Cosmetic Composition Comprising Stabilized Retinol

A cosmetic composition with retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate stabilizes retinol, addressing its instability and maintaining its efficacy in cosmetic products.

KR102995038B1Active Publication Date: 2026-07-27KOLMAR KOREA
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Patent Information

Authority / Receiving Office
KR · KR
Patent Type
Patents
Current Assignee / Owner
KOLMAR KOREA
Filing Date
2025-11-25
Publication Date
2026-07-27

AI Technical Summary

Technical Problem

Retinol is highly unstable and prone to oxidation, leading to a rapid decline in efficacy and potential skin irritation due to exposure to oxygen, light, heat, and humidity, which complicates its stable application in cosmetic products.

Method used

A cosmetic composition comprising retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate, formulated in specific weight percentages and ratios, to stabilize retinol and prevent oxidation during long-term storage.

Benefits of technology

The composition effectively maintains retinol's activity and prevents discoloration, ensuring its stability and efficacy in cosmetic formulations.

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Abstract

The present invention relates to a cosmetic composition containing stabilized retinol, and more specifically, to a cosmetic composition that effectively maintains the activity of retinol without degradation of potency or discoloration during long-term storage by including grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate.
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Description

Technology Field

[0001] The present invention relates to a cosmetic composition containing stabilized retinol, and more specifically, to a cosmetic composition comprising grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate, which effectively maintains the activity of retinol without degradation of potency or discoloration during long-term storage. Background Technology

[0002] Retinol has long been a highly regarded ingredient in the skincare field for its various effects, including wrinkle reduction, whitening, skin texture refinement, and reduced skin damage. Thanks to these outstanding benefits, consumer demand for retinol-containing products continues to rise, and numerous global and domestic cosmetics companies are competitively launching retinol-based functional products.

[0003] However, despite its high functionality, retinol possesses highly unstable characteristics. It easily decomposes and oxidizes due to exposure to oxygen in the air, light, heat, and humidity; this leads to a rapid decline in active efficacy, and oxidized retinol can cause skin irritation and side effects. Therefore, the technology to stably apply retinol to products has been a continuous and important subject of research in the cosmetics industry.

[0004] Accordingly, the inventors completed the present invention by preparing a cosmetic composition that prevents the oxidation of retinol by using a combination of grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate, prevents a decrease in potency and discoloration during long-term storage, and effectively maintains the activity of retinol. Prior art literature

[0005] Korean Registered Patent Publication No. 10-0570497 The problem to be solved

[0006] The present invention aims to provide a cosmetic composition comprising retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate.

[0007] The technical problems of the present invention are not limited to those mentioned above, and other unmentioned technical problems will be clearly understood by those skilled in the art from the description below. means of solving the problem

[0008] According to an embodiment of the present invention, a cosmetic composition comprising retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate is provided.

[0009] In addition, the retinol may be included in an amount of 0.01 to 0.5 weight% based on the total weight of the cosmetic composition.

[0010] In addition, the grapevine extract may be included in an amount of 0.005 to 0.5 weight% based on the total weight of the cosmetic composition.

[0011] In addition, the above pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate may be included in an amount of 0.1 to 1 weight% based on the total weight of the cosmetic composition.

[0012] In addition, the above pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate and grapevine extract may be mixed in a weight ratio of 1:0.025 to 0.1. Effects of the invention

[0013] The cosmetic composition according to the present invention contains grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate in optimal content and ratio, thereby enabling the stable maintenance of retinol within the formulation, which has the problem of poor stability despite its excellent skin condition improvement effect. Accordingly, the grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate according to the present invention prevent the oxidation of retinol, thereby preventing the decrease in potency and discoloration that occur during long-term storage and effectively maintaining the activity of retinol; thus, it can be applied to various cosmetics utilizing retinol. Brief explanation of the drawing

[0014] A brief description of each drawing is provided to help to better understand the drawings cited in the detailed description of the invention. Figure 1 is a figure showing whether discoloration occurred after storing Examples 1 to 3 at 5°C for 6 weeks. Specific details for implementing the invention

[0015] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by a skilled expert in the art to which the present invention pertains. In general, the nomenclature used herein is well known and commonly used in the art. Furthermore, in describing embodiments of the present invention, detailed descriptions of related known components or functions are omitted if it is determined that such detailed descriptions would hinder understanding of the embodiments of the present invention. Additionally, while embodiments of the present invention will be described below, the technical concept of the present invention is not limited or restricted thereto and can be modified and implemented in various ways by those skilled in the art.

[0016] In this specification, when a part is described as including a certain component, it means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. In this specification, the term "and / or" includes a combination of a plurality of related items or any one of a plurality of related items.

[0018] According to an embodiment of the present invention, a cosmetic composition comprising retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate is provided.

[0019] The retinol according to the present invention has various cosmetic effects such as wrinkle improvement, elasticity enhancement, skin texture improvement, and acne improvement; however, it is highly unstable to heat, light, temperature, moisture, oxygen, and the passage of time, and has stability issues such as easy oxidation when exposed to the atmosphere or in aqueous solutions, resulting in a decrease in potency and discoloration. Accordingly, the cosmetic composition according to the present invention is characterized by containing retinol while also including grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate in optimal amounts and ratios to stably maintain the retinol within the composition.

[0020] The retinol according to the present invention may be included in an amount of 0.01 to 0.5 weight% based on the total weight of the cosmetic composition, but is not limited thereto.

[0021] In the present invention, the grapevine extract is obtained by extracting a part of the grapevine. As an extraction solvent, one or more selected from the group consisting of water, alcohols having 1 to 4 carbon atoms, or mixed solutions thereof may be used; specifically, it may be ethanol, but is not limited thereto. The extraction method may use any extraction method known in the art, such as organic solvent extraction, hot water extraction, reflux extraction, and stirring, without limitation. Specifically, the grapevine may be immersed in a solvent, specifically ethanol, for primary extraction, and then subjected to a purification step by adding the solvent again, and subsequently dried to obtain the final extract. The grapevine extract may be included in an amount of 0.005 to 0.5 weight% based on the total weight of the cosmetic composition, specifically in an amount of 0.01 to 0.04 weight%, but is not limited thereto. If the above grapevine extract is included in an amount of less than 0.005% by weight, the desired antioxidant and retinol stabilization effects are negligible, and if it is included in an amount exceeding 0.5% by weight, there are problems such as the occurrence of floating particles, the development of a characteristic color, and high manufacturing costs, which reduces commercial viability.

[0022] In the present invention, pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate acts as a phenolic antioxidant to inhibit the oxidation of retinol. The pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate may be included in an amount of 0.1 to 1 weight% based on the total weight of the cosmetic composition, specifically in an amount of 0.2 to 0.6 weight%, but is not limited thereto. If the pentaerythrityl tetra-di-t-t-butylhydroxyhydrocinnamate is included in an amount less than 0.1 weight%, the desired antioxidant and retinol stabilization effects are negligible, and if it is included in an amount exceeding 1 weight%, there is a problem that precipitation may occur within the formulation and skin irritation may worsen.

[0023] The above pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate and grapevine extract may be mixed in a weight ratio of 1:0.025 to 0.1 to achieve a stabilizing effect of retinol.

[0024] The cosmetic composition according to the present invention contains grapevine extract and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate in an optimal content and ratio, thereby preventing oxidation of retinol, which prevents the decrease in potency and discoloration that occur during long-term storage and effectively maintains the activity of retinol. Thus, it can be applied to various cosmetics utilizing retinol, namely cosmetics exhibiting effects such as wrinkle improvement, elasticity enhancement, skin texture improvement, and acne improvement due to retinol.

[0025] In addition to the above-mentioned ingredients, the cosmetic composition according to the present invention may further include ingredients found in general cosmetic compositions, such as preservatives, functional ingredients, ion-chelating agents, disinfectants, pH adjusters, antioxidants, alcohols, plant extracts, fragrances, cooling agents, additives, etc. The amount of the above-mentioned ingredients is not particularly limited and can be easily selected by a person skilled in the art within a range that does not impair the purpose and effects of the present invention.

[0026] In addition, the cosmetic composition according to the present invention can be prepared in any formulation conventionally manufactured in the art, for example, as a solution, suspension, emulsion, paste, gel, cream, lotion, serum, essence, powder, soap, surfactant-containing cleansing, oil, spray, bead capsule, and pack, and specifically, can be formulated as a cream, lotion, serum, essence, pack, or bead capsule, but is not limited thereto.

[0028] In the following, examples and experimental examples are presented to further explain the present invention in more detail, but the present invention is not limited thereto.

[0030] [Preparation Example]

[0031] Preparation of Examples 1 to 3

[0032] The inventors prepared a cosmetic composition containing retinol as shown in Table 1 below, and pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate and grapevine extract to stabilize it. The unit of the ingredient content in Table 1 is weight%.

[0033]

[0034] Specifically, the grapevine extract was obtained by adding ethanol to obtain a crude extract, adding ethanol once more, purifying, and drying. Subsequently, the preparation of the cosmetic composition was carried out as follows. First, purified water, glycerin, methylpropanediol, 1,2-hexanediol, and disodium EDTA were dissolved in the aqueous phase, and then carbomer, a thickening agent, was dissolved. Tromethamine, a neutralizing agent, was added to this mixture, and retinol, an active ingredient, was dispersed. Separately, caprylic / capric triglyceride, an oil phase, was heated, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate was dissolved and added. The grapevine extract was added to the above mixture and mixed together to prepare the cosmetic compositions of Examples 1 to 3.

[0036] Preparation of Comparative Examples 1 to 4

[0037] As shown in Table 2 below, Comparative Example 1, which does not contain both pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate and grapevine extract, and Comparative Examples 2 to 4, which do not contain grapevine extract and contain only pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate, were prepared. The remaining components are the same as in Example 1, and the preparation method is the same as in the above example. The unit of the component content in Table 2 is weight%.

[0038]

[0039] Preparation of Comparative Examples 5 and 6

[0040] Comparative Examples 5 and 6 were prepared as shown in Table 3 below, containing only grapevine extract without pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate. The remaining ingredients are the same as in Example 1, and the preparation method is the same as in the above example. The unit of the ingredient content in Table 3 is weight%.

[0041]

[0042] Preparation of Comparative Examples 7 to 10

[0043] Comparative Examples 7 to 10 were prepared by adjusting the weight% of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate and grapevine extract as shown in Table 4 below. The remaining components are the same as in Example 1, and the preparation method is the same as in the above example. The unit of the component content in Table 4 is weight%.

[0044]

[0045] [Experimental Example]

[0046] Experimental Example 1. Potency Measurement

[0047] To confirm whether the compositions of the above examples and comparative examples could stably maintain retinol, the potency of retinol was measured. In the above examples and comparative examples, the initial potency of retinol in the composition was set to 100, and the retinol potency after 4 weeks (comparative example) or 6 weeks (example) was measured at 25°C, 40°C, and 50°C. Specifically, the retinol potency was calculated by analyzing the standard solution and the test solution under the same HPLC conditions. First, for the standard solution, approximately 10 mg of the retinol standard was accurately weighed, dissolved in methanol to make 100 mL, dispersed by ultrasound for 10 minutes, and filtered through a 0.45 μm filter to be used as the standard solution. For the test solution, an amount corresponding to approximately 10 mg of retinol in the product was accurately weighed, dissolved in methanol to make 100 mL, and subjected to ultrasound treatment to ensure sufficient extraction of the component. If dissolution was incomplete, extraction was performed by heating, and the extracted solution was filtered through a 0.45 μm filter to obtain the test solution. The prepared standard solution and test solution were analyzed under the following HPLC conditions. Detector: UV spectrophotometer (measurement wavelength 325 nm), injection volume: 10 μL, column: Symmetry C18 (150 × 4.6 mm, 5 μm), column temperature: 35 ℃, flow rate: 1.0 mL / min, mobile phase: 90% methanol. The results are shown in Tables 5 and 6 below.

[0048]

[0049]

[0050] As shown in Table 5, the compositions of Examples 1 to 3, containing pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate and grapevine extract in optimal amounts and ratios, were found to maintain the potency of retinol at 25°C, 40°C, and 50°C when stored for 6 weeks. In contrast, as shown in Table 6, the composition of Comparative Example 1, which did not contain either pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate or grapevine extract, showed a severe decrease in retinol potency under all temperature conditions, and Comparative Examples 2 to 6, which contained only one of pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate or grapevine extract, showed a decrease in potency at 40°C and 50°C when stored for 4 weeks, which is shorter than the examples. In addition, Comparative Example 7 or Comparative Example 8, which contained a small amount of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate or grapevine extract, also showed a decrease in potency at 40°C and 50°C. Meanwhile, Comparative Examples 9 and 10, which contained an excess amount of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate or grapevine extract, did not have potency issues, but problems such as discoloration, precipitation, and the formation of suspended particles occurred as described below.

[0052] Experimental Example 2. Confirmation of discoloration

[0053] To determine whether the compositions of the above examples and comparative examples could stably maintain retinol, the samples were stored for 4 weeks (comparative example) or 6 weeks (example) in a constant temperature bath maintained at 5, 40, or 50°C, and then the degree of discoloration was checked. After visually observing whether discoloration occurred, O was indicated if discoloration occurred and X was indicated if it did not. The results are shown in Tables 7 and 8 and Figure 1.

[0054]

[0055]

[0056] As shown in Table 7 and Figure 1, it was confirmed that the compositions of Examples 1 to 3, containing pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate and grapevine extract in optimal amounts and ratios, remained without discoloration under all temperature conditions even after storage for 6 weeks. In contrast, as shown in Table 8, the compositions of Comparative Example 1, which did not contain both pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate and grapevine extract, and Comparative Example 2, which did not contain grapevine extract but contained 0.2 wt% of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate, showed discoloration at all temperatures, while Comparative Examples 3 to 6, which contained only one of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate and grapevine extract, and Comparative Examples 7 to 10, which contained a small or excessive amount of pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate or grapevine extract, showed discoloration under high temperature conditions (40 or 50°C).

[0058] Through the experimental results above, it was confirmed that by including grapevine extract and pentaerythrityltetra-di-t-butylhydroxyhydrocinnamate at optimal concentrations, retinol can be stably maintained within the composition and its activity can be effectively displayed.

[0060] Foregoing, specific parts of the content of the present invention have been described in detail. It will be apparent to those skilled in the art that such specific descriptions are merely preferred embodiments and do not limit the scope of the present invention. Accordingly, the actual scope of the present invention is defined by the appended claims and their equivalents.

Claims

Claim 1 A cosmetic composition comprising retinol, grapevine extract, and pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate, wherein the grapevine extract is included in an amount of 0.005 to 0.5 weight% based on the total weight of the cosmetic composition, and the pentaerythrityl tetra-di-t-t-butylhydroxyhydrocinnamate is included in an amount of 0.1 to 1 weight% based on the total weight of the cosmetic composition. Claim 2 A cosmetic composition according to claim 1, wherein the retinol is included in an amount of 0.01 to 0.5 weight% based on the total weight of the cosmetic composition. Claim 3 delete Claim 4 delete Claim 5 A cosmetic composition according to claim 1, wherein the pentaerythrityl tetra-di-t-butylhydroxyhydrocinnamate and grapevine extract are mixed in a weight ratio of 1:0.025 to 0.

1. Claim 6 A cosmetic composition according to claim 1, wherein the potency of retinol is stably maintained.