Method for preparing cucurbituril-based metal-organic framework

Abstract

The present invention relates to a method for preparing a cucurbituril-based metal-organic framework and, more specifically, to a method for preparing a cucurbituril-based metal-organic framework by using a cucurbituril and a metal salt to cause temperature and pH changes and thereby induce precipitation in the metal salt. In addition, the present invention relates to a cosmetic composition comprising a cucurbituril-based metal-organic framework prepared by the method.

Description

Method for preparing cucurbituril-based metal-organic frameworks

[0001] The present invention relates to a method for producing a cucurbituril-based metal-organic framework, and more particularly, to a method for producing a cucurbituril-based metal-organic framework by inducing precipitation between a cucurbituril and a metal salt by changing temperature and pH.

[0002] In addition, the present invention relates to a cosmetic composition comprising a cucurbituril-based metal-organic framework manufactured by the above method.

[0003] Glycoluril (=C4H2N4O2=) is a molecule composed of four elements: oxygen, nitrogen, carbon, and hydrogen. Cucurbituril is a molecule made up of several of these molecules linked together like blocks. Cucurbituril is a supramolecule made up of several molecules joined together by weak bonds (hydrogen bonds, electrostatic bonds, van der Waals bonds, etc.) rather than strong bonds (covalent bonds) where atoms share electrons. Cucurbituril is a nanomaterial that is a macrocyclic compound made up of n glycoluril units joined together. It is hydrophilic and has a round structure similar to a pumpkin (Figure 1). Cucurbituril can act as a host and form a host-guest complex with the active substance to encapsulate the active substance. This is known to be achieved through hydrogen bonds and ion-dipole interactions. Cucurbiturils have potential applications in various fields because they can form host-guest complexes and release active substances when certain conditions are met, and the oxygen atoms within cucurbiturils can bind to various metal ions, enabling the formation of various nano-sized frameworks. When cucurbiturils are dissolved in a solution, they self-assemble to form their own shapes. However, their insolubility in solutions other than strongly acidic has been a problem, as research with cucurbiturils requires the ability to freely transform their shapes when dissolved in a solution.

[0004] Metal-organic frameworks (MOFs) are crystalline materials composed of organic linkers and metal ions. They possess an open pore structure and a large internal surface area, making them porous materials capable of transporting large amounts of solvent or molecules. Furthermore, they possess the unique characteristic of allowing pore size to be controlled by varying the composition of the MOFs or the skeletal structure.

[0005] Meanwhile, it is not easy to penetrate the skin with the active ingredients of cosmetics. To address this, active efforts and research are underway to utilize transdermal delivery systems (TDS) in functional cosmetics to stabilize the active ingredients and enhance their percutaneous penetration efficiency.

[0006] The technical task of the present invention is to provide a method for effectively manufacturing a cucurbituril-based metal-organic framework capable of efficiently delivering an active ingredient of a cosmetic into the skin in a stable form.

[0007] In addition, another technical object of the present invention is to provide a cosmetic composition comprising a cucurbituril-based metal-organic framework manufactured by the above method.

[0008] In order to solve the above problem, the present invention,

[0009] (i) Prepare a solution by dissolving cucurbituril in a solvent;

[0010] (ii) Add a metal salt to the solution obtained in the above step (i) and then heat while stirring;

[0011] (iii) Add a base to the solution obtained in step (ii) to increase the pH, then heat while stirring;

[0012] (iv) Cooling the solution obtained in the above step (iii) to room temperature to obtain a crystal;

[0013] (v) A method for producing a cucurbituril-based metal-organic framework is provided, comprising washing the crystal obtained in the above step (iv) to remove a base.

[0014] In addition, in order to achieve the above other objects, the present invention provides a cosmetic composition comprising a cucurbituril-based metal-organic framework manufactured by the above method.

[0015]

[0016] The present invention is described in detail below.

[0017]

[0018] According to one aspect of the present invention,

[0019] (i) Prepare a solution by dissolving cucurbituril in a solvent;

[0020] (ii) Add a metal salt to the solution obtained in the above step (i) and then heat while stirring;

[0021] (iii) Add a base to the solution obtained in step (ii) to increase the pH, then heat while stirring;

[0022] (iv) Cooling the solution obtained in the above step (iii) to room temperature to obtain a crystal;

[0023] (v) A method for producing a cucurbituril-based metal-organic framework is provided, comprising washing the crystal obtained in the above step (iv) to remove a base.

[0024]

[0025] In step (i) of the method for producing a cucurbituril-based metal-organic framework according to the present invention, a solution is prepared by dissolving cucurbituril in a solvent.

[0026] Cucurbiturils are commonly written as “cucurbit[n]uril,” where n is the number of glycoluril units. Cucurbiturils are commercially available and there are no specific restrictions on their use.

[0027] In one specific embodiment according to the present invention, the solvent may be selected from purified water, ethanol, dipropylene glycol, and mixtures thereof, but is not limited thereto.

[0028] In another specific embodiment according to the present invention, 0.001 to 0.1 parts by weight of cucurbituril may be dissolved per 1 part by weight of solvent, but is not limited thereto.

[0029]

[0030] In step (ii) of the method for producing a cucurbituril-based metal-organic framework according to the present invention, a metal salt is added to the solution obtained in step (i) and then heated while stirring.

[0031] In another specific example according to the present invention, the metal salt may be, but is not limited to, AlCl3·6H2O or NaCl.

[0032] In another specific example according to the present invention, the metal salt may be used in an amount of 0.5 to 2 parts by weight relative to 1 part by weight of cucurbituril, but is not limited thereto.

[0033] In another specific embodiment according to the present invention, the stirring in step (ii) may be performed at a speed of, but not limited to, 200 to 600 rpm, 250 to 550 rpm, or 300 to 500 rpm.

[0034] In another specific embodiment according to the present invention, the heating in step (ii) may be performed at a temperature of, but not limited to, 80 to 95°C.

[0035]

[0036] In step (iii) of the method for producing a cucurbituril-based metal-organic framework according to the present invention, a base is added to the solution obtained in step (ii) to increase the pH, and then the solution is heated while stirring.

[0037] In another specific embodiment according to the present invention, the base may be, but is not limited to, NaOH or KOH.

[0038] In another specific embodiment according to the present invention, the amount of the base used can be appropriately adjusted by a person skilled in the art to provide a pH change that allows the formation of a cucurbituril-based metal-organic framework, and there is no special limitation thereto.

[0039] In another specific embodiment according to the present invention, the stirring in step (iii) may be performed at a speed of, but not limited to, 600 to 1,000 rpm, 650 to 950 rpm, or 600 to 900 rpm.

[0040] In another specific embodiment according to the present invention, the heating in step (iii) may be performed at a temperature of, but not limited to, 80 to 95°C.

[0041]

[0042] In step (iv) of the method for producing a cucurbituril-based metal-organic framework according to the present invention, the solution obtained in step (iii) is cooled to room temperature (15 to 25°C) to obtain a crystal.

[0043] In another embodiment according to the present invention, the cooling in step (iv) is performed slowly for at least 24 hours, for example, 24 to 72 hours, 24 to 60 hours or 24 to 48 hours.

[0044] In another specific embodiment according to the present invention, filtering may be performed to obtain a crystal after cooling, but is not limited thereto.

[0045]

[0046] In step (v) of the method for producing a cucurbituril-based metal-organic framework according to the present invention, the crystal obtained in step (iv) is washed to remove the base.

[0047] In another specific embodiment according to the present invention, the washing in step (v) may be performed with ethanol, but is not limited thereto.

[0048]

[0049] In another specific embodiment according to the present invention, the method for producing a cucurbituril-based metal-organic framework may further include the step of (vi) adding the crystals and active ingredient obtained in step (v) to a solvent to dissolve them, then separating the supernatant by centrifugation and drying to obtain a powder.

[0050] In another specific embodiment according to the present invention, the active ingredient may be at least one selected from the group consisting of a moisturizer, a whitening agent, an anti-wrinkle agent, a sunscreen, a hair tonic, a vitamin or a derivative thereof, an amino acid or peptide, an anti-inflammatory agent, an acne treatment agent, a bactericidal agent, a female hormone agent, an exfoliating agent, and a natural product, but is not limited thereto.

[0051] Humectants include, but are not limited to, creatine, polyglutamic acid, sodium lactate, hydrolyzed proline, sodium 2-pyrrolidone-5-carboxylate, hyaluronic acid, sodium hyaluronate, ceramides, phytosteryls, cholesterol, sitosterol, pullulan, proteoglycans, etc. Whitening agents include, but are not limited to, arbutin and arbutin derivatives, kojic acid, bisabolol, niacinamide, vitamin C and vitamin C derivatives, placenta, allantoin, tranexamic acid, etc. Anti-wrinkle agents include, but are not limited to, retinol, retinol derivatives, adenosine, licorice extract, red ginseng extract, ginseng extract, etc. Sunscreens include, but are not limited to, benzophenone derivatives, para-aminobenzoic acid derivatives, methoxycinnamic acid derivatives, salicylic acid derivatives, etc. There are no special restrictions on hair growth agents, but blood circulation promoters and / or local irritants are preferred. Blood circulation promoters include, but are not limited to, extracts of the Korean ginseng root, cephalantin, vitamin E and its derivatives, gamma oryzanol, etc., and local irritants include, but are not limited to, red pepper tincture, ginger tincture, cantharis tincture, nicotinic acid benzyl ester, etc. As vitamins or their derivatives, examples thereof include, but are not limited to, vitamin A (retinol) and its derivatives, vitamins B1, B2, B6, vitamin E and its derivatives, vitamin D, vitamin H, vitamin K, pantothenic acid and its derivatives, biotin, panthenol, coenzyme Q. 10, idebenone, etc., but are not limited thereto. Amino acids or peptides include, for example, cysteine, methionine, serine, lysine, tryptophan, amino acid extracts, epidermal growth factor (EGF), insulin-like growth factor (IGF), fibroblast growth factor (FGF), Kupffer peptide, Kupffer tripeptide-1, tripeptide-29, tripeptide-1, acetyl hexapeptide-8, nicotinoyl tripeptide-35, hexapeptide-12, hexapeptide-9. Examples include, but are not limited to, palmitoyl pentapeptide-4, palmitoyl tetrapeptide-7, palmitoyl tripeptide-29, palmitoyl tripeptide-1, nonapeptide-7, tripeptide-10 citrulline, sh-polypeptide-15, palmitoyl tripeptide-5, diaminopropioyl tripeptide-33, r-spider polypeptide-1, etc. Anti-inflammatory agents include, but are not limited to, beta-glycyrrhizic acid, glycyrrhizic acid derivatives, aminocaproic acid, hydrocortisone, beta-glucan, licorice, etc. Acne treatments include, but are not limited to, estradiol, estrogen, ethinyl estradiol, triclosan, azelaic acid, etc. Examples of antiseptics include, but are not limited to, benzalkonium chloride and benzethonium chloride. There are no specific restrictions on female hormones, but estrogen is suitable, and estradiol, ethinyl estradiol, and isoflavones, which are plant estrogens, are preferable. Examples of exfoliating and dissolving agents include, but are not limited to, sulfur, salicylic acid, alpha hydroxy acid (AHA), beta hydroxy acid (BHA), and resorcin.Extracts of natural products or ingredients obtained from them, such as extracts of Korean ginseng, common angelica, white chrysanthemum, rhubarb, licorice, aloe, chamomile, rosehip, horse chestnut, ginseng, loofah, cucumber, laver, seaweed, hemp, snail, young lady, and centella asiatica, as well as hinokitiol and beta-carotene, are not limited thereto. In addition, there are yeast extracts, collagen, elastin, DHA, EPA, and fragrance ingredients.

[0052] In another specific embodiment according to the present invention, the solvent of step (vi) may be selected from, but is not limited to, purified water, ethanol and mixtures thereof.

[0053]

[0054] In the present invention, in order to enhance the stability of the active ingredient, a metal-organic framework having a large surface area is prepared based on a porous material, cucurbituril, to encapsulate the active ingredient, thereby enhancing the stability of the active ingredient and significantly improving the percutaneous penetration rate.

[0055]

[0056] According to another aspect of the present invention, a cosmetic composition comprising a cucurbituril-based metal-organic framework prepared by the above method is provided.

[0057] The cosmetic composition of the present invention may be formulated into various products such as toner, emulsion, body lotion, cream, essence, ampoule, BB (blemish balm) cream, etc., but is not limited thereto. The cosmetic composition of the present invention may include various contents of cucurbituril-based metal-organic framework according to the needs of the formulation, and for example, may include cucurbituril-based metal-organic framework in an amount of 0.1 to 50 wt%.

[0058] According to the present invention, a cucurbituril-based metal-organic framework can be manufactured with high production efficiency, and the cucurbituril-based metal-organic framework manufactured according to the present invention can efficiently deliver an active ingredient into the skin in a stable form.

[0059] Figure 1 is a model of a cucurbituril having various numbers of glycoluril units.

[0060] FIG. 2 is a photograph showing the properties of the cucurbituril-based metal-organic framework of Example 1 and the cucurbituril-based metal-organic framework containing retinal of Example 2.

[0061] Figure 3 is a photograph of a cucurbituril, a cucurbituril-based metal-organic framework of Example 1, and a cucurbituril-based metal-organic framework containing retinal of Example 2, taken using a scanning electron microscope (SEM) ((A): cucurbituril, (B): Example 1, (C): Example 2).

[0062] Figure 4 shows the results of FT-IR analysis of cucurbituril, the cucurbituril-based metal-organic framework of Example 1, and the cucurbituril-based metal-organic framework containing retinal of Example 2 (CB-MOF: Example 1, CB-MOF (RA): Example 2).

[0063] Figure 5 shows the XRD analysis results of cucurbituril, the cucurbituril-based metal-organic framework of Example 1, retinal, and the cucurbituril-based metal-organic framework containing retinal of Example 2 (CB-MOF: Example 1, CB-MOF (RA): Example 2).

[0064] Figure 6 shows a cucurbituril, a cucurbituril-based metal-organic framework of Example 1, retinal, and a cucurbituril-based metal-organic framework containing retinal of Example 2. 1 This is the result of H NMR analysis (CB-MOF: Example 1, CB-MOF (RA): Example 2).

[0065] Figure 7 is a graph showing the results of HPLC measurement of retinal content in a typical liposome containing retinal and a liposome using a cucurbituril-based metal-organic framework containing retinal of Example 2 (CB-MOF(RA): liposome A, Retinal: liposome B).

[0066] Hereinafter, the present invention will be described in more detail through examples. However, the following examples are provided merely to aid understanding of the present invention and are not intended to limit the scope of the present invention.

[0067]

[0068] Example 1: Preparation of a cucurbituril-based metal-organic framework (cucurbituril-MOF, CB-MOF)

[0069] A cucurbituril-based metal-organic framework was manufactured by dissolving a metal salt, AlCl3·6H2O (Daejung Chemicals & Metals Co. Ltd., Korea), in a solution containing cucurbituril, then adding NaOH (Duksan Pure Chemicals Co. Ltd., Korea) to change the pH and gradually lower the temperature from a high temperature of 80°C or higher to room temperature, thereby inducing precipitation between the metal salts.

[0070] Cucurbituril was Cucurbit[6]uril hydrate (Sigma-Aldrich, USA) containing six glycoluril units. As shown in Table 1, cucurbituril was added to purified water at room temperature while stirring at a speed of at least 300 to 350 rpm, and cucurbituril was sufficiently dissolved until the solution became translucent to opaque milky white. After adding metal salt AlCl3·6H2O to the solution containing cucurbituril, it was heated to 80 to 95°C while stirring at a speed of 700 to 800 rpm. 1 M NaOH was added to the solution containing cucurbituril and metal salt, heated to 80 to 95°C, and stirred at a speed of 700 to 800 rpm. When the solution became transparent and colorless to yellow, heating and stirring were stopped, and the temperature was slowly lowered to room temperature (15 to 25°C). After at least 24 hours, crystals were obtained. Afterwards, a washing process was performed to remove the remaining NaOH. First, the solution containing CB-MOF was filtered using a depressurized filter, which is a funnel-shaped glass filter, to obtain CB-MOF crystals. Next, the pressure was reduced, and the CB-MOF filtered on the filter was washed with ethanol at least twice. Then, the CB-MOF remaining on the filter was dried at atmospheric pressure or under vacuum to obtain white to beige crystals.

[0071] [Table 1]

[0072]

[0073]

[0074] Example 2: Preparation of a cucurbituril-based metal-organic framework (CB-MOF(RA)) containing retinal

[0075] Based on the results of Example 1, a cucurbituril-based metal-organic framework containing retinal was prepared with the composition shown in Table 2. Retinal was added to ethanol, dissolved, and stirred with CB-MOF at room temperature for one day. To obtain a powder, the supernatant was separated using a centrifuge, then ethanol was added, centrifuged once, and the supernatant was separated. Then, CB-MOF (RA) was obtained in powder form through a vacuum drying process for one day.

[0076] [Table 2]

[0077]

[0078]

[0079] Example 3: Preparation of CB-MOF containing a moisturizer

[0080] A CB-MOF containing a moisturizer was prepared in the same manner as Example 2 with the components and compositions shown in Table 3 below.

[0081] [Table 3]

[0082]

[0083]

[0084] Example 4: Preparation of CB-MOF containing whitening agent 1

[0085] A CB-MOF containing a whitening agent was manufactured in the same manner as Example 2 with the components and composition of Table 4 below.

[0086] [Table 4]

[0087]

[0088]

[0089] Example 5: Preparation of CB-MOF containing whitening agent 2

[0090] A CB-MOF containing a whitening agent was manufactured in the same manner as Example 2 using the components and composition of Table 5 below.

[0091] [Table 5]

[0092]

[0093]

[0094] Example 6: Preparation of CB-MOF containing a sunscreen agent

[0095] A CB-MOF containing a sunscreen was manufactured using the same method as Example 2 with the components and composition of Table 6 below.

[0096] [Table 6]

[0097]

[0098]

[0099] Example 7: Preparation of CB-MOF containing vitamins

[0100] A CB-MOF containing vitamins was manufactured in the same manner as Example 2 using the components and compositions in Table 7 below.

[0101] [Table 7]

[0102]

[0103]

[0104] Example 8: Preparation of CB-MOF containing amino acids

[0105] A CB-MOF containing amino acids was manufactured using the same method as Example 2 with the components and composition of Table 8 below.

[0106] [Table 8]

[0107]

[0108]

[0109] Example 9: Preparation of CB-MOF containing peptide

[0110] A CB-MOF containing a peptide was prepared in the same manner as Example 2 using the components and composition of Table 9 below.

[0111] [Table 9]

[0112]

[0113]

[0114] Example 10: Preparation of CB-MOF containing an anti-inflammatory agent

[0115] A CB-MOF containing an anti-inflammatory agent was manufactured using the same method as Example 2 with the components and composition of Table 10 below.

[0116] [Table 10]

[0117]

[0118]

[0119] Example 11: Preparation of CB-MOF containing acne treatment agent

[0120] A CB-MOF containing an acne treatment agent was manufactured using the same method as Example 2 with the components and composition of Table 11 below.

[0121] [Table 11]

[0122]

[0123]

[0124] Example 12: Preparation of CB-MOF containing a bactericide

[0125] A CB-MOF containing a sterilizing agent was prepared in the same manner as Example 2 with the components and composition of Table 12 below.

[0126] [Table 12]

[0127]

[0128]

[0129] Example 13: Preparation of CB-MOF containing natural extracts

[0130] A CB-MOF containing a natural extract was manufactured using the same method as Example 2 with the components and composition of Table 13 below.

[0131] [Table 13]

[0132]

[0133]

[0134] Example 14: Preparation of CB-MOF containing retinol (CB-MOF(RO))

[0135] A CB-MOF containing retinol was prepared in the same manner as Example 2 with the components and composition of Table 14 below.

[0136] [Table 14]

[0137]

[0138]

[0139] Experimental Example 1: Scanning Electron Microscope Observation

[0140] In order to confirm the surface morphology of the CB-MOF of Example 1 and the CB-MOF(RA) of Example 2, the samples were coated with platinum (Pt) as a sample pretreatment process and then measured using an FEI Inspect F-Scanning Electron Microscope (FEI, USA). As can be seen in Fig. 3, unlike cucurbituril, the CB-MOF of Example 1 showed a regular triangular pyramidal shape, and the CB-MOF(RA) of Example 2, which encapsulated retinal, showed no significant change in shape compared to the CB-MOF of Example 1.

[0141]

[0142] Experimental Example 2: Fourier-transform infrared spectroscopy (FT-IR) measurement

[0143] In order to confirm the composition and structure of the CB-MOF of Example 1 and the CB-MOF(RA) of Example 2, measurements were performed using a Nicolet iS10 FT-IR Spectrometer (Thermo Fisher Scientific, USA). As can be seen in Fig. 4, the CB-MOF of Example 1 showed a peak shape similar to that of cucurbituril in a certain range, indicating that the metal-organic framework was maintained without a significant change in the crystal phase. In addition, the similarity in the peak shapes of the CB-MOF of Example 1 and the CB-MOF(RA) of Example 2 indicated that the CB-MOF(RA) of Example 2 was maintained without a significant change in the crystal phase even after encapsulating retinal.

[0144]

[0145] Experimental Example 3: High-power powder X-ray diffraction measurements

[0146] In order to confirm the composition and structure of the CB-MOF of Example 1 and the CB-MOF(RA) of Example 2, measurements were made using D / max-2500 / PC -Powder X-ray diffraction (Rigaku, Japan). The analysis conditions were Cu Kα radiation (λ= 1.54059Å, 40 kV, 200 mA) in the range of 10˚ to 90˚, and a scan rate of 2˚ per minute. As can be seen in Fig. 5, the peaks of the cucurbituril and the CB-MOF of Example 1 showed different patterns, indicating that a change in the crystal phase occurred. When the crystallinity of the CB-MOF(RA) of Example 2 was compared with that of the CB-MOF of Example 1, no peak change occurred, indicating that the encapsulation of retinal did not affect the crystallinity. Additionally, it was confirmed that retinal was successfully encapsulated inside the CB-MOF, as no retinal peak was observed in the CB-MOF (RA) of Example 2.

[0147]

[0148] Experimental Example 4: Nuclear Magnetic Resonance Spectroscopy Measurements

[0149] To confirm the formation of CB-MOF in Example 1 and the encapsulation of retinal in CB-MOF(RA) in Example 2, the samples were pretreated using 0.5 mL of DMSO-d6 each, and then analyzed using DD2 600 MHz FT NMR (Agilent Technologies, USA). 1 H NMR was measured. As can be seen in Fig. 6, when comparing cucurbituril and the CB-MOF of Example 1, a new peak appeared in the CB-MOF of Example 1, indicating that the CB-MOF of Example 1 was successfully formed. In the CB-MOF (RA) of Example 2, a distinct retinal peak was confirmed, indicating that retinal encapsulation was successfully achieved in the CB-MOF (RA) of Example 2.

[0150]

[0151] Experimental Example 5: Retinal Content Analysis and Stability Evaluation

[0152] In order to evaluate the initial content and content retention rate of retinal in the CB-MOF (RA) of Example 2, liposomes (liposome A) containing the CB-MOF (RA) of Example 2 and general liposomes (liposome B) were prepared with the compositions in Table 15 below, and then stored at room temperature for 3 months. The retinal content was measured by high-performance liquid chromatography (HPLC), and the results are shown in Fig. 7. As can be seen in Fig. 7, when the retinal content was compared after 3 months, the non-encapsulated retinal maintained 85% of the initial content, and the retinal in the CB-MOF (RA) of Example 2 was maintained at more than 90%. That is, it was confirmed that the cucurbituril-based metal-organic framework can encapsulate retinal, which is unstable in the external environment, to increase the stability of retinal.

[0153] [Table 15]

[0154]

Claims

1. (i) Prepare a solution by dissolving cucurbituril in a solvent; (ii) Add a metal salt to the solution obtained in the above step (i) and then heat while stirring; (iii) Add a base to the solution obtained in step (ii) to increase the pH, then heat while stirring; (iv) Cooling the solution obtained in the above step (iii) to room temperature to obtain a crystal; (v) A method for producing a cucurbituril-based metal-organic framework, comprising washing the crystal obtained in the above step (iv) to remove a base.

2. A method for producing a cucurbituril-based metal-organic framework, characterized in that the solvent of step (i) is selected from purified water, ethanol, dipropylene glycol, and mixtures thereof in the first paragraph.

3. A method for producing a cucurbituril-based metal-organic framework, characterized in that the metal salt of step (ii) in paragraph 1 is AlCl3·6H2O or NaCl.

4. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (ii) of paragraph 1, stirring is performed at a speed of 200 to 600 rpm.

5. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (ii) of paragraph 1, heating is performed at a temperature of 80 to 95°C.

6. A method for producing a cucurbituril-based metal-organic framework, characterized in that the base in paragraph 1 is NaOH or KOH.

7. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (iii) of paragraph 1, stirring is performed at a speed of 600 to 1,000 rpm.

8. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (iii) of paragraph 1, heating is performed at a temperature of 80 to 95°C.

9. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (iv), cooling is performed for at least 24 hours.

10. A method for producing a cucurbituril-based metal-organic framework, characterized in that in step (v) of paragraph 1, washing is performed with ethanol.

11. A method for producing a cucurbituril-based metal-organic framework, characterized in that, in the first paragraph, (vi) the crystals and active ingredient obtained in the step (v) are added to a solvent to dissolve them, and then the supernatant is separated by centrifugation and dried to obtain a powder.

12. A method for producing a cucurbituril-based metal-organic framework, characterized in that the active ingredient in claim 11 is at least one selected from the group consisting of a moisturizer, a whitening agent, an anti-wrinkle agent, a UV blocker, a hair tonic, a vitamin or a derivative thereof, an amino acid or a peptide, an anti-inflammatory agent, an acne treatment agent, a bactericidal agent, a female hormone agent, an exfoliating agent, and a natural product.

13. A method for producing a cucurbituril-based metal-organic framework, characterized in that the solvent is selected from purified water, ethanol, and a mixture thereof, in accordance with claim 11.

14. A cosmetic composition comprising a cucurbituril-based metal-organic framework prepared by the method of any one of claims 11 to 13.

15. A cosmetic composition according to claim 14, characterized in that it comprises 0.1 to 50 wt% of a cucurbituril-based metal-organic framework.

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