Blends of N-acyl alaninates with other N-acyl amino acid surfactants and their derivatives

Abstract

The surfactant composition comprises a homogeneous mixture of greater than 70% by weight of an N-acyl alaninate surfactant of Formula (I) and an N-acyl amino acid surfactant of Formula (II). A method for preparing a blend of N-acyl alaninate surfactant and an N-acyl amino acid surfactant includes combining (a) an alanine amino acid and (b) another amino acid, an anhydrous alkali salt of the other amino acid, or both, an anhydrous base, and a fatty alkyl ester of Formula (V) to form a mixture containing an alanine amino acid salt of Formula (III) and another amino acid salt of Formula (IV). The method further includes increasing the temperature of the mixture to 180°C or less to form a reaction mixture. The method further includes continuously removing alkyl alcohol from the reaction mixture and substantially clarifying the reaction mixture to form a blend. [Formula 1] JPEG2023551152000020.jpg19147

Description

[Technical Field]

[0001] FIELD OF THE DISCLOSURE The present disclosure relates generally to N-acylalaninates and derivatives, and N-acylalaninate blend compositions, having reduced amounts of impurities. [Background technology]

[0002] Surfactants are the single most important cleaning ingredient in cleaning products. Environmental regulations, consumer habits, and practices are forcing new developments in the surfactant industry to produce lower cost, higher performance, and environmentally friendly products.

[0003] Surfactants are key ingredients that play an important role in a variety of applications and consumer products, such as detergents, hard surface cleaners, fabric softeners, body washes, face washes, shampoo conditioners, conditioning shampoos, and other surfactant-based compositions. Summary of the Invention [Means for solving the problem]

[0004] Many catalogs and patents list surfactant choices that are too expensive to use.The cost is often multiplied due to the starting materials used to make such surfactants, inefficient reaction schemes, and / or the complex methods required for their manufacture to meet specific quality attributes.Therefore, there is a need for a new method for producing surfactant compositions that contain minimal impurities or additives at low cost.

[0005] Today, cleansing products are designed by formulators to perform multiple tasks, typically using two or more surfactants in their compositions. Chief among these is cleaning by promoting soil removal from the treated surface or substrate. Unfortunately, in any cleansing product, the surfactant can also act to remove beneficial substances, such as lipids, from the skin upon contact. Lipids on the skin, for example, help protect the skin from excessive moisture loss. Removing excess lipids can leave the skin prone to dryness. One solution to this problem is to utilize milder surfactants. Another solution is to replace the removed substances by depositing a benefit material on the skin. Amino acid-based surfactants are generally mild to the skin. The degree of mildness may depend on the specific properties of the amino acid and other factors, such as solution pH and the presence of other co-surfactants. There are several in vivo and ex vivo methods for assessing the relative mildness of surfactants. One such method measures the surfactant's ability to dissolve zein, a corn protein. Results from this method correlate with its skin irritation potential. Based on these results, all amino acid-based surfactants are milder than the stringent benchmark, sodium lauryl sulfate (SLS). Other studies have shown that the tendency of surfactants to cause protein denaturation and skin irritation is related to the charge density of the surfactant micelles. It is believed that when charged surfactants bind to proteins, they form micelle-like structures on their backbones, causing either denaturation or swelling, resulting in enhanced penetration of the surfactant into deeper layers of the skin and a biological response manifesting as irritation. Studies have shown that when determining Franz cell penetration of methylparaben into the skin, sodium laurate, the primary active in soap bars, was found to cause the most damage.SLS causes less damage than sodium laurate, and the N-acyl amino acid surfactants evaluated, namely, N-acyl alaninates, N-acyl sarcosinates, N-acyl glycinates, N-acyl glutamates, acyl N-methyl taurates, and alkali metal salts of acyltaurates, were found not to cause any damage and are known "mild" surfactants available to formulators.

[0006] Among these mild surfactants, taurates are slightly to moderately soluble in water. For example, the solubility of sodium N-methyl cocoyl taurate in water is reported to be 10 grams per liter at 20°C. This surfactant is commercially available as a 30% solids paste, which can pose some handling challenges, making it more difficult to incorporate into formulations, or requiring solubilization in aqueous media using other surfactants, which may or may not be part of the same formulation. Its non-methylated counterpart, cocoyl taurate, has lower water solubility. In contrast, N-cocoyl alaninate, N-cocoyl glycinate, N-cocoyl glutamate, and N-lauroyl sarcosinate surfactants exhibit higher water solubility and are sold as 30% solids clear liquid aqueous solutions.

[0007] N-acyl alaninate (and other amino acid-based) surfactants can be commercially produced from the corresponding fatty acid chlorides and amino acids using Schotten-Baumann chemistry as shown in Equation 1.

[0008] [ka]

[0009] This amidation reaction is typically carried out in water, although the use of mixed water-solvent systems has been reported. Typically, the resulting sodium N-acyl amino acid surfactants are obtained in the form of aqueous compositions containing 20-30% active material, always along with high levels of undesirable inorganic salts (NaCl). The latter can be removed via an additional post-reaction step, which can add significant cost and process complexity. This surfactant preparation method is expensive and requires the preparation of fatty acid chlorides using chlorinating agents such as phosphorus trichloride (PCl3), phosphorus pentachloride (PCl5), thionyl chloride (SOCl2), oxalyl chloride (COCl2), or phosgene (a toxic gas). These chlorinating agents can be highly reactive and toxic, requiring highly specialized handling and metallurgy. Furthermore, depending on the specific chemistry and process used, the separation of fatty acid chlorides from by-products and the catalysts used has been challenging. Therefore, the product may contain undesirable impurities that can be carried over to the synthesis of the corresponding surfactant.

[0010] One attempt to overcome these drawbacks is the synthesis of N-acylglycinates and N-acylalaninates by reacting the corresponding amino acids with the fatty acids themselves. This method produced highly colored (yellow) surfactant compositions containing relatively high levels of acylated di- and tri-peptide by-products along with significant levels of unreacted fatty acids. Furthermore, this method requires a 100-200% molar excess of fatty acids.

[0011] The preparation of N-acyltaurates (or N-acyltaurides, as others have named them) has also been reported to occur by direct condensation of a carboxylic acid with taurine (alkali salt of 2-aminoalkanesulfonic acid), as shown in Equation 2. However, this reaction requires the removal of water, as well as high temperature and the use of an inert atmosphere. This direct amidation reaction can be carried out in the presence of a catalyst, such as zinc oxide, hypophosphorous acid, or boric acid. Decomposition by-products have been reported, resulting in poor product yields and unacceptable product discoloration and odor. Typically, the carboxylic acid is said to be used in a ≥30 molar excess compared to taurine. To produce fatty acid-free N-acyltaurates by this chemical approach, the crude reaction mixture is subjected to additional process steps, such as distillation, extraction, recrystallization, or a combination thereof.

[0012] [ka]

[0013] Fatty alkyl esters have also been used as starting materials. For example, methyl laurate can be reacted with the sodium salt of an amino acid and sodium methoxide in methanol in a pressure reactor at a reaction pressure ranging from 5 to 50 psig depending on the reaction temperature. The conversion to N-acylsarcosinate from this reaction can be as low as 22%, while the conversion to N-acylalaninate can be as high as 67%. The N-acylamino acid surfactant formed can be isolated by adding more methanol to the crude reaction mixture, filtering it, washing the resulting solid with more methanol, and finally drying the isolated surfactant in an oven. The filtrate can be concentrated and analyzed to determine the percentage of methyl laurate and / or the sodium salt of the amino acid, which can then be reused in the next batch. Therefore, a further drawback of this approach is the need for several process steps to isolate the reaction product.

[0014] In yet another conventional reaction, N-acyl amino acid surfactants are prepared using a polyol at 50-70% by weight of the combined weight of the amino acid salt and methyl ester. However, the polyol, glycerol, and / or propylene glycol used remain in the final product mixture. Di-peptide impurities are found in the surfactant composition, the levels of which vary depending on the level of polyol used in the reaction.

[0015] There is a need to design and create mild cleansing products that can come into contact with skin, hair, and other sensitive body parts (e.g., eyes, nose) during use. Typically, these formulations require the use of two or more mild surfactants that are easy to incorporate into cleansing formulations. There is also a need for N-acylalaninate and N-acyltaurate compositions that are produced with low levels of by-products and impurities, and low levels of solvents or additives.

[0016] The present disclosure addresses these needs by providing a surfactant composition comprising a homogeneous mixture of greater than 70% by weight of an N-acyl alaninate surfactant of formula (I) and an N-acyl amino acid surfactant of formula (II), where formulas (I) and (II) are provided below.

[0017] [ka] R is C5~C 21 alkyl substituents, wherein R1 represents H or a C1-C4 alkyl radical, R2 represents H, a C1-C4 alkyl radical, or a C1-C4 hydroxyalkyl, and R3 represents the functional moieties COOM and CH2-SO3M, where M is a cationic group selected from the group consisting of alkali metal salts and hydrogen. The surfactant composition is substantially free of solvent and NaCl.

[0018] The present disclosure further relates to a method for preparing a blend of N-acyl alaninate surfactants and N-acyl amino acid surfactants. The method includes combining (a) an alanine amino acid with (b) another amino acid, an anhydrous alkali salt of the other amino acid, or both, an anhydrous base, and a fatty alkyl ester of formula (V) to form a mixture. The mixture includes an alanine amino acid salt of formula (III) and another amino acid salt of formula (IV). Formulas (III), (IV), and (V) are shown below.

[0019] [ka] M is a cationic group selected from alkali metal salts;

[0020] [ka] R1 represents H or a C1-C4 alkyl radical, R2 represents H, a C1-C4 alkyl radical, or a C1-C4 hydroxyalkyl, R3 represents the functional moiety COOM and CH2-SO3M, and M is a cationic group selected from alkali metal salts;

[0021] [ka] R is C5~C 21 R' is selected from alkyl substituents of C1 or greater, preferably methyl.

[0022] The method further includes increasing the temperature of the mixture to no more than 180°C, preferably no more than 160°C, and more preferably no more than 150°C to form a reaction mixture, continuously removing alkyl alcohol from the reaction mixture, and allowing the reaction mixture to substantially clarify to form a blend.

[0023] In another aspect, the present disclosure relates to a consumer product cleaning or personal care composition comprising from about 0.001% to about 99.999% by weight, preferably from about 0.1% to about 80% by weight, of a homogeneous mixture of an N-acyl alaninate as described herein and another N-acyl amino acid surfactant, and from 0.001% to about 99.999% by weight of one or more additional cleaning components or one or more additional personal care components, based on the total weight of the composition. DETAILED DESCRIPTION OF THE INVENTION

[0024] Features and advantages of the present disclosure will become apparent from the following description, including examples intended to give a broad representation of the disclosure. Various modifications will become apparent to those skilled in the art from this description and practice of the disclosure. The scope is not intended to be limited to the particular forms disclosed, but rather the disclosure covers all modifications, equivalents, and alternatives falling within the spirit and scope of the disclosure as defined by the claims.

[0025] As used herein, the articles including "the," "a," and "an," when used in a claim or the specification, are understood to mean one or more of what is claimed or described.

[0026] As used herein, the terms "include", "includes" and "including" are meant to be open-ended.

[0027] As used herein, the terms "substantially free of" or "substantially free from" refer to either a complete absence or minimal amount of a component simply as an impurity or unintended by-product of another component. A composition that is "substantially free of" a component means that the composition contains less than about 0.5%, 0.25%, 0.1%, 0.05%, or 0.01%, or even 0%, by weight of the composition, of the component.

[0028] As used herein, the term "solid" includes granule, powder, flake, noodle, needle, extrudate, ribbon, bead, and pellet product forms that contain less than about 0.5%, 0.25%, 0.1%, 0.05%, or 0.01%, or even 0%, water by weight of the composition.

[0029] As used herein, "homogeneous" refers to a mixture composed of two or more different substances whose chemical identity is maintained and whose composition is uniform throughout the mixture.

[0030] As used herein, a "clear mixture" refers to a mixture of two or more chemicals that appears as one phase, without any separate phases.

[0031] As used herein, "personal cleansing compositions" includes personal cleansing products such as shampoos, conditioners, conditioning shampoos, shower gels, liquid hand washes, facial cleansers, and other surfactant-based liquid compositions.

[0032] It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification is intended to include every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.

[0033] In this description, all concentrations are by weight of the composition unless otherwise indicated.

[0034] 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."

[0035] N-acyl alaninate surfactant blend composition The surfactants in the homogeneous N-acylalaninate blend compositions disclosed herein have the following general formulas (I) and (II):

[0036] [ka] In the formula, R is C5 to C 21 alkyl substituents, where R1 represents H or a C1-C4 alkyl radical, R2 represents H, a C1-C4 alkyl radical, or a C1-C4 hydroxyalkyl, and R3 represents the functional moieties COOM and CH2-SO3M, where M is a cationic group selected from the group consisting of alkali metal salts and hydrogen. 7-17The alkyl substituent may be branched or unbranched, preferably unbranched.

[0037] The surfactants in the N-acylalaninate blends described herein are typically not single compounds as suggested by their general formulas (I) and (II); rather, as one skilled in the art will readily understand, they comprise a mixture of several homologs having various chain lengths and molecular weights. The alkyl chains on the surfactants in the N-acylalaninate blends described herein can be either saturated or unsaturated, and are preferably saturated.

[0038] The homogeneous N-acyl alaninate surfactant blend composition of the present disclosure comprises at least 50% by weight of a homogeneous blend of surfactants of formulas (I) and (II). The composition preferably comprises 70-95% by weight of the homogeneous blend of surfactants of formulas (I) and (II). For example, the composition of the present disclosure may comprise 70% by weight, preferably greater than 75% by weight, and more preferably greater than 85% by weight of a mixture of an N-acyl alaninate of formula (I) and an N-acyl amino acid surfactant of formula (II), including all values ​​within these ranges and any ranges created thereby.

[0039] The homogeneous N-acylalaninate surfactant blend composition of the present disclosure further comprises a fatty acid, which may be present as a free fatty acid or in the form of a fatty acid soap, in an amount ranging from 1 to about 10% by weight, preferably 2 to 7% by weight, and more preferably 3 to 5% by weight, including all values ​​within these ranges and any ranges created therewith.

[0040] Beneficially, the homogenous N-acylalaninate surfactant blend compositions of the present disclosure may be substantially free of impurities including water, salt (NaCl), polyol solvents, acylated di- and tri-peptide by-products, and methanol. The compositions of the present disclosure may contain less than 5%, less than 2%, less than 1%, less than 0.1%, substantially free, and in some particularly preferred cases, none of one or any combination of these impurities.

[0041] The present disclosure further encompasses concentrated compositions, often referred to as pastes, as well as solids such as powders and tablets, which can be combined with various adjunct ingredients (e.g., water) to make a variety of detergent products, including personal cleaning compositions and laundry detergents.

[0042] Typically, inorganic salts (NaCl) are added to cleaning formulations made with sulfated surfactants to thicken the product. Surprisingly, it has been found that adding inorganic salts to formulations that are substantially free of sulfate-containing surfactants in the presence of cationic conditioning polymers, and / or using high inorganic salts containing sulfate-free surfactants, can cause product instability due to the formation of gel-like surfactant-polymer complexes in the composition. Therefore, it is desirable to avoid or minimize the addition of NaCl to the formulation and / or use raw materials with low inorganic salt (NaCl) content. Commercially available sulfate-free surfactants, such as sodium cocoyl alaninate, sodium N-methyl cocoyl taurate, sodium cocoyl glycinate, and other amino acid-based surfactants, typically contain high levels of inorganic salts, such as 5% or more. The use of these high salt (e.g., NaCl) raw materials in sulfate-free surfactant-based cleaning formulations can cause the formation of undesirable gel-like surfactant-polymer complexes in the product before use. The surfactant compositions of the present disclosure described herein may enable the formulation of stable cleaning products that are substantially free of sulfate-containing surfactants.

[0043] Method for making homogeneous N-acyl alaninate surfactant blend compositions The method described herein allows for the preparation of homogeneous N-acyl alaninate surfactant blends with low levels of impurities. The traditional Schotten-Baumann acid chloride route to N-acyl alaninate and other amino acid surfactants generates NaCl and other impurities, resulting in undesirable products. Furthermore, other reactions for making N-acyl alaninate and other amino acid surfactants use low-boiling solvents and are carried out in sealed reactors under pressure rather than atmospheric conditions. High-pressure reaction conditions are inherently more dangerous, time-consuming, complicated, and expensive, making them undesirable. Others use high-boiling solvents, such as polyols, glycerol, and propylene glycol, to carry out reactions at atmospheric conditions, but these difficult-to-remove solvents remain with the surfactant.

[0044] The present disclosure further relates to a method for preparing a blend of N-acyl alaninate surfactants and N-acyl amino acid surfactants. The method includes combining (a) an alanine amino acid with (b) another amino acid, an anhydrous alkali salt of the other amino acid, or both, an anhydrous base, and a fatty alkyl ester of formula (V) to form a mixture. The mixture includes an alanine amino acid salt of formula (III) and another amino acid salt of formula (IV). Formulas (III), (IV), and (V) are shown below.

[0045] [ka] M is a cationic group selected from alkali metal salts;

[0046] [ka] R1 represents H or a C1-C4 alkyl radical, R2 represents H, a C1-C4 alkyl radical, or a C1-C4 hydroxyalkyl, R3 represents the functional moiety COOM and CH2-SO3M, and M is a cationic group selected from alkali metal salts;

[0047] [ka] R is C5~C 21 R' is selected from alkyl substituents of C1 or greater, preferably methyl.

[0048] The method further includes increasing the temperature of the mixture to no more than 180°C, preferably no more than 160°C, and more preferably no more than 150°C to form a reaction mixture, continuously removing alkyl alcohol from the reaction mixture, and allowing the reaction mixture to substantially clarify to form a blend.

[0049] In embodiments, combining (a) alanine amino acid with (b) another amino acid, anhydrous alkali salt of the other amino acid, or both, anhydrous base, and a fatty alkyl ester of Formula (V) to form a mixture comprises preparing a suspension of the alanine amino acid salt of Formula (III) and the other amino acid salt of Formula (IV) by adding anhydrous base to the alanine amino acid and the other amino acid, and contacting the suspension with the fatty alkyl ester of Formula (V) to form a mixture. In embodiments, the mixture comprises less than about 50%, less than about 40%, less than about 35%, less than about 30%, less than about 25%, less than about 20%, less than about 15%, less than about 10%, less than about 5%, and all ranges therein formed of taurine, sodium N-methyl taurine, or both.

[0050] In embodiments, combining (a) alanine amino acid with (b) other amino acids, anhydrous alkali salts of other amino acids, or both, anhydrous base, and a fatty alkyl ester of Formula (V) to form a mixture comprises combining anhydrous base with a fatty alkyl ester of Formula (V) to form a premix, and then adding (a) alanine amino acid and (b) other amino acids, anhydrous alkali salts of other amino acids, or both to the premix to form a mixture. In embodiments, the mixture comprises at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 95%, and all ranges therein created, of taurine, sodium N-methyl taurine, or both of the mixture.

[0051] It is contemplated that it may be beneficial to combine the anhydrous base and fatty alkyl ester in a reactor before adding alanine amino acid and other amino acids (or their anhydrous alkali salts) to form the alanine amino acid salt of Formula (III) and other amino acid salts of Formula (IV) in situ to achieve a well-dispersed mixture. As a non-limiting example, adding anhydrous base to a mixture containing alanine amino acid and taurine (or sodium N-methyl taurine), where increasing the proportion of starting taurine (or sodium N-methyl taurine) to create a surfactant blend containing 40 wt.% or more of taurate surfactant, resulted in a slurry, thick paste, or agglomerate-like mixture of the respective amino acid salts, which was more difficult to disperse when the fatty alkyl ester came into contact with it. Therefore, when the other amino acid includes taurine (or sodium N-methyl taurine) in an amount such that the surfactant blend contains at least about 40% by weight of the taurate or N-methyl taurate surfactant, it may be desirable to combine the anhydrous base with the fatty alkyl ester of formula (V) to form a premix, and then add the alanine amino acid and other amino acids (or their anhydrous alkali salts) to the premix to form a mixture. Combining the anhydrous base with the fatty alkyl ester of formula (V) to form a premix before adding the alanine amino acid and other amino acids (or their anhydrous alkali salts) may result in a more dispersed mixture than combining the anhydrous base, alanine amino acid, other amino acids (or their anhydrous salts), and fatty alkyl ester of formula (V) all at once, or combining the anhydrous base, alanine amino acid, and other amino acids (or their anhydrous salts) to form a suspension and then adding the fatty alkyl ester of formula (V) to the suspension.

[0052] The anhydrous base may comprise a C1-C4 alkoxide, preferably sodium or potassium methoxide, and may be used in an amount ranging from 1.00 to 1.50 moles, preferably 1.02 to 1.20 moles, and more preferably 1.05 to 1.10 moles per mole of unneutralized combined amino acid, including all values ​​within these ranges and any ranges created thereby.

[0053] The method for preparing a homogeneous N-acylalaninate surfactant blend further comprises contacting a mixture comprising the amino acid salts of formulas (III) and (IV) with a fatty alkyl ester of formula (V):

[0054] [ka] wherein R' is a C1 or higher alkyl substituent, preferably methyl. The method may further include increasing the temperature of the two-phase mixture to 180°C, preferably 160°C, and more preferably 150°C to form a reaction mixture, and continuously removing the alkyl alcohol from the reaction mixture. For example, the temperature of the mixture may be from about 65°C to about 180°C, or preferably from about 90°C to about 150°C, including all values ​​within these ranges and any ranges created thereby.

[0055] Without wishing to be bound by theory, the lower melting point of the first N-acyl amino acid surfactant helps to maintain the second, higher melting point N-acyl amino acid surfactant formed in a more easily processable blend, and thus, for example, N-acyl alaninate acts as a solvent for the other surfactants formed in the reaction ("dissolving"). According to the present disclosure, the alanine amino acid is a naturally occurring α-amino acid, a non-natural amino acid (opposite "D" stereochemistry), or a racemic mixture. The other amino acid is selected from the group consisting of sarcosine, glycine, serine, proline, taurine, and N-methyltaurine.

[0056] The method of the present disclosure can be successfully applied when alanine amino acid is combined with the anhydrous alkali metal salt form of another amino acid. Thus, it is possible to use a) other naturally occurring amino acids, such as sodium glycinate, and b) sodium or potassium salts of aliphatic aminosulfonic acids having 2 to 4 carbon atoms, such as sodium N-methyltaurine. Those skilled in the art will also understand that either two different amino acids (e.g., alanine and glycine) or an amino acid / anhydrous amino acid alkali metal salt combination (e.g., alanine / sodium N-methyltaurine) can be used simultaneously or sequentially during the method. Those skilled in the art will recognize that when a fatty alkyl methyl ester and an alkali metal salt of an amino acid are mixed together, they exist as two separate phases. Applicants surprisingly found that the starting materials react under the process conditions of the present disclosure. Once the reaction has occurred to some extent, the mixture may become clear. Without wishing to be bound by theory, applicants hypothesize that the surfactant formed during the reaction facilitates bringing the reactants together to the point where the mixture appears as a clear, one-phase mixture and any remaining unreacted reactants are solubilized in the reaction mixture, which is believed to be important for achieving high reaction conversions.

[0057] Suitable anhydrous bases for use include alkali metals such as sodium, lithium, and potassium; alloys of two or more alkali metals such as sodium-lithium alloys and sodium-potassium alloys; alkali metal hydrides such as sodium, lithium, and potassium hydrides; and preferred alkali metal alkoxides, particularly those containing from about 1 to about 4 carbon atoms, such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium n-propoxide, potassium n-propoxide, sodium isopropoxide, potassium isopropoxide, sodium butoxide, potassium butoxide, sodium isobutoxide, potassium isobutoxide, sodium sec-butoxide, potassium sec-butoxide, and potassium tert-butoxide. The alkoxides are available in solid form or as a solution in the alcohol from which the alkoxide is derived.

[0058] The relative molar amount of alkoxide added in step i) is in the range of 1.00 to 1.50 moles, preferably 1.02 to 1.20 moles, and more preferably 1.05 to 1.10 moles per mole of unneutralized combined amino acid, including all values ​​within these ranges and any ranges created therein. The alkoxide not consumed in the neutralization catalyzes the reaction between the amino acid salt and the fatty alkyl ester. Thus, in the methods described herein, the preferred amount of alkoxide catalyst is in the range of 2 to 20 mole percent, more preferably 5 to 10 mole percent, including all values ​​within these ranges and any ranges created therein.

[0059] As used herein, the terms "fatty alkyl ester" and "fatty acid ester" refer to any compound from which the alcohol moiety is easily removed, preferably an ester of a volatile alcohol, e.g., C 1~4It is intended to include an alcohol (preferably methyl). Volatile alcohols are highly desirable. Methyl esters are the most preferred ester reactants. Suitable ester reactants can be prepared by the reaction of diazoalkanes with fatty acids or can be derived by alcoholysis from fatty acids naturally occurring in fats and oils. Non-limiting examples are methyl octanoate (caprylate), methyl decanoate (caprate), methyl dodecanoate (laurate), methyl tetradecanoate (myristate), methyl hexadecanoate (palmitate), methyl octadecanoate (stearate), methyl oleate, ethyl dodecanoate (laurate), ethyl tetradecanoate (myristate), isopropyl dodecanoate (laurate), isopropyl tetradecanoate (myristate), and mixtures thereof. Suitable fatty acid esters can be derived from synthetic or natural saturated or unsaturated fatty acids. Non-limiting examples of saturated fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, and stearic acid. Mixtures of fatty acids derived from coconut oil, cottonseed oil, palm kernel oil, soybean oil, cottonseed oil, rapeseed oil, safflower oil, canola oil (low erucic acid), and corn oil, and mixtures thereof. Coconut oil is most preferred.

[0060] The fatty alkyl ester is preferably highly purified to remove color / odor materials, oxidation products, and their precursors. The free fatty acid level should be less than about 0.1% by weight of the ester, preferably less than about 0.05% by weight. In addition, the fatty acid alkyl ester should have the lowest possible water content, since any water present can react with the alkoxide catalyst, inhibit the amidation reaction, and increase the soap level.

[0061] The molar ratio of fatty alkyl ester added in step ii) is in the range of 0.90 to 1.50 moles per mole of combined amino acid salt, preferably 0.95 to 1.20 moles per mole of combined amino acid salt, or more preferably 1.00 to 1.05 moles per mole of combined amino acid salt, including all values ​​within these ranges and any ranges created thereby. As shown in the examples, when the combined amino acid salt and fatty alkyl ester are used in approximately equimolar amounts, a highly active surfactant composition with low levels of impurities is possible without further processing steps. Using excess fatty alkyl ester results in a surfactant composition contaminated with unreacted fatty alkyl ester, thus requiring further processing for its removal. Using excess amino acid salt is less desirable because amino acid salts are more expensive than fatty alkyl esters, do not have surface-active properties, and recovering unreacted amino acid salts from the surfactant mixture is difficult and expensive.

[0062] Surprisingly, the reaction between a mixture of an alanine salt of formula (III) and another amino acid salt of formula (IV) and a fatty alkyl ester of formula (V) can be carried out at atmospheric pressure while continuously distilling off alkyl alcohol (e.g., methanol) from the reaction mixture. Temperature conditions for the amidation reaction can range from 65°C to about 180°C, or preferably from about 90°C to about 150°C, including all values ​​within these ranges and any ranges created thereby. The progress of the reaction can be monitored and / or quantitatively monitored by monitoring the amount of alkyl alcohol collected. 1 The reaction temperature can be monitored by H NMR or other analytical techniques. The final homogeneous reaction mixture of N-acyl alaninate surfactant blends made under these relatively mild conditions can be fluid at the amidation reaction temperature. The high activity surfactants can be flaked, prilled, milled, pelletized, and / or formed into beads, noodles, needles, and ribbons by methods known to those skilled in the art.

[0063] The reaction may utilize an inert gas headspace to help reduce the level of oxygen available during the reaction. The reduced oxygen level helps reduce the amount of oxidation of the reaction components. Oxidation of the components can cause discoloration. A suitable example of an inert gas that may be utilized is nitrogen.

[0064] Additionally, the advantage of carrying out the reaction described herein at atmospheric pressure or even negative pressure is that the resulting surfactant can be substantially free of any solvent (if desired). Additionally, the vapor of the alkyl alcohol, e.g., methanol, can be condensed and recovered outside the reactor. This collection of alkyl alcohol vapor can be reused to produce more methyl esters. The resulting surfactant can have a reduced amount of fatty acid methyl esters compared to conventional methods.

[0065] Additionally, the inventors have surprisingly found that the amount of fatty acid methyl ester in the resulting composition can vary depending on the composition of the blended surfactant.For example, when the surfactant blend contains at least about 60% by weight of alaninate, about 25% by weight or less of taurate can produce a high level, for example, about 85% by weight or more of surfactant in the composition obtained by the method of the present disclosure.Similarly, at a high level, for example, at least about 60% by weight of alaninate, the level of fatty acid methyl ester in the resulting surfactant can be less than about 5% by weight, or more preferably less than about 3% by weight, including all values ​​within these ranges and any ranges created thereby.

[0066] In contrast, when alaninate is present at about 35 wt% or less and taurate is present at about 40 wt% or more, the surfactant yield in the resulting composition can be about 75 wt% or more. Additionally, in this configuration, the level of fatty acid methyl ester in the resulting composition can be about 15 wt%, preferably less than about 10 wt%, or more preferably less than 5 wt%, including all values ​​within these ranges and any ranges created thereby.

[0067] This same principle is believed to be applicable to other blends of alaninate and taurate or N-methyl taurate. For the methods of the present disclosure, the weight percentage of taurate or N-methyl taurate can be about 60% by weight or less, preferably about 40% by weight or less, or more preferably about 30% by weight or less. For example, the weight percentage of taurate or N-methyl taurate can be about 5% by weight to about 60% by weight, preferably about 5% by weight to about 40% by weight, or more preferably about 5% by weight to about 30% by weight, including all values ​​within these ranges and any ranges created thereby.

[0068] In contrast, for the methods of the present disclosure, the weight percentage of alaninate, either independently or in combination with glycinate, sarcosinate, serinate, prolinate, or a combination thereof, can be about 40% by weight or more, preferably 60% by weight or more, or more preferably 70% by weight or more. For example, the weight percentage of alaninate, either independently or in combination with glycinate, sarcosinate, serinate, prolinate, or a combination thereof, can be about 40% by weight to about 90% by weight, preferably about 60% by weight to about 90% by weight, or more preferably about 70% by weight to about 90% by weight, including all values ​​within these ranges and any ranges created thereby.

[0069] To make a pumpable surfactant composition (pumpable at or below 50°C), the active surfactant without any further purification can be diluted in an amount of water between 20 and 70 percent by weight of the high active surfactant, preferably between about 25 and about 50 percent by weight of the high active surfactant. Alternatively, water can be added to the high active surfactant under good mixing, preferably at a temperature below 120°C, more preferably below 100°C. The amount of water required will depend on the target surfactant activity level, target viscosity, and the solubility behavior of the surfactant. Solid forms of surfactants—powders, flakes, pellets, beads, needles, noodles—can also be dissolved in water to make a pumpable surfactant composition for formulators to easily incorporate into cleaning formulations.

[0070] The disclosed method minimizes the levels of acylated di- and tri-peptide by-products and soaps formed by using low catalyst loadings, excluding water from the amidation reaction, and gradually increasing the reaction temperature from 90°C to about 150°C.

[0071] The method of the present disclosure can be carried out in batch, semi-continuous, or continuous mode using suitable reactor configuration.A conventional stirred tank batch reactor equipped with a means for heating reactants, a vapor column and condenser for collecting volatile alkyl alcohol, an efficient agitator capable of stirring the reaction product mixture, a means for blanketing the reactor contents with nitrogen, and optionally a vacuum system capable of achieving a vacuum of less than 20 mm Hg can be used to prepare the homogeneous N-acyl alaninate surfactant blend composition disclosed herein.

[0072] Other reactors useful in the present disclosure are suitably devices capable of mixing a liquid and solid mixture of liquid and solid materials using shear forces. In static housings, movement of the reaction mixture is effected by an internal mechanical stirring or mixing device. The reactor can be a kneader or mixer equipped with a sigma blade, masticator blade, or plow-type agitator. Additional useful devices include horizontal or vertical compulsory mixers equipped with a mixing tool, such as a sigma blade, masticator blade, plow-type agitator, or throwing paddle, in combination with a cutting rotor.

[0073] Suitable horizontal compulsory mixers are those equipped with a mixing tool or a combination of mixing tools, such as sigma blades, masticator blades, or plow-type agitators, in combination with a cutting rotor mounted on a drum, more preferably those operating at a Froude number of 0.1 to 6, preferably 0.25 to 5, more preferably 0.4 to 4, and equipped with a mixing tool or a combination of mixing tools, such as sigma blades, masticator blades, or plow-type agitators, in combination with a cutting rotor mounted on a drum. Without wishing to be bound by theory, the Froude number, Fr, plays a key role in the processing of the mixing method. This dimensionless quantity indicates the relationship between the inertial force acting on moving particles and gravity, where the following equation is applicable: Fr=v 2 / rg During the ceremony, v=peripheral speed [m / s] r = radius of mixing drum [m] g=gravitational acceleration [m / s 2 ] v=π×D×n / 60 During the ceremony, D = diameter of mixing drum [m] N = shaft rotation speed [rpm]

[0074] The homogeneous N-acylalaninate surfactant blending process described herein has many advantages over known commercial manufacturing methods, including: 1) High conversions and yields can be achieved while avoiding tedious purification steps and attendant product losses. 2) Fewer chemical engineering unit operations, which can result in significant reductions in energy consumption. 3) As described herein, it does not contain toxic and hazardous reagents, thus eliminating the problems of handling these materials. 4) The resulting surfactant product is substantially free of solvent, which would otherwise have to be removed through additional post-reaction treatment steps. 5) A homogeneous blend of mild surfactants composed of N-acyl alaninates and other N-acyl amino acid surfactants is produced from the same starting fatty alkyl ester feedstock in the same reactor via one reaction. 6) A low-cost and efficient method for producing homogeneous blends of mild surfactants in solid form composed of N-acyl alaninates and other N-acyl amino acid surfactants. The solid form (water-free) of mild surfactants is advantageous for some applications. 7) A low-cost and efficient method for producing aqueous concentrates composed of a homogenous blend of mild surfactants composed of N-acyl alaninates and other N-acyl amino acid surfactants made in the same reactor via a single reaction. 8) Avoids the use of alternative manufacturing methods to separately make the acyl N-methyl taurate and acyl taurate surfactants required in the blended cleaning composition, which require very high temperatures when generating salts (NaCl) via Schotten-Baumann chemistry or using excess fatty acids (which must be removed) via direct amidation reactions.

[0075] Application and Use In another aspect, the present disclosure relates to a consumer product cleaning or personal care composition comprising, based on the total weight of the composition, from about 0.001% to about 99.999% by weight, preferably from about 0.1% to about 80% by weight, of a homogeneous N-acylalaninate surfactant blend as described herein, and from 0.001% to about 99.999% by weight of one or more additional cleaning components or one or more additional personal care components. In various embodiments, the at least one cleaning component is selected from the group consisting of surfactants, enzymes, builders, alkali systems, organic polymeric compounds, hueing dyes, bleaching compounds, alkanolamines, soil suspending agents, anti-redeposition agents, corrosion inhibitors, and mixtures thereof. In some cases, the composition is selected from the group consisting of granular detergents, detergent bars, liquid laundry detergents, liquid hand dishwashing compositions, hard surface cleaners, tablets, disinfectants, industrial cleaners, highly compressed liquids, powders, and decontaminants. In one class of cases, the composition is enclosed within a sachet or multi-compartment pouch containing both a solid and a liquid compartment.

[0076] In some embodiments, the at least one personal care component is selected from the group consisting of oils, emollients, moisturizers, carriers, extracts, vitamins, minerals, anti-aging compounds, surfactants, solvents, polymers, preservatives, antibacterial agents, waxes, particles, colorants, dyes, fragrances, and mixtures thereof. In various cases, the composition is a shampoo, hair conditioner, hair treatment, facial soap, body wash, body soap, foam bath, makeup remover, skin care product, acne control product, deodorant, antiperspirant, shaving aid, cosmetic, depilatory, fragrance, and mixtures thereof. In one class of cases, the composition is delivered in a form selected from the group consisting of wipes, cloths, bars, liquids, powders, creams, lotions, sprays, aerosols, foams, mousses, serums, capsules, gels, emulsions, doe feet, roll-on applicators, sticks, sponges, ointments, pastes, emulsion sprays, tonics, cosmetics, and mixtures thereof. In various embodiments, the composition is further comprised in a product selected from the group consisting of a device, an implement, an applicator, an implement, a comb, a brush, a substrate, and mixtures thereof. In some embodiments, the composition is dispensed from an article selected from the group consisting of a bottle, a jar, a tube, a sachet, a pouch, a container, a bottle, a vial, an ampoule, a compact, a wipe, and mixtures thereof. [Example]

[0077] Examples 1, 2, and 3 demonstrate the synthesis / preparation / manufacture of greater than 85% by weight homogeneous sodium N-acylalaninate surfactant blends that are substantially free of solvent and sodium chloride (NaCl).

[0078] Reaction analysis 1 1 H NMR analysis was performed. The reaction product and the internal standard (IS) were weighed in a scintillation vial using a precision balance (0.1 mg readability). D2O (heavy water) was added to the vial to completely dissolve the sample and the internal standard. 1H NMR spectra were standardized 1 The NMR data were recorded at 600 MHz using a H pulse sequence, a pulse width of 12.00, a delay of 60 seconds, and an acquisition time of 2.59 seconds. The NMR data were processed using MestReNova 10.0.2. The integral of the peak at δ 4.15 ppm for the methine (-CH-) group was used to calculate the weight percent of the N-acylalaninate surfactant. The integral of the peaks at 3.56 and 3.08 ppm for the methylene group (-CON(H)-CH2-CH2-SO3Na) was used to calculate the weight percent of the taurate surfactant. The integral of the peaks at 3.79 and 3.72 ppm for the methylene group (-CH2-SO3Na) was used to calculate the weight percent of the N-methyl taurate surfactant. The integral of the peak at 3.74 ppm for the methylene group (-CON(H)-CH2-COONa) was used to calculate the weight percent of the glycinate surfactant. The triple integral at δ 2.16 ppm for the methylene (-CH2-) adjacent to the carboxyl group was used to calculate the weight percent of fatty acid soap. The integral of the peak at δ 3.30 ppm for the methine (-CH-) group was used to calculate the weight percent of unreacted alanine sodium salt. The single integral at δ 3.65 ppm for the methyl (CH3-) was used to calculate the weight percent of any remaining fatty alkyl methyl ester. The integrals were compared to the integral area of ​​the IS and used in the calculations. The following equations were used to calculate the weight percent of each species:

[0079]

number

[0080] Example 1 Synthesis of blends of sodium lauroyl / myristoyl alaninate and sodium lauroyl / myristoyl taurate A series of experiments were conducted using a glass reaction vessel. It was equipped with a stirrer with a Teflon blade, a Dean-Stark trap with a condenser, a nitrogen inlet, an addition funnel, and a thermocouple connected to a temperature control device. The reactor was heated using a heating mantle plugged into the temperature control device. The reactor was charged with L-alanine (80.99 g, 0.90 mol), taurine (2-aminoethanesulfonic acid, 33.20 g, 0.26 mol), and 25 wt% sodium methoxide solution (276.52 g, 1.28 mol). The contents of the reactor were heated to 65-68 °C with stirring under nitrogen. At this point, CE1270 (257.00 g, 1.16 mol)—a methyl laurate / methyl myristate mixture from P&G Chemicals—was added to the reactor through the addition funnel (30-40 min) while maintaining good mixing, and the temperature was set to 100 °C. The evaporated methanol was collected in a Dean-Stark flask. After reaching 100°C, the reaction temperature was gradually increased to 125°C. The initially two-phase reaction became one-phase during this time, and the reaction was considered complete when the methanol stopped condensing (2.5 hours). The molten product was poured from the reactor and allowed to cool to ambient temperature. Quantitative 1 H NMR (quantitative 1 The composition of the slightly yellow glassy product analyzed by H NMR (qNMR) was 61.7% sodium lauroyl / myristoyl alaninate, 23.4% sodium lauroyl / myristoyl taurate, 7.2% fatty acid soap, 4.1% sodium alaninate, 0.7% taurine sodium salt, 1.0% lauroyl / myristoyl methyl ester, and 0.4% methanol.

[0081] Example 2 Synthesis of blends of sodium lauroyl / myristoyl alaninate and sodium N-methyl lauroyl / myristoyl taurate A series of experiments were conducted using a glass reaction vessel. It was equipped with a stirrer with a Teflon blade, a Dean-Stark trap with a condenser, a nitrogen inlet, an addition funnel, and a thermocouple connected to a temperature control device. The reactor was heated using a heating mantle plugged into the temperature control device. The reactor was charged with L-alanine (80.99 g, 0.90 mol), dry sodium N-methyltaurine (2-methyl-aminoethanesulfonic acid sodium salt, 43.80 g, 0.27 mol), and 25 wt% sodium methoxide solution (213.95 g, 0.99 mol). The contents of the reactor were heated to 65-68 °C with stirring under nitrogen. At this point, CE1270 (259.21 g, 1.17 mol)—a product of P&G Chemicals, a methyl laurate / methyl myristate mixture—was added to the reactor through the addition funnel (approximately 50 min) while maintaining good mixing, and the temperature was set to 90°C. The evaporated methanol was collected in a Dean-Stark flask. After reaching 90°C, the reaction temperature was gradually increased to 125°C. The initially two-phase reaction became one-phase during this time, and the reaction was considered complete when the methanol stopped condensing (6.5 h). The molten product was poured from the reactor and allowed to cool to ambient temperature. Quantitative 1 The composition of the clear glassy product analyzed by H NMR (qNMR) was 71.1% sodium lauroyl / myristoyl alaninate, 20.7% sodium N-methyl lauroyl / myristoyl taurate, 5.0% fatty acid soap, 1.2% sodium alaninate, 1.0% lauroyl / myristoyl methyl ester, and 0.2% methanol.

[0082] Example 3 Synthesis of blends of sodium lauroyl / myristoyl alaninate and sodium lauroyl / myristoyl glycinate A series of experiments were conducted using a glass reaction vessel. It was equipped with a stirrer with a Teflon blade, a Dean-Stark trap with a condenser, a nitrogen inlet, an addition funnel, and a thermocouple connected to a temperature control device. The reactor was heated using a heating mantle plugged into the temperature control device. The reactor was charged with L-alanine (89.09 g, 1.00 mol), glycine (26.28 g, 0.35 mol), and 25 wt% sodium methoxide solution (319.98 g, 1.49 mol). The contents of the reactor were heated to 65-68 °C with stirring under nitrogen. At this point, CE1270 (299.05 g, 1.35 mol)—a methyl laurate / methyl myristate mixture from P&G Chemicals—was added to the reactor through the addition funnel (approximately 45 min) while maintaining good mixing, and the temperature was set to 90 °C. The evaporated methanol was collected by the Dean-Stark device. After reaching 90°C, the reaction temperature was gradually increased to 125°C. The initially two-phase reaction became one-phase during this time, and the reaction was considered complete when the methanol stopped condensing (3.25 hours). The molten product was poured from the reactor and allowed to cool to ambient temperature. Quantitative 1 The composition of the clear, pale yellow glassy product analyzed by H NMR (qNMR) was 67.2% sodium lauroyl / myristoyl alaninate, 24.2% sodium lauroyl / myristoyl glycinate, 5.1% fatty acid soap, 2.4% sodium alaninate, 0.1% lauroyl / myristoyl methyl ester, and 1.3% methanol.

[0083] Examples 4 and 5 demonstrate the synthesis / preparation / manufacture of blends of sodium cocoyl alaninate and sodium cocoyl taurate containing >25% by weight taurate surfactant and substantially free of solvent and sodium chloride (NaCl).

[0084] Example 4 Coco fatty acid methyl ester (1284.3 g, 6.0 mol) and sodium methoxide solution (1367.7 g, 6.4 mol) were charged to a reactor under a nitrogen blanket in a horizontal forced mixer equipped with a plow-type agitator, a distillation column, and an inert gas inlet. Solid L-alanine (281.4 g, 3.2 mol) and solid taurine (351.7 g, 2.8 mol) were then added while mixing with the mixer at a Froude number of 0.8 and a temperature of 25-30°C. The temperature of the reaction mixture was gradually increased to 159°C over several hours. o The temperature was increased to 100°C. The alcohol from the base and that formed during the reaction was removed from the mixer by distillation. The reaction was considered complete when no more methanol was collected. The heat was then turned off and the mixer was cooled to about 25-30°C while the shaft-plow component continued to mix the reaction product. 1767.2 g of a white, ground product was discharged from the mixer through the bottom port at ambient temperature. Quantitative analysis of the solids after grinding revealed that 1767.2 g of the white, ground product was obtained. 1 H NMR (qNMR) analysis gave the following composition: 44.0% sodium cocoyl taurate, 33.2% sodium cocoyl alaninate, 5.4% soap, and 6.1% fatty acid methyl esters.

[0085] Example 5 A horizontal forced mixer equipped with a plow-type agitator, a distillation column, and an inert gas inlet was charged with sodium methoxide solution (1362.4 g, 6.4 mol) under a nitrogen blanket. Solid L-alanine (145.2 g, 1.6 mol) was then added at a temperature of 25-30°C while the mixer was mixing at a Froude number of 0.8. After 10 minutes, coco fatty acid methyl ester (1284.3 g, 6.0 mol) and solid taurine (543.2 g, 4.3 mol) were charged to the reactor. The temperature of the reaction mixture was gradually increased to 160°C over several hours. Alcohol from the base and alcohol formed during the reaction were removed from the mixer by distillation. The reaction was considered complete when methanol was no longer collected. The heat was then turned off and the mixer was cooled to approximately 25-30°C while the shaft-plow component continued to mix the reaction product. 1883.9 g of white, ground product was discharged from the mixer through the bottom port at ambient temperature. Quantitative analysis of solids after grinding 1 H NMR (qNMR) analysis gave the following composition: 58.6% sodium cocoyl taurate, 19.4% sodium cocoyl alaninate, 4.9% soap, and 5.7% fatty acid methyl esters.

[0086] (Examples 6 to 11) Examples 6-11 in Table 1 below show ingredient lists for personal care products such as shampoos, body washes, etc.

[0087] [Table 1] 1. A blend of sodium cocoyl alaninate and sodium cocoyl taurate made in accordance with the present disclosure. 2. A blend of sodium cocoyl alaninate and sodium methyl cocoyl taurate made in accordance with the present disclosure. 3. Chemccinate DSLS manufactured by Lubrizol 4. Jordapon CI Prill manufactured by BASF 5. Mackam DAB ULS (Solvay) 6. Amphosol HCA-HP manufactured by Stepan 7. BASF Dehyton AB30 8. Dow UCARE Polymer JR-30M 9. Dow UCARE Polymer LR-30M 10. Dow UCARE Polymer KG-30M 11. Flocare C 106MSS, available from SNF 12. Solvay Jaguar Excel 13. Dow Versene 220 14. Sodium Benzoate, manufactured by Emerald Kalama Chemical 15. Sodium Salicylate manufactured by JQC (Huayin) Pharmaceutical 16. Kathon CG by Dow 17. Citric Acid by ADM

[0088] 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 exclude or otherwise limit. The citation of any document shall not be deemed to be prior art to any present disclosure disclosed or claimed herein, or to teach, suggest, or disclose any such present disclosure, 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.

[0089] While particular embodiments of the present disclosure 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 disclosure. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this disclosure. [1] greater than 70% by weight of an N-acyl alaninate surfactant of formula (I); [ka] A surfactant composition comprising a homogeneous mixture of an N-acyl amino acid surfactant of formula (II), [ka] where R is C 5 ~C 21 is an alkyl substituent, R 1 is H or C 1 ~C 4 represents an alkyl radical, R 2 is H, C 1 ~C 4 Alkyl radical, or C 1 ~C 4 represents hydroxyalkyl, and R 3 is the functional moiety COOM and CH 2 -SO 3 M, wherein M is a cationic group selected from the group consisting of alkali metal salts and hydrogen, and said surfactant composition is substantially free of solvent and NaCl. [2] the alkyl substituent is saturated; the alkyl substituent is unbranched; R is C 7~17 is an alkyl substituent, The surfactant composition according to [1], wherein the surfactant composition is substantially free of polyol solvents and water. [3] The surfactant composition according to [1] or [2], comprising a mixture of a combination of an N-acyl alaninate surfactant of formula (I) and an N-acyl amino acid surfactant of formula (II) in an amount of more than 70% by weight, preferably more than 75% by weight, more preferably more than 85% by weight of the composition. . [4] less than 2% by weight, preferably less than 1% by weight, of an N-acylamino acid dipeptide salt, tripeptide salt, or a combination thereof; The surfactant composition according to any one of [1] to [3], further comprising 0 to 1% by weight of an alkyl alcohol (R'OH). [5] The surfactant composition according to any one of [1] to [4], wherein when the surfactant composition contains at least about 60% by weight of N-acylalaninate, the surfactant composition contains less than about 5% by weight, or more preferably less than about 3% by weight, of fatty acid methyl ester. [6] The surfactant composition according to any one of [1] to [4], wherein when the surfactant composition contains about 35% by weight or less of N-acylalaninate, the surfactant composition contains less than about 15% by weight, preferably less than about 10% by weight, or more preferably less than 5% by weight of fatty acid methyl ester. [7] The surfactant composition according to any one of [1] to [6], wherein the surfactant composition is in the form of a solid or a solution, and preferably the surfactant composition is in the form of a solid selected from the group consisting of powders, granules, flakes, noodles, needles, extrudates, ribbons, beads, and pellets, and combinations thereof. [8] The surfactant composition of [1], wherein the surfactant composition is in a form selected from the group consisting of a granular detergent, a bar detergent, a liquid laundry detergent, a gel detergent, a single-phase or multi-phase unit dose detergent, a single-phase or multi-phase or multi-compartment water-soluble pouch detergent, a liquid hand dish composition, a laundry pretreatment product, a surfactant contained on or in a porous substrate or a nonwoven sheet, an automatic dishwashing detergent, a hard surface cleaner, a fabric softener composition, a personal care composition, and mixtures thereof. [9] A process for the preparation of a blend of N-acyl alaninate surfactant and N-acyl amino acid surfactant, comprising: (a) an alanine amino acid; and (b) another amino acid, an anhydrous alkali salt of said other amino acid, or both; anhydrous base, and in combination with a fatty alkyl ester of formula (V), [ka] (Wherein R is C 5 ~C 21 alkyl substituents, and R' is C 1 or more alkyl substituents, preferably methyl); an alanine amino acid salt of formula (III)

change

change

[10] The combining step preparing a suspension of the alanine amino acid salt of formula (III) and the other amino acid salt of formula (IV) by adding the anhydrous base to the alanine amino acid and the other amino acid; contacting the suspension with the fatty alkyl ester of formula (V) to form the mixture; 9. The method of claim 9, wherein the mixture comprises less than about 25% by weight of the mixture of taurine, sodium N-methyl taurine, or both.

[11] the combining step comprises combining the anhydrous base and the fatty alkyl ester of formula (V) to form a premix; and then adding (a) the alanine amino acid and (b) the other amino acid, the anhydrous alkali salt of the other amino acid, or both, to the premix to form the mixture; 10. The method of claim 10, wherein the mixture comprises at least about 25% by weight of the mixture of taurine, sodium N-methyl taurine, or both.

[12] Increasing the temperature of the mixture includes increasing the temperature of the mixture to about 65°C to about 180°C, or preferably about 90°C to about 150°C; The method according to any one of [9] to

[11] , wherein rendering the reaction mixture substantially transparent to form the blend comprises rendering the reaction mixture a single phase, and preferably the method is carried out under an inert gas headspace at atmospheric pressure.

[13] The alanine amino acid comprises a naturally occurring α-amino acid, an unnatural amino acid (opposite "D" stereochemistry), or a racemic mixture, preferably wherein (b) the other amino acid, the anhydrous alkaline salt of the other amino acid, or both, is selected from the group consisting of sarcosine, glycine, serine, proline, taurine, and N-methyltaurine; The anhydrous base is C in methanol solution 1 ~C 4 The method according to any one of [9] to

[12] , comprising an alkoxide, preferably sodium or potassium methoxide, or a combination thereof.

[14] The mixture (a) the alanine amino acid and (b) about 1.00 to about 1.50 moles, preferably about 1.02 to about 1.20 moles, and more preferably about 1.05 to about 1.10 moles of the anhydrous base per mole of the other amino acid, the anhydrous alkali salt of the other amino acid, or a combination of both; The method according to any one of [9] to

[13] , comprising: (a) the alanine amino acid; and (b) about 0.90 to about 1.50 moles, preferably about 0.95 to about 1.20 moles, or more preferably about 1.00 to about 1.05 moles of the fatty alkyl ester per mole of the other amino acid, the anhydrous alkali salt of the other amino acid, or a combination of both.

[15] The method of any of [9] to

[14] , further comprising combining the blend with water when the blend comprises more than 70% by weight, preferably more than 75% by weight, more preferably more than 85% by weight of the blend of the N-acyl alaninate surfactant and the N-acyl amino acid surfactant in combination.

Claims

1. A surfactant composition comprising greater than 70% by weight of a homogeneous mixture, said homogeneous mixture comprising an N-acyl alaninate surfactant of formula (I) and 【Chemical 1】 and an N-acylaminosulfonic acid surfactant of formula (II), 【Chemistry 2】 where R is a saturated, unbranched C ７ ~C １７ is an alkyl substituent, R １ is H or C １ ~C ４ represents an alkyl radical, R ２ is H, C １ ~C ４ Alkyl radical, or C １ ~C ４ represents hydroxyalkyl, R ３ is the functional part CH ２ -SO ３ M, where M is a cationic group selected from the group consisting of alkali metal salts and hydrogen; 1. A surfactant composition, wherein the surfactant composition is substantially free of polyol solvents, water, and NaCl.

2. 10. The surfactant composition of claim 1, comprising greater than 75% by weight of said homogeneous mixture of said surfactant composition.

3. less than 2% by weight of the surfactant composition of an N-acylamino acid dipeptide salt, tripeptide salt, or combination thereof; 10. The surfactant composition of claim 1, further comprising: an alkyl alcohol (R'OH) in an amount of 0-1% by weight of the surfactant composition.

4. 2. The surfactant composition of claim 1, wherein said surfactant composition comprises at least 60% by weight of said surfactant composition of an N-acylalaninate surfactant, and may comprise less than 5% by weight of said surfactant composition of a fatty acid methyl ester.

5. 2. The surfactant composition of claim 1, wherein said surfactant composition comprises less than 15% by weight of said surfactant composition of a fatty acid methyl ester when said surfactant composition comprises less than 35% by weight of said surfactant composition of an N-acylalaninate surfactant.

6. The surfactant composition of claim 1 , wherein the surfactant composition is a solid or a solution.

7. 10. The surfactant composition of claim 1, wherein the surfactant composition is in a form selected from the group consisting of a granular detergent, a bar detergent, a liquid laundry detergent, a gel detergent, a single-phase or multi-phase unit dose detergent, a single-phase or multi-phase or multi-compartment water-soluble pouched detergent, a liquid hand dish composition, a laundry pre-treatment product, a surfactant contained on or in a porous substrate or nonwoven sheet, an automatic dishwashing detergent, a hard surface cleaner, a fabric softener composition, a personal care composition, and mixtures thereof.

8. 10. A process for the preparation of the surfactant composition of claim 1, comprising: (a) an alanine amino acid; and (b) an aminosulfonic acid, an anhydrous alkali salt of said aminosulfonic acid, or both; anhydrous base, and in combination with a fatty alkyl ester of formula (V), 【Chemistry 3】 where R is a saturated, unbranched C ７ ~C １７ alkyl substituents, R' is selected from C １ or higher alkyl substituents), an alanine amino acid salt of formula (III) 【Chemistry 4】 wherein M is a cationic group selected from alkali metal salts. an aminosulfonic acid salt of formula (IV) 【Chemistry 5】 (In the formula, R １ is H or C １ ~C ４ represents an alkyl radical, R ２ is H, C １ ~C ４ Alkyl radical, or C １ ~C ４ represents hydroxyalkyl, R ３ is the functional part CH ２ -SO ３ M, where M is a cationic group selected from alkali metal salts; increasing the temperature of the mixture to 180°C or less to form a reaction mixture; continuously removing alkyl alcohol from the reaction mixture; and allowing the reaction mixture to substantially clarify to form a homogeneous mixture of N-acyl alaninate surfactant and N-acyl amino sulfonic acid surfactant.

9. The combining step comprises: preparing a suspension of the alanine amino acid salt of formula (III) and the aminosulfonic acid salt of formula (IV) by adding the anhydrous base to the alanine amino acid and the aminosulfonic acid; contacting the suspension with the fatty alkyl ester of formula (V) to form the mixture; 9. The method of claim 8, wherein the mixture may comprise less than 25% by weight of the mixture of taurine, sodium N-methyl taurine, or both.

10. the combining step comprises combining the anhydrous base with the fatty alkyl ester of formula (V) to form a premix; and then adding (a) the alanine amino acid and (b) the aminosulfonic acid, the anhydrous alkali salt of the aminosulfonic acid, or both to the premix to form the mixture; 9. The method of claim 8, wherein the mixture comprises at least 25% taurine, sodium N-methyl taurine, or both, by weight of the mixture.

11. increasing the temperature of the mixture includes increasing the temperature of the mixture to between 65°C and 180°C; 10. The method of claim 8, wherein allowing the reaction mixture to substantially clarify and form the homogeneous mixture comprises allowing the reaction mixture to become a single phase.

12. the alanine amino acid comprises a naturally occurring α-amino acid, an unnatural amino acid (opposite "D" stereochemistry), or a racemic mixture; The anhydrous base is C in methanol solution １ ~C ４ 9. The method of claim 8, comprising: a hydroxybenzoate; an alkoxide; or a combination thereof.

13. (b) the aminosulfonic acid, the anhydrous alkaline salt of the aminosulfonic acid, or both are selected from the group consisting of taurine and N-methyltaurine; 9. The method of claim 8, wherein the anhydrous base comprises sodium methoxide, potassium methoxide, or a combination thereof in a methanol solution.

14. The mixture (a) the alanine amino acid and (b) 1.00 to 1.50 moles of the anhydrous base per mole of the aminosulfonic acid, the anhydrous alkali salt of the aminosulfonic acid, or a combination of both; 9. The method of claim 8, comprising: (a) the alanine amino acid; and (b) 0.90 to 1.50 moles of the fatty alkyl ester per mole of the aminosulfonic acid, the anhydrous alkali salt of the aminosulfonic acid, or a combination of both.

15. 10. The method of claim 8, further comprising combining the surfactant composition with water.

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