A compound with anti-aging activity, its preparation method and application in skin care products

Abstract

The present application relates to the field of cosmetic technology, in particular to a compound with anti-aging activity, a preparation method thereof and application in skin care products, in order to reduce the catalytic activity of cerium oxide powder and improve its dispersibility in cosmetics, the present application carries out coating treatment on nano cerium oxide, and mixes guanidine silane with coated cerium oxide powder, the methoxy in guanidine silane will be hydrolyzed to combine with the hydroxyl on the surface of coated cerium oxide powder, so as to endow the cerium oxide powder with antibacterial function, and then the present application further mixes it with isostearic acid, so as to introduce branched alkyl on the surface of cerium oxide powder, change the surface polarity of cerium oxide powder, so as to be beneficial to the dispersibility of cerium oxide in cosmetics and other products.

Description

Technical Field

[0001] This invention relates to the field of cosmetic technology, specifically to a compound with anti-aging activity, its preparation method, and its application in skincare products. Background Technology

[0002] The core cause of photoaging is the oxidative stress response triggered by ultraviolet radiation, which continuously generates a large number of reactive oxygen free radicals. These free radicals damage the skin's collagen and elastin fiber structure, leading to aging problems such as sagging, fine lines, dullness, and roughness. Cerium oxide, with its unique... Its reversible valence state conversion property gives it a long-lasting, bidirectional free radical scavenging ability. It can efficiently decompose various aging reactive oxygen species such as superoxide anions and hydroxyl radicals, block the oxidation chain reaction, inhibit skin oxidative damage caused by ultraviolet rays and external environmental stimuli from the root, reduce collagen degradation and pigment deposition, continuously repair the skin barrier, and achieve long-lasting anti-aging and delay skin aging effects. Compared with traditional single antioxidant raw materials, it has the unique advantages of strong stability, long-lasting effect and multi-target anti-aging. However, the application of existing cerium oxide powder has obvious limitations: On the one hand, the redox properties of cerium oxide may catalyze the oxidative degradation of certain unstable components in the formulation, accelerating product deterioration, rancidity, or color changes, affecting product safety, stability, and shelf life; at the same time, the redox activity of unmodified pure cerium oxide powder is non-selective. While exerting anti-aging and free radical scavenging effects, it is prone to react with functional anti-aging and skin care components such as active peptides, vitamins, and plant extracts in cosmetic formulations. This not only depletes the activity of effective anti-aging ingredients in the formulation and significantly reduces the overall anti-aging efficacy of the product, but also disrupts the balance of the formulation system and exacerbates product failure. On the other hand, in order to improve the whitening effect after application and enhance visual transparency, the industry often uses nano-sized cerium oxide. However, nanoparticles are prone to agglomeration and sedimentation in the system, resulting in uneven distribution of sun protection performance and decreased product storage stability. Furthermore, agglomerated nano-cerium oxide particles will significantly reduce the utilization rate of surface active sites, directly weakening its free radical scavenging efficiency, leading to a significant reduction in anti-aging activity. This prevents the full exertion of its antioxidant and anti-aging effects, severely restricting its practical application effect and market acceptance. Summary of the Invention

[0003] The purpose of this invention is to provide a compound with anti-aging activity, its preparation method, and its application in skin care products, in order to solve the problems of excessive catalytic activity and uneven dispersion of cerium oxide.

[0004] To solve the above-mentioned technical problems, the present invention provides the following technical solution:

[0005] In a first aspect, the present invention provides a method for preparing a compound with anti-aging activity, comprising the following steps:

[0006] Nano-cerium oxide was dispersed in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, ammonia was added dropwise to adjust the pH, and tetraethyl orthosilicate was added dropwise. After the addition was completed, the mixture was heated to react and then cooled to room temperature. The precipitate was separated by centrifugation, washed with anhydrous ethanol, and dried to obtain coated cerium oxide powder.

[0007] 1-(diaminomethylene)guanidine and triethylamine were added to anhydrous isopropanol and stirred until homogeneous. Under a nitrogen atmosphere, 3-chloropropyltrimethoxysilane was added, and the mixture was heated to react. After cooling to room temperature, the mixture was filtered, and the excess solvent was removed by rotary evaporation of the filtered solution to obtain guanidinosilane.

[0008] Cerium oxide powder was dispersed in anhydrous ethanol and ultrasonically dispersed until uniform. Guanidylsilane was added and mixed evenly. Deionized water was added and stirred to react. The precipitate was separated by centrifugation, washed with anhydrous ethanol, dried, ground and sieved to obtain antibacterial cerium oxide powder.

[0009] Antibacterial cerium oxide powder was mixed with isostearic acid and boric acid, reacted under vacuum, cooled to room temperature, and the resulting product was washed with n-hexane, dried under vacuum, and the powder was collected, ground and sieved to obtain a compound with anti-aging activity.

[0010] Furthermore, in the process of preparing coated cerium oxide powder, the mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate used is 5:(80~100):(20~25):(7~8.5); the pH is 9~9.5.

[0011] Furthermore, during the preparation of coated cerium oxide powder, the temperature is raised to 40-45℃ and the reaction is stirred for 4-6 hours.

[0012] Furthermore, in the preparation of guanidinosilane, the mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane used is (0.45~0.48):(0.3~0.38):1.

[0013] Furthermore, during the preparation of guanidinosilane, the temperature is raised to 65-68°C and the reaction is stirred for 5-8 hours.

[0014] Furthermore, in the process of preparing antibacterial cerium oxide powder, the mass ratio of coated cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water used is 5: (50~80): (0.3~1.5): (0.1~0.15).

[0015] During the stirring reaction, the reaction temperature is 15~25℃, and the stirring reaction time is 2.5~4h.

[0016] Furthermore, in the process of preparing compounds with anti-aging activity, the mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid used is 5:(0.5~1.5):(0.015~0.02).

[0017] Furthermore, during the vacuum reaction, the vacuum level is evacuated to -0.05 to -0.08 MPa, the temperature is raised to 110 to 115°C, and the reaction is stirred for 2 to 3 hours.

[0018] Secondly, the present invention also provides a compound with anti-aging activity prepared by the above preparation method.

[0019] Thirdly, the present invention also provides the application of a compound with anti-aging activity in skin care products. The present invention can be applied to skin care products with ultraviolet sun protection requirements, and its usage amount is 0.1~10wt% of the total mass of the skin care product lotion.

[0020] Compared with the prior art, the beneficial effects achieved by the present invention are:

[0021] To reduce the catalytic activity of cerium oxide powder and improve its dispersibility in cosmetics, this invention involves coating nano-cerium oxide. Firstly, tetraethyl orthosilicate is used as a modifier. Under alkaline conditions, tetraethyl orthosilicate hydrolyzes to generate silanol Si-OH. The silanol undergoes dehydration condensation with the hydroxyl groups on the cerium oxide surface, and simultaneously crosslinks and polymerizes to form a dense, amorphous silica isolation shell on the particle surface, thereby isolating the photocatalytic active sites of cerium oxide.

[0022] However, the silicon hydroxyl groups still present on the surface of the silicon oxide coating layer generated under this reaction will make the cerium oxide powder exhibit strong hydrophilicity, thereby affecting its dispersion in skin care products, sunscreens and other products. Therefore, based on this, the present invention further modifies it.

[0023] This invention uses 3-chloropropyltrimethoxysilane as a raw material, which is mixed with 1-(diaminomethylene)guanidine. The chlorine atom in 3-chloropropyltrimethoxysilane undergoes an affinity substitution reaction with the amino group in 1-(diaminomethylene)guanidine, removing HCl and generating a stable C–N covalent bond. This yields an antibacterial guanidine silane with terminal silanyl methoxy groups and guanidine groups in the middle / terminal segments of the molecular chain. The guanidine groups present have a strong antibacterial effect against Staphylococcus aureus and Propionibacterium acnes, common bacteria on the skin, thus preventing bacterial growth caused by oily facial skin and excessive sebum from skincare products. Excessive proliferation of harmful bacteria on the skin surface can induce skin inflammation and microbial imbalance, accelerating skin inflammation, aging, roughness, and dullness. This guanidine antibacterial structure can effectively inhibit the growth of harmful bacteria on the skin, maintain the stability of the skin's microecology, reduce inflammatory aging problems, and synergize with the antioxidant and anti-aging properties of cerium oxide. It delays skin aging from both anti-inflammatory and antioxidant dimensions, enriching the anti-aging mechanism of the material.

[0024] Building upon this foundation, this invention mixes guanidinosilane with cerium oxide-coated powder. With the participation of water molecules, the methoxy groups in the guanidinosilane hydrolyze and combine with the hydroxyl groups on the surface of the cerium oxide powder, endowing the cerium oxide powder with antibacterial properties. Furthermore, this invention further mixes it with isostearic acid. Under the catalysis of boric acid, the carboxyl groups in isostearic acid react with the amino groups in the guanidinosilane, thereby introducing branched alkyl groups onto the surface of the cerium oxide powder. This alters the surface polarity of the cerium oxide powder, improving its dispersibility in cosmetics and other products. The modified cerium oxide powder can be evenly distributed in skincare systems, ensuring uniform contact with antioxidant active sites on every part of the skin, maximizing the release of antioxidants. Its free radical scavenging ability avoids problems such as localized anti-aging failure and uneven sun protection caused by powder agglomeration; at the same time, the stable surface modified structure can lock in the anti-aging activity of cerium oxide for a long time, eliminate the interference of the formula system, and achieve long-lasting, stable and uniform anti-photoaging and antioxidant skin care effects. Moreover, the dual mechanism of antibacterial anti-aging and antioxidant anti-aging is superimposed, which significantly improves the overall skin anti-aging and repair ability of the material. Attached Figure Description

[0025] Figure 1 This is a TEM image of the nano-cerium oxide powder used in Example 1 of this invention;

[0026] Figure 2 This is a TEM image of the compound with anti-aging activity prepared in Example 1 of this invention. Detailed Implementation

[0027] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0028] In the embodiments and comparative examples of this invention, the nano-cerium oxide used is GM-108 high-precision rare earth polishing powder produced by Shanghai Huaming Gaona Rare Earth New Materials Co., Ltd., with a CeO2 content > 99% and D 50 μm is 0.6~1;

[0029] The 1-(diaminomethylene)guanidine and 3-chloropropyltrimethoxysilane used were purchased from Shanghai Aladdin Biochemical Technology Co., Ltd., with a purity of ≥98%.

[0030] The tetraethyl orthosilicate used was purchased from Shanghai Lingfeng Chemical Reagent Co., Ltd., and was of analytical grade; the boric acid used was purchased from Hangzhou Gaojing Fine Chemical Co., Ltd., and was of analytical grade.

[0031] Example 1

[0032] A method for preparing a compound with anti-aging activity includes the following steps:

[0033] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9. Add tetraethyl orthosilicate. After the addition is complete, heat to 40℃ and stir for 6 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain coated cerium oxide powder.

[0034] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:80:20:7.

[0035] S2. Add 1-(diaminomethylene)guanidine and triethylamine to anhydrous isopropanol, stir and mix evenly, then under a nitrogen atmosphere, add 3-chloropropyltrimethoxysilane, heat to 65°C, stir and react for 8 hours, cool to room temperature, filter, and remove excess solvent by rotary evaporation to obtain guanidinosilane.

[0036] The mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane is 0.45:0.3:1.

[0037] S3. Disperse the coated cerium oxide powder in anhydrous ethanol, ultrasonically disperse it evenly, add guanidinosilane, mix evenly, add deionized water, heat to 15°C, stir and react for 4 hours, centrifuge to separate the precipitate, wash the precipitate with anhydrous ethanol, dry it, grind and sieve it to obtain antibacterial cerium oxide powder.

[0038] The mass ratio of the cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water is 5:50:0.3:0.1.

[0039] S4. The antibacterial cerium oxide powder was mixed with isostearic acid and boric acid, and the mixture was evacuated to a vacuum degree of -0.05 MPa. The temperature was raised to 110°C, and the mixture was stirred for 3 hours. After cooling to room temperature, the product was washed with n-hexane, dried under vacuum, and the powder was collected, ground, and sieved to obtain a compound with anti-aging activity.

[0040] The mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid is 5:0.5:0.015.

[0041] Example 2

[0042] A method for preparing a compound with anti-aging activity includes the following steps:

[0043] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9.5. Add tetraethyl orthosilicate. After the addition is complete, heat to 40℃ and stir for 5 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain coated cerium oxide powder.

[0044] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:90:22:8.

[0045] S2. Add 1-(diaminomethylene)guanidine and triethylamine to anhydrous isopropanol, stir and mix evenly, then under a nitrogen atmosphere, add 3-chloropropyltrimethoxysilane, heat to 65°C, stir and react for 6 hours, cool to room temperature, filter, and remove excess solvent by rotary evaporation to obtain guanidinosilane.

[0046] The mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane is 0.45:0.35:1.

[0047] S3. Disperse the coated cerium oxide powder in anhydrous ethanol, ultrasonically disperse it evenly, add guanidinosilane, mix evenly, add deionized water, heat to 20°C, stir and react for 3 hours, centrifuge to separate the precipitate, wash the precipitate with anhydrous ethanol, dry it, grind and sieve it to obtain antibacterial cerium oxide powder.

[0048] The mass ratio of the cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water is 5:60:1:0.12.

[0049] S4. The antibacterial cerium oxide powder was mixed with isostearic acid and boric acid, and the mixture was evacuated to a vacuum degree of -0.06 MPa. The temperature was raised to 110℃, and the mixture was stirred for 2.5 h. After cooling to room temperature, the product was washed with n-hexane, dried under vacuum, and the powder was collected, ground and sieved to obtain a compound with anti-aging activity.

[0050] The mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid is 5:1:0.02.

[0051] Example 3

[0052] A method for preparing a compound with anti-aging activity includes the following steps:

[0053] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9.3. Add tetraethyl orthosilicate dropwise. After the addition is complete, heat to 45℃ and stir for 4 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain coated cerium oxide powder.

[0054] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:100:25:8.5.

[0055] S2. Add 1-(diaminomethylene)guanidine and triethylamine to anhydrous isopropanol, stir and mix evenly, then under a nitrogen atmosphere, add 3-chloropropyltrimethoxysilane, heat to 68°C, stir and react for 5 hours, cool to room temperature, filter, and remove excess solvent by rotary evaporation to obtain guanidinosilane.

[0056] The mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane is 0.48:0.38:1.

[0057] S3. Disperse the coated cerium oxide powder in anhydrous ethanol, ultrasonically disperse it evenly, add guanidinosilane, mix evenly, add deionized water, heat to 25°C, stir and react for 2.5 h, centrifuge to separate the precipitate, wash the precipitate with anhydrous ethanol, dry it, grind and sieve it to obtain antibacterial cerium oxide powder.

[0058] The mass ratio of the cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water is 5:80:1.5:0.15.

[0059] S4. The antibacterial cerium oxide powder was mixed with isostearic acid and boric acid, and the mixture was evacuated to a vacuum degree of 0.08 MPa. The temperature was raised to 115°C, and the mixture was stirred for 2 hours. After cooling to room temperature, the product was washed with n-hexane, dried under vacuum, and the powder was collected, ground, and sieved to obtain a compound with anti-aging activity.

[0060] The mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid is 5:1.5:0.02.

[0061] Comparative Example 1

[0062] Compared with Example 3, this comparative example did not perform step S4, but only used antibacterial cerium oxide powder as a compound product with anti-aging activity;

[0063] A method for preparing a compound with anti-aging activity includes the following steps:

[0064] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9. Add tetraethyl orthosilicate. After the addition is complete, heat to 45℃ and stir for 4 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain coated cerium oxide powder.

[0065] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:100:25:8.5.

[0066] S2. Add 1-(diaminomethylene)guanidine and triethylamine to anhydrous isopropanol, stir and mix evenly, then under a nitrogen atmosphere, add 3-chloropropyltrimethoxysilane, heat to 68°C, stir and react for 5 hours, cool to room temperature, filter, and remove excess solvent by rotary evaporation to obtain guanidinosilane.

[0067] The mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane is 0.48:0.38:1.

[0068] S3. Disperse the cerium oxide powder in anhydrous ethanol, ultrasonically disperse it evenly, add guanidinosilane, mix evenly, add deionized water, heat to 25°C, stir and react for 2.5 h, centrifuge to separate the precipitate, wash the precipitate with anhydrous ethanol, dry it, grind and sieve it to obtain a compound with anti-aging activity.

[0069] The mass ratio of the cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water is 5:80:1.5:0.15.

[0070] Comparative Example 2

[0071] Compared with Example 3, this comparative example did not perform steps S2 and S3, but directly used the cerium oxide powder coated in step S1 to participate in the reaction in step S4;

[0072] A method for preparing a compound with anti-aging activity includes the following steps:

[0073] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9. Add tetraethyl orthosilicate. After the addition is complete, heat to 45℃ and stir for 4 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain coated cerium oxide powder.

[0074] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:100:25:8.5.

[0075] S4. The cerium oxide powder coated with isostearic acid and boric acid were mixed, the vacuum was drawn to a vacuum degree of 0.08 MPa, the temperature was raised to 115℃, the reaction was stirred for 2 hours, and after cooling to room temperature, the product was washed with n-hexane, dried under vacuum, the powder was collected, ground and sieved to obtain a compound with anti-aging activity.

[0076] The mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid is 5:1.5:0.02.

[0077] Comparative Example 3

[0078] Compared with Example 3, this comparative example only underwent step S1 processing;

[0079] A method for preparing a compound with anti-aging activity includes the following steps:

[0080] S1. Disperse nano-cerium oxide in a mixture of anhydrous ethanol and deionized water. After ultrasonic dispersion, add 25wt% ammonia water to adjust the pH to 9. Add tetraethyl orthosilicate. After the addition is complete, heat to 45℃ and stir for 4 hours. Cool to room temperature, centrifuge to separate the precipitate, wash with anhydrous ethanol, and dry to obtain a compound with anti-aging activity.

[0081] The mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate is 5:100:25:8.5.

[0082] Comparative Example 4

[0083] Compared with Example 3, this comparative example did not perform any treatment on the nano-cerium oxide, but directly used nano-cerium oxide as the finished compound with anti-aging activity.

[0084] Testing: The following ingredients were mixed: 17wt% glycerin, 0.4wt% p-hydroxyacetophenone, 16wt% squalane, 0.1wt% aromatic essential oil, 5wt% Winsier Plus, 0.8wt% sodium chloride, 15wt% of the above-mentioned anti-aging active compounds, and the remainder distilled water. After stirring for 20 minutes, the skin care product sample was obtained.

[0085] Antibacterial activity test: Staphylococcus aureus and Propionibacterium acnes were cultured separately in LB medium to prepare a concentration of 10. 8 After preparing the bacterial suspension at CFU / mL, the bacterial suspension was inoculated into the skin care product samples prepared in Examples 1-3 and Comparative Examples 1-4 at a ratio of 10g skin care product sample to 1mL bacterial suspension. After stirring and mixing evenly, 1mL of test sample was transferred at 0h and 24h after inoculation, and the bacterial count was detected by the dilution plating method to calculate the antibacterial rate.

[0086] The formula for calculating the antibacterial rate is as follows:

[0087] ;

[0088] Photocatalytic performance testing:

[0089] Methylene blue was dispersed in deionized water to prepare a 2.5 mg / L methylene blue solution. Then, a compound with anti-aging activity was added to it at a ratio of 100 mg / L. The light was simulated by a 250 W metal halide lamp with a 400 nm filter. Samples of the filtrate were taken at the beginning of irradiation and 2 hours after irradiation. The absorbance at 664 nm was measured using a UV spectrophotometer to obtain the methylene blue degradation rate.

[0090] The formula for calculating the methylene blue degradation rate is as follows:

[0091]

[0092] The anti-aging compound prepared in Example 1 was subjected to SEM image analysis before and after preparation. The results are shown in the figure. Figure 1 , 2 ;

[0093] The test results are shown in the table below:

[0094]

[0095] As can be seen from the data in Examples 1-3, the compounds with anti-aging activity prepared in this application have excellent antibacterial properties against common pathogens and common skin pathogens, and their photodegradation efficiency is also effectively reduced after being coated.

[0096] The data from Comparative Example 1 show that, due to the absence of step S4, the cerium oxide powder surface did not introduce branched alkyl groups of isostearic acid, resulting in insufficient dispersibility of the cerium oxide powder in cosmetics and a decrease in antibacterial properties. In Comparative Example 2, both antibacterial properties and photocatalytic activity showed significant changes. This is because Comparative Example 2 only used the coated cerium oxide powder treated in step S1 for step S4 treatment, meaning that the silica-coated cerium oxide directly participated in step S4. Under this condition, no antibacterial groups were grafted onto the cerium oxide powder surface, and the coating condition affected the antibacterial properties of cerium oxide itself, leading to a decrease in antibacterial properties. However, due to the reduction in the coating layer, the photocatalytic activity of cerium oxide actually increased.

[0097] In Comparative Example 3, since only the coating in step S1 was performed, its photocatalytic activity increased compared to Example 3. As for Comparative Example 4, no treatment was performed on the nano-cerium oxide powder, so it had the strongest photocatalytic degradation activity.

[0098] Finally, it should be noted that the above descriptions are merely preferred embodiments of the present invention and are not intended to limit the present invention. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A method for preparing a compound with anti-aging activity, characterized in that, Includes the following steps: Nano-cerium oxide was added to a mixture of anhydrous ethanol and deionized water, ultrasonically dispersed, ammonia was added dropwise to adjust the pH, tetraethyl orthosilicate was added dropwise, the reaction was heated, cooled to room temperature, the precipitate was separated by centrifugation, washed with anhydrous ethanol and dried to obtain coated cerium oxide powder. 1-(diaminomethylene)guanidine and triethylamine were added to anhydrous isopropanol, stirred, and then 3-chloropropyltrimethoxysilane was added under a nitrogen atmosphere. After heating and reacting, the mixture was cooled to room temperature, filtered, and the filtrate was rotary evaporated to obtain guanidinylsilane. The coated cerium oxide powder was added to anhydrous ethanol, ultrasonically dispersed, then guanidinosilane was added, mixed evenly, and then deionized water was added. After stirring and reacting, the precipitate was separated by centrifugation, washed with anhydrous ethanol, dried, ground and sieved to obtain antibacterial cerium oxide powder. In the process of preparing antibacterial cerium oxide powder, the mass ratio of coated cerium oxide powder, anhydrous ethanol, guanidinosilane, and deionized water is 5: (50~80): (0.3~1.5): (0.1~0.15). During the stirring reaction, the reaction temperature is 15~25℃, and the stirring reaction time is 2.5~4h. Antibacterial cerium oxide powder was mixed with isostearic acid and boric acid, reacted under vacuum, cooled to room temperature, and the product was washed with n-hexane, dried under vacuum, ground and sieved to obtain a compound with anti-aging activity.

2. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: In the process of preparing coated cerium oxide powder, the mass ratio of nano-cerium oxide, anhydrous ethanol, deionized water, and tetraethyl orthosilicate used is 5:(80~100):(20~25):(7~8.5); the pH is 9~9.

5.

3. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: During the preparation of coated cerium oxide powder, the temperature is raised to 40-45℃ and the reaction is stirred for 4-6 hours.

4. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: In the preparation of guanidinosilane, the mass ratio of 1-(diaminomethylene)guanidine, triethylamine, and 3-chloropropyltrimethoxysilane used is (0.45~0.48):(0.3~0.38):

1.

5. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: In the preparation of guanidinosilane, the temperature is raised to 65-68℃ and the reaction is stirred for 5-8 hours.

6. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: In the process of preparing compounds with anti-aging activity, the mass ratio of antibacterial cerium oxide powder, isostearic acid, and boric acid used is 5:(0.5~1.5):(0.015~0.02).

7. The method for preparing a compound with anti-aging activity according to claim 1, characterized in that: During the vacuum reaction, the vacuum level is evacuated to -0.05 to -0.08 MPa, the temperature is raised to 110 to 115°C, and the reaction is stirred for 2 to 3 hours.

8. A compound with anti-aging activity prepared by the preparation method according to any one of claims 1 to 7.

9. The use of a compound with anti-aging activity as described in claim 8 in a skin care product.

Images