L. The method of any of paragraphs A-K, wherein the amount of glycol in the reduced glycol fatty alcohol material is at least 10% by weight less, preferably about 10% by weight to about 100% by weight less, about 15% by weight to about 95% by weight less, about 15% by weight to about 90% by weight less, about 15% by weight to about 85% by weight less, about 20% by weight to about 95% by weight less, about 20% by weight to about 90% by weight less, about 20% by weight to about 85% by weight less, about 25% by weight to about 95% by weight less, about 25% by weight to about 90% by weight less, about 25% by weight to about 85% by weight less, about 25% by weight to about 75% by weight, about 30% by weight to about 95% by weight, about 30% by weight to about 90% by weight, about 30% by weight to about 85% by weight, and / or about 30% by weight to about 75% by weight less.

[0121] M. The method of any of paragraphs A-L, wherein the fatty alcohol ethoxylate material comprises laureth-1, laureth-2, laureth-3, trideceth-1, trideceth-2, trideceth-2.5, trideceth-3, or a combination thereof.

[0122] N. A method for producing a fatty alcohol ethoxylate material, the method comprising scrubbing a reduced glycol fatty alcohol material described in any of paragraphs A-M to remove at least a portion of the 1,4-dioxane.

[0123] O. A method for reducing the amount of ethylene glycol oligomers in an alcohol ethoxylate material, comprising extracting the ethylene glycol oligomers from the alcohol ethoxylate material.

[0124] P. The method of paragraph O, wherein the glycol comprises an ethylene glycol oligomer.

[0125] Q. Ethylene glycol oligomer is HO(CH2CH2O) n H, wherein n is from 2 to about 30, preferably from 2 to about 25, more preferably from 2 to about 15, even more preferably from 2 to about 10, and most preferably from 2 to about 5.

[0126] R. The method of any of paragraphs O-Q, wherein at least a portion of the glycol is removed by extracting the glycol from the fatty alcohol ethoxylate material.

[0127] S. The method of paragraph R, wherein at least a portion of the glycol is extracted with water.

[0128] T. The method of paragraph R or S, wherein the glycol is extracted at a temperature above the gel point of the fatty alcohol ethoxylate water mixture.

[0129] U. The method according to paragraph S, wherein the extraction temperature is from about 65°C to about 90°C, preferably from about 67°C to about 88°C, or more preferably from about 70°C to about 85°C.

[0130] V. The method of paragraph S, wherein the glycol is extracted at a temperature of about 70°C.

[0131] W. The method of any of paragraphs RV, wherein at least a portion of the glycol is extracted with a combination of water and sodium chloride.

[0132] X. The method of any of paragraphs R through W, wherein the reduced glycol fatty alcohol material is concentrated by drying at least a portion of the water.

[0133] Y. The method of any of paragraphs O through X, wherein the amount of glycol in the reduced glycol fatty alcohol material is from about 0 ppm to about 100 ppm, preferably from about 0 ppm to about 90 ppm, more preferably from about 0 ppm to about 80 ppm, even more preferably from about 0 ppm to about 70 ppm, even more preferably from about 0 ppm to about 60 ppm, even more preferably from about 0 ppm to about 50 ppm, even more preferably from about 0 ppm to about 40 ppm, even more preferably from about 0 ppm to about 30 ppm, even more preferably from about 0 ppm to about 20 ppm, and most preferably from about 0 ppm to about 10 ppm.

[0134] Z. The method of any of paragraphs O through Y, wherein the amount of glycol in the reduced glycol fatty alcohol material is at least 10% less by weight, preferably about 10% to about 100% less, about 15% to about 95% by weight, about 15% to about 90% by weight, about 15% to about 85% by weight, about 20% to about 95% by weight, about 20% to about 90% by weight, about 20% to about 85% by weight, about 25% to about 95% by weight, about 25% to about 90% by weight, about 25% to about 85% by weight, about 25% to about 75% by weight, about 30% to about 95% by weight, about 30% to about 90% by weight, about 30% to about 85% by weight, and / or about 30% to about 75% by weight less than that in the fatty alcohol material prior to removal of at least a portion of the glycol.

[0135] AA. The method of any of paragraphs O-Z, wherein the fatty alcohol ethoxylate material comprises laureth-1, laureth-2, laureth-3, trideceth-1, trideceth-2, trideceth-2.5, trideceth-3, or a combination thereof.

[0136] A2. A method for producing a reduced glycol sulfate ethoxylated sulfate surfactant, the method comprising removing at least a portion of the glycols in the ethoxylated fatty alcohol feedstock prior to sulfating the ethoxylated fatty alcohol feedstock to produce a reduced glycol sulfate ethoxylated sulfate surfactant.

[0137] B2. The method of paragraph A2, wherein the glycol comprises an ethylene glycol oligomer.

[0138] C2. Ethylene glycol oligomer is HO(CH2CH2O) n H, wherein n is from 2 to about 30, preferably from 2 to about 25, more preferably from 2 to about 15, even more preferably from 2 to about 10, and most preferably from 2 to about 5.

[0139] D2. The method of any of paragraphs A2-C2, wherein at least a portion of the glycol is removed by extracting the glycol from the ethoxylated fatty alcohol feedstock.

[0140] E2. The method of paragraph D2, wherein at least a portion of the glycol is extracted with water.

[0141] F2. The method of paragraphs D2 or E2, wherein the glycol is extracted at a temperature above the gel point of the fatty alcohol ethoxylate water mixture.

[0142] G2. The method according to paragraph F2, wherein the extraction temperature is from about 65°C to about 90°C, preferably from about 67°C to about 88°C, or more preferably from about 70°C to about 85°C.

[0143] H2. The method of paragraph F2, wherein the glycol is extracted at a temperature of about 70°C.

[0144] I2. The method of any of paragraphs D2-H2, wherein at least a portion of the glycol is extracted with a combination of water and sodium chloride.

[0145] J2. The method of any of paragraphs D2-I2, wherein after extraction, the ethoxylated fatty alcohol feedstock is concentrated by drying at least a portion of the water.

[0146] K2. The method of any of paragraphs A2-J2, wherein the amount of glycol in the ethoxylated fatty alcohol feedstock after removal of at least a portion of the glycol is from about 0 ppm to about 100 ppm, preferably from about 0 ppm to about 90 ppm, more preferably from about 0 ppm to about 80 ppm, even more preferably from about 0 ppm to about 70 ppm, even more preferably from about 0 ppm to about 60 ppm, even more preferably from about 0 ppm to about 50 ppm, even more preferably from about 0 ppm to about 40 ppm, even more preferably from about 0 ppm to about 30 ppm, even more preferably from about 0 ppm to about 20 ppm, and most preferably from about 0 ppm to about 10 ppm.

[0147] L2. The amount of glycol in the ethoxylated fatty alcohol feedstock after removal of at least a portion of the glycol is at least 10% by weight less, preferably about 10% by weight to about 100% by weight less, about 15% by weight to about 95% by weight less, about 15% by weight to about 90% by weight less, about 15% by weight to about 85% by weight less, about 20% by weight to about 30% by weight less, or about 30% by weight to about 40% by weight less than that in the ethoxylated fatty alcohol feedstock before removal of at least a portion of the glycol. % to about 95% by weight less, about 20% to about 90% by weight less, about 20% to about 85% by weight less, about 25% to about 95% by weight less, about 25% to about 90% by weight less, about 25% to about 85% by weight less, about 25% to about 75% by weight, about 30% to about 95% by weight, about 30% to about 90% by weight, about 30% to about 85% by weight, and / or about 30% to about 75% by weight less.

[0148] M2. The method of any of paragraphs A2-L2, wherein the reduced glycol sulfate ethoxylated sulfate surfactant comprises sodium laureth-1 sulfate, sodium laureth-2 sulfate, sodium laureth-3 sulfate, sodium trideceth-1 sulfate, sodium trideceth-2 sulfate, sodium trideceth-2.5 sulfate, sodium trideceth-3 sulfate, or a combination thereof.

[0149] N2. The method of any of paragraphs A2 through M2, wherein the amount by weight of glycol sulfate in the reduced glycol sulfate ethoxylated surfactant is 100 ppm by weight or less.

[0150] O2. The method of any of paragraphs A2-N2, wherein the reduced glycol sulfate ethoxylated sulfate surfactant has 100 ppm by weight or less of diethylene glycol monosulfate.

[0151] P2. The method of any of paragraphs A2-O2, wherein the amount of glycol sulfate in the reduced glycol ethoxylated sulfate surfactant is from about 0 ppm to about 100 ppm, from about 0 ppm to about 90 ppm, from about 0 ppm to about 80 ppm, from about 0 ppm to about 70 ppm, from about 0 ppm to about 60 ppm, from about 0 ppm to about 50 ppm, from about 0 ppm to about 40 ppm, from about 0 ppm to about 30 ppm, from about 0 ppm to about 20 ppm, or from about 0 ppm to about 10 ppm.

[0152] Q2. The method of any of paragraphs A2-P2, wherein the sulfation reaction is carried out to less than 100% completion.

[0153] R2. The method of paragraph Q2, wherein the sulfation reaction is carried out to 97%, 94%, or 90% completion.

[0154] S2. Use of a reduced glycol ethoxylated material to produce a reduced glycol sulfate ethoxylated sulfate surfactant.

[0155] T2. A method for producing an ethoxylated sulfate surfactant, comprising scrubbing the reduced glycol sulfate ethoxylated sulfate surfactant described in any of paragraphs A-R to remove at least a portion of the 1,4-dioxane.

[0156] U2. A method for producing a reduced glycol sulfate ethoxylated surfactant, the method comprising sulfateing a reduced glycol fatty alcohol to produce a reduced glycol sulfate ethoxylated sulfate surfactant.

[0157] V2. The method of paragraph U2, wherein the glycol comprises an ethylene glycol oligomer.

[0158] W2. Ethylene glycol oligomer is HO(CH2CH2O) n H, wherein n is from 2 to about 30, preferably from 2 to about 25, more preferably from 2 to about 15, even more preferably from 2 to about 10, and most preferably from 2 to about 5.

[0159] X2. The method of any of paragraphs U2-W2, wherein at least a portion of the glycol is removed by extracting the glycol from the ethoxylated fatty alcohol feedstock.

[0160] Y2. The method of paragraph X2, wherein at least a portion of the glycol is extracted with water.

[0161] Z2. The method of paragraph X2 or Y2, wherein the glycol is extracted at a temperature above the gel point of the fatty alcohol ethoxylate water mixture.

[0162] AA2. The method according to paragraph Z2, wherein the extraction temperature is about 65°C to about 90°C, preferably about 67°C to about 88°C, or more preferably about 70°C to about 85°C.

[0163] BB2. The method of paragraph Z2, wherein the glycol is extracted at a temperature of about 70°C.

[0164] CC2. The method of any of paragraphs X2-BB2, wherein at least a portion of the glycol is extracted with a combination of water and sodium chloride.

[0165] DD2. The method of any of paragraphs X2-CC2, wherein after extraction, the ethoxylated fatty alcohol feedstock is concentrated by drying at least a portion of the water.

[0166] EE2. The method of any of paragraphs U2 through DD2, wherein the amount of glycol in the reduced glycol fatty alcohol is from about 0 ppm to about 100 ppm, preferably from about 0 ppm to about 90 ppm, more preferably from about 0 ppm to about 80 ppm, even more preferably from about 0 ppm to about 70 ppm, even more preferably from about 0 ppm to about 60 ppm, even more preferably from about 0 ppm to about 50 ppm, even more preferably from about 0 ppm to about 40 ppm, even more preferably from about 0 ppm to about 30 ppm, even more preferably from about 0 ppm to about 20 ppm, and most preferably from about 0 ppm to about 10 ppm.

[0167] FF2. The method of any of paragraphs U2-EE2, wherein the amount of glycol in the reduced glycol fatty alcohol is at least 10% by weight less, preferably about 10% by weight to about 100% by weight less, about 15% by weight to about 95% by weight less, about 15% by weight to about 90% by weight less, about 15% by weight to about 85% by weight less, about 20% by weight to about 95% by weight less, about 20% by weight to about 90% by weight less, about 20% by weight to about 85% by weight less, about 25% by weight to about 95% by weight less, about 25% by weight to about 90% by weight less, about 25% by weight to about 85% by weight less, about 25% by weight to about 75% by weight, about 30% by weight to about 95% by weight, about 30% by weight to about 90% by weight, about 30% by weight to about 85% by weight, and / or about 30% by weight to about 75% by weight less.

[0168] GG2. The method of any of paragraphs U2-FF2, wherein the reduced glycol sulfate ethoxylated sulfate surfactant comprises sodium laureth-1 sulfate, sodium laureth-2 sulfate, sodium laureth-3 sulfate, sodium trideceth-1 sulfate, sodium trideceth-2 sulfate, sodium trideceth-2.5 sulfate, sodium trideceth-3 sulfate, or a combination thereof.

[0169] HH2. The method of any of paragraphs U-GG2, wherein the amount by weight of glycol sulfate in the reduced glycol sulfate ethoxylated surfactant is 100 ppm by weight or less.

[0170] II2. The method of any of paragraphs U2-HH2, wherein the reduced glycol sulfate ethoxylated sulfate surfactant has 100 ppm by weight or less of diethylene glycol monosulfate.

[0171] JJ2. The method of any of paragraphs U2-II2, wherein the amount of glycol sulfate in the reduced glycol ethoxylated sulfate surfactant is from about 0 ppm to about 100 ppm, from about 0 ppm to about 90 ppm, from about 0 ppm to about 80 ppm, from about 0 ppm to about 70 ppm, from about 0 ppm to about 60 ppm, from about 0 ppm to about 50 ppm, from about 0 ppm to about 40 ppm, from about 0 ppm to about 30 ppm, from about 0 ppm to about 20 ppm, or from about 0 ppm to about 10 ppm.

[0172] KK2. The method of any of paragraphs U2-JJ2, wherein the sulfation reaction is carried out to less than 100% completion.

[0173] LL2. The method of paragraph KK2, wherein the sulfation reaction is carried out to 97%, 94%, or 90% completion.

[0174] MM2. A method for producing an ethoxylated sulfate surfactant, comprising scrubbing a reduced glycol sulfate ethoxylated sulfate surfactant described in any of paragraphs U-LL to remove at least a portion of the 1,4-dioxane.

[0175] A3. The surfactant comprises an ethoxylated fatty alcohol having no more than 100 ppm by weight of free glycol.

[0176] B3. The surfactant of paragraph A3, wherein the free glycol comprises an ethylene glycol oligomer.

[0177] C3. Ethylene glycol oligomer is HO(CH2CH2O) n H, where n is from 2 to about 30, preferably from 2 to about 25, more preferably from 2 to about 15, even more preferably from 2 to about 10, and most preferably from 2 to about 5.

[0178] D3. The surfactant described in any of paragraphs A3 to C3, wherein the amount of free glycol in the ethoxylated fatty alcohol is from about 0 ppm to about 100 ppm, preferably from about 0 ppm to about 90 ppm, more preferably from about 0 ppm to about 80 ppm, even more preferably from about 0 ppm to about 70 ppm, even more preferably from about 0 ppm to about 60 ppm, even more preferably from about 0 ppm to about 50 ppm, even more preferably from about 0 ppm to about 40 ppm, even more preferably from about 0 ppm to about 30 ppm, even more preferably from about 0 ppm to about 20 ppm, and most preferably from about 0 ppm to about 10 ppm.

[0179] E3. The surfactant of any of paragraphs A3-D3, wherein the ethoxylated fatty alcohol comprises 2-tridecyl alcohol ethoxylate, alcohol ethoxylate-2, 3-tridecyl alcohol, alcohol ethoxylate-1, alcohol ethoxylate 1.8, or a combination thereof.

[0180] F3. The surfactant comprises a sulfated ethoxylated alcohol having not more than 100 ppm by weight of sodium diethylene glycol monosulfate.

[0181] G3. The surfactant according to paragraph F3, wherein the amount of sodium diethylene glycol monosulfate is from about 0 ppm to about 100 ppm, from about 0 ppm to about 90 ppm, from about 0 ppm to about 80 ppm, from about 0 ppm to about 70 ppm, from about 0 ppm to about 60 ppm, from about 0 ppm to about 50 ppm, from about 0 ppm to about 40 ppm, from about 0 ppm to about 30 ppm, from about 0 ppm to about 20 ppm, or from about 0 ppm to about 10 ppm.

[0182] H3. The surfactant of paragraph F3 or G3, wherein the sulfated ethoxylated alcohol comprises sodium laureth-1 sulfate, sodium laureth-1.8 sulfate, sodium laureth-2 sulfate, sodium laureth-2.5 sulfate, sodium laureth-3 sulfate, sodium trideceth-2 sulfate, sodium trideceth-3 sulfate, or a combination thereof.

[0183] I3. A cleansing composition comprising a surfactant according to any one of paragraphs A3 to H3 and water.

[0184] J3. The cleansing composition of paragraph I3, wherein water is present at a level of from 10% to about 90%, preferably from about 20% to about 80%, more preferably from about 30% to about 75%, or even more preferably from about 40% to about 75%.

[0185] K3. A method for retarding dioxane conversion, comprising buffering the pH of an ethoxylated fatty alcohol feedstock to about 6 to about 11, preferably about 7 to about 10.5, more preferably about 7 to about 8, even more preferably about 9.5 to about 11, or most preferably about 10 to about 11, wherein the pH is measured as a 10% solution.

[0186] L3. A method for retarding dioxane conversion comprising buffering the pH of a sulfated ethoxylated alcohol surfactant feedstock to about 6 to about 11, preferably about 7 to about 10.5, more preferably about 7 to about 8, even more preferably about 9.5 to about 11, or most preferably about 10 to about 11, wherein the pH is measured as a 10% solution.

[0187] Dimensions and values ​​disclosed herein should not be understood as being strictly limited to the exact numerical values ​​recited. Instead, unless otherwise indicated, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as "40 mm" is intended to mean "about 40 mm."

[0188] All documents cited herein, including any cross-referenced or related patents or patent applications, and any patent applications or patents to which this application claims priority or benefit, are incorporated herein by reference in their entirety, unless expressly stated to the contrary. The citation of any document shall not be deemed to be prior art to any invention disclosed or claimed herein, or to teach, suggest, or disclose such invention, either alone or in combination with any other reference(s). Furthermore, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern.

[0189] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Claims

1. A surfactant comprising an ethoxylated fatty alcohol having 100 ppm by weight or less of free glycol, or a sulfated ethoxylated alcohol having 100 ppm by weight or less of sodium diethylene glycol monosulfate, The free glycol comprises an ethylene glycol oligomer, the ethylene glycol oligomer being HO(CH 2 CH 2 O) n H, where n is 2 to 30; A surfactant, wherein the amount of sodium diethylene glycol monosulfate is 0 ppm to 100 ppm.

2. The ethylene glycol oligomer is HO(CH 2 CH 2 O) n 2. The surfactant of claim 1 comprising the formula: H, where n is 2-25.

3. 3. The surfactant of claim 1 or 2, wherein the amount of free glycol in the ethoxylated fatty alcohol is from 0 ppm to 100 ppm.

4. 4. The surfactant of any one of claims 1 to 3, wherein the ethoxylated fatty alcohol comprises 2-tridecyl alcohol ethoxylate, alcohol ethoxylate-2, 3-tridecyl alcohol, alcohol ethoxylate-1, alcohol ethoxylate 1.8, or combinations thereof.

5. 2. The surfactant of claim 1, wherein the amount of sodium diethylene glycol monosulfate is from 0 ppm to 90 ppm.

6. 6. The surfactant of claim 1 or 5, wherein the sulfated ethoxylated alcohol comprises sodium laureth-1 sulfate, sodium laureth-1.8 sulfate, sodium laureth-2 sulfate, sodium laureth-2.5 sulfate, sodium laureth-3 sulfate, sodium trideceth-2 sulfate, sodium trideceth-3 sulfate, or combinations thereof.

7. A cleansing composition comprising the surfactant according to any one of claims 1 to 6 and water.

8. The cleansing composition of claim 7, wherein the water is present at a level of from 10% to 90%.

9. A surfactant described in any one of claims 1 to 6, wherein the ethoxylated fatty alcohol or the sulfated ethoxylated alcohol is obtained by extraction of free glycol with a polar solvent.

10. The surfactant of claim 9, wherein the polar solvent is water.

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