Phosphorylcholine copolymer containing active groups, preparation method therefor, and use thereof in modifying cosmetic raw materials

Abstract

The present invention provides a phosphorylcholine copolymer containing active groups. The present invention further provides a preparation method for a phosphorylcholine copolymer containing active groups. The present invention further provides a method for modifying functional raw materials by using a phosphorylcholine copolymer containing active groups. The present invention further provides the above phosphorylcholine copolymer containing active groups, or a use of a functional raw material composition modified by the phosphorylcholine copolymer containing active groups in cosmetics. The phosphorylcholine copolymer containing active groups, the preparation method therefor, and the use thereof in modifying cosmetic raw materials provided by the present invention introduce active groups into a phosphorylcholine polymer, thereby endowing the same with bioactivity, and modifying cosmetic functional raw materials therewith. The process is mild and simple, efficient and safe, and can significantly enhance the solubility, activity stability, color stability, and transdermal absorption efficiency of functional raw materials, making said materials easier to apply in cosmetics.

Description

A phosphorylcholine copolymer containing active groups, its preparation method, and its application in modifying cosmetic raw materials. Technical Field

[0001] This invention belongs to the technical field of functional polymer materials, and relates to a phosphorylcholine copolymer containing active groups, its preparation method, and its application in modifying cosmetic raw materials. Specifically, it relates to a phosphorylcholine copolymer containing active groups such as hydroxyl and carboxyl groups, its preparation method, and its use as a polymer material in daily chemical products to modify cosmetic raw materials. Background Technology

[0002] Phosphorylcholine polymers are a class of polymeric materials with structures similar to phospholipids. They typically contain amphoteric and anodic end groups and nonpolar alkane chains; the amphoteric end groups are hydrophilic, while the alkane chains are hydrophobic. This structure is very similar to that of biological membranes, therefore, the blood compatibility of phosphorylcholine polymers is very close to that of biological membranes. In the field of biomaterials, research on their properties and synthesis methods is attracting increasing attention. Studies have shown that phosphorylcholine polymers can modify the surface of biomaterials to mimic the extracellular layer structure, and are widely used in medicine, cosmetics, and other fields.

[0003] Patent CN111467571A, "A Multifunctional Cardiovascular Coating Material with Superhydrophilicity and Its Preparation Method," describes the preparation of a superhydrophilic MPC multi-component copolymer by free radical polymerization of 2-methacryloyloxyethyl phosphocholine, vinyltrimethoxysilane, 2-acrylamido-2-methylpropanesulfonic acid, and maleimide-tris(ethylene glycol)-propionic acid under the action of an initiator. The resulting MPC copolymer is then mixed uniformly with chitosan quaternary ammonium salt to obtain a material with superhydrophilicity and good biocompatibility. However, excessive hydrophilicity can significantly limit its practical application.

[0004] Patent EP1095665A1, "Band-Aid Formulation, Band-Aid Material and Wound Healing Method," describes an MPC binary copolymer obtained by polymerizing 2-methacryloyloxyethyl phosphorylcholine, butyl methacrylate, etc. This results in a wound dressing that is effective in cleaning wound sites and removing necrotic tissue, and has excellent hydrophilicity and biocompatibility. It also promotes cell repair. However, this binary polymer requires waterproofing treatment during use to prevent loss of its properties.

[0005] Meanwhile, the application scenarios of active ingredients are often limited by their inherent properties. For example, sodium hyaluronate is a polysaccharide with strong lubricating, film-forming, and moisturizing properties. Its molecular morphology and physicochemical properties vary with molecular weight. The molecular structure of sodium hyaluronate contains many hydrogen bonds and is spatially rigid in a helical column shape. It contains a large number of hydroxyl groups on the inside, which can bind a large number of water molecules. These water molecules are very firmly bound within the column, exhibiting good water absorption and safety. Large-molecule sodium hyaluronate aqueous solutions are highly viscous. Patent CN202310540742.2 mentions using acids and bases to change the viscosity of sodium hyaluronate; however, acids and bases affect the unique properties of sodium hyaluronate and pose challenges for its application in cosmetic formulations.

[0006] Phytosphingosine is a precursor to ceramides and also a component of skin lipids. It possesses natural barrier-repairing properties and exhibits strong antimicrobial activity, effectively reducing inflammation and redness. As a skin lipid component, phytosphingosine offers multiple benefits to the skin, enhancing the effectiveness of high-end anti-aging and repair products. However, its poor water solubility makes it challenging to use in cosmetics.

[0007] Patent CN105919824A, "Oil-based Cosmetics Containing EGCG and Their Preparation Method and Application," discloses a method of first dissolving EGCG in an alcohol solution and then further dispersing it in oil. While this method improves the stability of EGCG, the alcohol used in the method is ethanol, which may irritate the skin. Patent CN117100629A achieves transdermal enhancement of active ingredients by preparing terpenoids of active ingredients such as resveratrol and glycyrrhizin. However, terpenoids have high requirements for the operation process, and terpenoids often have poor stability. The patent does not examine the stability. Patent CN116725896A, "A Lactoferrin Collagen Anti-wrinkle Supramolecular Microcapsule and Its Preparation Method," encapsulates collagen peptides in the form of supramolecular microcapsules, improving the efficacy and transdermal penetration of collagen peptides. However, the operation process uses high-pressure homogenization equipment, and the high temperature and pressure generated during the process may affect the protein structure, leading to denaturation and inactivation of collagen. Summary of the Invention

[0008] In view of the shortcomings of the prior art described above, the purpose of this invention is to provide a phosphorylcholine copolymer containing active groups, a method for preparing the copolymer, and its application in modifying cosmetic raw materials. The obtained copolymer polymer can modify cosmetic functional raw materials to improve their performance in cosmetics, thereby helping the cosmetic industry to better apply these active raw materials and maximize their efficacy.

[0009] To achieve the above and other related objectives, the first aspect of the present invention provides a phosphorylcholine copolymer containing active groups, the chemical structure of which is shown in formula (I):

[0010] In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2) n NH2, where 0 ≤ n ≤ 8.

[0011] The second aspect of the present invention provides a method for preparing a phosphorylcholine copolymer containing active groups, comprising: adding 2-methacryloyloxyethyl phosphorylcholine (MPC, III), fatty acid methacrylate (IV), and methacrylate containing active groups (V) to an initiator and a solvent for polymerization reaction, and then post-treating the obtained polymerization solution to obtain a phosphorylcholine copolymer (I) containing active groups.

[0012] The process route is as follows:

[0013] In equation (Ⅳ), 0 ≤ m ≤ 25;

[0014] In formula (V), R is selected from H, hydroxyl (-OH), carboxyl (-COOH), amino (-NH2), or epoxy group;

[0015] In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2) n NH2, where 0 ≤ n ≤ 8.

[0016] A third aspect of the present invention provides the above-mentioned phosphorylcholine copolymer containing active groups, which is prepared by the above method.

[0017] A fourth aspect of the present invention provides a method for modifying an efficacy raw material with a phosphorylcholine copolymer containing an active group, comprising: mixing and reacting the efficacy raw material with the aforementioned phosphorylcholine copolymer containing an active group and a solvent to provide a desired efficacy raw material composition modified with a phosphorylcholine copolymer containing an active group.

[0018] The fifth aspect of the present invention provides a functional raw material composition modified with a phosphorylcholine copolymer containing an active group, which is prepared by the above method.

[0019] The sixth aspect of the present invention provides the use of the above-mentioned phosphorylcholine copolymer containing active groups, or the above-mentioned phosphorylcholine copolymer modified with active groups, in cosmetics.

[0020] As described above, the phosphorylcholine copolymer containing active groups, its preparation method, and its application in modifying cosmetic raw materials provided by the present invention have the following beneficial effects compared with the prior art:

[0021] (1) This invention provides a phosphorylcholine copolymer containing active groups, its preparation method, and its application in modifying cosmetic raw materials. Using biocompatible 2-methacryloyloxyethyl phosphoric acid choline (MPC), methacrylate fatty acid ester monomers, and methacrylates containing active groups such as hydroxyl, carboxyl, amino, and epoxy groups as monomers, binary or ternary copolymer polymers are prepared by free radical solution copolymerization as phosphorylcholine copolymers containing active groups. This phosphorylcholine copolymer introduces active groups such as hydroxyl, carboxyl, amino, and epoxy groups into the phosphorylcholine polymer, giving it biological activity.

[0022] (2) The present invention provides a phosphorylcholine copolymer containing active groups, its preparation method and its application in modifying cosmetic raw materials. The prepared phosphorylcholine copolymer containing active groups can modify cosmetic functional raw materials. The process is mild, simple, efficient and safe.

[0023] (3) The present invention provides a phosphorylcholine copolymer containing active groups, its preparation method and its application in modifying cosmetic raw materials. The prepared phosphorylcholine copolymer containing active groups can significantly enhance the solubility, activity stability, color stability and transdermal absorption efficiency of the active raw materials through supramolecular forces between the phosphorylcholine copolymer and the active molecules of the active raw materials, such as hydrogen bonds, intermolecular forces and encapsulation. At the same time, the efficacy of the active materials is equal to or enhanced, making the active materials more stable, slowing down discoloration and inactivation, increasing transdermal efficiency and enhancing efficacy.

[0024] (4) The present invention provides a phosphorylcholine copolymer containing active groups, its preparation method and application of modified cosmetic raw materials, so that the phosphorylcholine copolymer containing active groups can modify cosmetic functional raw materials to improve their application performance in cosmetics, thereby solving the application difficulties of the corresponding functional raw materials and making them easier to use in cosmetics, so as to help the cosmetic industry better apply these active raw materials and maximize their efficacy. Attached Figure Description

[0025] Figure 1 shows the 1H NMR spectrum of a carboxyl-containing phosphorylcholine ternary polymer according to Example 1 of the present invention.

[0026] Figure 2 shows the GPC diagram of a carboxyl-containing phosphorylcholine ternary polymer in Example 1 of the present invention.

[0027] Figure 3 shows the infrared spectrum of a carboxyl-containing phosphorylcholine ternary polymer according to Example 1 of the present invention.

[0028] Figure 4 shows the 1H NMR spectrum of a phosphorylcholine binary polymer containing epoxy groups in Example 2 of the present invention.

[0029] Figure 5 shows the GPC diagram of a phosphorylcholine binary polymer containing epoxy groups in Example 2 of the present invention.

[0030] Figure 6 shows the infrared spectrum of a phosphorylcholine binary polymer containing epoxy groups in Example 2 of the present invention.

[0031] Figure 7 shows a comparison of the flowability of the samples from Example 6 and Comparative Example 1 of the present invention, wherein the upper bottle contains the sample of Example 6 and the lower bottle contains the sample of Comparative Example 1.

[0032] Figure 8 shows the infrared spectrum of sodium hyaluronate modified with phosphorylcholine polymer in this invention.

[0033] Figure 9 shows a comparison of the appearance of the samples of Example 7 and Comparative Example 2 of the present invention, wherein the sample of Example 7 is in the left bottle and the sample of Comparative Example 2 is in the right bottle.

[0034] Figure 10 shows a comparison of the difference in water content of the stratum corneum of the skin in this invention.

[0035] Figure 11 shows a comparison of cell survival rates in this invention.

[0036] Figure 12 shows the comparison of high-temperature color stability of samples before and after modification in this invention (Figures 12a, 12b, 12c, 12d, and 12e). Figure 12a shows the high-temperature color stability of samples before and after modification at day 0; Figure 12b shows the high-temperature color stability of samples before and after modification at day 7; Figure 12c shows the high-temperature color stability of samples before and after modification at day 15; Figure 12d shows the high-temperature color stability of samples before and after modification at day 30; and Figure 12e shows the high-temperature color stability of samples before and after modification at day 60. In Figures 12a, 12b, 12c, 12d, and 12e, the left bottle contains the sample before modification, and the right bottle contains the sample after modification.

[0037] Figure 13 shows a comparison of the expression of skin repair-related groups in this invention. Detailed Implementation

[0038] The inventors of this application have developed a phosphorylcholine copolymer containing active groups, introducing active groups such as hydroxyl, carboxyl, amino, and epoxy groups into the phosphorylcholine polymer to give it biological activity. Furthermore, a method for preparing the phosphorylcholine copolymer containing active groups is provided, using biocompatible 2-methacryloyloxyethyl phosphorocholine (MPC) monomer, methacrylate fatty acid ester monomers, and methacrylates containing active groups such as hydroxyl, carboxyl, amino, and epoxy groups as monomers, and preparing binary or ternary copolymer polymers via free radical solution copolymerization. The process is mild, simple, efficient, and safe. A method for modifying functional raw materials with phosphorylcholine copolymers containing active groups is also provided, which can modify various functional raw materials. Furthermore, a composition of functional raw materials modified with phosphorylcholine copolymers containing active groups and its application in cosmetics are provided, significantly enhancing the solubility, activity stability, color stability, and transdermal absorption efficiency of functional raw materials, while maintaining or enhancing the efficacy of the active ingredients. Thus, this invention is completed, and is described in detail below.

[0039] Terminology Definition

[0040] Unless otherwise stated, the following words, phrases and symbols used in this specification generally have the meanings described below.

[0041] Generally, the nomenclature used herein (e.g., IUPAC nomenclature) and the laboratory procedures described below (including those for cell culture, organic chemistry, analytical chemistry, and pharmacology) are those well-known and commonly used in the art. Unless otherwise defined, all scientific and technical terms used herein in conjunction with the disclosure described herein have the same meaning as commonly understood by one of ordinary skill in the art. Additionally, in the claims and / or description, the term “a” or “an” used in conjunction with the term “comprising” or a noun may mean “one,” but also is consistent with the meanings of “one or more,” “at least one,” and “one or more.” Similarly, the term “another” or “other” may mean at least a second or more.

[0042] It should be understood that whenever this document uses the terms “comprising” or “including” to describe a particular aspect, other similar aspects described by “consisting of” and / or “substantially consisting of” are also provided.

[0043] The first aspect of the present invention provides a phosphorylcholine copolymer containing active groups, the chemical structure of which is shown in formula (I):

[0044] In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2)n NH2, where 0 ≤ n ≤ 8.

[0045] In reaction (I), x, y, and z represent the number of repeating units, x is a positive integer greater than 0, z is a positive integer greater than 0, and y is an integer greater than or equal to 0.

[0046] For example, x can be 500-1000. In some specific embodiments, x can be 500-600, 500-700, 500-900, or 900-1000.

[0047] For example, y can be 0-300. In some specific embodiments, y can be 0-100, 0-200, or 0-300.

[0048] For example, z can be 50-500. In some specific embodiments, z can be 50-100, 100-200, or 200-500.

[0049] In reaction formula (I), x:y:z is 5~10:0~3:0.5~5. In some specific embodiments, x:y:z can be 5~8:0~3:0.5~5, 8~10:0~3:0.5~5, 5~10:0~1:0.5~5, 5~10:2~3:0.5~5, 5~10:0~3:0.5~2, or 5~10:0~3:2~5.

[0050] In reaction formula (I), m is a positive integer greater than or equal to 0 and less than or equal to 25. For example, 1≤m≤5, 5≤m≤10, 2≤m≤9, 3≤m≤8, 4≤m≤7, 15≤m≤25. In some specific embodiments, m can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25.

[0051] In reaction (I), n is an integer greater than or equal to 0 and less than or equal to 8. For example, 0≤n≤4, 4≤n≤8, 1≤n≤7, 2≤n≤6, 3≤n≤5, 4≤n≤6, 3≤n≤7, 2≤n≤8. In some specific embodiments, n can be 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0052] In reaction formula (I), when y is not equal to 0, the chemical structure of the copolymer is a ternary copolymer as shown in formula (I).

[0053] In reaction formula (I), when y equals 0, the chemical structure of the copolymer is shown in formula (II), which is a binary copolymer;

[0054] In reaction (II), x and y represent the number of repeating units, respectively. x is a positive integer greater than 0, and y is a positive integer greater than 0.

[0055] For example, x can be 500-1000. In some specific embodiments, x can be 500-600, 500-700, 500-900, or 900-1000.

[0056] For example, y can be 50-500. In some specific embodiments, y can be 50-100, 100-200, or 200-500.

[0057] The second aspect of the present invention provides a method for preparing a phosphorylcholine copolymer containing active groups, comprising: adding 2-methacryloyloxyethyl phosphorylcholine (MPC, III), fatty acid methacrylate (IV), and methacrylate containing active groups (V) to an initiator and a solvent for polymerization reaction, and then post-treating the obtained polymerization solution to obtain a phosphorylcholine copolymer (I) containing active groups.

[0058] The process route is as follows:

[0059] In equation (Ⅳ), 0 ≤ m ≤ 25;

[0060] In formula (V), R is selected from H, hydroxyl (-OH), carboxyl (-COOH), amino (-NH2), or epoxy group;

[0061] In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2) n NH2, where 0 ≤ n ≤ 8.

[0062] When m in formula (Ⅳ) is not equal to 0, the chemical structure of the copolymer prepared is as shown in formula (I), which is a ternary copolymer.

[0063] When m equals 0 in formula (Ⅳ), the chemical structure of the copolymer prepared is shown in formula (II), which is a binary copolymer;

[0064] In reaction (II), x and y represent the number of repeating units, respectively. x is a positive integer greater than 0, and y is a positive integer greater than 0.

[0065] In the above preparation method, the molar ratio of 2-methacryloyloxyethyl phosphoric acid choline, fatty acid methacrylate, and methacrylate containing an active group is 1-15:0-4:0.5-4. For example, the molar ratio of 2-methacryloyloxyethyl phosphoric acid choline, fatty acid methacrylate, and methacrylate containing an active group can be 4-10:0-3:0.5-3. In some specific embodiments, it can be 6-8:0-3:0.5-3, 6-8:1-2:1-2, or 4-10:1-2:1-2.

[0066] The above preparation method is a free radical solution copolymerization method. 2-Methacryloxyethylphosphocholine, fatty acid methacrylate, and methacrylate containing active groups are used as monomers. 2-Methacryloxyethylphosphocholine is a zwitterionic compound designed and synthesized based on a cell membrane-mimicking structure, thus exhibiting good biocompatibility and hydrophilicity.

[0067] In the above preparation method, the concentration of 2-methacryloyloxyethyl phosphocholine is ≤2000 mg / kg.

[0068] In the above preparation method, the concentration of the methacrylate fatty acid ester is ≤1000mg / kg.

[0069] In the above preparation method, the concentration of the methacrylate containing the active group is ≤1000 mg / kg.

[0070] In the above preparation method, the initiator is an additive that initiates a free radical polymerization reaction. Specifically, for example, the initiator is selected from at least one of azobisisobutyronitrile, benzoyl peroxide, or N,N-dimethylaniline.

[0071] In the above preparation method, the mass ratio of 2-methacryloyloxyethyl phosphocholine to the initiator is 100:0.5-2. For example, it can be 100:0.5-1, 100:0.5-1.5, or 100:1-1.5. In some specific embodiments, it can be 100:0.5-1.5, 100:1-1.5, or 100:1.5-2.

[0072] In the above preparation method, the solvent is selected from one or a mixture of two of water or alcohols. Specifically, the alcohol is selected from one or a mixture of anhydrous ethanol, n-propanol, isopropanol, or butanol.

[0073] In the above preparation method, the total volume ratio of the solvent to the reactants is 2-5:1. For example, it can be 2-2.5:1. In some specific embodiments, it can be 2-3:1, 2-4:1, or 2-4.5:1.

[0074] The reactants include 2-methacryloyloxyethyl phosphocholine, fatty acid methacrylates, and methacrylates containing active groups.

[0075] In the above preparation method, the polymerization reaction is carried out in a polymerization reactor.

[0076] In the above preparation method, the 2-methacryloyloxyethyl phosphocholine, fatty acid methacrylate, methacrylate containing active groups, initiator and solvent are thoroughly mixed.

[0077] In the above preparation method, high-purity nitrogen is bubbled before the polymerization reaction to remove oxygen, and the high-purity nitrogen is nitrogen gas with a concentration of ≥99.999%.

[0078] In some specific embodiments, the high-purity nitrogen bubbling time is 15-20 minutes, preferably 20 minutes.

[0079] In the above preparation method, the heating temperature of the polymerization reaction is 20–100°C, preferably 30–90°C. In some specific embodiments, it can be 30–50°C, 50–70°C, or 70–90°C.

[0080] In the above preparation method, the reaction time of the polymerization reaction is 4–50 h, preferably 5–48 h. In some specific embodiments, it can be 5–20 h, 20–30 h, or 30–48 h.

[0081] In the above preparation method, the polymerization reaction is carried out by stirring with a stirrer. In some specific embodiments, the stirrer is a magnetic stirrer.

[0082] In the above preparation method, the post-processing includes: cooling the polymerization solution, adding a precipitant to allow it to settle, then letting it stand, taking the solid, washing and drying it to provide the desired phosphorylcholine terpolymer.

[0083] In the above post-processing, the temperature is cooled to room temperature. The room temperature is 20–30°C.

[0084] In the above post-processing, the precipitant is selected from at least one of petroleum ether, n-hexane, ethyl acetate, acetone, or anhydrous diethyl ether.

[0085] In the above post-processing, the settling time is 1–15 hours, preferably 2–12 hours. In some specific embodiments, it can be 2–4 hours, 4–8 hours, or 8–12 hours.

[0086] In the above post-treatment, the volume ratio of the precipitant to 2-methacryloyloxyethyl phosphocholine is 2–20:1. For example, it can be 5–15:1. In some specific embodiments, it can be 5–6:1, 6–7:1, or 7–8:1.

[0087] In the above post-processing, the step of letting the sample stand overnight is performed.

[0088] In the above post-processing, the washing is performed using acetone or petroleum ether as the solvent.

[0089] In the above post-processing, the drying is vacuum drying, and the drying temperature is 20–100°C, preferably 30–90°C. In some specific embodiments, it can be 30–50°C, 50–60°C, 60–70°C, or 70–90°C.

[0090] In the above post-processing, the material is pulverized after drying. The phosphorylcholine copolymer containing active groups is a white powder solid.

[0091] A third aspect of the present invention provides the above-mentioned phosphorylcholine copolymer containing active groups, which is prepared by the above method.

[0092] A fourth aspect of the present invention provides a method for modifying an efficacy raw material with a phosphorylcholine copolymer containing an active group, comprising: mixing and reacting the efficacy raw material with the aforementioned phosphorylcholine copolymer containing an active group and a solvent to provide a desired efficacy raw material composition modified with a phosphorylcholine copolymer containing an active group.

[0093] In the above method, the active ingredient is selected from at least one of sodium hyaluronate, phytosphingosine, collagen, tea extract (EGCG), ergothioneine, glycyrrhizin, resveratrol, retinoic acid, dihydroxyacetone, or retinol and its derivatives.

[0094] The mechanism of the above-mentioned phosphorylcholine copolymer containing active groups to modify functional raw materials is to utilize the supramolecular forces between the phosphorylcholine copolymer and the active molecules of the functional raw materials, such as hydrogen bonding, intermolecular forces, and encapsulation. The modification results can significantly enhance the solubility, activity stability, color stability, and transdermal absorption efficiency of the functional raw materials. At the same time, the efficacy of the active materials is equal to or enhanced, making them easier to use in cosmetics.

[0095] The aforementioned active ingredients all contain active groups such as hydroxyl, amino, and carboxyl groups. Furthermore, these ingredients possess strong cosmetic effects, such as moisturizing, repairing, whitening, tanning, anti-aging, and antioxidant properties. However, they also present certain application challenges, including poor solubility, easy decomposition and inactivation, easy discoloration, low transdermal absorption efficiency, and a sticky, pilling texture.

[0096] In some specific embodiments, the molecular formula and structural formula of the active ingredient are shown in Table 1 below.

[0097] Table 1

[0098] In the above-mentioned active ingredients, the retinol derivative is selected from at least one of retinol propionate, retinol acetate, hydroxypinazone retinate, or retinol retinate.

[0099] In the above method, the mass ratio of the active ingredient to the phosphorylcholine copolymer containing the active group is 0.1 to 1000:1. In some specific embodiments, it can be 0.1 to 1:1, 1 to 10:1, 10 to 100:1, 100 to 1000:1, or 5 to 500:1.

[0100] In the above method, the solvent is selected from at least one of water, butanediol, propylene glycol, ethoxydiethylene glycol, caprylic / capric triglyceride, and caprylic / capric triglyceride.

[0101] In the above method, the mass ratio of the active ingredient to the solvent is 1:9-11. For example, it can be 1:9-10 or 1:10-11. In some specific embodiments, it can be 1:10.

[0102] In the above method, the stirring rate of the mixing reaction is ≤500 rpm / min. For example, it can be ≤400 rpm / min. In some specific embodiments, it can be ≤300 rpm / min.

[0103] In the above method, the mixing reaction is carried out in a reaction vessel.

[0104] In the above method, the temperature of the mixing reaction is 10–80°C, preferably 20–70°C. In some specific embodiments, it can be 20–40°C, 40–60°C, or 60–70°C.

[0105] In the above method, the reaction time of the mixing reaction is 0.5 to 5 hours. In some specific embodiments, it can be 0.5 to 1 hour, 1 to 3 hours, or 3 to 5 hours.

[0106] In the above method, the system of the functional raw material composition modified with phosphorylcholine copolymer containing active groups is selected from one of aqueous solution, oil solution, emulsion or liquid crystal system.

[0107] The fifth aspect of the present invention provides a functional raw material composition modified with a phosphorylcholine copolymer containing an active group, which is prepared by the above method.

[0108] The sixth aspect of the present invention provides the use of the above-mentioned phosphorylcholine copolymer containing active groups, or the above-mentioned phosphorylcholine copolymer modified with active groups, in cosmetics.

[0109] In the above-mentioned uses, the cosmetics include, but are not limited to, various dosage forms such as lotions, serums, creams, facial oils, and makeup. The functional ingredient composition modified with phosphorylcholine copolymer containing active groups is used in cosmetics as a functional ingredient.

[0110] The efficacy ingredient composition modified with phosphorylcholine copolymer containing active groups can solve the application difficulties of the corresponding efficacy ingredients, and can significantly enhance the solubility, activity stability, color stability and transdermal absorption efficiency of the efficacy ingredients, while the efficacy of the active ingredients is equal to or enhanced.

[0111] The following specific examples illustrate the implementation of the present invention. Those skilled in the art can easily understand other advantages and effects of the present invention from the content disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and various details in this specification can also be modified or changed based on different viewpoints and applications without departing from the spirit of the present invention.

[0112] When numerical ranges are given in the embodiments, it should be understood that, unless otherwise stated in the present invention, both endpoints of each numerical range and any value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in this invention have the same meaning as commonly understood by one of ordinary skill in the art. In addition to the specific methods, apparatus, and materials used in the embodiments, based on the knowledge of the prior art possessed by one of ordinary skill in the art and the description of this invention, any prior art methods, apparatus, and materials similar to or equivalent to those described, apparatus, and materials in the embodiments of this invention may be used to implement the present invention.

[0113] Example 1

[0114] Weigh 40.82 g of 2-methacryloyloxyethyl phosphocholine, 19.66 g of n-butyl methacrylate, 6.33 g of methacrylic acid, and 0.57 g of azobisisobutyronitrile and transfer them to a 1000 mL round-bottom flask. Add 300 mL of anhydrous ethanol and stir at room temperature until completely dissolved. Bubble with high-purity nitrogen for 20 minutes, then seal the flask and heat to 60 °C for 18 hours for polymerization. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, allow the mixture to settle in anhydrous diethyl ether (10:1 volume ratio of anhydrous diethyl ether to 2-methacryloyloxyethyl phosphocholine) for 8 hours. Wash with acetone and dry under vacuum at 40 °C to constant weight to obtain a white powdery polymer, namely, sample 1# (60.25 g) of phosphorylcholine copolymer containing active groups. Qualitative analysis revealed that sample 1#, a phosphorylcholine copolymer containing active groups, is a terpolymer of phosphorylcholine containing carboxyl active groups. Its 1H NMR spectrum is shown in Figure 1, its GPC spectrum in Figure 2, and its infrared spectrum in Figure 3. In Figure 2, the weight-average molecular weight M of sample 1#, containing active groups, is... w=114511g / mol, PDI=3.42.

[0115] Example 2

[0116] Weigh 66.44 g of 2-methacryloyloxyethyl phosphocholine, 3.25 g of glycidyl methacrylate (with the same chemical structure as shown in reaction formulas IV and V), and 0.808 g of benzoyl peroxide, and transfer them to a 1000 mL round-bottom flask. Add 180 mL of anhydrous ethanol and 90 mL of DMF to the flask, and stir at room temperature until the solid is completely dissolved. Then bubble with high-purity nitrogen for 30 minutes, seal the flask, and heat to 40 °C for polymerization for 14 h. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, cool the polymer solution to room temperature and precipitate it in acetone for 10 h. The volume ratio of acetone to 2-methacryloyloxyethyl phosphocholine is 15:1. After washing with acetone, dry under vacuum at 40 °C to constant weight to obtain a white powdery polymer, namely, sample 2# 67.91 g of phosphorylcholine copolymer containing active groups. Qualitative analysis revealed that sample 2#, a phosphorylcholine copolymer containing active groups, is a phosphorylcholine binary polymer containing epoxy active groups. The 1H NMR spectrum is shown in Figure 4, the GPC spectrum in Figure 5, and the IR spectrum in Figure 6.

[0117] Example 3

[0118] Weigh 48.06 g (162.75 mmol) of 2-methacryloyloxyethyl phosphocholine, 23.14 g (162.75 mmol) of n-butyl methacrylate, 55.10 g (162.75 mmol) of octadecyl methacrylate, and 1.14 g (7 mmol) of azobisisobutyronitrile and transfer them to a 2000 mL round-bottom flask. Add 600 mL of anhydrous ethanol and stir at room temperature until completely dissolved. Bubble with high-purity nitrogen for 20 minutes, then seal the flask and heat to 60 °C for polymerization for 10 hours. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, allow the mixture to settle in anhydrous diethyl ether for 1 hour. The volume ratio of anhydrous diethyl ether to 2-methacryloyloxyethyl phosphocholine is 5:1. Wash with acetone and dry under vacuum at 40 °C to constant weight to obtain a white powdery polymer, namely, sample 3# 110 g of phosphorylcholine copolymer containing active groups. Qualitative testing revealed that sample 3#, containing active groups, is a phosphorylcholine terpolymer containing octadecyl long-chain active groups.

[0119] Example 4

[0120] Weigh 48.06 g (162.75 mmol) of 2-methacryloyloxyethyl phosphocholine, 23.14 g (162.75 mmol) of n-butyl methacrylate, 30.15 g (162.75 mmol) of diethylaminoethyl methacrylate, and 1.14 g (7 mmol) of azobisisobutyronitrile and transfer them to a 2000 mL round-bottom flask. Add 600 mL of anhydrous ethanol and stir at room temperature until completely dissolved. Bubble with high-purity nitrogen for 20 minutes, then seal the flask and heat to 60 °C for polymerization for 10 hours. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, allow the mixture to settle in anhydrous diethyl ether for 1 hour (the volume ratio of anhydrous diethyl ether to 2-methacryloyloxyethyl phosphocholine is 20:1). Wash with acetone and dry under vacuum at 40 °C to constant weight to obtain a white powdery polymer, namely, 100 g of phosphorylcholine copolymer sample 4# containing active groups. Qualitative testing revealed that sample 4#, a phosphorylcholine copolymer containing active groups, is a phosphorylcholine terpolymer containing amine active groups.

[0121] Example 5

[0122] Weigh 48.06 g (162.75 mmol) of 2-methacryloyloxyethyl phosphocholine, 23.14 g (162.75 mmol) of n-butyl methacrylate, 21.18 g (162.75 mmol) of hydroxyethyl methacrylate, and 1.14 g (7 mmol) of azobisisobutyronitrile and transfer them to a 1000 mL round-bottom flask. Add 300 mL of anhydrous ethanol and stir at room temperature until completely dissolved. Bubble with high-purity nitrogen for 20 minutes, then seal the flask and heat to 50 °C for 15 hours. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, allow the mixture to settle in anhydrous diethyl ether for 2 hours (the volume ratio of anhydrous diethyl ether to 2-methacryloyloxyethyl phosphocholine is 12:1). Wash with acetone and dry under vacuum at 30 °C to constant weight to obtain a white powdery polymer, namely, 85 g of the phosphorylcholine copolymer sample 5# containing active groups. Qualitative testing revealed that sample 5#, containing an active group, is a hydroxyl-containing phosphorylcholine copolymer.

[0123] Example 6

[0124] Weigh 6.0 g of sodium hyaluronate with an average molecular weight of 1.2 million Daltons, and add 1.2 g of phosphorylcholine copolymer sample 1# containing active groups obtained in Example 1 to a 500 mL round-bottom flask. Then add 182.8 g of deionized water, heat to 50 °C, and stir at 500 rpm / min for 3 h until completely dissolved. Then cool to room temperature and stir evenly to obtain the modified sodium hyaluronate aqueous solution as the efficacy raw material composition sample 1*.

[0125] Example 7

[0126] Weigh 2.0g of phytosphingosine powder and add 8.0g of the amino-containing phosphorylcholine copolymer obtained in Example 4 to a 500mL round-bottom flask. Then add 180.0g of deionized water, heat to 40℃, stir at 400rpm / min for 4h until completely dissolved, and then cool to room temperature to obtain the modified phytosphingosine aqueous solution as the efficacy raw material composition sample 2*.

[0127] Example 8

[0128] Weigh 1.0g of tea extract EGCG, and add 0.4g of the hydroxyl-containing phosphorylcholine copolymer obtained in Example 5, 30.0g of caprylic / capric glycerides, 35.0g of isononyl isononanoate, and 33.6g of propylene glycol to a 300mL beaker. Heat to 30°C, stir at 300rpm / min for two hours, and then cool to room temperature to obtain a modified EGCG oil solution as the efficacy raw material composition sample 3*.

[0129] Example 9

[0130] Weigh 2.0g of collagen, and add 1.0g of the hydroxyl-containing phosphorylcholine copolymer obtained in Example 5 and 97.0g of deionized water to a 300mL beaker. Heat to 35℃, stir at 300rpm / min for 1h, and then cool to room temperature to obtain the modified collagen aqueous solution as the efficacy raw material composition sample 4*.

[0131] Comparative Example 1

[0132] Weigh 6.0 g of sodium hyaluronate with an average molecular weight of 1.2 million Daltons, add it to a 500 mL round-bottom flask, add 184 g of deionized water, heat to 50 °C, stir for 3 h until completely dissolved, then cool to room temperature, stir evenly to obtain sodium hyaluronate hydrogel as control sample 1.

[0133] Comparative Example 2

[0134] Weigh 2.0g of phytosphingosine, add 188g of deionized water, heat to 40℃, stir for 4h, and then cool to room temperature to obtain a suspension of phytosphingosine as control sample 2.

[0135] Comparative Example 3

[0136] Weigh 1.0g of tea extract EGCG, add 99g of deionized water, add to a 300mL beaker, heat to 30℃, stir at 300rpm / min for 2h until completely dissolved, then cool to room temperature, stir evenly to obtain the modified EGCG oil solution as control sample 3.

[0137] Comparative Example 4

[0138] Weigh 2.0g of collagen, add 98g of deionized water, add to a 300mL beaker, heat to 35℃, stir at 300rpm / min for 1h, and then cool to room temperature to obtain the modified collagen aqueous solution as control sample 4.

[0139] Comparative Example 5

[0140] Weigh 48.06 g (162.75 mmol) of 2-methacryloyloxyethyl phosphocholine, 23.14 g (162.75 mmol) of n-butyl methacrylate, 21.18 g (162.75 mmol) of methacrylate containing active groups, and 1.14 g (7 mmol) of azobisisobutyronitrile and transfer them to a 3000 mL round-bottom flask. Add 1000 mL of anhydrous ethanol, stir at room temperature until completely dissolved, bubble with high-purity nitrogen for 20 minutes, seal the flask, and heat to 85 °C for polymerization reaction for 3 hours. Stir with a magnetic stirrer throughout the polymerization process. After the reaction is complete, allow it to settle in anhydrous diethyl ether for 1 hour. The volume ratio of anhydrous diethyl ether to 2-methacryloyloxyethyl phosphocholine is 1:1. Wash with acetone, dry under vacuum at 80 °C to constant weight, and obtain a white powdery polymer, which is control sample 5.

[0141] Comparative Example 6

[0142] Weigh 10g of sodium hyaluronate and add 2g of the control sample 5 obtained in Comparative Example 5 to a 500mL round-bottom flask. Then add 130g of deionized water, heat to 35℃, and stir at 600rpm / min for 0.5h until completely dissolved. Then cool to room temperature and stir evenly to obtain the modified sodium hyaluronate aqueous solution as control sample 6.

[0143] Test Comparison Example 1

[0144] The efficacy ingredient composition sample 1* obtained in Example 6 was compared with the comparative sample 1 obtained in Comparative Example 1. The specific appearance of both is shown in Figure 7, and the specific material composition is shown in Figure 8. As shown in Figure 7, the efficacy ingredient composition sample 1*, being a modified sodium hyaluronate aqueous solution, exhibited significantly reduced viscosity and improved fluidity. This indicates that through supramolecular technology, under certain conditions, the phosphorylcholine copolymer and sodium hyaluronate interact in a non-covalent manner, forming a new stable structure through intermolecular forces or hydrogen bonding. This significantly weakens the hydration of sodium hyaluronate with water molecules, thereby reducing the viscosity of its aqueous solution. In contrast, the comparative sample 1 showed no fluidity. Furthermore, as shown in Figure 8, the efficacy ingredient composition sample 1* exhibited good fluidity in the characteristic frequency region of esters (1735-1750 cm⁻¹). -1 No characteristic peaks were found at the location, thus proving that no new substances were generated.

[0145] Test Comparison Example 2

[0146] The efficacy ingredient composition sample 1* obtained in Example 6 was subjected to a moisturizing clinical efficacy test on 25 people, and the test results are shown in Figure 10. As shown in Figure 10, the modification with the phosphorylcholine polymer containing active groups not only greatly improved the sticky feel of sodium hyaluronate, but also enhanced the overall moisturizing ability of the raw material. The results of the moisturizing clinical efficacy test on 25 people showed that the modified sodium hyaluronate had a better moisturizing effect, which was superior to the use of sodium hyaluronate alone, the polymer, and the combination of the two compared with the original product.

[0147] Test Comparison Example 3

[0148] The efficacy ingredient composition sample 2* obtained in Example 7 was compared with the comparative sample 2 obtained in Comparative Example 2. The specific appearance of the two is shown in Figure 9. As shown in Figure 9, the efficacy ingredient composition sample 2* is a clear solution, while the comparative sample 2 contains a large amount of insoluble matter and has no flowability. It is evident that the phosphorylcholine copolymer and phytosphingosine, through supramolecular interactions, improve the water solubility of phytosphingosine, which is beneficial for high-content addition in cosmetics. It can be used in transparent aqueous solutions or serum formulations, expanding formulation possibilities.

[0149] Test Comparison Example 4

[0150] Sample 2* of the efficacy ingredient composition obtained in Example 7 was subjected to short-term exposure to cosmetic ingredients using cultured rabbit corneal epithelial cells (SIRC) to simulate acute corneal irritation. The relative cell survival rate was calculated to predict eye damage caused by cosmetic chemicals. The test results are shown in Figure 11. Figure 11 shows that the safety of phytosphingosine was improved; after modification with a phosphorylcholine copolymer containing active groups, its safety was superior to that of unmodified phytosphingosine.

[0151] Test Comparison Example 5

[0152] The efficacy raw material composition sample 3* obtained in Example 8 and the comparative sample 3 obtained in Comparative Example 3 were placed in an oven at 45°C to examine the color stability. The results are shown in Figure 12. At the same time, the retention rate of the active ingredient was monitored by HPLC. The results are shown in Table 2.

[0153] Table 2

[0154] As shown in Figure 12 and Table 2, the EGCG modified with phosphorylcholine copolymer showed significant improvement in color change and activity loss under high temperature accelerated test conditions, indicating that modification can improve the stability of the active material.

[0155] Test Comparison Example 6

[0156] The expression of skin barrier repair-related genes in the two samples before and after modification were tested, and the efficacy raw material composition sample 4* obtained in Example 9 and the comparative sample 4 obtained in Comparative Example 4 were compared. The results are shown in Figure 13.

[0157] As shown in Figure 13, the collagen modified with phosphorycholine copolymer showed significantly improved effects in repairing the stratum corneum, promoting keratinocyte differentiation, moisturizing, and maintaining normal skin function, indicating that modification can promote the efficacy of active ingredients.

[0158] Test Comparison Example 7

[0159] The efficacy raw material composition sample 1* obtained in Example 6 was compared with the comparative sample 6 obtained in Comparative Example 6, and a clinical moisturizing efficacy test was conducted on 25 people. Specifically, the reduction test of skin water loss was conducted, which is an important indicator for evaluating the strength of skin barrier function by the level of transepidermal water loss (TEWL value).

[0160] Testing instrument: Skin transepidermal water loss tester.

[0161] Test Samples: Sample 1 of the efficacy ingredient composition obtained in Example 6 vs. Comparative Sample 6 obtained in Comparative Example 6

[0162] Twenty-five subjects aged 20-40 years with dry skin were selected. A 3×3 cm² test area was marked on the inner forearm of both subjects. Multiple areas could be marked on the same arm, spaced 1 cm apart. Test samples and blank controls were randomly distributed on both arms. A capacitive skin analyzer was used to measure the test and control areas. Each area was measured 15 times in parallel. First, the blank value of each test area was measured, then 0.5 g of test sample / 9 cm² was used. 2 The product was evenly applied to the test area. Skin moisture content in the test area and the control area was measured at 1, 2, 4, and 8 hours after application (measurements were performed at these times during validation). No products (cosmetics or topical medications) should be used on the test site for 2-3 days prior to the test. The test environment temperature was controlled at 25±1℃, and the relative humidity at 40±5%. Before the test, the subjects' arms were wiped with purified water at approximately 36℃. The subjects sat quietly in the test environment for 30 minutes before the test. The TEWL values ​​were measured at each time point according to the experimental design, and the reduction in skin moisture loss at each time point was calculated. The greater the reduction in skin moisture loss, the better the skin barrier repair effect. The results are shown in Table 3 below.

[0163] Table 3

[0164] The results in Table 3 show that the efficacy ingredient composition sample 1* of Example 6 exhibits minimal moisture reduction during prolonged moisturizing, indicating that the phosphorylcholine copolymer sample 1# containing active groups obtained in Example 1, which is included in the efficacy ingredient composition sample 1*, can provide long-lasting moisturizing and lock in moisture for the skin.

[0165] The above embodiments are for illustrating the implementation schemes disclosed in this invention and should not be construed as limiting the invention. Furthermore, various modifications and variations of the methods listed herein will be apparent to those skilled in the art without departing from the scope and spirit of the invention. Although the invention has been specifically described in conjunction with various specific preferred embodiments, it should be understood that the invention should not be limited to these specific embodiments. In fact, various modifications as described above that are obvious to those skilled in the art to obtain the invention should be included within the scope of this invention.

Claims

1. A phosphorylcholine copolymer containing an active group, the chemical structure of said copolymer being shown in formula (I): In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2) n NH2, of which, 0≤n≤8。 2. The phosphorylcholine copolymer containing active groups according to claim 1, characterized in that, Includes one or more of the following conditions: A1) x, y, and z represent the number of repeating units, where x is a positive integer greater than 0, z is a positive integer greater than 0, and y is an integer greater than or equal to 0. A2) m is a positive integer greater than or equal to 0 and less than or equal to 25; A3) n is an integer greater than or equal to 0 and less than or equal to 8; A4) When y equals 0, the chemical structure of the copolymer is shown in formula (II), which is a binary copolymer; In reaction (II), x and y represent the number of repeating units, respectively. x is a positive integer greater than 0, and y is a positive integer greater than 0.

3. A method for preparing a phosphorylcholine copolymer containing an active group, comprising: 2-Methacryloxyethylphosphocholine (MPC, III), fatty acid methacrylate (IV), and methacrylate containing active groups (V) were added to an initiator and a solvent for polymerization. The resulting polymer solution was then post-treated to obtain a phosphorylcholine copolymer (I) containing active groups. The process route is as follows: In equation (Ⅳ), 0 ≤ m ≤ 25; In formula (V), R is selected from H, hydroxyl (-OH), carboxyl (-COOH), amino (-NH2), or epoxy group; In equation (I), x > 0; z > 0; y ≥ 0; 0 ≤ m ≤ 25; R is selected from H and (CH2). n OH, (CH2) n CHOCH2 or (CH2) n NH2, where 0 ≤ n ≤ 8.

4. The method for preparing the phosphorylcholine copolymer containing active groups according to claim 3, characterized in that, Includes one or more of the following conditions: B1) When m equals 0 in formula (Ⅳ), the chemical structure of the copolymer prepared is shown in formula (II), which is a binary copolymer; B2) The molar ratio of 2-methacryloyloxyethyl phosphocholine, fatty acid methacrylate, and methacrylate containing active groups is 1-15:0-4:0.5-4; B3) The initiator is selected from at least one of azobisisobutyronitrile, benzoyl peroxide or N,N-dimethylaniline; B4) The mass ratio of 2-methacryloyloxyethyl phosphocholine to the initiator is 100:0.5-2; B5) The solvent is selected from one or a mixture of two of water or alcohol; B6) The total volume ratio of the solvent to the reactants is 2-5:1; B7) High-purity nitrogen is used for bubbling before the polymerization reaction to remove oxygen; preferably, the high-purity nitrogen bubbling time is 15-20 min; B8) The heating temperature for the polymerization reaction is 20–100°C; B9) The polymerization reaction time is 4–50 h; The post-processing described in B10 includes: cooling the polymerization solution, adding a precipitant to allow it to settle, then allowing it to stand, taking the solid, washing and drying it to provide the desired phosphorylcholine terpolymer.

5. The method for preparing the phosphorylcholine copolymer containing active groups according to claim 4, characterized in that, Item B10) includes one or more of the following conditions: B101) describes cooling to room temperature; The precipitant described in B102) is selected from at least one of petroleum ether, n-hexane, ethyl acetate, acetone, or anhydrous diethyl ether; The settling time described in B103 is 1–15 hours; The volume ratio of the precipitant to 2-methacryloyloxyethyl phosphocholine (B104) is 2–20:

1. B105) describes the overnight standing condition; B106) The washing process uses acetone or petroleum ether as the solvent; B107) The drying method is vacuum drying, and the drying temperature is 20-100℃; B108) requires pulverization after drying.

6. A phosphorylcholine copolymer containing an active group, prepared by the method according to any one of claims 3-5.

7. A method for modifying a functional raw material with a phosphorylcholine copolymer containing an active group, comprising: The active ingredient is mixed and reacted with the phosphorylcholine copolymer containing active groups according to any one of claims 1-2 and a solvent to provide the desired phosphorylcholine copolymer modified active ingredient composition.

8. The method for modifying functional raw materials with phosphorylcholine copolymers containing active groups according to claim 7, characterized in that, Includes one or more of the following conditions: C1) The active ingredients described are selected from at least one of sodium hyaluronate, phytosphingosine, collagen, tea extract (EGCG), ergothioneine, glycyrrhizin, resveratrol, retinoic acid, dihydroxyacetone or retinol and their derivatives. C2) The mass ratio of the functional raw material to the phosphorylcholine copolymer containing active groups is 0.1 to 1000:1; C3) The solvent is selected from at least one of water, butanediol, propylene glycol, ethoxydiethylene glycol, caprylic / capric triglyceride, and caprylic / capric triglyceride; The mass ratio of the active ingredient to the solvent described in C4) is 1:9-11; C5) The stirring rate of the mixing reaction is ≤500 rpm / min; The temperature of the mixing reaction described in C6) is 10–80°C; The reaction time for the mixture described in C7) is 0.5 to 5 hours.

9. A functional raw material composition modified with a phosphorylcholine copolymer containing an active group, prepared by the method according to any one of claims 7-8.

10. Use in cosmetics of the functional ingredient composition modified with the phosphorylcholine copolymer according to any one of claims 1-2, the phosphorylcholine copolymer according to claim 6, or the phosphorylcholine copolymer containing an active group according to claim 9.

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