Cosmetic composition containing ferulic acid as active ingredient
By combining alkaline amino acids and pH regulators in cosmetics, the decarboxylation reaction of ferulic acid is inhibited, and its stability and titer problems in cosmetics are solved, achieving improvements in dosage form stability and skin safety.
Patent Information
- Application Number
- CN202380043957.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-05-31
- Filing Date
- 2023-05-31
- Publication Date
- 2025-01-10
AI Technical Summary
Ferulic acid has problems with extremely low solubility and poor stability in cosmetics, especially when it is below pH 5, and decarboxylation reaction occurs at pH 5, resulting in a decrease in titer and reduced efficacy, and its derivatives cannot completely replace Awei. Acid skin improvement effect.
By adding basic amino acids and pH regulators to the cosmetic composition, the decarboxylation reaction of ferulic acid is inhibited, and its stability and titer are maintained, and discoloration and skin irritation are prevented.
The long-term storage stability and titer maintenance of ferulic acid are achieved, providing excellent dosage form stability, and reducing the risk of irritation to the skin.
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Figure CN119300801A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a cosmetic composition comprising ferulic acid as an effective ingredient, in particular to a cosmetic composition comprising ferulic acid, a basic amino acid and a pH regulator. Background Art
[0002] Ferulic acid exhibits a wide range of antimicrobial activities, is effective in neutralizing active oxygen, and can exhibit various effects as an external skin preparation such as anti-oxidation, UV blocking, and skin whitening effects, and therefore efforts are being made to develop cosmetics containing ferulic acid.
[0003] However, ferulic acid has extremely low solubility and low stability, and therefore can only be used in cosmetics with limitations. Specifically, since the pKa of ferulic acid is 4.61, there is a concern that it will precipitate at pH 5 or below, and at pH 5 or above, ferulic acid decomposes due to the decarboxylation reaction of ferulic acid, resulting in discoloration of the dosage form, reduced titer, and decreased efficacy of ferulic acid.
[0004] Therefore, in order to solve the problem of precipitation of ferulic acid at pH 5 or below, attempts have been made to improve solubility and storage stability by adding glycols and non-volatile polyols together with ferulic acid. However, the content of glycols should be increased according to the content of ferulic acid contained, and if glycols are used excessively, there is a concern that they may cause irritation to the skin.
[0005] In addition, the pH of human skin is 5.5 to 6, while the pKa of ferulic acid is lower than this, so there is also concern about skin irritation caused by it. Therefore, in terms of human safety, it is necessary to develop products with a pH similar to the skin pH or similar to that of conventional cosmetics while using a small amount of polyols.
[0006] Above pH 5, the solubility of ferulic acid is improved, which can reduce the amount of polyol used and reduce concerns about skin irritation. However, above pH 5, decarboxylation of ferulic acid occurs, resulting in rapid discoloration of the composition, reduced potency, and decreased efficacy, which may cause problems in the distribution of cosmetics.
[0007] In addition, attempts have been made to improve the dosage form stability of ferulic acid by derivatizing ferulic acid. However, while these derivatives improve the dosage form stability, they do not exhibit the same skin improvement effect as ferulic acid. Therefore, a solution is needed that can stably contain a certain amount of ferulic acid itself instead of derivatizing ferulic acid. Summary of the invention
[0008] Technical issues
[0009] Under the above background, the present inventors conducted studies to improve the stability of ferulic acid. As a result, they confirmed that if a basic amino acid and a pH adjuster are used in combination with ferulic acid, precipitation of ferulic acid can be prevented, and the decarboxylation reaction of ferulic acid can be inhibited, thereby preventing discoloration, reduction in potency and reduction in efficacy of the composition, thereby completing the present invention.
[0010] Therefore, an object of the present invention is to provide a cosmetic composition having excellent dosage form stability by preventing discoloration, precipitation, potency reduction, and efficacy reduction of a composition containing ferulic acid.
[0011] Technical Solution
[0012] The present invention provides a cosmetic composition, which comprises ferulic acid, a basic amino acid and a pH adjuster. The content of the ferulic acid is greater than 0.1% by weight relative to the weight of the entire composition, and the pH is 4.0 to 6.0.
[0013] In addition, the present invention provides a skin external preparation comprising the above composition.
[0014] Effects of the Invention
[0015] The present invention can maintain the potency of ferulic acid even in long-term storage by inhibiting the decarboxylation reaction of ferulic acid, and can prevent discoloration and efficacy reduction, so that a composition with excellent dosage form stability can be provided.
[0016] In addition, at the same time, concerns about precipitation can be reduced by improving the solubility of ferulic acid, and skin irritation can be prevented. BRIEF DESCRIPTION OF THE DRAWINGS
[0017] Figure 1 A photograph of the appearance of the composition according to Experimental Example 1 is shown.
[0018] Figure 2 A photograph of the appearance of the composition of Example 3 in Experimental Example 5 at the 4th week is shown.
[0019] Figure 3 The photographs of the appearance of Example 6 and Comparative Example 19 in Experimental Example 6 after being stored at 25 degrees for 6 months are shown. DETAILED DESCRIPTION
[0020] Hereinafter, the present invention will be described in detail.
[0021] However, the present invention can be modified in many ways and can have various forms, but the specific embodiments and descriptions described below are only used to help understand the present invention, and are not intended to limit the present invention to a specific disclosed form. It should be understood that the scope of the present invention includes all changes, equivalents and even substitutes contained in the thought and technical scope of the present invention.
[0022] The "ferulic acid (ferulic acid or 4-hydroxy-3-methoxycinnamic acid)" of the present invention is a phenolic compound, and its structure is the same as the following chemical formula 1. Ferulic acid can show effective effects in anti-oxidation, antibacterial effects, whitening effects due to inhibition of melanin regeneration, ultraviolet blocking effects, skin elasticity and anti-aging.
[0023] [Chemical formula 1]
[0024]
[0025] Ferulic acid has very low solubility in water and is easily oxidized, so it is limitedly used in cosmetics. Therefore, the present invention aims to provide a cosmetic composition that improves the dosage form stability of ferulic acid.
[0026] Ferulic acid begins to decompose by a decarboxylation reaction, which is accelerated above pH 5. The decarboxylation reaction of ferulic acid is shown in the following reaction formula 1.
[0027] [Reaction 1]
[0028]
[0029] The decarboxylation reaction of ferulic acid is carried out when the carboxyl functional group of ferulic acid with negative charge forms ion pair (ion-pair) with other positive charges in aqueous solution. It is expected that if the interaction between this charge can be suppressed, the decomposition of ferulic acid can be suppressed. For this reason, a scheme that can increase the required energy of decarboxylation reaction has been found. Although sodium or potassium ions have been considered as the above-mentioned positive charge, they are well ionized under aqueous solution state, and the binding energy is low, so they are not enough to improve the stability of ferulic acid. The inventor of the present invention has confirmed through numerous attempts that when using basic amino acids as cationic components, the stability of ferulic acid is improved, and has completed the present invention.
[0030] Therefore, the present invention provides a cosmetic composition comprising ferulic acid, a basic amino acid and a pH adjuster.
[0031] In one embodiment of the present invention, the content of the ferulic acid can be 0.1% by weight or more relative to the weight of the total composition. Specifically, it can be 0.1 to 10% by weight, more specifically, it can be 0.2% by weight or more, 0.3% by weight or more, 0.5% by weight or more, 0.8% by weight or more, 1% by weight or more, or 2% by weight or less, 8% by weight or less, 7% by weight or less, 6% by weight or less, or 5% by weight or less.
[0032] In one embodiment of the present invention, the above-mentioned basic amino acid can be any basic amino acid known to those skilled in the art, preferably, the basic amino acid can be selected from arginine, lysine, histidine and carnitine, or one or more of the group consisting of its acid or alkali, organic or mineral salt, most preferably, it can be carnitine or arginine. Basic amino acids are harmless to the human body, even if used in large quantities, not only there is no worry about skin irritation, but also the dosage form stability of ferulic acid can be improved. In particular, in addition to basic amino acids, for the same purpose, it is possible to consider using other ingredients with amine groups, such as triethanolamine (TEA) or tromethamine (tromethamine (TRIS)), but triethanolamine and tromethamine have the danger of amine unreacted products (N-nitrosodiethanolamine (NDELA) in the case of TEA, and secondary amines in the case of TRIS), even if the presence of such unreacted products does not reach a dangerous level, there may also be a problem of skin irritation, so basic amino acids are more preferred.
[0033] The content of the above basic amino acid may vary depending on the contents of ferulic acid and the pH adjuster and the pH of the composition, and is not limited as long as it is contained together with ferulic acid and the pH adjuster to achieve the pH range of the present invention.
[0034] In one embodiment of the present invention, the content of the basic amino acid can be 0.001 to 10% by weight relative to the weight of the total composition. Preferably, it can be 0.001 to 5% by weight, 0.01 to 3% by weight, or 0.01 to 1% by weight. When the basic amino acid is used within the above content range, the decarboxylation reaction of ferulic acid can be fully inhibited. When used in excess, there is a problem of possibly inducing skin irritation.
[0035] The pH of the composition may be 4.0 to 6.0. More specifically, the pH may be 4.4 to 6.0, 4.4 to 5.7, more preferably 4.4 to 5.5, 4.4 to 5.3 or 4.4 to 5.2. These pH values may be adjusted by a pH adjusting agent. If the pH value is increased, the solubility of ferulic acid may be improved, thereby reducing concerns about precipitation. However, the decomposition of ferulic acid and the reduction in potency may be accelerated, so the pH value needs to be adjusted within an appropriate range.
[0036] The pH adjuster described above does not simply increase or decrease pH like strong acids and strong bases, but is a component that minimizes pH changes and maintains it within a certain range through the action of conjugate bases / conjugate acids, and may be a pH buffer.
[0037] Specifically, the pH adjuster may be one or more selected from the group consisting of sodium citrate, potassium citrate, magnesium citrate, salicylic acid, glutamic acid, sodium phosphate, dibasic sodium phosphate, potassium phosphate, dipotassium phosphate, calcium phosphate, lactic acid, sulfuric acid, succinic acid, sodium lactate, potassium lactate, calcium lactate and magnesium lactate. Most preferably, it may be sodium citrate.
[0038] The pH adjuster not only plays a role in adjusting the pH of the composition, but also the functional groups such as carboxyl, hydroxyl or amine of the pH adjuster can interact with ferulic acid (for example, hydrogen bonding or van der Waals attraction), thereby inhibiting the decarboxylation reaction of ferulic acid like basic amino acids.
[0039] In addition, the pH adjuster may further contain EDTA.
[0040] The content of the above pH adjuster may vary depending on the content of ferulic acid and basic amino acid and the pH range of the composition, and is not limited as long as it is included together with ferulic acid and basic amino acid to achieve the pH of the present invention.
[0041] In one embodiment of the present invention, the content of the pH regulator can be 0.001 to 3% by weight relative to the weight of the total composition. More specifically, it can be 0.01 to 3% by weight, 0.1 to 2% by weight, or 0.15 to 1.5% by weight. If the content of the pH regulator is lower than the above content, it may not be possible to prevent the decomposition of ferulic acid and the increase in pH, thereby accelerating the decomposition of ferulic acid and reducing its potency. If the content is higher than the above content, it may affect the product quality.
[0042] In the present invention, both the pH adjuster and the basic amino acid can be used as a pH buffer, and the influence of ferulic acid on external changes can be reduced compared to when only a single material is used.
[0043] In one embodiment of the present invention, the weight ratio of ferulic acid, basic amino acid and pH adjuster may be 1:0.1-1.5:0.1-1.
[0044] The composition of the present invention may further comprise water and / or a polyol.
[0045] In one embodiment of the present invention, in order to avoid a sticky or heavy feeling during use, the content of the polyol may be 20% by weight or less, or 17.5% by weight or less, relative to the total weight of the composition. Preferably, the content may be 1 to 20% by weight, or 2 to 18% by weight, or 5 to 17.5% by weight.
[0046] The polyol may include one or more of glycerol and diols, and as the diol, it may be one or more selected from the group consisting of dipropylene glycol, butylene glycol, propylene glycol, ethoxydiglycol, 2,3-butylene glycol and 1,2-hexanediol. Preferably, in consideration of solubility, the polyol may be propylene glycol and / or ethoxydiglycol.
[0047] The above-mentioned polyol can be used as a humectant, and sufficient amounts can be used to stabilize the ferulic acid in the formulation, otherwise the problem of ferulic acid precipitation may occur. In the present invention, the usage amount of the polyol can be about 0.01 to 50 times, 0.05 to 30 times, 0.1 to 20 times, or 3 to 20 times relative to the content of ferulic acid. If the content of the polyol is too large, the problem of skin irritation may occur.
[0048] In one embodiment of the present invention, the water content may be 50% by weight or more, specifically 50 to 90% by weight, specifically 50 to 80% by weight, or 60 to 80% by weight.
[0049] In one embodiment of the present invention, the cosmetic composition of the present invention may not change color or precipitate or maintain potency even if stored at 50 degrees for 4 weeks.
[0050] In the present invention, "maintaining potency" means that ferulic acid is hardly decomposed even when stored at 50 degrees for 4 weeks. Specifically, the degree of decomposition of ferulic acid may be 10% or less, 5% or less, or may not be decomposed at all.
[0051] The present invention also provides a skin external preparation comprising the cosmetic composition.
[0052] The ingredients contained in the cosmetic composition of the present invention as active ingredients may include, in addition to the above-mentioned active ingredients, ingredients commonly used in cosmetic compositions, for example, antioxidants, stabilizers, solubilizers, vitamins, ultraviolet absorbers, preservatives, pH adjusters, pigments, pigments, fragrances and other conventional auxiliary agents and carriers, etc.
[0053] The cosmetic composition of the present invention can also be prepared in any dosage form commonly prepared in the field, for example, it can be formulated into a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, cleansing oil, powder foundation, emulsion foundation, wax foundation, mask, massage cream and spray, etc., but is not limited thereto. More specifically, it can be prepared in the dosage form of toner, lotion, softening lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, mask, spray or powder.
[0054] Each of the above-mentioned ingredients contained in the cosmetic composition of the present invention can preferably be contained in the cosmetic composition of the present invention within the range not exceeding the maximum usage amount specified in the relevant provisions of the "Cosmetic Use Permit" stipulated by the governments of various countries.
[0055] As another aspect, the present invention provides a method for preparing a cosmetic composition comprising ferulic acid, comprising the step of mixing ferulic acid with a basic amino acid and a pH adjuster to prepare a cosmetic composition having a pH of 4.0 to 6.0.
[0056] In the above preparation method, the content of ferulic acid may be 0.1 wt % or more relative to the total weight of the composition.
[0057] In the above preparation method, polyol and / or water may be further mixed.
[0058] The above preparation method may further include the step of mixing the above basic amino acid and pH adjuster and heating the mixture to 40 to 70 degrees.
[0059] The above preparation method can be used to prepare a cosmetic composition that is substantially free of precipitation, discoloration and / or potency reduction of ferulic acid. Specifically, it can be used to prepare a cosmetic composition that is substantially free of precipitation, discoloration and / or potency reduction of ferulic acid even if stored at 50 degrees for 4 weeks.
[0060] In the above-mentioned preparation method, the ferulic acid, basic amino acid, pH adjuster and cosmetic composition may be the same as those mentioned above.
[0061] As another aspect, the present invention provides a use of a basic amino acid and a pH adjuster for preparing a cosmetic composition containing ferulic acid with substantially no precipitation, discoloration and / or potency reduction of ferulic acid.
[0062] In the above-mentioned use, the ferulic acid, the basic amino acid, the pH adjuster and the cosmetic composition can be applied as described above.
[0063] In the present invention, "substantially free" may mean that even if stored at 50 degrees for 4 weeks, there is no precipitation, discoloration and / or potency reduction of ferulic acid, or the degree of decomposition of ferulic acid is 10% or less, or 5% or less.
[0064] Hereinafter, the present invention will be described in detail by the following experimental examples. However, the following experimental examples are only used to illustrate the present invention, and the content of the present invention is not limited by the following experimental examples. In addition, these experimental examples are only used to help understand the purpose of the present invention, so no matter in any sense, the scope of the present invention is not limited by them.
[0065] Example
[0066] In this example, the stability of ferulic acid according to pH (Experimental Example 1), the stability of ferulic acid according to the cationic component used to stabilize ferulic acid (Experimental Example 2), the type of amino acid (Experimental Example 3), and the stability of ferulic acid according to the content of the pH adjuster (Experimental Example 4) were confirmed. The results are shown in Experimental Examples 5 and 6, and the composition of the present invention was prepared, thereby conducting dosage form stability and potency analysis.
[0067] <Dosage Form Stability Evaluation>
[0068] The stability of the formulation was confirmed for the compositions prepared in the following experiments. Specifically, the compositions prepared in each experiment were stored at 25°C, 50°C, and -15°C for 4 weeks, or stored under sunlight exposure conditions for 8 hours, and then evaluated for discoloration and precipitation based on the following criteria.
[0069] 1. Color change
[0070] O: No color change or difficult to identify
[0071] △: The color change is noticeable, but not enough to affect preference
[0072] X: Color change is so severe that it has a negative impact on preference
[0073] 2. Precipitation
[0074] O: No precipitation
[0075] X: Precipitation observed
[0076] Experimental Example 1. Observation of pH stability of ferulic acid
[0077] According to the composition in Table 1 below, the compositions of Comparative Examples 1 to 5 having the following compositions were prepared by heating and mixing at 50° C. and then cooling.
[0078] [Table 1]
[0079] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Purified water margin margin margin margin margin Ferulic acid 0.3 0.3 0.3 0.3 0.3 Ethoxydiglycol 2.5 2.5 2.5 2.5 2.5 2,3-Butanediol 10 10 10 10 10 1,2-Hexanediol 2 2 2 2 2 Tromethamine - 0.05 0.2 0.3 0.4 pH 3 4 5 6 7
[0080] The compositions of Comparative Examples 1 to 5 prepared were subjected to the above-mentioned <Evaluation of Dosage Form Stability>. The results are shown in Tables 2 and 3.
[0081] [Table 2]
[0082] Color change evaluation Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 25℃ O O O O △ 50℃ O △ △ X X -15℃ O O O O O exposure O O O △ X
[0083] [Table 3]
[0084] Sedimentation evaluation Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 25℃ X O O O O 50℃ O O O O O -15℃ X X O O O exposure O O O O O
[0085] It can be confirmed from Table 3 above that when the pH is low, precipitation occurs under freezing conditions (Comparative Examples 1 and 2), and it can be confirmed from Table 2 that when the pH is high, discoloration occurs when exposed to high temperature or light. (Comparative Examples 2 to 5) That is, it can be confirmed that when the pH is 4 or more, the decomposition of ferulic acid accelerates over time, and it is necessary to suppress the decomposition of ferulic acid.
[0086] Experimental Example 2. Observation of the stability of ferulic acid according to cationic components
[0087] According to the composition in Table 4 below, the mixture was heated and mixed at 50°C and then cooled to prepare the compositions of Comparative Examples 6 to 9 having the following compositions. Appropriate amounts of arginine, tromethamine, NaOH, and KOH were added to adjust the pH to 5.
[0088] [Table 4]
[0089] Comparative Example 6 Comparative Example 7 Comparative Example 8 Comparative Example 9 Purified water margin margin margin margin Ferulic acid 0.5 0.5 0.5 0.5 Ethoxydiglycol 2.5 2.5 2.5 2.5 2,3-Butanediol 10 10 10 10 1,2-Hexanediol 2 2 2 2 Arginine Moderate - - - Tromethamine - Moderate - - NaOH - - Moderate - KOH - - - Moderate pH 5 5 5 5
[0090] The compositions of Comparative Examples 6 to 9 prepared were subjected to the above-mentioned <Evaluation of Dosage Form Stability>, and the results are shown in Tables 5 and 6.
[0091] [Table 5]
[0092] Color change evaluation Comparative Example 6 Comparative Example 7 Comparative Example 8 Comparative Example 9 25℃ O O O O 50℃ △ △ △ △ -15℃ O O O O exposure O O O O
[0093] [Table 6]
[0094] Sedimentation evaluation Comparative Example 6 Comparative Example 7 Comparative Example 8 Comparative Example 9 25℃ O O O O 50℃ O O O O -15℃ O O O O exposure O O O O
[0095] As shown in Tables 5 and 6 above, there was no significant difference in the stability of ferulic acid in Comparative Examples 6 to 9. However, it was confirmed that slight discoloration occurred at high temperature (50 degrees, 4 weeks). In addition, it was confirmed that all of the above Comparative Examples 6 to 9 were similar to Comparative Example 3 and did not precipitate under freezing conditions at pH 5. Therefore, it was confirmed that basic amino acids can be used as components that stabilize ferulic acid instead of other dangerous tromethamine and KOH and NaOH as strong bases.
[0096] Experimental Example 3. Observation of the stability of ferulic acid according to the type of amino acid
[0097] According to the compositions in Table 7 below, the compositions of Comparative Examples 10 to 13 having the following compositions were prepared by heating and mixing at 50° C. and then cooling.
[0098] [Table 7]
[0099] Comparative Example 10 Comparative Example 11 Comparative Example 12 Comparative Example 13 Purified water margin margin margin margin Ferulic acid 0.5 0.5 0.5 0.5 Ethoxydiglycol 2.5 2.5 2.5 2.5 2,3-Butanediol 10 10 10 10 1,2-Hexanediol 2 2 2 2 Arginine Moderate - - - Carnitine - Moderate - - Aspartic acid - - Moderate - Serine - - - Moderate pH 5 5 3 4
[0100] The compositions of Comparative Examples 10 to 13 prepared were subjected to the above-mentioned <Evaluation of Dosage Form Stability>, and the results are shown in Tables 8 and 9.
[0101] [Table 8]
[0102] Discoloration Comparative Example 10 Comparative Example 11 Comparative Example 12 Comparative Example 13 25℃ O O - O 50℃ △ △ - O -15℃ O O - O exposure O O - O
[0103] [Table 9]
[0104] Separation Comparative Example 10 Comparative Example 11 Comparative Example 12 Comparative Example 13 25℃ O O - X 50℃ O O - O -15℃ O O - X exposure O O - O
[0105] As shown in Tables 8 and 9, it was confirmed that both Comparative Examples 10 and 11 using arginine and carnitine among the basic amino acids had excellent dosage form stability. Comparative Example 12 using aspartic acid, one of the acidic amino acids, did not dissolve during the preparation process, so the contribution of ferulic acid to stabilization could not be confirmed. Comparative Example 13 using serine, one of the neutral amino acids, could not raise the pH to 4 or more even if an excessive amount was added, so precipitation occurred.
[0106] Experimental Example 4. Observation of stability according to pH adjuster content
[0107] According to the compositions in Table 10 below, the compositions of Comparative Examples 14 to 18 having the following compositions were prepared by heating and mixing at 50°C and then cooling.
[0108] [Table 10]
[0109] Comparative Example 14 Comparative Example 15 Comparative Example 16 Comparative Example 17 Comparative Example 18 Purified water margin margin margin margin margin Ferulic acid 0.5 0.5 0.5 0.5 0.5 Ethoxydiglycol 2.5 2.5 2.5 2.5 2.5 2,3-Butanediol 10 10 10 10 10 1,2-Hexanediol 2 2 2 2 2 Sodium Citrate 0.1 0.2 0.5 0.8 1.0 pH 4.3 4.6 5.2 5.5 5.7
[0110] The compositions of Comparative Examples 14 to 18 were subjected to the above-mentioned <Evaluation of Dosage Form Stability>. The results are shown in Tables 11 and 12.
[0111] [Table 11]
[0112] Color change evaluation Comparative Example 14 Comparative Example 15 Comparative Example 16 Comparative Example 17 Comparative Example 18 25℃ O O O O O 50℃ O O O O △ -15℃ O O O O O exposure O O △ △ △
[0113] [Table 12]
[0114] Sedimentation evaluation Comparative Example 14 Comparative Example 15 Comparative Example 16 Comparative Example 17 Comparative Example 18 25℃ O O O O O 50℃ O O O O O -15℃ X X O O O exposure O O O O O
[0115] It was confirmed that Comparative Examples 14 and 15, which contained 0.1 and 0.2 wt% of sodium citrate and had pH values of 4.3 and 4.6, respectively, precipitated ferulic acid under freezing conditions, but Comparative Examples 16 to 18, which contained 0.5, 0.8, and 1.0 wt% of sodium citrate and had pH values adjusted to 5.2 to 5.7, were stable under freezing conditions. However, Comparative Examples 16 to 18 had a problem of partial discoloration under light exposure conditions.
[0116] Experimental Example 5. Observation of the stability of the composition of the present invention
[0117] According to the composition in Table 13 below, the compositions of Examples 1 to 5 having the following compositions were prepared by heating and mixing at 50°C and then cooling.
[0118] [Table 13]
[0119] Example 1 Example 2 Example 3 Example 4 Example 5 Purified water margin margin margin margin margin Ferulic acid 0.5 0.5 0.5 0.5 0.5 Ethoxydiglycol 2.5 2.5 2.5 2.5 2.5 2,3-Butanediol 10 10 10 10 10 1,2-Hexanediol 2 2 2 2 2 Carnitine 1.2 1.2 1.2 1.2 1.2 Sodium Citrate 0.1 0.3 0.5 0.8 1.0 pH 4.4 4.9 5.2 5.5 5.7
[0120] The compositions of Examples 1 to 5 prepared were subjected to the above-mentioned <Evaluation of Dosage Form Stability>, and the results are shown in Tables 14 and 15.
[0121] [Table 14]
[0122] Color change evaluation Example 1 Example 2 Example 3 Example 4 Example 5 25℃ O O O O O 50℃ O O O O O -15℃ O O O O O exposure O O O O O
[0123] [Table 15]
[0124] Sedimentation evaluation Example 1 Example 2 Example 3 Example 4 Example 5 25℃ O O O O O 50℃ O O O O O -15℃ O O O O O exposure O O O O O
[0125] Based on the results of the amine component and the pH adjuster confirmed in Experimental Examples 1 to 4 above, the composition of this example was prepared. Although there was a slight difference in stability depending on the pH, it was confirmed that the composition exhibited excellent formulation stability as a whole.
[0126] Experimental Example 6. Observation of the stability of emulsion dosage form
[0127] According to Table 16 below, the water phase (raw materials 1 to 9) was mixed and heated to 50°C, and the polymer phase (raw materials 10 to 12) was mixed and maintained at 50°C. In addition, the oil phase (raw materials 13 and 14) was mixed and heated to 50°C. The water phase and the polymer phase were mixed at 5000 rpm for 5 minutes using a homomixer, and then the oil phase was added and further stirred at 5000 rpm for 5 minutes. Then, it was cooled to 30°C.
[0128] [Table 16]
[0129] Example 6 Comparative Example 19 1 Purified water margin margin 2 Propylene glycol 10 10 3 Ethoxydiglycol 2 2 4 glycerin 4 4 5 1,2-Hexanediol 1.5 1.5 6 EDTA 0.02 0.02 7 Carnitine 1.2 - 8 Sodium Citrate 0.2 - 9 Ferulic acid 0.5 0.5 10 Purified water Small amount Small amount 11 Polyacrylate Crosspolymer-6 1 1 12 Xanthan gum 0.2 0.2 13 Dimethicone 10 10 14 ABIL CARE XL 80* 1 1 pH 5.3 3.2
[0130] *ABIL CARE XL 80: Bis-PEG / PPG-20 / 5PEG / PPG-20 / 5 Dimethicone, Methoxy PEG / PPG-25 / 4 Dimethicone
[0131] The compositions of Example 6 and Comparative Example 19 prepared were evaluated in the same manner as in the above-mentioned <Evaluation of Dosage Form Stability>, except that discoloration was confirmed after storage for 6 months at 25°C, 50°C, and -15°C. The results are shown in Table 17.
[0132] [Table 17]
[0133] Color change evaluation Example 6 Comparative Example 19 25℃ O X 50℃ O X -15℃ O O exposure O X
[0134] It can be confirmed that the composition of Example 6 is superior to Comparative Example 19 in terms of dosage form stability. In particular, Figure 3As shown, the results of storage at 25°C for 6 months showed obvious color differences, which may be directly related to the quality of the product.
[0135] Experimental Example 7. Potency Analysis of Ferulic Acid by pH
[0136] It was confirmed how much the ferulic acid was reduced when the comparative examples 1, 3 and 5 prepared in the experimental example 1 and the example 3 prepared in the experimental example 5 were stored at 50°C for 4 weeks. That is, the ferulic acid was quantitatively measured relative to the initial content of ferulic acid to evaluate how much the ferulic acid was reduced. The initial value of ferulic acid in the comparative examples 1, 3 and 5 was 0.3% by weight, and that in the example 3 was 0.5% by weight.
[0137] [Table 18]
[0138] 50℃ 4 weeks (weight %) Reduction rate (%) pH Comparative Example 1 0.24 17 3.0 Comparative Example 3 0.23 20 5.0 Comparative Example 5 0.21 27 7.0 Example 3 0.50 0 5.2
[0139] When Comparative Examples 1, 3, and 5 were stored at 50°C for 4 weeks, decomposition of ferulic acid occurred, and it was confirmed that the potency decreased more seriously as the pH increased.
[0140] In addition, although Example 3 had the same pH of 5 as Comparative Example 3, the ferulic acid content was 0.50% by weight, and since ferulic acid was hardly decomposed, it was confirmed that the potency did not decrease at high temperatures and remained stable.
[0141] The degree of reduction of ferulic acid was also confirmed for the emulsion formulations prepared in Experimental Example 6, namely Example 6 and Comparative Example 19. The results are shown in Table 19 below.
[0142] [Table 19]
[0143] 50℃ 4 weeks (weight %) Reduction rate (%) pH Example 6 0.50 0 5.3 Comparative Example 19 0.43 14 3.2
[0144] As a result of checking the residual amount of ferulic acid under high temperature with time, it was confirmed that in Example 6, ferulic acid was not decomposed but was stable, but in Comparative Example 19, ferulic acid was decomposed.
Claims
1. A cosmetic composition comprising ferulic acid, a basic amino acid and a pH regulator, The content of the ferulic acid is 0.1% by weight or more relative to the weight of the entire composition. The pH is 4.0 to 6.
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2. The cosmetic composition according to claim 1, wherein The basic amino acid is at least one selected from the group consisting of arginine, lysine, histidine and carnitine.
3. The cosmetic composition according to claim 1, wherein The content of the basic amino acid is 0.001 to 10% by weight relative to the weight of the entire composition.
4. The cosmetic composition according to claim 1, wherein The pH adjuster is one or more selected from the group consisting of sodium citrate, potassium citrate, magnesium citrate, salicylic acid, glutamic acid, sodium phosphate, disodium phosphate, potassium phosphate, dipotassium phosphate, calcium phosphate, lactic acid, sulfuric acid, succinic acid, sodium lactate, potassium lactate, calcium lactate and magnesium lactate.
5. The cosmetic composition according to claim 1, wherein The content of the pH adjuster is 0.001 to 3% by weight relative to the weight of the entire composition.
6. The cosmetic composition according to claim 1, wherein More than one polyol may also be included.
7. The cosmetic composition according to claim 6, wherein The polyol is at least one selected from the group consisting of glycerin, dipropylene glycol, butylene glycol, propylene glycol, ethoxydiglycol, 2,3-butylene glycol, and 1,2-hexanediol.
8. The cosmetic composition according to claim 1, wherein The amount of water contained is 50% by weight or more relative to the weight of the entire composition.
9. The cosmetic composition according to claim 1, characterized in that: Even when stored at 50 degrees for 4 weeks, it will not change color or precipitate or maintain potency. 10 . A skin external preparation comprising the cosmetic composition according to claim 1 .
11. A method for preparing a cosmetic composition containing ferulic acid, comprising: A step of mixing ferulic acid with a basic amino acid and a pH adjuster to prepare a cosmetic composition having a pH of 4.0 to 6.
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12. The method for preparing a cosmetic composition comprising ferulic acid according to claim 11, wherein: The above-mentioned preparation method is used to prepare a cosmetic composition which is substantially free of precipitation, discoloration and / or potency reduction of ferulic acid.