Ceramide-conjugated hyaluronic acid hydrogel

Abstract

One aspect of the present disclosure relates to a hyaluronic acid hydrogel to which ceramide is bound.SOLUTION: One aspect of the present disclosure includes a hyaluronic acid hydrogel containing hyaluronic acid or a salt thereof, and emulsified particles bound to the hyaluronic acid hydrogel, wherein the emulsified particles contain at least one of a ceramide or a pseudoceramide. [Advantageous Effects] According to an aspect of the present invention, it is possible to provide a composition, particularly a composition of a solubilized formulation, which stably contains both ceramide and hyaluronic acid by simply mixing a hyaluronic acid hydrogel to which ceramide is bound.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims priority to Korean Patent Application No. 10-2024-0082048, filed on June 24, 2024, the entire specification of which is incorporated herein by reference.

[0002] The present disclosure relates to ceramide-conjugated hyaluronic acid hydrogels. [Background technology]

[0003] Hyaluronic acid is known as a material with excellent moisturizing properties and hydrophilicity, and cross-linked hyaluronic acid hydrogels, in particular, are characterized by their excellent moisturizing properties. Ceramides are a major skin component that strengthens the skin's barrier function, and various ceramides are found in human skin. Ceramides have relatively few hydrophilic groups, so they exhibit strong hydrophobic interactions within the skin. This structural feature allows them to exert a unique skin barrier function by preventing water loss from the body and blocking the influx of harmful substances from the outside through the skin. Therefore, incorporating ceramides into cosmetics significantly improves moisturizing power and skin protection, thereby significantly contributing to improving the quality of cosmetics.

[0004] Thus, various researches have been carried out to prepare a composition that contains both components that provide skin with moisturizing power.Conventionally, to prepare a composition that contains both ceramide and hyaluronic acid, mainly, i) a method of dispersing ceramide in hyaluronic acid using an emulsification process, and ii) a method of chemically crosslinking ceramide and hyaluronic acid have been used.In the case of the above i), the final preparation becomes an emulsion preparation, so there is a problem that it becomes cloudy, which impairs the appearance, and makes it difficult to apply as a solubilized preparation.In the case of an emulsion preparation, there is a possibility that dispersed ceramide particles will aggregate with each other.In the case of the above ii), there is a drawback that a crosslinker of equal or more moles than ceramide is required for chemical bonding, and an organic solvent-based reaction process and purification process are necessary. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent Registration No. 1175193 Summary of the Invention [Problem to be solved by the invention]

[0006] One aspect of the present disclosure aims to provide a ceramide-conjugated hyaluronic acid hydrogel.

[0007] One aspect of the present disclosure aims to provide a composition comprising the ceramide-bound hyaluronic acid hydrogel.

[0008] One aspect of the present disclosure aims to provide a method for producing a ceramide-conjugated hyaluronic acid hydrogel.

[0009] One aspect of the present disclosure aims to provide a method for producing a composition comprising the ceramide-bound hyaluronic acid hydrogel. [Means for solving the problem]

[0010] A ceramide-conjugated hydrogel composition according to one aspect of the present disclosure comprises: a hyaluronic acid hydrogel containing hyaluronic acid or a salt thereof; and emulsifying particles bound to the hyaluronic acid hydrogel, The emulsified particles include at least one of ceramide or pseudoceramide.

[0011] A composition according to one embodiment of the present disclosure includes a ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure.

[0012] A method for producing a ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present disclosure includes the steps of: (a) mixing at least one of ceramide or pseudoceramide, an emulsifier, and water to produce a ceramide emulsion composition; (b) mixing the prepared ceramide emulsion composition with at least one of hyaluronic acid or a hyaluronate, and a crosslinker to obtain a hyaluronic acid hydrogel to which ceramide emulsion particles containing at least one of ceramide or pseudoceramide are bound.

[0013] A method for producing a composition according to one aspect of the present disclosure comprises mixing a ceramide-conjugated hyaluronic acid hydrogel according to one aspect of the present disclosure with purified water. [Effects of the Invention]

[0014] By using the ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present invention, it is possible to provide a composition, particularly a solubilized formulation, that stably contains ceramide (or pseudoceramide) and hyaluronic acid (or a salt thereof).

[0015] The ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present invention can provide a composition that stably contains both ceramide and hyaluronic acid gel at the same time by simply adding it to an aqueous phase formulation that is free of oil and emulsifiers.

[0016] The composition containing the ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present invention can exhibit a transparent appearance, thereby enhancing user satisfaction with the appearance, whereas the composition of an emulsion preparation in which ceramide is emulsified in hyaluronic acid exhibits a white, suspended appearance rather than a transparent appearance.

[0017] A composition containing a hydrogel composition containing a ceramide according to one embodiment of the present invention can exhibit excellent moisturizing power and a pleasant feeling when used. [Brief explanation of the drawings]

[0018] [Figure 1]FIG. 1 is a schematic diagram showing an example of a form in which ceramide is bound to a hyaluronic acid hydrogel according to one embodiment of the present invention. [Figure 2] 1 is a micrograph of a ceramide-conjugated hyaluronic acid hydrogel according to an example. [Figure 3] 1 is a confocal microscope photograph of a ceramide-conjugated hyaluronic acid hydrogel according to an example. [Figure 4] 1 is a photograph comparing the appearance of a composition containing a ceramide-bound hyaluronic acid hydrogel according to an example with the appearance of a composition in which hyaluronic acid and ceramide are emulsified. [Figure 5] 1 is a graph comparing the moisturizing power of a composition containing a ceramide-bound hyaluronic acid hydrogel according to an embodiment with the moisturizing power of a composition emulsified with hyaluronic acid and ceramide. DETAILED DESCRIPTION OF THE INVENTION

[0019] The various examples and terms used in this specification should not be understood to limit the technology described herein to a particular example, but should be understood to include various modifications, equivalents, or alternatives to the example.

[0020] The present inventors have developed a hyaluronic acid hydrogel containing a high content of ceramide by binding ceramide-containing emulsified particles to the hyaluronic acid hydrogel, and have confirmed that by using the ceramide-bound hyaluronic acid hydrogel, a composition containing both ceramide (or pseudoceramide) and hyaluronic acid (or a salt thereof) in a stable manner can be produced by a simple mixing operation without an emulsification step.

[0021] Ceramide-conjugated hyaluronic acid hydrogels In one aspect of the present disclosure, there is provided a ceramide-bound hyaluronic acid hydrogel, comprising a hyaluronic acid hydrogel containing hyaluronic acid or a salt thereof and emulsified particles bound to the hyaluronic acid hydrogel, wherein the emulsified particles contain at least one of ceramide or pseudoceramide.

[0022] The term "hydrogel" in the present disclosure may refer to a structure formed by crosslinking hydrophilic polymers with covalent or non-covalent bonds. In this case, the structure may be a three-dimensional network structure. Due to the hydrophilicity of the constituent materials, hydrogels can absorb and swell large amounts of water in aqueous solutions and environments, but may not dissolve due to the crosslinked structure.

[0023] The ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present disclosure may be one in which ceramide, which is known to be poorly soluble, is physically and / or chemically stabilized. In one embodiment, the ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present disclosure may be one in which ceramide is bound to a hydrogel containing hyaluronic acid or a salt thereof, thereby physically and / or chemically stabilizing the ceramide. In one embodiment, the ceramide or pseudoceramide is uniformly distributed in the hyaluronic acid hydrogel according to one embodiment of the present disclosure.

[0024] In one embodiment, emulsified particles containing at least one of ceramide or pseudoceramide may be bound to a hydrogel containing the hyaluronic acid or a salt thereof.

[0025] In one implementation, the bond may include, but is not limited to, at least one of a physical bond or a chemical bond. In one implementation, the bond may include, but is not limited to, at least one of a physical bond or a chemical bond.

[0026] In one embodiment, the binding of a first component to a second component may mean that the first component is disposed or located on at least a portion of the second component, that the first component is disposed or located on at least a portion of the interior and / or surface of the second component, that the first component is disposed or located in contact with at least a portion of the second component, or that the first component is disposed or located in contact with at least a portion of the interior and / or surface of the second component.

[0027] In one embodiment, the emulsified particles bound to the hyaluronic acid hydrogel may be emulsified particles disposed or located on at least a portion of the hyaluronic acid hydrogel, or may be emulsified particles disposed or located on at least a portion of the interior and / or surface of the hyaluronic acid hydrogel. In one embodiment, the emulsified particles bound to the hyaluronic acid hydrogel may be emulsified particles disposed or located in contact with at least a portion of the hyaluronic acid hydrogel, or may be emulsified particles disposed or located in contact with at least a portion of the interior and / or surface of the hyaluronic acid hydrogel.

[0028] In one embodiment, the ceramide-bound hyaluronic acid hydrogel may have ceramide located or disposed at least partially within the hyaluronic acid hydrogel, or may have ceramide located or disposed at least partially within and / or on the surface of the hyaluronic acid hydrogel, and the hyaluronic acid hydrogel may further contain, without limitation, other components in addition to ceramide.

[0029] In one embodiment, the ceramide-bound hyaluronic acid hydrogel may have the ceramide located or disposed in contact with at least a portion of the hyaluronic acid hydrogel, or may have the ceramide located or disposed in contact with at least a portion of the interior and / or surface of the hyaluronic acid hydrogel, and the hyaluronic acid hydrogel may further contain, without limitation, other components in addition to the ceramide.

[0030] In one implementation, the binding may be, but is not limited to, capture.

[0031] In the present disclosure, the term "entrapment" may mean capturing a specific component, and "a first component entrapped in a second component" may mean that the first component is collected in the second component. For example, when a first component (e.g., an emulsified particle according to one embodiment of the present disclosure) is entrapped in a second component (e.g., a hydrogel comprising hyaluronic acid or a salt thereof according to one embodiment of the present disclosure), the first component may be disposed or located within or on at least a portion of the interior and / or surface of the second component, or the first component may be disposed or located in contact with at least a portion of the interior and / or surface of the second component. When a first component is entrapped in a second component, it is not limited to the first component being surrounded by the second component.

[0032] FIG. 1 is a schematic diagram showing an example of a form in which ceramide is bound to a hyaluronic acid hydrogel according to one embodiment.

[0033] In one embodiment, the ceramide-bonded hyaluronic acid hydrogel may contain 0.1 to 10 wt% of hyaluronic acid or its salt relative to the total weight of the ceramide-bonded hyaluronic acid hydrogel, but is not limited thereto. For example, the ceramide-bonded hyaluronic acid hydrogel may contain 0.1 wt% or more, 0.5 wt% or more, 1 wt% or more, 1.5 wt% or more, 2 wt% or more, 2.5 wt% or more, 3 wt% or more, 3.5 wt% or more, 4 wt% or more, 4.5 wt% or more, 5 wt% or more, 5.5 wt% or more, 6 wt% or more, 6.5 wt% or more, 7 wt% or more, 7.5 wt% or more, 8 wt% or more, 8.5 wt% or more, 9 wt% or more, 9.5 wt% or more, or The content may be 10% by weight or more, or may be 0.1% by weight or less, 0.5% by weight or less, 1% by weight or less, 1.5% by weight or less, 2% by weight or less, 2.5% by weight or less, 3% by weight or less, 3.5% by weight or less, 4% by weight or less, 4.5% by weight or less, 5% by weight or less, 5.5% by weight or less, 6% by weight or less, 6.5% by weight or less, 7% by weight or less, 7.5% by weight or less, 8% by weight or less, 8.5% by weight or less, 9% by weight or less, 9.5% by weight or less, 10% by weight or less, or any combination thereof, but is not limited to these.

[0034] In one embodiment, the ceramide-bonded hyaluronic acid hydrogel may contain at least one of ceramide or pseudoceramide in an amount of 0.01 to 10 wt % relative to the total weight of the ceramide-bonded hyaluronic acid hydrogel, but is not limited thereto. For example, the ceramide-bonded hyaluronic acid hydrogel may contain at least one of ceramide or pseudoceramide in an amount of 0.01 wt % or more, 0.05 wt % or more, 0.1 wt % or more, 0.15 wt % or more, 0.18 wt % or more, 0.19 wt % or more, 0.2 wt % or more, 0.22 wt % or more, 0.23 wt % or more, 0.3 wt % or more, relative to the total weight of the ceramide-bonded hyaluronic acid hydrogel. Amount% or more, 0.4 weight% or more, 0.5 weight% or more, 1 weight% or more, 1.5 weight% or more, 2 weight% or more, 2.5 weight% or more, 3 weight% or more, 3.5 weight% or more, 4 weight% or more, 4.5 weight% or more, 5% by weight or more, 5.5% by weight or more, 6% by weight or more, 6.5% by weight or more, 7% by weight or more, 7.5% by weight or more, 8% by weight or more, 8.5% by weight or more, 9% by weight or more, 9.5% by weight or more, 10% by weight or more May contain, 0.01% by weight or less, 0.05% by weight or less, 0.1% by weight or less, 0.15% by weight or less, 0.18% by weight or less, 0.19% by weight or less, 0.2% by weight or less, 0.22% by weight or less, 0.23% by weight or less, 0.3% by weight or less, 0.4% by weight or less, 0.5% by weight or less, 1% by weight or less, 1.5% by weight or less, 2% by weight or less, 2.5% by weight or less, 3% by weight or less, 3.5% by weight or less, 4% by weight or less The amount may be, but is not limited to, 4.5% by weight or less, 5% by weight or less, 5.5% by weight or less, 6% by weight or less, 6.5% by weight or less, 7% by weight or less, 7.5% by weight or less, 8% by weight or less, 8.5% by weight or less, 9% by weight or less, 9.5% by weight or less, 10% by weight or less, or any combination thereof (e.g., 0.15-0.25% by weight, or 1-8% by weight).

[0035] In one embodiment, the hyaluronic acid hydrogel containing the hyaluronic acid or its salt may be, but is not limited to, hyaluronic acid or hyaluronate chemically crosslinked with a crosslinking agent.For example, the hyaluronic acid hydrogel containing hyaluronic acid may be, for example, hyaluronic acid chemically crosslinked with a crosslinking agent.For example, the hyaluronic acid hydrogel containing hyaluronate may be, for example, hyaluronic acid chemically crosslinked with a crosslinking agent, or hyaluronate chemically crosslinked with a crosslinking agent.

[0036] In one embodiment, the crosslinking agent is not limited to a specific type as long as it can crosslink hyaluronic acid and / or hyaluronate.

[0037] In one implementation, the crosslinking agent may be at least one selected from the group consisting of, but not limited to, a sulfone-based crosslinking agent, an epoxide-based crosslinking agent, and a phosphoric acid-based crosslinking agent.

[0038] In one implementation, the cross-linking agent is polyethylene glycol diglycidyl ether, sodium trimetaphosphate, epichlorohydrin, epibromohydrin, 1,4-butandiol diglycidyl ether, ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, The polyglycidyl ether may be at least one selected from the group consisting of, but is not limited to, polyglycerol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol polyglycidyl ether, trimethlypropane polyglycidyl ether, 1,2-(bis(2,3-epoxypropoxy)ethylene), pentaerythritol polyglycidyl ether, and sorbitol polyglycidyl ether.

[0039] In one embodiment, the ceramide may be a natural ceramide. In one embodiment, the ceramide may be a ceramide precursor.

[0040] In one embodiment, the ceramide may be at least one selected from the group consisting of Ceramide NP, Ceramide NS, Ceramide AS, Ceramide EOS, Ceramide NDS, Ceramide ADS, Ceramide EODS, Ceramide AP, Ceramide EOP, Ceramide NH, Ceramide AH, Ceramide EOH, and hydroxypalmitoyl sphinganine, but is not limited thereto.

[0041] In one implementation example, the pseudoceramide may be a synthetic substance that has similar functions to ceramide (eg, skin protective action, moisturizing ability, etc.).

[0042] In one embodiment, the pseudoceramide may be a substance having a function similar to that of ceramide, and the specific type is not limited. In one embodiment, the pseudoceramide may be a commercially available pseudoceramide, and the specific type is not limited.

[0043] In one embodiment, the pseudoceramide is Hydroxypropyl Bispalmitamide MEA, Hydroxypropyl Bisstearamide MEA, Hydroxypropyl Bislauramide MEA, Hydroxypropyl Bisisostearamide MEA, Bis-Hydroxyethyl Tocopherylsuccinoylamido Hydroxypropane, Cetyl-PG Hydroxyethyl Palmitamide, Myristoyl / Palmitoyl Oxostearamide / Arachamide MEA The anti-inflammatory agent may be at least one selected from the group consisting of, but not limited to, bis-palmitoyl tromethamine, bis-methyl-2-methyl-2-propanol, bis ...

[0044] In one embodiment, the pseudoceramide may be at least one selected from the group consisting of compounds represented by the following general formulas (1) to (6), but is not limited thereto.

[0045] [ka]

[0046] (wherein R is a saturated or unsaturated aliphatic chain of C9 to C21),

[0047] [ka]

[0048] (wherein n is 1 or 2, and R and R' are each independently a saturated or unsaturated aliphatic chain of C9 to C21),

[0049] [ka]

[0050] (In the formula, m and n are the same or different and are integers of 1 to 3, k and l are the same or different and are 1 or 2; j is 0 or 1, R and R' are the same or different and are C1 to C31 linear or branched, saturated or unsaturated alkyl groups that may or may not contain a hydroxy group; A 1 , A 2 , and A 3 are the same or different and are either hydrogen or a substituent of the following structure, provided that A 1 , A 2 , and A 3 The cases where both are hydrogen are excluded:

[0051] [ka]

[0052] [In the formula, M, M 1 and M 2 is selected from the group consisting of alkali metals, lysine, arginine, histidine, triethanolamine, ammonia, polyquaternium-4, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, lauryl dimethyl benzyl ammonium chloride, and stearyl dimethyl benzyl ammonium chloride, and L is an alkaline earth metal;

[0053] [ka]

[0054] (In the formula, R and R' are the same or different and are C10 to C32 linear or branched, saturated or unsaturated alkyl groups that may or may not contain a hydroxy group; R 3 and R 4 are the same or different and are hydrogen or a C1-C4 alkyl or hydroxyalkyl group, R 5 is -A or -CH2CH2OA, where A is any of the substituents of the following structures:

[0055] [ka]

[0056] [In the formula, M, M 1 and M 2 is selected from the group consisting of alkali metals, lysine, arginine, histidine, triethanolamine, ammonia, polyquaternium-4, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, lauryl dimethyl benzyl ammonium chloride, and stearyl dimethyl benzyl ammonium chloride, and L is an alkaline earth metal.

[0057] [ka]

[0058] (In the formula, m and n are the same or different and are integers of 1 to 4, R and R' are the same or different and are C1 to C31 linear or branched, saturated or unsaturated alkyl groups that may or may not contain a hydroxy group; A1 and A2 are the same or different and are either hydrogen or a substituent of the following structure:

[0059] [ka]

[0060] [In the formula, M, M 1 and M 2 is selected from the group consisting of alkali metals, lysine, arginine, histidine, triethanolamine, ammonia, polyquaternium-4, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-16, lauryl dimethyl benzyl ammonium chloride, and stearyl dimethyl benzyl ammonium chloride, and L is an alkaline earth metal;

[0061] [ka]

[0062] (In the formula, m and n are the same or different and are integers of 1 to 3, k and l are the same or different and are 1 or 2; j is 0 or 1, A 1 , A 2 , and A 3 are the same or different and are either hydrogen or a substituent of the structure:

[0063] [ka]

[0064] [In the formula, M, M 1 , and M 2 is an alkali metal or nitrogen-containing organic base, and L is an alkaline earth metal; R is a substituent having the structure:

[0065] [ka]

[0066] [wherein B is a methyl group at the 5-, 7-, or 8-position of tocopherol, m is an integer of 1 to 3, and D is -CH2(CH3)CH- or -CH(CH3)=C-].

[0067] Ceramides and / or pseudoceramides contained in hyaluronic acid hydrogels can exhibit the effects of strengthening the skin barrier and / or improving moisturizing power.

[0068] In one embodiment, the molecular weight of hyaluronic acid or hyaluronic acid salt may be, but is not limited to, 10,000 to 5,000,000 Da. For example, the molecular weight of hyaluronic acid or hyaluronic acid salt may be 10,000 Da or more, 20,000 Da or more, 30,000 Da or more, 40,000 Da or more, 50,000 Da or more, 60,000 Da or more, 70,000 Da or more, 80,000 Da or more, 90,000 Da or more, 100,000 Da or more, 200,000 Da or more, 300,000 Da or more, 400,000 Da or more, 500,000 Da or more, 600,000 Da or more, 70 It may be 0,000 Da or more, 800,000 Da or more, 900,000 Da or more, 1,000,000 Da or more, 1,500,000 Da or more, 2,000,000 Da or more, 2,500,000 Da or more, 3,000,000 Da or more, 3,500,000 Da or more, 4,000,000 Da or more, 4,500,000 Da or more, 5,000,000 Da or more, and may be 10,000 Da or less, 20,000 Da or less, 30,000 Da or less Lower, 40,000Da or less, 50,000Da or less, 60,000Da or less, 70,000Da or less, 80,000Da or less, 90,000Da or less, 100,000Da or less, 200,000Da or less, 300,000 Less than Da, less than 400,000Da, less than 500,000Da, less than 600,000Da, less than 700,000Da, less than 800,000Da, less than 900,000Da, less than 1,000,000Da, 1,500,000 The molecular weight may be, but is not limited to, 2,000,000 Da or less, 2,500,000 Da or less, 3,000,000 Da or less, 3,500,000 Da or less, 4,000,000 Da or less, 4,500,000 Da or less, 5,000,000 Da or less, or any combination thereof (e.g., 100,000 to 3,000,000 Da, or 900,000 to 1,100,000 Da).

[0069] In one implementation, the hyaluronic acid may be, but is not limited to, hyaluronic acid.

[0070] In one implementation, the hyaluronate may be, but is not limited to, sodium hyaluronate.

[0071] In one implementation, the hyaluronic acid hydrogel containing hyaluronic acid or its salt may be, but is not limited to, sodium hyaluronate crosspolymer, which may be a hydrogel crosslinked with hyaluronic acid or a hyaluronate salt.

[0072] In one embodiment, the average diameter of the emulsified particles may be, but is not limited to, 0.1 to 100 μm. For example, the average diameter of the emulsified particles may be 0.1 μm or more, 0.2 μm or more, 0.23 μm or more, 0.3 μm or more, 0.4 μm or more, 0.5 μm or more, 0.6 μm or more, 0.7 μm or more, 0.8 μm or more, 0.9 μm or more, 1 μm or more, 2 μm or more, 3 μm or more, 4 μm or more, 5 μm or more, 5.5 μm or more, 6 μm or more, 7 μm or more, 8 μm or more, 9 μm or more, 10 μm or more, 20 μm or more, 30 μm or more, 40 μm or more, 50 μm or more, 60 μm or more, 70 μm or more, 80 μm or more, 90 μm or more, 100 μm or more, or 0.1 μm or less, 0.2 μm or less, 0.23 μm or less, 0.5 μm or more, 0.6 μm or more, 0.7 μm or more, 0.8 μm or more, 0.9 μm or more, 1 μm or more, 2 μm or more, 3 μm or more, 4 μm or more, 5 μm or more, 5.5 μm or more, 6 μm or more, 7 μm or more, 8 μm or more, 9 μm or more, 10 μm or more, 20 μm or more, 30 μm or more, 40 μm or more, 50 μm or more, 60 μm or more, 70 μm or more, 80 μm or more, 90 μm or more, 100 μm or more, The thickness may be, but is not limited to, 0.3 μm or less, 0.4 μm or less, 0.5 μm or less, 0.6 μm or less, 0.7 μm or less, 0.8 μm or less, 0.9 μm or less, 1 μm or less, 2 μm or less, 3 μm or less, 4 μm or less, 5 μm or less, 5.5 μm or less, 6 μm or less, 7 μm or less, 8 μm or less, 9 μm or less, 10 μm or less, 20 μm or less, 30 μm or less, 40 μm or less, 50 μm or less, 60 μm or less, 70 μm or less, 80 μm or less, 90 μm or less, 100 μm or less, or a range combining these (for example, 0.2 to 0.6 μm, or 0.9 to 5.5 μm).

[0073] In one embodiment, the ceramide-conjugated hyaluronic acid hydrogel according to one aspect of the present disclosure may be a pulverized ceramide-conjugated hyaluronic acid hydrogel, or may be a pulverized ceramide-conjugated hyaluronic acid hydrogel in the form of particles.

[0074] In one embodiment, the ceramide-bonded hyaluronic acid hydrogel according to one embodiment of the present disclosure may be in the form of particles. In one embodiment, the diameter of the ceramide-bonded hyaluronic acid hydrogel according to one embodiment of the present disclosure may be, but is not limited to, 10 to 100 μm. For example, the diameter of the ceramide-bonded hyaluronic acid hydrogel according to one embodiment of the present disclosure may be 10 μm or more, 15 μm or more, 20 μm or more, 25 μm or more, 30 μm or more, 35 μm or more, 40 μm or more, 45 μm or more, 50 μm or more, 55 μm or more, 60 μm or more, 65 μm or more, 70 μm or more, 75 μm or more, 80 μm or more, 85 μm or more, 90 μm or more, 95 μm or more, or 100 μm or more, and may be 10 μm or less. The diameter may be, but is not limited to, 15 μm or less, 20 μm or less, 25 μm or less, 30 μm or less, 35 μm or less, 40 μm or less, 45 μm or less, 50 μm or less, 55 μm or less, 60 μm or less, 65 μm or less, 70 μm or less, 75 μm or less, 80 μm or less, 85 μm or less, 90 μm or less, 95 μm or less, or 100 μm or less, or a combination thereof (e.g., 40-60 μm). In one embodiment, the ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure may have a diameter greater than the above range depending on the grinding process (e.g., but is not limited to, the diameter of the ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure may be 0.01 cm or more, 0.1 cm or more, 1 cm or more, or 5 cm or more).

[0075] When the ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure includes a plurality of ceramide-conjugated hyaluronic acid hydrogel particles, the diameter may be an average diameter.

[0076] In one embodiment, the ceramide-bound hyaluronic acid hydrogel may further contain other ingredients that may be normally included in the composition (e.g., oil, cholesterol, polyglyceryl, etc.) as needed.

[0077] In one embodiment, the Tan δ of the ceramide-bound hyaluronic acid hydrogel may be, but is not limited to, 0.01 to 2. For example, the Tan δ of the ceramide-bound hyaluronic acid hydrogel may be 0.01 or more, 0.02 or more, 0.03 or more, 0.04 or more, 0.05 or more, 0.06 or more, 0.07 or more, 0.08 or more, 0.09 or more, 0.1 or more, 0.2 or more, 0.3 or more, 0.4 or more, 0.5 or more, 0.6 or more, 0.7 or more, 0.8 or more, 0.9 or more, 1 or more, 1.05 or more, 1.08 or more, 1.09 or more, 1.1 or more, 1.2 or more, 1.3 or more, 1.4 or more, 1.5 or more, 1.6 or more, 1.7 or more, 1.8 or more, 1.9 or more, or 2.0 or more, and may be 0.01 or less, 0.02 or less, or The range may be, but is not limited to, 0.03 or less, 0.04 or less, 0.05 or less, 0.06 or less, 0.07 or less, 0.08 or less, 0.09 or less, 0.1 or less, 0.2 or less, 0.3 or less, 0.4 or less, 0.5 or less, 0.6 or less, 0.7 or less, 0.8 or less, 0.9 or less, 1 or less, 1.05 or less, 1.08 or less, 1.09 or less, 1.1 or less, 1.2 or less, 1.3 or less, 1.4 or less, 1.5 or less, 1.6 or less, 1.7 or less, 1.8 or less, 1.9 or less, 2.0 or less, or a range combining these (for example, 0.08 to 1.09).

[0078] The Tan δ can be calculated by the following formula (1).

[0079]

number

[0080] In one embodiment, the elasticity of the ceramide-bound hyaluronic acid hydrogel at 25°C may be, but is not limited to, 50 to 1500 Pa. In the present disclosure, elasticity may be expressed as a storage modulus. For example, the elasticity of the ceramide-bound hyaluronic acid hydrogel at 25°C may be 50 Pa or more, 60 Pa or more, 70 Pa or more, 80 Pa or more, 90 Pa or more, 100 Pa or more, 110 Pa or more, 112 Pa or more, 120 Pa or more, 130 Pa or more, 140 Pa or more, 150 Pa or more, 160 Pa or more, 170 Pa or more, 180 Pa or more, 190 Pa or more, 200 Pa or more, 210 Pa or more, 220 Pa or more, 230 Pa or more, 240 Pa or more, 250 Pa or more, 260 Pa or more, 270 Pa or more. a or more, 280 Pa or more, 290 Pa or more, 300 Pa or more, 350 Pa or more, 400 Pa or more, 450 Pa or more, 500 Pa or more, 550 Pa or more, 600 Pa or more, 650 Pa or more, 700 Pa or more, 750 Pa or more, 760 Pa or more, 800 Pa or more, 850 Pa or more, 900 Pa or more, 950 Pa or more, 990 Pa or more, 1000 Pa or more, 1100 Pa or more, 1200 Pa or more, 1300 Pa or more, 1400 Pa or more, 1500 Pa or more, 50 Pa or less, 60 Pa a or less, 70Pa or less, 80Pa or less, 90Pa or less, 100Pa or less, 110Pa or less, 112Pa or less, 120Pa or less, 130Pa or less, 140Pa or less, 150Pa or less, 160Pa or less, 170Pa or less, 180Pa or less, 190P a or less, 200Pa or less, 210Pa or less, 220Pa or less, 230Pa or less, 240Pa or less, 250Pa or less, 260Pa or less, 270Pa or less, 280Pa or less, 290Pa or less, 300Pa or less, 350Pa or less, 400Pa or less, 45 The pressure may be 0 Pa or less, 500 Pa or less, 550 Pa or less, 600 Pa or less, 650 Pa or less, 700 Pa or less, 750 Pa or less, 760 Pa or less, 800 Pa or less, 850 Pa or less, 900 Pa or less, 950 Pa or less, 990 Pa or less, 1000 Pa or less, 1100 Pa or less, 1200 Pa or less, 1300 Pa or less, 1400 Pa or less, 1500 Pa or less, or a range combining these (for example, 100 to 760 Pa), but is not limited to these.

[0081] In one embodiment, the viscosity of the ceramide-bound hyaluronic acid hydrogel at 25°C may be, but is not limited to, 10 to 500 Pa. In the present disclosure, viscosity may be expressed as loss modulus. For example, the viscosity of the ceramide-bound hyaluronic acid hydrogel at 25°C may be 10 Pa or more, 20 Pa or more, 30 Pa or more, 40 Pa or more, 50 Pa or more, 60 Pa or more, 70 Pa or more, 80 Pa or more, 84 Pa or more, 90 Pa or more, 100 Pa or more, 110 Pa or more, 120 Pa or more, 121 Pa or more, 130 Pa or more, 140 Pa or more, 150 Pa or more, 160 Pa or more, 170 Pa or more, 180 Pa or more, 190 Pa or more, 200 Pa or more, 210 Pa or more, 220 Pa or more, 230 Pa or more, 240 Pa or more, 250 Pa or more, 260 Pa or more, 270 Pa or more, 274 Pa or more, 280 Pa or more, 300 Pa or more, 350 Pa or more, 400 Pa or more, 450 Pa or more, 500 Pa or more, or 10 Pa or less. , 20 Pa or less, 30 Pa or less, 40 Pa or less, 50 Pa or less, 60 Pa or less, 70 Pa or less, 80 Pa or less, 84 Pa or less, 90 Pa or less, 100 Pa or less, 110 Pa or less, 120 Pa or less, 121 Pa or less, 130 Pa or less, 140 Pa or less, 150 Pa or less, 160 Pa or less, 170 Pa or less, 180 Pa or less, 190 Pa or less, 200 Pa or less, 210 Pa or less, 220 Pa or less, 230 Pa or less, 240 Pa or less, 250 Pa or less, 260 Pa or less, 270 Pa or less, 274 Pa or less, 280 Pa or less, 300 Pa or less, 350 Pa or less, 400 Pa or less, 450 Pa or less, 500 Pa or less, or a range combining these (for example, 84 to 280 Pa), but is not limited to these.

[0082] In one embodiment, the swelling degree of the ceramide-bound hyaluronic acid hydrogel may be, but is not limited to, 10 to 300. For example, the swelling degree of the ceramide-bound hyaluronic acid hydrogel may be 10 or more, 20 or more, 30 or more, 40 or more, 50 or more, 60 or more, 70 or more, 80 or more, 90 or more, 100 or more, 110 or more, 120 or more, 130 or more, 140 or more, 150 or more, 160 or more, 170 or more, 180 or more, 190 or more, 200 or more, 210 or more, 220 or more, 230 or more, 240 or more, 250 or more, 260 or more, 270 or more, 280 or more, 290 or more, or 300 or more, or 10 or less, 20 or less, 300 or less, or 300 or less. The range may be 0 or less, 40 or less, 50 or less, 60 or less, 70 or less, 80 or less, 90 or less, 100 or less, 110 or less, 120 or less, 130 or less, 140 or less, 150 or less, 160 or less, 170 or less, 180 or less, 190 or less, 200 or less, 210 or less, 220 or less, 230 or less, 240 or less, 250 or less, 260 or less, 270 or less, 280 or less, 290 or less, 300 or less, or a range combining these (for example, 80 to 120), but is not limited to these.

[0083] In one implementation, the degree of swelling can be measured by the weight of the hyaluronic acid hydrogel before drying relative to the weight of the hyaluronic acid hydrogel after drying.

[0084] In one implementation, the swelling degree can be measured by the following swelling degree measurement method: [Method for measuring swelling degree] Swelling index = weight of ceramide-bound hyaluronic acid hydrogel (i.e., weight of ceramide-bound hyaluronic acid hydrogel before drying) / weight of ceramide-bound hyaluronic acid hydrogel measured after drying at 60°C for 12 hours.

[0085] The ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure may exhibit skin barrier strengthening and / or moisturizing improvement effects.

[0086] Compositions Comprising Ceramide-Conjugated Hyaluronic Acid Hydrogels In one aspect of the present disclosure, a composition containing the aforementioned ceramide-conjugated hyaluronic acid hydrogel is provided. Since the ceramide-conjugated hyaluronic acid hydrogel has already been described, detailed description thereof will be omitted.

[0087] The composition according to one embodiment of the present disclosure contains the above-mentioned ceramide-bound hyaluronic acid hydrogel, and thus can stably contain ceramide (or pseudo-ceramide) in the composition without undergoing an emulsification process. Conventionally, in order to stably contain both ceramide and hyaluronic acid in a composition, an emulsion preparation has been produced through an emulsification process.

[0088] The composition according to one embodiment of the present disclosure may be prepared by simply mixing the ceramide-conjugated hyaluronic acid hydrogel described above with water and / or any other ingredients that may be included in the composition.

[0089] In one implementation, the composition may be a solubilized formulation.

[0090] The term "solubilization" in the present disclosure may refer to a state in which a water-insoluble or partially soluble substance is dissolved in a clear solution. A solubilized formulation may be similar to an oil-in-water (O / W) formulation, but may have a relatively high content of purified water (or water). Due to their relatively light and non-sticky properties, solubilized formulations are primarily used in products such as lotions, emollients, sprays, mists, and perfumes.

[0091] In one embodiment, the composition according to one aspect of the present disclosure may be transparent, which can improve consumer satisfaction in terms of appearance. On the other hand, an emulsion composition containing both ceramide and hyaluronic acid prepared by a conventional emulsification process is a white suspension formulation.

[0092] In one embodiment, the composition may be a skin moisturizing composition, hi one embodiment, the composition may be a skin barrier strengthening composition.

[0093] In one embodiment, the composition may be a cosmetic composition, a non-therapeutic composition, a pharmaceutical composition, an external application composition, a food composition, an oral composition, or a non-therapeutic oral composition. For example, the composition may be a cosmetic composition, a pharmaceutical composition (e.g., a transdermal pharmaceutical composition), or an external application composition (e.g., an external application composition for skin). In one embodiment, the composition may be applied to the skin or to the hair.

[0094] In one embodiment, the composition may further contain other ingredients typically incorporated into compositions, as needed. For example, the composition may further contain, but is not limited to, moisturizers, emollients, organic and inorganic pigments, organic powders, UV absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjusters, alcohol, colorants, fragrances, blood circulation enhancers, cooling agents, and / or purified water. The amounts of the ingredients may be varied without limitation as long as the objectives and effects of the present disclosure are not impaired.

[0095] In one implementation, the composition may be formulated in the form of, but not limited to, a lotion, toner, spray, mist, perfume, lotion, cream, pack, gel, powder, ointment, or stick concealer.

[0096] The composition according to one embodiment of the present disclosure can be applied to various formulations. In particular, the composition according to one embodiment of the present disclosure can be applied as a solubilized formulation, and in this case, it may be provided in the form of, but is not limited to, a lotion, toner, spray, mist, skin, or perfume.

[0097] Methods for promoting skin moisture or strengthening the skin barrier In one aspect of the present disclosure, there is provided a method for improving skin, comprising applying the aforementioned ceramide-conjugated hyaluronic acid hydrogel to a subject. In one aspect of the present disclosure, there is provided a method for improving skin, comprising applying the aforementioned ceramide-conjugated hyaluronic acid hydrogel to a subject.

[0098] In one aspect of the present disclosure, there is provided a method for improving skin, comprising applying a composition comprising the ceramide-conjugated hyaluronic acid hydrogel described above. In one aspect of the present disclosure, there is provided a method for improving skin, comprising applying a composition comprising the ceramide-conjugated hyaluronic acid hydrogel described above to a subject.

[0099] The ceramide-bound hyaluronic acid hydrogel and the composition containing the ceramide-bound hyaluronic acid hydrogel have already been described, and therefore a detailed description thereof will be omitted.

[0100] In one embodiment, the application may be, but is not limited to, oral, transdermal, subcutaneous, intravenous, intraperitoneal, intramuscular, topical, or cutaneous.

[0101] In one embodiment, the subject may be an animal, including, but not limited to, a mammal (e.g., a human). In one embodiment, the subject may be an individual in need of skin moisturizing or skin barrier strengthening. In one embodiment, the skin improvement may be, but is not limited to, promoting skin moisturizing or strengthening the skin barrier.

[0102] In one implementation, the skin improvement method may be, but is not limited to, a method for promoting skin moisture or strengthening the skin barrier.

[0103] Method for producing ceramide-bound hyaluronic acid hydrogel In one aspect of the present disclosure, (a) mixing at least one of ceramide or pseudoceramide, an emulsifier, and water to prepare a ceramide emulsion composition; (b) mixing the produced ceramide emulsion composition with at least one of hyaluronic acid or a hyaluronate salt and a crosslinker to obtain a hyaluronic acid hydrogel with emulsified particles containing at least one of ceramide or pseudoceramide bound thereto.

[0104] The method for producing a ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure may be a method for producing the above-mentioned ceramide-conjugated hyaluronic acid hydrogel.

[0105] Ceramide, pseudoceramide, hyaluronic acid, hyaluronate, crosslinker, emulsified particles containing at least one of ceramide or pseudoceramide, ceramide-bound hyaluronic acid hydrogel, and hydrogel have already been described, so detailed description thereof will be omitted.

[0106] In one implementation, the emulsifier may be at least one selected from the group consisting of, but not limited to, polyglyceryl surfactants or anionic surfactants.

[0107] In one implementation, the emulsifier may be at least one selected from the group consisting of, but not limited to, Polyglyceryl-3 Methylglucose Distearate, Polyglyceryl-2 Stearate, Polyglyceryl-10 Stearate, Cetyl Phosphate, Sodium Stearoyl Glutamate, Sodium Stearoyl Lactylate, Glyceryl Stearate Citrate, and Seryl Phosphate.

[0108] In one implementation, the water may be, but is not limited to, purified water and / or distilled water.

[0109] In one embodiment, the ceramide emulsion composition may further contain other components that may normally be contained in a composition (for example, cholesterol, polyglyceryl, etc.), if necessary.

[0110] In one implementation, the ceramide emulsion composition may include ceramide emulsion particles.

[0111] In one embodiment, the average diameter of the emulsified particles may be, but is not limited to, 0.1 to 100 μm. For example, the average diameter of the emulsified particles may be 0.1 μm or more, 0.2 μm or more, 0.23 μm or more, 0.3 μm or more, 0.4 μm or more, 0.5 μm or more, 0.6 μm or more, 0.7 μm or more, 0.8 μm or more, 0.9 μm or more, 1 μm or more, 2 μm or more, 3 μm or more, 4 μm or more, 5 μm or more, 5.5 μm or more, 6 μm or more, 7 μm or more, 8 μm or more, 9 μm or more, 10 μm or more, 20 μm or more, 30 μm or more, 40 μm or more, 50 μm or more, 60 μm or more, 70 μm or more, 80 μm or more, 90 μm or more, or 100 μm or more, or 0.1 μm or less, 0.2 μm or less, 0.2 The thickness may be 3 μm or less, 0.3 μm or less, 0.4 μm or less, 0.5 μm or less, 0.6 μm or less, 0.7 μm or less, 0.8 μm or less, 0.9 μm or less, 1 μm or less, 2 μm or less, 3 μm or less, 4 μm or less, 5 μm or less, 5.5 μm or less, 6 μm or less, 7 μm or less, 8 μm or less, 9 μm or less, 10 μm or less, 20 μm or less, 30 μm or less, 40 μm or less, 50 μm or less, 60 μm or less, 70 μm or less, 80 μm or less, 90 μm or less, 100 μm or less, or a range combining these (for example, 0.2 to 0.6 μm), but is not limited to these.

[0112] In one implementation, the ceramide emulsion composition may be an oil-in-water (O / W) emulsion composition.

[0113] In one embodiment, the step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide or pseudoceramide bound thereto includes: The ceramide emulsion composition prepared in (a) may be mixed with at least one of hyaluronic acid or a hyaluronate and a crosslinker to produce a hyaluronic acid hydrogel containing at least one ceramide or pseudoceramide-bound emulsion particle. The reaction may be carried out at, but is not limited to, 20-60°C, 25-60°C, 30-60°C, 30-50°C, 30-40°C, or 35-40°C.

[0114] In one embodiment, the step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide or pseudoceramide bound thereto includes: The ceramide emulsion composition prepared in (a) may be dispersed in an alkaline solution, and then mixed with hyaluronic acid or a hyaluronate and a crosslinker to react with the resulting hyaluronic acid hydrogel, which may be carried out at temperatures ranging from 20 to 60°C, 25 to 60°C, 30 to 60°C, 30 to 50°C, 30 to 40°C, or 35 to 40°C, but is not limited thereto.

[0115] In one implementation, the alkaline solution may include, but is not limited to, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, ammonia, sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate, and other alkalis.

[0116] In one embodiment, the step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide or pseudoceramide bound thereto includes: The ceramide emulsion composition prepared in (a) above may be mixed with hyaluronic acid or a hyaluronate salt and a crosslinker to obtain a gel mixture, and the resulting gel mixture may be swelled and then pulverized to obtain a hyaluronic acid hydrogel to which emulsion particles containing at least one of ceramide or pseudoceramide are bound.

[0117] In the step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide and pseudoceramide bound thereto, the hyaluronic acid or its salt may be contained in an amount of more than 10% by weight to less than 30% by weight of the total weight of the gel mixture, but is not limited thereto. For example, the hyaluronic acid or its salt may be contained in an amount of more than 10% by weight, 11% by weight or more, 12% by weight or more, 13% by weight or more, 14% by weight or more, 15% by weight or more, 16% by weight or more, 17% by weight or more, 18% by weight or more, 19% by weight or more, 20% by weight or more, 21% by weight or more, 22% by weight or more, 23% by weight or more, 24% by weight or more, 25% by weight or more, 26% by weight or more, 27% by weight or more, 28% by weight or more, 29% by weight or more, or 11% by weight or less, 12% by weight or less, 13% by weight or less, or 14% by weight or more. %, 14% or less, 15% or less, 16% or less, 17% or less, 18% or less, 19% or less, 20% or less, 21% or less, 22% or less, 23% or less, 24% or less, 25% or less, 26% or less, 27% or less, 28% or less, 29% or less, less than 30% by weight, or a combination of these (for example, 15% or more and less than 30% by weight, or 15 to 25% by weight), but is not limited to these.

[0118] In one embodiment, step (b) may be performed at a temperature of, but not limited to, 20 to 60°C, 25 to 60°C, 30 to 60°C, 30 to 50°C, 30 to 40°C, or 35 to 40°C.

[0119] In one embodiment, the hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide or pseudoceramide bound thereto obtained in (b) above may be in the form of particles.

[0120] In one embodiment, the diameter of the hyaluronic acid hydrogel to which emulsified particles containing at least one of ceramide or pseudoceramide obtained in (b) are bonded may be, but is not limited to, 10 to 100 μm. For example, the diameter of the hyaluronic acid hydrogel to which emulsified particles containing at least one of ceramide or pseudoceramide obtained in (b) are bonded may be 10 μm or more, 15 μm or more, 20 μm or more, 25 μm or more, 30 μm or more, 35 μm or more, 40 μm or more, 45 μm or more, 50 μm or more, 55 μm or more, 60 μm or more, 65 μm or more, 70 μm or more, 75 μm or more, 80 μm or more, 85 μm or more, 90 μm or more, 95 μm or more, or 100 μm or more. The thickness may be 10 μm or less, 15 μm or less, 20 μm or less, 25 μm or less, 30 μm or less, 35 μm or less, 40 μm or less, 45 μm or less, 50 μm or less, 55 μm or less, 60 μm or less, 65 μm or less, 70 μm or less, 75 μm or less, 80 μm or less, 85 μm or less, 90 μm or less, 95 μm or less, 100 μm or less, or a range combining these (for example, 40 to 60 μm), but is not limited to these. In one embodiment, the diameter of the hyaluronic acid hydrogel having emulsified particles containing at least one ceramide or pseudoceramide bonded thereto obtained in (b) may be larger than the above range depending on the grinding process (for example, the diameter of the hyaluronic acid hydrogel having emulsified particles containing at least one ceramide or pseudoceramide bonded thereto obtained in (b) may be, but is not limited to, 0.01 cm or more, 0.1 cm or more, 1 cm or more, or 5 cm or more).

[0121] When the hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide or pseudoceramide bound thereto obtained in (b) contains a plurality of hydrogel particles, the diameter may be the average diameter of the plurality of hydrogel particles.

[0122] In one implementation, the grinding may be performed by an extruder equipped with a sieve.

[0123] Method for producing a composition containing ceramide-bound hyaluronic acid hydrogel In one aspect of the present disclosure, there is provided a method for producing a composition, comprising the step of mixing i) the aforementioned ceramide-conjugated hyaluronic acid hydrogel, or ii) a ceramide-conjugated hyaluronic acid hydrogel produced by the aforementioned method for producing a ceramide-conjugated hyaluronic acid hydrogel, with purified water.

[0124] The ceramide-bound hyaluronic acid hydrogel, the method for producing the ceramide-bound hyaluronic acid hydrogel, and the composition containing the ceramide-bound hyaluronic acid hydrogel have already been described, so detailed description thereof will be omitted.

[0125] In one embodiment, the method for producing the composition may be, but is not limited to, a method for producing a solubilized composition.The method for producing a composition according to one aspect of the present disclosure uses hyaluronic acid bound to ceramide or pseudoceramide, thereby making it possible to produce a composition containing both ceramide and hyaluronic acid, which have different physical properties, without undergoing an emulsification process.

[0126] In one implementation, the method for preparing the composition may not require an emulsification step.

[0127] In one embodiment, the mixing step may be performed at room temperature, but is not limited thereto. On the other hand, the emulsification step that has been mainly used in the past to prepare a composition containing ceramide and hyaluronic acid is performed at a high temperature, which is different from the method for preparing a composition according to one embodiment of the present disclosure.

[0128] In one embodiment, the method for producing the composition may further include adding other components that may be typically included in the composition to the purified water. The other components that may be included in the composition have already been described, so a detailed description thereof will be omitted.

[0129] In one embodiment, the step of adding the other ingredients to the purified water may be performed simultaneously with the mixing step, or may be performed after or before the mixing step.

[0130] The present invention will be described in detail below with reference to examples, which are provided to aid in understanding the present invention and are not intended to limit the scope of the present invention.

[0131] [Embodiment] <Preparation of ceramide-bound hyaluronic acid hydrogel> [Example 1] Production of ceramide emulsion composition An emulsion composition (emulsion base) containing ceramide or pseudoceramide was prepared according to the composition shown in Table 1. Specifically, the pseudoceramide and / or ceramide NP, cholesterol, and emulsifier were added to glycerin or water, and then the mixture was heated to 80°C to dissolve, followed by homomixing at 6,000 rpm for 3 minutes to prepare the ceramide emulsion composition.

[0132] Preparation Examples 4 and 5 are glycerin-based emulsion bases (oil-in-polyol bases; O / P bases) prepared using glycerin instead of water. When dispersed in water, nanoemulsion particles are generated by D-phase emulsification. Preparation Examples 1 and 2 are ceramide emulsion bases prepared using glycerin-free water containing 28% by weight and 19% by weight of pseudoceramide, respectively. Preparation Example 3 is a ceramide emulsion base prepared using glycerin-free water with 10% by weight of ceramide NP.

[0133] [Table 1]

[0134] The emulsion particle size and polydispersity of the emulsion compositions of Preparation Examples 1 to 5 were measured. The emulsion particle size and polydispersity were measured using a Zeta-sizer (Zetasizer Nano ZS, Malvern). The emulsion particle sizes of Preparation Examples 1 to 3, which were produced using water, were in the range of 150 to 300 nm. When hyaluronic acid hydrogels were produced using the emulsion bases of Preparation Examples 4 and 5, no gels were produced, and there was a risk that glycerin would inhibit the reaction between hyaluronic acid and the crosslinker. Therefore, the emulsion bases of Preparation Examples 4 and 5 were excluded from subsequent experiments.

[0135] [Table 2]

[0136] [Example 2] Preparation of ceramide-conjugated hyaluronic acid hydrogels Ceramide-bound hyaluronic acid hydrogels were prepared according to the compositions shown in Table 3. In Table 3, PEGDE is polyethylene glycol diglycidyl ether, STMP is sodium trimetaphosphate, and hyaluronic acid is sodium hyaluronate (molecular weight Mw approximately 1 million Da).

[0137] Specifically, a ceramide emulsion composition having the composition shown in Preparation Example 2 in Table 1 was dispersed in 0.24 N KOH solution using a homogenizer. Hyaluronic acid and a crosslinker (PEGDE or STMP) were then added and mixed until uniform. The mixture was incubated in an incubator at 37°C for 24 hours. The resulting gel mixture was neutralized to a pH of approximately 7 by adding acetic acid. The neutralized gel was then placed in a laundry net and washed and allowed to swell in purified water for 24 hours. The slightly swollen gel was then crushed to a size of 50 μm using an extruder equipped with a 100 μm sieve to produce a hydrogel.

[0138] [Table 3]

[0139] In Comparative Example 1, in which hyaluronic acid was mixed at 10 wt % of the total weight, the hydrogel was not crosslinked, and in Comparative Example 2, in which hyaluronic acid was mixed at 30 wt % of the total weight, mixing was impossible due to the problem of high viscosity, so no hydrogel was produced.

[0140] <Experimental Example - Properties and Effects of Ceramide-Conjugated Hyaluronic Acid Hydrogel> 1. Evaluation of the physical properties of ceramide-conjugated hyaluronic acid hydrogels The viscoelasticity of the hydrogels of Examples 1 to 3 prepared in "2. Preparation of ceramide-conjugated hyaluronic acid hydrogels" was measured using a rheometer (KINEXUS Pro+, USA). Specifically, elasticity (storage modulus; G') and viscosity (loss modulus; G") were measured at 25°C using a 20 mm plate under the conditions of a frequency range of 0.1 to 10 Hz, 1 Pa shear stress, and a 1 mm gap. The values ​​of G', G", and Tanδ at 1 Hz are shown in Table 4. The Tanδ value was calculated using the following formula: Tanδ = G" / G'.

[0141] [Table 4]

[0142] As described in "2. Preparation of Ceramide-Conjugated Hyaluronic Acid Hydrogels," viscoelasticity measurements were not possible in Comparative Examples 1 and 2 because no hydrogels were produced. The hydrogel of Example 1, which used PEGDE as a crosslinker, had a storage modulus of 983 Pa, a loss modulus of 84.99 Pa, and a Tan δ value of 0.086, making it relatively hard. Meanwhile, the hydrogel of Example 2, which used STMP as a crosslinker, had a slightly lower storage modulus and a higher loss modulus, but a high viscosity with a Tan δ value of 1.078. In Example 3, where the STMP content was increased, both the storage modulus and loss modulus increased. Hyaluronic acid-ceramide hydrogels with various physical properties can be prepared by controlling the type and content of the crosslinker.

[0143] 2. Evaluation of swelling degree and ceramide content of ceramide-bound hyaluronic acid hydrogels The swelling degree and ceramide content of the hydrogels prepared in the examples in "2. Preparation of ceramide-bound hyaluronic acid hydrogels" were analyzed.

[0144] The swelling degree was evaluated by numerically calculating the water content of the hydrogel. Specifically, the prepared hydrogel was weighed, then completely dried in an oven at 60°C for 12 hours, and the weight was measured. The weight ratio after drying (weight before drying / weight after drying) was then calculated. As shown in Table 5 below, it was confirmed that the swelling degree differed depending on the crosslinking conditions. The theoretical swelling degree was calculated based on the fact that when the swelling degree is 100 times, the hyaluronic acid content is 1% and the ceramide content is 0.2%.

[0145] In addition, when manufacturing ceramide-bound hyaluronic acid hydrogel, we checked whether ceramide emulsion particles were removed during crosslinking and subsequent washing processes. Ceramide content analysis was performed by HPLC, where 1 g of hydrogel was diluted with 10 mL of methanol and filtered through a 0.45 μm filter, followed by HPLC analysis under the following conditions:

[0146] [HPLC analysis conditions] -Column: C18 column 5μm, 250mm x 4.6mm Mobile phase: Acetonitrile:Methanol = 7:3 -Temperature: 20℃ -Flow rate: 0.8mL / min -UV Detector: 210nm -Waters HPLC.

[0147] In Table 5, a comparison of the theoretical and measured values ​​of the ceramide content according to the swelling degree confirmed that the hydrogel according to one embodiment of the present disclosure contained up to about 0.25 wt % of ceramide relative to the total weight, which was within the measurement error range, confirming that there was no loss of ceramide during the manufacturing process.

[0148] [Table 5]

[0149] 3. Image analysis of ceramide-conjugated hyaluronic acid hydrogels The images of the hydrogels prepared in the example in "2. Preparation of ceramide-bound hyaluronic acid hydrogels" were analyzed.

[0150] Specifically, the hydrogel prepared in Example 3 in "2. Preparation of ceramide-bound hyaluronic acid hydrogel" was observed under a microscope (Nikon eclipse) at 100x magnification, and it was confirmed that the hydrogel contained emulsified particles ranging from approximately 1 to 5 μm in size (see Figure 2).

[0151] To more accurately identify ceramide, the hydrogel of Example 3 was further observed using a confocal microscope (Carl Zeiss LSM980 NLO). The hydrogel of Example 3 was diluted 1:100 with Nile Red O solution and then stained at room temperature for 1 hour. The stained hydrogel was placed on the measurement stage of the confocal microscope using a pipette and then observed at 400x magnification. As a result, the control hydrogel without ceramide appeared black, indicating that it was not stained with Nile Red O. On the other hand, the hydrogel of Example 3 appeared red overall (shown in gray in Figure 3). This confirmed that ceramide was stained and distributed throughout the gel. The control group in Figure 3 is a hyaluronic acid hydrogel without ceramide emulsified particles. The basic solution, hyaluronic acid, and crosslinker used in the hydrogel preparation were the same as those in Example 3.

[0152] 4. Evaluation of compositions containing ceramide-conjugated hyaluronic acid hydrogels A composition containing the hydrogel of the example prepared in "2. Preparation of ceramide-bound hyaluronic acid hydrogel" was prepared, and its physical properties and efficacy were evaluated.

[0153] (1) Preparation of a composition containing ceramide and hyaluronic acid A composition (ampule) containing ceramide and hyaluronic acid was prepared according to the formulation in Table 6 below.

[0154] Example 4 in Table 6 is a composition containing the hydrogel prepared in Example 3 in "2. Preparation of ceramide-bound hyaluronic acid hydrogel." Specifically, the composition of Example 4 was prepared by adding all of the components in Table 6 below at room temperature and then mixing at about 3,000 rpm for 3 minutes.

[0155] Comparative Example 3 in Table 6 is an emulsion composition emulsified with ceramide and pseudoceramide. In Comparative Example 3, the ceramide and pseudoceramide were emulsified in the same content as the hydrogel of Example 3 prepared in "2. Preparation of ceramide-bound hyaluronic acid hydrogel." Specifically, the ceramide, pseudoceramide, cholesterol, and emulsifier were heated to 80°C, and then water heated to 70°C was added and emulsified at approximately 6,000 rpm for 3 minutes. The resulting emulsion composition was cooled to approximately 50°C, and the remaining ingredients were then added to prepare the composition of Comparative Example 3.

[0156] [Table 6]

[0157] To produce a composition containing both ceramide and hyaluronic acid, a step of emulsifying ceramide at high temperature is required, as in the production method of Comparative Example 3 described above, and therefore it is difficult to produce a solubilized formulation composition without an emulsification step. On the other hand, the ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present disclosure can be formulated by dispersing it in water (or purified water) at room temperature, as in the production method of Example 4 described above, and therefore can also be produced as a solubilized formulation composition. The contents of hyaluronic acid and ceride contained in the composition can be adjusted by adjusting the contents of the gel.

[0158] (2) Evaluation of the appearance of the composition The composition of Example 4 (ampoules containing 10% by weight of ceramide-bound hyaluronic acid hydrogel) prepared in "4. (1) Preparation of a composition containing ceramide and hyaluronic acid" was relatively transparent. On the other hand, the composition of Comparative Example 3, which was an emulsion of the same content of hyaluronic acid and ceramide, was a white suspension preparation, which can be said to have the typical form of an emulsion preparation (Figure 4).

[0159] (3) Evaluation of the moisturizing power of the composition The moisturizing power of the compositions of the Examples and Comparative Examples prepared in the above "4. (1) Preparation of a composition containing ceramide and hyaluronic acid" was compared.

[0160] Skin moisture content was measured at the test site (2 x 2 cm area) using a skin moisture meter (GP Skin, G-Power) with a skin SCH (Stratum Corneum Hydration) sensor. Moisture measurement results are displayed up to 100%, with values ​​below 60% generally considered dry, below 80% considered normal, and above 80% considered sufficiently moisturized. First, to remove any remaining moisturizing ingredients from the skin, the subject's forearm was washed with a cleanser. After waiting 10 minutes, the skin moisture content of the test site was measured (control group). 20 μL of ampoules from Example 4 and Comparative Example 3 were applied to the test site and allowed to absorb, and changes in skin moisture content were measured after 10 minutes, 30 minutes, 1 hour, and 3 hours.

[0161] Measurements showed that the initial skin moisture content (before treatment with the Examples and Comparative Examples) was approximately 65%. After treatment with the composition of Example 4 containing ceramide-bound hyaluronic acid hydrogel, the skin moisture content was measured, reaching 100% after 10 minutes, 100% after 30 minutes, 91.5% after 1 hour, and 85.5% after 3 hours. Meanwhile, after treatment with the composition of Comparative Example 3 in which ceramide was emulsified with hyaluronic acid, the skin moisture content was measured, reaching 86.5% after 10 minutes, 79.5% after 30 minutes, 73% after 1 hour, and 70.5% after 3 hours (Figure 5). As a result, the composition of Example 4 containing ceramide-bound hyaluronic acid hydrogel showed superior moisturizing power to the composition of Comparative Example 3 in which the same amount of ceramide was emulsified with hyaluronic acid.

[0162] (4) Evaluation of the feel of the composition when used The sensations when used with the compositions of the Examples and Comparative Examples prepared in the above "4. (1) Preparation of a composition containing ceramide and hyaluronic acid" were compared by sensory evaluation.

[0163] The compositions of Example 4 and Comparative Example 3 were applied to the back of the hand of a specialist sensory panel, and the properties of adhesion, coolness, oiliness, and slimy feel were evaluated by scoring.

[0164] Specifically, in the skin care category, seven trained sensory panel members evaluated the products using a 20-point scale (0 points (not noticeable) to 19 points (very noticeable)) using a sensory evaluation method (SOP) set for ampoule / essence types.

[0165] As a result of the sensory evaluation, the composition of Example 4 containing the ceramide-bound hyaluronic acid hydrogel had a strong adhesive feeling and a cool feeling, but a relatively low oily feeling and slippery feeling. On the other hand, the composition of Comparative Example 3, in which the same amount of ceramide was emulsified in hyaluronic acid, had a relatively low adhesive feeling and a cool feeling, and in particular, the slippery feeling characteristic of hyaluronic acid was remarkable (Table 7). It is considered that the ceramide-bound hyaluronic acid hydrogel according to one embodiment of the present disclosure loses the slippery feeling characteristic of hyaluronic acid as the hyaluronic acid crosslinks and the molecular weight increases.

[0166] [Table 7]

[0167] In summary, the ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure can be stable because the ceramide is distributed throughout the hydrogel. Furthermore, the ceramide-conjugated hyaluronic acid hydrogel according to one embodiment of the present disclosure can be easily mixed with water (or purified water) at room temperature to prepare a composition (e.g., a solubilized preparation), and the prepared composition has excellent moisturizing power and usability.

[0168] On the other hand, in order to apply ceramide to composition together with hyaluronic acid without bonding with hydrogel, it is necessary to carry out emulsification process at high temperature, and there is a drawback that the process is not simple.The composition produced through this emulsification process is white in emulsion preparation, so its appearance is relatively irregular.In addition, although the composition produced through emulsification process contains the same amount of ceramide as the composition that comprises the hyaluronic acid hydrogel that is bonded with ceramide according to one embodiment of the present invention, it does not have good moisturizing power and feeling of use.

[0169] The present disclosure is further illustrated by the following implementations, which do not limit the scope of the claims.

[0170] Example 1: A hyaluronic acid hydrogel containing hyaluronic acid or its salt, and emulsifying particles bound to the hyaluronic acid hydrogel, A ceramide-bound hyaluronic acid hydrogel, wherein the emulsified particles contain at least one of ceramide and pseudoceramide.

[0171] Example 2. In Example 1, A ceramide-bonded hyaluronic acid hydrogel containing 0.1 to 10% by weight of the hyaluronic acid or a salt thereof relative to the total weight of the ceramide-bonded hyaluronic acid hydrogel.

[0172] Example 3: In any one of Examples 1 and 2, A ceramide-bound hyaluronic acid hydrogel containing 0.01 to 10% by weight of at least one of the ceramides or pseudoceramides relative to the total weight of the ceramide-bound hyaluronic acid hydrogel.

[0173] Example 4. In any one of Examples 1 to 3, The hyaluronic acid hydrogel containing hyaluronic acid or its salt is a ceramide-bound hyaluronic acid hydrogel in which hyaluronic acid or a hyaluronate is chemically crosslinked with a crosslinking agent.

[0174] Implementation Example 5. In Implementation Example 4, A ceramide-conjugated hyaluronic acid hydrogel, wherein the crosslinking agent is at least one selected from the group consisting of a sulfone-based crosslinking agent, an epoxide-based crosslinking agent, and a phosphate-based crosslinking agent.

[0175] Implementation 6. In any one of Implementations 4 and 5, The crosslinking agent may be polyethylene glycol diglycidyl ether, sodium trimetaphosphate, epichlorohydrin, epibromohydrin, 1,4-butandiol diglycidyl ether, ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polyglycerol a ceramide-conjugated hyaluronic acid hydrogel, the ceramide-conjugated hyaluronic acid hydrogel being at least one selected from the group consisting of 1,2-bis(2,3-epoxypropoxy)ethylene, 1,2-bis(2,3-epoxypropoxy)ethylene, pentaerythritol polyglycidyl ether, and sorbitol polyglycidyl ether;

[0176] Implementation Example 7. In any one of Implementation Examples 1 to 6, A ceramide-conjugated hyaluronic acid hydrogel, wherein the ceramide is at least one selected from the group consisting of Ceramide NP, Ceramide NS, Ceramide AS, Ceramide EOS, Ceramide NDS, Ceramide ADS, Ceramide EODS, Ceramide AP, Ceramide EOP, Ceramide NH, Ceramide AH, Ceramide EOH, and hydroxypalmitoyl sphinganine.

[0177] Implementation Example 8. In any one of Implementation Examples 1 to 7, The pseudoceramide may be hydroxypropyl bispalmitamide MEA, hydroxypropyl bisstearamide MEA, hydroxypropyl bislauramide MEA, hydroxypropyl bisisostearamide MEA, bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane, cetyl-PG hydroxyethyl palmitamide, myristoyl / palmitoyl oxostearamide / arachamide MEA, or any of the above-mentioned compounds. Ceramide-conjugated hyaluronic acid hydrogels, which are at least one selected from the group consisting of ceramide-conjugated hyaluronic acid hydrogels (Ceramide-conjugated hyaluronic acid hydrogels), ceramide-conjugated hyaluronic acid hydrogels, and cer ... (Ceramide-conjugated hyaluronic acid hydrogels), ceramide-conjugated hyaluronic acid hydrogels, and ceramide-conjugated hyaluronic acid hydrogels (Ceramide-conjugated hyaluronic acid

[0178] Implementation Example 9. In any one of Implementation Examples 1 to 8, The ceramide-bound hyaluronic acid hydrogel, wherein the emulsified particles have an average diameter of 0.1 to 100 μm.

[0179] Implementation Example 10. In any one of Implementation Examples 1 to 9, The ceramide-bound hyaluronic acid hydrogel has a Tan δ of 0.01 to 2; 2. The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein Tan δ is calculated by the following formula (1):

[0180]

number

[0181] Implementation Example 11. In any one of Implementation Examples 1 to 10, The swelling degree of the ceramide-bound hyaluronic acid hydrogel is 10 to 300, The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein the swelling degree is measured by the following swelling degree measurement method: [Method for measuring swelling degree] Swelling degree = weight of ceramide-bound hyaluronic acid hydrogel before drying / weight measured after drying the ceramide-bound hyaluronic acid hydrogel at 60°C for 12 hours. Realization Example 12. A composition comprising a ceramide-conjugated hyaluronic acid hydrogel according to any one of Realization Examples 1 to 11.

[0182] Realization Example 13: The composition of Realization Example 12, wherein the composition is a solubilized formulation or a transparent formulation.

[0183] Example 14. A method for producing a ceramide-conjugated hyaluronic acid hydrogel according to any one of Examples 1 to 11, comprising: (a) mixing at least one of ceramide or pseudoceramide, an emulsifier, and water to prepare a ceramide emulsion composition; (b) mixing the produced ceramide emulsion composition with at least one of hyaluronic acid or a hyaluronate salt and a crosslinking agent to obtain a hyaluronic acid hydrogel with emulsion particles containing at least one of ceramide or pseudoceramide bound thereto.

[0184] Example 15: In Example 14, the ceramide emulsion composition comprises ceramide emulsion particles, which is a method for producing a ceramide-bound hyaluronic acid hydrogel.

[0185] Implementation 16. In any one of implementations 14 and 15, The step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide and pseudoceramide bound thereto, The method for producing a ceramide-bound hyaluronic acid hydrogel comprises mixing the ceramide emulsion composition produced in (a) with hyaluronic acid or a hyaluronate salt and a crosslinking agent to obtain a gel mixture, swelling the resulting gel mixture, and then pulverizing it to obtain a hyaluronic acid hydrogel to which emulsion particles containing at least one of ceramide or pseudo-ceramide are bound.

[0186] Realization Example 17. A method for producing a composition, comprising: mixing the ceramide-conjugated hyaluronic acid hydrogel of any one of Realization Examples 1 to 11 with purified water.

[0187] Realization Example 18: In the method for producing a composition according to Realization Example 17, the mixing step is carried out at room temperature.

[0188] Implementation Example 19. A method for improving skin, comprising applying the composition of any one of Implementation Examples 12 and 13 to a subject.

[0189] Example 20: In Example 19, the skin improvement method is to promote skin moisturization or strengthen the skin barrier.

Claims

1. a hyaluronic acid hydrogel containing hyaluronic acid or a salt thereof; and emulsifying particles bound to the hyaluronic acid hydrogel, A ceramide-bound hyaluronic acid hydrogel, wherein the emulsified particles contain at least one of ceramide and pseudoceramide.

2. 2. The ceramide-bonded hyaluronic acid hydrogel according to claim 1, wherein the hyaluronic acid or its salt is contained in an amount of 0.1 to 10% by weight based on the total weight of the ceramide-bonded hyaluronic acid hydrogel.

3. The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, comprising 0.01 to 10% by weight of at least one of the ceramide or pseudoceramide relative to the total weight of the ceramide-conjugated hyaluronic acid hydrogel.

4. The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein the hyaluronic acid or hyaluronate salt of the hyaluronic acid hydrogel is chemically crosslinked with a crosslinking agent.

5. 5. The ceramide-conjugated hyaluronic acid hydrogel according to claim 4, wherein the crosslinking agent is at least one selected from the group consisting of a sulfone-based crosslinking agent, an epoxide-based crosslinking agent, and a phosphate-based crosslinking agent.

6. The crosslinking agent may be polyethylene glycol diglycidyl ether, sodium trimetaphosphate, epichlorohydrin, epibromohydrin, 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, or ether), propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polyglycerol polyglycidyl ether, diglycerol polyglycidyl ether 5. The ceramide-conjugated hyaluronic acid hydrogel according to claim 4, wherein the ceramide-conjugated hyaluronic acid hydrogel is at least one selected from the group consisting of glycerol polyglycidyl ether, trimethylpropane polyglycidyl ether, 1,2-(bis(2,3-epoxypropoxy)ethylene), pentaerythritol polyglycidyl ether, and sorbitol polyglycidyl ether.

7. The ceramide may be selected from the group consisting of Ceramide NP, Ceramide NS, Ceramide AS, Ceramide EOS, Ceramide NDS, Ceramide ADS, Ceramide EODS, Ceramide AP, Ceramide EOP, Ceramide NH, Ceramide AH, Ceramide EOH, and the like.

2. The ceramide-conjugated hyaluronic acid hydrogel of claim 1, wherein the ceramide is at least one selected from the group consisting of hydroxypalmitoylsphinganine, ...

8. The pseudoceramide may be hydroxypropyl bispalmitamide MEA, hydroxypropyl bisstearamide MEA, hydroxypropyl bislauramide MEA, hydroxypropyl bisisostearamide MEA, bis-hydroxyethyl tocopheryl succinoylamide hydroxypropane ...

2. The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein the ceramide is at least one selected from the group consisting of hydroxypropyl hydroxypropyl palmitamide (CETYL-PG HYDROXYETHYL PALMITAMIDE), myristoyl / palmitoyl oxostearamide / arachamide MEA, and bis-palmitoyl tromethamine.

9. 2. The ceramide-bound hyaluronic acid hydrogel according to claim 1, wherein the average diameter of the emulsion particles is 0.1 to 100 μm.

10. The hyaluronic acid hydrogel to which the ceramide is bound has a Tan δ of 0.01 to 2; The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein Tan δ is calculated by the following formula (1): [Equation 1]

11. The swelling degree of the ceramide-bound hyaluronic acid hydrogel is 10 to 300; The ceramide-conjugated hyaluronic acid hydrogel according to claim 1, wherein the swelling degree is measured by the following swelling degree measurement method: [Method for measuring swelling degree] Swelling degree = weight of ceramide-bonded hyaluronic acid hydrogel before drying / weight measured after drying the ceramide-bonded hyaluronic acid hydrogel at 60°C for 12 hours.

12. A composition comprising the ceramide-conjugated hyaluronic acid hydrogel of any one of claims 1 to 11.

13. The composition of claim 12, wherein the composition is a solubilized formulation or a clear formulation.

14. A method for producing a ceramide-conjugated hyaluronic acid hydrogel according to any one of claims 1 to 11, comprising: (a) mixing at least one of ceramide or pseudoceramide, an emulsifier, and water to prepare a ceramide emulsion composition; (b) mixing the produced ceramide emulsion composition with at least one of hyaluronic acid or a hyaluronate salt and a crosslinking agent to obtain a hyaluronic acid hydrogel with emulsion particles containing at least one of ceramide or pseudo-ceramide bound thereto.

15. The method for producing a ceramide-bound hyaluronic acid hydrogel according to claim 14, wherein the ceramide emulsion composition comprises ceramide emulsion particles.

16. The step (b) of obtaining a hyaluronic acid hydrogel having emulsified particles containing at least one of ceramide and pseudoceramide bound thereto, The method for producing a ceramide-bound hyaluronic acid hydrogel according to claim 14, wherein the ceramide emulsion composition produced in (a) is mixed with hyaluronic acid or a hyaluronate and a crosslinking agent to obtain a gel mixture, and the resulting gel mixture is swelled and then pulverized to obtain a hyaluronic acid hydrogel to which emulsion particles containing at least one of ceramide and pseudo-ceramide are bound.

17. and mixing the ceramide-conjugated hyaluronic acid hydrogel according to any one of claims 1 to 11 with purified water.

18. The method of claim 17, wherein the mixing step is carried out at ambient temperature.

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