Ceramide liposome for skin care products and preparation method of ceramide liposome

Ceramide liposomes prepared by using hydrogenated lecithin, modified cholesterol and other raw materials, the problem of limited application of natural ceramide in skin care products is solved, and efficient skin delivery and good stability and moisturizing effects are achieved.

CN119656047AActive Publication Date: 2025-03-21GUANGZHOU HUALIANG BIOTECHNOLOGY CO LTD

Patent Information

Application Number
CN202411894521.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-12-20
Publication Date
2025-03-21
Estimated Expiration
2044-12-20

AI Technical Summary

Technical Problem

Natural ceramides are limited in skin care products. Due to their high melting point and low solubility, they lead to crystallization, poor transdermal performance and instability, which affects the stability and utilization of the formula.

Method used

The raw materials such as hydrogenated lecithin, modified cholesterol, ceramide, sucrose stearate and polyglycerol-10 stearate were prepared through ultrasonic dissolution and rotary evaporation.

Benefits of technology

It achieves efficient percutaneous delivery of ceramide and high concentration enrichment in the skin, with good stability, skin barrier repair and moisturizing and water-locking effects, delaying the aging process.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

The invention relates to the field of skin care products, and discloses a ceramide liposome for skin care products and a preparation method thereof, the ceramide liposome comprises the following components by weight: 5-10 parts of hydrogenated lecithin, 0.5-2 parts of modified cholesterol, 0.5-2 parts of ceramide, 0.1-2.5 parts of sucrose stearate, 0.1-1 part of polyglycerol-10 stearate, and 15-30 parts of an organic solvent; the modified cholesterol is prepared by grafting glycine cholesteryl ester and carboxymethyl chitosan through a chemical reaction, the glycine cholesteryl ester is prepared from cholesterol, N-t-butyloxycarboryl glycine and trifluoroacetic acid as raw materials, and the carboxymethyl chitosan is prepared by grafting chloroacetic acid and chitosan. According to the invention, hydrogenated lecithin, modified cholesterol, ceramide, sucrose stearate and polyglycerol-10 stearate are used as raw materials to prepare the ceramide liposome with good stability, good skin barrier repairing property and good moisturizing and water locking effects.
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Description

Technical Field

[0001] The invention belongs to the technical field of skin care products, and particularly relates to a ceramide liposome used in skin care products and a preparation method thereof. Background Art

[0002] Ceramide, also known as brain amide and N-acylsphingosine, is a common structural unit of (neuro)sphingolipids. Ceramide is an important lipid naturally present in the stratum corneum of the skin, with physiological functions such as moisturizing, maintaining skin barrier, anti-aging, anti-allergy, and inducing cell apoptosis. Studies have shown that ceramide can induce apoptosis of skin diseased cells, cancer cells, etc., and has potential medical application value. With the development of nanotechnology, liposome-based nanocarrier delivery technology has become an important means to promote transdermal drug absorption and a hot spot in cosmetic technology. Conventional liposomes are composed of soy lecithin and cholesterol, which can effectively encapsulate water-soluble and fat-soluble active ingredients. They have the advantages of targeting, sustained release, promoting penetration and good cell affinity, and have been widely used in daily chemicals, agriculture, biomedicine and other fields.

[0003] In recent years, with the in-depth study of ceramides, more and more scientific research institutions and brand companies have launched a large number of cosmetics containing ceramides, which have attracted widespread attention and become hot-selling products. However, the important prerequisite for the realization of skin care effects is that the active ingredients can effectively penetrate the surface of the skin and be highly concentrated and retained in the skin tissue for a long time, that is, to achieve skin-targeted delivery of skin care active ingredients. However, natural ceramides have a high melting point and low solubility. Direct addition of ceramides will cause crystallization, poor transdermal performance, and instability due to susceptibility to the surrounding environment, which not only affects the stability of the formula, but also reduces the utilization rate of ceramides, limiting the application of ceramides in skin care products and other fields. Summary of the invention

[0004] In order to solve the deficiencies mentioned in the above background technology, the purpose of the present invention is to provide a ceramide liposome for skin care products and a preparation method thereof, using hydrogenated lecithin, modified cholesterol, ceramide, sucrose stearate and polyglycerol-10 stearate as raw materials to prepare ceramide liposomes with good stability and good skin barrier repair and moisturizing effects.

[0005] The purpose of the present invention can be achieved by the following technical solutions:

[0006] A ceramide liposome for skin care products, comprising the following components in parts by weight: 5-10 parts of hydrogenated lecithin, 0.5-2 parts of modified cholesterol, 0.5-2 parts of ceramide, 0.1-2.5 parts of sucrose stearate, 0.1-1 part of polyglycerol-10 stearate, and 15-30 parts of an organic solvent;

[0007] The modified cholesterol is prepared by grafting glycine cholesterol ester and carboxymethyl chitosan by chemical reaction, wherein glycine cholesterol ester is prepared by using cholesterol, N-tert-butyloxycarbonylglycine and trifluoroacetic acid as raw materials, and carboxymethyl chitosan is prepared by grafting chloroacetic acid and chitosan.

[0008] Preferably, the ceramide is one or more combinations of ceramide NP, ceramide NH, ceramide AH, ceramide NDS, ceramide AS, ceramide AP, ceramide NS, ceramide EOS, ceramide EOH, ceramide ADS, and ceramide EOP.

[0009] Preferably, the organic solvent is anhydrous ethanol.

[0010] Preferably, the method for preparing the modified cholesterol comprises the following steps:

[0011] A. Cholesterol and N-tert-butyloxycarbonylglycine were dissolved in anhydrous dichloromethane, 4-dimethylaminopyridine and N,N'-dicyclohexylcarbodiimide were added, and the reaction was carried out in an ice bath for 20 to 24 hours. After the reaction was completed, the reaction was filtered and the solvent was removed by vacuum distillation. The reaction product was dissolved in acetone and then reacted at 0 to 4°C for 8 to 12 hours. The precipitate was removed by filtration and the solvent was evaporated to dryness to prepare N-tert-butyloxycarbonylglycine-cholesterol ester;

[0012] B. Dissolve the obtained N-tert-butyloxycarbonylglycine-cholesterol ester in anhydrous dichloromethane, add trifluoroacetic acid with stirring in an ice bath, react at 0-4°C for 2-3h, and then remove the solvent by distillation under reduced pressure. Dissolve the reaction product in sodium chloride solution, adjust the pH value to 4-5, and then filter. Extract the filtrate with chloroform, dry the organic phase with anhydrous sodium sulfate for 8-12h, and finally evaporate to dryness to prepare glycine cholesterol ester.

[0013] C. Take chitosan powder in a reactor, add isopropanol to react for 3-4h, then add sodium hydroxide solution, heat to 55-70°C, take chloroacetic acid dissolved in isopropanol and add to the reactor to stir and react for 1-2h, cool to room temperature after the reaction is completed, remove the upper solution, add deionized water to the remaining product and stir and mix, adjust the pH value to neutral with hydrochloric acid solution, then centrifuge to remove insoluble matter, fully precipitate the supernatant with methanol and centrifuge, then add anhydrous ethanol to wash the precipitate, and finally centrifuge and dry to prepare carboxymethyl chitosan;

[0014] D. Dissolve carboxymethyl chitosan in dimethyl sulfoxide, add N-hydroxysuccinimide and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride to react for 20 to 30 minutes, then dissolve glycine cholesterol ester in N,N-dimethylformamide and add to the reaction system, react for 20 to 24 hours under nitrogen protection, after the reaction is completed, pour the reaction solution into acetone for precipitation, filter, and then wash the precipitate with tetrahydrofuran, dialyze the final product, and freeze-dry to prepare modified cholesterol.

[0015] Preferably, in step A, the mass ratio of cholesterol to N-tert-butyloxycarbonylglycine is 1:0.45-0.6.

[0016] Preferably, in step C, the mass ratio of chitosan to chloroacetic acid is 1:0.5-1.

[0017] Preferably, in step D, the mass ratio of carboxymethyl chitosan to glycine cholesterol ester is 0.17-0.35:1.

[0018] The method for preparing ceramide liposomes for skin care products as described above comprises the following steps: weighing raw materials in parts by weight, taking hydrogenated lecithin, modified cholesterol and ceramide in a reactor, adding an organic solvent and ultrasonically dissolving them, and after uniform dissolution, placing them at 40 to 50° C. and performing reduced pressure rotary evaporation to remove the organic solvent, adding sucrose stearate and polyglycerol-10 stearate, rotating and hydrating for 1 to 2 hours, and then placing them at a power of 60 to 100 W for ultrasonic treatment to prepare ceramide liposomes for skin care products.

[0019] Preferably, the hydration temperature is 40-50°C.

[0020] Beneficial effects of the present invention:

[0021] The invention utilizes cholesterol and N-tert-butyloxycarbonyl protected glycine to react to prepare N-tert-butyloxycarbonyl glycine-cholesterol ester, then adds trifluoroacetic acid for deprotection to prepare glycine-cholesterol ester, and utilizes chitosan to modify into carboxymethyl chitosan, and further utilizes carboxymethyl chitosan and glycine cholesterol ester to react to prepare modified cholesterol, thereby grafting carboxymethyl chitosan onto the cholesterol molecular chain through a strong chemical bond, so that the cholesterol grafted carboxymethyl chitosan has amphiphilicity, wherein chitosan is a natural amino alkaline polysaccharide widely existing in nature, which is renewable, has no toxic side effects, has good biocompatibility and degradability, and has antibacterial, moisturizing and other effects, and carboxymethyl chitosan has good solubility, thickening and dispersibility, and can increase the stability of liposomes. The present invention uses hydrogenated lecithin, modified cholesterol and ceramide as raw materials, adds sucrose stearate and polyglycerol-10 stearate as emulsifiers and surfactants to form ceramide liposomes, which can efficiently deliver active ingredients encapsulated therein through the skin, have excellent stability and skin tolerance, and can also renew the skin's natural protective layer and form an effective barrier to prevent water loss. The prepared ceramide liposomes are applied to skin care products, which can promote ceramide to penetrate the epidermis and produce sufficient accumulation in corresponding parts, thereby achieving the effects of efficient moisturizing and water locking, skin repair, anti-oxidation, and anti-aging. DETAILED DESCRIPTION

[0022] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0023] Example 1 A method for preparing modified cholesterol comprises the following steps:

[0024] A. Take 5.7g of cholesterol and 2.9g of N-tert-butyloxycarbonylglycine and dissolve them in 100mL of anhydrous dichloromethane, add 0.3g of 4-dimethylaminopyridine and 2.3g of N,N'-dicyclohexylcarbodiimide, react in an ice bath for 24h, filter after the reaction, remove the solvent by vacuum distillation, dissolve the reaction product in 20mL of acetone and react at 4°C for 10h, filter to remove the precipitate and evaporate the solvent to prepare N-tert-butyloxycarbonylglycine-cholesterol ester;

[0025] B. The obtained N-tert-butyloxycarbonylglycine-cholesterol ester was dissolved in 50 mL of anhydrous dichloromethane, and 50 mL of trifluoroacetic acid was added after stirring in an ice bath. The mixture was placed at 0°C for 2 h and then the solvent was removed by distillation under reduced pressure. The reaction product was dissolved in a 15% sodium chloride solution, and the pH value was adjusted to 5 and then filtered. The filtrate was extracted with chloroform, and the organic phase was dried with anhydrous sodium sulfate for 12 h, and finally evaporated to dryness to prepare glycine cholesteryl ester.

[0026] C. Take 5g of chitosan powder in a reactor, add 20mL of isopropanol to react for 4h, then add 30% sodium hydroxide solution, heat to 65°C, take 3g of chloroacetic acid, dissolve in 20mL of isopropanol and add to the reactor to stir and react for 2h, cool to room temperature after the reaction is completed, remove the upper solution, add 50mL of deionized water to the remaining product, stir and mix, adjust the pH value to neutral with 10% hydrochloric acid solution, then centrifuge to remove insoluble matter, fully precipitate the supernatant with methanol and centrifuge, then add anhydrous ethanol to wash the precipitate, and finally centrifuge and dry to prepare carboxymethyl chitosan;

[0027] D. Take 2.2g of carboxymethyl chitosan and dissolve it in 100mL of dimethyl sulfoxide, add 0.6g of N-hydroxysuccinimide and 2.1g of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride and react for 30min, then take 10g of glycine cholesterol ester and dissolve it in 100mL of N,N-dimethylformamide and add it to the reaction system, react for 24h under nitrogen protection, after the reaction is completed, pour the reaction solution into acetone for precipitation, filter, and then wash the precipitate with tetrahydrofuran, dialyze the final product and freeze-dry it to prepare modified cholesterol.

[0028] Example 2 A ceramide liposome for skin care products comprises the following components in parts by weight: 5 parts of hydrogenated lecithin, 0.7 parts of modified cholesterol prepared in Example 1, 0.8 parts of ceramide NP, 0.3 parts of sucrose stearate, 0.2 parts of polyglycerol-10 stearate, and 17 parts of anhydrous ethanol.

[0029] The preparation method of the ceramide liposome for skin care products comprises the following steps: weighing raw materials in parts by weight, taking hydrogenated lecithin, modified cholesterol and ceramide NP in a reactor, adding anhydrous ethanol for ultrasonic dissolution, and after uniform dissolution, placing it at 45°C for reduced pressure rotary evaporation to remove the organic solvent, adding sucrose stearate and polyglycerol-10 stearate, rotating and hydrating for 1 hour, the hydration temperature is 40°C, and then placing it at 80W power for ultrasonic treatment to prepare ceramide liposome for skin care products.

[0030] Example 3 A ceramide liposome for skin care products comprises the following components in parts by weight: 7 parts of hydrogenated lecithin, 1.2 parts of modified cholesterol prepared in Example 1, 1.4 parts of ceramide NP, 1.7 parts of sucrose stearate, 0.5 parts of polyglycerol-10 stearate, and 24 parts of anhydrous ethanol.

[0031] The preparation method of the ceramide liposome for skin care products is the same as that in Example 2.

[0032] Example 4 A ceramide liposome for skin care products comprises the following components in parts by weight: 10 parts of hydrogenated lecithin, 1.8 parts of modified cholesterol prepared in Example 1, 2 parts of ceramide NP, 2.2 parts of sucrose stearate, 1 part of polyglycerol-10 stearate, and 28 parts of anhydrous ethanol.

[0033] The preparation method of the ceramide liposome for skin care products is the same as that in Example 2.

[0034] Comparative Example 1 A ceramide liposome for skin care products comprises the following components in parts by weight: 10 parts of hydrogenated lecithin, 1.8 parts of modified cholesterol prepared in Example 1, 2 parts of ceramide NP, 3.2 parts of Tween 80, and 28 parts of anhydrous ethanol.

[0035] The preparation method of the ceramide liposome for skin care products comprises the following steps: weighing raw materials in parts by weight, taking hydrogenated lecithin, modified cholesterol and ceramide NP in a reactor, adding anhydrous ethanol for ultrasonic dissolution, and after uniform dissolution, placing it at 45°C for reduced pressure rotary evaporation to remove the organic solvent, adding Tween 80, rotating hydration for 1 hour, the hydration temperature is 40°C, and then placing it at 80W power for ultrasonic treatment to prepare ceramide liposome for skin care products.

[0036] Comparative Example 2 A ceramide liposome for skin care products comprises the following components in parts by weight: 10 parts of hydrogenated lecithin, 1.8 parts of cholesterol, 2 parts of ceramide NP, 2.2 parts of sucrose stearate, 1 part of polyglycerol-10 stearate, and 28 parts of anhydrous ethanol.

[0037] The preparation method of the ceramide liposome for skin care products comprises the following steps: weighing raw materials in parts by weight, taking hydrogenated lecithin, cholesterol and ceramide NP in a reactor, adding anhydrous ethanol and ultrasonically dissolving them, and after uniform dissolution, placing them at 45°C and performing reduced pressure rotary evaporation to remove the organic solvent, adding sucrose stearate and polyglycerol-10 stearate, rotating and hydrating for 1 hour, the hydration temperature is 40°C, and then placing them at 80W power for ultrasonic treatment to prepare ceramide liposome for skin care products.

[0038] Performance Testing

[0039] The ceramide liposomes prepared in Examples 2-4 and Comparative Examples 1-2 were used to prepare gel:

[0040] (1) heating deionized water, erythritol, butylene glycol, glyceryl polyether-26, ammonium acryloyldimethyltaurate / VP copolymer, xanthan gum, carbomer, p-hydroxyacetophenone, and 1,2-hexanediol to 78° C. and stirring to obtain a mixture A;

[0041] (2) adding polydimethylsiloxane, cyclopentasiloxane, cyclohexasiloxane, peony seed oil, and tangerine peel to the mixture A, and performing a homogenization treatment to obtain a homogenized mixture B. The homogenization conditions are as follows: a homogenization temperature of 82° C., a homogenization speed of 7500 rpm, and a homogenization time of about 3 min;

[0042] (3) Add arginine, ceramide liposomes, panthenol, and a compound sensitizer to the mixture B, and stir evenly to obtain a gel containing ceramide liposomes.

[0043] A. Stability test: The prepared gel containing ceramide liposomes was placed under high temperature (45°C), low temperature (-15°C), high temperature (45°C, 48h), normal temperature (25°C, 12h) and low temperature (-15°C, 48h) cyclic temperature conditions for 90 days to observe whether the samples have stratification, precipitation of particles, coarsening, transparency, and crystallization; the samples were placed under natural light conditions for 90 consecutive days to observe whether the samples have discoloration, taste change, etc. The data results are shown in Table 1.

[0044] B. Skin irritation test: The test was conducted with reference to the patch test method in the Technical Specification for Safety of Cosmetics (2015 edition). 32 test subjects who met the standards were selected, and about 0.020-0.025 mL of the sample was applied to the patch test chamber, and then applied to the back or curved forearm of the test subject with a special adhesive tape. The patch test chamber was removed after 24 hours. If there was any remaining product, it was gently wiped off with a moistened tissue. The skin reaction was observed after 0.5 hours, 24 hours and 48 hours, and the data results are shown in Table 1.

[0045] Table 1 Test results of sample stability and skin irritation

[0046]

[0047]

[0048] From the data in Table 1, it can be seen that the skin care products prepared in Examples 2-4 of the present invention have good stability. No delamination, particle precipitation, coarsening, transparency, or crystallization occurs when placed under high temperature, low temperature, and cross conditions for 90 days. The samples do not change color or taste when placed under natural light conditions for 90 consecutive days, and are non-irritating to the skin. In Comparative Example 1, sucrose stearate and polyglycerol-10 stearate are replaced with Tween 80 of equal mass, and cholesterol is not modified in Comparative Example 2. The samples are measured to be delaminated under high temperature and cyclic temperature conditions, indicating that the addition of sucrose stearate and polyglycerol-10 stearate and the grafting of carboxymethyl chitosan can improve the stability of the samples.

[0049] C. Moisturizing function and skin barrier function test: 40 subjects with an average age of 25 to 45 years old were selected, including 20 females and 20 males, and randomly divided into 5 groups, 8 in each group. The subjects had healthy skin and met the inclusion criteria. The test area was drawn on the inner side of the right forearm of the subject at room temperature of 20°C and relative humidity of 35%, and was stabilized for at least half an hour. The skin in the test area was torn with tape 10 times and then the experimental sample was applied. The sample usage was 1 mL, and the moisturizing function and skin barrier function test was performed:

[0050] C 1。 Moisturizing function test: Use the skin moisture tester Corneometer CM825 to test the moisture content of the skin before and after damage, and 4 hours after applying the sample. Repeat 3 times to get the average value and calculate the skin moisture content growth rate. The calculation formula is as follows: Skin moisture content growth rate = (M 1 -M 2 ) / M 2 ×100%, where M 2 M is the moisture content of the skin before use; 1 The moisture content of the skin after use is shown in Table 2.

[0051] C 2 .Skin barrier function test: TewameterTM300 was used to test the loss of skin moisture before and after the skin was damaged, as well as 6 hours after applying the sample. This was repeated 3 times to obtain the average value and calculate the rate of change of the TEWL value. The TEWL value is an important parameter for describing the skin barrier and is closely related to the water content of the stratum corneum. The higher the TEWL value, the more water is lost through the skin and the poorer the barrier function of the stratum corneum. The data results are shown in Table 2.

[0052] Table 2 Test results of sample moisturizing function and skin barrier function

[0053]

[0054] From the data in Table 2, it can be seen that the skin care products prepared in Examples 2-4 of the present invention have good skin barrier repair and moisturizing and water-locking effects. The moisture content growth rate measured in Comparative Example 1-2 is lower than that in Example 2-4, and the transepidermal water loss is more obvious than that in Example 2-4, indicating that the addition of sucrose stearate and polyglycerol-10 stearate and the grafting of carboxymethyl chitosan can prolong the moisturizing and water-locking effect of the sample and reduce transepidermal water loss.

[0055] In the description of this specification, the description with reference to the terms "one embodiment", "example", "specific example", etc. means that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present invention. In this specification, the schematic representation of the above terms does not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments or examples in a suitable manner.

[0056] The above shows and describes the basic principles, main features and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments, and the above embodiments and descriptions are only for explaining the principles of the present invention. Without departing from the spirit and scope of the present invention, the present invention may have various changes and improvements, and these changes and improvements all fall within the scope of the present invention to be protected.

Claims

1. A ceramide liposome for skin care products, characterized in that: The invention comprises the following components in parts by weight: 5 to 10 parts of hydrogenated lecithin, 0.5 to 2 parts of modified cholesterol, 0.5 to 2 parts of ceramide, 0.1 to 2.5 parts of sucrose stearate, 0.1 to 1 part of polyglycerol-10 stearate, and 15 to 30 parts of organic solvent; The modified cholesterol is prepared by grafting glycine cholesterol ester and carboxymethyl chitosan by chemical reaction, wherein glycine cholesterol ester is prepared by using cholesterol, N-tert-butyloxycarbonylglycine and trifluoroacetic acid as raw materials, and carboxymethyl chitosan is prepared by grafting chloroacetic acid and chitosan.

2. The ceramide liposome for skin care products according to claim 1, characterized in that: The ceramide is one or more combinations of ceramide NP, ceramide NH, ceramide AH, ceramide NDS, ceramide AS, ceramide AP, ceramide NS, ceramide EOS, ceramide EOH, ceramide ADS, and ceramide EOP.

3. The ceramide liposome for skin care products according to claim 1, characterized in that: The organic solvent is anhydrous ethanol.

4. The ceramide liposome for skin care products according to claim 1, characterized in that: The preparation method of the modified cholesterol comprises the following steps: A. Cholesterol and N-tert-butyloxycarbonylglycine were dissolved in anhydrous dichloromethane, 4-dimethylaminopyridine and N,N'-dicyclohexylcarbodiimide were added, and the reaction was carried out in an ice bath for 20 to 24 hours. After the reaction was completed, the reaction was filtered and the solvent was removed by vacuum distillation. The reaction product was dissolved in acetone and then reacted at 0 to 4°C for 8 to 12 hours. The precipitate was removed by filtration and the solvent was evaporated to dryness to prepare N-tert-butyloxycarbonylglycine-cholesterol ester; B. Dissolve the obtained N-tert-butyloxycarbonylglycine-cholesterol ester in anhydrous dichloromethane, add trifluoroacetic acid with stirring in an ice bath, react at 0-4°C for 2-3h, and then remove the solvent by distillation under reduced pressure. Dissolve the reaction product in sodium chloride solution, adjust the pH value to 4-5, and then filter. Extract the filtrate with chloroform, dry the organic phase with anhydrous sodium sulfate for 8-12h, and finally evaporate to dryness to prepare glycine cholesterol ester. C. Chitosan powder is placed in a reactor, isopropanol is added to react for 3-4 hours, and then sodium hydroxide solution is added, the temperature is raised to 55-70°C, chloroacetic acid is dissolved in isopropanol and added to the reactor, and the mixture is stirred and reacted for 1-2 hours. After the reaction is completed, the mixture is cooled to room temperature, the upper layer solution is removed, and the remaining product is added with deionized water and stirred and mixed. The pH value is adjusted to neutral with hydrochloric acid solution, and then the insoluble matter is removed by centrifugation. The supernatant is fully precipitated with methanol and then centrifuged, and then anhydrous ethanol is added to wash the precipitate, and finally centrifuged and dried to prepare carboxymethyl chitosan; D. Dissolve carboxymethyl chitosan in dimethyl sulfoxide, add N-hydroxysuccinimide and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride to react for 20 to 30 minutes, then dissolve glycine cholesterol ester in N,N-dimethylformamide and add to the reaction system, react for 20 to 24 hours under nitrogen protection, after the reaction is completed, pour the reaction solution into acetone for precipitation, filter, and then wash the precipitate with tetrahydrofuran, dialyze the final product, and freeze-dry to prepare modified cholesterol.

5. The ceramide liposome for skin care products according to claim 4, characterized in that: The mass ratio of cholesterol to N-tert-butyloxycarbonylglycine in step A is 1:0.45-0.

6.

6. The ceramide liposome for skin care products according to claim 4, characterized in that: In step C, the mass ratio of chitosan to chloroacetic acid is 1:0.5-1.

7. The ceramide liposome for skin care products according to claim 4, characterized in that: In the step D, the mass ratio of carboxymethyl chitosan to glycine cholesterol ester is 0.17-0.35:

1.

8. A method for preparing ceramide liposomes for skin care products according to any one of claims 1 to 7, characterized in that: The method comprises the following steps: weighing raw materials in parts by weight, putting hydrogenated lecithin, modified cholesterol and ceramide in a reactor, adding an organic solvent for ultrasonic dissolution, placing the mixture at 40-50°C for reduced pressure rotary evaporation to remove the organic solvent after uniform dissolution, adding sucrose stearate and polyglycerol-10 stearate, rotating and hydrating for 1-2 hours, and then placing the mixture at 60-100W for ultrasonic treatment to prepare ceramide liposomes for skin care products.

9. The method for preparing ceramide liposomes for skin care products according to claim 8, characterized in that: The hydration temperature is 40-50°C.

Citation Information

Patent Citations

  • Preparation method for amphiphilic konjac glucomannan cholesterol grafted polymer and application

    CN102399301A

  • Mask liquid with skin barrier repair function and preparation method of mask liquid

    CN110179692A

  • High-content ceramide, cholesterol and fatty acid composition and preparation method thereof

    CN118319785A

  • Liposome composition

    JP2014208626A

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