A method for preparing and applying a long-acting anthelmintic compound microcapsule

By combining insect repellent with pollen microcapsules and white petrolatum using supercritical carbon dioxide technology, a three-dimensional composite microcapsule is formed, which solves the problems of easy volatility and poor compatibility of insect repellent and achieves a comprehensive effect of long-lasting insect repellency, safety and UV protection.

CN122123947APending Publication Date: 2026-06-02XIAMEN UNIV
View PDF 0 Cites 0 Cited by

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
XIAMEN UNIV
Filing Date
2026-04-15
Publication Date
2026-06-02

AI Technical Summary

Technical Problem

Existing technologies make it difficult to efficiently and stably combine insect repellents with natural pollen carriers to prepare composite microcapsules with synergistic effects. Furthermore, traditional methods suffer from problems such as the volatility and oxidation of insect repellents and poor compatibility.

Method used

A supercritical carbon dioxide mixing process is used to mix anthelmintic drugs, white petrolatum, and pollen microcapsules under supercritical conditions. By utilizing the solubility and diffusion capacity of CO2, a three-dimensional structure of pollen skeleton-petrolatum sealing layer-anthelmintic drug is formed, achieving efficient drug loading and sustained release.

Benefits of technology

The prepared composite microcapsules significantly prolong the insect repellent effect, with an average repellency time of 10 hours, reducing the risk of skin penetration, and possessing excellent biocompatibility and UV resistance. They are also environmentally friendly and free of chemical residues.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN122123947A_ABST
    Figure CN122123947A_ABST
Patent Text Reader

Abstract

This invention provides a method for preparing and applying a long-acting anthelmintic compound microcapsule. The long-acting anthelmintic compound microcapsule is composed of a component containing an anthelmintic drug, white petrolatum, and pollen microcapsules; the anthelmintic drug content is 10-30 wt% of the total weight. Based on a unique supercritical carbon dioxide mixing process, this invention achieves efficient loading of the anthelmintic agent into the pollen microcapsules under mild conditions. This process further utilizes the porous nature of the microcapsules to achieve sustained release of the anthelmintic agent, thereby effectively prolonging the duration of action. Furthermore, thanks to its micron-sized structure, the microcapsule ensures that the anthelmintic component acts only on the body surface, preventing it from penetrating the skin, thus significantly improving the safety of use.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] This invention relates to a long-acting insect repellent compound microcapsule, its preparation method, and its application, belonging to the field of daily chemical products technology. Background Technology

[0002] Mosquitoes are vectors for many infectious diseases (such as malaria and dengue fever), and chemical repellents are an important means of personal protection. While organic insect repellents such as DEET are highly effective, they suffer from problems such as volatility, short effective time, and skin irritation. Current technology attempts to combine insect repellents with bases such as petroleum jelly to delay volatilization; however, the high melting point of petroleum jelly may cause thermal decomposition of the insect repellent during processing, and the poor compatibility between the two can easily lead to phase separation problems.

[0003] Polymer carriers derived from natural pollen show great potential as carriers of active ingredients due to their porous, hollow structure, biocompatibility, and biodegradability. Their multi-level pore design enables efficient loading and precise controlled release of active substances, while the endogenous bioactive components and loaded molecules form a synergistic stabilizing effect, effectively improving tolerance to photothermal environments. This carrier can reduce the risk of skin penetration while prolonging the duration of protection. Its porous structure provides a large specific surface area, enabling efficient loading of active substances through physical adsorption, and the hollow structure can extend the duration of action of active substances. However, how to efficiently and stably combine insect repellents, petrolatum, and natural pollen carriers to prepare composite microcapsules with synergistic effects remains a technical challenge in this field. Summary of the Invention

[0004] This invention provides a long-acting anthelmintic compound microcapsule, its preparation method, and its application, which can effectively solve the above-mentioned problems.

[0005] This invention provides a long-acting anthelmintic compound microcapsule, which is made of a component containing an anthelmintic drug, white petrolatum and pollen microcapsules; the content of the anthelmintic drug is 10-30 wt% of the total weight; the mass ratio of pollen microcapsules to white petrolatum is 0.2-0.5:1.

[0006] In some embodiments, the anthelmintic is at least one of N,N-diethyl-3-methylbenzamide, 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine, ethyl 3-(N-n-butyl-N-acetyl)-aminopropionate, or (2S)-2-methylpiperidinyl(1S)-3-cyclohexyl, N-(4-ethylphenyl)-2-((4-ethyl-5-(3-pyridyl)-4H-1,2,4-triazol-3-yl)thio)acetamide.

[0007] In some embodiments, the pollen microcapsules are one or more of sunflower pollen, dandelion pollen, corn pollen, wheat pollen, pine pollen, bee pollen, schisandra pollen, or rapeseed pollen.

[0008] In some embodiments, the pollen microcapsules have a particle size of 35-45 μm.

[0009] This invention provides a method for preparing long-acting anthelmintic compound microcapsules, comprising the following steps: S1, add the insect repellent, white petrolatum and pollen microcapsules to the reaction vessel; S2, introduce carbon dioxide into the reactor to bring the pressure up to 8–15 MPa and maintain it in a supercritical state; S3, control the reactor temperature at 35–45℃; mix under magnetic stirring for 0.5–2 h; depressurize to atmospheric pressure at a rate of 0.5–1 MPa / min, and collect the composite microcapsules.

[0010] In some embodiments, the magnetic stirring speed is 200–400 rpm.

[0011] This invention provides an application of the composite microcapsules in skincare, wherein the composite microcapsules are applied directly to the skin surface to provide a long-lasting insect repellent effect.

[0012] This invention provides an application of the composite microcapsules in skincare, using the composite microcapsules for surface treatment of functional textiles or outdoor protective materials.

[0013] This invention provides an application of the aforementioned composite microcapsules in the preparation of skincare products.

[0014] This invention provides a skin care product made from the aforementioned composite microcapsules and skin care product base.

[0015] The beneficial effects of this invention are: The natural pollen microcapsules used in this invention have sporopollenin as the main component of their outer wall. Sporopollenin is a highly cross-linked biopolymer rich in phenolic compounds (such as ferulic acid and p-coumaric acid) in its molecular structure, possessing natural broadband ultraviolet absorption capabilities. After the composite microcapsules are applied to the skin surface, the sporopollenin shell of the pollen microcapsules not only acts as a carrier for the insect repellent but also effectively absorbs and scatters ultraviolet rays (UVB / UVA), thereby achieving long-lasting insect repellency while endowing the composite microcapsules with excellent natural anti-ultraviolet and skin protection effects.

[0016] This invention utilizes a unique supercritical carbon dioxide mixing process to achieve efficient loading of insect repellents into pollen microcapsules under mild conditions. This process further leverages the porous nature of the microcapsules to achieve sustained release of the insect repellent, thereby effectively extending its duration of action.

[0017] This invention ingeniously utilizes supercritical carbon dioxide loading technology to load insecticidal active ingredients while using its high permeability to physically encapsulate and in-situ inactivate sensitizing substances in natural pollen. Combined with the deep sealing of pollen micropores by high molecular weight white petrolatum and the steric hindrance effect of micron-sized particles, the contact path between the natural carrier and the human immune system is blocked at the source, thus achieving excellent biosafety without the need for complex pretreatment.

[0018] The porous structure of the pollen microcapsules of this invention effectively adsorbs insect repellents. Under supercritical CO2 conditions, the physical properties of petrolatum change, allowing it to effectively wet, fill, and coat the surface of the insect repellent-loaded pollen particles, thus delaying the volatilization of the insect repellent. Simultaneously, the shell structure inhibits skin penetration of the insect repellent, reducing the potential risks of long-term use.

[0019] This invention utilizes supercritical CO2 fluid technology for preparation, employing a purely physical mixing process without introducing any organic co-solvents, generating no waste, and achieving a near 100% yield. In contrast, conventional emulsion methods require the extensive use of surfactants, organic solvents, and dispersion media (water). The residues of these chemical auxiliaries may cause skin irritation.

[0020] The composite microcapsules prepared by this invention have an average effective repellency time of up to 10 hours, which is significantly better than commercially available single insect repellent products. Attached Figure Description

[0021] To more clearly illustrate the technical solutions of the embodiments of the present invention, the accompanying drawings used in the embodiments will be briefly introduced below. It should be understood that the following drawings only show some embodiments of the present invention and should not be regarded as a limitation of the scope. For those skilled in the art, other related drawings can be obtained from these drawings without creative effort.

[0022] Figure 1 The images show the actual composite microcapsules; from left to right: composite microcapsule 1 prepared in Example 1, composite microcapsule 2 prepared in Example 2, and composite microcapsule 3 prepared in Example 3.

[0023] Figure 2 These are SEM images of the microcapsules before and after drug loading.

[0024] Figure 3The curves show the weight changes of different formulations.

[0025] Figure 4 The concentration of DEET in mouse blood.

[0026] Figure 5 Image of a stained section of mouse skin.

[0027] Figure 6 This is a statistical graph of mouse skin thickness.

[0028] Figure 7 This is a statistical chart showing the collagen content in mouse skin. Detailed Implementation

[0029] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, 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, not all, of the embodiments of the present invention. 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. Therefore, the following detailed description of the embodiments of the present invention provided in the accompanying drawings is not intended to limit the scope of the claimed invention, but merely to illustrate selected embodiments of the invention.

[0030] This invention provides a long-acting anthelmintic compound microcapsule, which is made of a component containing an anthelmintic drug, white petrolatum and pollen microcapsules; the content of the anthelmintic drug is 10-30 wt% of the total weight; the mass ratio of pollen microcapsules to white petrolatum is 0.2-0.5:1.

[0031] In some embodiments, the anthelmintic is at least one of N,N-diethyl-3-methylbenzamide, 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine, ethyl 3-(N-n-butyl-N-acetyl)-aminopropionate, or (2S)-2-methylpiperidinyl(1S)-3-cyclohexyl, N-(4-ethylphenyl)-2-((4-ethyl-5-(3-pyridyl)-4H-1,2,4-triazol-3-yl)thio)acetamide.

[0032] In some embodiments, the pollen microcapsules are one or more of sunflower pollen, dandelion pollen, corn pollen, wheat pollen, pine pollen, bee pollen, schisandra pollen, or rapeseed pollen.

[0033] Those skilled in the art should understand that the other insect repellents listed above (such as picaridin) also possess similar lipid solubility and supercritical CO2 solubility to DEET; similarly, the other natural pollens listed above (such as pine pollen and bee pollen) all possess similar porous outer wall structures of sporophytin. Therefore, based on the unique supercritical fluid loading and petrolatum sealing principle of this invention, the aforementioned other insect repellents and pollen carriers can also achieve the long-acting sustained release, low-permeability safety, and UV protection effects described in this invention.

[0034] In some embodiments, the pollen microcapsules have a particle size of 35-45 μm.

[0035] This invention provides a method for preparing long-acting anthelmintic compound microcapsules, comprising the following steps: S1, add the anthelmintic drug, white petrolatum and pollen microcapsules to the reaction vessel; the content of the anthelmintic drug is 10-30 wt% of the total weight; the mass ratio of pollen microcapsules to white petrolatum is 0.2-0.5:1.

[0036] S2, carbon dioxide is introduced into the reactor to achieve a pressure of 8–15 MPa and maintain it in a supercritical state. This step, by utilizing carbon dioxide as a green solvent, significantly improves the solubility and dispersibility of the anthelmintic drug, thereby enhancing encapsulation efficiency. Compared with other gases such as nitrogen, helium, and argon, carbon dioxide has better solubility and applicability, effectively promoting the interaction between the drug and the matrix, thus ensuring the uniformity and stability of the microcapsules. Furthermore, its superior diffusion ability in the supercritical state helps to form a uniform drug loading.

[0037] S3, the reactor temperature is controlled at 35–45℃ to promote the interaction between reactants and ensure uniform dispersion of the anthelmintic drug between white petrolatum and microcapsules; mixing is carried out under magnetic stirring for 0.5–2 h to ensure uniform reaction and improve the structural stability of microcapsules; the pressure is released to atmospheric pressure at a rate of 0.5–1 MPa / min, and the composite microcapsules are collected. Slow decompression creates microcavities inside the microcapsules, thereby enhancing the sustained-release performance.

[0038] The ingenuity of this invention lies in its clever utilization of the physical properties of supercritical CO2 to achieve complex micro-encapsulation: in the supercritical state, CO2 carries the drug and petrolatum into the porous hollow structure of pollen; during the depressurization process, petrolatum precipitates and solidifies within the pollen pores, forming a natural "plug" that seals the drug inside the microcapsule. This three-in-one structural design of "skeleton-blocking-active ingredient" makes a significant technological contribution to solving the problems of volatility and oxidation of organic insect repellents.

[0039] The core process of this invention utilizes a supercritical carbon dioxide environment, which inherently possesses strong solvation capabilities: Lipid and protein extraction: Under high pressure at 35–45°C, supercritical CO2 can penetrate the germination pores and cell walls of natural pollen, extracting the sensitizing lipids and some soluble proteins within. Protein denaturation: The high-pressure CO2 environment and the mechanical shear force from pressure changes cause irreversible changes (denaturation) in the quaternary structure of residual proteins in pollen, thereby rendering them inactive and unable to bind to the human immune system. The process of preparing composite microcapsules is, in effect, also a process of "in-situ desensitization" of pollen.

[0040] In this system, white petrolatum is not merely an adjuvant, but also a key component of the physical barrier: Porous channel filling: Under supercritical conditions, liquefied white petrolatum enters the pollen cavity with scCO2. When the system is depressurized back to normal temperature and pressure, the petrolatum "solidifies in situ" within the pollen channels. Complete encapsulation: The solidified petrolatum not only encapsulates the insecticide but also physically "seales" off any remaining allergens inside the pollen. This confines the allergenic proteins within the solid matrix formed by the petrolatum and sporopollenin backbone, preventing them from being released and contacting the skin.

[0041] In some embodiments, the magnetic stirring speed is 200–400 rpm.

[0042] This invention provides an application of the composite microcapsules in skincare, wherein the composite microcapsules are applied directly to the skin surface to provide a long-lasting insect repellent effect.

[0043] This invention provides an application of the composite microcapsules in skincare, using the composite microcapsules for surface treatment of functional textiles or outdoor protective materials.

[0044] This invention provides an application of the aforementioned composite microcapsules in the preparation of skincare products.

[0045] This invention provides a skin care product made from the aforementioned composite microcapsules and skin care product base.

[0046] Example 1 Preparation of long-acting insecticidal compound microcapsules (a) Weigh out 2g of DEET, 3g of white petrolatum, and 5g of natural sunflower microcapsules (particle size approximately 40μm), and add them together to the reaction vessel; (b) Introduce CO2 into the reactor until the pressure inside the reactor reaches 10 MPa and maintain it in a supercritical state; (c) Turn on the metal bath heating to bring the temperature of the reactor to 40 °C; (d) Use magnetic stirring and control the stirring speed at 200 rpm; (e) After the reaction has been going on for 1 hour, CO2 is released through a pressure reducing valve to release the pressure to atmospheric pressure at a rate of 1 MPa / min. The sample in the vessel is collected and named composite microcapsule 1.

[0047] Example 2 Weigh out 2g of DEET, 3g of white petrolatum, and 2.5g of natural sunflower microcapsules. Perform the same procedures as in Example 1. Collect the sample from the vessel and name it Composite Microcapsule 2.

[0048] Example 3 Weigh out 2g of DEET and 3g of white petrolatum. Do not add natural sunflower microcapsules. Perform the same procedures as in Example 1. Collect the sample from the vessel and name it Composite Microcapsule 3.

[0049] Test case 1. Morphological observation Photographs of the composite microcapsules prepared in Examples 1 to 3 are shown below. Figure 1 As shown.

[0050] The composite microcapsules in Example 1 were imaged using scanning electron microscopy (SEM). Figure 2 As can be seen, the surface of the blank microcapsules is smooth, porous, and has a spiky structure. After loading with DEET-Vaseline, a large number of particles appear on the surface, indicating that the drug is stably loaded onto the microcapsules.

[0051] 2. Weight monitoring The composite microcapsules prepared in Examples 1 to 3 were subjected to weight monitoring, and the weight change of the composite microcapsules in air at room temperature and pressure was evaluated using an electronic balance. The results are as follows: Figure 3 As shown, DEET is easily volatilized, with about 30% remaining after 8 hours, while commercially available DEET ointment reduces to 80% of its weight after 12 hours. The DEET loaded in the composite microcapsules can maintain more than 90% of its weight within 48 hours, indicating that the composite microcapsules of the present invention can effectively inhibit the volatilization of DEET.

[0052] The results of the avoidance test are shown in Table 1.

[0053] Table 1

[0054] 3. Encapsulation efficiency and drug loading rate test The test procedure for DEET encapsulation efficiency is as follows: S1, Prepare long-acting insect-repellent compound microcapsules according to Example 1; S2, centrifuge the composite microcapsule suspension at high speed (8000 rpm, 10 minutes) to precipitate the composite microcapsules; S3. Collect the supernatant liquid, measure the absorbance at 287 nm using ultraviolet spectrophotometry, establish a standard curve, and determine the DEET content in the previous liquid. The calculation formula is: (Drug content in carrier / Total dosage) × 100% The steps for testing the DEET loading rate are as follows: S1, Prepare long-acting insect-repellent compound microcapsules according to Example 1; S2, centrifuge the composite microcapsule suspension at high speed (8000 rpm, 10 minutes) to precipitate the composite microcapsules; S3, collect the precipitate of the composite microcapsules and weigh it. Calculate the drug loading rate based on the weight of the blank microcapsules before the reaction. The calculation formula is: (Weight of DEET / Mass of composite microcapsules) × 100% The results of DEET encapsulation efficiency and drug loading rate are shown in Table 2.

[0055] Table 2

[0056] As shown in Table 1, the average effective repellency time of the composite microcapsules prepared in Example 1 was 15.1 h, which is higher than that of commercially available DEET ointment (5.5 h) and DEET-Vaseline ointment (9.1 h). This nearly three-fold increase in long-lasting performance compared to commercially available products and 1.6 times that of the Vaseline-based compound combination exceeds the expected effect of conventional physical mixing. This demonstrates that the pollen microcapsules and Vaseline are not simply superimposed, but rather form a specific "lock-in structure" that significantly inhibits the drug's evaporation rate.

[0057] As shown in Table 2, the composite microcapsules prepared in Example 1 achieve an encapsulation rate of over 90% for the anthelmintic drug, thus ensuring efficient utilization of raw materials and the final performance of the product. Through precise formulation control, the drug loading of this invention can be effectively adjusted within the range of 10-20% to meet different application requirements.

[0058] 4. Security Testing The backs of mice were shaved, and different mosquito repellent creams were applied to their backs. After 24 hours, the concentration of DEET in the mice's blood was measured to evaluate the risk of transdermal absorption. Figure 4 As shown, the composite microcapsule group had significantly lower levels of DEET in the blood compared to the commercially available DEET product group. This result indicates that natural plant microcapsules can effectively reduce the risk of in vivo exposure to DEET and offer better safety.

[0059] Mice that had been coated with the composite microcapsules were euthanized, and their skin tissue was fixed, sectioned, and stained with H&E. Figure 5As can be seen, the microcapsule particles (black circles) are distributed in the stratum corneum and have not entered the skin tissue. The allergenic proteins of natural pollen have lost their physiological basis for functioning, further confirming that they have good biocompatibility.

[0060] Conventional insect repellent products often extend their duration of action by increasing concentration, but this increases the risk of skin irritation. This invention utilizes micron-sized (approximately 40 μm) pollen as a carrier, leveraging its steric hindrance effect—its volume being much larger than skin pores—to achieve a perfect balance between "long-lasting" and "safe." This approach of blocking chemical absorption through physical size limitation represents a significant advancement.

[0061] 5. Verify the UV protection effect of the anti-UV and insect repellent compound microcapsules on mouse skin.

[0062] After hair removal from the backs of healthy mice, a UV-protective and insect-repellent microcapsule compound (compound microcapsule 1) was applied topically before UVB irradiation. The mice were irradiated with UVB once daily for 30 minutes each time for 5 consecutive days. Afterward, the mice were sacrificed, and back skin tissue was collected for H&E staining and Masson's staining. Four different fields of view were randomly selected for each field, and the maximum epidermal thickness and collagen content were measured. Figure 6 As shown, the skin thickness of mice treated with the UV-protective and insect-repellent microcapsule compound was similar to that of normal mice. Figure 7 As shown, the collagen content results indicated that the collagen content of the skin was significantly reduced after exposure to ultraviolet radiation, while the group treated with the anti-UV and insect repellent microcapsules had collagen content consistent with normal skin. These results demonstrate that the anti-UV and insect repellent microcapsules have high UV protection performance.

[0063] This solution does not add any chemical sunscreen agents; it achieves excellent UV protection solely through the carrier itself. Sporopollenin, found in pollen shells, possesses natural UV-resistant properties. The inventors discovered and utilized this characteristic, enabling the product to achieve a high degree of integration (insect repellency + sun protection) in outdoor applications. This solution, utilizing natural materials to achieve multiple protective functions, aligns more closely with the trend of green chemistry compared to complex chemically synthesized products, and possesses outstanding substantive characteristics.

[0064] In summary, this invention utilizes a unique supercritical carbon dioxide mixing process to achieve highly efficient loading of insect repellents into pollen microcapsules under mild conditions. This process further leverages the porous nature of the microcapsules to achieve sustained release of the insect repellent, effectively extending its duration of action. Furthermore, thanks to its micron-sized structure, the microcapsules ensure that the insect repellent components act only on the skin surface, preventing penetration and significantly improving safety.

[0065] The synergistic physical / chemical mechanisms of supercritical CO2, petrolatum, pollen, and insect repellent are as follows: 1. The "deep penetration" effect of supercritical fluids: Supercritical CO2 is not only a green solvent, but it can also significantly reduce the viscosity and surface tension of white petrolatum. In this state, the supercritical fluid, carrying dissolved insect repellent and liquefied petrolatum, can overcome capillary resistance and deeply penetrate the micron- or even nano-sized porous walls and hollow cavities of pollen microcapsules.

[0066] 2. The "In-situ Blocking" and Slow-Release Mechanism of Vaseline: During the depressurization process, as CO2 gas rapidly escapes, white Vaseline solidifies in situ within the porous channels and cavities of the pollen. The solidified Vaseline forms a hydrophobic micro-barrier, not only physically "blocking" the channels but also firmly encapsulating the volatile insecticide within the pollen cavity. This three-dimensional structure of "pollen skeleton - Vaseline blocking layer - insecticide" significantly increases the path and resistance of the insecticide's outward diffusion, achieving an excellent slow-release effect lasting over 15 hours.

[0067] 3. Spatial hindrance ensures "targeted epidermal" safety: Unlike traditional ointments, the active ingredients of this invention are confined to pollen particles at the tens of micrometer (e.g., 40 μm) level. This micrometer-scale size creates a significant steric hindrance effect, preventing the composite microcapsules from penetrating the intercellular spaces of the stratum corneum (typically at the tens of nanometer level), thus strictly isolating the organic insect repellent on the skin surface and fundamentally blocking its transdermal absorption into the bloodstream.

[0068] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the invention by those skilled in the art. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the invention should be included within the scope of protection of the invention.

Claims

1. A long-acting insect-repelling compound microcapsule, characterized in that, It is made of components including an anthelmintic drug, white petrolatum and pollen microcapsules; the anthelmintic drug content is 10-30 wt% of the total weight; the mass ratio of pollen microcapsules to white petrolatum is 0.2-0.5:

1.

2. The long-acting anthelmintic compound microcapsule according to claim 1, characterized in that: The anthelmintic is at least one of N,N-diethyl-3-methylbenzamide, 1-(1-methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine, ethyl 3-(N-n-butyl-N-acetyl)-aminopropionate, or (2S)-2-methylpiperidinyl(1S)-3-cyclohexyl, N-(4-ethylphenyl)-2-((4-ethyl-5-(3-pyridyl)-4H-1,2,4-triazol-3-yl)thio)acetamide.

3. The long-acting anthelmintic compound microcapsule according to claim 1, characterized in that: The pollen microcapsules are one or more of the following: sunflower pollen, dandelion pollen, corn pollen, wheat pollen, pine pollen, bee pollen, schisandra pollen, or rapeseed pollen.

4. The long-acting anthelmintic compound microcapsule according to claim 1, characterized in that: The pollen microcapsules have a particle size of 35-45 μm.

5. A method for preparing the long-acting anthelmintic compound microcapsule according to any one of claims 1 to 4, characterized in that, Includes the following steps: S1, add the anthelmintic drug, white petrolatum and pollen microcapsules to the supercritical carbon dioxide reactor; S2, introduce carbon dioxide into the reactor to bring the pressure up to 8–15 MPa and maintain it in a supercritical state; S3, control the reactor temperature at 35–45℃; mix under magnetic stirring for 0.5–2 h; depressurize to atmospheric pressure at a rate of 0.5–1 MPa / min, and collect the composite microcapsules.

6. The method according to claim 5, characterized in that, The magnetic stirrer operates at a speed of 200–400 rpm.

7. The application of the composite microcapsule according to any one of claims 1 to 4 in skin care, characterized in that, The composite microcapsules are applied directly to the skin surface to provide a long-lasting insect repellent effect.

8. The application of the composite microcapsule according to any one of claims 1 to 4 in skin care, characterized in that, The composite microcapsules are used for surface treatment of functional textiles or outdoor protective materials.

9. The use of the composite microcapsule according to any one of claims 1 to 4 in the preparation of skin care products.

10. A skincare product, characterized in that, Made from the composite microcapsules as described in any one of claims 1 to 4 and skin care product base.