Surfactants for cleaning products

Abstract

Surfactants for use in detergent, blowing agent, emulsifier and degreaser formulations. Some aspects of the present disclosure include formulations suitable for cleaning and / or conditioning fabrics including upholstery. Some formulations are suitable for household or commercial dry cleaning. Some formulations may be suitable for cleaning hard surfaces, including plastic surfaces and surfaces in contact with food products. Certain other formulations may be suitable for cleaning surfaces used in food processing, food items themselves, and health care institutions.

Description

[0001] Cross-reference to related applications This application claims priority to U.S. Patent Application No. 18 / 795,170, filed August 5, 2024, and to U.S. Provisional Patent Application Serial No. 63 / 531,198, filed August 7, 2023, the entire disclosure of which is incorporated herein by reference.

[0002] field This disclosure relates to surfactants for use in cleaning products, including cleaning products for cleaning and conditioning fabrics, hard surfaces, and plastic surfaces. Such surfactants may include siloxane derivatives of amino acids, wherein the siloxane derivatives have surface-active properties. Background Technology

[0003] Surfactants (molecules with surface-active properties) are widely used in commercial applications, ranging from detergents and hair care products to cosmetics. Compounds with surface-active properties are used as soaps, detergents, lubricants, wetting agents, foaming agents, and spreading agents. In personal care and cleaning products (such as shampoos, body washes, facial cleansers, liquid handmade soaps, etc.), surfactants are often the most important component because they provide many of the cleaning properties of the composition.

[0004] Surfactants can be uncharged, amphoteric, cationic, or anionic. Although in principle any class of surfactant (e.g., cationic, anionic, nonionic, amphoteric) is suitable for cleaning or sanitation applications, in practice many personal care cleaners and household cleaning products are formulated with a combination of two or more surfactants (from two or more surfactant classes).

[0005] Typically, surfactants are amphiphilic molecules having a relatively water-insoluble hydrophobic "tail" group and a relatively water-soluble hydrophilic "head" group. These compounds can adsorb at interfaces (e.g., between two liquids, a liquid and a gas, or a liquid and a solid). In systems containing relatively polar and relatively nonpolar components, the hydrophobic tail typically and selectively interacts with (one or more) of the relatively nonpolar component, while the hydrophilic head selectively interacts with (one or more) of the relatively polar component. In the case of a water-oil interface, the hydrophilic head group extends into the water, while the hydrophobic tail extends into the oil. When added to a water-air interface only, the hydrophilic head group extends into the water, while the hydrophobic tail extends into the air. The presence of a surfactant disrupts at least some of the intermolecular interactions between water molecules, replacing at least some of the normally weaker interactions between water molecules and the surfactant. This results in reduced surface tension and can also be used to stabilize the interface.

[0006] At sufficiently high concentrations, surfactants can form aggregates that confine the hydrophobic tails to the polar solvent. One such aggregate is a micelle. In a typical micelle, molecules are arranged in spheres, with the hydrophobic tails of one or more surfactants typically located inside the spheres, and the hydrophilic heads of one or more surfactants located on the outside of the micelle, where the heads interact with the more polar solvent. The effect of a given compound on surface tension and its concentration at which it forms micelles can be used as defining characteristics of a surfactant. Summary of the Invention

[0007] This disclosure provides compositions for cleaning and / or degreasing the following: hard and plastic surfaces such as floors, walls, ceilings, roofs, countertops, furniture, plates, cups, glasses, tableware, eating utensils, machines, machine parts, and apparatus for preparing and / or packaging food; fabric care preparations including laundry detergents, stain removers, washing pretreatment agents, fabric softeners, fabric dyes, and bleaches; and for cleaning interior furnishings and carpets. Some compositions of the invention may be in the form of detergents, emulsifiers, dispersants, foaming agents, and combinations thereof. Products of the invention may be formulated to include one or more surfactants derived from one or more surfactant classes.

[0008] This disclosure provides siloxane derivatives of amino acids with surface-active properties. The amino acids can be naturally occurring or synthetic, or they can be obtained via a ring-opening reaction of a molecule such as a lactam (e.g., caprolactam). The amino acid can be functionalized with different types of siloxane groups to form compounds with surface-active properties. Characteristically, these compounds may have a low critical micelle concentration (CMC) and / or the ability to reduce the surface tension of liquids.

[0009] This disclosure provides formulations for cleaning that comprise one or more surfactant molecules having a structure of formula I or II, and optionally one or more soaps that can be characterized as surfactants themselves. The soaps may also comprise fatty acids and salts, and some soaps may contain both water-soluble and fat-soluble portions. Among them, R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0010] For clarity, as disclosed herein, and with respect to any formulation provided herein, the molecule of Formula II may represent a structure with the following configuration: Formula I - Connector - Formula I, One molecule of Formula I may be the same as or different from another molecule of Formula I. In this exemplary structure, the linker is R in Formula I. 3 C1-C 12 Connector.

[0011] The other surfactant molecules provided in this disclosure are those compounds of formula I or II, wherein R 1 and R 2 It is a methyl group.

[0012] Other surfactant molecules provided in this disclosure are compounds of formula I or II, wherein n and / or z is 5.

[0013] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0014] More specifically, R 3 You can choose from the following formula: .

[0015] The use of compounds of formula I or II as surfactants as described herein in cleaning formulations is also disclosed.

[0016] This disclosure also provides a cleaning formulation comprising one or more surfactant molecules having a structure of formula I or II, and at least one builder, which may include molecules that enhance cleaning efficacy in an aqueous environment. Some useful builder includes, but is not limited to, certain polymers, phosphates and aluminosilicates, calcium citrate, alkali metal salts, sodium salts, and certain grades of zeolites. Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0017] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0018] More specifically, R 3 You can choose from the following formula: .

[0019] The use of compounds of formula I or II as described herein as surfactants in cleaning formulations, which also contain detergent builders as described herein, is also disclosed.

[0020] This disclosure also provides formulations for cleaning, comprising one or more surfactant molecules having a structure of formula I or II, and bleaching agents, such as peroxide-based bleaching agents, including but not limited to inorganic peracids, organic peroxyacids, metal borates, percarbonates, superphosphates, persilicates, and persulfates. Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0021] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0022] More specifically, R 3 You can choose from the following formula: .

[0023] The use of compounds of formula I or II as described herein as surfactants in cleaning formulations that further comprise bleach as described herein is also disclosed.

[0024] This disclosure also provides formulations for cleaning, comprising one or more surfactant molecules having a structure of formula I or II, and one or more solvents, and optionally a co-solvent, or a non-flammable oil impregnation composition, for use in one or both of household or commercial dry cleaning methods: Where R 1 and R 2They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0025] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0026] More specifically, R 3 You can choose from the following formula: .

[0027] The use of compounds of formula I or II as described herein as surfactants in cleaning formulations that further comprise solvents as described herein is also disclosed.

[0028] This disclosure also provides certain cleaning compositions that can be used to clean various types of surfaces, not limited to hard surfaces, etc., comprising one or more surfactants described herein, wherein the one or more surfactants impart antimicrobial activity to such surfaces. In other words, the surfactants of this disclosure can impart antimicrobial activity to formulations, even in the absence of other antimicrobial additives and reagents.

[0029] The above and other features of this disclosure, and the ways in which they are obtained, will become more apparent and better understood by referring to the following description of embodiments in conjunction with the accompanying drawings. Attached Figure Description

[0030] Figure 1 A graph showing the surface tension versus concentration of surfactant 1 as described in Example 2b is displayed.

[0031] Figure 2 The graph shows the surface tension of surfactant 2 as a function of concentration, as described in Example 3b.

[0032] Figure 3 The graph shows the surface tension of surfactant 3 as described in Example 4b versus concentration.

[0033] Figure 4 The graph shows the surface tension versus concentration of surfactant 4 as described in Example 5b.

[0034] Figure 5 A graph showing the surface tension of surfactant 5 as described in Example 6b versus concentration is displayed.

[0035] Figure 6 A graph showing the surface tension versus concentration of surfactant 6 as described in Example 7b is displayed.

[0036] Figure 7 A graph showing the surface tension of surfactant 7 as described in Example 8b versus concentration is displayed.

[0037] Figure 8 A graph showing the surface tension of surfactant 8 as described in Example 9b versus concentration is displayed.

[0038] Figure 9 A graph showing the surface tension of surfactant 9 as described in Example 11b versus concentration is displayed.

[0039] Figure 10 A graph showing the surface tension versus concentration of surfactant 10 as described in Example 10b is displayed.

[0040] Figure 11 A graph showing the surface tension of the surfactant as described in Comparative Example A2 versus concentration is displayed. Detailed Implementation

[0041] As used in this article, the phrase “any range defined between any two of the preceding values” literally means that any range can be selected from any two values ​​listed before such a phrase, regardless of whether those values ​​are in the lower or higher part of the list. For example, one can select a pair of values ​​from two lower values, two higher values, or a lower and a higher value.

[0042] As used in this article, the term "alkyl" refers to any saturated carbon chain, which can be straight or branched, and can be substituted at any point along the carbon chain. The carbon chain can have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons.

[0043] As used herein, the phrase "surface-active" refers to a compound that can reduce the surface tension of the medium in which it is at least partially dissolved and / or the interfacial tension with other phases, and thus can be at least partially adsorbed at liquid / vapor and / or other interfaces. The term "surfactant" can be applied to such compounds.

[0044] Regarding imprecise terminology, the terms "approximately" and "approximately" may be used interchangeably to refer to a measurement that includes the measured value and also includes any measurement that is reasonably close to the measured value. A measurement that is reasonably close to the measured value deviates from the measured value by a reasonably small amount, as understood and readily determined by one of ordinary skill in the art. Such deviations may be attributed, for example, to measurement errors or minor adjustments made to optimize performance. If it is determined that a person of ordinary skill in the art would not readily determine the value of such a reasonably small difference, the terms "approximately" and "approximately" may be understood to mean adding or subtracting 15% from the value, such as adding or subtracting 15%, adding or subtracting 12%, adding or subtracting 10%, adding or subtracting 9%, adding or subtracting 8%, adding or subtracting 8%, adding or subtracting 7%, adding or subtracting 6%, adding or subtracting 5%, adding or subtracting 4%, adding or subtracting 3%, adding or subtracting 2%, or even adding or subtracting 1%, etc.

[0045] Unless otherwise expressly defined or implicitly used, as used herein, the term "suds" refers to the non-equilibrium dispersion of air bubbles in a relatively small volume of liquid. Terms such as "suds," "foam," and "lather" are used interchangeably within the meaning of this disclosure.

[0046] Unless otherwise expressly defined or implicitly used, as used herein, the term "sudsing profile" refers to a property of a detergent composition that relates to foam characteristics during wash and rinse cycles. The sudsing profile of a detergent composition includes, but is not limited to, the rate at which foam is generated when dissolved in the detergent solution, the volume and retention of foam during a wash cycle, and the volume and disappearance of foam during a rinsing cycle. The sudsing profile may include the Wash Suds Index and the Rinse Suds Index, as specifically defined by the test methods disclosed below in the examples. It may also include additional foam-related parameters, such as foam stability measured during wash cycles, etc.

[0047] Unless otherwise expressly defined or implicitly used, as used herein, the term "fluid" includes liquid, gel, paste, and gaseous product forms.

[0048] Unless otherwise expressly defined or implicitly used, as used herein, the term "liquid" means a liquid having a viscosity of about 1 to about 2000 mPa*s at 25°C and a viscosity of about 20 sec. -1 The shear rate of a liquid fluid.

[0049] Unless otherwise expressly defined or implicitly used, as used herein, the term "dry cleaning composition" is intended to refer to a composition used in a dry cleaning method that includes dry cleaning solvents, any surfactants, and detergents, but excludes the clothing or garments to be cleaned.

[0050] Unless otherwise expressly defined or implicitly used, as used herein, the term "organic dry cleaning solvent" is intended to refer to any non-aqueous solvent that suitably has a liquid phase at 20°C and standard pressure. The term "organic" has its usual meaning as a compound having at least one carbon-hydrogen bond.

[0051] As used herein, the phrase "food product" includes any food substance that, on its own or during processing, manufacturing, and preparation, may require treatment with antimicrobial agents or cleaning agents to remove debris and other substances (including microorganisms and other agents that can adhere to the surface of the food product or the vessel or container used to hold, manufacture, and / or process the food product or composition), and is edible with or without further processing or preparation. Food products include meat (e.g., red meat and pork), seafood, poultry, agricultural products (e.g., fruits and vegetables), eggs, live eggs, egg products, ready-to-eat foods, wheat, seeds, roots, tubers, leaves, stems, grains, flowers, buds, seasonings, or combinations thereof. The term "agricultural product" refers to food products (e.g., fruits and vegetables) and plant or plant-derived materials that are typically uncooked and typically sold unpackaged, and may sometimes be consumed raw. Furthermore, food products can include liquid products consumed as beverages, broths, soups, and / or components used during cooking, processing, and other preparation steps.

[0052] As used herein, the phrase “plant” or “plant product” includes any plant matter or plant-derived substance. Plant products include, but are not limited to, seeds, nuts, kernels, cut flowers, plants or crops grown or stored in greenhouses, houseplants, etc. Plant products may also include certain grains or seeds that can be processed and subsequently converted into other types of food products that can be consumed. Plant products may also include many types of animal feed.

[0053] As used herein, the phrase "meat products" refers to all forms of animal meat, including the animal's carcass, muscle, fat, organs, skin, bones, and body fluids and similar components. Animal meat includes, but is not limited to, the meat of mammals, birds, fish, reptiles, amphibians, snails, clams, crustaceans, other edible substances such as lobster, crab, etc., or other forms of seafood. Forms of animal meat include, for example, whole or part of an animal, alone or in combination with other ingredients. Typical forms include, for example, processed meat such as cured meat, sliced ​​and shaped products, chopped products, finely chopped products, minced meat and products including minced meat, whole products, etc.

[0054] As used herein, the term "poultry" refers to all forms of any bird that is raised, captured, or domesticated for meat or eggs, and includes chickens, turkeys, ostriches, game hen, squabs, guinea fowl, pheasants, quails, ducks, geese, emus, or the like, as well as the eggs of these birds. Poultry includes whole, sliced, processed, cooked, or raw poultry, and encompasses all forms of poultry meat, by-products, and by-products. Poultry meat includes components that form an animal, such as muscle, fat, organs, skin, bones, and body fluids. Forms of animal meat include, for example, whole or partial animal meat, alone or in combination with other ingredients. Typical forms include, for example, processed poultry meat, such as cured poultry meat, sliced ​​and shaped products, chopped products, finely chopped products, and whole products.

[0055] As used herein, the phrase “poultry scrap” refers to any debris, residue, material, dirt, offal, poultry parts, poultry waste, poultry viscera, poultry organs, fragments, or combinations thereof that are removed from or in part from poultry during processing and enter the waste stream.

[0056] As used herein, the phrase "food processing surface" refers to the surface of a tool, machine, equipment, structure, building, or similar object used as a part of food processing, preparation, or storage. Examples of food processing surfaces include food processing or preparation equipment (e.g., slicing, canning, or transport equipment, including sinks), food processing utensils (e.g., dishes, cutlery, washers, and bar glasses), and the surfaces of floors, walls, or fixtures of structures in which food processing takes place. Food processing surfaces are found and used in food spoilage air circulation systems, aseptic packaging sterilization, food refrigerator and cooler cleaners and disinfectants, dishwashing and sterilization, blancher cleaning and sterilization, food packaging materials, cutting board additives, third sterilization tanks, beverage coolers and warmers, meat cooling or blanching water, automatic dishwasher sterilizers, disinfectant gels, cooling towers, food processing antimicrobial garment sprays, and waterless or low-aqueous food preparation lubricants, oils, and rinsing additives. Food processing surfaces can also be found in fermentation tanks and containers where certain processed and / or raw grains and other food products can be transformed and / or converted into other food products through fermentation processes.

[0057] This disclosure provides compositions for cleaning and / or degreasing the following: hard and plastic surfaces such as floors, walls, ceilings, roofs, countertops, furniture, plates, cups, glasses, tableware, eating utensils, machines, machine parts, and apparatus for preparing and / or packaging food; fabric care preparations, including laundry detergents, stain removers, washing pretreatment agents, fabric softeners, fabric dyes, and bleaches; and compositions for cleaning interior furnishings and carpets.

[0058] This disclosure also provides cleaning compositions applicable to applications involving any type of food contact, such as for cleaning surfaces that come into contact with dairy, fruit, vegetable, meat, beverage, and / or other types of products during preparation, storage, and / or production processes. Food products, food product residues, raw ingredients, and other food preparation and / or handling components may need to be removed from processing machines, containers, and / or equipment, as well as transport devices and vehicles. In these applications, there is a growing consumer preference for organically approved / certified and optionally biodegradable products used to maintain cleanliness. For those surfaces involving food contact, it is desirable to limit the presence of certain components that may have undesirable effects if they come into unintentional contact with food, or worse, even if they remain in food in small amounts and may be ingested. Similar considerations can be applied to surfaces that are routinely handled by children, as they are more likely to put their hands in their mouths after touching or otherwise handling such surfaces (e.g., toys, high chairs, tables, cribs, etc.). In some embodiments, the cleaning formulations of this disclosure can be used as disinfectant compositions for articles cleaned using cleaning in situ (CIP) technology. Such compositions may include oxidants, stabilizers, acidifiers, and surfactants, or mixtures thereof.

[0059] I. Water-based cleaning agents for fabric and household care applications Laundry detergents, degreasers, stain removers, and pretreatment compositions may comprise a combination of detergent surfactants, binders, enzymes, and conditioners. Laundry detergent formulations include solids, liquids, powders, strips, sticks, pods, aerosols, and / or gels.

[0060] The laundry detergent compositions disclosed herein can be used in applications such as automatic washing machine washing, semi-automatic machine washing (i.e., machine washing requiring at least one or two manual steps), hand washing, etc. In some embodiments, the detergent compositions are designated for use in hand washing laundry detergent products.

[0061] Laundry detergent compositions can be in any form, namely, liquid; emulsion; paste; gel; spray or foam; solid, such as powder, granules, agglomerates, tablets, sachets and strips; delivered in dual-compartment or multi-compartment containers or sachets; pre-wetted or dry wipes (i.e., liquid detergent compositions combined with nonwoven materials or powder detergent compositions combined with nonwoven materials), which can be activated by water by the consumer; and other homogeneous or multiphase consumer cleaning product forms.

[0062] Some fabric care formulations disclosed herein comprise one or more surfactants, also referred to as surfactant systems. Surfactant systems are included to provide cleaning properties to the composition. A surfactant system comprises at least one surfactant, which may be an amphoteric surfactant, amphoteric surfactant, cationic surfactant, nonionic surfactant, and optionally at least one other surfactant, which may be an amphoteric surfactant, amphoteric surfactant, cationic surfactant, nonionic surfactant, or a combination thereof. Such surfactants should be physically and chemically compatible with the necessary components described herein, or should not otherwise unduly impair the product's stability, appearance, or performance.

[0063] The compositions disclosed herein can be in any suitable physical form, such as granules (powder, pellets, tablets), liquids, pastes, gels, or strips. The detergent compositions can be in granular form. The compositions can be formulated for use as detergents for hand or machine washing.

[0064] Representative, but not limiting, laundry detergent formulations may include combinations of soap, ionic surfactants, nonionic surfactants, optionally a builder system, and optionally other detergent ingredients. A predetermined amount of soap is present in granular form, dry-mixed with the other components, and the soap granules have a defined soap concentration.

[0065] Some useful detergent compositions according to this disclosure exhibit improved solubility properties across a range of water hardness.

[0066] 1. Detergent and / or soap Detergents include anionic, cationic, nonionic, and amphoteric detergents. Soap includes compounds with the following general formula: (RCO2) - )n M n+ In this , R is an alkyl group, M is a metal, and n+ is +1 or +2. Typically, the alkyl group can be a fatty acid moiety, and M can be sodium, lithium, magnesium, calcium, etc.

[0067] The soap according to this disclosure can constitute about 5 to 85% by weight, for example 7 to 60% by weight, or 10 to 35% by weight, of the formulation. The soap can partially constitute a surfactant system comprising about 20 to 50% by weight of the soap. The surfactant system may comprise 30 to 40% by weight of the soap. In an example of an embodiment of this disclosure, 80% to 100% by weight, for example 85 to 95% by weight, of the soap is present in particulate form.

[0068] The currently disclosed laundry detergent compositions may contain soap particles having a soap concentration of at least 75% by weight, based on the weight of the composition.

[0069] In some embodiments of this disclosure, the soap particles have a soap concentration of 80 to 95% by weight, for example, 85 to 90% by weight. The soap particles may include more than 90% by weight of soap, less than 10% by weight of water, and less than 1% by weight of sodium hydroxide.

[0070] Useful soap compounds include, but are not limited to: alkali metal soaps, such as sodium, potassium, ammonium, and substituted ammonium (e.g., monoethanolamine) salts of higher fatty acids containing about 8 to 24 carbon atoms, or any combination thereof.

[0071] In some embodiments of this disclosure, the fatty acid soap has C 10 To C 22 The length of the carbon chain, for example, C 12 To C 20 Suitable fatty acids can be obtained from natural sources, such as plant or animal esters, including palm oil, coconut oil, babassu oil, soybean oil, castor oil, rapeseed oil, sunflower oil, cottonseed oil, tallow, fish oil, lard, and mixtures thereof. Alternatively, fatty acids can be produced through synthetic methods such as the oxidation of petroleum or by hydrogenating carbon monoxide via the Fischer-Tropsch process. Resin acids, such as those found in tallow and rosin, are suitable. Naphthenic acids are also suitable. Sodium and potassium soaps can be prepared by the direct saponification of fats and oils or by the neutralization of free fatty acids prepared in separate manufacturing processes. Particularly useful are sodium and potassium salts of fatty acids derived from coconut oil and tallow, and mixtures thereof, namely sodium tallow soap, sodium coconut oil soap, potassium tallow soap, and potassium coconut oil soap.

[0072] In some embodiments of this disclosure, the fatty acid soap is a laurel soap. For example, Prifac 5908 is a fatty acid derived from Uniqema, which is neutralized with caustic soda. This soap is an example of a fully hardened or saturated laurel soap, which is typically based on coconut oil or palm kernel oil.

[0073] While not strictly necessary, the soap should not stand out from the rest of the formulation. Therefore, it needs to be whitish and more or less rounded, meaning it has an aspect ratio of less than 2. This ensures that the final form of laundry powder flows freely and that the presence of soap particles means it blends in with the rest of the composition.

[0074] In some embodiments, the soap has a particle size of 400 to 1400 µm, for example 500 to 1200 µm.

[0075] In some implementations, soap granules have a bulk density of 400 to 650 g / L, and fully formulated powders have a bulk density of 400 to 900 g / L. Some consumers prefer fabric wash powders containing a major amount of soap because of their good detergency and tendency to leave clothes feeling softer than when washed with powders based on synthetic detergent active compounds. Soap also has environmental advantages as it is fully biodegradable and a natural material derived from renewable raw materials. Saturated sodium soaps have high Krafft temperatures and therefore poor solubility at low temperatures, which is used by some consumers. Certain blends of saturated and unsaturated soaps are known to have much lower Krafft temperatures. However, unsaturated soaps are less stable during storage and are prone to developing foul odors. Therefore, the soap blends used in granules require careful balancing between solubility and stability. When soap is concentrated in granules, its stability is enhanced compared to soap incorporated into composite granules at low concentrations. Soaps can be used in combination with suitable antioxidants, such as ethylenediaminetetraacetic acid (EDTA) and / or ethane-1-hydroxy-1,1-bisphosphonic acid (H2PA). Additionally, preservatives may be present to prevent soap degradation, which can lead to foul odor or discoloration; for example, ethlidene bisphosphonic acid (H2PA).

[0076] 2. Surfactants The surfactants suitable for the cleaning formulations of this disclosure include one or more surfactant molecules of formula I or II and / or co-surfactant molecules. Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0077] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0078] More specifically, R 3 You can choose from the following formula: .

[0079] In particular, suitable surfactants or co-surfactants may include any one or more of the surfactants 1-12 described herein.

[0080] Anionic surfactants are well known to those skilled in the art. Examples include alkylbenzene sulfonates, particularly linear alkylbenzene sulfonates, primary and secondary alkyl sulfates, particularly primary alkyl sulfates; alkyl ether sulfates; olefin sulfonates; alkyl xylene sulfonates; dialkyl sulfosuccinates; and fatty acid ester sulfonates. Sodium salts are commonly and frequently used. In one example of this disclosure, a particulate laundry detergent composition comprises an anionic surfactant, which is a sulfonate anionic surfactant. The sulfonate anionic surfactant may comprise linear alkylbenzene sulfonates (LAS). The anionic surfactant may be present in an amount of 15 to 50% by weight. For example, the weight ratio of the anionic surfactant to soap is 0.5:1 to 5:1, such as 1:1 to 2:1. Some nonionic surfactants are well-suited for use in detergent formulations.

[0081] In some embodiments, the nonionic surfactant is present in an amount of 20 to 60% by weight. Permissible nonionic surfactants include primary and secondary alcohol ethoxylates, particularly C8-C20 aliphatic alcohols ethoxylated with an average of 1 to 20 moles of ethylene oxide per mole of alcohol, and more particularly, C10-C15 primary and secondary aliphatic alcohols ethoxylated with an average of 1 to 10 moles of ethylene oxide per mole of alcohol. Nonethoxylated nonionic surfactants include alkyl polyglycosides, glycerol monoethers, and polyhydroxyamides (glucosamides).

[0082] Examples of suitable nonionic surfactants include Neodol 255E from Shell, a C12 to C15 poly(1 to 6) ethoxylate with an average degree of ethoxylation of 5. Also suitable is Lutensol A7, a C13 to C15 ethoxylate from BASF with an average degree of ethoxylation of 7. HLB values ​​can be calculated according to the method given in Griffin, J. Soc. Cosmetic Chemists, 5 (1954) 249 256.

[0083] 3. Detergent builders Builders can be added to detergent formulations to enhance the detergent's cleaning properties. Such compounds can function by at least one of the following actions: removing or chelating substances typically found in water as Ca... 2+ and / or Mg 2+ It exists as a divalent cation; it generates or promotes the formation of an alkaline environment; it enhances the performance of surfactants; and it stabilizes the dispersion of soil in detergent solutions.

[0084] Commonly used detergent builders include, but are not limited to, sodium tripolyphosphate, hypochlorous acid salts, and zeolite.

[0085] The compositions disclosed herein may contain a detergent builder. The builder may be present in an amount of 0 to 15% by weight based on the total composition. Alternatively, the compositions may be substantially free of detergent builders.

[0086] Self-strengthening builders such as phosphate builders, aluminosilicate builders, and mixtures thereof may be used. One or more mild builders, such as calcite / carbonate, citrate, or polymer builders, may also be present, either additionally or alternatively.

[0087] Phosphate builders (if present) may be, for example, pyrophosphates, orthophosphates and tripolyphosphates of alkali metals (e.g., sodium), and mixtures thereof.

[0088] Aluminosilicates (if present) may be selected, for example, from one or more crystalline and amorphous aluminosilicates, such as zeolites disclosed in GB 1473201 (Henkel), amorphous aluminosilicates disclosed in GB 1473202 (Henkel), and mixed crystalline / amorphous aluminosilicates disclosed in GB 1470250 (Procter & Gamble); and layered silicates disclosed in EP 164514B (Hoechst).

[0089] Alkali metal aluminum silicates can be crystalline, amorphous, or mixtures thereof, and have the following general formula: 0.8-1.5Na2O.Al2O30.8-6SiO2.

[0090] These materials typically contain some bound water and require a calcium ion exchange capacity of at least 50 mg CaO / g. Sodium aluminosilicate can contain 1.5–3.5 SiO2 units (in the above formula). Both amorphous and crystalline materials can be readily prepared by the reaction between sodium silicate and sodium aluminate, as well as well described in the literature. Suitable crystalline sodium aluminosilicate ion exchange detergents are described, for example, in GB 1429143 (Procter & Gamble). This type of sodium aluminosilicate is well known from commercially available zeolites A and X and mixtures thereof.

[0091] Zeolite can be commercially available Zeolite 4A, which is now widely used in laundry detergent powders. However, examples of this disclosure will include cases where the zeolite builder incorporated into the compositions of this disclosure is the largest aluminum zeolite P (zeolite MAP) as described and claimed in EP 384070A (Unilever). Zeolite MAP is defined as an alkali metal aluminum silicate of the Zeolite P type having a silicon to aluminum ratio not exceeding 1.33, for example in the range of 0.90 to 1.33, or in the range of 0.90 to 1.20.

[0092] Suitable inorganic salts include basic reagents such as alkali metal (e.g., sodium) carbonates, sulfates, silicates, and metasilicates, either as standalone salts or as disalts. Inorganic salts can be selected from sodium carbonate, sodium sulfate, burkeite, and mixtures thereof.

[0093] 4. Surfactant ingredients In addition to the surfactants and builders discussed above, the composition may optionally contain other active ingredients to enhance performance and properties.

[0094] Other detergent active compounds (surfactants) can be selected from soap and non-soap anionic, cationic, nonionic, amphoteric, and zwitterionic detergent active compounds and mixtures thereof. Many suitable detergent active compounds are available and are fully described in the literature, for example, in "Surface-Active Agents and Detergents", Volumes I and II, Schwartz, Perry, and Berch.

[0095] Usable cationic surfactants include quaternary ammonium salts of the general formula RRRRNX, wherein R is a long or short hydrocarbon chain, typically alkyl, hydroxyalkyl, or ethoxylated alkyl, and X is a solubilizing anion (e.g., where R is C8-C). 22 Alkyl groups, such as C8-C 10 Or C 12 -C 14 Alkyl groups, where R is a methyl group and R and R can be the same or different, and are compounds with methyl or hydroxyethyl groups; and cationic esters (e.g., choline esters).

[0096] Amphoteric surfactants and / or amphoteric surfactants may also be present. Some amphoteric surfactants that can be used to implement this disclosure include amine oxides.

[0097] Some of the zwitterionic surfactants that can be used in the practice of this disclosure include betaines, such as amide betaines.

[0098] 5. Bleach The detergent compositions according to this disclosure may suitably contain a bleaching system. The bleaching system may be based on a peroxy bleaching compound, such as an inorganic peracid or an organic peroxyacid, which is capable of generating hydrogen peroxide in an aqueous solution. Suitable peroxy bleaching compounds include organic peroxides (e.g., urea peroxide) and inorganic peracids (e.g., alkali metal perborates, percarbonates, superphosphates, persilicates, and persulfates). Suitable inorganic peracids may be sodium perborate monohydrate and tetrahydrate, and sodium percarbonate. For example, sodium percarbonate with a protective coating is suitable to prevent damage due to moisture instability. Sodium percarbonate with a protective coating comprising sodium metaborate and sodium silicate is disclosed in GB 2123044B (Kao).

[0099] The peroxide bleaching compound is suitably present in amounts of 5 to 35% by weight, for example, 10 to 25% by weight.

[0100] Peroxide bleaching compounds can be used in combination with bleaching activators (bleaching precursors) to improve bleaching performance at low washing temperatures. The bleaching precursor is suitably present in amounts of 1 to 8% by weight, for example, 2 to 5% by weight.

[0101] Suitable bleaching precursors are peroxycarboxylic acid precursors, more particularly peracetic acid precursors and peroxybenzoic acid precursors; and peroxycarbonic acid precursors. Examples of useful bleaching precursors suitable for this disclosure are N,N,N',N'-tetraacetylethylenediamine (TAED). Also of interest are peroxybenzoic acid precursors, particularly N,N,N-trimethylammonium toluoy loxybenzene sulfonate.

[0102] Bleaching stabilizers (heavy metal masking agents) may also be present. Suitable bleaching stabilizers include ethylenediaminetetraacetic acid (EDTA) and polyphosphonates, such as Dequest (trademark), EDTMP.

[0103] 6. Enzymes Detergent compositions may also contain one or more enzymes. Suitable enzymes include, for example, proteases, amylases, cellulases, oxidases, mannanases, peroxidases, and lipases that can be incorporated into detergent compositions. In granular detergent compositions, detergent enzymes are typically used in granular form at an amount of about 0.1 to about 3.0% by weight. However, any suitable physical form of the enzyme may be used in any effective amount.

[0104] 7. Polymers Some detergents may include cationic polymers. When used in laundry detergent compositions in amounts from about 0.01% to about 15% by weight, cationic polymers (such as those described below) effectively improve the foaming profile of such laundry detergent compositions compared to similar formulations that do not contain such cationic polymers.

[0105] Cationic polymers used in detergents, such as laundry detergents, include the following substances. The cationic polymers used in this disclosure are terpolymers containing three different types of structural units. They are substantially free of any other structural components, and for example, substantially free of any other structural components. The structural units or monomers may be incorporated into the cationic polymer in a random form or in a block form.

[0106] The first structural unit in the cationic polymer of this disclosure is a nonionic structural unit derived from (meth)acrylamide (AAm). The cationic polymer contains about 35 mol% to about 85 mol%, for example about 55 mol% to about 85 mol%, or about 65 mol% to about 80 mol% of AAM-derived structural units.

[0107] The second structural unit in the cationic polymer is a cationic structural unit derived from any suitable water-soluble cationic olefinic unsaturated monomer, such as N,N-dialkylaminoalkyl methacrylate, N,N-dialkylaminoalkyl methacrylate, N,N-dialkylaminoalkyl acrylamide, N,N-dialkylaminoalkyl methacrylamide, methacrylamidoalkyl trialkylammonium salt, acrylamide trialkylammonium salt, ethyleneamine, vinylimidazole, quaternized vinylimidazole, and diallyl dialkylammonium salt.

[0108] For example, the second cationic structural unit can be derived from monomers selected from: diallyl dimethylammonium salt (DADMAS), N,N-dimethylaminoethyl acrylate, N,N-dimethylaminoethyl methacrylate (DMAM), [2-(methacryloylamino)ethyl]tri-methylammonium salt, N,N-dimethylaminopropylacrylamide (DMAPA), N,N-dimethylaminopropylmethacrylamide (DMAPMA), acrylamidopropyltrimethylammonium salt (APTAS), methacrylamidopropyltrimethylammonium salt (MAPTAS), and quaternized vinylimidazolium (PVi), and combinations thereof.

[0109] In some embodiments, the second cationic structural unit is derived from diallyl dimethylammonium salts (DADMAS), such as diallyl dimethylammonium chloride (DADMAC), diallyl dimethylammonium fluoride, diallyl dimethylammonium bromide, diallyl dimethylammonium iodide, diallyl dimethylammonium hydrogen sulfate, diallyl dimethylalkylammonium sulfate, diallyl dimethylammonium dihydrogen phosphate, diallyl dimethylalkylammonium hydrogen phosphate, diallyl dimethylalkylphosphonate hydrogen phosphate, diallyl dimethyl dialkylammonium phosphate, and diallyl dimethyl alkylphosphonate ammonium. Alternatively, the second cationic structural unit may be derived from [2-(methacryloami)ethyl]trimethylammonium salts, such as [2-(methacryloami)ethyl]trimethylammonium chloride, [2-(methacryloami)ethyl]trimethylammonium fluoride, [2-(methacryloami)ethyl]trimethylammonium bromide, [2-(methacryloami)ethyl]trimethylammonium iodide, [2-methacryloami]ethyl]trimethylammonium hydrogen sulfate, [2-(methacryloami)ethyl]trimethylalkylammonium sulfate, [2-(methacryloami)ethyl]trimethylammonium dihydrogen phosphate, [2-(methacryloami)ethyl]trimethylalkylammonium hydrogen phosphate, [2-(methacryloami)ethyl]trimethylalkylphosphonate ammonium hydrogen, [2-(methacryloami)ethyl]trimethyldialkylammonium phosphate, [2-(methacryloami)ethyl]trimethylalkylphosphonate ammonium, and combinations thereof. Furthermore, the second cationic structural unit can be derived from APTAS, including, for example, acrylamidopropyltrimethylammonium chloride (APTAC), acrylamidopropyltrimethylammonium fluoride, acrylamidopropyltrimethylammonium bromide, acrylamidopropyltrimethylammonium iodide, acrylamidopropyltrimethylammonium hydrogen sulfate, acrylamidopropyltrimethylalkylammonium sulfate, acrylamidopropyltrimethylammonium dihydrogen phosphate, acrylamidopropyltrimethylalkylammonium hydrogen phosphate, acrylamidopropyltrimethylalkylphosphonate hydrogen phosphate, acrylamidopropyltrimethyldialkylammonium phosphate, acrylamidopropyltrimethylalkylphosphonate ammonium, and combinations thereof. Furthermore, the second cationic structural unit can be derived from MAPTAS, which includes, for example, methacrylamide propyltrimethylammonium chloride (MAPTAC), methacrylamide propyltrimethylammonium fluoride, methacrylamide propyltrimethylammonium bromide, methacrylamide propyltrimethylammonium iodide, methacrylamide propyltrimethylammonium hydrogen sulfate, methacrylamide propyltrimethylalkylammonium sulfate, methacrylamide propyltrimethylammonium dihydrogen phosphate, methacrylamide propyltrimethylalkylammonium hydrogen phosphate, methacrylamide propyltrimethylalkylphosphonate hydrogen phosphate, methacrylamide propyltrimethyldialkylammonium phosphate, and combinations thereof.

[0110] The second cationic structural unit is present in the cationic polymer in an amount of about 10 mol% to about 65 mol%, for example about 15 mol% to about 60 mol%, or about 15 mol% to about 30 mol%.

[0111] The presence of a relatively large amount of the first nonionic structural unit (e.g., 65 mol% to 80 mol%) and a moderate amount of the second cationic structural unit (e.g., 15 mol% to 30 mol%) ensures good foaming benefits and a good finished product appearance. If the first nonionic structural unit is present at less than 65 mol%, and if the second cationic structural unit is present at more than 30 mol%, the foaming benefits or finished product appearance begin to be impaired; for example, the rinsing foam volume may increase significantly, or the finished product may no longer be transparent but appear cloudy. Similarly, if the first nonionic structural unit is present at more than 85 mol%, and if the second cationic structural unit is present at less than 10 mol%, the rinsing foam volume increases to a level that is no longer acceptable for the purposes of this disclosure.

[0112] The third structural unit in the cationic polymer is an anionic structural unit derived from (meth)acrylic acid (AA) or its anhydride. The cationic polymer may contain about 0.1 mol% to about 35 mol%, for example 0.2 mol% to about 20 mol%, or about 0.5 mol% to about 10 mol%, or even about 1 mol% to about 5 mol% of the third anionic structural unit.

[0113] The presence of a relatively small amount of the third anionic structural unit (e.g., 1 mol% to 5 mol%) helps increase the hydrophilicity of the resulting polymer and can consequently lead to better cleaning, especially better clay removal. Too much of the third anionic structural unit (e.g., more than 30 mol%) may impair the foaming benefits of the resulting polymer.

[0114] II. Dry cleaning According to some aspects of this disclosure, formulations for household dry cleaning are provided, the household dry cleaning comprising a dry cleaning step of contacting clothing articles stained with soil with a dry cleaning composition, wherein the liquid-to-cloth ratio (w / w) (LCR) is at most 20, and wherein the composition comprises: a) Non-flammable, chlorine-free organic dry cleaning solvents; b) Cleaning effective amounts of acidic surfactants.

[0115] In some embodiments, the dry cleaning step is a low-water dry cleaning step, and the composition is a low-water dry cleaning composition containing 0.01 to 10% by weight of water.

[0116] According to another aspect of this disclosure, a dry cleaning method further includes a non-aqueous dry cleaning step, wherein the clothing article is in contact with a non-aqueous dry cleaning composition comprising 0.001 to 10% by weight of a surfactant; 0 to 0.01% by weight of water; 0 to 50% by weight of a co-solvent; and a non-flammable, chlorine-free organic dry cleaning solvent. According to another aspect of this disclosure, a sequential dry cleaning method is provided, comprising: A) a non-aqueous dry cleaning step, wherein the article is in contact with a non-aqueous dry cleaning composition comprising 0.001 to 10 wt% surfactant; 0 to 0.01 wt% water; 0 to 50 wt% co-solvent and non-flammable, chlorine-free organic dry cleaning solvent; b) at least one low-aqueous dry cleaning step, wherein the article is in contact with a low-aqueous dry cleaning composition comprising 0.001 to 10 wt% cleaning-effective amount of acid surfactant; 0.01 to 50 wt% water; 0 to 50 wt% co-solvent; and non-flammable, chlorine-free organic dry cleaning solvent; and optionally at least one rinsing step, wherein the article is in contact with a rinsing composition comprising 0 to 0.0001 wt% surfactant; 0 to 10 wt% water; 0 to 50 wt% co-solvent and non-flammable, chlorine-free organic dry cleaning solvent.

[0117] Depending on the desired cleaning effect, the aqueous and non-aqueous compositions can be used in any order. However, in some cases, it may be useful to contact the article with the non-aqueous composition before the aqueous dry cleaning composition. In fact, the aqueous dry cleaning step can be performed after or before a variety of other steps such as regeneration, garment care treatment and / or rinsing steps, and any other steps known to those skilled in the art.

[0118] Some aspects of this disclosure are particularly applicable to cleaning clothing articles stained with household stains selected from kitchen greases, granular dirt, and mixtures thereof. Therefore, according to one embodiment, a dry cleaning method may include the step of contacting the clothing article with a dry cleaning composition, wherein the clothing article is stained with household stains selected from kitchen greases, granular dirt, and mixtures thereof. Typical granular dirt stains include any particulate matter capable of staining clothing, such as dust, mud, sand, charcoal, cosmetics, deodorants, toothpaste, and corroded iron particles and mixtures thereof. Kitchen greases typically include edible fats and oils of animal or plant origin, such as lard, sunflower oil, soybean oil, olive oil, palm oil, peanut oil, rapeseed oil, and mixtures thereof.

[0119] Typically, articles, such as clothing, are cleaned by contacting an effective amount of a dry cleaning composition according to one aspect of this disclosure with the article for an effective period of time to clean the article or otherwise remove stains, for example, by immersing the clothing article in a dry cleaning composition. The amount of dry cleaning composition used and the amount of time the composition contacts the article can vary based on the equipment and the number of articles being cleaned. Typically, a dry cleaning method will include at least one step: contacting the article with a dry cleaning composition according to the first aspect of this disclosure, and at least one step of rinsing the article with a fresh load of dry cleaning solvent. The rinsing composition will typically consist primarily of solvent, but detergents may be added as desired.

[0120] In some aspects of this disclosure, the in-situ formulation of a dry cleaning composition may be included in a pretreatment composition. The garment article is pretreated with the pretreatment composition, and then the pretreated garment article is brought into contact with the remaining components of the dry cleaning composition to produce the dry cleaning composition in situ. As part of the pretreatment step, the pretreatment step may be performed manually outside the drum of a cleaning machine or mechanically inside the drum. The pretreatment step itself does not need to be immersion-type; that is, it may be limited to treating the stained area, provided that the garment article is immersed in the dry cleaning composition while it is in contact with all the components constituting the final dry cleaning composition. For example, when the dry cleaning composition contains a dry cleaning solvent, water, and a surfactant, the stained area of ​​the garment article may be pretreated manually or by an automated method with a premix of water and surfactant. After an effective pretreatment time, the garment article may be brought into contact with the remaining components in the drum. The remaining dry cleaning components may include a dry cleaning solvent (and optionally additional water and / or detergent) to produce at least one dry cleaning composition according to this aspect of the disclosure in situ. Typically, the pretreatment time will be at least 5 seconds, but may be less than one day, for example less than one hour or less than 30 minutes. The pretreatment composition may be formulated to treat specific stains. For example, it may include a cleaning-effective amount of proteases and other enzymes to treat protein stains. In another embodiment, the completely dried cleaning composition is premixed in a separate premixing compartment. For example, when the dry cleaning composition contains a dry cleaning solvent, a surfactant, and water, these may be premixed in a separate compartment before the dry cleaning composition comes into contact with the garment. In some embodiments, this premix is ​​in the form of an emulsion or microemulsion. Premixes forming, for example, water-in-oil emulsions can be brought in by any number of suitable procedures. For example, an aqueous phase containing a cleaning-effective amount of surfactant may be contacted with the solvent phase by metered injection before placing these components in the mixing apparatus. Metering can be maintained such that the desired solvent / water ratio remains relatively constant. Mixing apparatus suitable for this practice includes, for example, pump assemblies or in-line static mixers, centrifugal pumps or other types of pumps, colloid mills or other types of mills, rotary mixers, ultrasonic mixers, and other devices for dispersing one liquid in another. In some implementations, immiscible liquids can be used to provide sufficient stirring to form an emulsion or pseudo-emulsion.

[0121] These static mixers include devices through which emulsions are passed at high speeds, and whereby the emulsions undergo sudden changes in direction and / or the diameter of channels forming the interior of the mixer. This results in pressure loss, a factor in obtaining the correct emulsion in terms of droplet size and stability.

[0122] In one variant of the method disclosed herein, the mixing steps are, for example, sequential. The procedure comprises mixing a solvent and an emulsifier in a first stage, followed by mixing and emulsifying the premix with water in a second stage. In another variant of the method disclosed herein, a means for performing the above steps in a continuous mode is provided.

[0123] Premixing can be carried out at room temperature, which is also the temperature of the fluid and raw materials used.

[0124] Emulsions can be prepared using batch methods, such as overhead mixers, or continuous methods, such as two-fluid co-extrusion nozzles, in-line injectors, in-line mixers, or in-line screens. The size of the emulsion composition in the final composition can be adjusted by varying the mixing speed, mixing time, mixing device, and viscosity of the aqueous solution. Generally, emulsions with larger droplet sizes can be produced by reducing the mixing speed, reducing the mixing time, reducing the viscosity of the aqueous solution, or using a mixing device that generates less shear force during mixing. Ultrasonic mixers are useful. Although the above description relates to the addition of surfactants, it should be understood that it can also be applied to the addition of detergents.

[0125] 1. Solvent Generally, dry cleaning solvents are non-flammable, chlorine-free organic dry cleaning solvents. Although the term dry cleaning solvent is used in the singular, it should be noted that mixtures of solvents may also be used. Therefore, the singular should be considered to cover the plural, and vice versa. Due to the typical environmental problems associated with chlorinated solvents, solvents typically do not contain chlorine atoms. Furthermore, the solvent should not be flammable, such as most petroleum or mineral spirits with typical flash points as low as 20°C or even lower. The term non-flammable is intended to describe dry cleaning solvents with a flash point of at least 37.8°C, for example at least 45°C or at least 50°C. The limit of at least 37.8°C flash point for non-flammable liquids is defined in NFPA 30, such as the Flammable and Combustible Liquids Code issued by the National Fire Protection Association, 1996 edition, Massachusetts USA. The test method used to determine the flash point of a solvent may be a standard test as described in NFPA 30. One class of solvents are fluorinated organic dry cleaning solvents, including hydrofluorocarbons (HFCs) and hydrofluoroethers (HFEs). However, it is generally desirable to use non-flammable, non-halogenated solvents, such as siloxanes (see below). It should be noted that mixtures of different dry cleaning solvents may also be used.

[0126] Some solvents are non-ozone depleting, and a useful, generally accepted definition of ozone depletion potential (ODP) is defined by the U.S. Environmental Protection Agency (EPA): ODP is the ratio of a chemical's effect on ozone to the effect of a similar mass of CFC-11. Therefore, the ODP for CFC-11 is defined as 1.0.

[0127] Hydrofluorocarbons (HFCs) can be used as solvents. A suitable HFC solvent is represented by the formula C, H, F(2x+2-y), where x is 3 to 8, y is 1 to 6, and the molar ratio of F / H in the HFC solvent is greater than 1.6. In some cases, x is 4 to 6, or x is 5 and y is 2. Suitable HFC solvents are those selected from decafluoropentane isomers and mixtures thereof. Also used is 1,1,1,2,2,3,4,5,5,5-decafluoropentane. EI Du Pont De Nemours and Company sells this compound under the name Vertrel XFTM.

[0128] The hydrofluoroethers (HFEs) applicable to this disclosure are generally low-polarity chemical compounds containing at least carbon, fluorine, hydrogen, and a catenary (i.e., in the chain) oxygen atom. HFEs may optionally contain additional in-chain heteroatoms, such as nitrogen and sulfur. HFEs have a molecular structure that can be straight-chain, branched, or cyclic, or a combination thereof (e.g., alkyl alicyclic), and suitably lack olefinic unsaturation, having a total of about 4 to about 20 carbon atoms. Such HFEs are known and readily available, either as substantially pure compounds or as mixtures. Hydrofluoroethers may have boiling points in the range of about 40°C to about 275°C, for example, about 50°C to about 200°C, or about 50°C to about 121°C. It is highly desirable that hydrofluoroethers have no flash point. Generally, when an HFE has a flash point, decreasing the F / H ratio or decreasing the number of carbon-carbon bonds each decreases the flash point of the HFE (see WO / 0026206).

[0129] Useful hydrofluoroethers include two categories: isolated hydrofluoroethers and ω-hydrofluoroalkyl ethers. Structurally, isolated hydrofluoroethers contain at least one mono-, di-, or trialkoxy-substituted perfluoroalkane, perfluorocycloalkane, perfluoroalkane containing a perfluorocycloalkyl group, or perfluoroalkane compound containing a perfluorocycloalkylene group.

[0130] Some siloxane solvents may also be advantageously used in this disclosure. Siloxanes can be linear, branched, cyclic, or combinations thereof. An example of a branched siloxane is tris(trimethylsiloxy)silane. Examples also include linear and cyclic oligomeric dimethylsiloxanes. An example of a class of siloxane solvents is alkylsiloxanes represented by the following formula: R3-Si(-O-SiR2)wR Each R is independently selected from an alkyl group having 1 to 10 carbon atoms, and w is an integer from 1 to 30. For example, R can be methyl and w is 1-4, or w is 3 or 4.

[0131] Octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane are particularly effective. Useful siloxanes can be selected from decamethyltetrasiloxane, dodecylpentasiloxane, and mixtures thereof.

[0132] Organic solvents suitable for dry cleaning include at least one solvent selected from: nonafluoromethoxybutane, nonafluoroethoxybutane and isomers of decafluoropentane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecylpentasiloxane and mixtures thereof. Suitable organic dry cleaning solvents include those selected from octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, decamethyltetrasiloxane, dodecylpentasiloxane and mixtures thereof.

[0133] The dry cleaning compositions disclosed herein may contain more than about 50% by weight of organic dry cleaning solvents, for example, more than about 75% by weight, or more than about 80% by weight, or even more than about 85% by weight, or even more than about 95% by weight, but generally less than 100% by weight of organic dry cleaning solvents, based on the total weight of the dry cleaning composition. This amount may help improve drying time and maintain a high flash point or not maintain a flash point at all. For rinsing or conditioning steps, the dry cleaning compositions may even contain at least 99% by weight of organic dry cleaning solvents and sometimes even 100% by weight of organic dry cleaning solvents based on the total weight of the dry cleaning composition.

[0134] In some cases, water may be used in dry cleaning methods and the amount of water is important. In these cases, the amount of water present in any step of the dry cleaning method is at a level that is safe for cleaning clothing. This includes clothing that can only be dry cleaned. The amount of water present in low-aqueous dry cleaning compositions can be 0.01 to 50% by weight, or 0.01 to 10% by weight. The amount of water present in non-aqueous dry cleaning compositions can be 0 to 0.1% by weight, or 0 to 0.01% by weight, or even 0 to 0.001% by weight, and / or almost zero by weight.

[0135] When a dry cleaning composition contains water, the water-to-cloth ratio (w / w) (WCR) may be less than 0.45, typically less than 0.35, or less than 0.25, or less than 0.2, or even less than 0.15, but typically greater than 0.0001, or greater than 0.001, or even greater than 0.01.

[0136] When a dry cleaning method involves more than one step, this WCR can be applied to all steps in the dry cleaning method, especially when the dry cleaning composition contains water and solvent. However, the WCR may differ for each step or it may not differ. The WCR can also be applied to each step in a dry cleaning method where the LCR is greater than 1.

[0137] 2. Cosolvent The compositions disclosed herein may contain one or more co-solvents. The purpose of the co-solvents in the dry cleaning compositions of this disclosure is generally to increase the dissolving power of the dry cleaning composition for a variety of stains. The co-solvent also enables the formation of a homogeneous solution containing a co-solvent, a dry cleaning solvent, and stain; or a co-solvent, a dry cleaning solvent, and optionally a cleaning agent. As used herein, a “homogeneous composition” is a single-phase composition or a composition that appears to have only one phase, such as a macro-emulsion, a microemulsion, or an azeotrope. However, if a co-solvent is used, the dry cleaning composition is non-azeotropic because azeotropes can be less robust.

[0138] The useful co-solvent disclosed herein is soluble in dry cleaning solvents or water, is compatible with typical detergents, and enhances the solubility of hydrophilic complex stains and oils, such as vegetable oils, mineral oils, or animal oils, commonly found in stains on clothing. Any co-solvent or mixture of co-solvents that meets the above criteria can be used.

[0139] Useful cosolvents include, for example, alcohols, ethers, glycol ethers, alkanes, alkenes, straight-chain and cyclic amides, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, their fully or partially halogenated derivatives, and mixtures thereof. Cosolvents may be selected from alcohols, alkanes, alkenes, cycloalkanes, ethers, esters, cyclic amides, aromatic compounds, ketones, their fully or partially halogenated derivatives, and mixtures thereof. Representative examples of cosolvents that can be used in the dry cleaning compositions of this disclosure include methanol, ethanol, isopropanol, tert-butanol, trifluoroethanol, pentafluoropropanol, hexafluoro-2-propanol, methyl tert-butyl ether, methyl tert-amyl ether, propylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, propylene glycol methyl ether, ethylene glycol monobutyl ether, trans-1,2-dichloroethylene, decahydronaphthalene, methyl decanoate, tert-butyl acetate, ethyl acetate, glycol methyl ether acetate, ethyl lactate, diethyl phthalate, 2-butanone, N-alkylpyrrolidone (e.g., N-methylpyrrolidone, N-ethylpyrrolidone), methyl isobutyl ketone, naphthalene, toluene, trifluorotoluene, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorotributylamine, and perfluoro-2-butyloxacyclopentane.

[0140] The co-solvent may be present in an effective amount by weight in the compositions disclosed herein to form a homogeneous composition with other (one or more) dry cleaning solvents such as HFE. The effective amount of the co-solvent will vary depending on which co-solvents or co-solvent blends are used and the other (one or more) dry cleaning solvents used in the composition. However, the maximum amount of any particular co-solvent present in the dry cleaning composition should be kept sufficiently low to keep the dry cleaning composition non-flammable, as defined above.

[0141] Typically, the co-solvent may be present in the compositions disclosed herein in an amount of about 1 to 50% by weight of the total dry cleaning composition, for example, about 5 to about 40% by weight, or about 10 to about 25% by weight. In some cases, the co-solvent may be present in an amount of about 0.01% by weight of the total dry cleaning composition.

[0142] 3. Surfactants This disclosure provides surfactants for use in cleaning products in the form of amino acid-based siloxane derivatives. Therefore, the use of compounds of formula I or II as surfactants in cleaning is disclosed herein.

[0143] This disclosure provides surfactants in the form of surfactant molecules of formula I or II for use in cleaning products. Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0144] Specifically, R 3Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0145] More specifically, R 3 You can choose from the following formula: .

[0146] In particular, suitable surfactants or co-surfactants may include any one or more of the surfactants 1-12 described herein.

[0147] The dry cleaning compositions disclosed herein can utilize many types of cyclic, linear, or branched surfactants known in the art, both fluorinated and non-fluorinated. Solvent-compatible surfactants include nonionic, anionic, cationic, and amphoteric surfactants having at least 4 carbon atoms but less than 200 carbon atoms or more, and also less than 90 carbon atoms, as described below. Solvent-compatible surfactants typically have a solubilizing portion that increases the solubility of the surfactant in the dry cleaning solvent / composition. Effective surfactants may comprise one or more polar hydrophilic groups and one or more dry cleaning solubilizing portions having at least about 4 carbon atoms, such that the surfactant is soluble in the dry cleaning solvent / composition. Generally, it is desirable for the surfactant to be soluble in the dry cleaning composition, i.e., at least at about 20°C in the amount of surfactant used in the dry cleaning composition. The composition may contain one or a mixture of surfactants, depending on the desired cleaning and garment care. One type of useful surfactant is anionic surfactant. Another type of useful surfactant is cationic surfactant.

[0148] The polar hydrophilic group Z can be nonionic, ionic (i.e., anionic, cationic, or amphoteric), or a combination thereof. Typical nonionic moieties include polyoxyethylene and polyoxypropylene moieties. Typical anionic moieties include carboxylates, sulfonates, sulfates, or phosphates. Typical cationic moieties include quaternary ammonium, protonated ammonium, imidazoline, amine, diamine, sulfonium, and phosphonium moieties. Typical amphoteric moieties include betaine, sulfobetaine, aminocarboxyl, amine oxides, and various other combinations of anionic and cationic moieties. Particularly suitable surfactants contain at least one polar hydrophilic group Z, which is an anionic moiety, wherein the counterion can be as described below.

[0149] The polar hydrophilic group Z can be selected from -SOM, -SOM, -POM, -POM, -COM and mixtures thereof, wherein each M can be independently selected from H, NR, Na, K and Li, and each R can be independently selected from H and C alkyl groups, but more likely H. Usually M is H, but salts can be used in some cases.

[0150] Surfactants can be fluorinated, such as fluorinated acids. Suitable fluorinated surfactants are, in most cases, those according to formula (1): (Xf)n(Y)m(Z)p It contains one, two, or more fluorinated groups (Xf) and one or more polar hydrophilic groups (Z), which are usually (but not necessarily) linked together by one or more suitable linking groups (Y). For example, n and p are independent integers selected from 1 to 4, and m is selected from 0 to 4. When a surfactant contains more than one Xf, Y, or Z group, each of Xf, Y, and Z can be the same or different. The polar hydrophilic group can be linked to Y by a covalent bond, or to Xf in the absence of Y.

[0151] The fluorinated group Xf can typically be a straight-chain or cyclic, saturated or unsaturated, aromatic or non-aromatic group having at least three carbon atoms. The carbon chain can be straight or branched and can include heteroatoms such as oxygen or sulfur, but typically not nitrogen. Xf is aliphatic and saturated. Perfluorinated Xf groups are frequently used, but hydrogen or chlorine can be present as substituents, provided that no more than one of any atom is present for every two carbon atoms, and, for example, the group contains at least a terminal perfluoromethyl group. Groups containing no more than about 20 carbon atoms are generally used, as larger groups typically indicate less efficient utilization of fluorine. Particularly suitable Xf groups can be based on perfluorinated carbon:CF, where n is 1-40, for example 2 to 26, or 2 to 18, or can be based on oligomers of hexafluoropropylene oxide:ICF(CF)—CF.O, where n is 1 to 30. A suitable example of the latter is given by E. IDuPont de Nemours and Co. under the name Krytoxl. TM 157 sales, especially Krytoxl TM 157 FSL. More commonly used are fluorinated aliphatic groups containing about 2 to 14 carbon atoms.

[0152] The linking group Y is selected from alkyl, alkylene, alkylene oxide, aryl, carbonyl, ester, amide, ether oxide, secondary or tertiary amine, sulfonamide alkylene, carboxamidoalkylene, alkylsulfonamide alkylene, alkyleneoxyalkylene, or alkylenethioalkylene, or mixtures thereof. In one example, Y is (CH2) or (CH2)O, where t is 1 to 10, for example 1 to 6 or 2 to 4. Alternatively, Y may be absent, in which case Xf and Z are directly linked by a covalent bond.

[0153] Another suitable type of surfactant is the nonfluorinated surfactant according to formula (2): (Xh)n(Y)m(Z)p, Where Xh is a non-fluorinated group, and (Y), (Z), n, m and p are as described in Formula I.

[0154] Xh can be straight-chain, branched, or cyclic, saturated or unsaturated, aromatic or non-aromatic, and the group can have at least four carbon atoms. Xh can include a hydrocarbon group. When Xh is a hydrocarbon, the carbon chain can be straight-chain, branched, or cyclic, and can include heteroatoms such as oxygen, nitrogen, or sulfur, although nitrogen may be undesirable in some cases. In some embodiments, Xh is aliphatic and saturated. Groups containing no more than about 24 carbon atoms can be used.

[0155] An example of a suitable surfactant is an acid surfactant. Some surfactants include anionic surfactants. Anionic surfactants are generally known in the art and include, for example, alkyl aryl sulfonates (e.g., alkylbenzene sulfonates), alkyl aryl sulfonic acids (e.g., sodium and ammonium salts of toluene-, xylene-, and isopropylbenzene sulfonic acids), sulfonated amines and sulfonated amides (e.g., amide sulfonates), carboxylated alcohols and carboxylated alkylphenol ethoxylates, diphenyl sulfonates, fatty esters, hydroxyethyl sulfonates, lignin-based surfactants, and olefin sulfonates (e.g., RCHCHSO3Na, where R is C). 10 -C 16This includes phosphorus-based surfactants, protein-based surfactants, sarcosine-based surfactants (e.g., N-acylsarcosine salts such as sodium N-lauroylsarcosine), sulfates and sulfonates of oils and / or fatty acids, sulfates and sulfonates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, sulfates of fatty esters, sulfates of aromatic or fluorinated compounds, sulfosuccinnamates, sulfosuccinates (e.g., dipentyl-, dioctyl-, and diisobutyl sulfosuccinates), taurines, and sulfonic acids. Examples of suitable nonfluorinated anionic surfactants include Crodafos™ 810A (ex Croda).

[0156] Besides acid surfactants, other types of surfactants can be used. Suitable surfactants include, but are not limited to, nonionic and cationic surfactants. Compounds suitable for use as nonionic surfactants in this disclosure are those that do not carry a discrete charge when dissolved in an aqueous medium. Nonionic surfactants are generally known in the art and include, for example, alkanolamides (e.g., monoethanolamides, diethanolamides, and monoisopropanolamides of coconut oil, lauric acid, oleic acid, and stearic acid), amine oxides (e.g., polyoxyethylene ethanolamides and polyoxyethylene propanolamides), polyoxyalkylene block copolymers (e.g., poly(ethylene oxide co-propylene oxide)), ethoxylated alcohols (e.g., isostearyl polyoxyethylene alcohol, lauryl, hexadecyl, stearyl, oleylene, tridecyl, trimethylnonyl, isodecyl, tridecyl), ethoxylated alkylphenols such as nonylphenol, ethoxylated amines and ethoxylated amides, ethoxylated fatty acids, ethoxylated fatty esters and ethoxylated fatty oils (e.g., acids such as lauric acid, isostearic acid, nonanoic acid, pelargonic acid, oleic acid, coconut oil acid, stearic acid, and... Castor oil, and oils such as castor oil and tall oil monoesters and diesters), fatty esters, fluorinated materials, glycerides (e.g., glyceryl monostearate, glyceryl monolaurate, glyceryl dilaurate, glyceryl monoricinoleate, and glyceryl oleate), glycol esters (e.g., propylene glycol monostearate, ethylene glycol monostearate, ethylene glycol distearate, diethylene glycol monolaurate, diethylene glycol monooleate, and diethylene glycol stearate), lanolin-based surfactants, monoglycerides, phosphate esters, polysaccharide ethers, propoxylated fatty acids, propoxylated alcohols, and propoxylated alkylphenols, protein-based organic surfactants, sorbitol-based surfactants (e.g., sorbitol oleate, sorbitol monolaurate, and sorbitol palmitate), sucrose esters and glucose esters, and thio- and thiol-based surfactants.

[0157] Some other suitable nonionic surfactants may include polyoxyethylene condensates of nonylphenol and myristol, such as Kasprzak in U.S. Patent No. 4,685,930; and fatty alcohol ethoxylates, R-(OCH2CH 2) OH, where a-1 to 100, typically 1 to 30, and R = hydrocarbon residue with 8 to 20 C atoms, typically a straight-chain alkyl group. Examples include polyoxyethylene lauryl ether having 4 or 10 oxyethylene groups; polyoxyethylene hexadecyl ether having 2, 6, or 10 oxyethylene groups; polyoxyethylene stearyl ether having 2, 5, 15, 20, 25, or 100 oxyethylene groups; and polyoxyethylene oleyl ether having 2 or 10 oxyethylene groups. Commercially available examples include, but are not limited to, BRIJ and NEODOL. See also U.S. Patent No. 6,013,683, Hill et al. Other suitable nonionic surfactants include Tween. TM .

[0158] Suitable cationic surfactants include, but are not limited to, dialkyldimethylammonium salts having the following formula: R"R"N"(CH).X, where R' and R'' are each independently selected from hydrocarbon moieties containing 1-30 carbon atoms or derived from tallow, coconut oil, or soybean, and X-Cl, I, or Br. Examples include: didodecyldimethylammonium bromide (DDAB), dihexadecyldimethylammonium chloride, dihexadecyldimethylammonium bromide, dioctadecyldimethylammonium chloride, dieicodecyldimethylammonium chloride, dicoconutdimethylammonium chloride, and ditallowdimethylammonium bromide (DTAB). Commercially available examples include, but are not limited to: ADOGEN, ARQUAD, TOMAH, and VARIOUAT. See also U.S. Patent No. 6,013,683 to Hill et al.

[0159] These and other surfactants suitable for use in combination with organic dry cleaning solvents as auxiliaries are well known in the art and described in more detail in Kirk Othmer’s Encyclopaedia of Chemical Technology, 3rd Ed., Vol. 22, pp. 360-379, “Surfactants and Detersive Systems,” which is incorporated herein by reference. Other suitable nonionic detergent surfactants are generally disclosed in U.S. Patent No. 3,929,678, Dec. 30, 1975, Laughlin et al., column 13, lines 14 through 16, lines 6, which is incorporated herein by reference. Other suitable detergent surfactants are generally disclosed in WO-A-0246517.

[0160] The surfactant or mixture of surfactants is present in a cleaning-effective amount. The cleaning-effective amount is the amount required for the desired cleaning. This will, for example, depend on the quantity of products used, the level of dirt, and the volume of the dry cleaning composition. Effective cleaning is observed when the surfactant is present in a concentration of at least 0.001% to 10% by weight of the dry cleaning composition. For example, the surfactant is present in a concentration of 0.01% to 3% by weight or 0.05% to 0.9% by weight of the dry cleaning composition. Alternatively, the surfactant is present in a concentration of 0.1% to 0.8% by weight of the dry cleaning composition, or, for example, 0.3% to 0.7% by weight.

[0161] The dry cleaning composition may contain one or more optional cleaning agents. The cleaning agents include any agents suitable for enhancing cleanliness, appearance, condition, and / or garment care. Typically, the cleaning agent may be present in the compositions disclosed herein in an amount of about 0 to 20% by weight, for example, from 0.001% to 10% by weight, or from 0.01% to 2% by weight, based on the total weight of the dry cleaning composition.

[0162] Suitable cleaning agents include, but are not limited to, the following compounds: builders, enzymes, bleaching activators, bleaching catalysts, bleaching accelerators, bleaching agents, alkalinity sources, antibacterial agents, colorants, fragrances, pre-fragrances, finishing aids, lime soap dispersants, odor control agents, odor neutralizers, polymer dye transfer inhibitors, crystal growth inhibitors, photobleaching agents, heavy metal ion masking agents, and anti-tarnishing agents. Agents, antimicrobial agents, antioxidants, anti-redeposition agents, dirt-releasing polymers, electrolytes, pH adjusters, thickeners, abrasives, divalent or trivalent ions, metal ion salts, enzyme stabilizers, corrosion inhibitors, diamines or polyamines and / or their alkoxylated derivatives, foam-stabilizing polymers, processing aids, fabric softeners, optical brighteners, water-soluble additives, foam (SUDS) or foam inhibitors, foam (SUDS) or foam promoters, fabric softeners, antistatic agents, dye fixing agents, dye abrasion inhibitors, anti-crocking agents, wrinkle reducers, anti-wrinkle agents, stain repellents, sunscreens, anti-fading agents, and mixtures thereof.

[0163] III. Cleaning compositions and systems for hard surfaces Other hard surface cleaning applications for the compounds disclosed herein include in-situ cleaning systems (CIP), clean-out systems (COP), washer-detergent systems, sterilizers, textile washing machines, ultrafiltration and nanofiltration systems, and indoor air filters. COP systems may include easily accessible systems such as wash tanks, soaking containers, mop buckets, holding tanks, wash tubs, vehicle component cleaners, non-continuous intermittent cleaning machines and systems, etc. CIP systems include internal components of tanks, lines, pumps, and other process equipment for handling typically liquid product streams (e.g., beverages, milk, and juice).

[0164] Typically, actual cleaning of in-situ systems or other surfaces (e.g., removal of unwanted viscera) can be accomplished with materials such as formulated cleaning agents introduced with hot water. Following this cleaning step, a washing / cleaning composition containing the molecules described herein can be applied to or introduced into the system at a solution concentration, such as that prepared in unheated ambient temperature water.

[0165] Sufficiently high flow rates, such as about 40 to about 600 liters per minute, can be used with CIP compositions to allow the CIP system to have a contact time of at least about 10 seconds, for example, about 30 to about 120 seconds, with the hard surface it is intended to clean, at temperatures ranging from ambient to about 70°C. However, cleaning compositions containing the surfactant compounds described herein can be used in solutions of cold (e.g., 40℉ / 4°C) water as well as heated (e.g., 140℉ / 60°C) water. While the use of cleaning compositions containing the compounds described herein is not necessary, in some cases, heating may be desirable to further enhance surface activity. Therefore, cleaning compositions containing the surfactant molecules disclosed herein should be useful and usable at any conceivable temperature.

[0166] A method for disinfecting a substantially stationary in-situ treatment facility may include the following steps: A cleaning composition comprising one or more surfactant compounds of the present disclosure is introduced into the treatment facility at a temperature ranging from about 4°C to 60°C. After the introduction of the working solution, the solution is held in a container or circulated throughout the system for a sufficient time to disinfect the treatment facility (e.g., to kill unwanted microorganisms). After disinfection of the surfaces by the composition, the working solution is drained. After the disinfection step is completed, the system may optionally be rinsed with other materials such as potable water. The cleaning composition used may then be recycled through the treatment facility for further rounds of reuse, or, if desired, for purification and reconstitution before being put into further cleaning-in-process rounds. Along these lines, the method may also include alternatives such as delivering the cleaning composition comprising one or more surfactant compounds of the present disclosure via air delivery to in-situ cleaning or other surfaces, such as those inside pipes and tanks. In many cases, this air delivery method can reduce the volume of solution required. The described method can be readily adapted to remove the cleaning system.

[0167] 1. A method for cleaning food product containers.

[0168] In some aspects, this disclosure provides methods for cleaning utensils or containers that are intended for food contact, wherein the composition comprises one or more surfactant compounds disclosed below, employing any method or apparatus suitable for applying such a composition. In some cases, food products are placed in direct contact with a cleaning composition comprising one or more surfactant compounds of the present invention, for example, the cleaning composition may be in the form of a spray or bath, thereby allowing the food product to be immersed therein, or in the form of a foam or gel, which may be coated or otherwise applied to coat the food product, for example, using methods known in the food preparation and handling industries. Contact with a cleaning composition comprising one or more surfactant compounds of the present disclosure can occur anywhere where food products can be found, such as fields, processing sites or plants, vehicles, warehouses, shops, restaurants, or homes.

[0169] Cleaning compositions comprising one or more surfactant compounds of the present invention, intended for direct contact with food products, may require a minimum contact time with the food product to achieve a cleaning or antimicrobial effect. The contact time can vary depending on the concentration of the surfactant compound used in the cleaning composition, the form of the cleaning composition, the method of application of the cleaning composition, the temperature at which the cleaning composition is applied, and also the amount of dirt or microorganisms typically present on the food product, the type of antimicrobial agent included in the cleaning composition, etc. The exposure period can be from at least about 5 seconds to about 15 seconds. In some embodiments, the exposure time can be from about 15 to about 30 seconds. In other embodiments, the exposure time is at least about 30 seconds.

[0170] In some embodiments, the method for washing food products employs a pressurized spray solution composition comprising one or more surfactant compounds disclosed herein. During the application of the spray solution composition to the food product, the surface of the food product can be moved by mechanical action (e.g., agitation, friction, brushing, etc.). Agitation can include actions that physically wash the food product via the action of the spray solution under pressure, by ultrasound, or by other methods. Agitation increases the effectiveness of the spray solution in killing microorganisms, possibly by better or higher exposure of the spray solution to cracks or small colonies containing undesirable microorganisms. The spray solution can also be heated to a temperature of approximately 15 to 20°C, such as approximately 20 to 60°C, prior to application to enhance cleaning efficacy. Once the spray solution is applied to the food product, it can be retained on the food product for a sufficient period of time to appropriately reduce the population of undesirable microorganisms before the food product is rinsed, drained, and the spray solution composition is thus evaporated, rinsed, and dried, or otherwise removed from the food product.

[0171] Applying a cleaning composition by spraying can be achieved using manual spray bar application, automated spraying with multiple nozzles on food products moving along a production line to ensure complete contact, or other spraying equipment. An automated spray application involves the use of a spray chamber. The spray chamber essentially confines the sprayed cleaning composition within its interior. The production line moves the food products into the spray chamber through an inlet channel, where the food products are sprayed onto all their outer surfaces by a spray within the chamber. After the food products are completely covered by the sprayed cleaning composition and excess cleaning composition is removed from the food products within the chamber, the food products then leave the chamber via, for example, an automated conveyor. The spray chamber may include steam jets that can be used to apply a cleaning composition comprising one or more surfactant compounds disclosed herein. These steam jets may be used in combination with cooling water to ensure that the treatment reaching the surface of the food products is less than 65°C, for example, less than 60°C. The spray temperature on the food products is important to ensure that the food products are not substantially altered (cooked) by the temperature of the sprayed composition. The spray pattern that can be applied can be any useful spray pattern.

[0172] Immersion of food products in a liquid cleaning composition comprising one or more surfactant compounds of this disclosure can be achieved by any of a variety of methods known to those skilled in the art. For example, the food product can be placed in a tank or basin containing the cleaning composition. Alternatively, the food product can be transported or processed in a flume containing the cleaning composition. The cleaning composition can be agitated to increase cleaning efficacy, and the composition comprising one or more surfactant compounds of this disclosure can reduce the rate at which undesirable microorganisms initially present on the food product are reduced. Agitation can be achieved by conventional methods, including ultrasonication, by bubbling air through a solution, by mechanical methods (e.g., filters, paddles, brushes, pump-driven liquid jets), or by a combination of these methods. The cleaning composition can be heated to increase its effectiveness in killing undesirable microorganisms. After the food product has been immersed for a sufficient time to achieve the desired antimicrobial effect, it can be removed from the bath or flume, and the cleaning composition can be rinsed, drained, evaporated, or otherwise removed from the food product.

[0173] In other embodiments, food products can be treated with a foaming process using a cleaning composition comprising one or more surfactant compounds of the present disclosure. The foam can be prepared, for example, by mixing one or more surfactants of the present disclosure capable of foaming and / or maintaining foam with a water-based solution containing other components at the time of use. For example, the surfactant compounds used to generate and maintain foam in the cleaning composition can be inherently nonionic, anionic, or cationic, including but not limited to alcohol ethoxylates, alcohol ethoxylate carboxylates, amine oxides, alkyl sulfates, alkyl ether sulfates, sulfonates, including, for example, alkyl aryl sulfonates, quaternary ammonium compounds, alkyl sarcosines, betaine, and alkylamides. When the surfactant(s) and the cleaning composition are mixed at the time of use, the cleaning composition may contain about 50 ppm to about 2.0% by weight of one or more surfactants of the present disclosure. At the time of use, compressed air can be injected into the mixture and then applied to the surface of the food product using a foaming device such as a can-type foamer or a suction wall-mounted foamer.

[0174] In some embodiments, food products can be treated with a thickened or gelled form of a cleaning composition comprising one or more surfactant compounds disclosed herein. In the thickened or gelled state, the cleaning composition can maintain prolonged surface contact with the food product, resulting in enhanced antimicrobial efficacy. Thickened or gelled compositions generally tend to adhere more strongly to vertical surfaces, thus leading to better and more complete contact with the food product. The cleaning composition can be thickened or gelled using known prior art techniques, including, but not limited to, the use of xanthan gum, polymeric thickeners, cellulose thickeners, etc. In such applications, surfactants with counterionic properties capable of forming rod micelles, such as amine oxides and anionic surfactants, may be suitable. Thickeners or gelling agents can be used in concentrated cleaning compositions, or they can be mixed into the cleaning composition from a separate formulation upon use. Typical levels of thickeners or gelling agents used in such formulations can be from about 100 ppm to about 10 wt%.

[0175] 2. Methods for processing beverages, food, and pharmaceuticals. The surfactant compounds and compositions disclosed herein can be used to prepare beverage, food, and pharmaceutical materials, including fruit juices, dairy products, malt beverages, soy-based products, yogurt, baby food, bottled water products, tea, cough medicines, pharmaceuticals, and soft drinks. The cleaning compositions may also include antimicrobial compounds to disinfect, sterilize, act as sporicidal agents, or sterilize bottles, pumps, pipelines, tanks, and mixing equipment used in the manufacture of such beverages. Furthermore, the cleaning compositions disclosed herein can be used in aseptic, cold-fill operations, where the interior of food, beverage, or pharmaceutical containers is disinfected or sterilized prior to filling. In such operations, the container and its surface may come into contact with the disinfecting composition, typically using spray, immersion, or filling devices to ensure close contact between the interior of the container and the cleaning composition for a sufficient period of time to reduce the population of undesirable microorganisms within the container. The container may then be emptied, washed, rinsed (e.g., with drinking water or sterile water), emptied again, dried, or otherwise disposed of to remove the cleaning composition used to disinfect or clean the container. After the cleaning composition has been removed from the container, it can then be filled with the desired food product, such as a beverage, food, or pharmaceutical. The containers can then be sealed, capped, or closed, and then packaged for transport (for final sale). Sealed containers can be autoclaved or retorted to kill any added microorganisms.

[0176] Alternatively, the container to be cleaned can be a fermentation container, in which one or more cleaning steps must be performed between each batch of food product using the container to remove any residual culturable organisms and food and plant residues used as raw materials. In such applications, it is particularly important to ensure that used cultures and media, as well as any contaminating microorganisms that can be introduced by raw fruits, vegetables, seeds, grains, and other culturable substances, are removed from the container as completely as possible to ensure subsequent production batches.

[0177] In food, beverage, or pharmaceutical manufacturing, fungal microorganisms of the genera *Chaetomium* or *Arthrinium*, as well as spores or bacteria of the genus *Bacillus* spp., can be significant problems during food bottling, particularly in aseptic bottling processes. Cleaning compositions comprising one or more surfactant compounds disclosed herein can be used to control or significantly reduce (by more than 5 log) the levels of these microorganisms in beverage, food, or pharmaceutical bottling lines using aseptic bottling techniques. 10This method reduces the number of microorganisms belonging to the genera *Chaetomium*, *Arthrinium*, or *Bacillus*. These same microorganisms can be a serious concern during the production of fermented and / or cultured foods (e.g., beer, certain alcoholic beverages, yogurt, etc.), and cleaning compositions containing one or more surfactant compounds disclosed herein can be used to achieve a significant reduction in these harmful microorganisms, prevent contamination of subsequent production batches, and thus significantly reduce waste and contamination incidents.

[0178] In such techniques, cold aseptic filling techniques can be used to fill metal, aluminum, or steel containers, glass bottles or containers, or plastic (PET, PBT, or PEN) bottles or containers, etc. In such methods, the cleaning compositions of this disclosure can be used to sterilize the interior of such food containers prior to filling with food products (e.g., carbonated or non-carbonated beverages). Typical carbonated beverages in this application include, but are not limited to, cola drinks, fruit juice drinks, ginger ale drinks, root beer drinks, iced tea drinks that may be non-carbonated, and other common beverages considered soft drinks. Cleaning compositions containing one or more surfactant molecules of this disclosure can be used to sterilize tanks, pipelines, pumps, and other equipment used for manufacturing and storing such products, and can also be used for bottling or containing food products. In some embodiments, the cleaning compositions of this disclosure can be used to kill both undesirable bacteria and fungal microorganisms that may be present on the surfaces of production equipment and food containers.

[0179] In addition to one or more surfactant molecules disclosed herein, microorganisms can be effectively killed (e.g., >1 log within 30 seconds). 10 Or at most about 5 logs 10 A suitable antimicrobial agent (reduced) may be included in the cleaning composition of this disclosure at a concentration level of at least about 50 ppm. In one embodiment, such an agent, excluding water, will be present at a concentration of about 0.001 to about 1 wt%, for example, about 0.01 to about 0.15 wt%, or about 0.05 to about 0.1 wt%. In some cases, one or more surfactant compounds of this disclosure may exhibit certain microbial killing abilities above certain threshold concentrations. In such cases, one or more surfactant compounds may achieve effective killing of harmful microorganisms alone, without additional antimicrobial agents.

[0180] 3. Surfactants Suitable surfactants for use in cleaning formulations of this disclosure for hard surfaces, such as in-situ cleaning systems (CIP), removal cleaning systems (COP), washer-stain removers, sterilizers, textile washing machines, ultrafiltration and nanofiltration systems, and indoor air filters, comprising one or more surfactant molecules and / or co-surfactant molecules of formula I or II below. Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 It can be selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C of another surfactant molecule having a structure represented by Formula I 12 Linker, wherein the other surfactant molecule of Formula I is the same as or different from the surfactant molecule of Formula I; n and z can be independently selected from any integer from 1 to 12; m can be any integer from 1 to 12; and X can be selected from chlorine, bromine, and iodine.

[0181] Specifically, R 3 Can be selected from C2-C 10 alkenyl, C2-C 10 alkynyl group, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and three-carbon linkers attached to a second molecule of Formula I, wherein the second molecule of Formula I is identical to the first molecule of Formula I.

[0182] More specifically, R 3 You can choose from the following formula: .

[0183] In particular, suitable surfactants or co-surfactants may include any one or more of the surfactants 1-12 described herein.

[0184] 4. Other additional ingredients In some embodiments, the cleaning compositions of this disclosure may contain other additional ingredients. Other ingredients suitable for use with the compositions of this disclosure include, but are not limited to, acidifiers, stabilizers (e.g., chelating agents or sequestrants), buffers, detergents, wetting agents, defoamers, thickeners, foaming agents, curing agents, aesthetic enhancers (i.e., colorants, odorants, or fragrances), and other cleaning agents. These additional ingredients may be pre-formulated with the compositions of this disclosure or added to the system before, after, or substantially simultaneously with the addition of the compositions of this disclosure. Additionally, the cleaning compositions may be used in combination with one or more conventional cleaning agents, such as alkaline detergents. In some instances, the cleaning compositions may include soaps, bleach, or detergents as described herein. Furthermore, the cleaning compositions may also include cosolvents as described herein.

[0185] Acidifier In some embodiments, the cleaning composition comprising one or more surfactant compounds of this disclosure may further comprise an acidifier. The acidifier can act as a catalyst for the conversion of carboxylic acids to peroxycarboxylic acids. The acidifier can effectively form concentrated cleaning compositions with a pH of about 0.01 to about 7 or lower, about 1 to about 6, or about 2 to about 5. The acidifier can effectively form usable compositions with a pH of about 4 to about 9, about 5 to about 8, or about 5.5 to about 7.5. In some embodiments, the acidifier can be used to lower the pH of an alkaline cleaning solution to about 10, about 10 or lower, about 9, about 9 or lower, about 8, about 8 or lower, about 7, about 7 or lower, about 6, or about 6 or lower. In some embodiments, the acidifier comprises an inorganic acid. Suitable inorganic acids include, but are not limited to, sulfuric acid, sodium bisulfate, phosphoric acid, nitric acid, and hydrochloric acid. In some embodiments, the acidifier comprises an organic acid. Suitable organic acids include, but are not limited to, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, xylenesulfonic acid, benzenesulfonic acid, straight-chain alkylbenzenesulfonic acid, cumenesulfonic acid, xylenesulfonic acid, formic acid, acetic acid, glycolic acid, monohalocarboxylic acids, dihalocarboxylic acids or trihalocarboxylic acids, pyridinecarboxylic acid, dipyridinecarboxylic acid and mixtures thereof. In some embodiments, the compositions disclosed herein are free of or substantially free of phosphorus-based acids.

[0186] In some embodiments, the selected acidifier may also be used as a stabilizer. Therefore, the compositions disclosed herein may be substantially free of additional stabilizers.

[0187] In some embodiments, a cleaning composition comprising one or more surfactant compounds of the present disclosure may further comprise about 0.5 to about 80% by weight of an acidifier, about 1 to about 50% by weight, about 5 to about 30% by weight of an acidifier, or about 7 to about 14% by weight of an acidifier. It should be understood that all values ​​and ranges between these values ​​and ranges are covered by the compositions of the present disclosure.

[0188] stabilizer In some embodiments, the cleaning composition comprising one or more surfactant compounds disclosed herein includes one or more stabilizers. Stabilizers can be used, for example, to stabilize peracids and hydrogen peroxide and prevent premature oxidation of these components within the cleaning composition.

[0189] In some embodiments, acidic stabilizers may be used. Therefore, in some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may be substantially free of additional acidifiers.

[0190] Suitable stabilizers include, for example, chelating agents or masking agents. Suitable masking agents include, but are not limited to, organic chelating compounds that mask metal ions in solution, particularly transition metal ions. Such masking agents include organic amino or hydroxy polyphosphonic acid complexing agents (in the form of acids or soluble salts), carboxylic acids (e.g., polymeric polycarboxylate salts), hydroxycarboxylic acids, aminocarboxylic acids, or heterocyclic carboxylic acids, such as pyridine-2,6-dicarboxylic acid (dipyridinecarboxylic acid).

[0191] In some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may further comprise dipicolinic acid as a stabilizer. Such cleaning compositions comprising dipicolinic acid can be formulated to be phosphorus-free or substantially phosphorus-free. It has also been observed that the inclusion of dipicolinic acid in cleaning compositions (e.g., cleaning compositions comprising one or more surfactant compounds of this disclosure) contributes to achieving phase stability of the composition compared to other conventional stabilizers, such as 1-hydroxyethylidene-1,1-diphosphonic acid (CH3C(PO3H2)2OH) (HEDP).

[0192] If a cleaning composition containing one or more surfactant compounds of this disclosure contains at least one nonionic surfactant, particularly a nonionic surfactant having an ethylene oxide (EO) hydrophilic block, and / or when such a composition contains at least one other anionic surfactant and / or some other amine oxide surfactant, the cleaning composition may potentially have a risk of phase separation or visible turbidity or haze. In such cases, a small amount of a co-water solubilizer, such as sodium cumene sulfonate (“SCS”), may be added to the composition. Up to about 10% by weight, up to about 8% by weight, up to about 5% by weight, and up to about 3% by weight of the co-water solubilizer may be added to clarify and / or eliminate phase separation in the cleaning composition formulation.

[0193] In other embodiments, a masking agent may be further added to the cleaning composition comprising one or more surfactant compounds of the present disclosure. Suitable masking agents may include phosphonic acids and / or phosphonates. Examples of phosphonic acids and phosphonates include, but are not limited to: HEDP; ethylenediaminetetramethylenephosphonic acid (EDTMP); diethylenetriaminepentamethylenephosphonic acid (DTPMP); cyclohexane-1,2-tetramethylenephosphonic acid; amino[tris(methylenephosphonic acid)]; (ethylenediamine[tetra(methylenephosphonic acid)]); 2-phosphenebutane-1,2,4-tricarboxylic acid; or salts thereof, such as alkali metal salts, ammonium salts, or alkyl acylamine salts, such as monoethanolamine salts, diethanolamine salts, or tetraethanolamine salts; pyridinecarboxylic acid, dipyridinecarboxylic acid, or mixtures thereof. In some embodiments, organophosphonates, such as HEDP, may be included in the cleaning composition comprising one or more surfactant compounds of the present disclosure.

[0194] Commercially available food additive chelating agents, such as phosphonates sold under the trade name DEQUEST®, may also be incorporated into cleaning compositions comprising one or more surfactant compounds disclosed herein. Such chelating agents include, for example, 1-hydroxyethylidene-1,1-diphosphonic acid, available from Monsanto Industrial Chemicals Co., St. Louis, Mo., under DEQUEST® 2010; amino[tris(methylenephosphonic acid)](N[CH2PО3H2]3)), available from Monsanto under DEQUEST® 2000; ethylenediamine[tetra(methylenephosphonic acid)], available from Monsanto under DEQUEST® 2041; and 2-phosphonobutane-1,2,4-tricarboxylic acid, available from Mobay Chemical Corporation, Inorganic Chemicals Division, Pittsburgh, Pa., under Bayhibit AM, etc.

[0195] Suitable masking agents can be aminocarboxylic acid type masking agents. Suitable aminocarboxylic acid type masking agents include, for example, their acid or alkali metal salts, such as amino acetate and their salts. Suitable aminocarboxylic acid salts may include, but are not limited to: N-hydroxyethylaminodiacetic acid; hydroxyethylenediaminetetraacetic acid; nitrilotriacetic acid (NTA); ethylenediaminetetraacetic acid (EDTA); N-hydroxyethyl-ethylenediaminetriacetic acid (HEDTA); diethylenetriaminepentaacetic acid (DTPA); and alanine-N,N-diacetic acid, etc.; and mixtures thereof.

[0196] In addition, suitable masking agents may include polycarboxylate salts. For example, suitable polycarboxylate salts include, but are not limited to: polyacrylic acid, maleic acid / olefin copolymer, acrylic acid / maleic acid copolymer, polymethacrylic acid, acrylic acid-methacrylic acid copolymer, hydrolyzed polyacrylamide, hydrolyzed polymethacrylamide, hydrolyzed polyacrylonitrile, hydrolyzed polymethacrylonitrile, hydrolyzed acrylonitrile-methacrylonitrile copolymer, polymaleic acid, polyfumaric acid, copolymer of acrylic acid and itaconic acid, phosphino polycarboxylate salts, their acid or salt forms, mixtures thereof, etc.

[0197] In some embodiments, a cleaning composition comprising one or more surfactant compounds of this disclosure may comprise about 0.01 to about 10% by weight of one or more stabilizers, about 0.4 to about 4% by weight of one or more stabilizers, about 0.6 to about 3% by weight of one or more stabilizers, and about 1 to about 2% by weight of one or more stabilizers. It should be understood that this disclosure covers all values ​​and ranges within these values ​​and ranges.

[0198] Wetting or defoaming agents Wetting and defoaming agents can also be used in cleaning compositions comprising one or more surfactant compounds of this disclosure. In addition to the wetting properties provided by the one or more surfactant compounds of this disclosure, wetting agents further enhance surface contact or penetration activity. Wetting agents that can be used in cleaning compositions may include any of those components known in the art for improving the surface activity of materials.

[0199] Generally, defoamers available according to this disclosure include, but are not limited to: silica and silicones; aliphatic acids or esters; alcohols; sulfates or sulfonates; amines or amides; halogenated compounds, such as chlorofluorocarbons; vegetable oils, waxes, mineral oils and their sulfonated or sulfated derivatives; fatty acids and / or soaps thereof, such as alkali metal soaps, alkaline earth metal soaps; and phosphates and phosphate esters, such as alkyl and basic diphosphates, and tributyl phosphates, etc.; and mixtures thereof.

[0200] In some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may include food-grade antifoaming agents or defoamers, particularly if the cleaning composition is used to clean food products, food processing equipment, containers used in the production of food and beverages, and pharmaceuticals. For this purpose, one of the more effective antifoaming agents includes silicones. Silicones such as dimethyl silicone, diol polysiloxanes, cresol polysiloxanes, trialkyl or tetraalkyl silanes, hydrophobic silica defoamers, and mixtures thereof can be used to achieve defoaming. Commercially available defoamers generally include, but are not limited to, silicones, such as Armour Industrial Chemical Company's Ardefoam® (which is a silicone incorporated into an organic emulsion); Krusable Chemical Company's Foam Kill® or Kresseo® (which are silicone-type and non-silicone-type defoamers and silicone esters); and Dow Corning's Anti-Foam A® and DC-200 (both food-grade silicones), etc. The defoamer may be present in a cleaning composition comprising one or more surfactant compounds of the present disclosure in a concentration range of about 0.01% to 20% by weight, about 0.01% to 5% by weight, or about 0.01% to about 1% by weight.

[0201] In some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may include alcohol alkoxylate-based antifoaming agents or defoamers that are stable in acidic environments and / or oxidatively stable. For this purpose, an example of a more effective antifoaming agent is an alcohol alkoxylate having an alcohol chain length of about C8-12, and more specifically C9-11, and having a polyoxypropylene alkoxylate in the entirety or a portion of the alkylene oxide moiety. Common commercially available defoamers of this kind include alkoxylates, such as BASF Degressal, particularly Degressal SD20.

[0202] Thickener or gelling agent Cleaning compositions comprising one or more surfactant compounds of this disclosure may contain any of a variety of known thickeners. Suitable thickeners include, but are not limited to: natural gums, such as xanthan gum, guar gum, or other gums derived from plant mucilage; polysaccharide-based thickeners, such as alginate, starch, and cellulose polymers (e.g., carboxymethyl cellulose); polyacrylate thickeners; and hydrocolloid thickeners, such as pectin. Other suitable thickeners include synthetic materials such as polyacrylates, polyacrylamide, polyalkylene glycols and their derivatives (including polyethylene glycol or polypropylene glycol), polyvinyl derivatives (e.g., polyvinyl alcohol and / or polyvinyl acetate) or copolymers thereof, and other polyvinyl derivatives and mixtures thereof. Polycarboxylic acids may also be used as thickeners. ACUSOL® 445 is a partially neutralized liquid detergent polymer. Other polyacrylic acids with molecular weights of 4500 (CRITERION 2005) and 8000 (CRITERION 2108) are available from Kemira Chemicals (Kennesaw, Ga). Other thickeners include, but are not limited to, SoakalanCP5, Coatex DE185, and Isol Dispersant HN44, all available from BASF. In some embodiments, the included thickeners are non-oxidizable and storage-stable under the pH conditions of this disclosure. In one embodiment, the thickener does not leave contaminating residues on object surfaces. For example, the thickener or gelling agent is compatible with food or other sensitive products in the contact area. Generally, the concentration of thickener used in a cleaning composition comprising one or more surfactant compounds of this disclosure will be governed by the desired viscosity in the final cleaning composition. However, as a general guideline, the viscosity range of the thickener in the composition should be from about 0.1 wt% to about 5 wt%, from about 0.1 wt% to about 1.0 wt%, or from about 0.1 wt% to about 0.5 wt%.

[0203] curing agent Cleaning compositions comprising one or more surfactant compounds disclosed herein may include a curing agent that may participate in maintaining the composition in a solid form. In some embodiments, the curing agent may form and / or maintain the composition in a solid form. In other embodiments, the curing agent may cure the composition without unacceptably impairing the final release of the surfactant compound(s) contained therein. The curing agent may include, for example, an organic or inorganic solid compound having neutral and inert properties or contributing to the functionalization, stabilization, or washing of the cleaning composition. Suitable curing agents include, but are not limited to, solid or paste-like polyethylene glycol (PEG), solid or paste-like polypropylene glycol, solid EO / PO block copolymers, amides, ureas (also known as carbamates), nonionic surfactants (which may be used with coupling agents), anionic surfactants, starches that have been converted to water solubility (e.g., by acid or alkali treatment), cellulose that has been made into water-soluble substances, inorganic reagents, poly(maleic anhydride / methyl vinyl ether), polymethacrylic acid, other generally functional or inert materials having high melting points, mixtures thereof, etc.

[0204] Suitable glycol curing agents include solid polyethylene glycol or solid polypropylene glycol, which may have, for example, a molecular weight of about 1,400 to about 30,000. In some embodiments, the curing agent comprises or is solid PEG, such as PEG 1500 up to PEG 20,000. In some embodiments, PEG includes PEG 1450, PEG 3350, PEG 4500, PEG 8000, PEG 20,000, etc. Suitable solid polyethylene glycol is commercially available from Union Carbide under the trade name CARBOWAX.

[0205] Suitable amide curing agents include stearic acid monoethanolamide, lauric acid diethanolamide, stearic acid diethanolamide, stearic acid monoethanolamide, cocodiethylene amide, alkylamides, and mixtures thereof. In one embodiment, the composition may include a diol (e.g., PEG) and an amide.

[0206] When one or more surfactant compounds included in a cleaning composition comprising one or more surfactant compounds of this disclosure are nonionic surfactants, the curing agent to be used may include nonylphenol ethoxylates, linear alkyl alcohol ethoxylates, ethylene oxide / propylene oxide block copolymers, mixtures thereof, etc. Suitable ethylene oxide / propylene oxide block copolymers include those sold under the trade name Pluronic (e.g., Pluronic 108 and Pluronic F68) and commercially available from BASF Corporation. In some embodiments, the nonionic surfactant included in the cleaning composition comprising one or more surfactant compounds of this disclosure may be a nonionic surfactant that is solid at room temperature or at the temperature in which the cleaning composition is stored or used. In other embodiments, the nonionic surfactant may be selected as a surfactant that has reduced water solubility when combined with a coupling agent. Suitable coupling agents that can be used with nonionic surfactant curing agents include propylene glycol, polyethylene glycol, mixtures thereof, etc.

[0207] When one or more surfactant compounds included in a cleaning composition comprising one or more surfactant compounds of the present disclosure are anionic surfactants, the curing agent to be used may include linear alkylbenzene sulfonates, alcohol sulfates, alcohol ether sulfates, α-olefin sulfonates, mixtures thereof, etc. In one embodiment, the curing agent is or may include a linear alkylbenzene sulfonate. In one embodiment, the anionic surfactant included in the cleaning composition comprising one or more surfactant compounds of the present disclosure may be a surfactant that is solid at room temperature or at the temperature at which the cleaning composition is stored or used.

[0208] Suitable inorganic curing agents include, but are not limited to, phosphates (e.g., alkali metal phosphates), sulfates (e.g., magnesium sulfate, sodium sulfate, or sodium bisulfate), acetates (e.g., anhydrous sodium acetate), borates (e.g., sodium borate), silicates (e.g., in precipitated or calcined form, e.g., Sipernat 50® from Degussa), carbonates (e.g., calcium carbonate or calcium carbonate hydrate), other known hydrateable compounds, mixtures thereof, etc. In some embodiments, the inorganic curing agent may include organophosphonate compounds and carbonates, such as type E compositions.

[0209] In some embodiments, a cleaning composition comprising one or more surfactant compounds of this disclosure may include any agent or combination of agents that provide the necessary degree of curing and water solubility in such a composition. In other embodiments, increasing the concentration of the curing agent in the cleaning composition may increase the hardness of the composition. In still other embodiments, decreasing the concentration of the curing agent may loosen or soften the cleaning composition. In practice, the use and amount of these agents can be applied and adjusted to achieve the desired form of the cleaning composition.

[0210] In some embodiments, the curing agent may comprise any organic or inorganic compound that imparts a solid character to the cleaning composition and / or controls its soluble character, said cleaning composition comprising one or more surfactant compounds of this disclosure, for example, when placed in an aqueous environment. For example, if the curing agent has greater water solubility compared to other components in the composition, it can provide controlled dispensing. Urea can be such a curing agent. By another example, organic nonionic or amide curing agents may be suitable for systems that may benefit from lower water solubility or slower dissolution rates.

[0211] In some embodiments, a cleaning composition comprising one or more surfactant compounds of the present disclosure may include a curing agent that provides ease of processing or manufacture. For example, the curing agent may be selected to form a composition that can be cured into a solid form at an ambient temperature of about 30°C to about 50°C after mixing has stopped, and the mixture is dispensed from the mixing system in about 1 minute to about 3 hours, or about 2 minutes to about 2 hours, or about 5 minutes to about 1 hour.

[0212] Cleaning compositions comprising one or more surfactant compounds disclosed herein may include any effective amount of curing agent. The amount of curing agent included in such compositions may vary depending on the type of composition, the components included in the composition, the intended use of the composition, the amount of dispensing solution applied to the solid composition over time during use, the temperature of the dispensing solution, the hardness of the dispensing solution, the intended physical dimensions of the solid cleaning composition, the concentration of other components, the concentration of the cleaning component in the composition, and other similar factors. Suitable amounts may be from about 1 to about 99% by weight, from about 1.5% to about 85% by weight, from about 2% to about 80% by weight, from about 10% to about 45% by weight, from about 15% to about 40% by weight, from about 20% to about 30% by weight, from about 30% to about 70%, from about 40% to about 60%, up to about 50% by weight, and from about 40% to about 50%.

[0213] carrier In some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may include a carrier. The carrier provides a medium for dissolving, suspending, or carrying other components of such compositions. For example, a carrier can provide a medium for the solubilization, suspension, or production of sulfonated peroxycarboxylic acids and for forming equilibrium mixtures. The carrier can also serve to deliver and wet the compositions of this disclosure onto objects. For this purpose, the carrier may contain any or more components capable of promoting these functions.

[0214] In some embodiments, the support may primarily comprise water, which facilitates dissolution and serves as a medium for reaction and equilibrium. Alternatively, the support may comprise or primarily comprise an organic solvent, such as a simple alkyl alcohol, like ethanol, isopropanol, n-propanol, benzyl alcohol, etc. Polyols are also useful supports, including but not limited to glycerol, sorbitol, etc.

[0215] Suitable carriers may include glycol ethers. Suitable glycol ethers include, but are not limited to: diethylene glycol n-butyl ether, diethylene glycol n-propyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, diethylene glycol tert-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol propyl ether, dipropylene glycol tert-butyl ether, ethylene glycol butyl ether, ethylene glycol propyl ether, ethylene glycol ethyl ether, ethylene glycol methyl ether acetate, propylene glycol n-butyl ether, propylene glycol ethyl ether, propylene glycol methyl ether, propylene glycol n-propyl ether, tripropylene glycol methyl ether and tripropylene glycol n-butyl ether, ethylene glycol phenyl ether (commercially available from Dow Chemical Company under DOWANOL EPH™), propylene glycol phenyl ether (commercially available from Dow Chemical Company under DOWANOL PPH™), etc., or mixtures thereof. Other suitable commercially available glycol ethers (all available from Union Carbide Corp.) include, but not limited to: butoxyethyl PROPASOL™, butyl CARBITOL™ acetate, butyl CARBITOL™, butyl CELLOSOLVE™ acetate, butyl CELLOSOLVE™, butyl DIPROPASOL™, butyl PROPASOL™, CARBITOL™ PM-600, CARBITOL™ low specific gravity, CELLOSOLVE™ acetate, CELLOSOLVE™, EEP™ ester, FILMER IBT™, hexyl CARBITOL™, hexyl CELLOSOLVE™, methyl CARBITOL™, methyl CELLOSOLVE™ acetate, methyl CELLOSOLVE™, methyl DIPROPASOL™, methyl PROPASOL™ acetate, methyl PROPASOL™, propyl CARBITOL™, propyl CELLOSOLVE™, propyl DIPROPASOL™, and propyl PROPASOL™.

[0216] In some embodiments, the carrier may constitute a large portion of the cleaning composition comprising one or more surfactant compounds of this disclosure, and may even be the remainder of the entire composition excluding surfactants, antimicrobial agents, oxidants, additives, etc. The carrier concentration and type will depend on the properties of the composition as a whole, environmental storage, and application methods (including the concentrations of other components), among other factors.

[0217] In some embodiments, a cleaning composition comprising one or more surfactant compounds of the present disclosure may comprise about 5% to about 90% by weight of a carrier, about 10% to about 80% by weight of a carrier, about 20% to about 60% by weight of a carrier, or about 30% to about 40% by weight of a carrier. It should be understood that all values ​​and ranges between these values ​​and ranges are covered by the present disclosure.

[0218] Other functional ingredients In some embodiments, the cleaning composition comprising one or more surfactant compounds of this disclosure may include additional functional ingredients. Suitable additional functional ingredients included in the composition may be one or more of the following, but not limited to, optical brighteners, dirt redeposition agents, antifoaming agents, low-foaming surfactants, defoaming surfactants, pigments and dyes, softeners, antistatic agents, anti-wrinkle agents, dye transfer inhibitors / color protectants, odor removers / odor traps, dirt shielders / dirt releasers, UV protectants, fragrances, disinfectants, bactericides, waterproofing agents, insect repellents, anti-pilling agents, souring agents, mold removers, anti-allergens, and mixtures thereof. In some embodiments, the one or more additional functional ingredients are formulated into the composition. In other embodiments, the one or more additional functional ingredients are added separately during the cleaning process.

[0219] Color stabilizer In some embodiments, the cleaning composition comprising one or more surfactant compounds of this disclosure may optionally include a color stabilizer. The color stabilizer may be any component included to inhibit discoloration or browning of the composition. In some embodiments, the color stabilizer may be included in the composition in amounts of about 0.01 to about 5% by weight, about 0.05 to about 3% by weight, and about 0.10 to about 2% by weight.

[0220] Optical brightener In some embodiments, the cleaning composition comprising one or more surfactant compounds of this disclosure may optionally include an optical brightener. The brightener is added to the laundry detergent to replace the brightener removed during washing and to make the clothes appear cleaner. The optical brightener may include dyes that absorb light in the ultraviolet and violet regions of the electromagnetic spectrum (typically 340-370 nm) and re-emit light in the blue region (typically 420-470 nm). These additives are typically used to enhance the appearance of fabric colors, causing a perceived “whitening” effect by increasing the total amount of reflected blue light to make the material appear less yellow. In some embodiments, suitable optical brighteners included in the composition may include, but are not limited to, triazine-stilbene (di-, tetra-, or hexa-sulfonated), coumarin, imidazoline, diazole, triazole, benzoxazoline, biphenyl-stilbene, and mixtures thereof. One or more optical brighteners may be used in the composition. In some embodiments, the optical brightener is included in the composition in an amount of about 0.1 to about 5% by weight, about 0.15 to about 3% by weight, or about 0.2 to about 2% by weight. Examples of commercially available optical brighteners suitable for the composition include, but are not limited to, DMS-X and CBS-X, stilbene biphenyl derivatives, both of which are available from Vesta-Intracon BV.

[0221] Anti-redeposition agent In some embodiments, cleaning compositions comprising one or more surfactant compounds of this disclosure may optionally include an anti-redeposition agent. It is not desired to be bound by any particular theory that anti-redeposition agents help prevent loose dirt from being redeposited onto clean fabrics. Anti-redeposition agents may be made from composite cellulose materials such as carboxymethyl cellulose (CMC) or synthetic materials such as polyethylene glycol and polyacrylates. In other embodiments, polyphosphate builders may be included as anti-redeposition agents.

[0222] This disclosure lists formulations comprising at least one surfactant of formula I or II for use in various cleaning products. The following disclosures of compounds of formula I and II apply to compounds of formula I and II in any of the disclosed uses and formulations set forth herein.

[0223] Other compounds provided by this disclosure are those of formula I, wherein R1 and R2 are methyl groups.

[0224] Other compounds provided by this disclosure are compounds of formula I, wherein n and / or z is 5.

[0225] As used in this article, the phrase "n can be an integer from 1 to 12" means that n can be equal to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0226] As used herein, the phrase “C1-C6 alkyl” refers to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5 and / or 6 carbons.

[0227] As used herein, the phrase “C1-C6 linker” refers to a straight-chain or branched alkyl chain containing 1, 2, 3, 4, 5 and / or 6 carbons.

[0228] As used herein, the phrase “C2-C10 alkenyl” refers to a straight-chain or branched alkenyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0229] As used herein, the phrase “C2-C10 alkynyl” refers to a straight-chain or branched alkynyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0230] As used herein, the phrase “C2-C12 ester” refers to a straight-chain or branched ester group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbons.

[0231] As used herein, the phrase “C2-C12 alkoxyalkyl ether” refers to a straight-chain or branched alkoxyalkyl ether group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbons.

[0232] As used herein, the phrase “C1-C10 hydroxyl” refers to a hydroxyl group attached to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0233] As used herein, the phrase “C3-C8 carboxylic acid” refers to a carboxylic acid group attached to a straight-chain or branched alkyl group containing 3, 4, 5, 6, 7 and / or 8 carbons.

[0234] As used herein, the phrase “C1-C10 alkylbenzoic acid” refers to a benzoic acid group attached to a straight-chain or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbons.

[0235] As used in this article, the phrase “n and z can be independently selected from any integer from 1 to 12” means that n and z can be independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0236] As used in this article, the phrase "m can be any integer from 1 to 12" means that m can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0237] As used in this article, the phrase "q can be any integer from 1 to 10" means that q can be 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10.

[0238] A specific compound disclosed herein and referred to herein as surfactant 1 is N-benzyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0239] The second specific compound disclosed herein, and referred to herein as surfactant 2, is N-(2-ethoxy-2-oxoethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0240] The third specific compound disclosed herein and referred to herein as surfactant 3 is N-allyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0241] The fourth specific compound disclosed herein and referred to herein as surfactant 4 is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxo-N-(prop-2-yn-1-yl)hex-1-ammonium bromide, having the following formula: .

[0242] The fifth specific compound disclosed herein, and referred to herein as surfactant 5, is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-(2-methoxyethoxy)ethyl)-N,N-dimethyl-6-oxohexyl-1-ammonium bromide, having the following formula: .

[0243] The sixth specific compound disclosed herein and referred to herein as surfactant 6 is N-(3-(diethoxyphosphoryl)propyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0244] The seventh specific compound disclosed herein and referred to herein as surfactant 7 is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(3-hydroxypropyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0245] The eighth specific compound disclosed herein and referred to herein as surfactant 8 is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-6-oxohex-1-ammonium iodide, having the following formula: .

[0246] The ninth specific compound disclosed herein and referred to herein as surfactant 9 is N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0247] The tenth specific compound disclosed herein, and referred to herein as surfactant 10, is N. 1 N 3 -bis(6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-6-oxohexyl)-N 1 N 1 N 3 N 3 -Tetramethylpropane-1,3-diammonium dibromide, having the following formula: .

[0248] Another group of specific compounds provided in this disclosure and referred to herein as surfactants 11-12 have the following general formula: Where q can be an integer from 1 to 10.

[0249] The eleventh specific compound disclosed herein and referred to herein as surfactant 11 is N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0250] The twelfth specific compound provided in this disclosure and referred to herein as surfactant 12 is N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide, having the following formula: .

[0251] These compounds can be synthesized by a variety of methods. One such method involves reacting an amino acid (e.g., an N-alkylated or N-acylated amino acid) with a siloxane to convert the C-terminus of the amino acid into a desired siloxane derivative. For example, the N-terminus of the amino acid can be further alkylated to produce a quaternary amine.

[0252] Amino acids can be naturally occurring or synthetic, or they can be derived from the ring-opening reaction of lactams such as caprolactam. The ring-opening reaction can be acid- or base-catalyzed, and an example of an acid-catalyzed reaction is shown in Scheme 1 below.

[0253] Option 1 Amino acids may have as few as one or as many as 12 carbons between their N- and C-termini, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons. The alkyl chain may be branched or straight. The alkyl chain may be interrupted by nitrogen, oxygen, or sulfur. The alkyl chain may be further substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carboxyl, and carboxylate groups. The N-terminal nitrogen may be acylated or alkylated by one or more alkyl groups. For example, an amino acid may be 6-(dimethylamino)hexanoic acid.

[0254] Siloxanes can be substituted with one or more alkoxy groups, such as methoxy, ethoxy, isopropoxy, tert-butoxy, etc. Siloxanes can be further substituted with one or more alkyl groups (e.g., propyl), wherein the alkyl groups can be further substituted with suitable functional groups (e.g., nitrogen) to allow the siloxane to couple with amino acids. For example, a siloxane can be 3-aminopropyltris(trimethylsiloxy)silane.

[0255] As shown in Scheme 2 below, siloxane derivatives of amino acids can be synthesized. As indicated, 6-aminohexanoic acid can be alkylated at the N-terminus by treatment with formaldehyde in formic acid under reflux to obtain 6-(dimethylamino)hexanoic acid. The free carboxylic acid is then coupled to 3-aminopropyl(trimethylsiloxy)silane in refluxed toluene to obtain the desired siloxane derivative.

[0256] Option 2 The N-terminal nitrogen can be further derivatized to alter or improve water solubility and surface activity properties. The sample synthesis scheme is shown below in Scheme 3, where the N-terminal nitrogen is alkylated to provide a quaternary amine.

[0257] Option 3 Suitable alkylating agents may include, for example, benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonates, 3-iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6-bromohexanoic acid, 4-(4-bromobutyl)benzoic acid, and 4-(bromomethyl)benzoic acid. Two molecules of Formula I can be linked by treating the N-terminal nitrogen with a bifunctional alkylating agent (e.g., 1,3-dibromopropane).

[0258] The compounds disclosed herein exhibit surface-active properties. These properties can be measured and described by various methods. One way to describe surfactants is through the critical micelle concentration (CMC) of the molecule. The CMC can be defined as the concentration of surfactant at which micelles form, and above this concentration, all other surfactants will be incorporated into the micelles.

[0259] As the surfactant concentration increases, the surface tension decreases. Once the surface is completely covered by surfactant molecules, micelles begin to form. This point represents the center of gravity (CMC) and the minimum surface tension. Further addition of surfactant will not further affect the surface tension. Therefore, the CMC can be measured by observing the change in surface tension with surfactant concentration. One method for measuring this value is the Wilhelmy plate method. The Wilhelmy plate is typically a thin iridium-platinum plate, which is attached to a balance by a thread and placed perpendicular to the air-liquid interface. The balance is used to measure the force applied to the plate through wetting. The surface tension (γ) is then calculated using this value according to Equation 1: Equation 1: γ = F / l cos θ Where l equals the wetted perimeter (2w + 2d, where w and d are the thickness and width of the plate, respectively), and cos θ (i.e., the contact angle between the liquid and the plate) is assumed to be 0 in the absence of existing literature values.

[0260] Another parameter used to evaluate surfactant performance is dynamic surface tension. Dynamic surface tension is the surface tension value for a given surface or interface age. In the case of a liquid with added surfactant, this may differ from the equilibrium value. Immediately after surface formation, the surface tension is equal to that of the pure liquid. As mentioned above, the surfactant reduces the surface tension; therefore, the surface tension decreases until an equilibrium value is reached. The time required to reach equilibrium depends on the surfactant's diffusion and adsorption rates.

[0261] One method for measuring dynamic surface tension relies on a bubble pressure tensiometer. This device measures the maximum internal pressure of a bubble forming in a liquid via a capillary. The measured value corresponds to the surface tension at a given surface age, calculated from the start of bubble formation to the attainment of the maximum pressure. The dependence of surface tension on surface age can be measured by varying the rate of bubble formation.

[0262] Surfactant compounds can also be evaluated by their wetting ability on solid substrates, such as by measuring the contact angle. When a droplet comes into contact with a solid surface in a third medium (e.g., air), a triple line is formed between the liquid, gas, and solid. The angle between the unit vector of surface tension acting on the triple line and tangent to the droplet and the surface is described as the contact angle. The contact angle (also called the wetting angle) is a measure of how a solid is wetted by a liquid. In the case of complete wetting, the liquid spreads completely over the solid, and the contact angle is 0°. The wetting properties of a given compound are typically measured at concentrations of 1–100 × CMC; however, it is not a concentration-dependent property. Therefore, wetting properties can be measured at higher or lower concentrations.

[0263] In one method, an optical contact angle goniometer can be used to measure the contact angle. This device uses a digital camera and software to extract the contact angle by analyzing the profile shape of a droplet attached to a surface.

[0264] Potential applications of the surfactant compounds disclosed herein include formulations used as shampoos, hair conditioners, detergents, spot-free rinsing solutions, floor and carpet cleaners, graffiti removers, wetting agents for crop protection, adjuvants for crop protection, and wetting agents for aerosol spray coatings.

[0265] Those skilled in the art will understand that small differences between compounds can lead to substantially different surfactant properties, allowing different compounds to be used with different substrates in different applications. Those skilled in the art will further understand that surfactant properties may not be predictable based on chemical structure, as further explained below. For example, surfactant 9 and a comparative surfactant, differing only in the number of methylene groups in R3, exhibit different surfactant properties. Surprisingly, surfactant 9 exhibits excellent activity, as further described below, while the comparative surfactant exhibits poor surfactant properties.

[0266] The following non-limiting embodiments are provided to illustrate the different properties of various surfactants. In Table 1 below, the short names of surfactants are associated with their corresponding chemical structures.

[0267] In any formulation considered in this disclosure, these compounds are effective as surfactants for use as wetting or foaming agents, dispersants, emulsifiers, and detergents.

[0268] The amounts of the compounds disclosed herein for use in formulations may be as low as about 0.001 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, or about 5 wt.%, or as high as about 8 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, or about 25 wt.%, about 30 wt.%, about 40 wt.%, about 50 wt.%, about 80 wt.%, or in any range from 0.001 wt.% to 80 wt.%, or 0.05 wt.% to 50 wt.%, or 0.1 wt.% to 20 wt.%, or 0.5 wt.% to 10 wt.%, or 1 wt.% to 8 wt.%, or 2 wt.% to 8 wt.%, or 5 wt.% to 8 wt.%, or in any range using any two of the foregoing values.

[0269] Table 2 includes comparative surfactants, which include their names and structures.

[0270] The surfactant used in the formulations disclosed herein may have a critical micelle concentration (CMC) of less than about 15 mmol, less than about 10 mmol, less than about 5 mmol, less than about 1 mmol, less than about 0.8 mmol, less than about 0.7 mmol, less than about 0.6 mmol, less than about 0.5 mmol, less than about 0.4 mmol, less than about 0.3 mmol, less than about 0.2 mmol, less than about 0.1 mmol, less than about 0.05 mmol, or less than about 0.01 mmol, or may have any CMC falling within the range covered by the aforementioned endpoints. For example, the surfactant may have a CMC of about 0.01 to about 15 mmol, about 0.05 to about 10 mmol, or about 0.1 to about 5 mmol.

[0271] The surfactant used in the formulations disclosed herein may have a plateau value of minimum surface tension of less than about 25 mN / m, less than about 24 mN / m, less than about 23 mN / m, less than about 22 mN / m, less than about 21 mN / m, less than about 20 mN / m, less than about 19 mN / m, less than about 18 mN / m, less than about 17 mN / m, less than about 16 mN / m, or less than about 15 mN / m, or may have any plateau value of minimum surface tension falling within the range covered by the aforementioned endpoints. For example, the surfactant may have a plateau value of minimum surface tension of about 15 to about 25 mN / m, about 18 to about 22 mN / m, or about 20 to about 21 mN / m.

[0272] Surfactants with antimicrobial activity The cell is the basic unit of all living organisms, each possessing its own set of organelles responsible for performing various functions and storing genetic information for the organism's development and function. The cell's outer boundary is called the cell membrane, which acts as a barrier and regulates the transport of substances between the inside and outside of the cell. The cell membrane can be disrupted through a process called lysis, leading to cell death, which is essentially the basis of all antimicrobial processes. The use of surfactants (which have intrinsic biocidal activity) for cleaning surfaces, food, and various other applications can be very important, especially when cleaning processes cannot tolerate the use of chemical biocides.

[0273] Traditionally, cationic surfactants have been used as antimicrobial agents in industries such as the food industry and hospitals. Unlike conventional antimicrobial chemicals that rely on a "lock-and-key" mechanism, cationic surfactants are known to exert their antimicrobial activity by disrupting bacterial membranes via electrostatic and hydrophobic interactions. (Zhou & Wang, Structure-activity relationship of cationic surfactants as antimicrobial agents., Current Opinion in Colloids & Interface Science, 45:28-43 (2020)). For a surfactant to be effective as an antimicrobial agent, it must kill bacteria or other unwanted pathogens without interfering with mammalian cells. Currently, with increasing awareness of the potential cytotoxicity and environmental hazards posed by certain chemicals, efforts are also being made to develop surfactants that reduce the cytotoxicity problem, which may arise from the lack of selectivity of conventional quaternary ammonium surfactants, which are known to indiscriminately disrupt biofilms regardless of cell type.

[0274] The surfactants disclosed herein have been demonstrated in a standard protocol for evaluating antimicrobial activity, known as the minimum inhibitory concentration (MIC) test. The table below shows the MIC results for examples of the surfactants disclosed herein. Example

[0275] Nuclear magnetic resonance (NMR) spectroscopy was performed on a Bruker 500 MHz spectrometer. Critical micelle concentration (CMC) was determined at 23 °C using the Wilhelmy plate method with a tensiometer equipped with Pt-Ir plates (DCAT 11, DataPhysics Instruments GmbH). Dynamic surface tension was determined at 23 °C using a bubble pressure tensiometer (Krüss BP100, Krüss GmbH). Contact angle was determined using an optical contact angle goniometer equipped with a digital camera (OCA 15 Pro, DataPhysics GmbH).

[0276] Example 1: 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) Synthesis of 3-trisiloxane-3-yl)propyl)hexamamide In a 100 mL round-bottom boiling flask equipped with a Dean Stark trap, 2.00 g (12.56 mmol, 1 equivalent) of 6-(dimethylamino)hexanoic acid was dissolved in 50 mL of toluene, followed by the addition of 5.48 mL (13.81 mmol, 1.1 equivalent) of 3-aminopropyltris(trimethylsiloxy)silane. The reaction vessel was heated and the reaction was refluxed for 24 hours until no more water separation occurred in the Dean Stark tube. The solvent was removed under vacuum to give the desired siloxane derivative as a yellow oil in 94% yield. 1 H NMR (500 MHz, DMSO) δ : 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J = 7.3 Hz, 2H), 2.00 (s, 6H), 2.06 – 2.03 (m, 2H), 2.89 (dd, J = 12.9, 6.8 Hz, 2H).

[0277] Example 2a: N-benzyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)tri Synthesis of siloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexyl-1-ammonium bromide (surfactant 1) The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Benzyl bromide (518 mg, 3.03 mmol) was added, and the mixture was heated to 70 °C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with acetone to remove excess benzyl bromide, yielding surfactant 1 (1.1 g) as a yellow solid.

[0278] Example 2b: Determination of the physical properties of surfactant 1 The critical micelle concentration (CMC) of surfactant 1 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 9.883 mmol at pH 8. The minimum surface tension plateau achievable by this surfactant is approximately 20.67 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 1 The figure shows surface tension as a function of concentration.

[0279] Example 3a: N-(2-ethoxy-2-oxoethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl) Silyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant) Synthesis of Agent 2) The siloxane derivative (1 g, 2.02 mmol) described in Example 1 was dissolved in DMF (15 mL), and ethyl bromoacetate (0.25 mL, 2.4 mmol) was added. The mixture was stirred at 70 °C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to obtain surfactant 2 (900 mg) in the form of a brown liquid.

[0280] Example 3b: Determination of the physical properties of surfactant 2 The critical micelle concentration (CMC) of surfactant 2 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.2171 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.36 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 2 The figure shows surface tension as a function of concentration.

[0281] Example 4a: N-allyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)) Synthesis of trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium iodide (surfactant 3) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was added to acetonitrile (10 mL), followed by sodium carbonate (0.26 g), and then allyl iodine (674 mg). The reaction was refluxed at 40 °C for 14 hours. Residual sodium carbonate was removed by filtration and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess allyl iodine to give surfactant 3 (850 mg) as a brown liquid.

[0282] Example 4b: Determination of the physical properties of surfactant 3 The critical micelle concentration (CMC) of surfactant 3 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 1.3599 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.67 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 3 The figure shows surface tension as a function of concentration.

[0283] Example 5a: 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane- 3-(propyl)amino)-N,N-dimethyl-6-oxo-N-(prop-2-yn-1-yl)hex-1-ammonium bromide (surfactant 4) Synthesis The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Propylene bromide (674 mg, 2.4 mmol) was added, and the mixture was stirred at 70 °C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to obtain surfactant 4 (850 mg) in the form of a brown liquid.

[0284] Example 5b: Determination of the physical properties of surfactant 4 The critical micelle concentration (CMC) of surfactant 4 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.2419 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.54 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 4 The figure shows surface tension as a function of concentration.

[0285] Example 6a: 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane- 3-(2-(2-methoxyethoxy)ethyl)-N,N-dimethyl-6-oxohexyl-1-ammonium bromide (Table) Synthesis of surfactant 5) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). 1-Bromo-2-(2-methoxyethoxy)ethane (2.4 mmol) was added, and the mixture was stirred at 70 °C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to obtain surfactant 5 (800 mg) as a brown liquid.

[0286] Example 6b: Determination of the physical properties of surfactant 5 The critical micelle concentration (CMC) of surfactant 5 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.4622 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.40 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 5 The figure shows surface tension as a function of concentration.

[0287] Example 7a: N-(3-(diethoxyphosphoryl)propyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl)propane) Methylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (table) Synthesis of surfactant 6) The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (20 mL). Bromophosphonate (4.04 mmol) was added, and the mixture was stirred at 70 °C for 12 hours. The solvent was removed under vacuum, and the crude product was washed twice with hexane to obtain surfactant 6 (900 mg) as a brown liquid.

[0288] Example 7b: Determination of the physical properties of surfactant 6 The critical micelle concentration (CMC) of surfactant 6 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.3989 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.48 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 6 The figure shows surface tension as a function of concentration.

[0289] Example 8a: 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane- Synthesis of 3-(3-hydroxypropyl)-N,N-dimethyl-6-oxohexyl-1-ammonium iodide (surfactant 7) become The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in acetonitrile (10 mL). Sodium carbonate (0.26 g) was added, followed by 3-iodopropanol (674 mg). The mixture was stirred at 40 °C for 24 hours. Residual alkali was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess iodopropanol and give surfactant 7 (780 mg) as a brown liquid.

[0290] Example 8b: Determination of the physical properties of surfactant 7 The critical micelle concentration (CMC) of surfactant 7 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.4568 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.61 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 7 The figure shows surface tension as a function of concentration.

[0291] Example 9a: 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane- Synthesis of 3-(2-hydroxyethyl)-N,N-dimethyl-6-oxohexyl-1-ammonium iodide (surfactant 8) become The siloxane derivative (1.00 g, 2.02 mmol) described in Example 1 was dissolved in acetonitrile (10 mL). 2-Iodoethanol (4.04 mmol) was added, and the mixture was stirred at 40 °C for 14 hours. The solvent was removed, and the crude product was washed twice with hexane to obtain surfactant 8 (910 mg).

[0292] Example 9b: Determination of the physical properties of surfactant 8 The critical micelle concentration (CMC) of surfactant 8 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.9986 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.41 mN / m, indicating that the surfactant possesses outstanding interfacial activity. These results are presented in... Figure 8 The figure shows surface tension as a function of concentration.

[0293] Example 10a: N 1 N 3 -bis(6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy) Trisiloxane-3-yl)propyl)amino)-6-oxohexyl)-N 1 N 1 N 3 N 3 -Tetramethylpropane-1,3-diammonium dibromide Synthesis of (surfactant 10) The siloxane derivative (1.00 g, 2.02 mmol) described in Example 1 was dissolved in dimethylformamide (DMF) (20 mL). 1,2-Dibromopropane (1 mmol) was added, and the mixture was stirred at 70 °C for 12 hours. The solvent was removed, and the crude product was washed twice with hexane to obtain surfactant 10 (900 mg) in the form of a brown liquid.

[0294] Example 10b: Determination of the physical properties of surfactant 10 The critical micelle concentration (CMC) of surfactant 10 was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.0631 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 22.12 mN / m, indicating that the surfactant possesses interfacial activity. These results are presented in... Figure 10 The figure shows surface tension as a function of concentration.

[0295] Example 11a: N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilane) Trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 9) Synthesis The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL), and 6-bromohexanoic acid (2.02 mmol) was added. The mixture was stirred at 70 °C for 12 hours, after which the solvent was removed under vacuum. The crude product was washed twice with hexane to provide N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (650 mg) as a viscous brown liquid.

[0296] Example 11b: Determination of the physical properties of surfactant 9 The critical micelle concentration (CMC) of surfactant 9a was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 0.2237 mmol. The minimum surface tension plateau achievable by this surfactant is approximately 20.52 mN / m, indicating that the surfactant possesses excellent interfacial activity. These results are presented in... Figure 9 The figure shows surface tension as a function of concentration.

[0297] Comparative Example A1: N-(carboxymethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)) (Oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (comparative surfactant) Synthesis The siloxane derivative (1.00 g, 2.02 mmol) described in Example 1 was dissolved in dimethylformamide (DMF) (15 mL). Bromoacetic acid (2.02 mmol) was added, and the mixture was stirred at 70 °C for 12 hours. The solvent was removed, and the crude product was washed twice with hexane to obtain surfactant 9b (700 mg) in the form of a brown liquid.

[0298] Comparative Example A2: Determination of the physical properties of the comparative surfactant The critical micelle concentration (CMC) of surfactant 9b was measured. Based on the change in surface tension with concentration in water, the CMC was determined to be approximately 17.28 mmol. The minimum achievable surface tension plateau value for this surfactant is approximately 29.16 mN / m. These results are presented in... Figure 11 The figure is plotted as surface tension relative to concentration. The results demonstrate the difficulty in predicting surfactant activity based on chemical structure; surfactant 9, which differs only in the number of methylene groups in its carboxylic acid, exhibits excellent activity.

[0299] Example 12: N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethyl) Silyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant) Synthesis of Agent 11 4-(4-bromobutyl)benzoic acid was added to the siloxane derivative described in Example 1 to provide N-(4-(4-carboxyphenyl)butyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide.

[0300] Example 13: N-(4-Carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)) (Oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide (surfactant 12) synthesis 4-(bromomethyl)benzoic acid was added to the siloxane derivative described in Example 1 to provide N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohex-1-ammonium bromide.

[0301] Example 14 Soap containing two or more surfactants of the present invention Detergent formulations comprising soap, fully saturated laurel soap granules based on Prifac 5808 from Uniqema, a first inventive surfactant, and a nonionic inventive surfactant. All formulations contain 1.008 g / L of surfactant and 0.25 to 0.67 g / L of soap. Water is conditioned with a mixture of CaCl₂(2H₂O) and MgCl₂(H₂O) to meet calcium and magnesium requirements.

[0302] Example 15 Dry cleaning agents Contact the garment with the low-water-based dry cleaning composition A below (see Table 3) and agitate at 20°C for 15 minutes, using a liquid-to-cloth ratio of 13. Then remove the dry cleaning composition and rinse the garment with a rinsing composition containing a clean dry cleaning solvent. Repeat the experiment with the low-water-based dry cleaning composition BF below (see Table I) using a liquid-to-cloth ratio of 5.

[0303] Example 16 Cleaning compositions suitable for food contact Exemplary formulations illustrating certain embodiments of the cleaning composition can generally be formulated by adding the components to a suitably sized container at room temperature without a specific order. If any component is solid, thick, or gel-like at room temperature, it can be heated to make it a pourable liquid before being added to the container. Mixing of the components is achieved by using a mechanical agitator with a small-diameter propeller at the end of its rotating shaft. Mixing is maintained for a period typically from 5 to 120 minutes until the particular exemplary formulation appears homogeneous. The exemplary compositions are easy to pour and maintain good mixing properties (i.e., a stable mixture) after a prolonged standing period.

[0304] Exemplary aqueous compositions may include one or more surfactants 1-12 disclosed herein, optionally in low concentrations of lower alcohols, and fragrances. The compositions may be further optimized for phase stability (i.e., maintenance of a single phase). The compositions may also contain 0.1 to 0.6% isopropanol. The balance of the composition is water.

[0305] Table 15 .

[0306] Example 17 In-situ clean sample preparation Exemplary formulations suitable for in-situ cleaning applications can typically be prepared by adding the components shown in Table 16 below (in weight %) in no particular order to a suitably sized container at room temperature.

[0307] Table 16 CIP Sample Compositions [% of Components] .

[0308] Example 18 Antimicrobial MIC research The antimicrobial properties of surfactants can be studied using known methods and standard protocols, as well as with a wide variety of microorganisms that serve as treatment targets. Generally, standard protocols can be developed to assess the minimum inhibitory concentration (MIC) of antimicrobial growth using serial dilution methods, yielding concentration-dependent measurements of microbial growth inhibition against Gram-positive bacteria (e.g., anaerobic Streptococcus mutans, and Staphylococcus aureus, which is typically aerobic but can also grow anaerobically) and Gram-negative bacteria (e.g., anaerobic Escherichia coli, or aerobic Pseudomonas aeruginosa).

[0309] The bacteria were multiplied overnight in a suitable growth medium (e.g., trypsin-soy broth). Prior to testing, the concentration of the test organism was determined using a spectrophotometer capable of measuring optical density. Those bacterial samples were then diluted to approximately 1E3 to 1E4 CFU / mL. Subsequently, 10 μL of the prepared bacterial culture was inoculated into the test wells of a 96-well plate, each well containing a suitable growth medium, such as trypsin-soy agar. Once inoculated, the wells were treated with test samples, serially diluted, and incubated at 37 ± 1 °C and a relative humidity of at least 90% for approximately 24 ± 1 hour.

[0310] Prepare a dilution series of the test surfactant. Perform all dilutions sequentially in a 96-well microtiter plate using a multichannel pipette. The dilution series is typically determined by a range-determining test to identify the upper limit of the high concentration and a series of lower concentrations in the dilutions to ensure that the test substance does not completely inhibit bacterial growth at any given time but still shows an effect.

[0311] MIC is used to determine the approximate concentration at which a test surfactant inhibits bacterial growth.

[0312] In this antimicrobial testing protocol, a reference substance is typically used as a positive control. For example, ADBAC Quarternary Amine with CAS number 139-08-2 would be a suitable test reference.

[0313] Test measurements were performed on repeated 96-well plates and reported as the rounded integer average of the determined MIC. The repeated data were averaged using the following formula to determine the mean (arithmetic mean) of the selected measurements: Arithmetic mean = Sum of numbers in the set of interest / Number of items. Measurement variability was then reported based on the determined mean in the form of MIC + / -.

[0314] aspect Aspect 1 is a cleaning formulation comprising: at least one surfactant of formula I, and at least one detergent and / or at least one soap. Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0315] Aspect 2 is the formulation according to aspect 1, wherein the at least one detergent or soap is selected from anionic detergents, cationic detergents, nonionic detergents and zwitterionic detergents.

[0316] Aspect 3 is a formulation according to any one of Aspect 1 or Aspect 2, wherein the soap has the following general formula: (RCO2 - )n M n+ Where R includes an alkyl group, M is a metal, and n+ is +1 or +2.

[0317] Aspect 4 is a formulation according to any one of aspects 1-3, which further comprises at least one washing aid.

[0318] Aspect 5 is the formulation according to aspect 4, wherein the at least one detergent is selected from at least one compound selected from: tripolyphosphate, hypochlorous acid salt, zeolite, calcite / carbonate, citrate or polymer, sodium, pyrophosphate, orthophosphate, sodium aluminosilicate, inorganic salt of alkaline reagent, inorganic salt of alkali metal, sulfate, silicate and metasilicate.

[0319] Aspect 6 is a formulation according to any one of aspects 1-5, further comprising: at least one bleaching agent.

[0320] Aspect 7 is the formulation according to aspect 6, wherein the at least one bleaching agent is selected from at least one compound selected from: metal borate, peracid, peroxyacid, percarbonate, superphosphate, persilicate, persulfate, sodium hypochlorite, chlorine dioxide, hydrogen peroxide, sodium percarbonate, sodium perborate, peracetic acid, benzoyl peroxide, potassium persulfate, potassium permanganate, and sodium dithionite.

[0321] Aspect 8 is a preparation according to any one of aspects 1-7, further comprising: at least one enzyme.

[0322] Aspect 9 is the preparation according to aspect 8, wherein the at least one enzyme is selected from protease, amylase, cellulase, oxidase, mannanase, peroxidase and lipase.

[0323] Aspect 10 is a formulation according to any one of aspects 1-9, which further comprises at least one polymer.

[0324] Aspect 11 is a formulation according to aspect 10, wherein the at least one polymer is at least one compound selected from polymers including: methacrylamide; olefinically unsaturated monomers; N,N-dialkylaminoalkyl methacrylate; N,N-dialkylaminoalkyl methacrylate; N,N-dialkylaminoalkyl acrylamide; N,N-dialkylaminoalkyl methacrylamide; methacrylamidoalkyl trialkylammonium salt; acrylamide alkyl trialkylammonium salt; ethyleneamine; vinylimidazole; quaternized vinylimidazole and diallyl dialkylammonium salt; diallyl dimethylammonium salt; N,N-dimethylaminoethyl acrylate; N,N-dimethylaminoethyl methacrylate, [2-(methacryloylamino)ethyl]trimethylammonium salt; N,N-dimethylaminopropyl acrylamide; N,N-dimethylaminopropyl methacrylamide, acrylamide propyl trimethylammonium salt, methacrylamidopropyl trimethylammonium salt, and quaternized vinylimidazole.

[0325] Aspect 12 is a formulation for dry cleaning, comprising: at least one surfactant of formula I, and at least one solvent: Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0326] Aspect 13 is the formulation according to aspect 12, wherein the at least one solvent is at least one compound selected from: perchloroethylene, hydrocarbons, trichloroethylene, decamethylcyclopentasiloxane, dibutoxymethane, and n-propyl bromide.

[0327] Aspect 14 is a formulation according to any one of aspect 12 or aspect 13, which further comprises at least one cosolvent.

[0328] Aspect 15 is a formulation according to aspect 14, wherein the at least one cosolvent is a compound selected from at least one of the following: alcohols, ethers, glycol ethers, alkanes, alkenes, straight-chain and cyclic amides, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, methanol, ethanol, isopropanol, tert-butanol, trifluoroethanol, pentafluoropropanol, hexafluoro-2-propanol, methyl tert-butyl ether, methyl tert-amyl ether, propylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether. Ethers, propylene glycol methyl ether, ethylene glycol monobutyl ether, trans-1,2-dichloroethylene, decahydronaphthalene, methyl decanoate, tert-butyl acetate, ethyl acetate, glycol methyl ether acetate, ethyl lactate, diethyl phthalate, 2-butanone, N-alkylpyrrolidone (e.g., N-methylpyrrolidone, N-ethylpyrrolidone), methyl isobutyl ketone, naphthalene, toluene, trifluorotoluene, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorotributylamine, and perfluoro-2-butyloxacyclopentane.

[0329] Aspect 16 is the use of a compound of formula I as a surfactant in a cleaning formulation, wherein the cleaning formulation comprises at least one surfactant of formula I, at least one detergent, and / or at least one soap: Where R 1 and R 2 They may be the same or different and contain at least one group selected from C1-C6 alkyl groups. Optionally, the C1-C6 alkyl groups may include one or more oxygen, nitrogen, or sulfur atoms or groups including at least one of these atoms. The alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0330] Aspect 17 is the use of aspect 16, wherein the at least one detergent or soap is selected from anionic detergents, cationic detergents, nonionic detergents and zwitterionic detergents.

[0331] Aspect 18 is the use of either aspect 16 or aspect 17, wherein the soap has the following general formula: (RCO2 - )n M n+ Where R includes an alkyl group, M is a metal, and n+ is +1 or +2.

[0332] Aspect 19 is the use according to any one of aspects 16-18, further comprising: at least one detergent builder.

[0333] Aspect 20 is the use according to aspect 19, wherein the at least one detergent is selected from at least one compound selected from: tripolyphosphate, hypochlorous acid salt, zeolite, calcite / carbonate, citrate or polymer, sodium, pyrophosphate, orthophosphate, sodium aluminosilicate, inorganic salt of alkaline reagent, inorganic salt of alkali metal, sulfate, silicate and metasilicate.

[0334] Aspect 21 is the use according to any one of aspects 16-20, further comprising: at least one bleaching agent.

[0335] Aspect 22 is the use according to aspect 21, wherein the at least one bleaching agent is selected from at least one compound of the following: metal borate, peracid, peroxyacid, percarbonate, superphosphate, persilicate, persulfate, sodium hypochlorite, chlorine dioxide, hydrogen peroxide, sodium percarbonate, sodium perborate, peracetic acid, benzoyl peroxide, potassium persulfate, potassium permanganate, and sodium dithionite.

[0336] Aspect 23 is the use according to any one of aspects 16-22, further comprising: at least one enzyme.

[0337] Aspect 24 is the use according to aspect 23, wherein the at least one enzyme is selected from proteases, amylases, cellulases, oxidases, mannanases, peroxidases, and lipases.

[0338] Aspect 25 is the use according to any one of aspects 16-24, which further includes at least one polymer.

[0339] Aspect 26 is the use according to aspect 25, wherein the at least one polymer is at least one compound selected from polymers including: methacrylamide; olefinically unsaturated monomers; N,N-dialkylaminoalkyl methacrylate; N,N-dialkylaminoalkyl acrylate; N,N-dialkylaminoalkyl acrylamide; N,N-dialkylaminoalkyl methacrylamide; methacrylamidoalkyl trialkylammonium salt; acrylamide alkyl trialkylammonium salt; ethyleneamine; vinylimidazole; quaternized vinylimidazole and diallyl dialkylammonium salt; diallyl dimethylammonium salt; N,N-dimethylaminoethyl acrylate; N,N-dimethylaminoethyl methacrylate, [2-(methacryloylamino)ethyl]trimethylammonium salt; N,N-dimethylaminopropyl acrylamide; N,N-dimethylaminopropyl methacrylamide, acrylamide propyl trimethylammonium salt, methacrylamidopropyl trimethylammonium salt, and quaternized vinylimidazole.

[0340] Aspect 27 is the use of a compound of formula I as a surfactant in a dry cleaning formulation, wherein the formulation comprises at least one surfactant of formula I and at least one solvent: Where R 1 and R 2The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0341] Aspect 28 is the use according to aspect 27, wherein the at least one solvent is selected from at least one compound selected from: perchloroethylene, hydrocarbons, trichloroethylene, decamethylcyclopentasiloxane, dibutoxymethane, and n-propyl bromide.

[0342] Aspect 29 is the use described in any one of Aspect 27 or Aspect 28, and further comprises at least one cosolvent.

[0343] Aspect 30 is the formulation according to aspect 29, wherein the at least one cosolvent is a compound selected from at least one of the following: alcohols, ethers, glycol ethers, alkanes, alkenes, straight-chain and cyclic amides, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, methanol, ethanol, isopropanol, tert-butanol, trifluoroethanol, pentafluoropropanol, hexafluoro-2-propanol, methyl tert-butyl ether, methyl tert-amyl ether, propylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether. Ethers, propylene glycol methyl ether, ethylene glycol monobutyl ether, trans-1,2-dichloroethylene, decahydronaphthalene, methyl decanoate, tert-butyl acetate, ethyl acetate, glycol methyl ether acetate, ethyl lactate, diethyl phthalate, 2-butanone, N-alkylpyrrolidone (e.g., N-methylpyrrolidone, N-ethylpyrrolidone), methyl isobutyl ketone, naphthalene, toluene, trifluorotoluene, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorotributylamine, and perfluoro-2-butyloxacyclopentane.

[0344] Aspect 31 is a cleaning agent according to any one of aspects 1 to 16.

[0345] Aspect 36 is the use of formulations of surfactants comprising at least one compound of formula (I) for cleaning or dry cleaning purposes. Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0346] Aspect 37 is the use of a formulation in a CIP or COP cleaning method or process, said formulation comprising at least one surfactant of formula (I) and water. Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 Linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

[0347] Aspect 38 is the use according to aspect 37, wherein the formulation further includes an oxidizing agent, a stabilizer, a fragrance, or an acidifier.

[0348] Aspect 39 is a method for preparing an formulation according to any one of aspects 1 to 11, comprising: Synthesize compounds of formula I. Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally the C1-C6 alkyl groups may include one or more oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 The method comprises: an alkylbenzoic acid and a C1-C6 linker attached to a second molecule of formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine; the method comprising: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to provide a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and a second alkylation step to alkylate the N-terminus to provide a quaternary amine of formula I. Add at least one detergent and / or at least one soap; and optionally, water.

[0349] Aspect 40 is a method for preparing an formulation according to any one of aspects 12 to 15, comprising: Synthetic compounds of formula I Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally the C1-C6 alkyl groups may include one or more oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10An alkylbenzoic acid and a C1-C6 linker attached to a second molecule of Formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine. The method comprises: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to provide a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and a second alkylation step to alkylate the N-terminus to provide a quaternary amine of Formula I. Add solvent.

[0350] Aspect 41 is a method for preparing a formulation for use in CIP, COP, or hard surface cleaning processes, comprising: Synthetic compounds of formula I Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally the C1-C6 alkyl groups may include one or more oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 The method comprises: an alkylbenzoic acid and a C1-C6 linker attached to a second molecule of formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine; the method comprising: a ring-opening step to open a lactam ring to provide an amino acid having an N-terminus and a C-terminus; a first alkylation step to alkylate the N-terminus to provide a tertiary amine; a coupling step to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and a second alkylation step to alkylate the N-terminus to provide a quaternary amine of formula I. and Add at least one of an acidifier, oxidant, or stabilizer; and optionally add water.

[0351] Aspect 42 is the method according to any one of aspects 39 to 41, wherein the lactam is caprolactam.

[0352] Aspect 43 is the method according to any one of aspects 39 to 42, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

[0353] Aspect 44 is the method according to any one of aspects 39 to 43, wherein in the second alkylation step, the N-terminus is alkylated with an alkylating agent selected from benzyl bromide, ethyl bromoacetate, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonate, 3-iodopropanol, 3-bromopropanol, 2-iodoethanol, 2-bromoethanol, 6-bromohexanoic acid, and 1,3-dibromopropane.

Claims

1. A cleaning preparation comprising: At least one surfactant of formula I, and at least one detergent or at least one soap: Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 A linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

2. The formulation according to claim 1, wherein the at least one detergent or soap is selected from: anionic detergents, cationic detergents, nonionic detergents and zwitterionic detergents.

3. The formulation according to claims 1 and 2, wherein the soap has the following general formula: (RCO2 - ) n M n+ Where R includes an alkyl group, M is a metal, and n+ It is +1 or +2.

4. The formulation according to any one of claims 1-3, further comprising: at least one builder, wherein the at least one builder is selected from at least one compound selected from: tripolyphosphate, hypochlorous acid salt, zeolite, calcite / carbonate, citrate or polymer, sodium, pyrophosphate, orthophosphate, sodium aluminosilicate, inorganic salt of alkaline reagent, inorganic salt of alkali metal, sulfate, silicate and metasilicate; and / or Further includes: At least one bleaching agent, wherein the at least one bleaching agent is selected from at least one compound of the following: metal borates, peracids, peroxy acids, percarbonates, superphosphates, persilicates, persulfates, sodium hypochlorite, chlorine dioxide, hydrogen peroxide, sodium percarbonate, sodium perborate, peracetic acid, benzoyl peroxide, potassium persulfate, potassium permanganate, and sodium dithionite. and / or It further comprises at least one enzyme, wherein the at least one enzyme is selected from protease, amylase, cellulase, oxidase, mannanase, peroxidase and lipase; and / or The product further comprises at least one polymer, wherein the at least one polymer is at least one compound selected from the group consisting of: methacrylamide; olefinically unsaturated monomers; N,N-dialkylaminoalkyl methacrylates; N,N-dialkylaminoalkyl methacrylates; N,N-dialkylaminoalkyl acrylamide; N,N-dialkylaminoalkyl methacrylamide; methacrylamide-based alkyltrialkylammonium salt; acrylamide-based alkyltrialkylammonium salt; ethyleneamine; vinylimidazole; quaternized vinylimidazole and diallyl dialkylammonium salt; diallyl dimethylammonium salt; N,N-dimethylaminoethyl acrylate; N,N-dimethylaminoethyl methacrylate, [2-(methacryloamido)ethyl]trimethylammonium salt; N,N-dimethylaminopropyl acrylamide; N,N-dimethylaminopropyl methacrylamide, acrylamide-based propyltrimethylammonium salt, methacrylamide-based propyltrimethylammonium salt, and quaternized vinylimidazole.

5. An formulation for dry cleaning, comprising: At least one surfactant of formula I, and at least one solvent: Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 A linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

6. The formulation according to claim 5, wherein the at least one solvent is at least one compound selected from: perchloroethylene, hydrocarbons, trichloroethylene, decamethylcyclopentasiloxane, dibutoxymethane, and n-propyl bromide. Optionally further include At least one cosolvent, wherein the at least one cosolvent is at least one compound selected from the following: alcohols, ethers, glycol ethers, alkanes, alkenes, straight-chain and cyclic amides, perfluorinated tertiary amines, perfluorinated ethers, cycloalkanes, esters, ketones, aromatic compounds, methanol, ethanol, isopropanol, tert-butanol, trifluoroethanol, pentafluoropropanol, hexafluoro-2-propanol, methyl tert-butyl ether, methyl tert-amyl ether, propylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, propylene glycol Methyl ether, ethylene glycol monobutyl ether, trans-1,2-dichloroethylene, decahydronaphthalene, methyl decanoate, tert-butyl acetate, ethyl acetate, glycol methyl ether acetate, ethyl lactate, diethyl phthalate, 2-butanone, N-alkylpyrrolidone (e.g., N-methylpyrrolidone, N-ethylpyrrolidone), methyl isobutyl ketone, naphthalene, toluene, trifluorotoluene, perfluorohexane, perfluoroheptane, perfluorooctane, perfluorotributylamine, and perfluoro-2-butyloxacyclopentane.

7. A formulation for cleaning hard surfaces, comprising: At least one surfactant of formula I, optionally an antimicrobial agent and water: Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl, optionally the C1-C6 alkyl may include one or more of oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate. R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and C1-C attached to the second molecule of formula I 12 A linker, wherein the second molecule of Formula I is the same as or different from the first molecule of Formula I; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine.

8. The formulation according to claim 7, wherein the antimicrobial agent is present and has a concentration greater than 1 log within 30 seconds. 10 The reduction.

9. The formulation according to claim 7 or claim 8, wherein the antimicrobial agent is present at a concentration level of at least about 50 ppm.

10. The formulation according to any one of claims 7-9, further comprising additional additives selected from acidifiers, stabilizers, chelating agents, masking agents, buffers, detergents, wetting agents, defoamers, thickeners, foaming agents, curing agents, colorants, odorants or fragrances, optionally further comprising soaps, bleaching agents or detergents.

11. The preparation according to any one of claims 1-4 for use in cleaning.

12. Use of the formulation according to claim 5 or claim 6 for dry cleaning.

13. Use of the formulation according to any one of claims 7-9 for cleaning hard surfaces.

14. A method for preparing a formulation according to any one of claims 1 to 11, comprising: Synthetic compounds of formula I, Where R 1 and R 2 The same or different, and containing at least one group selected from C1-C6 alkyl groups, optionally the C1-C6 alkyl groups may include one or more oxygen, nitrogen or sulfur atoms or groups including at least one of these atoms, and the alkyl chain may optionally be substituted by one or more substituents selected from hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl and carboxylate groups; R 3 Selected from alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10 An alkylbenzoic acid and a C1-C6 linker attached to a second molecule of formula I, wherein the second molecule may be the same or different; n is an integer from 1 to 12; and X is selected from chlorine, bromine, and iodine, the method comprising: The ring-opening step is used to open the lactam ring to provide amino acids with N-terminus and C-terminus; The first alkylation step alkylates the N-terminus to provide a tertiary amine; A coupling step is performed to react the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative; and The second alkylation step alkylates the N-terminus to provide a quaternary amine of formula I; and Add another compound selected from at least one detergent or at least one soap, solvent or antimicrobial agent and water.

15. The method of claim 14, wherein the lactam is caprolactam.

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