Biodegradable surfactant with introduced functional groups and method of use thereof

Abstract

This invention provides a novel bio-based surfactant derivative with improved pH stability, and also offers its use in various consumer products. Furthermore, it provides a method for producing such a surfactant derivative.

Description

[Technical Field]

[0001] (Cross-reference of related applications) This application claims priority to U.S. Provisional Patent Application No. 63 / 487,866, filed on 1 March 2023, which is incorporated herein by reference in its entirety. [Background technology]

[0002] Surfactants are amphiphilic molecules with surface activity, and their applications are expected in almost every industrial sector. Therefore, the surfactant market, which currently comprises thousands of different surfactant molecules, is rapidly expanding. Approximately 60% of surfactants are used as compounds in detergents and personal care products. Other applications include, for example, cleaning products, pharmaceuticals and supplements, oil and gas recovery, bioremediation, agriculture, cosmetics, coatings and paints, textile manufacturing, food production and processing, and construction.

[0003] Synthetic surfactants are advantageous because they are easy to manufacture and can be designed to perform desired functions based on their molecular structure. As a result, synthetic surfactants have been overused and overproduced for decades. However, with increasing awareness from consumers and regulators, the drawbacks of synthetic surfactants are beginning to surface. These include a narrow activity range, known or potential toxicity to humans and animals, persistence in the environment such as aquatic environments, soil and groundwater, impacts on climate change due to production and use, and poor compatibility with other chemicals.

[0004] Therefore, there is a growing demand among consumers for cleaning and other household and personal care products that are non-toxic, non-irritating to the skin and / or eyes, and have a reduced environmental impact. However, even with these improved safety and sustainability features, it is expected that these products will perform at the same level as conventional products in many properties, such as cleaning, disinfecting, chelating, emulsifying, foaming, and wetting properties, and that they will also be stable across a wide pH range. Because natural and sustainable materials that meet these needs are limited, there remain challenges in formulating safe and environmentally friendly consumer products.

[0005] Therefore, there is a need for improved "green" surfactant compounds that maintain effectiveness and stability in various usage environments while minimizing the potential for adverse effects on human and animal health and environmental integrity. [Overview of the project] [Means for solving the problem]

[0006] This application provides materials and methods for producing functionally modified surfactant derivative compounds, including bio-based surfactants and biosurfactants, as well as functionally modified derivative surfactant compounds having improved properties. More specifically, the present invention provides surfactant compounds derived from amino acids, fatty acids, and / or biosurfactants, which have pH stability over a wide pH range, for example, pH 2 to 12. Methods for producing such compounds, formulation methods, and methods for using such compounds are also provided. The methods and compositions of the present invention are advantageous in that they can mitigate the environmental impacts that generally arise from the production and use of surfactants.

[0007] Certain compounds containing an ester moiety, such as lauroyl arginine ethyl ester (LAE), are unstable at pH 7 or higher, potentially leading to two undesirable reactions: hydrolysis of the ester to generate zwitterionic species and / or intramolecular cyclization (Figure 1). Therefore, in environments where neutral to basic pH levels are preferred, these undesirable reactions reduce the effectiveness of ester-containing compounds. Accordingly, the present invention provides a solution to overcome this problem by offering stable surfactant derivative compounds suitable for applications such as detergents, disinfectants, emulsifiers, emollients, preservatives, and conditioners (Figures 2-3B).

[0008] In certain embodiments, the derivatized surfactant compound is a functionally grouped amino alcohol that can be designed, for example, to suit desired functionality, stability, biodegradability, and / or compatibility with other substances. The surfactant derivative "XYZ" is preferably an amino acid alcohol having the structure described in general formula (1).

[0009] [ka]

[0010] In the formula, X is a fatty acid amide derived from a fatty acid or a biosurfactant containing a fatty acid portion, Y contains one or more functional groups derived from amino acids, and Z 1 and Z 2 Each of these is independently a hydrogen atom, an alkyl group (e.g., a methyl group), or another substituent, such as a phenyl group or a benzyl group.

[0011] More specifically, the X group is preferably derived from a substrate containing an acyl group whose fatty acid carbon chain length ranges from C2 to C22. For example, X may be derived from lauric acid, an acyl halide (e.g., lauroyl chloride), or a biosurfactant (e.g., a glycolipid with a carbon chain length of C8 to C22).

[0012] Furthermore, the Y group preferably contains one or more functional groups derived from amino acids, and these functional groups can be selected based on the desired functionality of the surfactant compound.

[0013] Furthermore, the pH stability of the compound can be improved by using a reducing agent to reduce any ester group to, for example, a primary alcohol, secondary alcohol, or tertiary alcohol.

[0014] In certain embodiments, the derivatized surfactant compound is an aliphatic amino alcohol surfactant, an amide amino alcohol surfactant, an aromatic amino alcohol surfactant, a cationic amino alcohol surfactant (Figure 4), an alcoholic diol amino surfactant, or a sulfonic acid amino alcohol surfactant.

[0015] The present invention further provides a method for producing a derivatized surfactant compound (XYZ), comprising the step of coupling a substrate (X') containing a fatty acid or a biosurfactant with an amide (Y') containing one or more amino acid-derived functional groups (Y) to obtain a surfactant (XY) into which amino acid functional groups have been introduced. In order to produce XYZ, a reagent Z' is used to reduce any desired ester group to a primary alcohol, secondary alcohol, or tertiary alcohol before, during, or after the coupling to obtain XY. Figures 5 to 10B.

[0016] The present invention provides advantageous novel compounds, such as those described in the drawings and the present specification, as well as formulations containing these novel compounds and methods of using them. The derivative compounds produced and / or derivatized according to the present invention are advantageous in that they can avoid the adverse effects caused by reactions occurring in a neutral to basic pH environment, namely, destabilization and loss of effectiveness due to ester hydrolysis and / or intramolecular cyclization. Furthermore, such compounds can be used as a more "green" active ingredient in place of compounds such as synthetic surfactants in environments such as the home, industry, office-retail sales, and further in personal care and healthcare.

Brief Description of the Drawings

[0017] [Figure 1] A reaction scheme is shown in which zwitterionic species are produced by hydrolysis from an amine-derivatized amino acid compound containing an ester moiety or are converted to a lactam at pH 7 or higher. [Figure 2] A reaction scheme in one embodiment of the present invention is shown in which any amino acid or amino acid ester is usually synthetically stabilized by conversion to an amino alcohol. [Figure 3A] In one embodiment of the present invention, the pH stability of lauryl arginine ethyl ester (LRE) and a cationic amino alcohol surfactant (LRO) at pH 7 is compared under different incubation conditions. Oven = 45°C, relative humidity 50%; atmosphere = room temperature. [Figure 3B] In one embodiment of the present invention, the pH stability of lauryl arginine ethyl ester (LRE) and a cationic amino alcohol surfactant (LRO) at pH 10 is compared under different incubation conditions. Oven = 45°C, relative humidity 50%; atmosphere = room temperature. [Figure 4] An exemplary cationic amino alcohol surfactant derivative is shown in which the primary amine is bonded to R1 = lauryl carbon chain (1) or a linear sophorolipid backbone (2-3). R2 = a functional group derived from an amino acid. [Figure 5]The synthesis reaction scheme for amino alcohols is shown, using arginine synthesis as an example. [Figure 6] This shows the reaction scheme for the synthesis of laurylarginine amide derivatives via amide coupling. [Figure 7] This shows the reaction scheme for the synthesis of lauryl alginol amide derivatives via amide coupling. [Figure 8] The reaction scheme in one embodiment of the present invention, in which linear sophorolipids are obtained by hydrolysis of diacetylated lactone-type sophorolipids, is shown. [Figure 9] This shows a reaction scheme in one embodiment of the present invention, in which a long-chain amide containing a functional group derived from a cationic amino acid is obtained by amide coupling of a linear SLP substrate. [Figure 10A] The reaction scheme in one embodiment of the present invention, in which an acid is obtained by oxidative cleavage of a linear SLP substrate, is shown. [Figure 10B] The reaction scheme in one embodiment of the present invention is shown, in which a short-chain amide containing a functional group derived from a cationic amino acid is obtained by amide coupling of a cleaved acid. [Modes for carrying out the invention]

[0018] Certain surfactant molecules, such as LAE (and LRE), contain a problematic ester moiety and are therefore unsuitable for environments with a pH of 7 or higher. At this pH range, undesirable reactions occur in the ester moiety, resulting in a loss of effectiveness (e.g., effectiveness as an active ingredient with disinfectant properties). See, for example, Figure 1. The present invention provides a solution to avoid such pH-dependent instability by removing this ester moiety, which is advantageous in that it increases the predictability of the pH applicability of various surfactants containing amino acid residues and broadens the pH range in which they can be used.

[0019] Selected definition In this specification, the term "alkyl" means a linear or branched hydrocarbon group. Suitable alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, and octadecyl. The term alkyl may be prefixed with a specific number of carbon atoms to indicate the number of carbon atoms in the alkyl group or a range of assumed carbon atoms, such as C1-C10 alkyl, C1-C20 alkyl, C10-C20 alkyl, etc. For example, C1-C3 alkyl means methyl, ethyl, propyl, and isopropyl.

[0020] In this specification, a “green” compound or material means a compound or material that is at least 95% derived from natural, biological, and / or renewable raw materials such as plants, animals, minerals, and / or microorganisms, and is also biodegradable. Furthermore, in some embodiments, the “green” compound or material has minimal toxicity to humans, and its LD50 may exceed 5,000 mg / kg. “Green” products preferably do not contain any non-plant-derived ethoxylated surfactants, linear alkylbenzene sulfons (LAS), ether sulfate surfactants, or nonylphenol ethoxylates (NPE). In certain preferred embodiments, the derivatized surfactant molecules described herein are “green” compounds with minimal toxicity to users.

[0021] In this specification, “biofilm” means a complex collection of microorganisms such as bacteria, yeasts, and fungi, in which each cell is attached to one another and / or to the surface via an extracellular matrix. Cells within a biofilm are physiologically different from the planktonic cells of the same organism, which may float or swim in a liquid culture medium.

[0022] In this specification, "derivative" is a substance produced by a chemical reaction from a given substance, for example, a substance produced by the substitution of an atom or group of atoms in the parent substance with another atom or group of atoms.

[0023] In this specification, “preventing” a situation or event means avoiding, delaying, preventing, or minimizing the occurrence of specific signs or symptoms of the situation or event. “Prevention” may be achieved absolutely or completely, but is not necessarily required, and the situation or event may still develop further. “Prevention” includes reducing the severity of the occurrence of the situation or event and / or deterring the situation or event from developing into a more serious situation.

[0024] In this specification, the "backbone" of a molecule refers to the central structure of the molecule, and the functional groups are bonded to this central structure.

[0025] In this specification, “surfactant” means a substance or compound that, when dissolved in water or an aqueous solution, reduces surface tension, or a substance or compound that reduces interfacial tension between two liquids or between a liquid and a solid. Therefore, the term “surfactant” includes cationic, anionic, nonionic, zwitterionic, amphoteric surfactants and / or combinations thereof. “Biosurfactant” means a surfactant produced by living cells and / or a surfactant manufactured using naturally derived raw materials.

[0026] The properties of surfactant molecules can be measured by the hydrophilic-lipophilic balance (HLB). HLB indicates the balance between the size and strength of the hydrophilic and lipophilic portions of a surfactant molecule. For example, a specific HLB value is required to form a stable emulsion. In water-in-oil and oil-in-water emulsions, the polar portion of the surfactant molecule faces the water side and the nonpolar portion faces the oil side, thus reducing the interfacial tension between the oil and water phases.

[0027] The HLB value ranges from 0 to approximately 20. A low HLB (e.g., 10 or less) indicates high oil solubility and suitability for water-in-oil emulsions, while a high HLB (e.g., 10 or more) indicates high water solubility and suitability for oil-in-water emulsions. Furthermore, other properties such as foaming, wetting, cleaning properties, and solubility are also affected by the HLB value.

[0028] In this specification, "base surfactant" means a surfactant or amphiphilic molecule that is arranged relatively regularly in a state perpendicular to the interface and has a strong tendency to adsorb to the interface.

[0029] In this specification, the term “syndetic” (meaning to link or bond together like when mixing water and oil) refers to a relatively weak amphiphilic substance that exhibits significant adsorption at the oil-water interface only when an adsorbed layer of a base surfactant or mixture of base surfactants is already present at the interface (“hydrophilic syndetic” from the aqueous phase, and “hydrophobic syndetic” from the oil phase). The adsorption of syndetic to the oil-water interface is thought to influence the spacing and / or order of the adsorbed ordinary surfactants in a manner that is highly beneficial for the generation of very weak oil-water interfacial tension. This promotes the dissolution of oil and / or the removal of oil from solid materials and / or surfaces.

[0030] In this specification, "isolated" or "purified" nucleic acid molecules, polynucleotides, polypeptides, proteins, or organic compounds (e.g., small molecules) are described as being substantially free of other compounds (e.g., intracellular substances) that would be associated with them in their natural state. Purified or isolated polynucleotides (ribonucleic acid (RNA) or deoxyribonucleic acid (DNA)) are described as being free of genes or sequences that would be adjacent to them in their natural state. Purified or isolated polypeptides are described as being free of other molecules or amino acids that would be adjacent to them in their natural state. An "isolated" strain is described as a strain that has been isolated from its natural environment. Therefore, an isolated strain may exist, for example, as a biologically pure culture or as spores (or other forms of the strain).

[0031] In certain embodiments, the purified compound contains at least 60% by weight of the compound of interest. Preferably, the preparation contains at least 75% by weight, more preferably at least 90% by weight, and most preferably at least 99% by weight of the compound of interest. For example, the purified compound is one in which the desired compound is present at least 90% (w / w), 91% (w / w), 92% (w / w), 93% (w / w), 94% (w / w), 95% (w / w), 98% (w / w), 99% (w / w), or 100% (w / w) on a weight basis. Purity is measured by any suitable standard method, such as column chromatography, thin-layer chromatography, or high-performance liquid chromatography (HPLC).

[0032] The ranges described herein are understood to be abbreviated expressions representing all values ​​within that range. For example, the range 1 to 20 is understood to encompass any number, combination of numbers, or subrange selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20, and also encompass all decimal values ​​that exist between these integers, such as 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, and 1.9. In the case of subranges, specifically, "nested subranges" extending from each endpoint of the described range are assumed. For example, nested subranges of an exemplary range of 1 to 50 could include 1 to 10, 1 to 20, 1 to 30, and 1 to 40 in one direction, and 50 to 40, 50 to 30, 50 to 20, and 50 to 10 in the other direction.

[0033] In this specification, “decrease” means a negative change, and “increase” means a positive change. The range of change here is at least 0.001%, 0.01%, 0.1%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 99%, or 100%, and includes all values ​​that lie between these values.

[0034] The transitional phrase "including" is synonymous with "containing" or "containing," and is a comprehensive or open-ended expression that does not exclude other elements or steps within the method that are not described in the claim. In contrast, the transitional phrase "consisting of" excludes elements, steps, or components that are not expressed in the claim. The transitional phrase "essentially consisting of" limits the scope of the claim to the expressed materials or steps and "that do not substantially affect the basic and novel features of the invention described in the claim." When the term "including" is used, other embodiments that "consist of" or "essentially consist of" the components described in the claim are also assumed.

[0035] In this specification, the term “or” is understood to be inclusive unless otherwise specified or as is evident from the context. In this specification, the terms “a,” “an,” and “the” are understood to be singular or plural unless otherwise specified or as is evident from the context.

[0036] In this specification, the term "about" is understood to mean within the normal range of acceptance in the art, e.g., within two standard deviations from the mean, unless otherwise specified or made clear from the context. "About" may be understood to mean within 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.1%, 0.05%, or 0.01% of the stated value.

[0037] Where a list of chemical groups is provided in the definition of a variable in this specification, it is assumed that the variable is defined as any one of the groups listed or any combination thereof. Where embodiments relating to a variable or aspect are described in this specification, it is assumed that the embodiments are described as any standalone embodiment or in combination with any other embodiment or part thereof.

[0038] All references cited herein are incorporated herein by reference.

[0039] Derivatized surfactant molecules This application provides materials and methods for producing derivatized surfactants, including bio-based surfactants and biosurfactants, as well as derivatized surfactants having improved properties. More specifically, the present invention provides surfactant compounds derived from amino acids, fatty acids, and / or biosurfactants, which have pH stability over a wide pH range, for example, pH 2 to 12. Methods for producing such compounds, formulation methods, and methods for using them are also provided. Such stable derivatized surfactant compounds are advantageous in that they are suitable for applications such as detergents, disinfectants, emulsifiers, emollients, preservatives, and conditioners.

[0040] In certain embodiments, the derivatized surfactant compound is, for example, an amino alcohol into which a functional group has been introduced, which can be designed to suit desired functionality, stability, biodegradability, and / or compatibility with other substances. The surfactant derivative "XYZ" is preferably an amino acid-derived alcohol having the structure described in general formula (1).

[0041] [ka]

[0042] In the formula, X is a fatty acid amide derived from a fatty acid or a biosurfactant containing a fatty acid portion, Y contains one or more functional groups derived from amino acids, and Z 1 and Z 2 Each of these is independently a hydrogen atom, an alkyl group (e.g., a methyl group), or another substituent, such as a phenyl group or a benzyl group. In certain embodiments, Z 1 and Z 2 The hydrogen atom improves the atomic economy. On the other hand, using an alkyl group increases the carbon content and decreases the atomic economy, but it can lower the HLB of the molecule if desired.

[0043] The present invention encompasses all compounds represented by general formula (1), including their hydrates, geometric isomers and optical isomers, and polymorphs.

[0044] In certain embodiments, the biodegradability of the derivatized surfactant compound can be improved by having X derived from a biosurfactant. Examples of biosurfactants include glycolipids such as sophorolipids (SLP), rhamnolipids (RLP), cellobiose lipids, trehalose lipids and / or mannosylerythritol lipids (MEL); lipopeptides such as surfactant, itulin, fengisin, altrofactin, amphisin, viscosin, lichenisin, penibacterin, polymyxin and / or batasin; or other types of amphiphilic molecules, such as fatty acids, saponins, cardiolipin, pullulan, emulsan, lipomanan, alasan and / or liposan. In some embodiments, the biosurfactant is obtained by fermentation carried out by a biosurfactant-producing organism and / or derived from a natural substrate material. In preferred embodiments, the biosurfactant is a sophorolipid (SLP).

[0045] X can be selected based on the desired properties as a surfactant. For example, the longer the carbon chain, the lower the critical micelle concentration (CMC) of the molecule can be.

[0046] In certain embodiments, the X group is preferably derived from an acyl group of a fatty acid with various carbon chain lengths, for example, a substrate having an acyl group with a carbon chain length of C2-C22. For example, X may be derived from an acyl halide. In some embodiments, X is

[0047] [ka] [ka] or [ka] That is the case.

[0048] Furthermore, the Y group preferably contains one or more functional groups derived from amino acids, and these functional groups can be selected based on the desired functionality of the XYZ compound. The amino acid-derived functional groups may be derived from any amino acid, and examples of such amino acids include alanine, arginine, homoarginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, selenocysteine, and any polymers or stereoisomers thereof.

[0049] Furthermore, the pH stability of the compound can be improved by reducing any desired ester group to a primary, secondary, or tertiary alcohol using a reducing agent, for example, by introducing a hydride or alkyl anion.

[0050] [Table 1]

[0051] Aliphatic amino alcohol surfactants In certain embodiments, the derivatized surfactant compound is an aliphatic amino alcohol surfactant particularly useful as an emulsifier, emollient, and / or wetting agent. Furthermore, the aliphatic amino alcohol surfactant has a primary or tertiary alcohol, which can be further increased in molecular weight by introducing an alkoxyl group.

[0052] Aliphatic amino alcohol surfactants XYZ can be prepared by optionally combining the X' and Z' reagents from Table 1 with the Y' amide reagent containing a functional group derived from an aliphatic amino acid. For example, in some embodiments, Y' includes alanine, glycine, methionine, valine, leucine, isoleucine, or proline. In certain embodiments, Y' includes an aliphatic amino acid alkyl ester selected from alanine ethyl ester, glycine ethyl ester, methionine ethyl ester, valine ethyl ester, leucine ethyl ester, isoleucine ethyl ester, and proline ethyl ester.

[0053] If Y' contains methionine ethyl ester, the resulting thioether can be further oxidized to produce a derivatized surfactant compound containing a sulfone Y group. This compound is particularly useful as an emulsifier, emollient, wetting agent, surfactant, and / or chelating agent.

[0054] Amidoamino alcohol surfactant In certain embodiments, the derivatized surfactant compounds are amide-amino alcohol surfactants that are particularly useful as emulsifiers, emollients, wetting agents, surfactants, and / or chelating agents. Amido-amino alcohol surfactants can be prepared by optionally combining reagents X' and Z' of Table 1 with reagent Y' containing a glutamine functional group and / or an asparagine functional group. All of these functional groups contain an amide group in their side chain. In certain embodiments, Y' includes an amide-amino acid alkyl ester selected from glutamine ethyl ester and asparagine ethyl ester.

[0055] Aromatic amino alcohol surfactants In certain embodiments, the derivatized surfactant compound is an aromatic amino alcohol surfactant, particularly useful as an emulsifier, emollient, wetting agent, and / or surfactant. Furthermore, the aromatic amino alcohol surfactant has a primary or tertiary alcohol, which can be further increased in molecular weight by introducing an alkoxyl group.

[0056] Aromatic amino alcohol surfactants can be prepared by optionally combining reagents X' and Z' from Table 1 with an amide reagent Y' containing an aromatic functional group. For example, in some embodiments, Y' may contain phenylalanine, tyrosine, or tryptophan. In certain embodiments, Y' contains an aromatic amino acid alkyl ester selected from phenylalanine ethyl ester, tyrosine ethyl ester, and tryptophan ethyl ester.

[0057] Cationic amino alcohol surfactant In certain embodiments, the derivatized surfactant compound is a cationic amino alcohol surfactant particularly useful as an antimicrobial agent, preservative, and / or conditioner for hair / textile products. Furthermore, the cationic amino alcohol surfactant may have a primary or tertiary alcohol to which an alkoxyl group can be introduced to increase the molecular weight.

[0058] Cationic amino alcohol surfactants can be prepared by optionally combining reagents X' and Z' from Table 1 with a Y' amide reagent containing a functional group derived from a cationic amino acid. For example, in some embodiments, Y' may include lysine, arginine, homoarginine, or histidine. In certain embodiments, Y' includes a cationic amino acid alkyl ester selected from lysine ethyl ester, arginine ethyl ester, homoarginine ethyl ester, and histidine ethyl ester.

[0059] In certain embodiments, the cationic surfactant derivative is an amino acid alcohol having the structure described in general formula (2).

[0060] [ka]

[0061] In the formula, R1 is [ka] [ka] or [ka] And, R2 is [ka] [ka] or [ka] And, R3 is H, Me, Et, MePh, Bu, sec-Bu, or t-Bu.

[0062] In certain embodiments, the cationic surfactant derivative has the structure described in general formula (3).

[0063] [ka]

[0064] In the formula, R1 is [ka] or [ka] And, R2 is [ka] [ka] or [ka] That is the case.

[0065] In some embodiments, R1 in general formula (2) and / or (3) is an aliphatic acyl group derived from a C2-C22 acyl halide (or acid halide). Examples of acyl halides include, but are not limited to, lauroyl halides, octanoyl halides, decanoyl halides, dodecanoyl halides, myristiroyl halides, palmitoyl halides, and behenoyl halides. Here, halide is a fluoride, chloride, bromide, or iodide. In preferred embodiments, the acyl halide is an acyl chloride.

[0066] In some embodiments, R1 in general formula (2) and / or (3) is the acyl moiety of a biosurfactant, preferably a glycolipid backbone.

[0067] In a particular exemplary embodiment, the compound of the present invention has the following structure:

[0068] [ka] [ka] or [ka] Take one of them.

[0069] Here, structure (a) is laurylarginineamide, structure (b) is laurylargininol alcohol, and structure (c) is linear sophorolipid argininolamide.

[0070] Diolamino alcohol surfactant In certain embodiments, the derivatized surfactant compound is an alcoholic diolamino surfactant, particularly useful as an emulsifier, emollient, humectant, and / or surfactant. Furthermore, the alcoholic diolamino surfactant has a primary alcohol and / or tertiary alcohol, to which an alkoxyl group can be further introduced to increase the molecular weight. Unlike other surfactants described herein, the alcoholic diolamino surfactant can have an alkoxyl group introduced at two different positions: as an alcohol in the backbone and as an alcohol in the side chain.

[0071] Alcoholic diolamino surfactants can be prepared by optionally combining reagents X' and Z' from Table 1 with an amide reagent Y' containing a hydroxyl amino acid functional group. For example, in some embodiments, Y' may contain tyrosine, threonine, or serine. In certain embodiments, Y' contains a hydroxyl amino acid alkyl ester selected from tyrosine ethyl ester, threonine ethyl ester, and serine ethyl ester.

[0072] In some embodiments, the Y' reagent contains an anionic amino acid such as taurine, aspartate, or glutamate. In certain embodiments, Y' contains diethyl aspartate and / or diethyl glutamate. In some embodiments, if Y' contains diethyl aspartate or diethyl glutamate, the resulting side-chain carbonyl is also reduced by treatment with Z'.

[0073] Sulfonic acid amino alcohol surfactant In certain embodiments, the derivatized surfactant compound is a sulfonic acid amino alcohol surfactant, particularly useful as an emulsifier, emollient, wetting agent, and / or chelating agent. Furthermore, the sulfonic acid amino alcohol surfactant may have a primary or tertiary alcohol, to which an alkoxyl group can be introduced to increase the molecular weight.

[0074] Sulfonic acid amino alcohol surfactants can be prepared by optionally combining reagents X' and Z' from Table 1 with an amide reagent Y' containing a sulfur-containing amino acid functional group. For example, in some embodiments, Y' comprises cysteine ​​or disysteine. In certain embodiments, Y' comprises an amino acid alkyl ester selected from cysteine ​​ethyl ester and disysteine ​​ethyl ester.

[0075] If Y' contains a cysteine ​​ethyl ester, the resulting thiol group can be further oxidized to produce a derivatized surfactant compound containing a sulfonic acid Y group. This surfactant compound is particularly useful as an emulsifier, emollient, wetting agent, surfactant, chelating agent, and / or foaming agent. If Y' contains a disysteine ​​ethyl ester, a similar chemical reaction can be applied to the resulting disulfide. Specifically, the disulfide is either reduced to a thiol first, or the disulfide is directly oxidized to a sulfonic acid.

[0076] Production of derivatized surfactant compounds The present invention further provides a method for producing a derivatized surfactant compound (XYZ) that is stable at pH 2 to 12. This method generally involves coupling a substrate (X') containing a fatty acid or a biosurfactant with an amide (Y') containing one or more amino acid-derived functional groups (Y) to obtain a surfactant (XY) into which amino acid functional groups have been introduced.

[0077] In certain embodiments, X' is an acyl halide, such as lauroyl chloride, octanoyl chloride, decanoyl chloride, dodecanoyl chloride, myristiroyl chloride, palmitoyl chloride, or behenoyl chloride.

[0078] In certain embodiments, X' is a sophorolipid (SLP) biosurfactant. The SLP is preferably a linear SLP molecule. In some embodiments, the linear SLP has a C18 carboxylic acid terminus containing one unsaturated bond (long-chain SLP). In some embodiments, the method includes the steps of obtaining a carboxylic acid terminus cleaved at position 9 by utilizing oxidative cleavage, and obtaining a short-chain SLP amide by introducing an amide containing one or more amino acid functional groups to the cleaved carboxylic acid terminus.

[0079] In certain embodiments, Y' comprises one or more of the following: amino alcohol, alanine ethyl ester, glycine ethyl ester, methionine ethyl ester, valine ethyl ester, leucine ethyl ester, isoleucine ethyl ester, proline ethyl ester, glutamine ethyl ester, asparagine ethyl ester, phenylalanine ethyl ester, tryptophan ethyl ester, lysine ethyl ester, arginine ethyl ester, homoarginine ethyl ester, histidine ethyl ester, tyrosine ethyl ester, threonine ethyl ester, serine ethyl ester, taurine ethyl ester, aspartate diethyl, glutamate diethyl, cysteine ​​ethyl ester and / or disysteine ​​ethyl ester.

[0080] In certain embodiments, X' is coupled with an amide (Y') containing an amino acid alkyl ester to obtain XY. In certain embodiments, X' is coupled with an amide (Y') containing an amino alcohol.

[0081] As shown in Figure 5, amino alcohols can be synthesized from amide-derivative amino acids containing an ester moiety in which various R' groups (e.g., R'=H or alkyl group) are bonded to the ester oxygen. For example, the hydroxyl group can be converted by reacting the ester with any activated ester reagent such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI), hydroxybenzotriazole (HOBt), and / or acetonitrile (ACN) at room temperature. Alternatively, the ester can also be converted to a hydroxyl group by reacting it with any borohydride-based reducing agent such as sodium cyanoborohydride, sodium triacetoxyborohydride, or sodium borohydride in a reaction medium containing tetrahydrofuran (THF) and / or water at about 0-10°C. In some embodiments, for example, when R' is an alkyl group, the ester moiety can be directly reduced using a reducing agent such as a THF solution of lithium aluminum hydride (LiAlH4).

[0082] As illustrated in Figure 7, the coupling of fatty acids with amides containing amino alcohols can be carried out by amide coupling reactions. See also Figure 9. Examples of coupling agents include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI / HOBt), benzotriazole-1-yloxytripyrrolidinophosphonium hexafluorophosphonium (PYBOP), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), and / or N,N'-dicyclohexylcarbodiimide / 1-hydroxybenzotriazole (DCC / HOBt).

[0083] Those skilled in the art who benefit from this disclosure will also be able to imagine methods utilizing other coupling reactions known in the art.

[0084] Before, during, or after coupling to obtain XY, any ester or carbonyl groups present in Y' or XY are reduced to alcohols by introducing hydrides and / or alkyl anions into Y' or XY using a reducing agent Z'.

[0085] In certain embodiments, Z' is any agent suitable for introducing a hydride or alkyl anion to Y' or XY, including, but not limited to, lithium aluminum hydride; methylmagnesium bromide; ethylmagnesium bromide; methylphenylmagnesium bromide; phenylmagnesium bromide; n-butyllithium; or sec-butyllithium.

[0086] In certain embodiments, to introduce further functional groups into the molecules of the surfactant derivative according to the present invention, for example, alkoxylation and / or sulfur oxidation of the side chain alcohol may be performed.

[0087] Linear sophorolipid derivative compounds In some embodiments, the XYZ surfactant molecules of the present invention include a sophorolipid (SLP) backbone. Sophorolipids are glycolipid biosurfactants produced, for example, by various yeasts belonging to the Star Mellera clade. SLPs have a structure in which the disaccharide sophorose is bonded to a long-chain hydroxy fatty acid. SLPs may include a structure in which a partially acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose unit is bonded to 17-L-hydroxyoctadecanoic acid or 17-L-hydroxy-Δ9-octadecenoic acid by a β-glycosidic bond. The hydroxy fatty acid may have, for example, 11 to 20 carbon atoms and may contain one or more unsaturated bonds. Furthermore, the sophorose residue may be acetylated at the 6th and / or 6' position. The carboxyl group of the fatty acid may be free (acidic or linear) or internally esterified at the 4" position (lactone type). In many cases, fermentation of SLP produces a mixture of hydrophobic (water-insoluble) SLP (e.g., lactone-type SLP, monoacetylated linear SLP, diacetylated linear SLP, etc.) and hydrophilic (water-soluble) SLP (e.g., non-acetylated linear SLP, etc.).

[0088] In this specification, the terms “sophorolipid,” “sophorolipid molecule,” “SLP,” or “SLP molecule” encompass all forms of SLP molecules and their isomers, including, for example, acidic (linear) SLPs and lactone SLPs. Furthermore, the terms also encompass monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs having hydrophobic chains of various lengths, SLPs with attached fatty acid-amino acid complexes, and other SLPs, including those described and / or not described herein.

[0089] In some embodiments, the SLP molecule according to the present invention is represented by general formula (3) and / or general formula (4) and is obtained as an aggregate of multiple structural congeners.

[0090] [ka]

[0091] In the formula, R 1 and R 1’ each independently represent a saturated hydrocarbon chain or one or more, particularly one, unsaturated hydrocarbon chains having 8 to 20 carbon atoms. These hydrocarbon chains may be either linear or branched and may contain one or more hydroxy groups; R 2 and R 2’ each independently represent a hydrogen atom, a saturated alkyl functional group, or one or more, particularly one, unsaturated alkyl functional groups having 1 to 9 carbon atoms, more preferably unsaturated alkyl functional groups having 1 to 4 carbon atoms. These alkyl functional groups may be either linear or branched and may contain one or more hydroxy groups; R 3 R 3’ R 4 and R 4’ each independently represent a hydrogen atom or -COCH3. R 5 is usually --OH, but is not limited thereto.

[0092] In certain embodiments, the SLP molecules according to the present invention have advantageous micelle sizes. For example, in some embodiments, the sophorolipid molecules form micelles with sizes less than 500 nm, less than 100 nm, less than 50 nm, less than 25 nm, less than 15 nm, or less than 10 nm. The size of the micelles and their amphiphilic properties improve the permeability into pores, increasing the contact with impurities within the pores.

[0093] The present invention provides materials and methods for manufacturing, derivatizing, and purifying sophorolipids (SLP). The present invention is suitable for the industrial-scale production of purified SLP derivatives and is advantageous in that it uses safe and environmentally friendly, i.e., "green", materials and processes.

[0094] In certain embodiments, the present invention provides SLP derivative molecules, including those described throughout the drawings and the present specification.

[0095] Preparation of standard sophorolipid X' substrate In some embodiments, the method of the present invention first comprises the step of preparing a standard SLP molecular "substrate" for producing derivatized SLP and / or purified SLP. In certain embodiments, the method comprises the step of culturing sophorolipid-producing yeast in a liquid fermentation reactor containing a oleochemical raw material tailored for the purpose, to obtain a yeast culture product. This yeast culture product comprises a fermentation broth, yeast cells, and SLP having a mixture of two or more molecular structures.

[0096] The mixture of molecular structures may include, for example, lactone-type SLPs, linear SLPs, deacetylated SLPs, monoacetylated SLPs, diacetylated SLPs, esterified SLPs, SLPs having hydrophobic chains of various lengths, SLPs with fatty acid-amino acid complexes attached, and other SLPs, including those described and / or not described in this disclosure.

[0097] In certain embodiments, the distribution of the SLP molecule mixture can be altered by adjusting fermentation parameters such as raw materials, fermentation time, and dissolved oxygen level.

[0098] In this specification, “fermentation” means the proliferation or culture of cells under controlled conditions. Proliferation may be either aerobic or anaerobic. Unless otherwise specified in the context, this term encompasses both the proliferation stage and the product biosynthesis stage in the process.

[0099] In this specification, “broth,” “culture broth,” or “fermented broth” means a culture medium containing at least nutrients. When broth is referred to after a fermentation process, this broth may also contain microbial growth byproducts and / or microbial cells.

[0100] The microbial growth vessel used in the present invention may be any industrial fermenter or culture reactor. In this specification, the terms “reactor,” “bioreactor,” “fermentation reactor,” or “fermentation vessel” include fermentation apparatus consisting of one or more vessels and / or towers or piping. Such reactors include, but are not limited to, continuous stirred-tank reactors (CSTRs), immobilized cell reactors (ICRs), trickle-bed reactors (TBRs), bubble towers, gas-lift fermenters, static mixers, or other vessels or apparatus suitable for gas-liquid contact. In some embodiments, a bioreactor may include a first growth reactor and a second fermentation reactor. Therefore, where there is a reference to adding a substrate to a bioreactor or fermentation reaction, it should be understood to include adding it to one or both of these reactors, as necessary.

[0101] In one embodiment, the fermentation reactor may be equipped with, or connected to, functional control devices / sensors for measuring important factors in the culture process such as pH, oxygen, pressure, temperature, stirring shaft power, humidity, viscosity and / or microbial density, and / or metabolite concentrations.

[0102] In another embodiment, the container may also be capable of monitoring the growth of microorganisms inside the container (e.g., measuring cell count and determining growth stage). Alternatively, a sample may be taken from the container for counting, purity measurement, SLP concentration and / or visible oil content monitoring. For example, in one embodiment, sampling may be performed every 24 hours.

[0103] The inoculum microbial material according to the method of the present invention preferably comprises cells and / or trophozoites of a desired microorganism. These cells and / or trophozoites can be prepared using any known fermentation method. If necessary, the inoculum may be pre-mixed with water and / or liquid growth medium.

[0104] The microorganisms used in this invention may be natural microorganisms or genetically modified microorganisms. For example, a microorganism may be transformed with a specific gene to express a specific characteristic. Alternatively, the microorganism may be a mutant of a desired strain. In this specification, "mutant" means a variant or subtype of a reference microorganism strain or gene, and a mutant has one or more gene mutations (e.g., point mutations, missense mutations, nonsense mutations, deletions, duplications, frameshift mutations, or extensions of repetitive sequences) relative to the reference microorganism. Methods for producing mutants are well known in the field of microbiology. For example, ultraviolet mutagenesis and nitrosoguanidine are widely used for this purpose.

[0105] In a preferred embodiment, the microorganism is a yeast or fungus. Suitable species of yeast and fungus for use in the present invention include, for example, yeasts of the genus Starmerella and / or yeasts of the genus Candida, specifically, but not limited to, Starmerella (Candida) bombicola, Candida apicola, Candida batistae, Candida floricola, Candida riodsensis, Candida stellate, and / or Candida cuoi. In a particular embodiment, the microorganism is Starmerella bombicola, for example, strain ATCC 22214.

[0106] In certain embodiments, the cultivation method utilizes liquid fermentation using a liquid growth medium containing lipid-based chemical raw materials that have been adjusted for the purpose.

[0107] In one embodiment, the liquid growth medium contains one or more carbon sources. The carbon sources may be carbohydrates such as glucose, dextrose, sucrose, lactose, fructose, trehalose, mannose, mannitol and / or maltose; organic acids such as acetic acid, fumaric acid, citric acid, propionic acid, malic acid, malonic acid and / or pyruvic acid; alcohols such as ethanol, propanol, butanol, pentanol, hexanol, isobutanol and / or glycerol; oils and fats such as canola oil, maduka oil, soybean oil, rice bran oil, olive oil, corn oil, sunflower oil, sesame oil and / or flaxseed oil; and powdered molasses. These carbon sources may be used individually or in combination of two or more.

[0108] In a preferred embodiment, the fermentation medium contains dextrose. In another preferred embodiment, the oleochemical raw materials are prepared to include a source of oleic acid. In certain embodiments, the oleic acid content is high, for example, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, or at least 99%. In some embodiments, the oleochemical raw materials consist solely of a source of oleic acid.

[0109] Examples of sources of oleic acid include, but are not limited to, high-oleic soybean oil, high-oleic sunflower oil, high-oleic canola oil, olive oil, pecan oil, peanut oil, macadamia oil, grapeseed oil, sesame oil, poppy oil, pure oleic acid, maduka oil, alkyl oleate, and / or triglycerides of oleic acid. In preferred embodiments, high-oleic soybean oil, pure oleic acid, and / or alkyl oleate are used.

[0110] In certain embodiments, using a high-oleic acid oleic acid chemical raw material, and / or a oleic acid chemical raw material containing only oleic acid, is advantageous because it yields a yeast culture product with reduced molecular structural diversity of SLPs compared to using a raw material containing other fatty acid sources. In this case, the main SLP molecules obtained are those having a C18 carbon chain and one unsaturated bond at the 9th carbon. For example, in certain embodiments, the proportion of SLP molecules containing a C18 carbon chain is higher than 50%, preferably higher than 70%, and more preferably higher than 85%.

[0111] In one embodiment, the liquid growth medium includes a nitrogen source. Examples of nitrogen sources include yeast extract, potassium nitrate, ammonium nitrate, ammonium sulfate, ammonium phosphate, ammonia, urea, and / or ammonium chloride. These nitrogen sources may be used individually or in combination of two or more.

[0112] In one embodiment, the liquid growth medium may contain one or more inorganic salts. Examples of inorganic salts may be potassium dihydrogen phosphate, monopotassium phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, potassium chloride, magnesium sulfate, magnesium chloride, iron sulfate, iron chloride, manganese sulfate, manganese chloride, zinc sulfate, lead chloride, copper sulfate, calcium chloride, calcium carbonate, calcium nitrate, magnesium sulfate, sodium phosphate, sodium chloride, and / or sodium carbonate. These inorganic salts may be used individually or in combination of two or more.

[0113] In one embodiment, the culture medium contains growth factors and micronutrients for microorganisms. The culture medium may also contain inorganic nutrients, including trace elements such as iron, zinc, copper, manganese, molybdenum, and / or cobalt. Furthermore, sources of vitamins, essential amino acids, proteins, and trace elements may be included, for example, corn flour, peptone, yeast extract, potato extract, beef extract, soybean extract, banana peel extract, etc., or they may be included in the form of purified products. In addition, amino acids, such as those useful for protein biosynthesis, may be included.

[0114] Furthermore, the above-described culture method allows for the supply of oxygen to the cultured material during growth. In one embodiment, low-oxygen air is removed by utilizing the slow movement of air, and oxygenated air is introduced. The oxygenated air may be atmospheric air that is replenished daily by mechanisms such as an impeller that mechanically agitates the liquid, or an air spagger that supplies bubbles to the liquid to dissolve oxygen.

[0115] In certain embodiments, controlling the dissolved oxygen (DO) level during fermentation suppresses the structural diversity of SLP molecules produced in the yeast culture product. It is preferable to maintain a high DO level, for example, by supplying oxygen at a rate of 50 mM or more, 55 mM or more, 60 mM or more, 65 mM or more, or 70 mM or more per liter per hour.

[0116] In some embodiments, the culture method may further include the step of adding an acid and / or antimicrobial agent to the liquid medium before and / or during the culture process. Antimicrobial agents or antibiotics (e.g., streptomycin, oxytetracycline) are used to protect the culture medium from contamination. However, in some embodiments, contamination of the culture medium is prevented by metabolites produced in the yeast culture medium exerting a sufficient antimicrobial effect.

[0117] In one embodiment, the components of the liquid culture medium may be optionally sterilized before inoculation into the reactor. In one embodiment, the liquid growth medium can be sterilized by immersing the components of the liquid culture medium in water at a temperature of approximately 85-100°C. In one embodiment, the components can be sterilized by dissolving them in 1-3% hydrogen peroxide solution at a ratio of 1:3 (w / v).

[0118] In one embodiment, the apparatus used for culturing is sterile. The culture apparatus (reactor / container, etc.) may be separate from the sterilization unit (e.g., autoclave) or connected to the sterilization unit. The culture apparatus may include a sterilization unit that performs situ sterilization before inoculation begins. Components of the apparatus, such as gaskets, openings, and piping, may be sprayed with, for example, isopropyl alcohol. Air sterilization can be carried out by methods known to those skilled in the art. For example, air from the atmosphere may pass through at least one filter before being introduced into the container. In other embodiments, the culture medium may be pasteurized, or optionally, the medium may be left unheated and its growth of undesirable microorganisms may be controlled by utilizing pH and / or low water activity.

[0119] The pH of the culture medium needs to be suitable for the target microorganism. In some embodiments, the pH is about 2.0 to about 7.0, about 3.0 to about 5.5, about 3.25 to about 4.0, or about 3.5. Buffers and pH adjusters such as carbonates and phosphates may be used to stabilize the pH near a preferred value. In certain embodiments, a base solution is used to adjust the pH of the culture medium to a preferred level. For example, a 15% to 30% or 20% to 25% NaOH solution may be used. The base solution may be included in the growth medium and / or may be added to the fermentation reactor as needed to adjust the pH during cultivation.

[0120] In one embodiment, the culture method is carried out at approximately 5°C to 100°C, approximately 15°C to 60°C, approximately 20°C to 45°C, approximately 22°C to 35°C, or approximately 24°C to 28°C. In one embodiment, the culture may be carried out continuously at a constant temperature. In another embodiment, the culture may be carried out while changing the temperature.

[0121] According to the method of the present invention, microorganisms can be cultured in a fermentation system for a period sufficient to obtain desired effects, such as the production of a desired amount of cellular biomass or a desired amount of SLP. By-products produced by the growth of microorganisms may be retained within the microbial cells, secreted into the growth medium, or both. The biomass content may be, for example, 5 g / l to 180 g / l or more, 10 g / l to 150 g / l, or 20 g / l to 100 g / l.

[0122] In certain embodiments, the fermentation of the yeast culture takes place for approximately 40–150 hours, or approximately 48–140 hours, or approximately 72–130 hours, or approximately 96–120 hours. In certain embodiments, the fermentation time is in the range of 48–72 hours, or 96–120 hours.

[0123] In some embodiments, the fermentation cycle is terminated when the dextrose and / or oleic acid concentrations in the culture medium are depleted (e.g., at levels of 0% to 0.5%). In some embodiments, the end of the fermentation cycle is determined when the microorganisms begin to consume trace amounts of SLP.

[0124] In certain embodiments, the production of the SLP molecule "substrate" further includes post-fermentation conversion of the SLP molecule generated in the yeast culture product. In one embodiment, linear SLP is obtained by hydrolysis of the crude composition of this SLP. In some embodiments, the linear SLP is deacetylated. In some embodiments, the linear SLP is totally acetylated.

[0125] In some embodiments, the method includes a step of alkaline hydrolysis of the crude SLP. For example, in one embodiment, the crude SLP may be mixed with a base solution of equimolar to 1.5 molar concentration, such as a solution of sodium hydroxide, potassium hydroxide and / or ammonium hydroxide, to adjust the pH to, for example, about 4 to 11, about 5 to 11, about 6 to 12, preferably about 7 to 9. In certain embodiments, this step is achieved by treating the crude SLP with a hydroxide salt solution for 2 to 24 hours, 3 to 20 hours, or 4 to 16 hours under high temperature conditions, such as 75 to 100°C, 80 to 95°C, or 85 to 90°C.

[0126] According to the method of the present invention, the lactone bond of lactone-type SLP is cleaved by the hydrolysis process, converting lactone-type SLP into a crude product of linear SLP. Figure 8. In certain embodiments, a portion of the crude product of linear SLP is acetylated, diacetylated, or totally acetylated, in proportion to, for example, 1% to 100%, 5% to 75%, or 10% to 50% of the total amount of SLP molecules. In another embodiment, monoacetylated or diacetylated SLP molecules may be deacetylated by the same alkaline hydrolysis process.

[0127] In a preferred embodiment, the linear SLP serves as a standard substrate for one or more derivatization and / or purification reactions.

[0128] In certain embodiments, long-chain amide derivatives (e.g., C18) can be obtained by introducing an amide containing a cationic amino acid functional group into a linear SLP substrate. Figure 9. In some embodiments, linear SLP substrates can be converted to short-chain amides (e.g., C9) by first cleaving the fatty acid terminus of the linear SLP substrate by oxidative cleavage, and then introducing an amide containing a cationic amino acid functional group into the cleaved acid. Figures 10A-10B.

[0129] Ion exchange / purification of cationic SLP derivatives In certain embodiments, the cationic properties of the SLP derivatives of the present invention allow for selective purification using cation exchange resins, such as selective retention of cationic species and / or selective removal of unreacted SLPs or SLPs that do not possess the desired carbon chain length or properties. Therefore, in certain embodiments, the present invention provides a novel method for purifying SLPs and SLP derivatives using cation exchange resins.

[0130] In certain embodiments, after introducing a cationic cargo, the resulting cationic SLP derivative can be extracted from the reaction mixture by a standard liquid-liquid extraction method using an organic solvent, preferably ethyl acetate, washed with sodium carbonate buffer at pH 9.0, and concentrated under reduced pressure (e.g., about 200-250 mbar, or about 240 mbar). The mixture can then be resuspended in deionized water and purified using a cation exchange resin.

[0131] In certain embodiments, the extracted cationic SLP is circulated through an ion exchange layer using a pump, such as a peristaltic pump. The ion exchange layer contains equimolar to 1.5 molar amounts of cation exchange sites relative to the concentration of the crude linear cationic SLP, and the circulation time is 2 to 20 hours, 3 to 15 hours, or 4 to 12 hours.

[0132] In a preferred embodiment, the recovery of SLP cationic derivatives from the cation exchange resin can be carried out using an electrolyte solution containing a high concentration of monovalent metal cations. Here, "high concentration" refers to 1.5 to 15 molar equivalents or 2 to 10 molar equivalents relative to the concentration of the SLP cationic derivative. The high concentration of monovalent metal cations competitively eliminates and replaces the bound SLP cationic derivative on the resin, thereby obtaining a flow of high-purity SLP cationic derivatives.

[0133] In some embodiments, after introducing a cationic cargo, the resulting cationic SLP derivative can be purified by the following method. First, the cationic SLP derivative is stirred with a saturated ammonium chloride solution to obtain a stirred mixture. Then, CH2Cl2 is added to the stirred mixture as a solvent (three times) to extract the cationic SLP derivative and obtain an extract mixture. Next, MgSO4 or Na2SO4 is added to remove trace amounts of water from the extract mixture, and the extract mixture is dried under pressure at 35-45°C (e.g., 350-450 mbar or 400 mbar) to remove the CH2Cl2 solvent. Then, a 21% NaOEt / EtOH solution and a solution of the base NaHCO3 or KHCO3 dissolved in ethanol are added to remove the acetyl R group from the cationic SLP derivative. Subsequently, the resulting deacetylated linear cationic SLP derivative can be converted to a hydrochloride salt by reacting it with a 1.25 M hydrochloric acid / ethanol solution.

[0134] Exemplary formulations and methods of use In some embodiments, the XYZ surfactant compounds according to the method of the present invention can be used as active and / or inactive ingredients in environmentally friendly, i.e., "green," consumer and industrial products.

[0135] For example, XYZ surfactant compounds can be used as active and / or inactive ingredients in a wide range of products, including cleaning agents, personal care and cosmetic formulations, disinfectants, food and beverages, pharmaceuticals and supplements, agricultural applications, oil and gas production applications, animal health formulations, metalworking oils, paints and coatings, and mining reagents.

[0136] Depending on the specific application, other components may be added to the composition. Examples of additives include carriers, buffers, pH adjusters, viscosity modifiers, emulsifiers, emollients, syndetics, cleaning aids, solvents, acids, preservatives, nutrients, pharmaceuticals, nutritional supplements, pesticides, animal feed, disinfectants, cleaning aids, polymers, auxiliary surfactants, fragrances, pigments and other colorants, flavorings, oils, and food ingredients, all of which are specific components suited to the intended use.

[0137] In some embodiments, the XYZ surfactant molecules produced by the method of the present invention can be used as active ingredients in environmentally friendly, i.e., "green" cleaning compositions for efficiently disinfecting and / or sterilizing materials and / or surfaces contaminated with, for example, bacteria, viruses, fungi, molds, mildews, protozoa, biofilms, and / or other infectious organisms. In preferred embodiments, the compositions and methods are advantageous in that they have at least equivalent efficacy to other chemical and / or synthetic cleaning formulations such as antimicrobial peptides (AMPs) or cationic host defense peptides, QACs, and SCAs, with respect to disinfecting and / or sterilizing materials and / or surfaces.

[0138] Furthermore, the XYZ surfactant of the present invention possesses unique stability and effectiveness across multiple pH ranges, making it suitable for a wide range of cleaning applications. Therefore, in addition to its disinfectant properties, the XYZ surfactant of the present invention can exhibit improved cleaning action against a wide variety of stains, including anionic stains such as anionic sugars and glycoproteins. This is particularly useful considering that many pathogens of public health concern are typically transmitted through media such as biofilms containing stains, which protect organisms from the effects of common disinfectants, for example, fecal matter, respiratory droplets, vomit, blood, other bodily fluids, and / or common disinfectants.

[0139] In this specification, “harmful” or “pathogenic” microorganisms mean any single-celled or cell-free organism capable of infecting, disease, or causing other types of harm to another organism. In this specification, harmful or pathogenic microorganisms are infectious pathogens, including, for example, bacteria, cyanobacteria, biofilms, viruses, virions, viroids, fungi, molds, mildews, protozoa, prions, and algae.

[0140] In this specification, “undesirable” microorganisms mean non-pathogenic species that, by growing on or within a product, may cause visible growth, odor, spoilage, or other sensory irritation damage to the product. Such organisms are not necessarily capable of causing infection, but may spoil food, contaminate surfaces, form visible biofilms, and / or produce undesirable odors. The growth of such organisms may render products, particularly food, cosmetics, cleaning products, and personal care products, unsuitable for use. Non-limiting examples of undesirable microorganisms that cause spoilage or other physical changes (but not pathogenic) to a product include certain species of bacteria belonging to genera such as Lactobacillus, Pediococcus, Micrococcus, Streptococcus, Propionibacterium, Streptomyces, Actinomyces, and Bacillus, as well as certain species of fungi belonging to genera such as Giotrichum, Penicillium, Saccharomyces, and Zygosaccharomyces.

[0141] In this specification, “contaminant” or “dirt” means an impurity, i.e., any substance that causes fouling or impurity of another substance or object. Contaminants may be living or non-living, and may be inorganic or organic substances or deposits. Furthermore, contaminants include, but are not limited to, hydrocarbons, e.g., petroleum or asphaltenes; oils and greases (FOG), e.g., cooking grease, vegetable oils and lards; lipids; waxes, e.g., paraffin; resins; microorganisms, e.g., bacteria, biofilms, viruses, fungi, molds, mildews, protozoa, parasites and other harmful or undesirable microorganisms; stains; bodily fluids; plant matter; or any other substance, e.g., dirt, dust, scale, sludge, cladding, slag, grime, scum, shmoo, plaque, buildup or residue.

[0142] In this specification, “biofilm” means a complex collection of microorganisms such as bacteria, yeasts, and fungi, in which each cell is attached to one another and / or to the surface via an extracellular matrix. Cells within a biofilm are physiologically different from the individual floating cells of the same organism, which may float or move in a liquid culture medium.

[0143] In this specification, “fouling” means a phenomenon in which the structural and / or functional integrity of a device is compromised by the accumulation or deposition of contaminants on a surface, for example, on the surface of a device. Fouling can cause clogging, blockage, deterioration, corrosion, and other problems associated therewith, and can occur on metallic or nonmetallic materials and / or surfaces. Fouling caused by living organisms, such as biofilms, is called “biofouling.”

[0144] In this specification, “cleaning” means removing undesirable dirt, chemicals, or microbial contaminants from materials and / or surfaces that are soiled or fouled. Such contaminants indicate that the surface or material has been exposed to environmental dirt, fluids, or microorganisms, which are undesirable because they can cause visible soiling on the surface, render the surface or material unusable for its intended purpose, produce undesirable odors, or infest undesirable and / or harmful microorganisms.

[0145] In this specification, “preservative” means preventing the growth of undesirable and / or harmful microorganisms on a surface or in a material for a specific period, measured from the time of treatment, at least 24 hours, preferably up to 7 days, and most preferably 30 days or more. In certain preferred embodiments, the material to be preserved is a liquid, food, cosmetic, or personal care product.

[0146] In this specification, “preventing” a situation or event means avoiding, delaying, preventing, or minimizing the occurrence of specific signs or symptoms of the situation or event. “Prevention” may be achieved absolutely or completely, but is not necessarily required, and the situation or event may still develop further. “Prevention” includes reducing the severity of the occurrence of the situation or event and / or deterring the situation or event from developing into a more serious situation.

[0147] In this specification, “control” means the physical or mechanical removal of contaminants such as dirt and microorganisms. Control may include the use of preservatives, fungicides, or biocides. Furthermore, “residual control” means pre-treating a surface, fluid, or material using a process or composition that can kill or damage, or prevent adhesion, growth, or survival of undesirable and / or harmful microorganisms, even if they come into contact with the surface or material after a period of time has elapsed since the treatment. Residual control treatment makes the surface or material less susceptible to colonization by undesirable and / or harmful microorganisms after treatment.

[0148] In this specification, “sterilize” means inactivating or killing at least 99.9% of undesirable or harmful microorganisms present on a surface or in a material within 10 minutes, preferably 5 minutes, and most preferably 2 minutes, measured from the time the composition comes into contact with the microorganisms (i.e., the time of exposure).

[0149] In this specification, “disinfect” means irreversibly inactivating or killing at least 99.999% of undesirable and / or harmful microorganisms within 10 minutes, preferably within 5 minutes, and most preferably within 2 minutes, from the time the composition comes into contact with the microorganisms (i.e., the time of exposure).

[0150] In a particular preferred embodiment, at least 99.9% of surrogate bacteria representing Gram-positive and Gram-negative bacteria, i.e., two types of surrogate bacteria, are killed within 10 minutes. This means that the surface and / or material is "sterilized".

[0151] In one of the most preferred embodiments, at least 99.999% of specific surrogate bacteria, representing Gram-positive and Gram-negative bacteria respectively, are killed within 10 minutes. This means that the surface and / or material is "disinfected".

[0152] A "surrogate bacterium" refers to a strain of bacteria recognized by regulatory authorities in various countries, such as the United States and the EU, as representing an entire class of microorganisms. In this case, Staphylococcus aureus is the most widely recognized surrogate bacterium among Gram-positive bacteria. This is because Staphylococcus aureus is considered the most difficult bacterium to disinfect or kill among all related Gram-positive growing bacteria (with some exceptions). Similarly, Salmonella enterica or Pseudomonas eruginosa are generally considered the most difficult bacterium to kill or disinfect among all related Gram-negative bacteria.

[0153] The cleaning composition of the present invention can be formulated and supplied as a liquid, suspension, emulsion, soluble powder and / or soluble granules, compressed powder, uncompressed powder, diluted spray, concentrate, aerosol, foam, encapsulated soluble pod, gel, and / or as a wet-type or water-activated cloth, sponge, wipe or other substrate. The cleaning composition can be used, for example, as a toilet bowl cleaner, laundry detergent, dishwashing detergent, hard and soft surface cleaner, water purifier, air purifier, and / or carpet cleaner.

[0154] Based on the inherent toxicological safety of this composition, certain preferred embodiments can create novel disinfectants that are safe to use in contact with skin, can be used in food preparation and storage areas, and in environments with children and pets, and can also be used as food preservatives. In additional preferred embodiments, surfaces can be disinfected in hospitals and nursing homes without evacuating patients, and without requiring personal protective equipment (PPE) which is essential with currently used disinfectants such as hypochlorites and QACs.

[0155] In some embodiments, the XYZ surfactant derivative molecules produced by the method of the present invention can be used as active ingredients in consumer products having the function of preservatives that prevent decay and / or proliferation by harmful and / or undesirable organisms. Such consumer products include, for example, cleaning products (e.g., disinfectants, general-purpose detergents, glass cleaners, laundry detergents and dishwashing detergents), home care products (e.g., floor waxes and air fresheners), personal care products (e.g., skincare products and haircare products), cosmetics (e.g., makeup and nail polish), coatings and building materials (e.g., paints, lacquers, primers, putties, gypsum boards and caulking materials), and in some embodiments, health products, food and beverages.

[0156] The present invention is advantageous in that it eliminates the environmental risks common to synthetically produced surfactants and disinfectants such as QACs. Because the manufacturing process for these molecules uses natural ingredients and employs a gentle process, there is no generation of hazardous gases or toxic compounds associated with the production of QACs, and the risks of water source contamination and disruption of wastewater treatment processes are also reduced. The molecules of the present invention are readily biodegradable and do not remain in the environment. Therefore, the present invention can be used in various industries, for example, as a "green" disinfectant, bactericide, preservative, detergent, and / or conditioner.

[0157] In certain embodiments, a cleaning composition and / or consumer product comprising the XYZ surfactant according to the present invention comprises the XYZ surfactant in amounts of 0.1-10% by weight, 0.1-9.0% by weight, 0.1-8.0% by weight, 0.1-7.0% by weight, 0.1-6.0% by weight, 0.1-5.0% by weight, 0.1-4.0% by weight, 0.1-3.0% by weight, 0.1-2.0% by weight, 1.0-9.0% by weight, 1.0-5.0% by weight, 1.0-3.0% by weight, 3.0-10% by weight, 3.0-7.0% by weight, 5.0-10% by weight, 5.0-9.0% by weight, 6.0-10% by weight, 7.0-10% by weight, and 8.0-10% by weight. In certain embodiments, the XYZ surfactant is included in the cleaning composition at a concentration of about 1 ppm to about 200 ppm, or about 2 ppm to about 250 ppm, or about 5 ppm to about 300 ppm, or about 10 ppm to about 350 ppm, or about 25 ppm to about 400 ppm, or about 50 ppm to about 450 ppm, or about 75 ppm to about 500 ppm, or about 100 ppm to about 600 ppm, or about 125 ppm to about 750 ppm, or about 150 ppm to about 1,000 ppm, or about 175 ppm to about 1,500 ppm, or about 0.5 ppm to about 2,000 ppm.

[0158] In one particular embodiment, the XYZ surfactant is included in a cleaning composition or consumer product at a concentration of 50 to 500 ppm. In another particular embodiment, the XYZ surfactant is included at a concentration of 100 to 1,500 ppm.

[0159] In certain embodiments, the pH of the cleaning composition is in the range of 2.0 to 12.0, 2.5 to 11, 3.0 to 10.0, 3.0 to 9.0, or 4.0 to 8.0. To maintain the pH at an appropriate level, known pH adjusters such as hydrochloric acid, sulfuric acid, sodium carbonate, sodium bicarbonate, sodium hydroxide, ammonium hydroxide, calcium hydroxide, magnesium hydroxide, acetic acid, lactic acid, and / or citric acid may be used.

[0160] Optionally, the cleaning composition may further contain one or more other components. These other components may include, for example, carriers (e.g., water), other biosurfactants, other surfactants (e.g., polyalkyl glucosides such as caprylyl glucoside and lauryl glucoside, amine oxides), hydrophilic and / or hydrophobic syndetics, metal ion chelating agents, cleaning aids (e.g., potassium carbonate, sodium hydroxide, glycerin, citric acid, lactic acid), solvents (e.g., water, ethanol, methanol, isopropanol), organic and / or inorganic acids (e.g., lactic acid, citric acid, acetic acid, boric acid), plant extracts, crosslinking agents, and chelating agents (e.g., potassium citrate). Examples of such substances include sodium citrate, sodium gluconate, citric acid, EDTA, DEDTA, fatty acids, alcohols, reducing agents, oxidizing agents, calcium salts, carbonates, buffers, enzymes, dyes, colorants, fragrances (e.g., d-limonene, thymol, citral, lavender), preservatives (e.g., octylisothiazolinone, methylisothiazolinone), propellants, terpenes (e.g., d-limonene), sesquiterpenoids, terpenoids, emulsifiers, deemulsifiers, foaming agents, antifoaming agents, bleaching agents, polymers, thickeners and / or viscosity enhancers (e.g., xanthan gum, guar gum).

[0161] In one exemplary embodiment, the XYZ surfactant according to the present invention contained in the cleaning composition may be formulated or supplied as a solution (1-50%) dissolved in a glycol-based solvent such as glycerol, propylene glycol, and / or butylene glycol. In a particular embodiment, this exemplary formulation or supply may further contain one or more acids, such as acetic acid, lactic acid, and / or citric acid, at up to 5% relative to the active antimicrobial component.

[0162] In certain embodiments, the cleaning composition may contain essential oils. Essential oils are volatile aromatic oils. They may be synthesized or obtained from plants by distillation, expression (pressing), or extraction, and usually retain the aroma or flavor of the original plant from which the essential oil was extracted. Useful essential oils may also have antiseptic properties. Some essential oils also have flavoring properties. Useful essential oils include citra, thymol, menthol, methyl salicylate (wintergreen oil), eucalyptol, carvacrol, camphor, anethole, carvone, eugenol, isoeugenol, limonene, ocimene, n-decyl alcohol, citronellol, α-salpineol, methyl acetate, citronellyl acetate, methyl eugenol, cineole, linalool, ethyl linaraol, safflower vanillin, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, and laurel. Examples of such oils include, but are not limited to, pine oil, cedar leaf oil, gerianol, verbenone, anise oil, bay oil, benzaldehyde, bergamot oil, bitter almond oil, chlorothymol, cinnamaldehyde, citronella oil, clove oil, coal tar, eucalyptus oil, guaiacol, tropolone derivatives such as hinokitiol, lavender oil, mustard oil, phenol, phenyl salicylate, pine oil, pine needle oil, sassafrass oil, spike lavender oil, strax, thyme oil, tolu balsam, turpentine oil, clove oil, and combinations thereof.

[0163] In some embodiments, the composition comprises additional and / or other biosurfactants in the form of crude and / or purified products. Examples of additional biosurfactants according to the present invention include glycolipids, lipopeptides, flavolipids, phospholipids, fatty acid esters, and high molecular weight biopolymers, such as lipoproteins, lipopolysaccharide-protein complexes, and / or polysaccharide-protein-fatty acid complexes.

[0164] In one embodiment, the additional and / or other biosurfactant is a glycolipid, such as rhamnolipid (RLP), cellobiose lipid, trehalose lipid and / or mannosylerythritol lipid (MEL). Natural (or non-derivativeized) SLPs may also be used. In one embodiment, the biosurfactant is a lipopeptide, such as surfactant, itulin, fengisin, altrofactin, amphisin, viscosin, lichenisin, penibacterin, polymyxin and / or batasin. In one embodiment, the biosurfactant is another type of amphiphilic molecule, such as esterified fatty acids, saponins, cardiolipin, pullulan, emulsan, lipomanan, alasan and / or liposan.

[0165] In some embodiments, the biosurfactant is used in crude form. In this case, the biosurfactant molecule is present in the growth medium (e.g., broth) in which the biosurfactant-producing microorganism is cultured and is recovered from the growth medium without purification. In crude form, the proportion of amphiphilic molecules in the growth medium may be, for example, at least 0.001%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In another embodiment, the biosurfactant is extracted from the growth medium and may optionally be further derivatized and / or purified.

[0166] In one embodiment, the biosurfactant is an ester of the biosurfactant with an alcohol, such as lactone-type sophorolipid ethyl ester, lactone-type sophorolipid methyl ester, lactone-type sophorolipid isopropyl ester, lactone-type sophorolipid butyl ester, linear sophorolipid ethyl ester, linear sophorolipid methyl ester, linear sophorolipid isopropyl ester, or linear sophorolipid butyl ester.

[0167] In one embodiment, the biosurfactant is a metal-biosurfactant complex in which an antimicrobial metal (e.g., silver) is attached to a biosurfactant molecule. In a particular embodiment, this complex is a silver-sophorolipid complex.

[0168] In one embodiment, the biosurfactant is a mixture of lipopeptide biosurfactants (e.g., surfactant, iturin, fengisin, and / or lichenisin) produced by, for example, Bacillus amyloricephaciens NRRL B-67928 or Bacillus subtilis NRRL B-68031. In certain embodiments, this mixture of lipopeptides contains more than 50% surfactant.

[0169] Disinfection methods, sterilization methods and / or preservation methods In a preferred embodiment, the present invention provides a method for disinfecting and / or sterilizing materials (including fluids such as air, water, or both air and water), surfaces, and / or fibers that are contaminated with or adhering to undesirable and / or harmful microorganisms. The method includes the step of applying the cleaning composition according to the present invention to the material, surface, and / or fibers such that the composition comes into contact with the target microorganisms.

[0170] In some embodiments, the present invention provides a method for preserving consumer products, comprising incorporating a cleaning composition and / or surfactant XYZ derivative according to the present invention into the consumer product. Such consumer products include, for example, cleaning products (e.g., disinfectants, general-purpose detergents, glass cleaners, laundry detergents and dishwashing detergents), home care products (e.g., floor waxes and fragrances), personal care products (e.g., skincare products and haircare products), cosmetics (e.g., makeup and nail polish), coatings and building materials (e.g., paints, lacquers, primers, putties, gypsum boards and caulking materials), and in some embodiments, pharmaceuticals, supplements, foods and beverages.

[0171] The aforementioned method has the advantage of being safe to use in environments such as homes, commercial settings, and industrial settings, where humans, plants, and animals are present.

[0172] The method of this invention can be used for disinfection, sterilization, and / or preservation of a wide range of undesirable and / or harmful microorganisms, including both Gram-negative and Gram-positive bacteria, biofilms, viruses (including enveloped viruses), fungi, molds, protozoa, parasites, algae, and other infectious organisms such as helminths and nematodes.

[0173] In certain embodiments, the method can be used to disinfect materials and / or surfaces contaminated with E. coli, Staphylococcus, Salmonella, Campylobacter, and / or Clostridium.

[0174] The cleaning composition can be applied to, for example, hard surfaces, soft porous surfaces, textile products and fibers, countertops, desks, floors, toilets, plastics, glass, ceramics, sinks, bathtubs, toys, doorknobs, carpets, rugs, windows, medical devices or implants, or fluids (e.g., air or water).

[0175] The cleaning composition may be applied directly to the material and / or surface, for example, by spraying it using a spray bottle or pressurized spraying device. Alternatively, it may be applied directly to the material and / or surface by pouring or squeezing the cleaning composition from a container and allowing it to adhere to or be injected by means other than spraying. The cleaning composition may also be applied using a sponge, cloth, wipe, or brush, in which case the cleaning composition is rubbed, spread, or brushed onto the material and / or surface. Furthermore, the cleaning composition may be applied via a washing machine or dishwasher. In addition, the cleaning composition may be diffused into the air as an aerosol, which is useful for disinfecting or removing airborne vectors, microorganisms, and / or allergens.

[0176] The cleaning composition may be used separately from the absorbent and / or adsorbent, or in combination with them. For example, the cleaning composition may be formulated for use with cleaning wipes, sponges (cellulose, synthetic fibers, etc.), paper towels, napkins, cloths, towels, rugs, mop heads, squeegees, and / or other cleaning tools containing the absorbent and / or adsorbent. Alternatively, the cleaning composition may be pre-loaded onto the absorbent and / or adsorbent, absorbed and / or adsorbed by the material during use, or used separately from the absorbent and / or adsorbent.

[0177] Cleaning wipes capable of carrying improved cleaning compositions may be made of absorbent / adsorbent materials. Typically, cleaning wipes have at least one layer of nonwoven fabric material. Non-limiting examples of commercially available cleaning wipes include DuPont 8838, Dexter ZA, Dexter 10180, Dexter M10201, Dexter 8589, Ft. James 836, and Concert STD60LN. All of these cleaning wipes contain a mixture of polyester and wood pulp. Dexter M10201 also contains rayon, which is a wood pulp derivative. The ratio of the cleaning composition to be carried out on the cleaning wipe may be about 2 to 5:1 or about 3 to 4:1. The loading of the cleaning composition onto the cleaning wipe can be carried out by any number of manufacturing methods. Typically, the cleaning wipe is immersed in the cleaning composition until a predetermined loading amount is obtained. Cleaning wipes carrying the improved cleaning composition exhibit superior cleaning action, leaving little to no streaky or film-like residue.

[0178] In one embodiment, disinfection and / or sterilization effects can be obtained by immersing the material and / or surface in the cleaning composition for a sufficient amount of time. For example, the immersion time may be 5 seconds to 10 minutes, 10 seconds to 5 minutes, or 30 seconds to 2 minutes. The shortest exposure time required to obtain the disinfection and / or sterilization effect is preferably less than 60 seconds, and more preferably less than 30 seconds.

[0179] In one embodiment, the cleaning composition may be applied by agitation. This may be done mechanically, for example, using a washing machine or dishwasher, or manually, for example, by scrubbing with a cloth, wipe, sponge or brush.

[0180] In some cases, undesirable and / or harmful organisms present on the surface or material being cleaned may dry out, making it difficult to dissolve them or allow them to come into contact with the disinfectant active ingredient. Furthermore, in some cases, a contaminated surface may not only be contaminated with undesirable and / or harmful microorganisms, but also dirty, i.e., it may contain dirt or other biological material. The presence of such dirt or other biological material makes it more difficult to achieve contact with and disinfection of undesirable and / or harmful microorganisms within the specified time frame of 10 minutes or less required to claim disinfection effectiveness as defined by the U.S. Environmental Protection Agency (EPA) or the European Union (EU). However, the cleaning composition of the present invention is advantageous because it can be used as a "one-step disinfectant" that can clean and disinfect a contaminated surface in a single application as defined by the U.S. EPA.

[0181] In some embodiments, the cleaning composition remains permanently on the material or surface and can exert antiseptic, disinfectant, and / or sterilizing effects for at least 24 hours, preferably up to 7 days, more preferably up to 14 days, and most preferably 30 days or more, measured from the time of treatment.

[0182] In one embodiment, the method further includes a step of removing the cleaning composition and undesirable and / or harmful microorganisms from the material and / or surface. This step can be achieved, for example, by rinsing or spraying the surface with water and / or scrubbing or wiping the surface with a cloth, wipe, sponge or brush until the cleaning composition and microorganisms are removed from the material and / or surface. Rinsing or spraying with water may be performed before, during, and / or after scrubbing or wiping the surface.

[0183] In some embodiments, a method is provided for preventing spoilage or contamination of consumer products, wherein the surfactant XYZ derivative according to the present invention is applied to or incorporated into the consumer product as a preservative component. Consumer products include, for example, cleaning products, home care products, personal care products, cosmetics, paints and / or building materials, and in some embodiments, pharmaceuticals, supplements, foods and / or beverages.

[0184] Microorganisms targeted for disinfection, sterilization, and / or preservation. The aforementioned method is advantageous in that it can be used for disinfection, sterilization, and / or preservation of a wide range of undesirable and / or harmful microorganisms, including both Gram-negative and Gram-positive bacteria, yeasts, molds, biofilms (including biofilms containing multiple species), enveloped viruses, non-enveloped viruses, white molds, and even algae.

[0185] In certain embodiments, the method can be used for preserving, sterilizing, and / or disinfecting materials and / or surfaces that are susceptible to contamination by unwanted microorganisms. Undesirable microorganisms include, for example, Gram-positive genera such as Bacillus, Alicyclobacillus, Geobacillus, Lactobacillus, Streptococcus, Micrococcus, Pediococcus, Leuconostoc, Oenococcus, Propionibacterium, Streptococcus, Enterococcus, Actinomyces, and Streptomyces; Gram-negative genera such as Erwinia, Corynebacterium, Cyclobacter, Pseudomonas, Alcaligenes, Escherichia, Proteus, Serratia, Citrobacter, Aeromonas, Acinetobacter, and Klebsiella; and various fungal genera such as Saccharomyces, Zygosaccharomyces, Geotricum, Candida, and Penicillium.

[0186] A preferred embodiment of the present invention provides safe disinfectants, bactericides, and preservatives suitable not only for the treatment of agricultural products, fresh foods, processed foods, cosmetics, personal care products, and cleaning products, but also for the treatment of facilities in which these products are manufactured.

[0187] In another specific embodiment, the method can be used to disinfect and / or kill harmful microorganisms known to cause disease or illness in humans, animals and / or plants. Harmful organisms include life-threatening foodborne and waterborne pathogens, such as Campylobacter jejuni, Salmonella tiphimurium, E. coli 0157:H7, Staphylococcus aureus, Yersinia enterocolitica, Clostridium perflingens, Clostridium botulinum, Bacillus cereus, Bacillus subtilis, Escherichia coli, Xanthomonas campestris, Listeria monocytogenes, Enterococcus faecalis, Klebsiella pneumoniae and Enterobacter aerogenes.

[0188] Furthermore, the present invention can be used to control and prevent infectious pathogens that pose a serious public health concern. Such pathogens include, for example, bacteria such as Salmonella enterica, Salmonella cholera suis, Staphylococcus aureus (including MRSA), Staphylococcus saprophyticus, Streptococcus pyogenes, Streptococcus pneumoniae, Bacillus ancillasis, Legionella pneumophila, Klebsiella pneumoniae, Sigella decenteriae, Vibrio cholera, Vibrio parahemorrhagicus, vancomycin-resistant enterococci, Mycobacterium tuberculosis, Mycobacterium bovis, Acinetobacter baumannii, and Clostridium difficile;

[0189] For example, fungi such as Zygosaccharomyces, Devariomyces hansenii, Candida, Deckera / Brettanomyces, Leptosferlina shaltarum, Epicoccum nigricum, Wallemia sebi, Cryptococcus, Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton phlocosum (including pathogens such as Candida albicans, Candida auris, and Mucor miehei);

[0190] For example, fungi of the genera Alternaria, Aspergillus, Bisochlamis, Botrytis, Cladosporium, Fusarium, Geotrichum, Manoscus, Monilia, Mortierella, Mucor, Neurospora, Oidium, Oospora, Penicillium, and others; as well

[0191] Examples of parasitic organisms include tapeworms, helminths, nematodes, genera such as Toxoplasma, Trikinella, Giardia lambira, Enteramoeba historica, and Cryptosporidium.

[0192] In certain embodiments, the cleaning composition may exhibit disinfectant and / or bactericidal activity against enveloped viruses and non-enveloped viruses such as coronaviruses (including SARS-CoV1 and CoV2), rotavirus, norovirus, hepatitis A virus, hepatitis B virus, hepatitis C virus, coxsackievirus, rhinovirus, common cold viruses, influenza viruses, herpesviruses, cytomegalovirus, and poliovirus.

[0193] Conditioning composition and method of use The present invention provides conditioning compositions and methods for using them in conditioning hair, fibers, and textile products. More specifically, the present invention provides microorganism-derived components for use in formulating hair care products, household laundry products, and textile processing materials. In certain embodiments, these microorganism-derived components are advantageous because they are useful as a substitute for and / or reduce the use of conventional conditioning compounds such as QAC and palm oil.

[0194] In this specification, the term “conditioning” means, when applied to hair, fibers and / or textile products, one or more of the following non-limiting examples: suppression of static electricity and / or frizz; improvement of strength; suppression of breakage; suppression of tangling and knotting; improvement of shine and flexibility; improvement of oil and / or moisture retention; reduction of wrinkles; and / or imparting of fragrance.

[0195] In some embodiments, the conditioning composition can be used in hair care products such as shampoos, conditioners or cream rinses, detanglers or styling products. In some embodiments, the conditioning composition can be used in household or industrial laundry products such as fabric softeners or dryer sheets. In some embodiments, the conditioning composition can be used for conditioning raw fibers or fabrics before they become clothing, fabrics, rugs or other textile products.

[0196] In a preferred embodiment, the conditioning composition comprises one or more XYZ surfactants according to the present invention. The XYZ surfactants may be present in amounts of about 100 ppm to about 250,000 ppm, about 200 ppm to about 100,000 ppm, about 300 ppm to about 75,000 ppm, about 400 ppm to about 50,000 ppm, or about 500 ppm to about 25,000 ppm.

[0197] In certain embodiments, the conditioning composition contains XYZ surfactants in amounts of about 0.01% to about 25% by weight, about 0.05% to about 20% by weight, about 0.1% to about 15% by weight, or about 0.5% to about 10% by weight.

[0198] In certain embodiments, the conditioning composition may further contain additional biosurfactants. For example, in some embodiments, the conditioning composition comprises a linear cationic SLP derivative and one or more other SLP molecules that have not been derivatized according to the present invention.

[0199] In certain embodiments, the one or more biosurfactants include, for example, glycolipids selected from sophorolipids (SLP), mannosylerythritol lipids (MEL), rhamnolipids (RLP), and trehalose lipids (TL). The biosurfactants may be derivatized or in their natural state.

[0200] In some embodiments, the biosurfactant is used in crude form. In this case, the biosurfactant molecule is present in the growth medium (e.g., broth) in which the biosurfactant-producing microorganism is cultured and is recovered from the growth medium without purification. In crude form, the proportion of amphiphilic molecules in the growth medium may be, for example, at least 0.001%, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In another embodiment, the biosurfactant is extracted from the growth medium and may optionally be further derivatized and / or purified.

[0201] The mixing ratio of cationic SLP derivatives to non-derivativeized SLPs may be in the range of 1:1 to 1:1000, 1:5 to 1:500, or 1:10 to 1:100.

[0202] In other embodiments, the conditioning composition comprises a linear cationic SLP derivative and one or more mannosylerythritol lipid (MEL) molecules.

[0203] The mixing ratio of cationic SLP derivatives to MEL may be in the range of 1:1 to 1:1000, 1:5 to 1:500, 1:10 to 1:100, 1000:1 to 1:1, 500:1 to 5:1, or 100:1 to 10:1.

[0204] In yet another exemplary embodiment, the conditioning composition comprises a derivatized linear cationic SLP, one or more other SLP molecules, and one or more MEL molecules.

[0205] In one embodiment, MEL comprises 4-OBD-mannopyranosylmesoerythritol or 1-OBD-mannopyranosylmesoerythritol as a hydrophilic moiety and a fatty acid group and / or an acetyl group as a hydrophobic moiety. One or two of the hydroxyl groups may be acetylated, and these hydroxyl groups are typically located at C4 and / or C6 of the mannose residue. Furthermore, there may be one to three esterified fatty acids with a chain length of 8 to 12 or more carbon atoms.

[0206] MEL and MEL-like substances (e.g., mannose-based substances) are mainly produced by the genera Pseudozyma (e.g., Pseudozyma afidis) and Ustirago (e.g., Ustirago meidis), and the MEL structures produced by each fungal species are highly diverse. Certain mannose-based substances with properties similar to MEL can also be produced by the yeast Meyerozyma gilliermondi.

[0207] MEL is non-toxic and stable over a wide temperature and pH range. Furthermore, MEL can be used without the addition of preservatives.

[0208] MELs are primarily classified into five categories: MEL A, MEL B, MEL D, triacetylated MEL A, and triacetylated MEL B / C, resulting in over 93 different combinations. These molecules may be modified synthetically or naturally. For example, MELs may differ in carbon chain length or the number of acetyl groups and / or fatty acid groups.

[0209] The MEL molecules and / or modified forms thereof according to the present invention include, for example, triacylated MEL, diacylated MEL, monoacylated MEL, triacetylated MEL, diacetylated MEL, monoacetylated MEL, nonacetylated MEL, and their stereoisomers and / or structural isomers.

[0210] In the present invention, other mannose-based / MEL-like substances exhibiting similar structures and properties may also be used, such as mannosylmannitol lipids (MML), mannosylarabitol lipids (MAL), and / or mannosylribitol lipids (MRL).

[0211] In certain embodiments, the composition includes a carrier. Non-limiting examples of carriers include water; saline solution; physiological saline solution; ointments; creams; oil-water emulsions; water-in-oil emulsions; silicone-in-water emulsions; water-in-silicone emulsions; wax-in-water emulsions; water-oil-water triple emulsions; microemulsions; gels; vegetable oils; mineral oils; ester oils such as octyl palmitate, isopropyl myristate, and isopropyl palmitate; ethers such as dicapryl ether and dimethyl isosorbide; alcohols such as ethanol and isopropanol; fatty alcohols such as cetyl alcohol, cetearyl alcohol, stearyl alcohol, and behenyl alcohol; and isooctane, isododecane (IDD), and isohexadecane. Examples include soparaffins; silicone oils such as cyclomethicone, dimethicone, dimethicone crosslinked polymers, polysiloxanes and their derivatives (preferably organically modified derivatives including PDMS, dimethicone copolyol, dimethiconol, amodimethiconol, etc.); hydrocarbon oils such as mineral oil, petrolatum, isoeicosane, and polyolefins (e.g., (hydrogenated) polyisobutene); polyols such as propylene glycol, glycerin, butylene glycol, pentylene glycol, hexylene glycol, and caprylyl glycol; waxes such as beeswax, carnauba wax, ozokerite, microcrystalline wax, polyethylene wax, and vegetable wax; or any combination or mixture thereof. The aqueous medium may contain one or more water-miscible solvents, for example, lower alcohols such as ethanol and isopropanol. The proportion of aqueous media may be about 1% to about 99% by weight, 10% to about 85% by weight, 25% to about 75% by weight, or 50% to about 65% by weight of the composition.

[0212] Optionally, the conditioning composition may further contain one or more other ingredients relevant to a particular use. Examples include organic solvents and / or inorganic solvents, organic acids and / or inorganic acids, essential oils, plant extracts, crosslinking agents, chelating agents, fatty acids, alcohols, pH adjusters, reducing agents, buffering agents, enzymes, dyes, colorants, fragrances, preservatives, emulsifiers, deemulsifiers, foaming agents, defoaming agents, bleaching agents, emollients, humectants, anti-inflammatory agents, polymers, stabilizers, silicones, thickeners, softeners, UV blockers, moisturizers, film-forming agents, minerals, vitamins, proteins, viscosity modifiers, and Examples include rheological modifiers, insect repellents, skin cooling compounds, skin protectants, lubricants, pearls, Chromalight, mica, anti-allergic agents, antimicrobial agents (e.g., antifungal, antiviral, antibacterial agents), disinfectants, pharmaceuticals, light stabilizers, surface smoothers, light diffusing agents, exfoliation accelerators, antistatic agents, wrinkle inhibitors, wetting agents, dye transfer aids, color protectants, deodorants, odor capture agents, detergents, drying agents, water repellents, anti-pilling agents, acidifying agents, sizing agents, fluorescent whitening agents, antioxidants, shrinkage inhibitors, starches, and mixtures thereof.

[0213] The content of each component, whether active or inactive, shall be in amounts typically used to achieve their respective purposes in cosmetics / personal care, textile processing, and laundry care, and is generally in the range of about 0.0001% to about 25%, or about 0.001% to about 20%, of the composition, but may be outside this range. The properties and content of these components shall be suitable for the manufacture and function of the compositions of this disclosure. In preferred embodiments, the composition includes additives that are considered dermatologically acceptable.

[0214] In this specification, “dermatologically acceptable,” “cosmetic acceptable,” and “topically acceptable” are used interchangeably, meaning that a particular ingredient is safe and non-toxic when applied to the external skin (e.g., skin, scalp) at the concentrations used. In one embodiment, the ingredients contained in the composition are understood to be generally recognized as safe (GRAS).

[0215] In certain embodiments, the composition may contain pH adjusters (e.g., citric acid, ethanolamine, sodium hydroxide, etc.) to be formulated at a wide range of pH levels. In one embodiment, the pH of the conditioning composition is in the range of 1.0 to 13.0. In some embodiments, the pH of the conditioning composition is in the range of 2.0 to 12.0. In some embodiments, the pH of the conditioning composition is in the range of 3.0 to 7.0 or 3.0 to 8.0.

[0216] The present invention can take any number of forms. Possible forms include, for example, liquids; colloidal dispersions; microemulsions or nanoemulsions; gels; serums; granular powders, spray-dried powders or dry mixed powders; solid bars; concentrates; encapsulated soluble pods; suspensions; hydrogels; multiphase solutions; vesicle dispersions; foams; mousses; sprays; aerosols; liquid cakes; ointments; essences; pastes; tablets; water-soluble sheets or sachets, and / or impregnated onto dry or wet substrates such as sheets (e.g., dryer sheets), balls (e.g., wool dryer balls), cloths, sponges or wipes.

[0217] Conditioning methods for hair, fibers, and textile products In a preferred embodiment, the present invention further provides a method for conditioning hair, fibers, or textile products, comprising the step of bringing a conditioning composition of the present invention into contact with the hair, fibers, or textile products for an effective time to impart a conditioning effect. In some embodiments, the conditioning composition is applied together with water or other solvent. In some embodiments, the composition is rinsed off after contact with the hair, fibers, or textile products.

[0218] With respect to hair conditioners, the method may include a step of bringing the composition into contact with the hair. In some embodiments, the composition is brought into contact with wet hair, while in other embodiments, the composition is brought into contact with dry hair. Methods of applying the conditioning composition include lathering the composition and massaging it directly into the hair, spraying the composition onto the hair, applying the composition to the hair while combing, and / or other standard methods of applying hair care products.

[0219] In certain embodiments, the composition is applied to the hair at the same time as shampooing or after shampooing (i.e., after washing and rinsing). The conditioning composition may be left on the hair as a leave-in conditioning treatment, or it may be rinsed off after being in contact for, for example, at least 15 seconds, at least 30 seconds, at least 1 minute, at least 5 minutes, or at least 60 minutes.

[0220] With regard to textile conditioners, the composition may be brought into contact with fibers used in the manufacture of clothing and other textile products. In certain embodiments, the composition is brought into contact with fibers before they become textile products.

[0221] Chemical surfactants are often used for scouring, or washing, raw fibers before further processing. Since scouring can dry out the fibers, conditioning or lubrication treatment is necessary before spinning, twisting, and weaving the fibers to produce textile products. Therefore, in certain embodiments, contacting the fibers with a conditioning composition can improve their slipperiness and soften them, thereby suppressing breakage, drying, static charge, and / or stiffness after scouring.

[0222] With regard to the conditioning of textile products, the above method can also be used in the finishing stages of textile product manufacturing, and further, it can be used for household and industrial laundry. For example, in some embodiments, the conditioning composition is used in the form of a fabric softener applied to clothing or other textile products during a standard wash or dry cycle, or in the form of a spray applied to wet or dry textile products. [Examples]

[0223] Understanding the present invention and its many advantages will be further enhanced by the following examples, which are presented as illustrations of some of the methods, uses, embodiments, and modifications of the present invention. These examples should not be construed as limiting the present invention. Numerous modifications and variations are possible with respect to the present invention.

[0224] Example 1 - Aliphatic amino alcohol surfactant In certain embodiments, the derivatized surfactant compound is an aliphatic amino alcohol surfactant particularly useful as an emulsifier, emollient, and / or wetting agent. Furthermore, these surfactants have a primary or tertiary alcohol, which can be further modified by introducing an alkoxyl group to increase its molecular weight.

[0225] Aliphatic amino alcohol surfactants XYZ can be prepared by arbitrarily combining reagents X' and Z' with an aliphatic amino acid alkyl ester reagent Y' (Table 2).

[0226] [Table 2]

[0227] Formula (A) shown below is produced using X' = dodecanoyl chloride, Y' = alanine ethyl ester, and Z' = LAH.

[0228] [Chemical]

[0229] The formula (B) exemplified below is produced using X' = dodecanoyl chloride, Y' = methionine ethyl ester, and Z' = LAH.

[0230] [Chemical]

[0231] By further oxidizing formula (B), a sulfone group Y is generated, and a derivatized surfactant compound (C) can be produced. This compound is particularly useful as an emulsifier, skin softener, wetting agent, surfactant and / or chelating agent.

[0232] [Chemical]

[0233] Example 2 - Amido Amino Alcohol Surfactant In certain embodiments, the derivatized surfactant compound of the present invention is an amido amino alcohol surfactant that is particularly useful as an emulsifier, skin softener, wetting agent, surfactant and / or chelating agent. The amido amino alcohol surfactant XYZ can be produced by arbitrarily combining an X' reagent and a Z' reagent with an amide-containing amino acid alkyl ester Y' reagent (Table 3).

[0234] [Table 3]

[0235] The formula (D) exemplified below is produced using X' = dodecanoyl chloride, Y' = glutamine ethyl ester, and Z' = LAH.

[0236] (#ID=50]] [Chemical]

[0237] Example 3 - Aromatic amino alcohol surfactant In certain embodiments, the derivatized surfactant compound is an aromatic amino alcohol surfactant particularly useful as an emulsifier, emollient, wetting agent, and / or surfactant. Furthermore, these surfactants have a primary or tertiary alcohol, which can be further modified by introducing an alkoxyl group to increase its molecular weight.

[0238] Aromatic amino alcohol surfactants XYZ can be prepared by arbitrarily combining reagents X' and Z' with aromatic amino acid alkyl ester reagent Y' (Table 4).

[0239] [Table 4]

[0240] Formula (E) shown below is produced using X' = dodecanoyl chloride, Y' = phenylalanine ethyl ester, and Z' = LAH.

[0241] [ka]

[0242] Example 4 - Cationic amino alcohol surfactant In certain embodiments, the derivatized surfactant compounds are cationic amino alcohol surfactants particularly useful as antimicrobial agents, preservatives, and / or conditioners for hair / textile products. Furthermore, these surfactants may contain a primary or tertiary alcohol, to which an alkoxyl group may be introduced to increase the molecular weight.

[0243] The cationic amino alcohol surfactant XYZ can be produced by arbitrarily combining X' reagent and Z' reagent with a cationic amino acid alkyl ester Y' reagent (Table 5).

[0244]

Table 5

[0245] The formula (F) exemplified below is produced using X' = dodecanoyl chloride, Y' = arginine ethyl ester, and Z' = LAH.

[0246]

Chemical formula

[0247] Example 5 - Diol amino alcohol surfactant In certain embodiments, the derivatized surfactant compounds are alcoholic diol amino surfactants that are particularly useful as emulsifiers, skin softeners, wetting agents and / or surfactants. Further, these surfactants have primary alcohols and / or tertiary alcohols into which an alkoxyl group can be further introduced to increase the molecular weight. The alcoholic diol amino surfactant, unlike other surfactants described herein, can introduce an alkoxyl group at two different positions: an alcohol as the backbone and an alcohol as the side chain.

[0248] The alcoholic diol amino surfactant XYZ can be produced by arbitrarily combining X' reagent and Z' reagent with a hydroxyl amino acid alkyl ester Y' reagent selected from tyrosine ethyl ester, threonine ethyl ester and serine ethyl ester (Table 6).

[0249]

Table 6

[0250] Formula (G) shown below is produced using X' = dodecanoyl chloride, Y' = threonine ethyl ester, and Z' = LAH.

[0251] [ka]

[0252] Furthermore, the alcoholic diolamino surfactant XYZ can also be prepared by optionally combining reagents X' and Z' with reagent Y', which is diethyl aspartate and diethyl glutamate (Table 6). In some embodiments, when Y' contains diethyl aspartate or diethyl glutamate, the side chain carbonyl is also reduced by treatment with Z'.

[0253] Formula (H) shown below is produced using X' = dodecanoyl chloride, Y' = diethyl glutamate, and Z' = LAH.

[0254] [ka]

[0255] Example 6 - Sulfonic acid amino alcohol surfactant In certain embodiments, the derivatized surfactant compound is a sulfonic acid amino alcohol surfactant. These surfactants further contain a primary or tertiary alcohol, which can have its molecular weight increased by introducing an alkoxyl group.

[0256] The sulfonic acid amino alcohol surfactant XYZ can be prepared by arbitrarily combining reagents X' and Z' with the sulfur-containing amino acid alkyl ester reagent Y' (Table 7).

[0257] [Table 7]

[0258] Formula (I), shown below as an example, is prepared using X' = dodecanoyl chloride, Y' = disysteine ​​ethyl ester, and Z' = LAH.

[0259] [ka]

[0260] This formulation is particularly useful as an emulsifier, emollient, humectant, and / or chelating agent.

[0261] Formula (J), shown below as an example, is prepared using X' = dodecanoyl chloride, Y' = cysteine ​​ethyl ester, and Z' = LAH.

[0262] [ka]

[0263] By further oxidizing the thiol group of formula (J), formula (K) having a sulfonic acid Y group can be produced. This derivatized surfactant compound is particularly useful as an emulsifier, emollient, wetting agent, surfactant, chelating agent, and / or foaming agent. In the case of formula (I), a similar chemical reaction can be applied to the resulting disulfide. Specifically, the disulfide is first reduced to a thiol, or the disulfide is directly oxidized to a sulfonic acid.

[0264] [ka]

[0265] Example 7 - Microbial sterilization test protocol Tests were conducted to investigate the antibacterial activity of a surfactant derivatized with cationic arginine, manufactured according to embodiments of the present invention.

[0266] The test organisms consisted of a mixture of Gram-negative and Gram-positive bacteria. Using these, the broad control spectrum of the technology and its effectiveness against common pathogens of public health concern, namely Pseudomonas aeruginosa (Gram-negative), Staphylococcus aureus (Gram-positive), and Salmonella (Gram-negative), were verified.

[0267] After growing the test bacteria in tryptic soy broth at 32°C for 24-48 hours, the starting concentration was 10 7 The sample was plated. It was then diluted with PBS to achieve the desired bacterial cell concentration.

[0268] Stock solutions for each antimicrobial agent treatment were prepared as aqueous solutions, and using these, the prescribed dilutions for treatment (25 ppm, 50 ppm, 200 ppm, 400 ppm, 500 ppm, 750 ppm, 1,000 ppm, 1,500 ppm, 2,000 ppm, and 4,000 ppm) were prepared by adding an appropriate amount of buffer solution. The buffer solution contained 100 mM citrate, ammonium HCl, PBS, or sodium bicarbonate.

[0269] Prepared bacterial cell dilution (10 7 The CFU / mL was mixed with 100 μL to 900 μL of an appropriate PPM value of antimicrobial agent, or 1 to 9 mL of an appropriate PPM value of antimicrobial agent. The final concentration of the target organism at the time of mixing with the antimicrobial agent was 10 6 That was the case.

[0270] When the target organism was added to the antimicrobial agent, a timer set to a predetermined time (0, 2, 5, 6, or 10 minutes) was started. When the timer finished, the antimicrobial agent was neutralized, and each dilution was plated onto a TSA plate and incubated at 32°C for 24 to 48 hours.

[0271] As a negative control, 0.1 mL of the target organism stock solution was plated onto a TSA plate. As a positive control, serial dilutions prepared with 400 PPM of quaternary ammonium compound (QAC) as the starting concentration, along with the target organism, were prepared. 2 , 10 3 and 104 The samples were plated at concentrations of CFU / mL.

[0272] After incubation for 24-48 hours, the plates were removed from the incubator and the number of colonies was counted.

[0273] The following scales are generally used to determine the effectiveness of a compound. For disinfection, a logarithmic reduction of 6 times or more (≧6log) in less than 10 minutes is required. TIFF2026510299000042.tif56166

[0274] Example 8 - Comparison of surface tension reduction and logarithmic decrease value Table 8 summarizes the decrease in surface tension at 1,000 ppm and the logarithmic decrease in Pseudomonas aeruginosa at 0 and 10 minutes. (200 ppm) Two C12 cationic amino alcohol surfactants, LRO(R) and LKO(K), according to embodiments of the present invention. LRO was produced by coupling a lauroyl chloride substrate with arginine ethyl ester, and LKO was produced by coupling a lauroyl chloride substrate with lysine ethyl ester.

[0275] [Table 8]

[0276] Table 9 summarizes the decrease in surface tension at 1,000 ppm and the logarithmic decrease in Staphylococcus aureus and Salmonella at 0 and 10 minutes. (200 ppm) Cationic amino alcohol surfactants classified into four types according to embodiments of the present invention.

[0277] These surfactants were produced by coupling octanoyl chloride (C8), decanoyl chloride (C10), lauroyl chloride (C12), myristiroyl chloride (C14), palmitoyl chloride (C16), or linear sophorolipids (SLP) with arginine ethyl ester (R), histidine ethyl ester (H), or lysine ethyl ester (K).

[0278] [Table 9]

[0279] Example 9 - Stability Test Tables 10 and 11 summarize the pH stability of LAE(RE) and LRO(RO), a C12 cationic amino alcohol surfactant according to an embodiment of the present invention, compared over four days. LRO was produced by coupling a lauroyl chloride substrate with arginine ethyl ester. The logarithmic decrease value was determined according to the method described in Example 7 above. Table 12 shows the activity decrease rates of LRO and LAE at pH 7.

[0280] [Table 10]

[0281] [Table 11]

[0282] [Table 12]

[0283] References Czakaj, A. et al. (2021). Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System. Molecules. 26, 5894. https: / / doi.org / 10.3390 / molecules26195894 (“Czakaj et al. 2021”).

Claims

1. The following general formula: 【Chemistry 1】 (wherein X is a C2-C22 fatty acid amide derived from a fatty acid or a biosurfactant containing a fatty acid portion, Y contains a functional group derived from an amino acid, and Z １ and Z ２ A derivatized surfactant compound having (each independently being hydrogen or an alkyl group).

2. The compound of claim 1, wherein X is derived from lauroyl chloride, octanoyl chloride, decanoyl chloride, dodecanoyl chloride, myristiroyl chloride, palmitoyl chloride, and behenoyl chloride.

3. The compound according to claim 1, wherein X is derived from a sophorolipid-based biosurfactant.

4. X, 【Chemistry 2】 【Transformation 3】 or 【Chemistry 4】 The compound according to claim 1.

5. The compound according to claim 1, wherein one or more functional groups derived from amino acids in Y are amino alcohols or amino acid alkyl esters.

6. The compound of claim 5, wherein the amino acid alkyl ester is alanine ethyl ester, glycine ethyl ester, methionine ethyl ester, valine ethyl ester, leucine ethyl ester, isoleucine ethyl ester, proline ethyl ester, glutamine ethyl ester, asparagine ethyl ester, phenylalanine ethyl ester, tryptophan ethyl ester, lysine ethyl ester, arginine ethyl ester, homoarginine ethyl ester, histidine ethyl ester, tyrosine ethyl ester, threonine ethyl ester, serine ethyl ester, taurine ethyl ester, aspartate diethyl, glutamate diethyl, cysteine ​​ethyl ester, or discysteine ​​ethyl ester.

7. The following structure: 【Transformation 5】 (wherein X is a C2-C22 fatty acid amide derived from a fatty acid or a biosurfactant containing a fatty acid portion, Y contains a functional group derived from an amino acid, and Z １ and Z ２ A method for producing a derivatized surfactant compound having stability at pH 2 to 12, wherein each of the elements is independently hydrogen or an alkyl group, A step of coupling a substrate X' containing a biosurfactant or a fatty acid with an amide Y' containing one or more amino acid side chains to obtain a surfactant XY into which an amino acid functional group has been introduced. The process involves reacting Y' or XY with a reducing agent Z' before, during, or after coupling to obtain XY, thereby reducing any ester groups present in Y' or XY to alcohols. A method that includes this.

8. The method of claim 7, wherein X' is an acyl halide.

9. The method of claim 8, wherein the acyl halide is lauroyl chloride, octanoyl chloride, decanoyl chloride, dodecanoyl chloride, myristiroyl chloride, palmitoyl chloride, or behenoyl chloride.

10. The method of claim 7, wherein the one or more amino acid-derived functional groups in Y' are amino alcohol, alanine ethyl ester, glycine ethyl ester, methionine ethyl ester, valine ethyl ester, leucine ethyl ester, isoleucine ethyl ester, proline ethyl ester, glutamine ethyl ester, asparagine ethyl ester, phenylalanine ethyl ester, tryptophan ethyl ester, lysine ethyl ester, arginine ethyl ester, homoarginine ethyl ester, histidine ethyl ester, tyrosine ethyl ester, threonine ethyl ester, serine ethyl ester, taurine ethyl ester, aspartate diethyl, glutamate diethyl, cysteine ​​ethyl ester and / or discysteine ​​ethyl ester.

11. The method of claim 7, wherein X' is a sophorolipid (SLP)-based biosurfactant.

12. The method of claim 11, wherein the SLP is a linear SLP molecule having a C18 carboxylic acid terminus containing one unsaturated bond, and the method comprises the steps of obtaining a carboxylic acid terminus cleaved at position 9 by utilizing oxidative cleavage, and obtaining a short-chain SLP amide by introducing an amide containing one or more amino acid functional groups to the cleaved carboxylic acid terminus.

13. The method of claim 7, wherein Z' is lithium aluminum hydride; methylmagnesium bromide; ethylmagnesium bromide; methylphenylmagnesium bromide; phenylmagnesium bromide; n-butyllithium; or sec-butyllithium.

14. The method of claim 7, wherein the coupling of X' and Y' is carried out using a coupling agent selected from one or more of the following: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI / HOBt), benzotriazole-1-yloxytripyrrolidinophosphonium hexafluorophosphonium (PYBOP), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), and N,N'-dicyclohexylcarbodiimide / 1-hydroxybenzotriazole (DCC / HOBt).

15. A consumer product comprising a derivatized surfactant according to any one of claims 1 to 6, having a pH of 2 to 12, and being a cleaning product, a home care product, a personal care product, a cosmetic, a paint and / or building material, a health product, a food or beverage.

16. A method for improving the pH stability of an amino acid ethyl ester, comprising the step of converting the amino acid ethyl ester to an amino alcohol.

17. The method of claim 16, wherein the amino alcohol is stable at a pH of 2 to 12.

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