KR-20260064691-A - Amino acid siloxane derivatives as surfactants in personal care and cosmetic products

KR20260064691AKR 20260064691 AKR20260064691 AKR 20260064691AKR-20260064691-A

Abstract

Personal care products such as shampoo, conditioner, hair dye, hair removal product, cleanser, cosmetic, mascara, and toothpaste may be formulated to include one or more surfactants from one or more classes of surfactants, such as siloxane derivatives of amino acids having surface-active properties.

Inventors

아시르바탐, 에드워드
아난타파드마나반, 카브세리
쿠마리, 하르시타
미타팔리, 라마나
파니그라히, 수치트라

Assignees

어드밴식스 레진즈 앤드 케미컬즈 엘엘씨

Dates

Publication Date: 20260507
Application Date: 20240807
Priority Date: 20240805

Claims (15)

Shampoo formulations comprising the following: At least one surfactant of chemical formula I: Herein, R1 and R2 are the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxyalkyl ether, alkyl phosphate, C3 - C8 carboxylic acid, C1 - C10 alkyl benzoic acid, and a C1 - C6 linker attached to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; X is selected from the group consisting of chloride, bromide, and iodide; At least one of a foaming agent and a thickening agent; and water.
A formulation according to claim 1, further comprising at least one of a foam booster, a pH stabilizer, a contamination penetration agent, or a fragrance.
A hair conditioner formulation comprising the following: At least one surfactant of chemical formula I: Herein, R1 and R2 are the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxyalkyl ether, alkyl phosphate, C3 - C8 carboxylic acid, C1 - C10 alkyl benzoic acid, and a C1 - C6 linker attached to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; X is selected from the group consisting of chloride, bromide, and iodide; Fat components; and water.
A formulation according to paragraph 3, further comprising at least one of an emulsifier, a thickener, a foaming agent, clay, or a fragrance.
A preparation for a cleaning agent comprising the following: At least one surfactant of chemical formula I: Herein, R1 and R2 are the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxyalkyl ether, alkyl phosphate, C3 - C8 carboxylic acid, C1 - C10 alkyl benzoic acid, and a C1 - C6 linker attached to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; X is selected from the group consisting of chloride, bromide, and iodide; At least one of a solvent and a humectant; and water.
A formulation according to claim 5, further comprising at least one of a water-soluble polymer, at least one fatty component, a conditioner, or a hydrophobic modifier.
Toothpaste formulations including the following: At least one surfactant of chemical formula I: Herein, R1 and R2 are the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxyalkyl ether, alkyl phosphate, C3 - C8 carboxylic acid, C1 - C10 alkyl benzoic acid, and a C1 - C6 linker attached to a second molecule of formula I, wherein the second molecule is the same or different; n is an integer from 1 to 12; X is selected from the group consisting of chloride, bromide, and iodide; Fluoride ion source; and water.
A preparation according to claim 7, further comprising at least one of calcium carbonate or a flavoring agent.
A method for manufacturing a preparation of any one of claims 1 to 8, comprising the following: Step for synthesizing the compound of chemical formula I: Herein, R1 and R2 are the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate; R3 is selected from the group consisting of alkenyl, alkynyl, ester, alcohol, aryl alkyl, alkoxyalkyl ether, alkyl phosphate, C3 - C8 carboxylic acid, C1 - C10 alkyl benzoic acid, and a C1 - C6 linker attached to the second molecule of Formula I, wherein 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, and the method comprises the following: A ring-opening step of opening a lactam ring to provide an amino acid having an N-terminus and a C-terminus, A first alkylation step that alkylates the N-terminus to provide a tertiary amine, A coupling step of reacting the C-terminus with 3-aminopropyltris(trimethylsiloxy)silane to provide a siloxane derivative, and A second alkylation step of alkylating the N-terminus to provide a quaternary amine of formula I; and At least one additional component selected from a foaming agent, a thickener, a fatty component, a fluoride ion source, a solvent, or a humectant; and optionally a step of adding water.
In paragraph 10, the method in which the lactam is caprolactam.
In claim 10, the method in which, in the first alkylation step, the tertiary amine is 6-(dimethylamino)hexanoic acid.
Use of the formulation of claim 1 or 2 as a shampoo.
Use of the formulation of paragraph 3 or 4 as a conditioner.
Use of the formulation of paragraph 5 or 6 as a cleaning agent.
Use of the formulation of paragraph 7 or 8 as toothpaste.

Description

Amino acid siloxane derivatives as surfactants in personal care and cosmetic products Cross-reference regarding related applications The present application claims priority to U.S. application number 18/795,174 filed on August 5, 2024, and to U.S. provisional patent application serial number 63/531,194 filed on August 7, 2023, the entire disclosures of which are incorporated by reference. field The present disclosure relates to surfactants for use in personal care and cosmetic products. Such surfactants may include siloxane derivatives of amino acids having surface-active properties and methods for synthesizing the same. Surfactants (molecules with surface-active properties) are widely used in commercial applications in formulations ranging from detergents to hair care products and cosmetics. Compounds with surface-active properties are used particularly as 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, etc.), surfactants or mixtures of surfactants can serve as one of the most important ingredients, as they provide most of the cleansing properties of the composition. Surfactants can be uncharged, zwitterionic, cationic, or anionic. In principle, any class of surfactants (e.g., cationic, anionic, nonionic, amphoteric) is suitable for cleaning or washing applications, but in practice, many personal care detergents and household cleaning products are formulated with a combination of two or more surfactants from two or more classes of surfactants. Typically, these surfactants are amphiphilic molecules possessing 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 a liquid and a gas, or between a liquid and a solid. In systems containing a relatively polar component and a relatively non-polar component, the hydrophobic tail preferentially interacts with the relatively non-polar component(s), while the hydrophilic head preferentially interacts with the relatively polar component(s). In the case of an interface between water and oil, the hydrophilic head group preferentially faces water, while the hydrophobic tail preferentially faces oil. When added to a water-gas interface, the hydrophilic head group preferentially faces water, while the hydrophobic tail preferentially faces gas. The presence of a surfactant can disrupt at least some of the intermolecular interactions between water molecules, thereby replacing at least some of these interactions with generally weaker interactions between some water molecules and the surfactant. This results in reduced surface tension, which can also act to stabilize or otherwise alter the interface of materials of different physical forms. At sufficiently high concentrations, surfactants can form aggregates, which act to limit the exposure of the hydrophobic tails to polar solvents. One such aggregate is a micelle. In a typical micelle, molecules are arranged in a sphere, with the hydrophobic tails of the surfactant(s) preferentially located inside the sphere and the hydrophilic heads preferentially located outside the micelle, where the heads preferentially interact with the more polar solvent. The concentration at which a compound forms micelles, as well as the effect of the compound on surface tension, can play a role in defining the characteristics of the surfactant. The present disclosure provides personal care products, such as shampoos, conditioners, hair dyes, depilatory products, cleansers, cosmetics, mascaras, dental prosthetic cleaners, and toothpastes. These products may be formulated to include one or more surfactants from one or more classes of surfactants disclosed herein. The present disclosure provides a surfactant for personal care products in the form of a siloxane derivative of an amino acid having surface-active properties. The amino acid may be a naturally occurring or synthetic amino acid, or may be obtained through the ring-opening reaction of a molecule such as a lactam, e.g., caprolactam. The amino acid may be functionalized with different types of siloxane groups to form a compound having surface-active properties. Characteristically, such a compound may have the ability to reduce a low critical micelle concentration (CMC) and/or the surface tension of a liquid. The present disclosure provides a hair shampoo formulation comprising the following: One or more surfactant molecules having the structure(s) of Chemical Formula I or II (wherein R1 and R2 may be the same or different and comprise at least one group selected from the group consisting of C1 - C6 alkyls, optionally the C1 - C6 alkyl may comprise one or more of oxygen, nitrogen, or sulfur atoms, or a group comprising at least one of these atoms, and the alkyl chain may optionally be substituted with one or more substit