Amino acid siloxane derivatives as surfactants in personal care and cosmetic products

Abstract

Personal care products such as shampoos, conditioners, hair dyes, hair removal products, cleansers, cosmetics, mascaras, and toothpastes may be formulated to contain one or more surfactants, or one or more surfactant classes, such as siloxane derivatives of amino acids having surface-active properties.

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Patent Application No. 18 / 795,174, filed on August 5, 2024, which in turn claims priority to U.S. Patent Provisional Application No. 63 / 531,194, filed on August 7, 2023, and the full disclosure thereof is incorporated by reference in its entirety.

[0002] This disclosure relates to surfactants used in personal care and cosmetic products. Such surfactants may include siloxane derivatives of amino acids having surface-active properties and methods for their synthesis. [Background technology]

[0003] Surfactants (molecules with surface-active properties) are widely used in commercial applications in a variety of formulations, from detergents to hair care products and cosmetics. Among other uses are soaps, detergents, lubricants, wetting agents, foaming agents, and spreading agents. In personal care cleansing products (e.g., shampoos, body washes, facial cleansers, liquid hand soaps), surfactants or surfactant mixtures can often serve as one of the most important ingredients, providing much of the composition's cleansing properties.

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

[0005] In many cases, these surfactants are amphiphilic molecules with a relatively water-insoluble hydrophobic "tail" group and a relatively water-soluble hydrophilic "head" group. These compounds can be adsorbed at interfaces such as between two liquids, between gas and liquid, or between solid and liquid. In systems containing relatively polar and relatively nonpolar components, the hydrophobic tail preferentially interacts with the relatively nonpolar component, while the hydrophilic head preferentially interacts with the relatively polar component. At the interface between water and oil, the hydrophilic head preferentially extends into the water, while the hydrophobic tail preferentially extends into the oil. When added to a gas-water interface, the hydrophilic head preferentially extends into the water, while the hydrophobic tail preferentially extends into the gas. In the presence of a surfactant, at least some of the intermolecular interactions between water molecules may be disrupted, and at least some of the interactions between water molecules may be replaced by generally weaker interactions between at least some of the water molecules and the surfactant. This can result in a decrease in surface tension, which may stabilize or otherwise alter the interface between materials of different physical forms.

[0006] At sufficiently high concentrations, surfactants can form aggregates that act to limit the exposure of their hydrophobic tails to polar solvents. One such aggregate is a micelle. In a typical micelle, the molecules are arranged spherically, with the hydrophobic tail of the surfactant preferentially located inside the sphere and the hydrophilic head preferentially located outside the micelle, which preferentially interacts with more polar solvents. The effect a given compound has on surface tension, as well as the concentration at which the compound forms micelles, can serve as definitions of the surfactant's properties. [Overview of the project]

[0007] This disclosure provides personal care products such as shampoos, conditioners, hair dyes, hair removal products, cleansers, cosmetics, mascaras, dental appliance cleansers, and toothpastes. These products may be formulated to contain one or more surfactants from one or more classes of surfactants disclosed herein.

[0008] This disclosure provides surfactants for personal care products in the form of siloxane derivatives of amino acids having surface-active properties. The amino acids may be natural or synthetic amino acids, or may be obtained via ring-opening reactions of molecules such as lactams, e.g., caprolactam. The amino acids may be functionalized with different types of siloxane groups to form compounds having surface-active properties. Characteristically, these compounds may have the ability to reduce the critical micelle concentration (CMC) and / or the surface tension of a liquid.

[0009] This disclosure relates to formula I or II

[0010] [ka]

[0011] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide one or more surfactant molecules having the structure of and optionally a soil penetrant, a foaming agent; a foaming power enhancer; a pH stabilizer; at least one paste; a fragrance and water to provide a hair shampoo formulation containing

[0012] For clarity, as disclosed herein and for any of the formulations provided herein, the molecule of Formula II has the following structure: Formula I - Linker - Formula I which may represent a composition of, and one molecule of Formula I may be the same as or different from another molecule of Formula I. In this exemplary composition, the linker is R in Formula I 3 , C1 - C 12 linker.

[0013] Furthermore, the surfactant molecules provided by the present disclosure are those compounds of Formula I or II in which R 1 and R 2 are methyl. Other surfactant molecules provided by the present disclosure are compounds of Formula I or II in which n and / or z is 5.

[0014] Specifically, R 3 may be selected from the group consisting of C2 - C 10 alkenyl, C2 - C 10 alkynyl, C2 - C 12 ester, C1 - C 10 hydroxyl, benzyl, C2 - C 12 alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3 - C8 carboxylic acid, C1 - C5 alkylbenzoic acid, and a 3 - carbon linker bonded to a second molecule of Formula I, and the second molecule of Formula I is the same as the first molecule of Formula I.

[0015] More specifically, R 3 may be selected from the group consisting of the following formulas.

[0016] [ka]

[0017] Furthermore, the use of compounds of formula I or II described herein as surfactants in hair shampoo formulations described herein is disclosed. This disclosure further relates to formula I or II

[0018] [ka]

[0019] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently selected from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactant molecules having the following structure; Optionally, fatty components; at least one thickening agent; at least one emulsifier; foaming agent; at least one clay; at least one binder; fragrance; and water The present invention provides a hair conditioner formulation that includes [the specified ingredient].

[0020] Furthermore, the use of compounds of formula I or II described herein as surfactants in hair conditioner formulations described herein is disclosed. This disclosure further relates to formula I or II

[0021] [ka]

[0022] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactant molecules having the following structure; Optionally, at least one wetting agent; at least one modifying agent; at least one solvent; at least one water-soluble polymer; at least one water-soluble solvent; at least one fatty component; hydrophobic modifier; and water The present invention provides a cleanser formulation that includes the following:

[0023] Furthermore, the use of compounds of formula I or II described herein as surfactants in the cleanser formulations described herein is disclosed. This disclosure also relates to Formula I or II

[0024] [ka]

[0025] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactant molecules having the following structure; Optionally, at least one fatty component; at least one rheological modifier; at least one emulsifier; at least one polymer; pigment; and water The present invention provides a mascara formulation that includes [the specified ingredient].

[0026] Furthermore, the use of compounds of formula I or II described herein as surfactants in mascara formulations described herein is disclosed. This disclosure further relates to formula I or II

[0027] [ka]

[0028] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12 12The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactant molecules having the following structure; At least one basic amino acid (optionally selected); calcium carbonate; fluoride ion source; flavoring agent; and water The present invention provides a toothpaste formulation that includes [the specified ingredient].

[0029] Furthermore, the use of compounds of formula I or II described herein as surfactants in toothpaste formulations described herein is disclosed. The above-mentioned and other features of this disclosure, as well as the methods for achieving them, will become more apparent and better understood by referring to the following description of embodiments in conjunction with the accompanying drawings. [Brief explanation of the drawing]

[0030] [Figure 1] Figure 1 shows a plot of surface tension versus concentration of surfactant 1, as described in Example 2b. [Figure 2] Figure 2 shows a plot of surface tension versus concentration of surfactant 2 as described in Example 3b. [Figure 3] Figure 3 shows a plot of surface tension versus concentration of surfactant 3, as described in Example 4b. [Figure 4] Figure 4 shows a plot of surface tension versus concentration of surfactant 4 as described in Example 5b. [Figure 5] Figure 5 shows a plot of surface tension versus concentration of surfactant 5 as described in Example 6b. [Figure 6] Figure 6 shows a plot of surface tension versus concentration of surfactant 6 as described in Example 7b. [Figure 7] Figure 7 shows a plot of surface tension versus concentration of surfactant 7 as described in Example 8b. [Figure 8] Figure 8 shows a plot of surface tension versus concentration of surfactant 8 as described in Example 9b. [Figure 9] Figure 9 shows a plot of surface tension versus concentration of surfactant 9 as described in Example 11b. [Figure 10] Figure 10 shows a plot of surface tension versus concentration of surfactant 10 as described in Example 10b. [Figure 11] Figure 11 shows a plot of surface tension versus concentration of the surfactant described in Comparative Example A2. [Modes for carrying out the invention]

[0031] As used herein, the phrase "within any range using these endpoints" means literally that any range may be selected from any two of the values ​​listed before the phrase, regardless of whether the values ​​are at the lower or higher end of the enumeration. For example, a pair of values ​​may be selected from the two lower values, the two higher values, or the lower value and the higher value.

[0032] As used herein, the term "alkyl" means any saturated carbon chain, which may be linear or branched, and which may be substituted at any point along the carbon chain. The carbon chain may have 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbons.

[0033] As used herein, the term “surface-active” means that the compound in question can reduce the surface tension and / or interfacial tension with a medium in which it is at least partially dissolved, thereby allowing it to adsorb to a gas-liquid interface and / or other interfaces. The term “surfactant” may be applied to such compounds.

[0034] With regard to the terminology of inaccuracy, the terms “about” and “approximately” may be used interchangeably and mean a measurement that includes the stated measurement and any measurement that is reasonably close to the stated measurement. A measurement that is reasonably close to the stated measurement deviates from the stated measurement by a reasonably small amount that is understood and readily verifiable by a person skilled in the art. Such deviations may result, for example, from measurement errors or small adjustments made to optimize performance. Where a person skilled in the art would determine that the value relating to such a reasonably small difference is not readily verifiable, the terms “about” and “approximately” may be understood to mean plus or minus 15% of the stated value, for example plus or minus 15%, plus or minus 12%, plus or minus 10%, plus or minus 9%, plus or minus 8%, plus or minus 8%, plus or minus 7%, plus or minus 6%, plus or minus 5%, plus or minus 4%, plus or minus 3%, plus or minus 2%, and further plus or minus 1%, etc.

[0035] This disclosure provides formulations for personal care products such as shampoos, conditioners, hair dyes, hair removal products, cleansers, cosmetics, mascaras, and toothpaste. I. Shampoo ingredients The shampoo composition may contain a combination of surfactants and conditioning agents. Such a product may contain one or more surfactants in combination with conditioning agents such as silicones, hydrocarbon oils, fatty esters, or combinations thereof. In a shampoo combination containing conditioning agents, the deposition of the conditioning agents may be improved by including certain cationic deposition polymers. These cationic deposition polymers may be cellulose polymers modified with cationic substituents or natural polymers such as guar polymers. The shampoo composition may be used as a shampoo for hair.

[0036] For example, a shampoo formulation may comprise a) a cosmetically acceptable medium; b) at least one of the surfactants of the Disclosure in about 1% to about 60% by weight; and c) about 0.01% to about 10% by weight of a water-soluble cationic modified starch polymer, the water-soluble cationic modified starch polymer having a molecular weight of about 1,000 to about 200,000 and a charge density of about 0.7 meq / g to about 7 meq / g.

[0037] In addition, the shampoo formulation may further contain one or more oily conditioning agents in an amount of approximately 0.01% to approximately 10% by weight. This disclosure also relates to a method for treating hair or skin, comprising the steps of applying the shampoo formulation described above to the hair or skin, and rinsing the hair or skin.

[0038] By combining a cationically modified starch polymer with one or more surfactants of this disclosure in a personal care composition, the deposition of conditioning agents on hair and / or skin is enhanced without reducing cleansing performance.

[0039] 1. Cosmetically acceptable media The shampoo formulations of this disclosure contain a cosmetically acceptable medium. The level and type of medium are selected depending on their compatibility with other ingredients and other desired properties of the product. Generally, the cosmetically acceptable medium is present in small amounts of the composition, such as about 15% by weight, about 20% by weight, about 25% by weight, about 30% by weight, about 35% by weight, about 40% by weight, about 45% by weight, about 50% by weight, about 55% by weight, about 60% by weight, about 65% by weight, about 70% by weight, about 75% by weight, about 80% by weight, or about 85% by weight, about 90% by weight, about 95% by weight, or about 99% by weight, or within any range of 15% to 99% by weight, or 20% to 90% by weight, or 30% to 80% by weight, or 40% to 70% by weight, or 50% to 60% by weight, or within any range using any two of the aforementioned values. Cosmetically acceptable media may be selected such that the composition of the present invention may be in the form of, for example, a pourable liquid, gel, paste, dry powder, or dry film.

[0040] Cosmetically acceptable media useful for the shampoo formulations of this disclosure include water and aqueous solutions of lower alkyl alcohols. The lower alkyl alcohols useful herein may be monohydric alcohols having 1 to 6 carbon atoms and may be selected from ethanol and isopropanol.

[0041] 2. Surfactants The shampoo formulations for hair of the present invention comprise one or more surfactants, and such mixtures of one or more surfactants are also referred to as a “surfactant system.” Surfactant systems may be included to provide a particular level of cleansing performance to the composition. A surfactant system comprises at least one surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, or a nonionic surfactant, and optionally, at least one other surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof. In a surfactant system or alone, such surfactants should be physically and chemically compatible with the essential components of the shampoos described herein and should not unduely impair the stability, aesthetics, or performance of the product.

[0042] Suitable surfactants used in the shampoo formulations of this disclosure are those of formula I or II.

[0043] [ka]

[0044] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. It contains one or more surfactant molecules and / or coprinsing molecules.

[0045] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, wherein the second molecule of formula I is the same as the first molecule of formula I.

[0046] More specifically, R 3 The following set of formulas may be selected.

[0047] [ka]

[0048] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The concentration of surfactants in the shampoo formulation should be sufficient to obtain the desired cleansing and lathering performance, and is generally within the range of about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 20% by weight or more, or about 25% by weight or less, about 30% by weight or less, about 40% by weight or less, about 45% by weight or less, or about 50% by weight or less, or within the range of about 5% by weight to about 50% by weight, or about 10% by weight to about 40% by weight, or 15% by weight to 30% by weight, or 10% by weight to 20% by weight, or any two of the aforementioned values.

[0049] 3. Conditioning agent The shampoo formulations of this disclosure may include oily conditioning agents. Such conditioning agents include materials used to provide specific conditioning effects to hair and / or skin. In a hair treatment composition, a suitable conditioning agent is one or more effects relating to shine, softness, combability, antistatic properties, wet handling, damage, manageability, body, and stickiness. Oily conditioning agents useful in the shampoo formulations of this disclosure may include non-volatile liquids that are water-insoluble or water-dispersible, forming emulsified liquid particles. Suitable oily conditioning agents are conditioning agents generally characterized by silicones (e.g., silicone oils, cationic silicones, silicone gums, high refractive index silicones, and silicone resins), organic conditioning oils (e.g., hydrocarbon oils, polyolefins, and fatty esters), or combinations thereof, or otherwise conditioning agents that form liquid dispersion particles in the aqueous surfactant matrix as defined herein.

[0050] One or more oily conditioning agents may be present in concentrations ranging from approximately 0.01% by weight or more, approximately 1% by weight or more, approximately 5% by weight or more, or approximately 6% by weight or less, approximately 8% by weight or less, or approximately 10% by weight or less, or within any of the ranges of approximately 0.01% by weight to approximately 10% by weight, or 1% by weight to 8% by weight, or 5% by weight to 6% by weight, or within any range using any two of the aforementioned values.

[0051] The ratio of oily conditioning agent to cationic hydrolyzed starch polymer can be at least about 2:1. Other conditioning agents, such as quaternary ammonium compounds, may also be included in the shampoo formulation. Suitable quaternary ammonium compounds used as conditioning agents in the personal care composition of the present invention include, but are not limited to, hydrophilic quaternary ammonium compounds having long-chain substituents with a carbonyl moiety such as an amide moiety, a phosphate ester moiety, or a similar hydrophilic moiety.

[0052] Examples of useful hydrophilic quaternary ammonium compounds include, but are not limited to, compounds designated as ricinolamidopropyltrimonium chloride, ricinolamidopropyltrimonium ethyl sulfate, hydroxystearamidopropyltrimonium methyl sulfate, and hydroxystearamidopropyltrimonium chloride in the CTFA Cosmetic Dictionary, or combinations thereof.

[0053] Further examples of useful quaternary ammonium surfactants include, but are not limited to, quaternium-16, quaternium-27, quaternium-30, quaternium-52, quaternium-53, quaternium-56, quaternium-60, quaternium-61, quaternium-62, quaternium-63, quaternium-71, quaternium-33, quaternium-43, isostearamidopropyl ethyldimonium ethosulfate, 1-quaternium-22 and quaternium-26, or combinations thereof, as specified in the CTFA Dictionary.

[0054] 4. Cationic Modified Polymers The shampoo formulations of this disclosure include water-soluble cationic modified starch polymers. As used herein, the term “cationically modified starch” means starch to which a cationic group has been added before the starch is broken down to a small molecular weight, or starch to which a cationic group has been added after the starch has been modified to a desired molecular weight. The definition of the term “cationically modified starch” also includes amphoteric modified starch. The term “amphoteric modified starch” means starch hydrolysates to which cationic and anionic groups have been added.

[0055] The shampoo formulations of this disclosure contain cationically modified starch polymer in an amount of about 0.01% by weight or more, about 1% by weight or more, about 5% by weight or more, or about 6% by weight or less, about 8% by weight or less, or about 10% by weight or less of the composition, or within any range of 0.01% to 10% by weight, or 1% to 8% by weight, or 5% to 6% by weight, or within any range using any two of the aforementioned values.

[0056] The cationically modified starch polymers used in the shampoo formulations of this disclosure have a molecular weight of about 1,000 to about 200,000. In one example, the cationically modified starch polymer has a molecular weight of about 5,000 to about 100,000. As used herein, the term "molecular weight" means weight-average molecular weight. Weight-average molecular weight can be measured using gel permeation chromatography ("GPC") with an Alliance HPLC (Waters 2695 Separation Module) equipped with two series-connected hydrogel columns (Waters Ultrahydrogel Linear 6-13um, 7.8×300nm GPC columns, part number 011545) at a column temperature of 30°C and a flow rate of 0.9 ml / min. A Viscotek Model 300 TDA (triple detector array), a light scattering detector (single angle, 90°), a viscosity detector, and a refractive index detector are all used at a detector temperature of 30°C. The method was prepared using pullulan narrow-distribution standard P-800 (Mw=788,000) from American Polymer Standards Corporation, and yielded a dn / dc of 0.147 with an injection volume of 25–100 μl. Further details regarding the weight-average molecular weight measurement method by GPC are described in U.S. Patent Application Publication No. 2003 / 0154883(A1), entitled "Non-Thermoplastic Starch Fibers and Starch Composition for Making Same".

[0057] The shampoo formulations of this disclosure contain a cationically modified starch polymer having a charge density of about 0.7 meq / g or more and about 7 meq / g or less. Chemical modifications to obtain such a charge density include, but are not limited to, the addition of amino groups and / or ammonium groups to the starch molecule. These ammonium groups may include substituents such as hydroxypropyltrimonium chloride, trimethylhydroxypropylammonium chloride, dimethylstearylhydroxypropylammonium chloride, and dimethyldodecylhydroxypropylammonium chloride. The cationic groups may be added to the starch before it is broken down into small molecular weights, or they may be added after such modifications.

[0058] The cationically modified starch polymer used in the shampoo formulations of this disclosure may also contain maltodextrin. Therefore, in one example, the cationically modified starch polymer may further be characterized by a dextrose equivalent ("DE") value of less than about 35, or between about 1 and about 20. The DE value is an index of the reducing equivalent of hydrolyzed starch relative to dextrose, and is expressed as a percentage (on a dry basis). Starch completely hydrolyzed to dextrose has a DE value of 100, while unhydrolyzed starch has a DE value of 0. Suitable assays for determining the DE value include those described in “Dextrose Equivalent”, Standard Analytical Methods of the Member Companies of the Corn Industries Research Foundation, 1st ed., Method E-26. In addition, the cationically modified starch polymer of the present invention may also contain dextrin. Dextrin is typically a thermal decomposition product of starch with a wide range of molecular weights.

[0059] The starch raw materials before chemical modification can be selected from a variety of sources, including tubers, legumes, cereals, and grains. Examples of such starch raw materials, though not limited to these, include corn starch, wheat starch, rice starch, glutinous corn starch, oat starch, cassava starch, glutinous barley, waxy rice starch, glutenous rice starch, sweet rice starch, amioca, potato starch, tapioca starch, oat starch, sago starch, sweet rice, or mixtures thereof.

[0060] In one example, the cationically modified starch polymer is selected from decomposed cationic corn starch, cationic tapioca, cationic potato starch, and mixtures thereof. In another example, the cationically modified starch polymer is cationic corn starch.

[0061] Starch may include one or more additional modifications before or after its breakdown to low molecular weight. For example, these modifications may include crosslinking, stabilization reactions, phosphorylation, and hydrolysis. Stabilization reactions may include alkylation and esterification.

[0062] The cationically modified starch polymer of the present invention may be incorporated into a composition in the form of hydrolyzed starch (e.g., acid, enzyme, or alkali decomposition), oxidized starch (e.g., peroxide, peracid, hypochlorite, alkali, or any other oxidizing agent), physically / mechanically decomposed starch (e.g., by the input of thermomechanical energy from a processing device), or a combination thereof.

[0063] 5. Other additives The shampoo formulation may also contain other additives such as soil penetration agents, foaming agents, foaming enhancers, thickeners, fragrances, pigments, and / or preservatives.

[0064] The individual concentrations of such additional components are within the range of about 0.001% by weight or more, about 0.01% by weight or more, about 1% by weight or more, about 5% by weight or more, or about 6% by weight or less, about 8% by weight or less, or about 10% by weight or less, or any range between 0.01% by weight and 10% by weight, or between 1% by weight and 8% by weight, or between 5% by weight and 6% by weight, or any range using any two of the aforementioned values.

[0065] The pH of the undiluted shampoo formulation may be approximately 3 to 9, or approximately 4 to 8. Buffers or other pH adjusters may be included to achieve the desired pH value.

[0066] The shampoo formulations of this disclosure may also contain anti-dandruff agents. Suitable, but not limited to, anti-dandruff agents include pyridinethione salts, azoles, selenium sulfide, particulate sulfur, keratolytic agents, and mixtures thereof. Such anti-dandruff agents must be physically and chemically compatible with the essential components of the shampoo formulation and must not unduely impair the stability, aesthetics, or performance of the product.

[0067] The shampoo formulations of this disclosure may also contain one or more opacifying agents. Opacifying agents are typically used in cleansing compositions to impart desired aesthetic effects to the shampoo formulation, such as color or pearlescent luster. In the shampoo formulations of this disclosure, the opacifying agent is present in an amount of about 20% by weight or less, about 10% by weight or less, and 2% by weight or less of the composition.

[0068] Suitable opacifying agents include, for example, fumed silica, polymethyl methacrylate, micronized TEFLON®, boron nitride, barium sulfate, acrylate polymers, aluminum silicate, aluminum starch octenyl succinate, calcium silicate, cellulose, chalk, corn starch, diatomaceous earth, fuller's earth, glyceryl starch, hydrated silica, magnesium carbonate, magnesium hydroxide, magnesium oxide, magnesium trisilicate, maltodextrin, microcrystalline cellulose, rice starch, silica, titanium dioxide, zinc laurate, zinc myristate, zinc neodecanoate, zinc rosinate, zinc stearate, polyethylene, alumina, attapulgite, calcium carbonate, calcium silicate, dextran, nylon, silylated silica, silk powder, soy flour, tin oxide, titanium hydroxide, trimagnesium phosphate, walnut shell powder, or mixtures thereof. The aforementioned powders may be surface-treated with lecithin, amino acids, mineral oil, silicone oil, or various other agents, either alone or in combination, which coats the surface of the powder and imparts hydrophobic properties to the particles.

[0069] The shampoo formulations of this disclosure may further contain a suspending agent in a concentration effective for suspending water-insoluble materials in a dispersed form within the composition, or for modifying the viscosity of the shampoo formulation. Such concentrations are generally in the range of about 0.01% by weight or more, about 1% by weight or more, about 5% by weight or more, or about 6% by weight or less, about 8% by weight or less, or about 10% by weight or less of the composition, or within any range of 0.01% to 10% by weight, or 1% to 8% by weight, or 5% to 6% by weight, or within any range using any two of the aforementioned values.

[0070] Useful suspending agents in this specification include anionic polymers and nonionic polymers. In this specification, vinyl polymers such as crosslinked acrylic acid polymers having the CTFA name of carbomers are useful.

[0071] The shampoo formulations of this disclosure may contain one or more paraffinic hydrocarbons. Examples of paraffinic hydrocarbons suitable for use in the compositions of the present invention include substances known for use in hair care or other personal care compositions, with a vapor pressure of approximately 21°C (approximately 70°F) or higher at 1 atm. Examples, though not limited to these, include pentane and isopentane.

[0072] The shampoo formulations of this disclosure may also contain one or more propellants. Suitable propellants for use in the compositions of the present invention include substances known for use in hair care or other personal care compositions, such as liquefied gas propellants and compressed gas propellants. Suitable propellants have a vapor pressure of less than about 21°C (about 70°F) at 1 atm. Not limited examples of suitable propellants are alkanes, isoalkanes, haloalkanes, dimethyl ethers, nitrogen, nitrous oxide, carbon dioxide, and mixtures thereof.

[0073] The shampoo formulations of this disclosure may also contain water-soluble and water-insoluble vitamins, such as vitamins B1, B2, B6, B12, C, pantothenic acid, pantothenyl ethyl ether, panthenol, biotin, and derivatives thereof, as well as vitamins A, D, E, and derivatives thereof. The compositions of the present invention may also contain water-soluble and water-insoluble amino acids, such as asparagine, alanine, indole, glutamic acid, and salts thereof, as well as tyrosine, tryptamine, lysine, histidine, and salts thereof.

[0074] The shampoo formulations of this disclosure may contain foaming agents or foaming enhancers such as ammonium lauryl sulfate, sodium lauryl sulfate, ammonium lauryl ether sulfate, and cocamidopropyl betaine.

[0075] The shampoo formulations of this disclosure may include thickeners such as xanthan gum and acrylate copolymer. The shampoo formulations of this disclosure may contain monovalent or divalent salts such as sodium chloride.

[0076] The shampoo formulations of this disclosure may also contain chelating agents. The shampoo formulations of this disclosure may further contain substances useful for preventing hair loss and hair growth stimulants or hair growth agents.

[0077] 6. Manufacturing Method The shampoo formulations of this disclosure can generally be prepared by mixing the raw materials together at either room temperature or a high temperature, for example, about 72°C. Heat should only be used if solid raw materials are present in the composition. The raw materials are mixed at a batch processing temperature. Additional raw materials, including electrolytes, polymers, fragrances, and particles, may be added to the product at room temperature.

[0078] 7. Hair Treatment Methods The shampoo formulations of this disclosure are used in conventional methods for cleansing and conditioning hair. Generally, a method of treating hair involves applying the shampoo formulations of this disclosure to the hair. More specifically, an effective amount of the shampoo formulation is applied to hair that may be wet, and then the shampoo formulation is rinsed off. Such an effective amount is generally in the range of about 1 g to about 50 g, or about 1 g to about 20 g. Application to hair typically involves spreading the shampoo formulation throughout the hair so that most or all of the hair comes into contact with the shampoo formulation.

[0079] This method of treating hair comprises (a) applying an effective amount of shampoo formulation to the hair, and (b) rinsing the applied area of ​​hair with water. These steps may be repeated a desired number of times to achieve the desired cleansing and conditioning effect.

[0080] In some forms of the shampoo formulations of this disclosure, the shampoo formulations may be packaged in pump dispenser bottles or aerosol containers. In other useful forms, the shampoo formulations may be dried to form a film or powder, or applied to a substrate to be used for application to hair.

[0081] II. Conditioner formulations This disclosure provides hair conditioner formulations. The conditioner formulations of this disclosure can provide long-lasting styling and conditioning effects, can suppress frizz and impart defined curls, and can improve hair health and manageability. After the hair has optionally been cleansed, for example with shampoo, the conditioner may be applied to the hair to impart multiple effects to the hair. For example, the hair may first be treated with a rinse-off conditioner (after optionally being cleansed) to impart conditioning and detangler properties to the hair.

[0082] An example of a rinse-off conditioner, though not limited to this, may include at least 4% by weight of natural fatty components, comprising one or more solid, semi-solid, or liquid natural fatty compounds; at least 1% by weight of one or more surfactants selected from one or more surfactant classes; one or more nonionic thickeners; one or more emulsifiers; one or more mineral clays; and water.

[0083] 1. Fatty compounds Rinse-off conditioners may contain both natural solid or semi-solid fatty compounds (e.g., waxes or butters) and natural liquid oils. For example, a combination of shea butter and sunflower seed oil may be particularly useful. Alternatively, a suitable viscosity for the rinse-off conditioner may be achieved using natural fatty components, surfactants, and nonionic thickeners. For example, nonionic polysaccharide thickeners (e.g., sclerotium gum) may be particularly useful.

[0084] Rinse-off conditioning masks contain a large amount (typically at least 4 or 5% by weight) of natural fatty components. These natural fatty components may include both natural solid or semi-solid fatty compounds (e.g., waxes or butters) and natural liquid oils. For the purposes of this disclosure, solid or semi-solid fatty compounds are fatty substances with a melting point of 31°C or higher. Oils, on the other hand, are fatty substances with a melting point of less than 31°C. Therefore, oils are liquid at room temperature. The mention of a total amount of natural fatty components does not necessarily indicate that the rinse-off conditioner contains no non-natural fatty components. In other words, in some cases, the rinse-off conditioner may contain one or more non-natural fatty compounds in addition to the natural fatty compounds. Nevertheless, it may be desirable to omit non-natural fatty compounds to obtain a natural product.

[0085] As used in this disclosure, the term “natural” means a natural raw material component, such as a raw material component derived from a plant or vegetable, for example, a natural fatty component or a solid or semi-solid natural fatty compound or natural oil as used in this disclosure. As used in this disclosure, the term “non-natural” means a raw material component that is not natural and may contain alkanes or hydrocarbons or synthetic oils, such as mineral oil or silicone oil.

[0086] The total amount of natural fatty components may be approximately 4% by weight or more, approximately 5% by weight or more, approximately 10% by weight or more, or approximately 15% by weight or less, approximately 20% by weight or less, or approximately 25% by weight or less, or any combination of these endpoints, based on the total weight of the rinse-off conditioner.

[0087] Examples of solid or semi-solid fatty compounds, not limited to those derived from plant, animal, and mineral sources, include, for example, shea butter, white bayberry wax, beeswax, illipe butter, paraffin wax, hard tallow, lanolin, cocoum butter, sala butter, gay wax, murumuru seed butter, beeswax, ceresin wax, cocoa butter, jojoba wax, candelilla wax, palm butter, carnauba wax, esparto wax, shellac wax, sugarcane wax, lignite wax, aurichalle wax, rice bran wax, castor wax, montan wax, sugarcane wax, rice bran wax, sunflower wax, and mixtures thereof. In some cases, shea butter may be particularly useful.

[0088] Examples of natural oils, though not limited to them, include oils derived from plant, animal, and mineral sources, such as coconut oil, wheat germ oil, sunflower seed oil, avocado oil, babassu oil, macadamia oil, almond oil, apricot kernel oil, carrot oil, castor oil, citrus seed oil, corn oil, cottonseed oil, jojoba oil, linseed oil, mineral oil, mink oil, olive oil, palm kernel oil, peach kernel oil, peanut oil, rapeseed oil, safflower oil, sesame oil, soybean oil, vegetable oils, wheat germ oil, and mixtures thereof. In some cases, sunflower oil may be particularly useful.

[0089] 2. Surfactants The conditioner formulation of the present invention contains one or more surfactants, also referred to as a surfactant system. The surfactant system is included to smooth the cuticle and create softness by depositing on the hair. The surfactant system includes at least one surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, or a nonionic surfactant, and optionally at least one other surfactant, which may be an amphoteric surfactant, a zwitterionic surfactant, a cationic surfactant, a nonionic surfactant, or a combination thereof.

[0090] Suitable surfactants used in the conditioner formulations of this disclosure are those of formula I or II.

[0091] [ka]

[0092] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactant molecules and / or copolymer molecules, and optionally soil penetration agents; foaming agents; foaming power enhancers; pH stabilizers; at least one thickener; fragrance, or water. Includes.

[0093] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, wherein the second molecule of formula I is the same as the first molecule of formula I.

[0094] More specifically, R 3 The following set of formulas may be selected.

[0095] [ka]

[0096] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The total amount of one or more surfactants in a rinse-off conditioner may vary, but is usually at least 1% by weight based on the total weight of the rinse-off conditioning mask. In some cases, the total amount of one or more surfactants may be within the range of approximately 1% by weight or more, approximately 2% by weight or more, approximately 4% by weight or more, approximately 6% by weight or more, or approximately 8% by weight or less, approximately 10% by weight or less, approximately 12% by weight or less, or approximately 15% by weight or less, or within the range of 1% to 15% by weight, or 2% to 12% by weight, or 4% to 10% by weight, or 1% to 8% by weight, or 2% to 8% by weight, or 5% to 8% by weight, or within any range using any two of the aforementioned values.

[0097] 3. Thickening agent Rinse-off conditioners may contain one or more nonionic thickeners. All thickeners referred to throughout this disclosure may also be referred to as “rheological modifiers,” “thickening compounds,” “gelling agents,” etc. Nonionic thickeners include nonionic guar gum, sclerotium gum, biopolysaccharide gums of microbial origin, gums derived from plant extracts, cellulose, particularly hydroxypropylcellulose or hydroxyethylcellulose, pectin, and mixtures thereof.

[0098] A suitable nonionic thickener may include cellulose modified with a group containing at least one fatty acid chain. Examples of such modified cellulose may include hydroxyethylcellulose modified with a group containing at least one fatty acid chain, such as an alkyl, arylalkyl, or alkylaryl group or a mixture thereof, where the alkyl group is C8-C22, for example, NATROSOL® PLUS GRADE 330 CS(C) sold by Aqualon. 16 These include alkyl(15) nonylphenyl ether (H15) hydroxyethylcellulose modified with alkylphenyl polyalkylene glycol ether groups, such as AMERCELL POLYMER HM-1500 (polyethylene glycol (15) nonylphenyl ether), sold by Amerchol.

[0099] Further suitable nonionic thickeners may include hydroxypropyl guar modified with a group comprising at least one fatty acid chain, for example, ESAFLOR HM 22 (C22 alkyl chain) sold by Lamberti, and RE210-18 (C14 alkyl chain) and RE205-1 (C20 alkyl chain) sold by Rhone-Poulenc.

[0100] Further suitable nonionic thickeners may include copolymers of vinylpyrrolidone and alipid chain hydrophobic monomers; copolymers of C1-C6 alkyl methacrylate or acrylate and amphiphilic monomers containing at least one alipid chain; polyurethane polyethers containing both a hydrophilic block, usually polyoxyethylene-like, and a hydrophobic block, which may be an aliphatic sequence alone and / or an alicyclic and / or aromatic sequence; or polymers having an aminoplast ether backbone containing at least one alipid chain.

[0101] In some cases, the nonionic thickener may be selected from the group consisting of polysaccharides and associative polymers. In some cases, preferred nonionic thickeners are sclerotium gum, guar gum, optionally hydrophobic hydroxyalkylcellulose, such as optionally hydrophobic hydroxyethylcellulose, optionally hydrophobic hydroxymethylcellulose, and optionally hydrophobic inulin. In some cases, sclerotium gums are particularly useful.

[0102] The total amount of one or more nonionic thickeners may vary, but is typically within the range of approximately 0.1% by weight or more, approximately 0.5% by weight or more, approximately 1% by weight or more, approximately 2% by weight or more, or approximately 4% by weight or less, approximately 6% by weight or less, approximately 8% by weight or less, or within the range of 0.1% to 8% by weight, or 0.5% to 6% by weight, or 1% to 4% by weight, or within any two of the aforementioned values.

[0103] 4. Emulsifier Rinse-off conditioners may be in the form of emulsions, such as water-in-oil emulsions. Accordingly, they may contain one or more emulsifiers. Useful emulsifiers include, for example, fatty acids, fatty alcohols, esters of polyols and fatty acids, polyol fatty esters and fatty ethers having branched or unsaturated chains containing 10 to 30 carbon atoms, esters of sorbitan and fatty acids, esters of sugars and fatty acids, and mixtures thereof. The fatty chains in the emulsifiers may, for example, have a length of about 8 to about 35 carbon atoms, may be saturated or unsaturated, and may optionally be branched. In some cases, the fatty chains have a length of about 10 to 30 carbon atoms, or about 12 to about 24 carbon atoms.

[0104] Examples of emulsifiers that are not limited to these include sorbitan laurate, sorbitan palmitate, sorbitan sesquiisostearate, sorbitan sesquioleate, sorbitan sesquistearate, sorbitan stearate, sorbitan oleate, sorbitan monoisostearate, sorbitan triisostearate, sorbitan trioleate, sorbitan tristearate; glyceryl behenate, glyceryl caprate, glyceryl caprylate, etc. Glyceryl caprate, glyceryl coconut oil fatty acid, glyceryl erucate, glyceryl hydroxystearate, glyceryl isostearate, glyceryl lanolinate, glyceryl laurate, glyceryl linoleate, glyceryl myristate, glyceryl oleate, glyceryl lactate palmitate, glyceryl sesquioleate, glyceryl stearate, glyceryl citrate stearate, glyceryl lactate stearate; This product contains polyglyceryl-4 sostearate, polyglyceryl-3 oleate, polyglyceryl-2 sesquioleate, triglyceryl diisostearate, diglyceryl monooleate, tetraglyceryl monooleate, glycol distearate, glycol hydroxystearate, glycol oleate, glycol ricinoleate, glycol stearate, propylene glycol isostearate, propylene glycol hydroxystearate, propylene glycol laurate, propylene glycol myristate, propylene glycol oleate, propylene glycol ricinoleate, propylene glycol stearate, sucrose coconut oil fatty acid, sucrose laurate, methyl glucose sesquistearate, methyl glucose dioleate, cetyl alcohol, stearyl alcohol, cetearyl alcohol, cetyl esters, and mixtures thereof.

[0105] The total amount of one or more emulsifiers may vary depending on the other ingredients in the rinse-off conditioner and their amounts. Nevertheless, the total amount of one or more emulsifiers is typically in the range of about 0.5% by weight or more, about 1% by weight or more, about 2% by weight or more, about 5% by weight or more, or about 10% by weight or less, about 12% by weight or less, about 14% by weight or less, about 16% by weight or less, or about 20% by weight or less, or within the range of 0.5% to 20% by weight, or 1% to 15% by weight or 2% to 10% by weight, or within the range of any two of the aforementioned values.

[0106] 5. Clay One or more mineral clays may be included in the rinse-off conditioner. Mineral clays may include kaolin (e.g., the minerals kaolinite, dickite, halloysite, and nacrite); smectite (e.g., dioctahedral smectites such as montmorillonite, nontronite, and bydelite, as well as trioctahedral smectites such as saponite); illite (e.g., clay mica); chlorite; and other types of clay such as sepiolite and attapulgite.

[0107] The total amount of mineral clay in the rinse-off conditioner may vary, but is typically within the range of about 0.01% by weight or more, about 1% by weight or more, about 5% by weight or more, or about 6% by weight or less, about 8% by weight or less, or about 10% by weight or less, based on the total weight of the rinse-off conditioner, or within the range of 0.01% to 10% by weight, or 1% to 8% by weight, or 5% to 6% by weight, or within any two of the aforementioned values.

[0108] 6. Water and water-soluble solvents The total amount of water in the rinse-off conditioner may vary, but is typically within the range of approximately 50% by weight or more, approximately 60% by weight or more, approximately 70% by weight or more, or approximately 80% by weight or less, approximately 90% by weight or less, or any of these endpoints, based on the total weight of the rinse-off conditioner.

[0109] A water-soluble solvent may optionally be included in the rinse-off conditioner. The term “water-soluble solvent” is interchangeable with the term “water-miscible solvent” and means a compound that is liquid at 25°C and atmospheric pressure (760 mmHg) and has at least 50% solubility in water under these conditions. In some cases, the water-soluble solvent has at least 60%, 70%, 80%, or 90% solubility. Examples of water-soluble solvents that are not limited include organic solvents such as C1-4 alcohols, polyols, glycols, and mixtures thereof. Examples of organic solvents that can be mentioned without limitation include monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers, such as monomethyl, monoethyl, and monobutyl ethers of ethylene glycol, propylene glycol or its ethers, such as monomethyl ethers of propylene glycol, butylene glycol, hexylene glycol, and dipropylene glycol, and even alkyl ethers of diethylene glycol, such as monoethyl or monobutyl ethers of diethylene glycol. Other suitable examples of organic solvents include ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propanediol, and glycerin. Organic solvents may be volatile or non-volatile compounds.

[0110] Further, less limited, examples of water-soluble solvents include polyols (polyhydric alcohols) containing alkanediols such as glycerin, 1,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4-pentanediol (caprylyl glycol), 1,2-hexanediol, 1,2-pentanediol, and 4-methyl-1,2-pentanediol; alkyl alcohols having 1 to 4 carbon atoms such as ethanol, methanol, butanol, propanol, and isopropanol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol mono-n-propyl Glycol ethers such as ethers, ethylene glycol mono-isopropyl ether, diethylene glycol mono-isopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether, diethylene glycol mono-t-butyl ether, 1-methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-t-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-isopropyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, and dipropylene glycol mono-isopropyl ether, 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, formamide, acetamide, dimethyl sulfoxide, sorbitol, sorbitan, acetin, diacetin, triacetin, sulfolane, and mixtures thereof.

[0111] Polyhydric alcohols may also be useful. Examples of polyhydric alcohols include glycerin, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 3-methyl-1,3-butanediol, 1,5-pentanediol, tetraethylene glycol, 1,6-hexanediol, 2-methyl-2,4-pentanediol, polyethylene glycol, 1,2,4-butanetriol, 1,2,6-hexanetriol, and mixtures thereof. Polyol compounds may also be used. Examples, though not limited to these, include aliphatic diols such as 2-ethyl-2-methyl-1,3-propanediol, 3,3-dimethyl-1,2-butanediol, 2,2-diethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 2,5-dimethyl-2,5-hexanediol, 5-hexen-1,2-diol, and 2-ethyl-1,3-hexanediol, as well as mixtures thereof.

[0112] The total amount of one or more water-soluble solvents may vary, but is typically, based on the total weight of the rinse-off conditioner, it may be within the range of approximately 0.1% by weight or more, approximately 1% by weight or more, approximately 5% by weight or more, approximately 10% by weight or more, or approximately 15% by weight or less, approximately 20% by weight or less, approximately 25% by weight or less, or within the range of 0.1% to 25% by weight, or 1% to 20% by weight, or 5% to 15% by weight, or within any two of the aforementioned values.

[0113] 7. Other additives The conditioner formulations of this disclosure may also contain other additives, such as emulsifiers, foaming agents, hydrotropic substances, fragrances, pigments, and stabilizers.

[0114] The conditioner formulations of this disclosure may contain emulsifiers. Suitable emulsifiers include sorbitan laurate, sorbitan palmitate, sorbitan sesquiisostearate, sorbitan sesquioleate, sorbitan sesquistearate, sorbitan stearate, sorbitan oleate, sorbitan monoisostearate, sorbitan triisostearate, sorbitan trioleate, sorbitan tristearate; glyceryl behenate, glyceryl caprate, glyceryl caprylate, caprylic / capric acid Glyceryl, Cocoate Glycerides, Glyceryl Erucate, Glyceryl Hydroxystearate, Glyceryl Isostearate, Glyceryl Lanolinate, Glyceryl Laurate, Glyceryl Linoleate, Glyceryl Myristate, Glyceryl Oleate, Glyceryl Lactate Palmitate, Glyceryl Sesquioleate, Glyceryl Stearate, Glyceryl Citrate Stearate, Glyceryl Lactate Stearate; Polyglyceryl-4 Isostearate The following may be included: polyglyceryl-3 oleate, polyglyceryl-2 sesquioleate, triglyceryl diisostearate, diglyceryl monooleate, tetraglyceryl monooleate, glycol distearate, glycol hydroxystearate, glycol oleate, glycol ricinoleate, glycol stearate, propylene glycol isostearate, propylene glycol hydroxystearate, propylene glycol laurate, propylene glycol myristate, propylene glycol oleate, propylene glycol ricinoleate, propylene glycol stearate, sucrose coconut oil fatty acid, sucrose laurate, methyl glucose sesquistearate, methyl glucose dioleate, cetyl alcohol, stearyl alcohol, cetearyl alcohol, cetyl esters, polyethylene glycol (PEG) and its derivatives, and mixtures thereof.

[0115] The conditioner formulations of this disclosure may contain foaming agents or foam enhancers such as ammonium lauryl sulfate, sodium lauryl sulfate, ammonium lauryl ether sulfate, and cocamidopropyl betaine.

[0116] The conditioner formulations of this disclosure may contain hydrotropic substances such as benzenesulfonates, naphthalenesulfonates, short-chain (C1-11) alkylbenzenesulfonates, medium-chain (C6-11) alkylsulfonates, medium-chain (C6-11) alkyl sulfates, alkyl polyglucosides, medium-chain (C6-10) alkyldimethylamine oxides, alkyldiphenyl oxide disulfonates, phosphate ester hydrotropic substances, and medium-chain (C6-11) alkyl ether (ethylene oxide up to 10 moles) sulfates. The cations of the hydrotropic compounds may include alkali metals, ammonium, and triethanolammonium cations.

[0117] 8. How to use A typical method for treating hair in accordance with this disclosure (also referred to as a “routine”) may include an optional first step of cleansing the hair with a cleansing composition, such as a shampoo, and a second step of treating the hair with a rinse-off conditioner, leaving the rinse-off conditioner on the hair for a sufficient amount of time, and then rinsing it off the hair.

[0118] III. Cleanser This disclosure further provides cleanser formulations. These formulations may be useful for cleansing the body, in particular the skin. In addition, the cleansing formulations of this disclosure may be useful for removing makeup from the skin. When cleansing and / or removing makeup from the skin, the cleanser formulations may be applied to the skin and rinsed off with water. These cleanser formulations are gentle on the skin and may replenish moisture to the skin during cleansing.

[0119] The cleanser of this disclosure may comprise at least one nonionic surfactant, at least one additional surfactant selected from one or more surfactant classes, an oil, a water-soluble alcohol, a water-soluble polyol, at least one water-soluble polymer, a water-soluble inorganic or organic salt, and water.

[0120] 1. Surfactants The cleanser of this disclosure may include a first surfactant selected from nonionic surfactants, and a second surfactant comprising one or more additional surfactants selected from one or more surfactant classes. It may be appropriate to use a mixture of surfactants to provide stability to the composition. This allows the cleanser to be rinsed off without leaving any residue.

[0121] The surfactants suitable for use in the cleanser formulations of this disclosure are those of formula I or II.

[0122] [ka]

[0123] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactants and / or copolymers, and optionally soil penetration agents; foaming agents; foaming power enhancers; pH stabilizers; at least one thickener; fragrance, or water. Includes.

[0124] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, wherein the second molecule of formula I is the same as the first molecule of formula I.

[0125] More specifically, R 3 The following set of formulas may be selected.

[0126] [ka]

[0127] In particular, a suitable surfactant or co-surfactant may include one or more of the surfactants 1 to 12 described herein. The content of the first surfactant is within the range of approximately 15% by weight or more, approximately 20% by weight or more, or approximately 25% by weight or less, approximately 30% by weight or less, or any of these endpoints. This allows the cleanser to be clearly rinsed off without any residue. Content within this range provides improved compatibility with makeup and the ability to lift dirt while rinsing off cleanly without any residue.

[0128] One or more surfactants selected from one or more surfactant classes may be used as a second surfactant. The content of this second surfactant is within the range of approximately 1% by weight or more, approximately 5% by weight or more, or approximately 10% by weight or less, approximately 15% by weight or less, or any of these endpoints.

[0129] 2. Oils The oil may contain hydrocarbon oils; the oil may contain one or more compounds selected from the group consisting of hydrocarbon oils, ester oils, and ether oils, and its viscosity at 30°C is 30 mPa·s or less. The viscosity of the oil can be measured using a BM-type viscometer (commercially available from TOKIMEC Co., Ltd., measurement conditions: rotor No. 1, 60 rpm, 1 minute). Such low-viscosity oils exhibit high penetration into minute areas and high solubility for dirt, resulting in enhanced cleansing power against oily cosmetic stains such as oily mascara. Furthermore, such oils exhibit an improved feel without a strong oily sensation. The oil is preferably liquid at 20°C because this provides the enhanced cleansing power for the reasons mentioned above.

[0130] Liquid oils commonly used in cosmetic compositions and satisfying the above-mentioned conditions may be used in such oils. For example, liquid paraffin, liquid isoparaffin, squalene, isododecane, etc., may be used as hydrocarbon oils in the oils.

[0131] The ester oil in the oil formulation may include cholesteryl isostearate, isopropyl palmitate, isopropyl myristate, isopropyl isostearate, octadecyl myristate, cetyl 2-ethylhexanoate, isononyl isononanoate, isotridecyl isononanoate, neopentyl glycol dicaprate, glyceryl tri(2-ethylhexanoate), glyceryl tri(caprylic / capric acid), etc. Considering the difficulty of crystal precipitation, ester oils having branched alkyl chains may be used.

[0132] The ether oil in the oil formulation may include ether oils such as alkyl-1,3-dimethylbutyl ether, dioctyl ether, and nonylphenyl ether. The oil content is within the range of approximately 10% by weight or more, approximately 15% by weight or more, approximately 20% by weight or more, or approximately 25% by weight or less, approximately 30% by weight or less, approximately 35% by weight or less, approximately 40% by weight or less, or any of these endpoints.

[0133] 2. Water-soluble polyols Water-soluble polyols are compounds having three or more hydroxyl groups in their molecule, and include glycerols such as glycerol and diglycerol; sugars such as sorbitol, maltitol, maltose, fructose, xylitol, maltotriose, threitol, erythritol, and glucose; and sugar derivatives such as methyl glucoside and ethyl glucoside. Among these, glycerol, sorbitol, and maltitol may be used to enhance moisture retention. Furthermore, glycerol and sorbitol are used from the viewpoint of rinsing power. Water-soluble polyols play a role in increasing the surface hydrophobicity of the entire skin cleansing formulation.

[0134] One or more water-soluble polyols may be used, and it may be appropriate to use a combination of two or more compounds. The water-soluble polyol is present in the cleanser formulation in an amount of 10% or more by weight, approximately 15% or more by weight, approximately 20% or more by weight, or approximately 25% or less by weight, approximately 30% or less by weight, approximately 35% or less by weight, approximately 40% or less by weight, or any of these endpoints.

[0135] 3. Water-soluble alcohol Water-soluble alcohols are compounds having one or two hydroxyl groups in their molecule. Water-soluble alcohols may include monohydric alcohols such as ethanol, propanol, isopropanol, butanol, and isobutanol; and glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, hexylene glycol, and isoprene glycol. Compounds having two hydroxyl groups in their molecule may be suitable, and considering temperature stability over a wide temperature range, 1,3-butylene glycol, isoprene glycol, propylene glycol, and dipropylene glycol can also be used.

[0136] A mixture of one or more water-soluble alcohols may be used. The water-soluble alcohol may be present in the cleanser formulation in amounts of 10% by weight or more, about 15% by weight or more, about 20% by weight or more, or about 25% by weight or less, about 30% by weight or less, or any of these endpoints.

[0137] The mass ratio of water-soluble polyols to water-soluble alcohols in the cleanser formulation is 0.1 to 2.5, or 1 to 2.5. 4. Water-soluble polymers The water-soluble polymer may consist of one or more components selected from water-soluble polymers containing (meth)acrylic acid as a structural unit (water-soluble polymers containing structural units derived from (meth)acrylic acid) and acryloyl methyl taurate-vinylpyrrolidone copolymer. The water-soluble polymer plays a role in increasing the viscosity of the skin cleansing agent composition of the present invention, thereby preventing the liquid from dripping when the cleanser is applied to the skin and allowing the cleanser to mix well with the dirt, making cleansing easier.

[0138] Water-soluble polymers containing (meth)acrylic acid structural units may be compounds synthesized by using (meth)acrylic acid as a monomer, such as acrylic acid-alkyl methacrylate copolymers, which are typically crosslinked copolymers of acrylic acid and alkyl (C10-C30) methacrylate, and more typically are commercially available products such as PEMULEN TR-1, PEMULEN TR-2, PEMULEN TR-1, PEMULEN TR-1, and Carbopol ETD 2020 (commercially available from Lubrizol Advanced Materials Inc.).

[0139] Water-soluble polymers containing (meth)acrylic acid as a structural unit may be used by neutralizing all or part of the (meth)acrylic acid units with an alkaline agent. The alkaline agent for neutralization is not particularly limited, insofar as it is an alkaline agent that can be normally blended into a cosmetic composition, and includes potassium hydroxide, sodium hydroxide, etc. One or more compounds may be used as the alkaline agent. The agent may be present in an amount of about 0.01% by weight or more, 0.1% by weight or more, 0.2% by weight or more, 0.4% by weight or more, or 0.6% by weight or less, 0.8% by weight or less, 1.0% by weight or less, or any range encompassed by these endpoints, such that the pH of the composition is 5 or higher, 6 or higher, or 7 or lower, 8 or lower, or 9 or lower, or any of these endpoints.

[0140] 5. Water-soluble inorganic and organic salts The water-soluble salt may consist of one or more defined components selected from water-soluble inorganic salts and water-soluble organic salts having 1 to 8 carbon atoms. In this specification, water solubility refers to a compound that can dissolve in 100 g of water at 20°C in amounts of 5 g or more. The water-soluble salt of the cleanser is hydrated and dissolved, thereby increasing the surface hydrophobicity of the entire skin cleansing agent composition.

[0141] Suitable water-soluble inorganic salts may include alkali metal hydroxides, as well as ammonium salts containing hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, triphosphate, pyrophosphate, and carbonate; for example, chlorides such as sodium chloride, potassium chloride, and magnesium chloride; sulfates such as sodium sulfate, potassium sulfate, magnesium sulfate, and aluminum sulfate; and carbonates such as sodium carbonate and sodium bicarbonate.

[0142] Suitable water-soluble organic salts having 1 to 8 carbon atoms may include salts of acids such as lactic acid, succinic acid, citric acid, tartaric acid, malic acid, maleic acid, and fumaric acid, which contain alkali metals, ammonium, etc., for example; monosodium citrate, disodium citrate, trisodium citrate, potassium lactate, ammonium succinate, potassium malate, etc.

[0143] 6. Water Water is present in the cleanser formulation in small amounts, approximately 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight, 45% by weight, 50% by weight, 55% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, or 80% by weight, or within any of the following ranges: 5% to 80% by weight, 10% to 70% by weight, 15% to 65% by weight, 20% to 60% by weight, or 25% to 50% by weight, or any range encompassed by these endpoints. This allows the cleanser to be rinsed off cleanly without leaving any residue, while maintaining sufficient cleansing power.

[0144] 7. Other additives The cleanser formulation may further contain ingredients commonly used in cleansing agents, typically such as thickeners, antibacterial agents, humectants, moisturizers, colorants, preservatives, feel improvers, fragrances, anti-inflammatory agents, skin whitening agents, antiperspirants, UV absorbers, antioxidants, and various types of extracts.

[0145] IV. Mascara This disclosure also provides mascara formulations. The mascara formulations of this disclosure provide low-wax and / or wax-free mascara compositions that give lashes good body and volume, are easy to apply to lashes, and produce a smooth, uniform layer with less clumping than conventional mascaras. The mascaras of the present invention are also easily removed with water and are less prone to peeling or smudging than conventional mascaras.

[0146] The mascara formulation may be in the form of an oil-in-water emulsion (O / W). The O / W emulsions of this disclosure comprise an oil phase (or lipophilic phase) dispersed in an aqueous phase. In such an emulsion, the aqueous phase is therefore the continuous phase of the composition, while the oil phase is the dispersed phase of the composition. The oil phase is present in an amount, on a weight basis relative to the total weight of the composition, within the range of about 3% by weight or more, about 5% by weight or more, about 10% by weight or more, about 15% by weight or more, about 20% by weight or more, about 25% by weight or more, or about 30% by weight or less, about 35% by weight or less, about 40% by weight or less, about 45% by weight or less, about 50% by weight or less, or any of the ranges encompassed by these endpoints.

[0147] The aqueous phase is present in an amount, on a weight basis relative to the total weight of the composition, that is approximately 25% by weight or more, approximately 30% by weight or more, approximately 35% by weight or more, 40% by weight or more, approximately 45% by weight or more, approximately 50% by weight or more, approximately 55% by weight or more, approximately 60% by weight or more, approximately 65% ​​by weight or more, or approximately 70% by weight or less, approximately 80% by weight or less, approximately 85% by weight or less, approximately 90% by weight or less, approximately 95% by weight or less, approximately 97% by weight or less, or within any of the ranges of 25% to 97% by weight, or 30% to 90% by weight, or 35% to 80% by weight, or 40% to 60% by weight, or within any of the ranges encompassed by these endpoints.

[0148] The pH of the emulsion of the present invention at 25°C is within the range of approximately 5.5 or higher, approximately 6.0 or higher, approximately 6.5 or higher, approximately 7.0 or higher, approximately 7.5 or lower, approximately 8.0 or lower, approximately 8.5 or lower, or any of these endpoints up to approximately 8.5, or approximately 7.3 ± 0.3.

[0149] The mascara may contain one or more film-forming systems comprising a liquid fatty substance, one or more surfactants selected from one or more surfactant classes, one or more rheology modifiers or viscosity increasers, at least one film-forming polymer, and at least one co-film-forming agent.

[0150] 1. Liquid fatty substances The liquid fatty substance may be selected from cetyl PEG / PPG-10 / 1 dimethicone, dimethicone (and) dimethiconol, and mixtures thereof. The liquid fatty substance may be present in the mascara formulation in amounts of about 0.1% by weight or more, about 1% by weight or more, about 5% by weight or more, about 10% by weight or more, or about 15% by weight or less, about 20% by weight or less, about 25% by weight or less, about 30% by weight or less, or any of these endpoints.

[0151] 2. Surfactants Mascara formulations, collectively referred to as surfactant systems, contain one or more surfactants selected from one or more surfactant classes. These surfactant systems function as emulsifiers for O / W emulsions.

[0152] Suitable surfactants used in the mascara formulations of this disclosure are those of formula I or II

[0153] [ka]

[0154] [In the formula, R 1 and R 2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. One or more surfactants and / or copolymers, and optionally soil penetration agents; foaming agents; foaming power enhancers; pH stabilizers; at least one thickener; fragrance, or water. Includes.

[0155] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, wherein the second molecule of formula I is the same as the first molecule of formula I.

[0156] More specifically, R 3 The following set of formulas may be selected.

[0157] [ka]

[0158] In particular, suitable surfactants or co-surfactants may include any one or more of Surfactants 1 to 12 described herein. The surfactant system is present in the mascara formulation in an amount of about 3% by weight or more, about 5% by weight or more, about 8% by weight or more, or about 10% by weight or less, about 15% by weight or less, about 20% by weight or less, or within any range using these endpoints.

[0159] 3. Rheology Modifier The rheology modifier or viscosity increasing agent may be selected from nonionic, anionic, cationic, and amphoteric polymers including gum such as cellulose-based paste (e.g., hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, cationic cellulose ether derivatives, quaternized cellulose derivatives, etc.), guar gum and its derivatives (e.g., hydroxypropyl guar, cationic guar derivatives, etc.), gums of microbial origin (e.g., xanthan gum, scleroglucan gum, etc.) and gums derived from plant extracts (e.g., gum arabic, ghatti gum, karaya gum, tragacanth gum, carrageenan gum, agar gum, and carob gum), pectin, alginate, and starch, crosslinked homopolymers of acrylic acid or acrylamide propanesulfonic acid, associative polymers, non-associative thickening polymers, water-soluble thickening polymers, and mixtures thereof, acrylate-based polymers, polysaccharides, polyamino compounds, amphiphilic polymers, and other viscosity modifiers.

[0160] Other suitable rheology modifiers or viscosity increasing agents include synthetic polymers such as glyceryl behenate, polyethylene and its copolymers such as PEG-150 distearate, magnesium stearate, polyacrylic acid (commercially available as Carbomers), and acrylate copolymers such as sodium polyacrylate and polyacryloyldimethyltaurate, and mixtures thereof.

[0161] The rheology modifier or viscosity increasing agent is present in the mascara formulation in an amount within any range of about 0.2 wt% or more, about 0.4 wt% or more, about 0.6 wt% or more, about 0.8 wt% or more, or about 1.0 wt% or less, about 1.2 wt% or less, about 1.4 wt% or less, about 1.6 wt% or less, about 3.0 wt% or less, about 4.0 wt% or less, about 5.0 wt% or less, or 0.2 wt% to 5.0 wt%, or 0.4 wt% to 4.0 wt%, or 0.6 wt% to 3.0 wt%, or 0.8 wt% to 2.0 wt%, or within any range using these endpoints.

[0162] 4. Film-forming system The mascara formulation includes a film-forming system comprising a first film-forming polymer and a second co-film-forming agent.

[0163] The first film-forming polymer may be selected from acrylate copolymers, styrene / acrylate copolymers, acrylamide / acrylate copolymers, polyurethanes, derivatives thereof, and mixtures thereof. The acrylate copolymer may be selected from copolymers containing two or more monomers selected from these simple esters exemplified by acrylic acid, methacrylic acid, and lower alkyl esters such as methyl, ethyl, and ethylhexyl esters. Suitable acrylate copolymers are ammonium acrylate copolymer, ethyl acrylate copolymer, acrylate / ethylhexyl acrylate copolymer, acrylate / octyl acrylate copolymer, alkyl (meth)acrylate copolymer, acrylate / C 12 ~C 22The material may also contain alkyl methacrylate copolymers, ethyl acrylate / methacrylic acid copolymers, and t-butyl acrylate / ethyl acrylate / methacrylic acid copolymers. Exemplary commercially available acrylate copolymers include, but are not limited to, ALLIANZ® OPT sold by Ashland Specialty Ingredients; COVACRYL A15 and COVACRYL E14 sold by Sensient Cosmetic Technologies LCW; DAITOSOL® 4000 SJT, DAITOSOL® 5000 AD, DAITOSOL® 5000 SJ, KOBOGUARD® 50A, and KOBOGUARD® 50N sold by Kobo Products, Inc.; DERMACRYL® AQF, YODOSOL 32A707, YODOSOL GH15, YODOSOL GH32, YODOSOL GH33, YODOSOL GH34, YODOSOL GH35, YODOSOL GH800, and YODOSOL GH810; including LUVIFLEX® SOFT, LUVIMER® 36D, and LUVIMER® 100P sold by BASF, and NEOCRYL® XK-90 sold by Neoresins, Inc.

[0164] The film-forming agent may also be selected from polyacrylates such as polyacrylate-21 and polyacrylate-15, as well as acrylate copolymers. The film-forming agent may also be selected from latex film-forming polymers such as polyacrylate latex, polyurethane latex, and copolymers thereof. Suitable examples of latex polymers include ethylhexyl acrylate / hema copolymer (and) acrylate / diethylaminoethyl methacrylate / ethylhexyl acrylate copolymer (Syntran® PC5775), styrene / acrylate / ammonium methacrylate copolymer (Syntran® 5760, Syntran® 5009, Syntran® PC5620), polyacrylate-21 (and) acrylate / dimethylaminoethyl methacrylate copolymer (Syntran® PC5100, Syntran® PC5776, Eudragit® E 100, Jurymer ET-410C), styrene / acrylate / ammonium methacrylate copolymer (Syntran® 5009CG), olefin / acrylate grafted polymer (and) sodium laureth sulfate (and C12-15 SEC-Pareth 15 (Syntran® EX108), acrylate copolymers (Aculyn® 33A polymer, Avalure® Ace 210 / 120 / 315 acrylic copolymer, Carbopol® Aqua SF-1 polymer, Daitosol® 500 AD, Coatex® Co 633, Ericlear® 380 / 700 / 4U, Eudragit® L 100, Joncryl® 85, Luviflex® Soft), acrylate / ethylhexyl acrylate copolymers (Daitosol® 5000SJ, Daitosol® 4000SJT, MJA PS34-21, SDP-001). Syntran® polymers are commercially available from supplier Interpolymer Corp.

[0165] Suitable examples of latex polymers are polyurethane-35, polyurethane-35, and polyurethane-35. The latex polymer may be an acrylate latex polymer, in particular a styrene / acrylate copolymer. Suitable commercially available styrene / acrylate copolymers include, but are not limited to, DAITOSOL® 5000 STY, sold by Kobo Products, Inc.; JONCRYL® 77, sold by BASF; NEOCRYL® BT-62, sold by Neoresins, Inc.; RHOPLEX® P-376 and UCAR® DL 432S, sold by Dow Chemical Company; and YODOSOL GH41 and YODOSOL GH840, sold by AkzoNobel.

[0166] The acrylamide / acrylate copolymer may be selected from acrylic acid / ethyl acrylate / t-butylacrylamide copolymer, acrylate / octylacrylamide copolymer, and octylacrylamide / acrylate / methacrylate copolymer. Exemplary commercially available acrylamide / acrylate copolymers include, but are not limited to, AMPHOMER® LV-71 and DERMACRYL® 79, marketed by AkzoNobel, and ULTRAHOLD® STRONG, marketed by BASF.

[0167] The co-film-forming agent may be a polymer such as divinyldimethicone / dimethicone copolymer, C12-13 Pareth-23, and C12-13 Pareth-3. The film-forming system is present in the mascara formulation in amounts of approximately 5% by weight or more, approximately 10% by weight or more, approximately 15% by weight or more, approximately 20% by weight or more, or approximately 25% by weight or less, approximately 30% by weight or less, approximately 35% by weight or less, approximately 40% by weight or less, or any of the endpoints within these ranges.

[0168] The film-forming system may contain the first film-forming polymer in an amount of approximately 7% by weight or more, approximately 10% by weight or more, approximately 15% by weight or more, or approximately 20% by weight or less, approximately 25% by weight or less, or any of these endpoints.

[0169] The film-forming system may contain a co-film-forming polymer in an amount of approximately 0.2% by weight or more, approximately 0.5% by weight or more, approximately 1% by weight or more, or approximately 2% by weight or less, approximately 3% by weight or less, approximately 4% by weight or less, approximately 5% by weight or less, or any of the endpoints within this range.

[0170] 5. Water The mascara formulation may contain water in an amount within any of the following ranges: approximately 5% by weight, approximately 10% by weight, approximately 15% by weight, approximately 20% by weight, approximately 25% by weight, approximately 30% by weight, approximately 35% by weight, approximately 40% by weight, approximately 45% by weight, approximately 50% by weight, approximately 55% by weight, approximately 60% by weight, approximately 65% ​​by weight, approximately 70% by weight, approximately 75% by weight, or approximately 80% by weight, or 5% to 80% by weight, or 10% to 70% by weight, or 15% to 65% by weight, or 20% to 60% by weight, or 25% to 50% by weight, or any range encompassed by these endpoints.

[0171] 6. Other additives Mascara formulations may contain coalescents and / or plasticizers. It is known that the inclusion of coalescents promotes the coalescence of polymer particles in aqueous dispersions, and the inclusion of plasticizers enables the plasticization of polymers in aqueous dispersions. Any coalescent / plasticizer may be used, and those skilled in the art will be able to select a suitable coalescent / plasticizer based, for example, the type of cosmetic composition to be formulated and its desired properties, with little or no experimental procedures.

[0172] Optional synthesizers and / or plasticizers may be selected from tributyl citrate, texanol ester alcohol, diisobutyl adipate, esters of tert-butyric acid with 2,2,4-trimethylpentane-1,3-diol, diethyl adipate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate, butyl 2-ethylhexyl phthalate, dimethyl sebacate, dibutyl sebacate, ethyl stearate, ethylhexyl palmitate, dipropylene glycol n-butyl ether, and mixtures thereof. As just one example, optional synthesizers may be selected from butylene glycol, caprylyl glycol, propylene glycol n-butyl ether, dipropylene glycol dibenzoate, dipropylene glycol dimethyl ether, propylene glycol methyl ether acetate, propylene glycol propyl ether, methyl lactate, ethyl lactate, isopropyl lactate, and mixtures thereof.

[0173] The cohesive agent and / or plasticizer may be present in the cosmetic composition in amounts of about 0.1% by weight or more, about 1% by weight or more, about 2% by weight or more, about 4% by weight or more, or about 6% by weight or less, about 8% by weight or less, about 10% by weight or less, or any of these endpoints.

[0174] Mascara formulations may also contain one or more emollients / moisturizers. These compounds replenish moisture to the eyelashes and also provide a "wet" texture and glossy appearance. Useful emollients include, but are not limited to, carnauba wax, beeswax, mineral oil, almond oil, castor oil, sesame oil, hydrogenated polyisobutene, butylene glycol dicaprylate dicaprate (commercially available from Sasol as Myglyol®), and mixtures thereof. PEG-12 dimethicone, and even dimethicone / dimethicol, may also be used as emollients.

[0175] Mascara formulations may contain at least one pigment (or dye). Suitable pigments / dyes include, but are not limited to, finely powdered dyes, lipid-soluble dyes, and water-soluble dyes. Finely powdered dyes may be selected from, for example, pigments and nacres. Suitable pigments include titanium dioxide, zirconium oxide, zinc oxide, cerium oxide, iron oxide, chromium oxide, manganese violet, ultramarine blue, hydrated chromium oxide, and ferric blue. Not limited examples of organic pigments include carbon black, D&C type pigments, and lakes based on cochineal carmine, barium, strontium, calcium, and aluminum.

[0176] Pearlescent substances that may be used include, for example, colored pearlescent pigments such as titanium mica containing iron oxide, titanium mica containing ferric blue or chromium oxide, titanium mica containing organic pigments selected from the above list, and pearlescent pigments based on bismuth oxychloride.

[0177] At least one pigment / dye may be present in the mascara formulation in amounts of approximately 1% by weight or more, approximately 5% by weight or more, approximately 10% by weight or more, approximately 15% by weight or more, approximately 20% by weight or more, or approximately 25% by weight or less, approximately 30% by weight or less, approximately 35% by weight or less, approximately 40% by weight or less, or any of these endpoints.

[0178] Mascara formulations may further include fillers, fibers, solvents, dispersants, antioxidants, preservatives, fragrances, additional thickeners or texturers, liquid lipids / oils, additional viscosity modifiers, additional film-forming agents, sunscreens, additional pigments / colorants / dyes, silica, clay, humectants and moisturizers, emulsifiers, additional structuring agents and fillers, surfactants, glossants, conditioning agents, cosmetic, dermatological and pharmaceutically active agents, vitamins, plant extracts, additional film-forming agents, synthesizers / plasticizers, pH adjusters / neutralizers, stabilizers, and mixtures thereof.

[0179] V. Toothpaste This disclosure further provides toothpaste formulations. Toothpaste formulations may be used to improve oral health, remove stains, and prevent tooth decay.

[0180] The kneaded toothpaste composition may contain a basic amino acid in free form or salt form, calcium carbonate, a fluoride ion source, a flavoring agent, one or more surfactants selected from one or more surfactant classes, water, and other optional additives.

[0181] 1. Amino Acid The kneaded toothpaste composition may contain a basic amino acid in free form or salt form. Suitable amino acids include not only natural basic amino acids such as arginine, lysine, and histidine, but also any basic amino acid that is water-soluble and gives an aqueous solution with a pH of about 7 or higher and has a carboxyl group and an amino group in the molecule. For example, basic amino acids may include, but are not limited to, arginine, lysine, citrulline, ornithine, creatine, histidine, diaminobutyric acid, diaminopropionic acid, salts thereof, and combinations thereof. In certain embodiments, the basic amino acid may include arginine, citrulline, ornithine, and salts and combinations thereof.

[0182] The basic amino acid may be in free form or salt form. In the case of a salt, such salt must be pharmaceutically acceptable. The basic amino acid may be a salt derived from a pharmaceutically acceptable inorganic or organic acid or base, for example an acid addition salt formed by an acid that forms a physiologically acceptable anion, such as a hydrochloride or hydrobromide salt, or a base addition salt formed by a base that forms a physiologically acceptable cation such as an alkali metal or alkaline earth metal such as potassium, sodium, calcium or magnesium. The basic amino acid may be a bicarbonate of the amino acid.

[0183] The basic amino acid in free form or salt form is present in an amount of 0.5% by weight or more, about 1% by weight or more, about 2% by weight or more, or about 3% by weight or less, about 4% by weight or less, about 5% by weight or less, or within any range using these endpoints.

[0184] 2. Calcium carbonate Toothpaste formulations may contain calcium carbonate. Natural calcium carbonate is found in rocks such as chalk, limestone, marble, and travertine, as well as in eggshells and seashells. Natural calcium carbonate may be used as an abrasive in oral care compositions. Typically, natural calcium carbonate abrasives are finely ground limestone, which may be optionally purified or partially purified to remove impurities. In certain embodiments, natural calcium carbonate has an average particle size of less than 10 microns, for example, 3 to 7 microns or about 5.5 microns.

[0185] The toothpaste formulation may also contain additional calcium-containing abrasives, such as calcium phosphate abrasives like tricalcium phosphate, hydroxyapatite, or dicalcium phosphate dihydrate. In certain embodiments, the composition may include silica abrasives such as precipitated silica, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite, or other siliceous materials, and / or combinations thereof, having an average particle size up to about 20 μm.

[0186] The amount of calcium carbonate in the toothpaste formulation may be approximately 20% by weight or more, approximately 25% by weight or more, approximately 30% by weight or more, approximately 35% by weight or more, or approximately 40% by weight or less, approximately 45% by weight or less, approximately 50% by weight or less, approximately 55% by weight or less, approximately 60% by weight or less, or any of the endpoints of these ranges.

[0187] 3. Fluoride ion source The composition may contain one or more fluoride ion sources, such as soluble fluoride salts. Suitable fluoride ion sources include stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium, fluorosilicates, fluoramines, ammonium fluoride, and one or more combinations thereof.

[0188] The fluoride ion source may be present in an amount sufficient to supply from about 25 ppm to about 25,000 ppm of fluoride ions, such as from about 500 ppm to about 200 ppm, from about 1000 ppm to about 1600 ppm.

[0189] The weight of the fluoride salt may be selected to provide a suitable level of fluoride ions in the dentifrice formulation. The fluoride salt may be present in an amount of about 0.01% by weight or more, about 1% by weight or more, about 2% by weight or more, about 4% by weight or more, or about 6% by weight or less, about 8% by weight or less, about 10% by weight or less, or within any range using these endpoints.

[0190] 4. Surfactant The dentifrice formulation includes one or more surfactants selected from one or more surfactant classes. The surfactant functions as a stabilizer as the dentifrice formulation.

[0191] Surfactants suitable for use in the dentifrice formulations of the present disclosure are of Formula I or II

[0192] [Chemical formula]

[0193] [wherein, R 1 and R 2 may be the same or different and each contains at least one group selected from the group consisting of C1-C6 alkyl, and optionally, the C1-C6 alkyl may contain one or more oxygen, nitrogen or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 is alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10Alkyl benzoic acid, and C1-C bonded to an additional surfactant molecule having a structure represented by Formula I 12 It may be selected from the group consisting of a linker, and the additional surfactant molecule of Formula I may be the same as or different from the surfactant molecule of Formula I; n and z may be independently selected from any integer from 1 to 12; m may be any integer from 1 to 12; X may be selected from the group consisting of chloride, bromide, and iodide One or more surfactants and / or cosurfactants of; And optionally, a soil penetrant; a foaming agent; a foaming power enhancer; a pH stabilizer; at least one thickener; a fragrance, or water Comprising.

[0194] Specifically, R 3 Is C2-C 10 Alkenyl, C2-C 10 Alkynyl, C2-C 12 Ester, C1-C 10 Hydroxyl, benzyl, C2-C 12 Alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C5 alkyl benzoic acid, and a 3-carbon linker bonded to a second molecule of Formula I, and the second molecule of Formula I is the same as the first molecule of Formula I.

[0195] More specifically, R 3 May be selected from the group consisting of the following formulas.

[0196]

Chemical formula

[0197] In particular, suitable surfactants or cosurfactants may include any one or more of surfactants 1 to 12 described herein. One or more surfactants are present in the toothpaste formulation in amounts of approximately 1.0% or more by weight, approximately 1.1% or more by weight, approximately 1.2% or more by weight, approximately 1.3% or less by weight, approximately 1.4% or less by weight, or within any of these endpoints.

[0198] 5. Flavoring agents Toothpaste formulations may contain flavoring agents. Flavoring agents may include one or more essential oils, as well as various flavor aldehydes, esters, and / or alcohols. Suitable flavoring agents may include one or more essential oils selected from peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, grapefruit, and orange oils.

[0199] Flavoring agents may be present in the composition in amounts of approximately 0.1% by weight or more, approximately 1.2% by weight or more, approximately 1.4% by weight or more, or approximately 1.6% by weight or less, approximately 1.8% by weight or less, approximately 2.0% by weight or less, or any of these endpoints.

[0200] 6. Other additives Toothpaste formulations may also contain other additives, such as antibacterial preservatives like benzyl alcohol.

[0201] Benzyl alcohol may be present in toothpaste formulations in amounts of approximately 0.2% by weight or more, approximately 0.3% by weight or more, approximately 0.4% by weight or more, approximately 0.5% by weight or more, or approximately 0.6% by weight or less, approximately 0.7% by weight or less, approximately 0.8% by weight or less, or any of these endpoints.

[0202] The toothpaste formulation may also contain polyethylene glycol, polyvinyl methyl ether maleate copolymer, and one or more polymers such as polysaccharides (e.g., cellulose derivatives such as carboxymethylcellulose or microcrystalline cellulose, or polysaccharide gums such as xanthan gum or carrageenan gum). The acidic polymer, such as polyacrylate gel, may be provided as a free acid or a partially or completely neutralized water-soluble alkali metal (e.g., potassium and sodium) salt or ammonium salt.

[0203] The toothpaste formulation may also contain one or more wetting agents. The wetting agents can prevent the composition from hardening when exposed to air. In certain embodiments, the composition contains one or more wetting agents selected from edible polyhydric alcohols such as glycerin, sorbitol, xylitol, propylene glycol, and mixtures thereof.

[0204] 7. Manufacturing Method The disclosure further provides a method for preparing a formulation for use as a toothpaste. The method may include the following series of steps: a) adding a basic amino acid to a solution containing a fluoride ion source; b) adding calcium carbonate; and c) adding an anionic surfactant.

[0205] VI. Surfactants This disclosure provides surfactants for use in personal care products in the form of amino acid siloxane derivatives. Accordingly, the use of compounds of formula I or II as surfactants in personal care products is disclosed herein.

[0206] This disclosure relates to formula I or II

[0207] [ka]

[0208] [In the formula, R 1 and R2 The groups may be the same or different, and each group comprises at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid and additional surfactant molecules having the structure represented by formula I are bonded to C1-C12. 12 The additional surfactant molecules of formula I may be selected from the group consisting of linkers, and the additional surfactant molecules of formula I may be the same as or different from the surfactant molecules of formula I; n and z may be independently chosen from any integer between 1 and 12; m can be any integer between 1 and 12; X may be selected from the group consisting of chloride, bromide, and iodide. We provide surfactants used in personal care products in the form of surfactant molecules.

[0209] Specifically, R 3 C2~C 10 Alkenyl, C2~C 10 Alkinyl, C2~C 12 Ester, C1~C 10 Hydroxyl, benzyl, C2-C 12 The second molecule of formula I may be selected from the group consisting of alkoxyalkyl ethers, alkyl phosphates, alkyl phosphonates, C3-C8 carboxylic acids, C1-C5 alkylbenzoic acids, and a 3-carbon linker bonded to the second molecule of formula I, wherein the second molecule of formula I is the same as the first molecule of formula I.

[0210] More specifically, R 3The following set of formulas may be selected.

[0211] [ka]

[0212] The above discloses formulations containing at least one surfactant of formula I or II for use in various personal care products. The following disclosures of compounds of formula I and II apply to any of the compounds of formula I and II in the uses and formulations described herein.

[0213] Further compounds provided by this disclosure are those compounds of formula I, wherein R1 and R2 are methyl. Other compounds provided by this disclosure are compounds of formula I, where n and / or z are 5.

[0214] As used herein, the phrase “n may be an integer from 1 to 12” means that n may be equal to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0215] As used herein, the term "C1-C6 alkyl" means a linear or branched alkyl group containing 1, 2, 3, 4, 5, and / or 6 carbon atoms. As used herein, the term "C1-C6 linker" means a linear or branched alkyl chain containing 1, 2, 3, 4, 5, and / or 6 carbon atoms.

[0216] As used herein, the term "C2-C10 alkenyl" means a linear or branched alkenyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbon atoms.

[0217] As used herein, the term "C2-C10 alkynyl" means a linear or branched alkynyl group containing 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbon atoms.

[0218] As used herein, the term "C2-C12 ester" means a linear or branched ester group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbon atoms.

[0219] As used herein, the term "C2-C12 alkoxyalkyl ether" means a linear or branched alkoxyalkyl ether group having a total of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12 carbon atoms.

[0220] As used herein, the term "C1-C10 hydroxyl" means a hydroxyl atom bonded to a linear or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9, and / or 10 carbon atoms.

[0221] As used herein, the term "C3-C8 carboxylic acid" means a carboxylic acid group bonded to a linear or branched alkyl group containing 3, 4, 5, 6, 7, and / or 8 carbon atoms.

[0222] As used herein, the term "C1-C10 alkylbenzoic acid" means a benzoic acid group bonded to a linear or branched alkyl group containing 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10 carbon atoms.

[0223] As used herein, the phrase "n and z may be independently selected from any integer between 1 and 12" means that n and z may independently be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0224] As used herein, the phrase “m may be any integer from 1 to 12” means that m may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and / or 12.

[0225] As used herein, the phrase "q may be any integer from 1 to 10" means that q may be 1, 2, 3, 4, 5, 6, 7, 8, 9 and / or 10.

[0226] One specific compound provided by this disclosure 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)propylamino)-N,N-dimethyl-6-oxohexane-1-aminium bromide having the following formula:

[0227] [ka]

[0228] The second specific compound provided by this disclosure 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-oxohexane-1-aminium bromide having the following formula:

[0229] [ka]

[0230] A third specific compound provided by this disclosure 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-oxohexane-1-aminium iodide having the following formula:

[0231] [ka]

[0232] A fourth specific compound provided by this disclosure 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-(propa-2-in-1-yl)hexane-1-aminium bromide having the following formula:

[0233] [ka]

[0234] A fifth specific compound provided by this disclosure 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-oxohexane-1-aminium bromide having the following formula:

[0235] [ka]

[0236] The sixth specific compound provided by this disclosure 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-oxohexane-1-aminium bromide having the following formula:

[0237] [ka]

[0238] The seventh specific compound provided by this disclosure 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-oxohexane-1-aminium iodide having the following formula:

[0239] [ka]

[0240] The eighth specific compound provided by this disclosure 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-oxohexane-1-aminium iodide having the following formula:

[0241] [ka]

[0242] The ninth specific compound provided by this disclosure 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-oxohexane-1-aminium bromide having the following formula:

[0243] [ka]

[0244] A tenth specific compound provided in this disclosure and referred to herein as surfactant 10 is an N compound having the following formula: 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 It is tetramethylpropane-1,3-diaminium dibromide.

[0245] [ka]

[0246] A further group of specific compounds provided herein and referred to herein as surfactants 11-12 are general formulas:

[0247] [ka]

[0248] [In the formula, q may be an integer between 1 and 10.] It holds. The 11th specific compound provided by this disclosure 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-oxohexane-1-aminium bromide having the following formula:

[0249] [ka]

[0250] The twelfth specific compound provided by 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-oxohexane-1-aminium bromide having the following formula:

[0251] [ka]

[0252] These compounds can be synthesized by various methods. One such method involves reacting an amino acid, such as 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. The N-terminus of the amino acid may be further alkylated to obtain, for example, a quaternary amine.

[0253] The amino acids may be natural or synthetic, or they may be derived from the ring-opening reaction of lactams such as caprolactam. The ring-opening reaction may be acid-catalyzed or alkali-catalyzed, and an example of an acid-catalyzed reaction is shown in Scheme 1 below.

[0254] [ka]

[0255] An amino acid may have at least one or as many as twelve carbon atoms between its N-terminus and C-terminus, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms. The alkyl chain may be branched or linear. The alkyl chain may contain nitrogen, oxygen, or sulfur atoms. The alkyl chain may further be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carboxyl, and carboxylate. The N-terminal nitrogen may be acylated or alkylated with one or more alkyl groups. For example, the amino acid may be 6-(dimethylamino)hexanoic acid.

[0256] The siloxane may be substituted with one or more alkoxy groups such as methoxy, ethoxy, isopropoxy, or tert-butoxy. The siloxane may be further substituted with one or more alkyl groups such as propyl, in which case the alkyl group may be further substituted with a suitable functional group that enables coupling of the siloxane to an amino acid, such as nitrogen. For example, the siloxane may be 3-aminopropyltris(trimethylsiloxy)silane.

[0257] The siloxane derivatives of amino acids may be synthesized as shown in Scheme 2 below. As shown therein, 6-aminohexanoic acid is alkylated at its N-terminus by treatment with formaldehyde in formic acid under reflux to obtain 6-(dimethylamino)hexanoic acid. This free carboxylic acid is then coupled to 3-aminopropyl(trismethylsiloxy)silane in refluxed toluene to obtain the desired siloxane derivative.

[0258] [ka]

[0259] The N-terminal nitrogen may be further derivatized to modify or improve water solubility and surface activity properties. A sample synthesis scheme is shown in Scheme 3 below, in which case the N-terminal nitrogen is alkylated to obtain a quaternary amine.

[0260] [ka]

[0261] Suitable alkylating agents may include, for example, benzyl bromide, ethyl bromo, allyl iodide, propargyl bromide, 1-bromo-2-(2-methoxyethoxy)ethane, bromophosphonate, 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 may be linked by treating the N-terminal nitrogen with a bifunctional alkylating agent such as 1,3-dibromopropane.

[0262] The compounds disclosed herein exhibit surface-active properties. These properties can be measured and described by various methods. One way to describe surfactants is by the critical micelle concentration (CMC) of the molecule. CMC may be defined as the concentration of surfactant that forms micelles, at concentrations higher than this, all additional surfactant is incorporated into the micelles.

[0263] As the surfactant concentration increases, the surface tension decreases. When the surface is completely covered with surfactant molecules, micelles begin to form. This point represents the CMC, and thus the minimum surface tension. Adding more surfactant does not further affect the surface tension. Therefore, the CMC can be measured by observing the change in surface tension as a function of surfactant concentration. One such method for measuring this value is the Wilhelmie plate method. A Wilhelmie plate is typically a thin iridium-platinum plate attached to a balance by wire and positioned perpendicular to the air-liquid interface. Using the balance, the force acting on the plate due to wetting is measured. Then, using this value, the surface tension (γ) is calculated according to Equation 1: Equation 1: γ = F / l cosθ In the formula, l is equal to the wet perimeter (2w + 2d, where w and d are the thickness and width of the plate, respectively), and the contact angle cosθ between the liquid and the plate is assumed to be 0 if there are no existing literature values.

[0264] Another parameter used to evaluate the performance of surfactants is dynamic surface tension. Dynamic surface tension is the value of surface tension over time at a particular surface or interface. In the case of a liquid to which a surfactant has been added, this can differ from the equilibrium value. Immediately after the surface is formed, the surface tension is equal to that of the pure liquid. As mentioned above, surfactants decrease the surface tension, so the surface tension decreases until it reaches the equilibrium value. The time required to reach equilibrium depends on the diffusion rate and adsorption rate of the surfactant.

[0265] One method for measuring dynamic surface tension is using a bubble-type tension meter. This device measures the maximum internal pressure of bubbles formed in a liquid by a capillary. The measured value corresponds to the surface tension at a specific surface elapsed time, which is the time from the start of bubble formation until the maximum pressure is reached. The dependence of surface tension on surface elapsed time can be measured by varying the rate at which bubbles are formed.

[0266] Surface-active compounds can also be evaluated by their wetting ability on solid substrates, measured by the contact angle. When a droplet comes into contact with a solid surface in a third medium such as air, a three-phase line is formed between the liquid, gas, and solid. The contact angle is described as the angle between the surface and the unit vector of surface tension, which plays a role in the three-phase line and is tangent to the droplet. The contact angle (also known as the wetting angle) is a measure of how well a liquid wets a solid. In the case of complete wetting, the liquid spreads completely over the solid, and the contact angle is 0°. Wetting properties are typically measured at concentrations of 1 to 100 × CMC for a given compound, but they are not concentration-dependent. Therefore, wetting properties may be measured at higher or lower concentrations. One method involves using an optical contact angle goniometer to measure the contact angle. This device uses a digital camera and software to analyze the contour shape of a stationary liquid droplet on a surface to determine the contact angle.

[0267] Possible applications of the surface-active compounds disclosed herein include formulations for use in shampoos, hair conditioners, detergents, spot-free rinse solutions, floor and carpet cleaners, graffiti removers, crop protection wetting agents, crop protection auxiliaries, and aerosol spray coatings.

[0268] Those skilled in the art will understand that even slight differences between compounds can lead to significantly different surfactant properties, and therefore different compounds may be used for different substrates and different applications. Those skilled in the art will also understand that surfactant properties are not always predictable based on chemical structure, as will be further demonstrated below. For example, surfactant 9 and the comparative surfactant differ only in the number of methylene groups at R3, but they demonstrate different surfactant properties. Surprisingly, surfactant 9 exhibits superior activity, as further described below, while the comparative surfactant exhibits inferior surfactant properties.

[0269] The following non-limiting embodiments are given to demonstrate the different properties of different surfactants. In Table 1 below, the abbreviations of the surfactants are associated with their corresponding chemical structures.

[0270] [Table 1-1]

[0271] [Table 1-2]

[0272] [Table 1-3]

[0273] These compounds are effective as surfactants in any of the formulations envisioned by this disclosure and may be useful as wetting or foaming agents, dispersants, emulsifiers, and detergents.

[0274] The amount of the compounds disclosed herein used in the formulation may be as low as about 0.001% by weight, about 0.05% by weight, about 0.1% by weight, about 0.5% by weight, about 1% by weight, about 2% by weight, or about 5% by weight; or as high as about 8% by weight, about 10% by weight, about 15% by weight, about 20% by weight, or about 25% by weight, about 30% by weight, about 40% by weight, about 50% by weight, or about 80% by weight; or within any range of 0.001% to 80% by weight, or 0.05% to 50% by weight, or 0.1% to 20% by weight, or 0.5% to 10% by weight, or 1% to 8% by weight, or 2% to 8% by weight, or 5% to 8% by weight, or any range using any two of the aforementioned values.

[0275] Table 2 includes comparative surfactants, including their names and structures.

[0276] [Table 2]

[0277] Useful surfactants 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 within the range encompassed by the aforementioned endpoints. For example, a 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.

[0278] Useful surfactants in the formulations disclosed herein may have minimum surface tension plateau values ​​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 they may have any minimum surface tension plateau value within the range encompassed by the aforementioned endpoints. For example, a surfactant may have a minimum surface tension plateau value of about 15 to about 25 mN / m, about 18 to about 22 mN / m, or about 20 to about 21 mN / m.

[0279] Surfactants with antibacterial properties Cells are the basic units of all living organisms, and all have a group of organelles responsible for the ability of each cell to perform various kinds of functions and store genetic information about the growth and function of the organism. The outer boundary of the cell is called the cell membrane, and it functions as a barrier, controlling the transport of substances between the inside and outside of the cell. The cell membrane is destroyed by a process called lysis, which causes cell death, and this is the root cause of all antimicrobial processes. The use of surfactants with inherent biocidal activity in shampoos, conditioners, cleansers, and various other applications can be very important, especially in situations where the application cannot tolerate the use of chemical biocides.

[0280] 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 degrading bacterial membranes through 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)). To function as an effective antimicrobial agent, surfactants must effectively kill bacteria or other undesirable pathogenic microorganisms without adversely affecting mammalian cells. Today, with increasing awareness of the potential cytotoxicity and environmental risks of certain chemicals, conventional quaternary ammonium surfactants are known to indiscriminately disrupt biological membranes regardless of cell type, and efforts are being made to develop surfactants that mitigate concerns about potential cytotoxicity arising from their lack of selectivity.

[0281] To evaluate the antimicrobial activity known as the minimum inhibitory concentration (MIC) test, the surfactants of this disclosure are shown in the standard protocol. The following table shows the MIC results for examples of the surfactants of this disclosure.

[0282] [Table 3] [Examples]

[0283] Nuclear magnetic resonance (NMR) spectroscopy was performed using a Bruker 500 MHz spectrometer. The critical micelle concentration (CMC) was determined at 23°C using a Wilhelmie plate method with a tensile strength meter (DCAT 11, DataPhysics Instruments GmbH) equipped with a Pt-Ir plate. Dynamic surface tension was determined at 23°C using a bubble pressure tensile strength meter (Kruss BP100, Kruss GmbH). The contact angle was determined using an optical contact angle goniometer (OCA 15 Pro, DataPhysics GmbH) equipped with a digital camera.

[0284] Example 1: Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)hexanamide 6-(dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equivalent) was dissolved in toluene (50 mL) in a 100 mL round-bottom boiling flask equipped with a Dean-Stark trap, and then 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equivalents) was added. The reaction vessel was heated and the reaction mixture was refluxed for 24 hours until no more water separated into the Dean-Stark tube. The solvent was removed under vacuum to obtain 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).

[0285] Example 2a: Synthesis of N-benzyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide (surfactant 1)

[0286] [ka]

[0287] 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 at 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 as a yellow solid (1.1 g).

[0288] Example 2b: Determination of the physical properties of surfactant 1 The critical micelle concentration (CMC) of surfactant 1 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 9.883 mmol at pH 8. The minimum surface tension plateau value achievable with this surfactant was approximately 20.67 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 1 as surface tension versus concentration.

[0289] Example 3a: Synthesis of 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-oxohexane-1-aminium bromide (surfactant 2)

[0290] [ka]

[0291] The siloxane derivative described in Example 1 (1 g, 2.02 mmol) was dissolved in DMF (15 mL), and ethyl bromoethyl (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 as a brown liquid (900 mg).

[0292] Example 3b: Determination of the physical properties of surfactant 2 The critical micelle concentration (CMC) of surfactant 2 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.2171 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.36 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 2 as surface tension versus concentration.

[0293] Example 4a: Synthesis of N-allyl-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium iodide (surfactant 3)

[0294] [ka]

[0295] To acetonitrile (10 mL), the siloxane derivative described in Example 1 (1.00 g, 2.02 mmol), followed by sodium carbonate (0.26 g), and then allyl iodide (674 mg) was added. The reaction mixture was refluxed at 40°C for 14 hours. Residual sodium carbonate was removed by filtration, and the filtrate was concentrated. To remove excess allyl iodide, the crude product was washed twice with hexane to obtain surfactant 3 as a brown liquid (850 mg).

[0296] Example 4b: Determination of the physical properties of surfactant 3 The critical micelle concentration (CMC) of surfactant 3 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 1.3599 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.67 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted as surface tension versus concentration in Figure 3.

[0297] Example 5a: Synthesis of 6-((3-(1,1,1,5,5,5-Hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxo-N-(propa-2-in-1-yl)hexano-1-aminium bromide (surfactant 4)

[0298] [ka]

[0299] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in dimethylformamide (DMF) (15 mL). Propargyl 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 as a brown liquid (850 mg).

[0300] Example 5b: Determination of the physical properties of surfactant 4 The critical micelle concentration (CMC) of surfactant 4 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.2419 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.54 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 4 as surface tension versus concentration.

[0301] Example 6a: Synthesis of 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-oxohexane-1-aminium bromide (surfactant 5)

[0302] [ka]

[0303] 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 as a brown liquid (800 mg).

[0304] Example 6b: Determination of the physical properties of surfactant 5 The critical micelle concentration (CMC) of surfactant 5 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.4622 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.40 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 5 as surface tension versus concentration.

[0305] Example 7a: Synthesis of 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-oxohexane-1-aminium bromide (surfactant 6)

[0306] [ka]

[0307] 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 as a brown liquid (900 mg).

[0308] Example 7b: Determination of the physical properties of surfactant 6 The critical micelle concentration (CMC) of surfactant 6 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.3989 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.48 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 6 as surface tension versus concentration.

[0309] Example 8a: Synthesis of 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(3-hydroxypropyl)-N,N-dimethyl-6-oxohexane-1-aminium iodide (surfactant 7)

[0310] [ka]

[0311] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) was dissolved in acetonitrile (10 mL). Sodium carbonate (0.26 g), followed by 3-iodopropanol (674 mg), was added. The mixture was stirred at 40°C for 24 hours. Residual base was removed by filtration, and the filtrate was concentrated. The crude product was washed twice with hexane to remove excess iodopropanol, and surfactant 7 was obtained as a brown liquid (780 mg).

[0312] Example 8b: Determination of the physical properties of surfactant 7 The critical micelle concentration (CMC) of surfactant 7 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.4568 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.61 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 7 as surface tension versus concentration.

[0313] Example 9a: Synthesis of 6-((3-(1,1,1,5,5,5-Hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N-(2-hydroxyethyl)-N,N-dimethyl-6-oxohexane-1-aminium iodide (surfactant 8)

[0314] [ka]

[0315] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) 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).

[0316] Example 9b: Determination of the physical properties of surfactant 8 The critical micelle concentration (CMC) of surfactant 8 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.9986 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.41 mN / m, indicating that the surfactant possesses significant surface activity. These results are plotted in Figure 8 as surface tension versus concentration.

[0317] 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 Synthesis of tetramethylpropane-1,3-diaminium dibromide (surfactant 10)

[0318] [ka]

[0319] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) 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 as a brown liquid (900 mg).

[0320] Example 10b: Determination of the physical properties of surfactant 10 The critical micelle concentration (CMC) of surfactant 10 was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.0631 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 22.12 mN / m, indicating that the surfactant possesses surface activity. These results are plotted in Figure 10 as surface tension versus concentration.

[0321] Example 11a: Synthesis of N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide (surfactant 9)

[0322] [ka]

[0323] 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, and then the solvent was removed under vacuum. The crude product was washed twice with hexane to obtain N-(5-carboxypentyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide as a viscous brown liquid (650 mg).

[0324] Example 11b: Determination of the physical properties of surfactant 9 The critical micelle concentration (CMC) of surfactant 9a was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 0.2237 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 20.52 mN / m, demonstrating that this surfactant possesses excellent surface activity. These results are plotted in Figure 9 as surface tension versus concentration.

[0325] Comparative Example A1: Synthesis of N-(carboxymethyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide (comparative surfactant)

[0326] [ka]

[0327] The siloxane derivative described in Example 1 (1.00 g, 2.02 mmol) 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 as a brown liquid (700 mg).

[0328] Comparative Example A2: Determination of the physical properties of the comparative surfactant. The critical micelle concentration (CMC) of surfactant 9b was measured. From the change in surface tension with respect to concentration in water, the CMC was determined to be approximately 17.28 mmol. The minimum surface tension plateau value achievable with this surfactant was approximately 29.16 mN / m. These results are plotted in Figure 11 as surface tension versus concentration. The results illustrate the difficulty in predicting surfactant activity based on chemical structure; surfactant 9, which differs only in the number of methylene groups in the carboxylic acid, exhibits remarkably superior activity.

[0329] Example 12: Synthesis of 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-oxohexane-1-aminium bromide (surfactant 11)

[0330] [ka]

[0331] 4-(4-bromobutyl)benzoic acid is added to the siloxane derivative described in Example 1 to obtain 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-oxohexane-1-aminium bromide.

[0332] Example 13: Synthesis of N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide (surfactant 12)

[0333] [ka]

[0334] 4-(bromomethyl)benzoic acid is added to the siloxane derivative described in Example 1 to obtain N-(4-carboxybenzyl)-6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxane-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexane-1-aminium bromide.

[0335] Example 14: Shampoo formulation This embodiment provides a formulation for use as a shampoo. This formulation is useful for giving hair a smooth and silky feel. The components of the formulation are shown in Table 3 below. In addition, the formulation may contain other natural oils and raw materials, as well as vitamins, in amounts of less than 1% by weight for consumer appeal.

[0336] [Table 4]

[0337] Example 15: Formula for hair conditioner This embodiment provides formulations for use as hair conditioners. These formulations may be used to replace or reduce polyquaternium-10, polyquaternium-7, and dimethicone oil while retaining the smooth combability and silky, soft feel that hair conditioners provide. The formulations are shown in Table 4 below.

[0338] [Table 5]

[0339] Example 16: Cleanser formulation This embodiment provides a formulation for use as a cleanser. This formulation may be used for cleansing the skin and removing makeup. Fatty components such as liquid oil may be used to help remove oily makeup. The formulation is shown in Table 5 below.

[0340] [Table 6]

[0341] Example 17: Mascara formulation This embodiment provides a formulation for use as a mascara. This formulation can be used for cleansing the skin and removing makeup. Fatty components such as liquid oil can be used to help remove oily makeup. The formulation is shown in Table 6 below.

[0342] [Table 7]

[0343] Example 18: Toothpaste formulation This embodiment provides a formulation for use as toothpaste. The formulation is shown in Table 7 below.

[0344] [Table 8]

[0345] Example 19: Antimicrobial MIC Survey The antimicrobial properties of surfactants were tested using known methods and standard protocols, targeting various types of microorganisms. More specifically, a minimum inhibitory concentration (MIC) test protocol using serial dilution was applied to obtain concentration-dependent microbial growth inhibition measurements against Gram-positive bacteria (e.g., the anaerobic Streptococcus mutans, and Staphylococcus aureus, which is normally aerobic but can also grow anaerobically) and Gram-negative bacteria (e.g., the anaerobic Escherichia coli, or the aerobic Psudomonas aeruginosa).

[0346] The bacteria were grown overnight in appropriate growth medium, tripty soy broth. Prior to testing, the concentration of the organisms to be tested was measured using a spectrophotometer capable of measuring optical density. These bacterial samples were then diluted to approximately 1E3–1E4 CFU / mL. Subsequently, 10 mL of the prepared bacterial culture was inoculated into the test wells of a 96-well plate, each containing appropriate growth medium (tripty soy agar). After inoculation with the bacterial culture, these wells were treated with serially diluted test samples and incubated for approximately 24±1 hours at a temperature of 37±1°C and a relative humidity of 90% or higher.

[0347] The surfactants to be tested were prepared in a dilution series. All dilutions were performed stepwise in 96-well microtiter plates using a multichannel pipette. The dilution series was pre-established by a range exploration test to determine the upper limit of high concentrations, and by a low-concentration dilution series to ensure that the test substance was effective without completely inhibiting bacterial growth.

[0348] Next, the approximate concentration of the test surfactant that inhibits bacterial growth was determined using an MIC (Micro-Intensity Monitor). In this antimicrobial testing protocol, a reference substance is typically used as a positive control. In this case, ADBAC, a quaternary amine with CAS number 139-08-2, was used as the appropriate test reference substance.

[0349] Test measurements were repeatedly performed in 96-well plates, and the measured MICs were reported as the integer mean. Repeated data were averaged by calculating the arithmetic mean of the selected measurements using the following formula: Arithmetic mean = Sum of values ​​in the set / Number of terms. Measurement variability was reported in the form of MIC+ / - based on the calculated mean.

[0350] manner Embodiment 1 is Equation I:

[0351] [ka]

[0352] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; Also, optionally a foaming agent; and water It is a shampoo formulation containing [the specified ingredient].

[0353] Embodiment 2 is the formulation of Embodiment 1, further comprising a foaming agent. Embodiment 3 is a formulation of either Embodiment 1 or Embodiment 2, further comprising at least one type of thickener.

[0354] Embodiment 4 is a formulation of any of Embodiments 1 to 3, further comprising a pH stabilizer. Embodiment 5 is a formulation of any of Embodiments 1 to 4, further comprising a soil penetration agent. Embodiment 6 is a composition of any of Embodiments 1 to 5, further comprising a fragrance.

[0355] Embodiment 7 is Equation I:

[0356] [ka]

[0357] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; Optionally, a thickener; and water It is a hair shampoo formulation containing [the specified ingredient].

[0358] Embodiment 8 is the formulation of Embodiment 7, further comprising a foaming agent. Embodiment 9 is a formulation of either Embodiment 7 or Embodiment 8, further comprising a pH stabilizer. Embodiment 10 is a formulation of any of Embodiments 7 to 9, further comprising a soil penetration agent.

[0359] Embodiment 11 is a composition of any of Embodiments 7 to 10, further comprising a fragrance. Appearance 12 is Equation I

[0360] [ka]

[0361] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; Selectively fatty components; and water It is a hair conditioner formulation containing [ingredient name].

[0362] Embodiment 13 is the formulation of Embodiment 12, further comprising an emulsifier. Embodiment 14 is a formulation of either Embodiment 12 or Embodiment 13, further comprising at least one thickening agent.

[0363] Embodiment 15 is a formulation of any of Embodiments 12 to 14, further comprising a foaming agent. Embodiment 16 is a formulation of any of Embodiments 12 to 15, further comprising at least one type of clay.

[0364] Embodiment 17 is a composition of any of Embodiments 12 to 16, further comprising a fragrance. Embodiment 18 is Equation I

[0365] [ka]

[0366] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; At least one solvent of any choice; and water It is a cleanser formulation containing [ingredient name].

[0367] Embodiment 19 is the formulation of Embodiment 18, further comprising at least one water-soluble polymer. Embodiment 20 is a formulation of either Embodiment 18 or Embodiment 19, further comprising at least one water-soluble solvent.

[0368] Embodiment 21 is a formulation of any of Embodiments 18 to 20, further comprising at least one fatty component. Embodiment 22 is a formulation of any of Embodiments 18 to 21, further comprising at least one type of conditioner.

[0369] Embodiment 23 is a formulation according to any one of claims 18 to 22, further comprising a hydrophobic modifier. Embodiment 24 is Equation I

[0370] [ka]

[0371] [In the formula, R 1 and R 2The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; Optionally, a wetting agent; and water It is a cleanser formulation containing [ingredient name].

[0372] Embodiment 25 is the formulation of Embodiment 24, further comprising at least one water-soluble polymer. Embodiment 26 is a formulation of either Embodiment 24 or Embodiment 25, further comprising at least one water-soluble solvent.

[0373] Embodiment 27 is a formulation of any of Embodiments 24 to 26, further comprising at least one fatty component. Embodiment 28 is a formulation of any of Embodiments 24 to 27, further comprising at least one type of conditioner.

[0374] Embodiment 29 is a formulation of any of Embodiments 24 to 28, further comprising a hydrophobic modifier. Embodiment 30 is a formulation of any of Embodiments 24 to 29, further comprising at least one solvent.

[0375] Embodiment 31 is Equation I

[0376] [ka]

[0377] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; At least one polymer, optionally selected; and water It is a mascara formulation that includes [ingredient name].

[0378] Embodiment 32 is the formulation of Embodiment 31, further comprising at least one fatty component. Embodiment 33 is a formulation of either Embodiment 31 or Embodiment 32, further comprising at least one rheological modifier.

[0379] Embodiment 34 is a formulation of any of Embodiments 31 to 33, further comprising at least one emulsifier. Embodiment 35 is a formulation of any of Embodiments 31 to 34, further comprising a pigment.

[0380] Embodiment 36 is Equation I

[0381] [ka]

[0382] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. At least one surfactant; Optional fluoride ion source; and water It is a toothpaste formulation containing [the specified ingredient].

[0383] Embodiment 37 is the formulation of Embodiment 26, further comprising at least one basic amino acid. Embodiment 38 is a formulation of either Embodiment 36 or Embodiment 37, further comprising calcium carbonate.

[0384] Embodiment 39 is a composition of any of Embodiments 36 to 38, further comprising a flavoring agent. Embodiment 40 is the use of a compound of formula I as a surfactant in a shampoo formulation comprising at least one surfactant of formula I, optionally a foaming agent, and water,

[0385] [ka]

[0386] In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the linker, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0387] Embodiment 41 is a use of Embodiment 40, further comprising a foaming agent. Embodiment 42 is a use of Embodiment 40 or Embodiment 41, further comprising at least one type of adhesive.

[0388] Embodiment 43 is the use of Embodiments 40-42, further comprising a pH stabilizer. Embodiment 44 is the use of Embodiments 40-43, further comprising a soil penetration agent. Embodiment 45 is a use of Embodiments 40-44, further comprising a fragrance.

[0389] Embodiment 46 is the use of a compound of formula I as a surfactant in a shampoo formulation comprising at least one surfactant of formula I, and optionally a thickener; and water,

[0390] [ka]

[0391] In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0392] Embodiment 47 is the use of Embodiment 46, which further comprises a foaming agent. Embodiment 48 is the use of Embodiment 46 or Embodiment 47, further comprising a pH stabilizer. Embodiment 49 is the use of Embodiments 46-48, further comprising a soil penetration agent.

[0393] Embodiment 50 is the use of 46-49, which further includes a fragrance. Embodiment 51 is the use of a compound of formula I as a surfactant in a shampoo formulation comprising at least one surfactant of formula I, and optionally a foaming agent; and water,

[0394] [ka]

[0395] In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0396] Embodiment 52 is the use of Embodiment 51, further comprising an emulsifier. Embodiment 53 is the use of Embodiment 51 or Embodiment 52, further comprising at least one thickening agent.

[0397] Embodiment 54 is the use of any of Embodiments 51 to 53, further comprising a foaming agent. Embodiment 55 is the use of any of embodiments 51 to 54, further comprising at least one type of clay.

[0398] Embodiment 56 is the use of any of Embodiments 51 to 55, further comprising a fragrance. Embodiment 57 is the use of a compound of formula I as a surfactant in a cleanser formulation comprising at least one surfactant of formula I, and optionally at least one solvent; and water,

[0399] [ka]

[0400] In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0401] Embodiment 58 is an application of Embodiment 57, further comprising at least one water-soluble polymer. Embodiment 59 is the use of Embodiment 57 or Embodiment 58, further comprising at least one water-soluble solvent.

[0402] Embodiment 60 is a use of any of Embodiments 57 to 59, further comprising at least one fatty component. Embodiment 61 is a use of any of embodiments 57 to 60, further comprising at least one type of conditioner.

[0403] Embodiment 62 is the use of any of Embodiments 57 to 61, further comprising a hydrophobic modifier. Embodiment 63 is the use of a compound of formula I as a surfactant in a cleanser formulation comprising at least one surfactant of formula I, and optionally a wetting agent; and water,

[0404] [ka]

[0405] In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0406] Embodiment 64 is the formulation of Embodiment 63, further comprising at least one water-soluble polymer. Embodiment 65 is the use of either Embodiment 63 or Embodiment 64, further comprising at least one water-soluble solvent.

[0407] Embodiment 66 is the use of any of embodiments 63 to 65, further comprising at least one fatty component. Embodiment 67 is a use of any of embodiments 63 to 66, further comprising at least one type of conditioner.

[0408] Embodiment 68 is the use of any of Embodiments 63 to 67, further comprising a hydrophobic modifier. Embodiment 69 is the use of any of embodiments 63 to 68, further comprising at least one solvent.

[0409] Embodiment 70 is the use of a compound of formula I as a surfactant in a mascara formulation comprising at least one surfactant of formula I, and optionally at least one polymer; and water,

[0410] [ka]

[0411] In the formula, R 1 and R 2The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0412] Embodiment 71 is a use of Embodiment 70, further comprising at least one fatty component. Embodiment 72 is the use of either Embodiment 70 or Embodiment 71, further comprising at least one rheological modifier.

[0413] Embodiment 73 is a use of Embodiments 70 to 72, further comprising at least one emulsifier. Embodiment 74 is the use of Embodiments 70-73, further comprising a pigment. Embodiment 75 describes the use of a compound of formula I as a surfactant in a toothpaste formulation comprising at least one surfactant of formula I, and optionally a fluorine source; and water,

[0414] [ka]

[0415] In the formula, R 1 and R2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is a substance selected from the group consisting of chloride, bromide, and iodide.

[0416] Embodiment 76 is an application of Embodiment 75, further comprising at least one basic amino acid. Embodiment 77 is a shampoo, conditioner, mascara, or toothpaste formulation disclosed in any one of Embodiments 1 to 39.

[0417] Embodiment 78 is use as a shampoo, conditioner, mascara or toothpaste formulation containing at least one surfactant of the compound of formula (I),

[0418] [ka]

[0419] In the formula, R 1 and R 2The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyl groups, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, alkyl phosphonate, C3-C8 carboxylic acid, C1-C 10 Alkylbenzoic acid, and C1-C bonded to the second molecule of formula I 12 Selected from the group consisting of linkers, the second molecule of formula I is either the same as or different from the first molecule of formula I; n is an integer between 1 and 12; X is selected from the group consisting of chlorides, bromides, and iodides.

[0420] Embodiment 79 is Equation I

[0421] [ka]

[0422] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyls, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10A method for preparing one of the formulations of embodiments 1 to 11, comprising the steps of synthesizing a compound of [selected from the group consisting of alkylbenzoic acid and a C1-C6 linker bonded to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chloride, bromide, and iodide], comprising the steps of: opening a lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; alkylating the N-terminal group by a first alkylation to obtain a tertiary amine; reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; alkylating the N-terminal group by a second alkylation to obtain a quaternary amine of formula I; and adding a foaming agent or thickener; and water. A method that includes this.

[0423] Embodiment 80 is Equation I

[0424] [ka]

[0425] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyls, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10A method for preparing any one of the formulations of embodiments 12 to 17, comprising the steps of synthesizing a compound of [alkylbenzoic acid and a C1-C6 linker bonded to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chloride, bromide, and iodide], comprising the steps of: opening a lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; and alkylating the N-terminal group by a first alkylation to obtain a tertiary amine; The process involves: reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; and alkylating the N-terminal group by a second alkylation to obtain a quaternary amine of formula I. The steps include adding fatty components and water. This method includes [something].

[0426] Embodiment 81 is Equation I

[0427] [ka]

[0428] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyls, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10A method for preparing any one of the formulations of embodiments 18 to 30, comprising the steps of synthesizing a compound of [selected from the group consisting of alkylbenzoic acid and a C1-C6 linker bonded to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chloride, bromide, and iodide], comprising the steps of: opening a lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; and alkylating the N-terminal group by a first alkylation to obtain a tertiary amine; The process involves: reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; and alkylating the N-terminal group by a second alkylation to obtain a quaternary amine of formula I. A step of adding a wetting agent or at least one solvent; and water. This method includes [something].

[0429] Embodiment 82 is Equation I

[0430] [ka]

[0431] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyls, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10A method for preparing any one of the formulations of embodiments 31 to 35, comprising the steps of synthesizing a compound of [selected from the group consisting of alkylbenzoic acid and a C1-C6 linker bonded to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chloride, bromide, and iodide], comprising the steps of: opening a lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; alkylating the N-terminal group by a first alkylation to obtain a tertiary amine; reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; and alkylating the N-terminal group by a second alkylation to obtain a quaternary amine of formula I, The steps include adding at least one polymer and water. This method includes [something].

[0432] Embodiment 83 is Equation I

[0433] [ka]

[0434] [In the formula, R 1 and R 2 The groups are the same or different and comprise at least one group selected from the group consisting of C1-C6 alkyls, optionally comprising one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R 3 Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C3-C8 carboxylic acid, C1-C 10A method for preparing any one of the formulations of embodiments 36 to 39, comprising the steps of synthesizing a compound of [selected from the group consisting of alkylbenzoic acid and a C1-C6 linker bonded to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; and X is selected from the group consisting of chloride, bromide and iodide], comprising the steps of: opening a lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; alkylating the N-terminal group by a first alkylation to obtain a tertiary amine; reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; and alkylating the N-terminal group by a second alkylation to obtain a quaternary amine of formula I, A fluoride ion source; and the step of adding water. This method includes [something].

[0435] Embodiment 84 is any of the methods according to Embodiments 79 to 83, wherein the lactam is caprolactam. Embodiment 85 is any of the methods according to Embodiments 79 to 84, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

[0436] Embodiment 86 is one of the methods of Embodiments 79 to 85, wherein in the second alkylation step, the N-terminal group is alkylated with an alkylating agent selected from the group consisting of benzyl bromide, ethyl bromo, 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. Formula I: 【Chemistry 1】 [In the formula, R １ and R ２ They are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally C １ ~C ６ The alkyl group may contain one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ -C ８ carboxylic acid, C １ -C １０ alkylbenzoic acid, and C １ -C ６ linker attached to the second molecule of formula I, and the second molecule is the same or different; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. at least one surfactant, At least one of a foaming agent and a thickener; and water A shampoo formulation containing the following ingredients.

2. The formulation according to claim 1, further comprising at least one of a foaming agent, a pH stabilizer, a soil penetration agent, or a fragrance.

3. Equation I 【Chemistry 2】 [In the formula, R １ and R ２ They are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally C １ ~C ６ The alkyl group may contain one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. at least one surfactant, Fatty components; and water A hair conditioner formulation containing [ingredient].

4. The formulation according to claim 3, further comprising at least one of an emulsifier, a thickener, a foaming agent, clay, or a fragrance.

5. Equation I 【Transformation 3】 [In the formula, R １ and R ２ They are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally C １ ~C ６ The alkyl group may contain one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. at least one surfactant, At least one solvent and a wetting agent; and water A cleanser formulation containing the following ingredients.

6. The formulation according to claim 5, further comprising at least one water-soluble polymer, at least one fatty component, a conditioner, or a hydrophobic modifier.

7. Equation I 【Chemistry 4】 [In the formula, R １ and R ２ They are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally C １ ~C ６ The alkyl group may contain one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer between 1 and 12; X is selected from the group consisting of chloride, bromide, and iodide. at least one surfactant, Fluoride ion source; and water Toothpaste formulation containing [ingredient].

8. The formulation according to claim 7, further comprising at least one of calcium carbonate or a flavoring agent.

9. Formula I: 【Transformation 5】 [In the formula, R １ and R ２ They are the same or different, C １ ~C ６ It comprises at least one group selected from the group consisting of alkyl groups, and optionally C １ ~C ６ The alkyl group may contain one or more oxygen, nitrogen, or sulfur atoms, or a group containing at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amide, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R ３ Alkenyl, alkynyl, ester, alcohol, arylalkyl, alkoxyalkyl ether, alkyl phosphate, C ３ ~C ８ Carboxylic acid, C １ ~C １０ Alkylbenzoic acid, and C bonded to the second molecule of formula I １ ~C ６ Selected from the group consisting of linkers, the second molecule is the same or different; n is an integer from 1 to 12; X is selected from the group consisting of chlorides, bromides, and iodides. A method for preparing a formulation according to any one of claims 1 to 8, comprising the step of synthesizing a compound, The steps include: opening the lactam ring to obtain an amino acid having an N-terminal group and a C-terminal group; The first step is to alkylate the N-terminal group by a first alkylation to obtain a tertiary amine; The steps include: reacting the C-terminal group with 3-aminopropyltris(trimethylsiloxy)silane by coupling to obtain a siloxane derivative; The second step involves alkylating the N-terminal group to obtain a quaternary amine of formula I; The steps include adding a foaming agent, a thickener; at least one further component selected from a fatty component, a fluoride ion source, a solvent, or a wetting agent; and optionally adding water. A method that includes this.

10. The method according to claim 10, wherein the lactam is caprolactam.

11. The method according to claim 10, wherein in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.

12. Use of the formulation according to claim 1 or 2 as a shampoo.

13. Use of the formulation according to claim 3 or 4 as a conditioner.

14. Use of the formulation according to claim 5 or 6 as a cleanser.

15. Use of the formulation according to claim 7 or 8 as a toothpaste.

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