WO2022166926A1 - Solution huileuse limpide de polymère de phosphorylcholine, solution mère de matière première cosmétique, leur procédé de préparation et leur application - Google Patents

Solution huileuse limpide de polymère de phosphorylcholine, solution mère de matière première cosmétique, leur procédé de préparation et leur application Download PDF

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WO2022166926A1
WO2022166926A1 PCT/CN2022/075196 CN2022075196W WO2022166926A1 WO 2022166926 A1 WO2022166926 A1 WO 2022166926A1 CN 2022075196 W CN2022075196 W CN 2022075196W WO 2022166926 A1 WO2022166926 A1 WO 2022166926A1
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stock solution
oil
ceramide
oily
raw material
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PCT/CN2022/075196
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English (en)
Chinese (zh)
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李小虎
程伟峰
陶礼
方慧静
张伟阳
钱佳
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上海奥利实业有限公司
上海奥利生物科技有限公司
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Priority claimed from CN202110146125.5A external-priority patent/CN112741781A/zh
Priority claimed from CN202110168629.7A external-priority patent/CN112891248A/zh
Priority claimed from CN202110179830.5A external-priority patent/CN113181080A/zh
Priority claimed from CN202110298003.8A external-priority patent/CN112915041A/zh
Application filed by 上海奥利实业有限公司, 上海奥利生物科技有限公司 filed Critical 上海奥利实业有限公司
Publication of WO2022166926A1 publication Critical patent/WO2022166926A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the invention relates to the field of cosmetic raw materials, in particular to a transparent oil solution of an oil-insoluble phosphorylcholine polymer, a cosmetic raw material stock solution and a preparation method and application thereof.
  • phosphorylcholine polymer has emerged as a biomimetic biomaterial with good biocompatibility.
  • This high-end medical biomimetic material has a high degree of biocompatibility and is mainly used in the fields of biomedicine and medical devices, and has been used in high-end medical devices.
  • Cosmetics are used as moisturizing raw materials.
  • Nippon Oil Co., Ltd. developed a series of biomimetic phosphorylcholine products, which are known as artificial cell membranes due to their extremely high moisturizing and breathable properties, as well as components and properties that are very similar to human cell membranes.
  • the phosphorylcholine polymer (artificial cell membrane) represented by polyquaternium-51 has gradually entered people's field of vision.
  • Base chain polymerization and adjust different polymerization ratios to achieve changes in product performance, and apply to different fields. It has excellent histocompatibility and hemocompatibility, and is often used in biomedical fields such as medical organ transplantation, eye care, and wound repair.
  • Applied in cosmetics it can form a breathable biofilm on the skin surface to form a breathable and water-retaining film, which can lock in water and moisturise intelligently, and has super moisturizing properties. Stimulates the skin, shields the dust in the environment, absorbs the stable charge layer, and eliminates static electricity.
  • polyquaternium-51 forms an excellent water-washable film with molecular nail effect, that is, it remains on the skin surface after multiple washings, long-lasting moisturizing and reducing irritation.
  • phosphorylcholine is mostly used in water-based products, which limits its application.
  • the purpose of the present invention is to provide a phosphorylcholine polymer oil solution (stock solution) suitable for cosmetics with high transparency, high stability and high biocompatibility, and its preparation method and use.
  • a phosphorylcholine polymer oily stock solution based on the total weight of the oily stock solution, comprising: 0.1-10% phosphorylcholine polymer, 5-50% emulsifier, and 5% -50% grease.
  • the oily stock solution also contains 0.1-5% antioxidant.
  • the antioxidant is selected from: tocopherol, tocopherol acetate, tocopherol succinate, tocopherol mixture, or a mixture thereof.
  • the phosphorylcholine polymer contains (a) a hydrophilic group; (b) a hydrophobic group.
  • the hydrophilic group contains a branched chain structure shown in formula I:
  • R 1 , R 2 and R 3 are each independently selected from: H, C 1 -C 4 alkane, and C 3 -C 4 cycloalkyl.
  • the main chain unit of the phosphorylcholine polymer is selected from the following group:
  • the phosphorylcholine group represented by formula I is through -CO-O-CH 2 -CH 2 -, -CO-O-CH 2 -CH 2 -O- , and/or -CO-O-(CH 2 )m-CH 2 - are attached to the main chain, where m is a positive integer from 2-17.
  • the main chain is selected from the following group: or
  • the phosphorylcholine polymer is selected from: 2-methacryloyloxyethyl phosphorylcholine homopolymer, 2-methacryloyloxyethyl phosphorylcholine and other Copolymers of hydrophilic and/or hydrophobic monomers or combinations thereof, polyphosphocholine glycol acrylate, polyphosphocholine n-butyl methacrylate, or combinations thereof.
  • the oil is selected from: isopropyl palmitate, isooctyl palmitate, isononyl isononanoate, white oil, glycerol caprylate/capric acid triester, octyldodecane Alcohol, Coco Acid, Lauryl Alcohol, Isopropyl Myristate, Shea Butter, Isooctyl 12-Hydroxystearate, Diisostearyl Malate, Squalane, Jojoba Oil, Soybean Oil , olive oil, sweet almond oil, avocado oil, wheat germ oil, or a combination thereof.
  • the emulsifier is selected from: polyglycerol esters, sorbitan fatty acid ester series, sorbitan cocoate, sucrose fatty acid ester, alkyl glycosides, hydrogenated lecithin, fat Alcohol polyoxyethylene ethers, alkylphenol polyoxyethylene ethers, fatty acid polyoxyethylene esters, polyethers, glycerol caprylic/capric acid esters, or combinations thereof.
  • step (2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
  • step (3) adding other oils and fats to the mixture described in step (2), and then cooling to 10-60° C. to obtain the phosphorylcholine polymer oily stock solution.
  • a use of the phosphorylcholine polymer oily stock solution described in the first aspect is provided for the manufacture of oil-based, water-in-oil, and oil-in-water formula cosmetics.
  • a cosmetic which contains the phosphorylcholine polymer oily stock solution described in the first aspect.
  • the cosmetic is an oil-based cosmetic or contains an oily auxiliary.
  • the oil-based cosmetics include: facial mask, spray, wet wipes, lotion, cream, cosmetic lotion, gel, shampoo, conditioner, hair and scalp care essence, makeup or other Cosmetic cosmetics for skin and hair, or combinations thereof.
  • a kind of cosmetic raw material stock solution is provided, and the described cosmetic raw material stock solution is selected from the following group:
  • (Y2) Ceramide oily stock solution based on the total weight of the oily stock solution, comprising: 0.1-10% ceramide, 0.05-10% liposome-like structure, 0.1-50% oil, 1-45% emulsifier; and
  • (Y3) Dipotassium glycyrrhizinate oily stock solution, based on the total weight of the oily stock solution, comprising: 0.1-10% dipotassium glycyrrhizinate, 0.05-10% liposome structural analog, 10-50% oil and 5-50% emulsification agent.
  • the stock solution is a licorice flavonoid oil stock solution, based on the total weight of the oily stock solution, comprising: 0.1-10% licorice flavonoids, 0.05-10% liposome structural analogs, 10-50% oil and 5% ⁇ 50% emulsifier.
  • the licorice flavonoids contain the whitening active ingredient glabridin represented by formula Y1:
  • the licorice flavonoids are encapsulated by liposome structural analogs to form a first encapsulation.
  • the stock solution is an oily ceramide stock solution, which, based on the total weight of the oily stock solution, comprises: 0.1-10% ceramide, 0.05-10% liposome-like structure, 0.1-50% oil, 1 ⁇ 45% emulsifier.
  • the ceramide is a compound represented by formula Y2:
  • R 1 is selected from: C 40-50 alkyl, C 40-50 alkenyl, C 40-50 alkynyl;
  • C 40-50 alkyl group, C 40-50 alkenyl group, C 40-50 alkynyl group all include: ester group, heteroaryl group, aryl group and combinations thereof;
  • R 2 is selected from: C 11-21 alkyl, C 11-21 alkenyl, C 11-21 alkyl containing hydroxyl, C 11-21 alkenyl containing hydroxyl, or combinations thereof.
  • the ceramide is selected from: ceramide 1 [EOS], ceramide 2 [NS], ceramide 3 [NP], ceramide 4 [EOS], ceramide 5 [AS], ceramide 5 [AS], amide 6 [NH], ceramide 6II, ceramide 7 [AP], ceramide 8 [AH], ceramide 9 [EOP], ceramide E, or a combination thereof;
  • the ceramide is encapsulated by a liposome structural analog to form a first encapsulation.
  • the stock solution is dipotassium glycyrrhizinate oily stock solution, based on the total weight of the oily stock solution, comprising: 0.1-10% dipotassium glycyrrhizinate, 0.05-10% liposome structural analog, 10-50% % oil and 5-50% emulsifier.
  • the dipotassium glycyrrhizinate contains the whitening active ingredient shown in formula Y3:
  • the dipotassium glycyrrhizinate is encapsulated by a liposome structural analog to form a first encapsulation.
  • the liposome structural analog contains (a) a hydrophilic group; (b) a hydrophobic group.
  • the hydrophilic group contains a branched chain structure shown in formula I:
  • R1, R2 and R3 are each independently selected from: H, C1-C4 alkane, C3-C4 cycloalkyl;
  • hydrophobic group comprises: C5-30 aliphatic chain structure.
  • the oil is selected from: isopropyl palmitate, isooctyl palmitate, isononyl isononanoate, white oil, glycerol caprylate/capric acid triester, octyldodecane Alcohol, Coco Acid, Lauryl Alcohol, Isopropyl Myristate, Shea Butter, Isooctyl 12-Hydroxystearate, Diisostearyl Malate, Squalane, Jojoba Oil, Soybean Oil , olive oil, sweet almond oil, avocado oil, wheat germ oil, or a combination thereof.
  • the emulsifier is selected from: polyglycerol esters, sorbitan fatty acid ester series, sorbitan cocoate, sucrose fatty acid ester, alkyl glycosides, hydrogenated lecithin, fat Alcohol polyoxyethylene ethers, alkylphenol polyoxyethylene ethers, fatty acid polyoxyethylene esters, polyethers, glycerol caprylic/capric acid esters, or combinations thereof.
  • a method for preparing the cosmetic raw material stock solution described in the fifth aspect of the present invention comprising the steps of:
  • (a1) provide licorice flavonoids, liposome structural analogs and emulsifiers, and mix them into an oil phase mixture according to a certain proportion;
  • step (a2) heating the oil phase mixture in step (a1) (eg, 45-120° C.) to form a heated mixture;
  • step (a3) adding grease to the mixture described in step (a2), then cooling down (such as cooling to 20-80°C, preferably 20-45°C) to obtain the glycyrrhizin oily stock solution of cooling;
  • (b1) provide ceramide, liposome-like structure and oil, and mix them into oil phase mixture according to a certain proportion
  • step (b2) heating the oil phase mixture in step (b1) to 45-120°C;
  • step (b3) adding an emulsifier to the mixture described in step (b2), then cooling to 20-80° C., preferably 20-45° C., to obtain an oil-phase mixture to obtain the ceramide oily stock solution;
  • (c1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
  • step (c2) heating the oil phase mixture in step (c1), thereby forming a heated mixture
  • step (c3) adding grease to the mixture described in step (c2), and then cooling down to obtain the oily stock solution of dipotassium glycyrrhizinate is the oily stock solution of dipotassium glycyrrhizinate.
  • the raw material stock solution described in the fifth aspect of the present invention for preparing cosmetic products of oil-based, water-in-oil, and oil-in-water formulations.
  • a cosmetic product which contains the raw material solution according to the fifth aspect of the present invention.
  • Figure 1 shows a transparent phosphorylcholine polymer oily stock solution prepared in one example of the present invention.
  • Figure 2 shows the mixed solution (cloudy solution) of phosphorylcholine polymer and oil in the prior art.
  • Figure 3 shows the transparent licorice flavonoid oily stock solution prepared in one example of the present invention.
  • Figure 4 shows the prior art mixture (emulsion) of licorice flavonoids and oil.
  • Figure 5 shows a transparent ceramide oily stock solution prepared in one example of the present invention.
  • Fig. 6 shows the mixed solution (precipitate) formed by ceramide and oil in the prior art.
  • Figure 7 shows a transparent dipotassium glycyrrhizinate oily stock solution prepared in one example of the present invention.
  • Figure 8 shows the prior art mixture (suspension) of dipotassium glycyrrhizate and oil.
  • the inventor unexpectedly developed a highly stable, highly compatible and transparent phosphorylcholine polymer oily stock solution for the first time. Specifically, the inventors obtained an oily stock solution with high transparency, high stability and high biocompatibility by adding specific components (phosphorylcholine polymer emulsifier and oil).
  • the high-transparency oily stock solution of the present invention can be widely used in cosmetics, thereby improving the quality and effect of cosmetics.
  • the present invention has been completed on this basis.
  • the phosphorylcholine polymer oil solution (also referred to as "oily stock solution”) of the present invention utilizes the hydrophobic side chain groups (or monomers) and hydrophilic side chains in the phosphorylcholine polymer structure group (or monomer), which is dissolved in a specific emulsifier, so that the solubility of phosphorylcholine polymer in oil-based, water-in-oil, oil-in-water formulations of cosmetics can be significantly improved, and high Transparency, high stability, high biocompatibility of oily stock solution.
  • the transparent phosphorylcholine polymer oil solution of the present invention is not only favorable for applying the phosphorylcholine polymer to oil-based, water-in-oil, and oil-in-water formula cosmetics, but also facilitates the formation of the phosphorylcholine polymer on the skin through the formation of the phosphorylcholine polymer on the skin.
  • Membrane properties reduce irritation and improve moisturizing and repairing effects, and solve the problems of insoluble in oil, poor stability and low bioavailability of phosphorylcholine polymers in the prior art.
  • the present invention also develops a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
  • the present invention develops a highly stable, highly compatible and transparent licorice flavonoid oily stock solution, ceramide oil solution (also known as "oily stock solution” oliy stock solution), dipotassium glycyrrhizinate oily stock solution .
  • active ingredient As used herein, for the oily stock solution of the present invention, "active ingredient”, “oily stock solution of the present invention” and “phosphorylcholine polymer of the present invention” are used interchangeably, all referring to the active ingredient phosphorylcholine A polymer containing the above-mentioned (a) hydrophilic group and (b) hydrophobic group.
  • oil-insoluble phosphorylcholine Polymers are mixed with specific ingredients such as emulsifiers and oils to form oily stock solutions with high transparency, high stability and high biocompatibility.
  • a core component is phosphorylcholine polymer (also called liposome-like structure).
  • phosphorylcholine polymer of the present invention and “liposome analog structure of the present invention” are used interchangeably.
  • phosphorylcholine polymers refer to polymers containing phosphorylcholine groups, especially polymers containing phosphorylcholine groups in side chains.
  • the phosphorylcholine polymers of the present invention may be homopolymers or copolymers, including random copolymers, block copolymers, or combinations thereof.
  • the copolymers of the present invention may be binary, tertiary or multicomponent copolymers.
  • the phosphorylcholine group can be directly attached to the polymer backbone (eg, terminated to the polymer), or it can be linked through a linking group (eg, a divalent linking group, or A divalent linking group) is indirectly linked to the main chain.
  • a linking group eg, a divalent linking group, or A divalent linking group
  • the preferred phosphorylcholine polymers also contain hydrophobic groups, such as hydrophobic groups located on side chains, or hydrophobic groups located at the terminals.
  • the phosphorylcholine polymer of the present invention is a copolymer formed by copolymerizing, for example, a phosphorylcholine group-containing monomer with a phosphorylcholine group-free monomer.
  • the phosphorylcholine polymer of the present invention is made of hydrophobic monomers (monomers without phosphorylcholine groups) and hydrophilic monomers (containing phosphorylcholine groups). A polymer formed by a polymerization reaction.
  • the phosphorylcholine polymers of the present invention can be prepared by known methods, or are commercially available.
  • the phosphorylcholine polymer of the present invention also includes the phosphorylcholine polymer prepared by modifying the polymer.
  • the phosphorylcholine polymer (or liposome-like structure) of the present invention contains a phosphorylcholine group represented by formula I (preferably as a group on a branched chain):
  • R 1 , R 2 and R 3 are each independently selected from: H, C 1 -C 4 alkane, C 3 -C 4 cycloalkyl;
  • n 1, 2, 3, or 4.
  • R 1 , R 2 and R 3 are each independently selected from: H, methyl or ethyl.
  • n 2 or 3.
  • the molecular weight of the phosphorylcholine polymer is not particularly limited, and the preferred weight average molecular weight or number average molecular weight is 10,000-3 million, more preferably 50,000-2 million.
  • examples of the phosphorylcholine polymer include (but are not limited to): 2-methacryloyloxyethyl phosphorylcholine homopolymer, 2-methacryloyloxyethyl Copolymers of phosphorylcholine and other hydrophilic and/or hydrophobic monomers or combinations thereof, polyphosphorylcholine ethylene glycol acrylate, polyphosphorylcholine n-butyl methacrylate.
  • the inventors unexpectedly found that when a specific emulsifier is used, the solubility of the oil-insoluble phosphorylcholine polymer can be significantly improved, and the polymer can be well dissolved and dispersed in oil or oily solvent, so that the phosphorylcholine of the present invention can be
  • the alkali polymer oil solution (oily stock solution containing a high concentration of phosphorylcholine polymer compound) obtains high transparency, and has excellent properties such as higher stability and higher biocompatibility, thereby significantly improving the performance of the present invention.
  • the phosphorylcholine polymer content in the cosmetic prepared by the phosphorylcholine polymer oil solution can improve the permeability of the phosphorylcholine polymer and enhance its moisturizing and repairing effects or functions.
  • one or more additional ingredients may also be added, as long as the additional ingredient does not substantially affect the oily stock solution of the present invention (eg, causing a significant decrease in the solubility of the phosphorylcholine polymer, resulting in opacity Wait).
  • additional ingredients are optional, and representative additional ingredients include (but are not limited to): preservatives, fragrances, antioxidants, colors (such as natural colors), fragrances, or other cosmetically acceptable active ingredients (such as ceramides) or excipients.
  • a fragrance can be added to the oily stock solution of the present invention to obtain a predetermined fragrance.
  • a preservative can be added to the oily stock solution of the present invention to further obtain the performance of long-term storage.
  • Representative preservatives are selected from: phenoxyethanol, methyl benzoate, sorbates, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, or combinations thereof.
  • the antioxidant is selected from: tocopherol, tocopherol acetate, tocopherol succinate, tocopherol mixture, or mixtures thereof.
  • the present invention also provides a method for preparing the transparent phosphorylcholine polymer oily stock solution of the present invention.
  • the method includes the steps:
  • step (2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
  • step (3) adding other oils and fats to the mixture described in step (2), and then cooling to 10-60° C. to obtain the phosphorylcholine polymer oily stock solution.
  • the present invention also provides a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
  • Licorice flavonoids are natural compounds extracted from a specific licorice root and have various effects in cosmetic products.
  • Glycyrrhiza flavonoids include glycyrrhizin, glycyrrhizin, aspartame, mannitol, glabridin and the like.
  • Licorice flavonoids have the effect of scavenging oxygen free radicals, and their antioxidant capacity is close to vitamin E and superoxide dismutase (SOD). Licorice flavonoids also have a wide range of biological activities in medicine, such as antibacterial, anti-inflammatory, anti-tumor, anti-HIV, anti-ulcer, anti-arrhythmia, regulating energy consumption and metabolism.
  • SOD superoxide dismutase
  • licorice flavonoids As used herein, “licorice flavonoids”, “licorice flavonoids” are used interchangeably and refer to flavonoids extracted from licorice. It should be understood that the term also includes synthetic or semi-synthetic flavonoids. In addition, the term may include a single licorice flavonoid compound, a mixture of multiple licorice flavonoids, and an extract whose main component is licorice flavonoids.
  • licorice flavonoids include compounds such as flavonoids, dihydroflavonoids, flavonols, isoflavones, chalcones, and diflavonoids.
  • dihydroflavonoids include liquiritigenin, liquiritigenin, new liquiritigenin, liquiritigenin, glabridin, etc.
  • chalcones include isoliquiritigenin, isoliquiritigenin, isoliquiritigenin, new isoliquiritigenin, and the like.
  • Licorice flavonoid is a natural whitening agent extracted from a specific variety of licorice. It can inhibit the activity of tyrosinase, as well as the activity of dopa pigment interconversion and DHICA oxidase. It is a fast, efficient and green whitening and freckle removal agent. Cosmetic additives.
  • Glycyrrhiza flavonoids a compound extracted from licorice, have various effects in cosmetic cosmetics. At the same time, licorice flavonoids also inhibit tyrosinase activity, scavenge oxygen free radicals, and have anti-inflammatory and anti-allergic effects.
  • the preferred licorice flavonoid is glabridin, or a mixture of glabridin and other licorice flavonoids.
  • the invention provides a licorice flavonoid oily stock solution, based on the total weight of the oily stock solution, comprising: 0.1-10% licorice flavonoids, 0.05-10% liposome structural analog, 10-50% oil and 5-50% emulsifier .
  • the licorice flavonoids contain the whitening active ingredient glabridin shown in formula Y1:
  • the licorice flavonoids are encapsulated by liposome structural analogs to form a first encapsulation.
  • the method of the invention improves the solubility of licorice flavonoids in the oily stock solution, so that the content of licorice flavonoids in the cosmetics with oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention increases, thereby enhancing the whitening effect of the cosmetics.
  • the method of the invention improves the stability of the licorice flavonoids in the oily stock solution, so that the licorice flavonoids can be used more widely as active ingredients and can be continuously applied to cosmetics with oil-based, water-in-oil and oil-in-water formulations.
  • the licorice flavonoids are fully dispersed, and will not cause turbidity due to insolubility, thereby enhancing the biocompatibility of cosmetics with oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention .
  • the licorice flavonoid oily stock solution of the present invention has good light transmittance.
  • the particle size of the coating formed by the liposome structural analogue and the licorice flavonoids is molecular level, so that the oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention have In cosmetics, the active ingredients of licorice flavonoids have strong permeability.
  • the licorice flavonoid oil solution of the invention has a wide range of applications, and can be directly used to prepare cosmetics with oil-based, water-in-oil and oil-in-water formulations.
  • ceramide is a type of phospholipid with ceramide as the skeleton, mainly including ceramide phosphorylcholine and ceramide phosphorylethanolamine.
  • the sebum is made up of ceramides, a major part of the intercellular matrix that plays an important role in maintaining the moisture balance of the stratum corneum. Ceramides have a strong ability to associate with water molecules, which maintain skin moisture by forming a network structure in the stratum corneum. Therefore, ceramides have the effect of maintaining skin moisture.
  • Ceramide and cell surface proteins play a role in bonding cells through ester bonds, and this mutual connection is called "lipid-cell-protein" wrapping.
  • Smith et al. have reported that the adhesion between keratinocytes can be judged by measuring the content of ceramide in the stratum corneum of the epidermis. The decrease of the content of ceramide in the stratum corneum of the epidermis can reduce the adhesion between keratinocytes, resulting in dry skin, desquamation, and appearance of keratinocytes. scaly.
  • Pawlmgs et al. studied the mechanism of dry skin desquamation and found that the main reason for skin dryness is the reduction of ceramide content in the epidermis stratum corneum, and the level of ceramide content is directly related to the degree of skin dryness.
  • the use of ceramides can significantly enhance the adhesion between keratinocytes, improve skin dryness and reduce skin desquamation.
  • the moisture content of the skin accounts for about 18% to 20% of the body weight.
  • the moisture and elasticity of the skin are closely related to the moisture contained in the epidermis. Excessive loss of skin moisture can lead to dryness and even chapped skin.
  • Imokawa et al. used organic solvent treatment to remove stratum corneum lipids and found that the skin continued (>4 days) chapped, scaly, and the skin conductivity decreased significantly.
  • lipid fractions extracted from the stratum corneum of the epidermis were subjected to local skin tests under the same conditions to explore which lipid fractions can contribute to the recovery of skin moisture. It was found that the topical application of ceramides resulted in a very significant increase in skin conductivity, followed by cholesterol, and no significant effect of free fatty acids and cholesterol esters.
  • lipid synthesis decreases and the content of ceramides in the stratum corneum decreases.
  • the characteristics of skin aging are: (1) dryness, scaling, roughness, and loss of luster of the skin; (2) thinning of the stratum corneum, increased wrinkles, and decreased elasticity.
  • ceramide can increase the content of ceramide in the epidermis stratum corneum, which can improve skin dryness, desquamation, roughness and other conditions; at the same time, ceramide can increase the thickness of the epidermis stratum corneum, improve the skin's water-holding capacity, reduce wrinkles, enhance skin elasticity, and delay skin aging.
  • Ceramides exist in the cell membranes of animal and plant tissues, and their molecules expose monosaccharide or oligosaccharide residues to the extracellular space and participate in the reaction with the glycolipid head groups of other cells, antibodies, bacterial toxins, and viral envelope proteins. Therefore, ceramides play a very important role in cell adhesion, regulation of cellular immunity, determination of blood group and as tumor antigen.
  • ceramide has been proven to have excellent skin stratum corneum barrier repair function, its solubility in water and oily ingredients is low, and its molecular weight is large, which makes it difficult to directly penetrate into the stratum corneum to repair the skin barrier, which affects its role in skin care. The addition and efficacy of the product.
  • the invention provides a ceramide oily stock solution, which, based on the total weight of the oily stock solution, comprises: 0.1-10% ceramide, 0.05-10% liposome-like structure, 0.1-50% oil, 1-45% emulsifier .
  • the ceramide is a compound represented by formula Y2:
  • R 1 is selected from: C 40-50 alkyl, C 40-50 alkenyl, C 40-50 alkynyl;
  • C 40-50 alkyl group, C 40-50 alkenyl group, C 40-50 alkynyl group all include: ester group, heteroaryl group, aryl group and combinations thereof;
  • R 2 is selected from: C 11-21 alkyl, C 11-21 alkenyl, C 11-21 alkyl containing hydroxyl, C 11-21 alkenyl containing hydroxyl, or combinations thereof.
  • the ceramide is selected from the group consisting of: ceramide 1 [EOS], ceramide 2 [NS], ceramide 3 [NP], ceramide 4 [EOS], ceramide 5 [AS], ceramide 6[NH], ceramide 6II, ceramide 7 [AP], ceramide 8 [AH], ceramide 9 [EOP], ceramide E, or a combination thereof;
  • the ceramide is encapsulated by a liposome structural analog to form a first encapsulation.
  • the method of the invention improves the solubility of ceramides in the oily stock solution, so that the content of ceramides in cosmetics with oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention increases, thereby enhancing the whitening effect of the cosmetics.
  • the ceramide oil solution of the invention has good stability, and the water-oil-insoluble ceramide oily stock solution system prepared by the method of the invention is uniform and stable, which is beneficial to the compatibility stability of the end product.
  • the ceramide oily stock solution prepared according to the preparation method of the present invention has improved transdermal permeability and more remarkable efficacy.
  • the ceramide oil solution of the present invention has a wide range of applications, and the water-oil-insoluble ceramide oil solution of the present invention can be used to prepare cream-like cosmetics with oil-based formulations, and can directly prepare oil-based, water-in-oil, and oil-in-water formulations of cosmetics.
  • glycyrrhizic acid exists in licorice in the form of potassium salt or calcium salt, and dipotassium glycyrrhizate is a natural product, and glycyrrhizic acid is extracted and separated from licorice as a raw material to obtain derivatives of glycyrrhizic acid.
  • dipotassium glycyrrhizinate is to extract glycyrrhizic acid from licorice as a raw material, pass ammonia to generate monoammonium glycyrrhizinate, and then generate dipotassium glycyrrhizinate through ion exchange.
  • monopotassium salt and dipotassium salt are mostly used in medicine and cosmetics due to their pharmaceutical standards, high degree of purification, and good quality stability of products available in the market.
  • dipotassium glycyrrhizate can penetrate deep into the skin and maintain high activity, whitening and high-efficiency anti-oxidation, effectively inhibiting the activity of various enzymes in the process of melanin production, especially inhibiting the activity of tyrosinase, while also preventing rough skin and Anti-inflammatory and antibacterial effects.
  • dipotassium glycyrrhizate also has great potential application value in skin repair.
  • the invention provides an oily stock solution of dipotassium glycyrrhizinate, which, based on the total weight of the oily stock solution, comprises: 0.1-10% dipotassium glycyrrhizinate, 0.05-10% liposome structural analog, 10-50% oil and 5- 50% emulsifier.
  • the dipotassium glycyrrhizinate contains the whitening active ingredient shown in formula Y3:
  • the dipotassium glycyrrhizinate is encapsulated by a liposome structural analog to form a first encapsulation.
  • the liposome structural analog contains (a) a hydrophilic group; (b) a hydrophobic group.
  • the hydrophilic group contains a branched chain structure shown in formula I:
  • R1, R2 and R3 are each independently selected from: H, C1-C4 alkane, C3-C4 cycloalkyl;
  • hydrophobic group comprises: C5-30 aliphatic chain structure.
  • the method of the present invention improves the solubility of dipotassium glycyrrhizinate in the oily stock solution, so that the content of dipotassium glycyrrhizate in the cosmetics of oil-based, water-in-oil, and oil-in-water formulations prepared with the oily stock solution of the present invention increases, thereby enhancing the cosmetic whitening effect.
  • the method of the invention improves the stability of dipotassium glycyrrhizinate in the oily stock solution, so that dipotassium glycyrrhizate can be used more widely as an active ingredient, and can be continuously applied to cosmetics with oil-based, water-in-oil and oil-in-water formulations.
  • the dipotassium glycyrrhizate of the present invention is fully dispersed, and will not cause turbidity due to insolubility, thereby enhancing the cosmetic properties of oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention. Biocompatibility.
  • the dipotassium glycyrrhizate oily stock solution of the present invention has good light transmittance.
  • the particle size of the coating formed by the liposome structural analog and dipotassium glycyrrhizinate is molecular level, so that the oil-based, water-in-oil and oil-in-water formulations prepared with the oily stock solution of the present invention have In cosmetics, the active ingredient of dipotassium glycyrrhizinate has strong permeability.
  • the dipotassium glycyrrhizate oily stock solution of the present invention has a wide range of applications, and can be directly used for the preparation of cosmetics with oil-based, water-in-oil and oil-in-water formulations.
  • the present invention also provides a preparation method of a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
  • the present invention provides a method for preparing a phosphorylcholine polymer oily stock solution, the method comprising the steps of:
  • step (2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
  • step (3) adding other oils and fats to the mixture described in step (2), and then cooling to 10-60° C. to obtain the phosphorylcholine polymer oily stock solution.
  • the present invention provides a method for licorice flavonoids stock solution, the method comprises the steps:
  • (a1) provide licorice flavonoids, liposome structural analogs and emulsifiers, and mix them into an oil phase mixture according to a certain proportion;
  • step (a2) heating the oil phase mixture in step (a1) (eg, 45-120° C.) to form a heated mixture;
  • step (a3) adding grease to the mixture described in step (a2), then cooling down (such as cooling to 20-80°C, preferably 20-45°C) to obtain the glycyrrhizin oily stock solution of cooling;
  • the present invention provides a method for a ceramide stock solution, the method comprising the steps:
  • (b1) provide ceramide, liposome-like structure and oil, and mix them into oil phase mixture according to a certain proportion
  • step (b2) heating the oil phase mixture in step (b1) to 45-120°C;
  • step (b3) adding an emulsifier to the mixture described in step (b2), then cooling to 20-80° C., preferably 20-45° C., to obtain an oil-phase mixture to obtain the ceramide oily stock solution;
  • the invention provides a method for a stock solution of dipotassium glycyrrhizinate, the method comprising the steps:
  • (c1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
  • step (c2) heating the oil phase mixture in step (c1), thereby forming a heated mixture
  • step (c3) adding grease to the mixture described in step (c2), and then cooling down to obtain the oily stock solution of dipotassium glycyrrhizinate is the oily stock solution of dipotassium glycyrrhizinate.
  • the method of the present invention improves the solubility of the phosphorylcholine polymer in the oily stock solution, so that the content of the phosphorylcholine polymer in the oil-based, water-in-oil, and oil-in-water cosmetics prepared with the oily stock solution of the present invention is 100% high, thereby enhancing the moisturizing and repairing effect of cosmetics.
  • the method of the present invention improves the stability of the phosphorylcholine polymer in the oily stock solution, so that the phosphorylcholine polymer can be used more widely as an active ingredient, and can be continuously applied in oil-based, water-in-oil, water-in-water in oil cosmetics.
  • the phosphorylcholine polymer is fully dispersed, and will not cause turbidity due to insolubility, thereby enhancing the oil-based, water-in-oil, and oil-in-water formula cosmetics prepared with the oily stock solution of the present invention. Biocompatibility.
  • the phosphorylcholine polymer oily stock solution of the present invention has good light transmittance.
  • the phosphorylcholine polymer and the emulsifier are fully mixed to form a complex, so that the oil-based, water-in-oil and oil-in-water formula cosmetics prepared with the oily stock solution of the present invention, phosphoryl Choline polymers have good film-forming properties, and have good moisturizing and anti-irritant properties.
  • step (2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
  • step (3) Add other oils and fats to the mixture in step (2), and then cool down to 10-60° C. to obtain the phosphorylcholine polymer oily stock solution No. 1 (100 g in total).
  • Example 1 was repeated, except that the components were weighed according to the raw material ratios of Example 2 shown in Table 1, thereby obtaining phosphorylcholine oily stock solution No.2.
  • Example 1 was repeated, except that the components were weighed in accordance with the raw material ratios of Comparative Example 1 shown in Table 1, thereby obtaining phosphorylcholine oily stock solution No. C1.
  • Test method room temperature, take photos, and compare the transparency with the naked eye.
  • Embodiment 1 the appearance is transparent (Fig. 1);
  • Embodiment 2 the appearance is transparent
  • Comparative example 1 cloudy appearance (Fig. 2)
  • Test method put the sample at room temperature for 1 month; cycle at 45°C (24h at 45°C, return to room temperature for 24h, cycle for 1 month); observe at 5°C for 1 month, observe at -10°C for 1 month, and compare the transparency with the naked eye.
  • Example 1 Example 2 Comparative Example 1 Room temperature (25°C) 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 45°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 5°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated -10°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated
  • step (3) adding oil to the mixture described in step (2), then cooling to 20-80°C, preferably 20-45°C, to obtain an oil-phase mixture; No. 1 (100 g in total).
  • Example 4 was repeated, except that the components were weighed according to the raw material ratios of Example 5 shown in Table 3, so as to obtain the licorice flavonoid oily stock solution No.2.
  • Example 4 was repeated, with the difference that the components were weighed according to the raw material ratios of Comparative Example 2 shown in Table 3, so as to obtain the licorice flavonoid mixed solution No. C1.
  • Test method room temperature, take photos, and compare the transparency with the naked eye.
  • Embodiment 4 the appearance is transparent (Fig. 3);
  • Embodiment 5 the appearance is transparent
  • Test method put the sample at room temperature for 1 month; cycle at 45°C (24h at 45°C, return to room temperature for 24h, cycle for 1 month); observe at 5°C for 1 month, observe at -10°C for 1 month, and compare the transparency with the naked eye.
  • Example 4 Comparative Example 2 Room temperature (20°C) 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 45°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 5°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated -10°C, 1 month The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated
  • step (3) Add an emulsifier to the mixture described in step (2), then cool down to 20-80° C., add an antioxidant, and obtain the ceramide oil solution No. 1, with a total weight of 100 g.
  • Example 7 was repeated, except that the components were weighed according to the raw material ratios of Example 8 shown in Table 5, so as to obtain ceramide oily stock solution No. 2.
  • Example 7 was repeated, except that the components were weighed in accordance with the raw material ratios of Example 9 shown in Table 5, so as to obtain ceramide oily stock solution No. 3.
  • Example 7 was repeated, except that the components were weighed according to the raw material ratios of Comparative Example 3 shown in Table 5, so as to obtain the ceramide mixed solution No. C1.
  • Test method room temperature, take photos, and compare the transparency with the naked eye.
  • Embodiment 7 the appearance is transparent (Fig. 5);
  • Embodiment 8 the appearance is transparent
  • Embodiment 9 the appearance is transparent
  • Test method put the sample at room temperature for 1 month; cycle at 45°C (24h at 45°C, return to room temperature for 24h, cycle for 1 month); observe at 5°C for 1 month, observe at -10°C for 1 month, and compare the transparency with the naked eye.
  • Example 7 Example 8 Example 9 Comparative Example 3 Room temperature (20°C) 1 month The appearance remains transparent The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 45°C, 1 month The appearance remains transparent The appearance remains transparent The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated 5°C, 1 month The appearance remains transparent The appearance remains transparent The appearance remains transparent Appearance appears to be precipitated -10°C The appearance remains transparent The appearance remains transparent The appearance remains transparent Precipitation in appearance
  • step (3) adding oil to the mixture described in step (2), then cooling to 20-80°C, preferably 20-45°C, to obtain an oil-phase mixture; No. 1 (100 g in total).
  • Example 11 was repeated, except that the components were weighed in accordance with the raw material ratios of Example 12 shown in Table 7, so as to obtain dipotassium glycyrrhizinate oily stock solution No.2.
  • Example 11 was repeated, except that the components were weighed in accordance with the raw material ratios of Comparative Example 4 shown in Table 7, thereby obtaining the dipotassium glycyrrhizinate mixed solution No. C1.
  • Test method room temperature, take photos, and compare the transparency with the naked eye.
  • Embodiment 11 the appearance is transparent (Fig. 7);
  • Embodiment 12 the appearance is transparent
  • Test method put the sample at room temperature for 1 month; cycle at 45°C (24h at 45°C, return to room temperature for 24h, cycle for 1 month); observe at 5°C for 1 month, observe at -10°C for 1 month, and compare the transparency with the naked eye.

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Abstract

La présente invention concerne une solution huileuse limpide d'un polymère de phosphorylcholine, une solution mère de matière première cosmétique, et leur procédé de préparation. Spécifiquement, la présente invention concerne une solution huileuse limpide d'un polymère de phosphorylcholine contenant le polymère de phosphorylcholine, un émulsifiant et de la graisse, et son procédé de préparation. Sous l'action d'un monomère hydrophobe et d'un monomère hydrophile dans la structure polymère de phosphorylcholine, le polymère de phosphorylcholine est dissous dans un émulsifiant spécifique et dispersé dans une solution huileuse pour former une solution limpide; l'application du polymère de phosphorylcholine dans des formulations à base d'huile, eau-dans-huile et huile-dans-eau de produits cosmétiques est augmentée, et la propriété de formation de film de celui-ci est utilisée, ce qui permet de réduire les irritations et d'améliorer la stabilité et l'effet hydratant. La présente invention concerne en outre des solutions mères de matière première cosmétique correspondantes, telles qu'une solution mère huileuse de licoflavone, une solution mère huileuse de céramide, et une solution mère huileuse de glycyrrhizinate de dipotassium.
PCT/CN2022/075196 2021-02-02 2022-01-30 Solution huileuse limpide de polymère de phosphorylcholine, solution mère de matière première cosmétique, leur procédé de préparation et leur application WO2022166926A1 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
CN202110146125.5A CN112741781A (zh) 2021-02-02 2021-02-02 水油不溶性甘草黄酮的透明油溶液及其制法和应用
CN202110146125.5 2021-02-02
CN202110168629.7 2021-02-07
CN202110179830.5 2021-02-07
CN202110168629.7A CN112891248A (zh) 2021-02-07 2021-02-07 一种水油不溶性神经酰胺透明油溶液及其制备方法
CN202110179830.5A CN113181080A (zh) 2021-02-07 2021-02-07 磷酰胆碱聚合物的透明油溶液及其制法和应用
CN202110298003.8A CN112915041A (zh) 2021-03-19 2021-03-19 油不溶性甘草酸二钾的透明油溶液及其制法和应用
CN202110298003.8 2021-03-19

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Citations (9)

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JP2002356519A (ja) * 2001-05-30 2002-12-13 Nof Corp ホスホリルコリン類似基含有重合体および用途
JP2007099654A (ja) * 2005-10-03 2007-04-19 Pola Chem Ind Inc 保湿用の化粧料セット
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WO2012099384A2 (fr) * 2011-01-20 2012-07-26 주식회사 케이씨아이 Copolymère réticulé à base de monomères contenant un groupe de type phosphorylcholine, émulsion inverse, et composition cosmétique
CN111803393A (zh) * 2020-08-03 2020-10-23 上海奥利实业有限公司 水油不溶性甘草黄酮的透明水溶液及其制法和应用
CN112741781A (zh) * 2021-02-02 2021-05-04 上海奥利实业有限公司 水油不溶性甘草黄酮的透明油溶液及其制法和应用
CN112891248A (zh) * 2021-02-07 2021-06-04 上海奥利实业有限公司 一种水油不溶性神经酰胺透明油溶液及其制备方法
CN112921504A (zh) * 2021-01-21 2021-06-08 张应冲 一种作用于一次性医护无纺布快速喷绒成型机构
CN113181080A (zh) * 2021-02-07 2021-07-30 上海奥利实业有限公司 磷酰胆碱聚合物的透明油溶液及其制法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002356519A (ja) * 2001-05-30 2002-12-13 Nof Corp ホスホリルコリン類似基含有重合体および用途
JP2007099654A (ja) * 2005-10-03 2007-04-19 Pola Chem Ind Inc 保湿用の化粧料セット
JP2010043021A (ja) * 2008-08-12 2010-02-25 Pola Chem Ind Inc 保湿化粧料
WO2012099384A2 (fr) * 2011-01-20 2012-07-26 주식회사 케이씨아이 Copolymère réticulé à base de monomères contenant un groupe de type phosphorylcholine, émulsion inverse, et composition cosmétique
CN111803393A (zh) * 2020-08-03 2020-10-23 上海奥利实业有限公司 水油不溶性甘草黄酮的透明水溶液及其制法和应用
CN112921504A (zh) * 2021-01-21 2021-06-08 张应冲 一种作用于一次性医护无纺布快速喷绒成型机构
CN112741781A (zh) * 2021-02-02 2021-05-04 上海奥利实业有限公司 水油不溶性甘草黄酮的透明油溶液及其制法和应用
CN112891248A (zh) * 2021-02-07 2021-06-04 上海奥利实业有限公司 一种水油不溶性神经酰胺透明油溶液及其制备方法
CN113181080A (zh) * 2021-02-07 2021-07-30 上海奥利实业有限公司 磷酰胆碱聚合物的透明油溶液及其制法和应用

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