WO2022166926A1 - Clear oily solution of phosphorylcholine polymer, cosmetic raw material stock solution, and preparation method therefor and application thereof - Google Patents

Clear oily solution of phosphorylcholine polymer, cosmetic raw material stock solution, and preparation method therefor and application thereof 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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French (fr)
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/en
Priority claimed from CN202110179830.5A external-priority patent/CN113181080A/en
Priority claimed from CN202110168629.7A external-priority patent/CN112891248A/en
Priority claimed from CN202110298003.8A external-priority patent/CN112915041A/en
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/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90Block copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations 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.

Abstract

The present invention provides a clear oily solution of a phosphorylcholine polymer, a cosmetic raw material stock solution, and a preparation method therefor. Specifically, the present invention provides a clear oily solution of a phosphorylcholine polymer containing the phosphorylcholine polymer, an emulsifier, and grease, and a preparation method therefor. Under the action of a hydrophobic monomer and a hydrophilic monomer in the phosphorylcholine polymer structure, the phosphorylcholine polymer is dissolved in a specific emulsifier and dispersed in an oily solution to form a clear solution; the application of the phosphorylcholine polymer in oil-based, water-in-oil, and oil-in-water formulations of cosmetics is increased, and the film-forming property thereof is used, thereby reducing irritations and improving the stability and the moisturizing effect. The present invention further provides corresponding cosmetic raw material stock solutions such as a licoflavone oily stock solution, a ceramide oily stock solution, and a dipotassium glycyrrhizinate oily stock solution.

Description

<磷酰胆碱聚合物的透明油溶液和化妆品原料原液及其制法和应用><Transparent oil solution of phosphorylcholine polymer and cosmetic raw material stock solution and its production method and application> 技术领域technical field
本发明涉及化妆品原料领域,具体地涉及油不溶性磷酰胆碱聚合物的透明油溶液和化妆品原料原液及其制法和应用。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.
背景技术Background technique
近年来随着环境的恶化,大气颗粒污染、紫外线、水质量的影响,对人体的皮肤造成了损害。同时,随着生活中工作中面临的焦虑、压力、熬夜等不良生活方式,以及饮食方式不够健康,一系列的因素造成了皮肤的亚健康状态。化妆品成为男女老少生活中必备的消耗品,随着人们认知的提高,对化妆品的性能有了更高的要求,而化妆品性能的提升和其中原料密不可分。In recent years, with the deterioration of the environment, the effects of atmospheric particle pollution, ultraviolet rays, and water quality have caused damage to human skin. At the same time, with the anxiety, stress, staying up late and other unhealthy lifestyles in life and work, as well as unhealthy eating patterns, a series of factors have caused the sub-health state of the skin. Cosmetics have become necessary consumables in the lives of men, women and children. With the improvement of people's cognition, there are higher requirements for the performance of cosmetics, and the improvement of cosmetic performance is inseparable from the raw materials.
近年来磷酰胆碱聚合物作为一种生物相容性良好的仿生生物材料异军突起,这种高端医学仿生材料具有高度的生物相容性,主要应用于生物医药,医疗器械领域,并且已经在高档化妆品的作为保湿原料使用。二十世纪末,日本油脂株式会社开发出仿生磷酰胆碱系列产品,由于其极高的保湿透气性能和与人体细胞膜极其相似的成分及特性,被誉为人造细胞膜。其中以聚季铵盐-51为代表的磷酰胆碱聚合物(人造细胞膜)逐渐走进人们的视野,通过2-甲基丙烯酰氧乙基磷酰胆碱(MPC)与不同疏水性烷基链聚合,及调节不同聚合比例,实现产品性能的变化,应用到不同领域。其具有极好的组织相容性和血液相容性,常用于医学器官移植、眼科护理、创伤修复等生物医学领域。In recent years, 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. At the end of the 20th century, 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. Among them, 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.
在化妆品中应用,可以在皮肤表面形成一层可以呼吸的生物膜形成透气保水薄膜,智慧锁水保湿,具有超强保湿性,其保湿性能是透明质酸的两倍,同时抑制成品中刺激物对皮肤的刺激,屏蔽环境中的粉尘吸附稳定电荷层,消除静电。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.
另外聚季铵盐-51形成优异的耐水洗薄膜,具有分子钉效应,即在多次水洗后仍保持在皮肤表面,长效保湿并降低刺激。目前由于磷酰胆碱的自身特性,多用于水基的产品,从而限制其应用。In addition, 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. At present, due to its own characteristics, phosphorylcholine is mostly used in water-based products, which limits its application.
因此,本领域迫切需要开发适用于油基、水包油、油包水等多种剂型的高透明度、高稳定性、高生物相容性的磷酰胆碱聚合物油溶液。Therefore, there is an urgent need in the art to develop a phosphorylcholine polymer oil solution with high transparency, high stability and high biocompatibility suitable for oil-based, oil-in-water, water-in-oil and other dosage forms.
发明内容SUMMARY OF THE INVENTION
本发明的目的在于提供一种适用于化妆品的高透明度、高稳定性和高生物相容性的磷酰胆碱聚合物油溶液(原液)及其制法和用途。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.
在本发明的第一方面,提供了一种磷酰胆碱聚合物油性原液,以油性原液总重计,包含:0.1-10%磷酰胆碱聚合物、5-50%乳化剂、和5-50%油脂。In a first aspect of the present invention, there is provided 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.
在另一优选例中,所述的油性原液还含有0.1-5%抗氧化剂。In another preferred example, the oily stock solution also contains 0.1-5% antioxidant.
在另一优选例中,所述抗氧化剂选自:生育酚、生育酚醋酸酯、生育酚琥珀酸酯、生育酚混合物、或其混合物。In another preferred example, the antioxidant is selected from: tocopherol, tocopherol acetate, tocopherol succinate, tocopherol mixture, or a mixture thereof.
在另一优选例中,所述磷酰胆碱聚合物含有(a)亲水性基团;(b)疏水性基团。In another preferred embodiment, the phosphorylcholine polymer contains (a) a hydrophilic group; (b) a hydrophobic group.
在另一优选例中,所述亲水性基团含有式I所示支链结构:In another preferred example, the hydrophilic group contains a branched chain structure shown in formula I:
Figure PCTCN2022075196-appb-000001
Figure PCTCN2022075196-appb-000001
式中,R 1,R 2和R 3各自独立地选自:H、C 1-C 4烷烃基、C 3-C 4的环烷基。 In the formula, R 1 , R 2 and R 3 are each independently selected from: H, C 1 -C 4 alkane, and C 3 -C 4 cycloalkyl.
在另一优选例中,所述磷酰胆碱聚合物的主链单元选自下组:In another preferred embodiment, the main chain unit of the phosphorylcholine polymer is selected from the following group:
A1)
Figure PCTCN2022075196-appb-000002
A1)
Figure PCTCN2022075196-appb-000002
A2)
Figure PCTCN2022075196-appb-000003
A2)
Figure PCTCN2022075196-appb-000003
A3)
Figure PCTCN2022075196-appb-000004
A3)
Figure PCTCN2022075196-appb-000004
A4)
Figure PCTCN2022075196-appb-000005
A4)
Figure PCTCN2022075196-appb-000005
A5)A1-A4组合。A5) A1-A4 combination.
在另一优选例中,在A1~A5中,式I所示的磷酰胆碱基团通过-CO-O-CH 2-CH 2-、-CO-O-CH 2-CH 2-O-、和/或-CO-O-(CH 2)m-CH 2-连接于主链,其中m为2-17的正整数。 In another preferred example, in A1-A5, 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.
在另一优选例中,所述的主链选自下组:
Figure PCTCN2022075196-appb-000006
In another preferred embodiment, the main chain is selected from the following group:
Figure PCTCN2022075196-appb-000006
or
Figure PCTCN2022075196-appb-000007
Figure PCTCN2022075196-appb-000007
在另一优选例中,所述磷酰胆碱聚合物选自:2-甲基丙烯酰氧乙基磷酰胆碱均聚物、2-甲基丙烯酰氧乙基磷酰胆碱和其他亲水性和/或疏水性单体的共聚物或其组合、聚磷酸胆碱乙二醇丙烯酸酯、聚磷酸胆碱甲基丙烯酸正丁酯、或其组合。In another preferred embodiment, 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.
在另一优选例中,所述油脂选自:棕榈酸异丙酯、棕榈酸异辛酯、异壬酸异壬酯、白油、甘油辛酸酯/癸酸三酯、辛基十二烷醇、椰油酸、月桂醇、肉豆蔻酸异丙酯、乳木果油、12-羟基硬脂酸异辛酯、苹果酸二异硬脂醇酯、角鲨烷、霍霍巴油、大豆油、橄榄油、甜杏仁油、鳄梨油、小麦胚芽油或其组合。In another preferred example, 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.
在另一优选例中,所述乳化剂选自:聚甘油酯类、失水山梨醇脂肪酸酯系列、山梨醇椰油酸酯、蔗糖脂肪酸酯、烷基糖苷类、氢化卵磷脂、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚醚类、甘油辛酸/癸酸酯或其组合。In another preferred example, 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.
在本发明的第二方面,提供了一种制备第一方面所述磷酰胆碱聚合物油性原液的方法,包括步骤:In the second aspect of the present invention, there is provided a method for preparing the phosphorylcholine polymer oily stock solution described in the first aspect, comprising the steps of:
(1)提供磷酰胆碱聚合物、乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide phosphorylcholine polymer and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃,较佳地60-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
(3)将其他油脂加入至步骤(2)所述混合料中,随后降温至10-60℃而获得所述磷酰胆碱聚合物油性原液。(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.
在本发明的第三方面,提供了一种第一方面所述的磷酰胆碱聚合物油性原液的用途,用于制造油基、油包水、水包油配方化妆品。In a third aspect of the present invention, 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.
在本发明的第四方面,提供了一种化妆品,含有第一方面所述的磷酰胆碱聚合物油性原液。In the fourth aspect of the present invention, there is provided a cosmetic, which contains the phosphorylcholine polymer oily stock solution described in the first aspect.
在另一优选例中,所述的化妆品为油基配方的化妆品或含有油性辅料。In another preferred example, the cosmetic is an oil-based cosmetic or contains an oily auxiliary.
在另一优选例中,所述油基化妆品包括:面贴膜、喷雾、湿巾、乳液、膏霜、美容液、凝胶、洗发水、护发素、头发及头皮护理精华液、彩妆或其他用于皮肤和头发的美容化妆品、或其组合。In another preferred embodiment, 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.
在本发明的第五方面,提供了一种化妆品原料原液,所述的化妆品原料原液选 自下组:In the fifth aspect of the present invention, a kind of cosmetic raw material stock solution is provided, and the described cosmetic raw material stock solution is selected from the following group:
(Y1)甘草黄酮油性原液,以油性原液总重计,包含:0.1-10%甘草黄酮、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂;(Y1) Glycyrrhiza flavonoids oily 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% oils and fats and 5-50% emulsifiers;
(Y2)神经酰胺油性原液,以油性原液总重计,包含:0.1~10%神经酰胺、0.05~10%脂质体类似结构物、0.1~50%油脂、1~45%乳化剂;和(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)甘草酸二钾油性原液,以油性原液总重计,包含:0.1-10%甘草酸二钾、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。(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.
在另一优选例中,所述原液为甘草黄酮油性原液,以油性原液总重计,包含:0.1-10%甘草黄酮、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。In another preferred example, 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.
在另一优选例中,所述甘草黄酮含有式Y1所示的美白活性成分光甘草定:In another preferred example, the licorice flavonoids contain the whitening active ingredient glabridin represented by formula Y1:
Figure PCTCN2022075196-appb-000008
Figure PCTCN2022075196-appb-000008
在另一优选例中,所述甘草黄酮被脂质体结构类似物包裹,形成第一包覆物。In another preferred embodiment, the licorice flavonoids are encapsulated by liposome structural analogs to form a first encapsulation.
在另一优选例中,所述原液为神经酰胺油性原液,以油性原液总重计,包含:0.1~10%神经酰胺、0.05~10%脂质体类似结构物、0.1~50%油脂、1~45%乳化剂。In another preferred example, 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.
在另一优选例中,所述神经酰胺为式Y2所示的化合物:In another preferred embodiment, the ceramide is a compound represented by formula Y2:
Figure PCTCN2022075196-appb-000009
Figure PCTCN2022075196-appb-000009
式中,In the formula,
R 1选自:C 40-50烷基、C 40-50烯基、C 40-50炔基; R 1 is selected from: C 40-50 alkyl, C 40-50 alkenyl, C 40-50 alkynyl;
其中所述C 40-50烷基、C 40-50烯基、C 40-50炔基均包含:酯基、杂芳基、芳基及其组合; Wherein the 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选自:C 11-21烷基、C 11-21烯基、含有羟基的C 11-21烷基、含有羟基的C 11-21烯基、或其组合。 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.
在另一优选例中,所述神经酰胺选自:经酰胺1[EOS]、神经酰胺2[NS]、神经酰胺3[NP]、神经酰胺4[EOS]、神经酰胺5[AS]、神经酰胺6[NH]、神经酰胺6II、神经酰胺7[AP]、神经酰胺8[AH]、神经酰胺9[EOP]、神经酰胺E或其组合;In another preferred example, 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;
其中,不同神经酰胺结构如下:Among them, different ceramide structures are as follows:
Figure PCTCN2022075196-appb-000010
Figure PCTCN2022075196-appb-000010
在另一优选例中,所述神经酰胺被脂质体结构类似物包裹,形成第一包覆物。In another preferred embodiment, the ceramide is encapsulated by a liposome structural analog to form a first encapsulation.
在另一优选例中,所述原液为甘草酸二钾油性原液,以油性原液总重计,包含:0.1-10%甘草酸二钾、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。In another preferred example, 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.
在另一优选例中,所述甘草酸二钾含有式Y3所示的美白活性成分:In another preferred example, the dipotassium glycyrrhizinate contains the whitening active ingredient shown in formula Y3:
Figure PCTCN2022075196-appb-000011
Figure PCTCN2022075196-appb-000011
在另一优选例中,所述甘草酸二钾被脂质体结构类似物包裹,形成第一包覆物。In another preferred embodiment, the dipotassium glycyrrhizinate is encapsulated by a liposome structural analog to form a first encapsulation.
在另一优选例中,所述脂质体结构类似物含有(a)亲水性基团;(b)疏水性基团。In another preferred example, the liposome structural analog contains (a) a hydrophilic group; (b) a hydrophobic group.
在另一优选例中,所述亲水性基团含有式I所示支链结构:In another preferred example, the hydrophilic group contains a branched chain structure shown in formula I:
Figure PCTCN2022075196-appb-000012
Figure PCTCN2022075196-appb-000012
式中,R1,R2和R3各自独立地选自:H、C1-C4烷烃基、C3-C4的环烷基;In the formula, R1, R2 and R3 are each independently selected from: H, C1-C4 alkane, C3-C4 cycloalkyl;
其中所述疏水性基团包含:C5-30脂肪链结构。Wherein the hydrophobic group comprises: C5-30 aliphatic chain structure.
在另一优选例中,所述油脂选自:棕榈酸异丙酯、棕榈酸异辛酯、异壬酸异壬酯、白油、甘油辛酸酯/癸酸三酯、辛基十二烷醇、椰油酸、月桂醇、肉豆蔻酸异丙酯、乳木果油、12-羟基硬脂酸异辛酯、苹果酸二异硬脂醇酯、角鲨烷、霍霍巴油、大豆油、橄榄油、甜杏仁油、鳄梨油、小麦胚芽油或其组合。In another preferred example, 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.
在另一优选例中,所述乳化剂选自:聚甘油酯类、失水山梨醇脂肪酸酯系列、山梨醇椰油酸酯、蔗糖脂肪酸酯、烷基糖苷类、氢化卵磷脂、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚醚类、甘油辛酸/癸酸酯或其组合。In another preferred example, 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.
在本发明的第六方面,提供了一种制备本发明第五方面所述的化妆品原料原液的方法,所述方法包括步骤:In the sixth aspect of the present invention, a method for preparing the cosmetic raw material stock solution described in the fifth aspect of the present invention is provided, the method comprising the steps of:
(a1)提供甘草黄酮、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(a1) provide licorice flavonoids, liposome structural analogs and emulsifiers, and mix them into an oil phase mixture according to a certain proportion;
(a2)将步骤(a1)中的油相混合料加热(如45-120℃),从而形成加热的混合料;(a2) heating the oil phase mixture in step (a1) (eg, 45-120° C.) to form a heated mixture;
(a3)将油脂加入至步骤(a2)所述混合料中,随后降温(如降温至20-80℃,优选地20-45℃)而获得降温的得到所述甘草黄酮油性原液;(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;
或所述方法包括步骤:or the method comprises the steps:
(b1)提供神经酰胺、脂质体类似结构物和油脂,并将它们按照一定比例混合成油相混合料;(b1) provide ceramide, liposome-like structure and oil, and mix them into oil phase mixture according to a certain proportion;
(b2)将步骤(b1)中的油相混合料加热至45-120℃;(b2) heating the oil phase mixture in step (b1) to 45-120°C;
(b3)将乳化剂加入至步骤(b2)所述混合料中,随后降温至20-80℃,优选地20-45℃而获油相混合料,得到所述的神经酰胺油性原液;(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;
或所述方法包括步骤:or the method comprises the steps:
(c1)提供甘草酸二钾、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(c1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(c2)将步骤(c1)中的油相混合料加热,从而形成加热的混合料;(c2) heating the oil phase mixture in step (c1), thereby forming a heated mixture;
(c3)将油脂加入至步骤(c2)所述混合料中,随后降温而获得降温的得到所述甘草酸二钾油性原液即为所述甘草酸二钾油性原液。(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.
在本发明的第七方面,提供了本发明第五方面所述的原料原液的用途,用于制备油基、油包水、水包油配方的化妆品。In the seventh aspect of the present invention, there is provided the use of 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.
在本发明的第八方面,提供了一种化妆品,它含有本发明第五方面所述的原料原液。In the eighth aspect of the present invention, there is provided a cosmetic product, which contains the raw material solution according to the fifth aspect of the present invention.
应理解,在本发明范围内中,本发明的上述各技术特征和在下文(如实施例)中具体描述的各技术特征之间都可以互相组合,从而构成新的或优选的技术方案。限于篇幅,在此不再一一累述。It should be understood that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features specifically described in the following (eg, the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, it is not repeated here.
附图说明Description of drawings
图1显示了本发明一个实施例中制备的透明的磷酰胆碱聚合物油性原液。Figure 1 shows a transparent phosphorylcholine polymer oily stock solution prepared in one example of the present invention.
图2显示了现有技术中磷酰胆碱聚合物与油形成的混合液(混浊液)。Figure 2 shows the mixed solution (cloudy solution) of phosphorylcholine polymer and oil in the prior art.
图3显示了本发明一个实施例中制备的透明的甘草黄酮油性原液。Figure 3 shows the transparent licorice flavonoid oily stock solution prepared in one example of the present invention.
图4显示了现有技术中甘草黄酮与油形成的混合液(乳浊液)。Figure 4 shows the prior art mixture (emulsion) of licorice flavonoids and oil.
图5显示了本发明一个实施例中制备的透明的神经酰胺油性原液。Figure 5 shows a transparent ceramide oily stock solution prepared in one example of the present invention.
图6显示了现有技术中神经酰胺与油形成的混合液(析出液)。Fig. 6 shows the mixed solution (precipitate) formed by ceramide and oil in the prior art.
图7显示了本发明一个实施例中制备的透明的甘草酸二钾油性原液。Figure 7 shows a transparent dipotassium glycyrrhizinate oily stock solution prepared in one example of the present invention.
图8显示了现有技术中甘草酸二钾与油形成的混合液(悬浊液)。Figure 8 shows the prior art mixture (suspension) of dipotassium glycyrrhizate and oil.
具体实施方式Detailed ways
本发明人经过广泛而深入的研究,通过大量筛选,首次意外地开发了一种高稳定、高相容性和透明的磷酰胆碱聚合物油性原液(oily stock solution)。具体地,本发明人通过添加特定成分(磷酰胆碱聚合物乳化剂和油脂),从而获得一种具有高透明度、高稳定性、高生物相容性的油性原液。本发明的高透明度的油性原液,可广泛地应用在化妆品中,从而提高化妆品的品质和效果。在此基础上完成了本发明。After extensive and in-depth research and extensive screening, 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.
具体地,本发明的磷酰胆碱聚合物油溶液(也称为“油性原液”),利用磷酰胆 碱聚合物结构中疏水性侧链基团(或单体)和亲水性侧链基团(或单体),将其溶解在特定乳化剂中,使得磷酰胆碱聚合物在油基、油包水、水包油配方的化妆品中的溶解性能得以显著改善,而获得了高透明度、高稳定性、高生物相容性的油性原液。Specifically, 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.
本发明的透明的磷酰胆碱聚合物油溶液不仅有利于将磷酰胆碱聚合物应用于油基、油包水、水包油配方化妆品,通过磷酰胆碱聚合物在皮肤上的成膜性,降低刺激和提升保湿修复效果,解决现有技术中磷酰胆碱聚合物不溶于油、稳定性差、生物利用率低等问题。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.
此外,本发明还开发了以磷酰胆碱聚合物油性原液为基础原液的化妆品原料原液。In addition, the present invention also develops a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
具体地,本发明开发了一种高稳定、高相容性和透明的甘草黄酮油性原液(aqueous stock solution)、神经酰胺油溶液(也称为“油性原液”oliy stock solution)、甘草酸二钾油性原液。Specifically, 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 .
术语the term
如本文所用,对于本发明的油性原液而言,“活性成分”“本发明的油性原液”“本发明的磷酰胆碱聚合物”可互换使用,均指的是活性成分磷酰胆碱聚合物,其含有上述的(a)亲水性基团和(b)疏水性基团。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.
如本文所用,术语“本发明的油性原液”、“本发明的透明油溶液”、“本发明的磷酰胆碱聚合物透明油溶液”等可互换使用,指将油不溶性磷酰胆碱聚合物与乳化剂和油脂等特定成分混合,从而形成的具有高透明度、高稳定性、高生物相容性的油性原液。As used herein, the terms "oily stock solution of the present invention", "clear oil solution of the present invention", "phosphorylcholine polymer clear oil solution of the present invention" and the like are used interchangeably to refer to the combination of 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.
磷酰胆碱聚合物Phosphorylcholine polymer
在本发明的油性原液中,一种核心成分为磷酰胆碱聚合物(也称为脂质体类似结构物)。In the oily stock solution of the present invention, a core component is phosphorylcholine polymer (also called liposome-like structure).
如本文所用,术语“本发明的磷酰胆碱聚合物”和“本发明脂质体类似结构物”可互换使用。As used herein, the terms "phosphorylcholine polymer of the present invention" and "liposome analog structure of the present invention" are used interchangeably.
在本发明中,磷酰胆碱聚合物指含有磷酰胆碱基团的聚合物,尤其是侧链含有磷酰胆碱基团的聚合物。本发明的磷酰胆碱聚合物可以是均聚物,也可以是共聚物,包括无规共聚物、嵌段共聚物或其组合。本发明的共聚物可以是二元、三元 或多元共聚物。In the present invention, 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.
在本发明中,所述的磷酰胆碱基团可以直接与聚合物主链(backbone)连接(如端接于聚合物),也可以通过连接基团(例如,二价连接基团,或二价连接基团)与主链间接连接。In the present invention, 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.
此外,在本发明中,优选的磷酰胆碱聚合物还含有疏水基团,例如位于侧链的疏水基团、或位于末端的疏水基团。In addition, in the present invention, the preferred phosphorylcholine polymers also contain hydrophobic groups, such as hydrophobic groups located on side chains, or hydrophobic groups located at the terminals.
优选地,本发明的磷酰胆碱聚合物是用例如含磷酰胆碱基团的单体与不含磷酰胆碱基团的单体共聚形成的共聚物。Preferably, 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.
在另一优选例中,本发明的磷酰胆碱聚合物是用疏水单体(不含磷酰胆碱基团的单体)和亲水性单体(含磷酰胆碱基团)通过聚合反应形成的聚合物。In another preferred embodiment, 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.
本发明的磷酰胆碱聚合物可通过已知的方法制备,或通过市售购得。此外,本发明的磷酰胆碱聚合物还包括对聚合物进行改性所制备的磷酰胆碱聚合物。The phosphorylcholine polymers of the present invention can be prepared by known methods, or are commercially available. In addition, the phosphorylcholine polymer of the present invention also includes the phosphorylcholine polymer prepared by modifying the polymer.
优选地,本发明的磷酰胆碱聚合物(或脂质体类似结构物)含有式I所示的磷酰胆碱基团(优选作为支链上的基团):Preferably, 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):
Figure PCTCN2022075196-appb-000013
Figure PCTCN2022075196-appb-000013
式中,R 1、R 2和R 3各自独立地选自:H、C 1-C 4的烷烃基、C 3-C 4的环烷基; In the formula, R 1 , R 2 and R 3 are each independently selected from: H, C 1 -C 4 alkane, C 3 -C 4 cycloalkyl;
n为1、2、3、或4。n is 1, 2, 3, or 4.
优选地,R 1、R 2和R 3各自独立地选自:H、甲基或乙基。 Preferably, R 1 , R 2 and R 3 are each independently selected from: H, methyl or ethyl.
优选地,n为2或3。Preferably, n is 2 or 3.
在另一优选例中,所述磷酰胆碱聚合物的分子量没有特别限制,优选的重均分子量或数均分子量为1万~300万,更佳地5万-200万。In another preferred example, 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.
在另一优选例中,所述磷酰胆碱聚合物的例子包括(但不限于):2-甲基丙烯酰氧乙基磷酰胆碱均聚物、2-甲基丙烯酰氧乙基磷酰胆碱和其他亲水性和/或疏水性单体的共聚物或其组合,聚磷酸胆碱乙二醇丙烯酸酯、聚磷酸胆碱甲基丙烯酸正丁酯。In another preferred embodiment, 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.
本发明人意外地发现,当采用特定乳化剂时,可以显著改善油不溶性的磷酰胆碱聚合物的溶解性,很好地溶解分散在油或油性溶剂中,从而使得本发明的磷酰 胆碱聚合物油溶液(含高浓度的磷酰胆碱聚合物化合物的油性原液)获得高透明度,并具有更高的稳定性和更高的生物相容性等优异特性,从而显著提高由本发明的磷酰胆碱聚合物油溶液制作的化妆品中的磷酰胆碱聚合物含量,并提高磷酰胆碱聚合物的渗透性,增强其保湿修复等效果或功效。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.
其他成分other ingredients
在本发明的油性原液中,还可添加一种或多种额外成分,只要该额外成分不对本发明的油性原液造成实质性的影响(如导致磷酰胆碱聚合物的溶解度显著下降,导致不透明等)。In the oily stock solution of the present invention, 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).
这些额外成分是可有可无的,代表性的额外成分包括(但并不限于):防腐剂、香料、抗氧化剂、色素(如天然色素)、芳香剂、或其他化妆品上允许的活性组分(如神经酰胺)或辅料。These 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.
例如,可在本发明的油性原液中添加芳香剂以获得预定的芳香。For example, a fragrance can be added to the oily stock solution of the present invention to obtain a predetermined fragrance.
可以在本发明的油性原液添加防腐剂,以进一步获得长期放置的性能。代表性的防腐剂选自:苯氧乙醇、苯甲酸甲酯、山梨酸类、1,3-丁二醇、1,2-戊二醇、1,2-己二醇或其组合。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.
所述抗氧化剂选自:生育酚、生育酚醋酸酯、生育酚琥珀酸酯、生育酚混合物、或其混合物。The antioxidant is selected from: tocopherol, tocopherol acetate, tocopherol succinate, tocopherol mixture, or mixtures thereof.
制备方法Preparation
本发明还提供了制备本发明的透明的磷酰胆碱聚合物油性原液的方法。The present invention also provides a method for preparing the transparent phosphorylcholine polymer oily stock solution of the present invention.
在一个优选例中,所述方法包括步骤:In a preferred embodiment, the method includes the steps:
(1)提供磷酰胆碱聚合物、乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide phosphorylcholine polymer and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃,较佳地60-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
(3)将其他油脂加入至步骤(2)所述混合料中,随后降温至10-60℃而获得所述磷酰胆碱聚合物油性原液。(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.
化妆品原料原液Cosmetic raw material solution
本发明还提供了以磷酰胆碱聚合物油性原液为基础原液的化妆品原料原液。The present invention also provides a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
以甘草黄酮为例,甘草黄酮是从特定甘草中提取的天然化合物,在美容化妆品中有多种功效。甘草黄酮类化合物包含甘草甙、甘草甙元、天冬酞胺、甘露醇、 光甘草定等。Take licorice flavonoids as an example. 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.
甘草黄酮具有清除氧自由基的功效,其抗氧化能力与维生素E及过氧化物歧化酶(SOD)比较接近。甘草黄酮在医药上还具有抗菌抗炎、抗肿瘤、抗HIV、抗溃疡、抗心律失常、调整能量消耗和代谢等广泛的生物活性。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.
如本文所用,“甘草黄酮”、“甘草黄酮类化合物”可互换使用,指从甘草提取的黄酮类化合物。应理解,所述术语还包括人工合成或半合成的黄酮类化合物。此外,所述术语可以包括单一的甘草黄酮化合物,也可包括多种甘草黄酮构成的混合物,还可包括主要成分为甘草黄酮的提取物。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.
代表性的甘草黄酮包括(但并不限于):甘草黄酮类化合物包括黄酮类、二氢黄酮类、黄酮醇类、异黄酮类、查尔酮类和双黄酮类等化合物。其中,二氢黄酮类包括甘草苷、甘草苷元、新甘草苷、甘草素、光甘草定等;查尔酮类包括异甘草苷、异甘草素、异甘草苷元、新异甘草苷等。Representative licorice flavonoids include (but are not limited to): licorice flavonoids include compounds such as flavonoids, dihydroflavonoids, flavonols, isoflavones, chalcones, and diflavonoids. Among them, dihydroflavonoids include liquiritigenin, liquiritigenin, new liquiritigenin, liquiritigenin, glabridin, etc.; chalcones include isoliquiritigenin, isoliquiritigenin, isoliquiritigenin, new isoliquiritigenin, and the like.
甘草黄酮是从特定品种甘草中提取的天然美白剂,它能抑制酪氨酸酶的活性,又能抑制多巴色素互变和DHICA氧化酶的活性,是一种快速、高效、绿色的美白祛斑化妆品添加剂。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.
从甘草中提取的化合物-甘草黄酮在美容化妆品中有多种功效,同时,甘草黄酮还有抑制酪氨酸酶活性、清除氧自由基,具有抗炎、抗变态反应的作用。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.
在本发明中,优选的甘草黄酮为光甘草定,或光甘草定与其他甘草黄酮类化合物形成的混合物。In the present invention, the preferred licorice flavonoid is glabridin, or a mixture of glabridin and other licorice flavonoids.
本发明提供了一种甘草黄酮油性原液,以油性原液总重计,包含:0.1-10%甘草黄酮、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。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 .
一个实施方式中,所述甘草黄酮含有式Y1所示的美白活性成分光甘草定:In one embodiment, the licorice flavonoids contain the whitening active ingredient glabridin shown in formula Y1:
Figure PCTCN2022075196-appb-000014
Figure PCTCN2022075196-appb-000014
另一个实施方式中,所述甘草黄酮被脂质体结构类似物包裹,形成第一包覆物。In another embodiment, the licorice flavonoids are encapsulated by liposome structural analogs to form a first encapsulation.
本发明的方法提高了油性原液中甘草黄酮的溶解度,使得用本发明的油性原液制作的油基、油包水、水包油配方的化妆品中甘草黄酮含量升高,从而增强化妆品的美白效果。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.
本发明的方法提高了油性原液中甘草黄酮的稳定性,从而可以使得甘草黄酮作为活性成分更广泛,持续地应用在油基、油包水、水包油配方的化妆品。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.
本发明的甘草黄酮油性原液中,甘草黄酮充分分散,不会因不溶而导致混浊,从而增强了用本发明油性原液制作的油基、油包水、水包油配方的化妆品的生物相容性。In the licorice flavonoid oily stock solution of the present invention, 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 .
本发明的甘草黄酮油性原液,透光度好。The licorice flavonoid oily stock solution of the present invention has good light transmittance.
本发明的甘草黄酮油性原液中,脂质体结构类似物与甘草黄酮形成的包覆物粒径为分子级,从而使得用本发明油性原液制作的油基、油包水、水包油配方的化妆品中,甘草黄酮活性成分的渗透性强。In the licorice flavonoid oily stock solution of the present invention, 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.
本发明的甘草黄酮油溶液应用程度广泛,可以直接用于制备油基、油包水、水包油配方的的化妆品。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.
以神经酰胺为例,神经酰胺(Ceramide)是以神经酰胺为骨架的一类磷脂,主要有神经酰胺磷酸胆碱和神经酰胺磷酸乙醇胺,磷脂是细胞膜的主要成分,角质层中40%~50%的皮脂由神经酰胺构成,神经酰胺是细胞间基质的主要部分,在保持角质层水分的平衡中起着重要作用。神经酰胺具有很强缔合水分子能力,它通过在角质层中形成网状结构维持皮肤水分。因此,神经酰胺具有保持皮肤水分作用。Taking ceramide as an example, 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.
神经酰胺与细胞表面蛋白质通过酯键连接起到粘合细胞作用,这种相互之间联系被称为“脂质-细胞-蛋白质”包裹物。Smith等曾报道可通过测定表皮角质层中神经酰胺含量判断角化细胞之间粘着力大小,表皮角质层中神经酰胺含量减少可使角化细胞间粘着力下降,导致皮肤干燥、脱屑、呈鳞片状。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等对干性皮肤脱屑机理进行研究,结果发现,导致皮肤干燥主要原因是表皮角质层中神经酰胺含量减少,神经酰胺含量高低与皮肤干燥程度直接相关。使用神经酰胺可明显增强角化细胞之间粘着力,改善皮肤干燥程度,减少皮肤脱屑现象。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.
皮肤含水量约占体重18%~20%,皮肤润泽和弹性与表皮所含水分有密切关系,皮肤水分过量丢失会导致皮肤干燥,甚至皲裂。Imokawa等采用有机溶剂处理去除角质层脂质,发现皮肤持续(>4天)皲裂,出现鳞片状,皮肤电导率明显下降。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.
将提取到表皮角质层脂质组分分别在相同条件下进行局部皮肤试验,探讨哪一种脂质组分能对皮肤水分恢复有何作用。结果发现,神经酰胺局部使用可导致皮肤电导率非常明显增高,胆固醇其次,游离脂肪酸和胆固醇酯作用则不明显。The 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.
皮肤在衰老过程中,脂质合成下降,角质层中神经酰胺含量减少。皮肤衰老特征表现为:(1)皮肤干燥、脱屑,粗糙,失去光泽:(2)皮肤角质层变薄,皱纹增多,弹性下降。During skin aging, 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.
使用神经酰胺能使表皮角质层中神经酰胺含量增高,可改善皮肤干燥、脱屑、粗糙等状况;同时神经酰胺能增加表皮角质层厚度,提高皮肤持水能力,减少皱纹,增强皮肤弹性,延缓皮肤衰老。The use of 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.
神经酰胺存在于动、植物组织细胞膜,其分子将单糖或寡聚糖残基暴露于细胞外空间,参与同其它细胞、抗体、细菌毒素、病毒信封式蛋白的糖脂头部基团反应,因此神经酰胺在细胞粘合、调节细胞免疫、决定血型及作为瘤抗原方面起着非常重要作用。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.
虽然神经酰胺已被证明具有优异的皮肤角质层屏障修复功能,但其在水和油性成分中溶解度均较低,且分子量大,难以直接渗透进角质层发挥修复皮肤屏障的作用,影响其在护肤品中的添加及功效的体现。Although 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.
本发明提供了一种神经酰胺油性原液,以油性原液总重计,包含:0.1~10%神经酰胺、0.05~10%脂质体类似结构物、0.1~50%油脂、1~45%乳化剂。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 .
另一个实施方式中,所述神经酰胺为式Y2所示的化合物:In another embodiment, the ceramide is a compound represented by formula Y2:
Figure PCTCN2022075196-appb-000015
Figure PCTCN2022075196-appb-000015
式中,In the formula,
R 1选自:C 40-50烷基、C 40-50烯基、C 40-50炔基; R 1 is selected from: C 40-50 alkyl, C 40-50 alkenyl, C 40-50 alkynyl;
其中所述C 40-50烷基、C 40-50烯基、C 40-50炔基均包含:酯基、杂芳基、芳基及其组合; Wherein the 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选自:C 11-21烷基、C 11-21烯基、含有羟基的C 11-21烷基、含有羟基的C 11-21烯基、或其组合。 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.
另一个实施方式中,所述神经酰胺选自:经酰胺1[EOS]、神经酰胺2[NS]、神经酰胺3[NP]、神经酰胺4[EOS]、神经酰胺5[AS]、神经酰胺6[NH]、神经酰胺6II、神经酰胺7[AP]、神经酰胺8[AH]、神经酰胺9[EOP]、神经酰胺E或其组合;In another embodiment, 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;
其中,不同神经酰胺结构如下:Among them, different ceramide structures are as follows:
Figure PCTCN2022075196-appb-000016
Figure PCTCN2022075196-appb-000016
Figure PCTCN2022075196-appb-000017
Figure PCTCN2022075196-appb-000017
另一个实施方式中,所述神经酰胺被脂质体结构类似物包裹,形成第一包覆物。In another embodiment, the ceramide is encapsulated by a liposome structural analog to form a first encapsulation.
本发明的方法提高了油性原液中神经酰胺的溶解度,使得用本发明的油性原液制作的油基、油包水、水包油配方的化妆品中神经酰胺含量升高,从而增强化妆品的美白效果。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.
本发明的神经酰胺油溶液稳定度好,本发明方法制作的水油不溶性神经酰胺油性原液体系均匀稳定,利于终端产品的配伍稳定性。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.
按照本发明的制备方法制得的神经酰胺油性原液,其经皮渗透性提高了,功效更加显著。The ceramide oily stock solution prepared according to the preparation method of the present invention has improved transdermal permeability and more remarkable efficacy.
本发明的神经酰胺油溶液应用程度广泛,本发明的水油不溶性神经酰胺油溶液即可以用于制备油基配方的膏霜状化妆品,又可以直接制备油基、油包水、水包油配方的化妆品。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.
以甘草酸二钾为例,甘草酸以钾盐或钙盐的形式存在于甘草中,甘草酸二钾属于天然制品,是以甘草为原料进行提取分离而得甘草酸的衍生物。目前比较常用的甘草酸二钾的生产工艺是以甘草为原料提取甘草酸,通氨生成甘草酸单铵,再经过离子交换生成甘草酸二钾,使用较广泛的是单钾盐和二钾盐,二钾盐由于有药品标准,纯化程度高,市场可获得产品的质量稳定性好,多用于医药和化妆品。在化妆品领域,甘草酸二钾能深入皮肤内部并保持高活性,美白并高效抗氧化,有效抑制黑色素生成过程中多种酶的活性,特别是抑制酪胺酸酵素活性同时还具有防止皮肤粗糙和抗炎、抗菌的功效。根据甘草酸苷注射液皮肤修复的特性,甘 草酸二钾在皮肤修复方面也具有较大的潜在应用价值。Taking dipotassium glycyrrhizate as an example, 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. At present, the commonly used production process of 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. The most widely used are monopotassium salt and dipotassium salt. , Dipotassium salts 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. In the field of cosmetics, 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. According to the skin repair properties of glycyrrhizin injection, dipotassium glycyrrhizate also has great potential application value in skin repair.
本发明提供了一种甘草酸二钾油性原液,以油性原液总重计,包含:0.1-10%甘草酸二钾、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。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.
另一个实施方式中,所述甘草酸二钾含有式Y3所示的美白活性成分:In another embodiment, the dipotassium glycyrrhizinate contains the whitening active ingredient shown in formula Y3:
Figure PCTCN2022075196-appb-000018
Figure PCTCN2022075196-appb-000018
另一个实施方式中,所述甘草酸二钾被脂质体结构类似物包裹,形成第一包覆物。In another embodiment, the dipotassium glycyrrhizinate is encapsulated by a liposome structural analog to form a first encapsulation.
在另一优选例中,所述脂质体结构类似物含有(a)亲水性基团;(b)疏水性基团。In another preferred example, the liposome structural analog contains (a) a hydrophilic group; (b) a hydrophobic group.
在另一优选例中,所述亲水性基团含有式I所示支链结构:In another preferred example, the hydrophilic group contains a branched chain structure shown in formula I:
Figure PCTCN2022075196-appb-000019
Figure PCTCN2022075196-appb-000019
式中,R1,R2和R3各自独立地选自:H、C1-C4烷烃基、C3-C4的环烷基;In the formula, R1, R2 and R3 are each independently selected from: H, C1-C4 alkane, C3-C4 cycloalkyl;
其中所述疏水性基团包含:C5-30脂肪链结构。Wherein the hydrophobic group comprises: C5-30 aliphatic chain structure.
本发明的方法提高了油性原液中甘草酸二钾的溶解度,使得用本发明的油性原液制作的油基、油包水、水包油配方的化妆品中甘草酸二钾含量升高,从而增强化妆品的美白效果。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.
本发明的方法提高了油性原液中甘草酸二钾的稳定性,从而可以使得甘草酸二钾作为活性成分更广泛,持续地应用在油基、油包水、水包油配方的化妆品。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.
本发明的甘草酸二钾油性原液中,甘草酸二钾充分分散,不会因不溶而导致混浊,从而增强了用本发明油性原液制作的油基、油包水、水包油配方的化妆品的生物相容性。In the oily stock solution of dipotassium glycyrrhizate of the present invention, the dipotassium glycyrrhizate 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.
本发明的甘草酸二钾油性原液,透光度好。The dipotassium glycyrrhizate oily stock solution of the present invention has good light transmittance.
本发明的油性原液中,脂质体结构类似物与甘草酸二钾形成的包覆物粒径为分子级,从而使得用本发明油性原液制作的油基、油包水、水包油配方的化妆品中,甘草酸二钾活性成分的渗透性强。In the oily stock solution of the present invention, 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.
本发明的甘草酸二钾油性原液应用程度广泛,可以直接用于制备油基、油包水、水包油配方的的化妆品。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.
化妆品原料原液的制备Preparation of cosmetic raw material stock solution
本发明还提供了以磷酰胆碱聚合物油性原液为基础原液的化妆品原料原液的制备方法。The present invention also provides a preparation method of a cosmetic raw material stock solution based on the phosphorylcholine polymer oily stock solution.
具体地,本发明提供了磷酰胆碱聚合物油性原液的制备方法,所述方法包括步骤:Specifically, the present invention provides a method for preparing a phosphorylcholine polymer oily stock solution, the method comprising the steps of:
(1)提供磷酰胆碱聚合物、乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide phosphorylcholine polymer and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃,较佳地60-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
(3)将其他油脂加入至步骤(2)所述混合料中,随后降温至10-60℃而获得所述磷酰胆碱聚合物油性原液。(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.
以甘草黄酮为例,本发明提供了一种甘草黄酮原液的方法,所述方法包括步骤:Taking licorice flavonoids as an example, the present invention provides a method for licorice flavonoids stock solution, the method comprises the steps:
(a1)提供甘草黄酮、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(a1) provide licorice flavonoids, liposome structural analogs and emulsifiers, and mix them into an oil phase mixture according to a certain proportion;
(a2)将步骤(a1)中的油相混合料加热(如45-120℃),从而形成加热的混合料;(a2) heating the oil phase mixture in step (a1) (eg, 45-120° C.) to form a heated mixture;
(a3)将油脂加入至步骤(a2)所述混合料中,随后降温(如降温至20-80℃,优选地20-45℃)而获得降温的得到所述甘草黄酮油性原液;(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;
以神经酰胺为例,本发明提供了一种神经酰胺原液的方法,所述方法包括步骤:Taking ceramide as an example, the present invention provides a method for a ceramide stock solution, the method comprising the steps:
(b1)提供神经酰胺、脂质体类似结构物和油脂,并将它们按照一定比例混合成油相混合料;(b1) provide ceramide, liposome-like structure and oil, and mix them into oil phase mixture according to a certain proportion;
(b2)将步骤(b1)中的油相混合料加热至45-120℃;(b2) heating the oil phase mixture in step (b1) to 45-120°C;
(b3)将乳化剂加入至步骤(b2)所述混合料中,随后降温至20-80℃,优选地20-45℃而获油相混合料,得到所述的神经酰胺油性原液;(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;
以甘草酸二钾为例,本发明提供了一种甘草酸二钾原液的方法,所述方法包括步骤:Taking dipotassium glycyrrhizinate as an example, the invention provides a method for a stock solution of dipotassium glycyrrhizinate, the method comprising the steps:
(c1)提供甘草酸二钾、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(c1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(c2)将步骤(c1)中的油相混合料加热,从而形成加热的混合料;(c2) heating the oil phase mixture in step (c1), thereby forming a heated mixture;
(c3)将油脂加入至步骤(c2)所述混合料中,随后降温而获得降温的得到所述甘草酸二钾油性原液即为所述甘草酸二钾油性原液。(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.
本发明的主要优点包括:The main advantages of the present invention include:
(a)本发明的方法提高了油性原液中磷酰胆碱聚合物的溶解度,使得用本发明的油性原液制作的油基、油包水、水包油化妆品中磷酰胆碱聚合物含量升高,从而增强化妆品的保湿修复效果。(a) 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.
(b)本发明的方法提高了油性原液中磷酰胆碱聚合物的稳定性,从而可以使得磷酰胆碱聚合物作为活性成分更广泛,持续地应用在油基、油包水、水包油化妆品中。(b) 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.
(c)本发明的油性原液中,磷酰胆碱聚合物充分分散,不会因不溶而导致混浊,从而增强了用本发明油性原液制作的油基、油包水、水包油配方化妆品的生物相容性。(c) In the oily stock solution of the present invention, 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.
(d)本发明的磷酰胆碱聚合物油性原液,透光度好。(d) The phosphorylcholine polymer oily stock solution of the present invention has good light transmittance.
(e)本发明的油性原液中,磷酰胆脂聚合物与乳化剂充分混合,形成复合物,从而使得用本发明油性原液制作的油基、油包水、水包油配方化妆品,磷酰胆碱聚合物成膜性较好,保湿和降刺激性能良好。(e) In the oily stock solution of the present invention, 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.
(f)应用程度广泛,本发明的油溶液即可以直接用于制备油基、油包水、水包油配方的化妆品。(f) The degree of application is extensive, and the oil solution of the present invention can be directly used to prepare cosmetics with oil-based, water-in-oil and oil-in-water formulations.
下面结合具体实施例,进一步阐述本发明。应理解,这些实施例仅用于说明本发明而不用于限制本发明的范围。下列实施例中未注明具体条件的实验方法,通常按照常规条件,或按照制造厂商所建议的条件。除非另外说明,否则百分比和份数是重量百分比和重量份数。The present invention will be further described below in conjunction with specific embodiments. It should be understood that these examples are only used to illustrate the present invention and not to limit the scope of the present invention. In the following examples, the experimental methods without specific conditions are usually in accordance with conventional conditions, or in accordance with the conditions suggested by the manufacturer. Percentages and parts are weight percentages and parts unless otherwise specified.
实施例1.制备透明的磷酰胆碱聚合物油性原液No.1Example 1. Preparation of transparent phosphorylcholine polymer oily stock solution No.1
按照表1所示的原料比例称取各组分,然后按照以下步骤操作:Weigh each component according to the raw material ratio shown in Table 1, and then operate according to the following steps:
(1)提供磷酰胆碱聚合物、乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide phosphorylcholine polymer and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃,较佳地60-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
(3)将其他油脂加入至步骤(2)所述混合料中,随后降温至10-60℃而获得所述磷酰胆碱聚合物油性原液No.1(共100g)。(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).
表1原料配方(重量百分比)Table 1 raw material formula (weight percent)
原料raw material 实施例1Example 1 实施例2Example 2 对比例1Comparative Example 1
磷酰胆碱聚合物Phosphorylcholine polymer 22 44 22
油脂grease 5050 4646 9898
乳化剂Emulsifier 4848 5050 00
实施例2.制备透明的磷酰胆碱油性原液No.2Example 2. Preparation of transparent phosphorylcholine oily stock solution No.2
重复实施例1,不同点在于按照表1所示的实施例2的原料比例称取组分,从而制得磷酰胆碱油性原液No.2。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.
对比例1.制备透明的磷酰胆碱油性原液No.C1Comparative Example 1. Preparation of transparent phosphorylcholine oily stock solution No.C1
重复实施例1,不同点在于按照表1所示的对比例1的原料比例称取组分,从而制得磷酰胆碱油性原液No.C1。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.
实施例3.性能测试Example 3. Performance testing
在本实施例中,对实施例1-2制备的磷酰胆碱油性原液No.1~2以及对比例1制备的磷酰胆碱混合液No.C1进行性能测定。In this example, performance measurement was performed on the phosphorylcholine oily stock solutions No. 1 to 2 prepared in Examples 1-2 and the phosphoryl choline mixed solution No. C1 prepared in Comparative Example 1.
1.外观:1. Appearance:
测试方法:室温,拍照片,肉眼对比透明度。Test method: room temperature, take photos, and compare the transparency with the naked eye.
结果:result:
实施例1:外观透明(图1);Embodiment 1: the appearance is transparent (Fig. 1);
实施例2:外观透明;Embodiment 2: the appearance is transparent;
对比例1:外观浑浊(图2)Comparative example 1: cloudy appearance (Fig. 2)
2.稳定性:2. Stability:
测试方法:样品放在室温1个月;45℃循环(45℃放24h,恢复到室温24h,循环1个月);5℃观察1个月,-10℃观察1个月,肉眼对比透明度。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.
结果:如表2所示。Results: as shown in Table 2.
表2稳定性测试结果Table 2 Stability test results
   实施例1Example 1 实施例2Example 2 对比例1Comparative Example 1
室温(25℃)1个月Room temperature (25℃) 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
45℃,1个月45℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
5℃,1个月5℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
-10℃,1个月-10℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
实施例4.制备透明的甘草黄酮油性原液No.1Example 4. Preparation of transparent licorice flavonoid oily stock solution No.1
按照表3所示的原料比例称取各组分,然后按照以下步骤操作:Weigh each component according to the raw material ratio shown in Table 3, and then operate according to the following steps:
(1)提供甘草黄酮、脂质体结构类似物和乳化剂,并将它们按照一定比例混合 成油相混合料;(1) provide Glycyrrhiza flavonoids, liposome structural analog and emulsifier, and they are mixed into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C;
(3)将油脂加入至步骤(2)所述混合料中,随后降温至20-80℃,优选地20-45℃而获油相混合料;No.1(共100g)。(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).
表3原料配方(重量百分比)Table 3 raw material formula (weight percent)
原料raw material 实施例4Example 4 实施例5Example 5 比较例2Comparative Example 2
甘草黄酮 Licorice Flavonoids 11 11 11
脂质体结构类似物 Liposome Structural Analogs 11 99 00
油脂grease 4848 5050 9999
乳化剂Emulsifier 5050 4040 00
实施例5.制备甘草黄酮油溶液No.2Example 5. Preparation of licorice flavonoid oil solution No.2
重复实施例4,不同点在于按照表3所示的实施例5的原料比例称取组分,从而制得甘草黄酮油性原液No.2。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.
对比例2.制备甘草黄酮混合液Comparative example 2. Preparation of licorice flavonoid mixture
重复实施例4,不同点在于按照表3所示的对比例2的原料比例称取组分,从而制得甘草黄酮混合液No.C1。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.
实施例6.性能测试:Example 6. Performance test:
在本实施例中,对实施例4-6制备的甘草黄酮油性原液No.1-2以及对比例2制备的甘草黄酮混合液No.C1进行性能测定。In this example, performance measurement was performed on the licorice flavonoid oily stock solution No. 1-2 prepared in Example 4-6 and the licorice flavonoid mixed solution No. C1 prepared in Comparative Example 2.
1.外观:1. Appearance:
测试方法:室温,拍照片,肉眼对比透明度。Test method: room temperature, take photos, and compare the transparency with the naked eye.
结果:result:
实施例4:外观透明(图3);Embodiment 4: the appearance is transparent (Fig. 3);
实施例5:外观透明;Embodiment 5: the appearance is transparent;
比较例:外观浑浊(图4)。Comparative Example: The appearance was cloudy (FIG. 4).
2.稳定性:2. Stability:
测试方法:样品放在室温1个月;45℃循环(45℃放24h,恢复到室温24h,循环1个月);5℃观察1个月,-10℃观察1个月,肉眼对比透明度。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.
结果:如表4所示:Results: As shown in Table 4:
表4稳定性测试结果Table 4 Stability test results
   实施例4Example 4 实施例5Example 5 比较例2Comparative Example 2
室温(20℃)1个月Room temperature (20℃) 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
45℃,1个月45℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
5℃,1个月5℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
-10℃,1个月-10℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
实施例7.制备神经酰胺油溶液No.1Example 7. Preparation of Ceramide Oil Solution No. 1
按照表5所示的原料比例称取各组分,然后按照以下步骤操作:Weigh each component according to the raw material ratio shown in Table 5, and then operate according to the following steps:
(1)提供神经酰胺、脂质体类似结构物、油脂和乳化剂,并将它们按照一定比例混合成油相混合料;(1) Provide ceramide, liposome-like structure, oil and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C;
(3)将乳化剂加入至步骤(2)所述混合料中,随后降温至20-80℃,加入抗氧化剂,获得所述神经酰胺油溶液No.1,总重为100g。(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.
表5原料配方(重量百分比)Table 5 raw material formula (weight percent)
Figure PCTCN2022075196-appb-000020
Figure PCTCN2022075196-appb-000020
实施例8.制备神经酰胺油溶液No.2Example 8. Preparation of Ceramide Oil Solution No. 2
重复实施例7,不同点在于按照表5所示的实施例8的原料比例称取组分,从而制得神经酰胺油性原液No.2。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.
实施例9.制备神经酰胺油溶液No.3Example 9. Preparation of Ceramide Oil Solution No. 3
重复实施例7,不同点在于按照表5所示的实施例9的原料比例称取组分,从而制得神经酰胺油性原液No.3。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.
对比例3.制备神经酰胺混合液Comparative example 3. Preparation of ceramide mixture
重复实施例7,不同点在于按照表5所示的对比例3的原料比例称取组分,从而制得神经酰胺混合液No.C1。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.
实施例10性能测试:Example 10 Performance test:
在本实施例中,对实施例7-9制备的神经酰胺油性原液No.1-3以及对比例3制备的神经酰胺混合液No.C1进行性能测定。In this example, the performance measurement of the ceramide oily stock solutions No. 1-3 prepared in Examples 7-9 and the ceramide mixed solution No. C1 prepared in Comparative Example 3 was carried out.
1.外观:1. Appearance:
测试方法:室温,拍照片,肉眼对比透明度。Test method: room temperature, take photos, and compare the transparency with the naked eye.
结果:result:
实施例7:外观透明(图5);Embodiment 7: the appearance is transparent (Fig. 5);
实施例8:外观透明;Embodiment 8: the appearance is transparent;
实施例9:外观透明;Embodiment 9: the appearance is transparent;
对比例3:外观浑浊(图6)。Comparative Example 3: The appearance was cloudy (Fig. 6).
2.稳定性:2. Stability:
测试方法:样品放在室温1个月;45℃循环(45℃放24h,恢复到室温24h,循环1个月);5℃观察1个月,-10℃观察1个月,肉眼对比透明度。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.
结果:如表6所示:Results: As shown in Table 6:
表6稳定性测试结果Table 6 Stability test results
   实施例7Example 7 实施例8Example 8 实施例9Example 9 比较例3Comparative Example 3
室温(20℃)1个月Room temperature (20℃) 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
45℃,1个月45℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
5℃,1个月5℃, 1 month 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Appearance appears to be precipitated
-10℃-10℃ 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观仍保持透明The appearance remains transparent 外观出现沉淀Precipitation in appearance
实施例11.制备透明的甘草酸二钾油性原液No.1Example 11. Preparation of transparent dipotassium glycyrrhizinate oily stock solution No.1
按照表7所示的原料比例称取各组分,然后按照以下步骤操作:Weigh each component according to the raw material ratio shown in Table 7, and then operate according to the following steps:
(1)提供甘草酸二钾、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
(2)将步骤(1)中的油相混合料加热至45-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C;
(3)将油脂加入至步骤(2)所述混合料中,随后降温至20-80℃,优选地20-45℃而获油相混合料;No.1(共100g)。(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).
表7原料配方(重量百分比)Table 7 raw material formula (weight percent)
原料raw material 实施例11Example 11 实施例12Example 12 比较例4Comparative Example 4
甘草酸二钾 Dipotassium Glycyrrhizinate 11 11 11
脂质体结构类似物 Liposome Structural Analogs 11 99 00
油脂grease 4848 5050 9999
乳化剂Emulsifier 5050 4040 00
实施例12.制备甘草酸二钾油溶液No.2Example 12. Preparation of Dipotassium Glycyrrhizinate Oil Solution No.2
重复实施例11,不同点在于按照表7所示的实施例12的原料比例称取组分,从而制得甘草酸二钾油性原液No.2。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.
对比例4.制备甘草酸二钾混合液Comparative Example 4. Preparation of Dipotassium Glycyrrhizinate Mixture
重复实施例11,不同点在于按照表7所示的对比例4的原料比例称取组分,从而制得甘草酸二钾混合液No.C1。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.
实施例13.性能测试:Example 13. Performance test:
在本实施例中,对实施例11-13制备的甘草酸二钾油性原液No.1-2以及对比例4制备的甘草酸二钾混合液No.C1进行性能测定。In this example, the performance measurement of the dipotassium glycyrrhizinate oily stock solution No. 1-2 prepared in Example 11-13 and the dipotassium glycyrrhizate mixed solution No. C1 prepared in Comparative Example 4 was carried out.
1.外观:1. Appearance:
测试方法:室温,拍照片,肉眼对比透明度。Test method: room temperature, take photos, and compare the transparency with the naked eye.
结果:result:
实施例11:外观透明(图7);Embodiment 11: the appearance is transparent (Fig. 7);
实施例12:外观透明;Embodiment 12: the appearance is transparent;
比较例:外观浑浊(图8)。Comparative Example: The appearance was cloudy (FIG. 8).
2.稳定性:2. Stability:
测试方法:样品放在室温1个月;45℃循环(45℃放24h,恢复到室温24h,循环1个月);5℃观察1个月,-10℃观察1个月,肉眼对比透明度。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.
结果:如表8所示:Results: As shown in Table 8:
表8稳定性测试结果Table 8 Stability test results
Figure PCTCN2022075196-appb-000021
Figure PCTCN2022075196-appb-000021
在本发明提及的所有文献都在本申请中引用作为参考,就如同每一篇文献被单独引用作为参考那样。此外应理解,在阅读了本发明的上述讲授内容之后,本领域技术人员可以对本发明作各种改动或修改,这些等价形式同样落于本申请所附权利要求书所限定的范围。All documents mentioned herein are incorporated by reference in this application as if each document were individually incorporated by reference. In addition, it should be understood that after reading the above-mentioned teaching content of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the appended claims of the present application.

Claims (27)

  1. 一种磷酰胆碱聚合物油性原液,其特征在于,以油性原液总重计,包含:0.1-10%磷酰胆碱聚合物、5-50%乳化剂、和5-50%油脂。An oily stock solution of phosphorylcholine polymer is characterized in that, based on the total weight of the oily stock solution, it comprises: 0.1-10% phosphorylcholine polymer, 5-50% emulsifier, and 5-50% grease.
  2. 如权利要求1所述的磷酰胆碱聚合物油性原液,其特征在于,所述磷酰胆碱聚合物含有(a)亲水性基团;(b)疏水性基团。The oily stock solution of phosphorylcholine polymer according to claim 1, wherein the phosphorylcholine polymer contains (a) a hydrophilic group; (b) a hydrophobic group.
  3. 如权利要求2所述的磷酰胆碱聚合物油性原液,其特征在于,所述亲水性基团含有式I所示支链结构:The oily stock solution of phosphorylcholine polymer as claimed in claim 2, wherein the hydrophilic group contains a branched structure shown in formula I:
    Figure PCTCN2022075196-appb-100001
    Figure PCTCN2022075196-appb-100001
    式中,R 1,R 2和R 3各自独立地选自:H、C 1-C 4烷烃基、C 3-C 4的环烷基。 In the formula, R 1 , R 2 and R 3 are each independently selected from: H, C 1 -C 4 alkane, and C 3 -C 4 cycloalkyl.
  4. 如权利要求1所述的磷酰胆碱聚合物油性原液,其特征在于,所述油脂选自:棕榈酸异丙酯、棕榈酸异辛酯、异壬酸异壬酯、白油、甘油辛酸酯/癸酸三酯、辛基十二烷醇、椰油酸、月桂醇、肉豆蔻酸异丙酯、乳木果油、12-羟基硬脂酸异辛酯、苹果酸二异硬脂醇酯、角鲨烷、霍霍巴油、大豆油、橄榄油、甜杏仁油、鳄梨油、小麦胚芽油或其组合。The oily stock solution of phosphorylcholine polymer according to claim 1, wherein the oil is selected from the group consisting of: isopropyl palmitate, isooctyl palmitate, isononyl isononanoate, white oil, caprylyl glycerol Esters/Capric Triesters, Octyldodecanol, Coco Acid, Lauryl Alcohol, Isopropyl Myristate, Shea Butter, Isooctyl 12-Hydroxystearate, Diisostearyl Malate Alcohol ester, squalane, jojoba oil, soybean oil, olive oil, sweet almond oil, avocado oil, wheat germ oil, or combinations thereof.
  5. 如权利要求1所述的磷酰胆碱聚合物油性原液,其特征在于,所述乳化剂选自:聚甘油酯类、失水山梨醇脂肪酸酯系列、山梨醇椰油酸酯、蔗糖脂肪酸酯、烷基糖苷类、氢化卵磷脂、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚醚类、甘油辛酸/癸酸酯或其组合。The phosphorylcholine polymer oily stock solution according to claim 1, wherein the emulsifier is selected from the group consisting of: polyglycerol esters, sorbitan fatty acid ester series, sorbitan cocoate, sucrose fat acid esters, alkyl glycosides, hydrogenated lecithin, fatty alcohol polyoxyethylene ethers, alkylphenol polyoxyethylene ethers, fatty acid polyoxyethylene esters, polyethers, glycerol caprylic/capric acid esters, or combinations thereof.
  6. 一种制备权利要求1所述磷酰胆碱聚合物油性原液的方法,其特征在于,包括步骤:A method for preparing the described phosphorylcholine polymer oily stock solution of claim 1, characterized in that, comprising the steps:
    (1)提供磷酰胆碱聚合物、乳化剂,并将它们按照一定比例混合成油相混合料;(1) provide phosphorylcholine polymer and emulsifier, and mix them into oil phase mixture according to a certain proportion;
    (2)将步骤(1)中的油相混合料加热至45-120℃,较佳地60-120℃;(2) heating the oil phase mixture in step (1) to 45-120°C, preferably 60-120°C;
    (3)将其他油脂加入至步骤(2)所述混合料中,随后降温至10-60℃而获得所述磷酰胆碱聚合物油性原液。(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.
  7. 一种权利要求1所述的磷酰胆碱聚合物油性原液的用途,其特征在于,用于制造油基、油包水、水包油配方化妆品。A use of the phosphorylcholine polymer oily stock solution according to claim 1, characterized in that it is used in the manufacture of oil-based, water-in-oil, and oil-in-water formula cosmetics.
  8. 一种化妆品,其特征在于,含有权利要求1所述的磷酰胆碱聚合物油性原液。A cosmetic, characterized in that it contains the phosphorylcholine polymer oily stock solution according to claim 1.
  9. 如权利要求8所述的化妆品,其特征在于,所述的化妆品为油基配方的化妆品或含有油性辅料。The cosmetic according to claim 8, wherein the cosmetic is an oil-based formula cosmetic or contains oily auxiliary materials.
  10. 一种化妆品原料原液,其特征在于,所述的化妆品原料原液选自下组:A cosmetic raw material stock solution, characterized in that the cosmetic raw material stock solution is selected from the following group:
    (Y1)甘草黄酮油性原液,以油性原液总重计,包含:0.1-10%甘草黄酮、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂;(Y1) Glycyrrhiza flavonoids oily 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% oils and fats and 5-50% emulsifiers;
    (Y2)神经酰胺油性原液,以油性原液总重计,包含:0.1~10%神经酰胺、0.05~10%脂质体类似结构物、0.1~50%油脂、1~45%乳化剂;和(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)甘草酸二钾油性原液,以油性原液总重计,包含:0.1-10%甘草酸二钾、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。(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.
  11. 如权利要求10所述的原料原液,其特征在于,所述原液为甘草黄酮油性原液,以油性原液总重计,包含:0.1-10%甘草黄酮、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。The raw material stock solution according to claim 10, wherein the stock solution is an oily stock solution of licorice flavonoids, 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.
  12. 如权利要求11所述的原料原液,其特征在于,所述甘草黄酮含有式Y1所示的美白活性成分光甘草定:The raw material stock solution as claimed in claim 11, wherein the licorice flavonoids contain the whitening active ingredient glabridin shown in formula Y1:
    Figure PCTCN2022075196-appb-100002
    Figure PCTCN2022075196-appb-100002
  13. 如权利要求11所述的原料原液,其特征在于,所述甘草黄酮被脂质体结构类似物包裹,形成第一包覆物。The raw material solution according to claim 11, wherein the licorice flavonoids are encapsulated by liposome structural analogs to form a first encapsulation.
  14. 如权利要求10所述的原料原液,其特征在于,所述原液为神经酰胺油性原液,以油性原液总重计,包含:0.1~10%神经酰胺、0.05~10%脂质体类似结构物、0.1~50%油脂、1~45%乳化剂。The raw material stock solution according to claim 10, wherein the stock solution is an oily stock solution of ceramide, and based on the total weight of the oily stock solution, it comprises: 0.1-10% ceramide, 0.05-10% liposome-like structure, 0.1~50% oil, 1~45% emulsifier.
  15. 如权利要求14所述的原料原液,其特征在于,所述神经酰胺为式Y2所示的化合物:The raw material stock solution according to claim 14, wherein the ceramide is a compound represented by formula Y2:
    Figure PCTCN2022075196-appb-100003
    Figure PCTCN2022075196-appb-100003
    式中,In the formula,
    R 1选自:C 40-50烷基、C 40-50烯基、C 40-50炔基; R 1 is selected from: C 40-50 alkyl, C 40-50 alkenyl, C 40-50 alkynyl;
    其中所述C 40-50烷基、C 40-50烯基、C 40-50炔基均包含:酯基、杂芳基、芳基及其组合; Wherein the 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选自:C 11-21烷基、C 11-21烯基、含有羟基的C 11-21烷基、含有羟基的C 11-21烯基、或其组合。 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.
  16. 如权利要求14所述的原料原液,其特征在于,所述神经酰胺选自:经酰胺1[EOS]、神经酰胺2[NS]、神经酰胺3[NP]、神经酰胺4[EOS]、神经酰胺5[AS]、神经酰胺6[NH]、神经酰胺6II、神经酰胺7[AP]、神经酰胺8[AH]、神经酰胺9[EOP]、神经酰胺E或其组合;The raw material solution according to claim 14, wherein the ceramide is selected from the group consisting of: ceramide 1 [EOS], ceramide 2 [NS], ceramide 3 [NP], ceramide 4 [EOS], ceramide Ceramide 5 [AS], Ceramide 6 [NH], Ceramide 6II, Ceramide 7 [AP], Ceramide 8 [AH], Ceramide 9 [EOP], Ceramide E, or a combination thereof;
    其中,不同神经酰胺结构如下:Among them, different ceramide structures are as follows:
    Figure PCTCN2022075196-appb-100004
    Figure PCTCN2022075196-appb-100004
  17. 如权利要求10所述的原料原液,其特征在于,所述神经酰胺被脂质体结构类似物包裹,形成第一包覆物。The raw material solution according to claim 10, wherein the ceramide is encapsulated by a liposome structural analog to form a first encapsulation.
  18. 如权利要求10所述的原料原液,其特征在于,所述原液为甘草酸二钾油性原液,以油性原液总重计,包含:0.1-10%甘草酸二钾、0.05-10%脂质体结构类似物、10~50%油脂和5~50%乳化剂。The raw material stock solution according to claim 10, wherein the stock solution is an oily stock solution of dipotassium glycyrrhizinate, 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.
  19. 如权利要求18所述的原料原液,其特征在于,所述甘草酸二钾含有式Y3 所示的美白活性成分:The raw material stock solution according to claim 18, wherein the dipotassium glycyrrhizate contains the whitening active ingredient shown in formula Y3:
    Figure PCTCN2022075196-appb-100005
    Figure PCTCN2022075196-appb-100005
  20. 如权利要求18所述的原料原液,其特征在于,所述甘草酸二钾被脂质体结构类似物包裹,形成第一包覆物。The raw material solution according to claim 18, wherein the dipotassium glycyrrhizinate is encapsulated by the liposome structural analog to form a first encapsulation.
  21. 如权利要求11、14或18所述的原料原液,其特征在于,所述脂质体结构类似物含有(a)亲水性基团;(b)疏水性基团。The raw material solution according to claim 11, 14 or 18, wherein the liposome structural analog contains (a) a hydrophilic group; (b) a hydrophobic group.
  22. 如权利要求21所述的原料原液,其特征在于,所述亲水性基团含有式I所示支链结构:The raw material stock solution according to claim 21, wherein the hydrophilic group contains a branched structure shown in formula I:
    Figure PCTCN2022075196-appb-100006
    Figure PCTCN2022075196-appb-100006
    式中,R1,R2和R3各自独立地选自:H、C1-C4烷烃基、C3-C4的环烷基;In the formula, R1, R2 and R3 are each independently selected from: H, C1-C4 alkane, C3-C4 cycloalkyl;
    其中所述疏水性基团包含:C5-30脂肪链结构。Wherein the hydrophobic group comprises: C5-30 aliphatic chain structure.
  23. 如权利要求11、14或18所述的原料原液,其特征在于,所述油脂选自:棕榈酸异丙酯、棕榈酸异辛酯、异壬酸异壬酯、白油、甘油辛酸酯/癸酸三酯、辛基十二烷醇、椰油酸、月桂醇、肉豆蔻酸异丙酯、乳木果油、12-羟基硬脂酸异辛酯、苹果酸二异硬脂醇酯、角鲨烷、霍霍巴油、大豆油、橄榄油、甜杏仁油、鳄梨油、小麦胚芽油或其组合。The raw material stock solution according to claim 11, 14 or 18, wherein the oil is selected from the group consisting of: isopropyl palmitate, isooctyl palmitate, isononyl isononanoate, white oil, glycerol caprylate / Capric Triester, Octyldodecanol, 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.
  24. 如权利要求11、14或18所述的原料原液,其特征在于,所述乳化剂选自:聚甘油酯类、失水山梨醇脂肪酸酯系列、山梨醇椰油酸酯、蔗糖脂肪酸酯、烷基糖苷类、氢化卵磷脂、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪酸聚氧乙烯酯、聚醚类、甘油辛酸/癸酸酯或其组合。The raw material stock solution according to claim 11, 14 or 18, wherein the emulsifier is selected from the group consisting of: polyglycerol esters, sorbitan fatty acid ester series, sorbitan cocoate, sucrose fatty acid ester , alkyl glycosides, hydrogenated lecithin, fatty alcohol polyoxyethylene ethers, alkylphenol polyoxyethylene ethers, fatty acid polyoxyethylene esters, polyethers, glycerol caprylic/capric acid esters, or combinations thereof.
  25. 一种制备权利要求10所述的化妆品原料原液的方法,其特征在于,所述方法包括步骤:A method for preparing the cosmetic raw material stock solution of claim 10, wherein the method comprises the steps:
    (a1)提供甘草黄酮、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(a1) provide licorice flavonoids, liposome structural analogs and emulsifiers, and mix them into an oil phase mixture according to a certain proportion;
    (a2)将步骤(a1)中的油相混合料加热(如45-120℃),从而形成加热的混合料;(a2) heating the oil phase mixture in step (a1) (eg, 45-120° C.) to form a heated mixture;
    (a3)将油脂加入至步骤(a2)所述混合料中,随后降温(如降温至20-80℃,优选地20-45℃)而获得降温的得到所述甘草黄酮油性原液;(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;
    或所述方法包括步骤:or the method comprises the steps:
    (b1)提供神经酰胺、脂质体类似结构物和油脂,并将它们按照一定比例混合成油相混合料;(b1) provide ceramide, liposome-like structure and oil, and mix them into oil phase mixture according to a certain proportion;
    (b2)将步骤(b1)中的油相混合料加热至45-120℃;(b2) heating the oil phase mixture in step (b1) to 45-120°C;
    (b3)将乳化剂加入至步骤(b2)所述混合料中,随后降温至20-80℃,优选地20-45℃而获油相混合料,得到所述的神经酰胺油性原液;(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;
    或所述方法包括步骤:or the method comprises the steps:
    (c1)提供甘草酸二钾、脂质体结构类似物和乳化剂,并将它们按照一定比例混合成油相混合料;(c1) provide dipotassium glycyrrhizinate, liposome structural analog and emulsifier, and mix them into oil phase mixture according to a certain proportion;
    (c2)将步骤(c1)中的油相混合料加热,从而形成加热的混合料;(c2) heating the oil phase mixture in step (c1), thereby forming a heated mixture;
    (c3)将油脂加入至步骤(c2)所述混合料中,随后降温而获得降温的得到所述甘草酸二钾油性原液即为所述甘草酸二钾油性原液。(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.
  26. 如权利要求10所述的原料原液的用途,其特征在于,用于制备油基、油包水、水包油配方的化妆品。The use of the raw material stock solution according to claim 10, characterized in that, it is used to prepare cosmetics with oil-based, water-in-oil, and oil-in-water formulations.
  27. 一种化妆品,其特征在于,含有权利要求11、14或18所述的原料原液。A cosmetic comprising the raw material solution according to claim 11 , 14 or 18 .
PCT/CN2022/075196 2021-02-02 2022-01-30 Clear oily solution of phosphorylcholine polymer, cosmetic raw material stock solution, and preparation method therefor and application thereof WO2022166926A1 (en)

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CN202110179830.5A CN113181080A (en) 2021-02-07 2021-02-07 Transparent oil solution of phosphorylcholine polymer and its preparation method and use
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JP2002356519A (en) * 2001-05-30 2002-12-13 Nof Corp Phosphorylcholine analog containing polymer and application
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