Ferulic acid-containing oil-based composition

Abstract

The invention provides an oil-based composition containing isopropyl lauroyl sarcosinate and ferulic acid, which is characterized in that the weight ratio of ferulic acid to isopropyl lauroyl sarcosinate is less than or equal to 1 / 9. The invention also relates to an application of the oil-based composition containing the isopropyl lauroyl sarcosinate and the ferulic acid in an external preparation for the skin, wherein the external preparation for the skin is selected from skincare essence oil, face cream and emulsion.

Description

Technical Field

[0001] The invention belongs to the field of cosmetics, and in particular relates to an oil-based composition containing ferulic acid. Background Art

[0002] Ferulic acid is a plant phenolic acid that is commonly found in nature. It is found in high concentrations in cereals such as wheat, rice, and oats. It is a component of plant cell walls when cross-linked with polysaccharides and lignin. Ferulic acid is also found in high concentrations in traditional Chinese medicines such as Ferula, Angelica, Chuanxiong, Cimicifuga, and Semen Ziziphi Spinosae. It is one of the active ingredients of these traditional Chinese medicines and is often used as one of the quality indicators of traditional Chinese medicines.

[0003] The structure of ferulic acid is as follows:

[0004]

[0005] The chemical name of ferulic acid is 4-hydroxy-3-methoxycinnamic acid, which belongs to the class of hydroxycinnamic acids and usually exists in the form of trans isomers. As early as the 1970s and 1980s, Japanese researchers discovered that ferulic acid has antioxidant properties, and it has since been used in medicine, food, health products, cosmetics and other fields. In addition, ferulic acid also has the effects of whitening and sun protection. It can inhibit the proliferation of melanocytes and the activity of tyrosinase through competition with tyrosine, thereby inhibiting the formation of melanin. The vinyl group on its benzene ring has a strong ultraviolet absorption ability at 290-350nm, so ferulic acid has a significant alleviating effect on UVB-induced skin erythema. Ferulic acid also has soothing and antibacterial and anti-inflammatory effects, and can inhibit a variety of bacteria, thereby reducing the production of certain inflammatory proteins, which may be related to the mechanism of ferulic acid inhibiting N-acetyltransferase in bacteria.

[0006] Ferulic acid has a small molecular weight, but its oil solubility and water solubility are very poor. It is also very easy to be oxidized. It is greatly affected by factors such as light, pH value, temperature, etc., which makes it difficult to add to cosmetics. Even after dissolving, it is easy to precipitate. Ferulic acid in conventional commercial cosmetics is mostly conceptually added at a low concentration, or it is dissolved in a polyol solvent such as propylene glycol (such as The Ordinary 3% resveratrol + 3% ferulic acid essence), and the use feeling is poor. Due to the low solubility of ferulic acid in oil, it is currently not widely used in essence oil products. Based on previous research, a Chinese invention patent (CN111195217 B) discloses a single-phase oil composition containing ferulic acid, which is mainly dissolved by using a solubilizer PEG-20 glyceryl triisostearate. The invention found that when the weight ratio of ferulic acid to the solubilizer is less than 1 / 10, a single-phase oil composition containing ferulic acid can be prepared by heating to 80°C, and it can be stored for a long time after returning to room temperature. In addition, a Chinese invention patent (CN 116370328 B) invented a skin care composition and an external skin preparation, which selected a specific emulsifier, and improved the solubility of ferulic acid in polyol-modified oils by using sorbitol polyether-30 tetraoleate alone, polyglycerol-10 dioleate and polyglycerol-6 dicaprate in combination. Although the addition of the above-mentioned emulsifier / solubilizer components can help increase the solubility of ferulic acid, it is still not recommended to use a high amount of emulsifier components in the formula, especially emulsifiers containing PEG or polyether structures, which may also have the risk of dioxane residues and have a potential irritation to the skin.

[0007] Therefore, there is still a need in the art to find safer and more effective solvents to help improve the solubility and availability of ferulic acid. Summary of the invention

[0008] In one aspect, the present invention provides an oil-based composition comprising isopropyl lauroyl sarcosinate and ferulic acid, wherein the weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is ≤1 / 9.

[0009] In a preferred embodiment, the weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is 1 / 11 to 1 / 9, and more preferably, the weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is 1 / 10 to 1 / 9.

[0010] In a preferred embodiment, the composition of the present invention further comprises a solubilizer / emulsifier. Preferably, the solubilizer / emulsifier is selected from: PEG-20 glyceryl triisostearate, sorbitan polyether-30 tetraoleate, polyglyceryl-10 dioleate, polyglyceryl-6 dicaprate or a combination thereof. More preferably, the solubilizer is PEG-20 glyceryl triisostearate.

[0011] In a preferred embodiment, the weight ratio of ferulic acid:(isopropyl lauroyl sarcosinate+PEG-20 glyceryl triisostearate) is 1 / 10, and the weight ratio of isopropyl lauroyl sarcosinate to PEG-20 glyceryl triisostearate is ≥1.

[0012] In a preferred embodiment, the weight ratio of ferulic acid:(isopropyl lauroyl sarcosinate+PEG-20 glyceryl triisostearate) is 1 / 9, and the weight ratio of isopropyl lauroyl sarcosinate to PEG-20 glyceryl triisostearate is ≥2.

[0013] In another aspect, the present invention also relates to the use of the composition in external skin preparations.

[0014] In a preferred embodiment, the skin topical agent is selected from: skin care essence oil, face cream, and lotion. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 A photograph of Comparative Example A after preparation and standing is shown.

[0016] Figure 2 A photograph of Comparative Example B after preparation and standing is shown.

[0017] Figure 3 A photograph after the preparation of Example 4 is shown, wherein ferulic acid / PEG-20 glyceryl triisostearate=1 / 12.

[0018] Figure 4 A photograph after the preparation of Example 8 is shown, wherein ferulic acid / isopropyl lauroyl sarcosinate=1 / 9.

[0019] Figure 5 A photograph after the preparation of Example 22 is shown, wherein ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 6 / 3.

[0020] Figure 6 A photograph of the prepared comparative example 1 is shown, wherein ferulic acid / PEG-20 glyceryl triisostearate=1 / 10.

[0021] Figure 7 A photograph of Example 9 after standing for 2 weeks is shown, in which ferulic acid / isopropyl lauroyl sarcosinate=1 / 8. DETAILED DESCRIPTION

[0022] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, preferred methods and materials are described herein.

[0023] In order to provide a more concise description, some quantitative expressions given herein are not modified by the term "about". It should be understood that, whether or not the term "about" is explicitly used, each amount given herein is intended to refer to the actual given value, and is also intended to refer to the approximate values ​​of these given values ​​that can be reasonably inferred by a person of ordinary skill in the art, including the approximate values ​​of these given values ​​caused by experimental and / or measurement conditions. In addition, some quantitative expressions herein are described as a range of about X amount to about Y amount. It should be understood that when describing a range, the range is not limited to the upper and lower limits described, but should include the entire range of about X amount to about Y amount or any amount therebetween.

[0024] The object of the present invention is to provide an oil-based system composition containing ferulic acid, wherein the oil-based system composition contains no or only a small amount of emulsifier / solubilizer components, can be applied to essential oil products, and has good skin safety.

[0025] Ferulic acid

[0026] Due to its limited solubility and its easy oxidation and inactivation, ferulic acid has great technical barriers in its application in cosmetics. The purpose of the present invention is to find a safer and more effective way to help improve the solubility and utilization of ferulic acid.

[0027] The present invention provides an oil-based system composition containing ferulic acid, and the oil-based system composition does not contain or contains only a small amount of emulsifier / solubilizer components, can be applied to essential oil products, and has good skin safety. In a specific embodiment, the composition of the present invention uses ferulic acid purchased from Aoli Oil Press Co., Ltd.

[0028] In some embodiments, the composition of the present invention comprises 0.1-3 wt% ferulic acid. In a preferred embodiment, the composition of the present invention comprises 0.5-1.5 wt% ferulic acid, more preferably 1 wt% ferulic acid.

[0029] Isopropyl Lauroyl Sarcosinate

[0030] Isopropyl Lauroyl Sarcosinate is a condensation product composed of three monomers: lauric acid, sarcosine and isopropyl alcohol. It is a new type of amino acid-derived oil. It is mainly used as an emollient in cosmetics. It can provide good skin moisturizing effect, has good silkiness and skin-friendliness, and has good compatibility with most oils. At the same time, due to its high safety, especially the lack of acne risk, Isopropyl Lauroyl Sarcosinate has gradually become a preferred ingredient in cosmetics. It also has good solubility and permeability, and has excellent solubility for a variety of insoluble ingredients. It can help some insoluble active ingredients to better dissolve and penetrate into the skin, thereby enhancing the efficacy of cosmetics. Due to its advantages of being colorless, odorless, non-irritating to the skin, and non-sensitizing, Isopropyl Lauroyl Sarcosinate has gradually been widely used in various fields of cosmetics, including skin care products, makeup products, and personal care products.

[0031] The structure of isopropyl lauroyl sarcosinate is as follows:

[0032]

[0033] The present invention unexpectedly discovered that lauroyl sarcosine isopropyl has a good ability to dissolve ferulic acid. When the weight ratio of lauroyl sarcosine isopropyl to ferulic acid is ≥9:1, a clear, transparent and stable ferulic acid oil-based composition can be obtained.

[0034] A Chinese patent (CN 114869790 B) provides an antioxidant composition containing ferulic acid, comprising 0.5-4% ferulic acid and 1-20% stabilizer and optional water, wherein the stabilizer is selected from one or more of sodium ascorbyl phosphate, polyglycerol-10 isostearate, isopropyl lauroyl amino acid and 1,3-butylene glycol. After analysis, it was found that "isopropyl lauroyl amino acid" should actually be "isopropyl lauroyl sarcosine". The invention found that sodium ascorbyl phosphate, isopropyl lauroyl amino acid and polyglycerol-10 isostearate can help improve the solubility of ferulic acid in water, and the solubility of ferulic acid can reach a maximum of 3.68% when the three ingredients are used in combination, wherein sodium ascorbyl phosphate is the key factor in improving the solubility of ferulic acid. The invention also found that sodium ascorbyl phosphate can protect ferulic acid in a water-alcohol system, so the composition of the invention can contain a high content of ferulic acid and make it stable. As can be seen from the examples, ferulic acid has a very low solubility in pure water. When isopropyl lauroyl sarcosinate and water are used as a solvent in a ratio of 20:80, the solubility of ferulic acid in water can be improved. However, since isopropyl lauroyl sarcosinate itself is oily and insoluble in water, the system containing isopropyl lauroyl sarcosinate-water-ferulic acid will eventually form two stratified phases, rather than a uniform appearance. Therefore, this invention and the composition containing isopropyl lauroyl sarcosinate and ferulic acid described in the present invention for a transparent oil-based system are different technical directions.

[0035] Chinese patent (CN 114786782 B) invented a stable composition comprising cinnamic acid derivatives and specific ingredients, pH ≤ 4.5. The composition comprises ferulic acid and at least one lipophilic antioxidant and at least one oil and water, wherein the lipophilic antioxidant is selected from tocopherol, pentaerythritol tetra (di-tert-butyl hydroxyhydrocinnamate) ester and mixtures thereof, and the oil is a combination of isopropyl lauroyl sarcosinate and caprylic acid / capric acid / succinic acid triglyceride. In a preferred embodiment, when 0.5% ferulic acid, 6.0% isopropyl lauroyl sarcosinate and 0.5% caprylic acid / capric acid / succinic acid triglyceride are satisfied, a relatively stable O / W emulsion can be obtained, wherein isopropyl lauroyl sarcosinate / ferulic acid=12 / 1. This invention patent is to dissolve ferulic acid in the oil phase, use two kinds of oils, isopropyl lauroyl sarcosine and caprylic acid / capric acid / succinic acid triglyceride, to synergistically dissolve ferulic acid, and then prepare it into an O / W emulsion through emulsification technology, and finally achieve the stability of ferulic acid in the O / W emulsion by adjusting the pH of the emulsion to 4.5 or below, which is manifested as good color and smell and no crystallization. This patent mainly realizes the loading of ferulic acid through an emulsification system, which is a different technical direction from the composition containing isopropyl lauroyl sarcosine and ferulic acid described in the present invention for a transparent oil-based system. In addition, since isopropyl lauroyl sarcosine and caprylic acid / capric acid / succinic acid triglyceride are both oils, the system containing isopropyl lauroyl sarcosine / caprylic acid / capric acid / succinic acid triglyceride-water-ferulic acid will also form a layered two-phase appearance.

[0036] The present invention also unexpectedly discovered that when isopropyl lauroyl sarcosinate and an emulsifier / solubilizer are used in combination, the amount of the emulsifier / solubilizer originally required to dissolve ferulic acid can be significantly reduced, and a clear, transparent and stable ferulic acid oil-based composition can also be obtained.

[0037] Taking PEG-20 glyceryl triisostearate as an example, isopropyl lauroyl sarcosinate and PEG-20 glyceryl triisostearate are used as compound solvents. When isopropyl lauroyl sarcosinate / PEG-20 glyceryl triisostearate ≥ 2 / 1, as long as ferulic acid / total solvent meets ≤ 1 / 9, a clear, transparent and stable ferulic acid oil-based composition can be obtained at about 55°C. It is further explained that isopropyl lauroyl sarcosinate can cooperate with emulsifiers / solubilizers to dissolve ferulic acid, and can reduce the amount of emulsifiers / solubilizers, improve the safety of the product to the skin, and can also reduce the temperature required for dissolution, which saves energy and improves the dissolution efficiency. This may be because the carboxyl and amino groups in the structure of isopropyl lauroyl sarcosinate can form stronger hydrogen bonding forces with the PEG chains in the structure of PEG-20 glyceryl triisostearate. This stronger force interacts with the phenolic hydroxyl groups of ferulic acid, entangles and locks the active molecules in a larger "cage-like" structure, thereby helping ferulic acid to dissolve better.

[0038] Therefore, the present invention compounds ferulic acid with isopropyl lauroyl sarcosinate for the first time, and the obtained oil-based composition can maintain the stability of ferulic acid. In addition, compounding ferulic acid, isopropyl lauroyl sarcosinate and a solubilizing agent such as PEG-20 glyceryl triisostearate can greatly reduce the amount of solubilizing agent originally required to dissolve ferulic acid, and can also obtain a clear, transparent and stable ferulic acid oil-based composition.

[0039] In some embodiments, the composition of the present invention comprises 0.5-10 wt% of isopropyl lauroyl sarcosinate. In a preferred embodiment, the composition of the present invention comprises 1-5 wt%, more preferably 3-5 wt% of isopropyl lauroyl sarcosinate.

[0040] Oil-based compositions

[0041] The invention provides an oil-based composition comprising ferulic acid and isopropyl lauroyl sarcosinate, wherein the weight ratio of ferulic acid to isopropyl lauroyl sarcosinate is ≤1 / 9.

[0042] In some embodiments, the weight ratio of ferulic acid / isopropyl lauroyl sarcosinate in the composition of the present invention is 1 / 11 to 1 / 9. In a preferred embodiment, the weight ratio of ferulic acid / isopropyl lauroyl sarcosinate in the composition of the present invention is 1 / 10 to 1 / 9, more preferably 1 / 10.

[0043] In some embodiments, the composition of the present invention further comprises a solubilizer / emulsifier. In a preferred embodiment, the solubilizer / emulsifier is selected from: PEG-20 glyceryl triisostearate, sorbitan polyether-30 tetraoleate, polyglyceryl-10 dioleate, polyglyceryl-6 dicaprate or a combination thereof. In a preferred embodiment, the solubilizer is PEG-20 glyceryl triisostearate.

[0044] In some embodiments, the composition of the present invention comprises 0.5-10 wt% solubilizer / emulsifier. In a preferred embodiment, the composition of the present invention comprises 0.5-3 wt% solubilizer / emulsifier.

[0045] Composition of the present invention is an oil-based system, for example, an oil-based system with a grease content of at least 20 wt %. In some embodiments, the grease content of the oil-based system is at least 30 wt %, at least 40 wt %, at least 50 wt %, at least 60 wt %, at least 70 wt %, at least 75 wt %. In a preferred embodiment, the grease content of the oil-based system is 20-85 wt %, preferably 30-85 wt %, 40-85 wt %, 50-85 wt %, 60-85 wt %, 70-85 wt %, 75-85 wt %.

[0046] In some embodiments, when the weight ratio of ferulic acid to the mixed solvent (lauroyl sarcosine isopropyl compounded with PEG-20 glyceryl triisostearate) is 1 / 10, a clear and transparent ferulic acid oil-based system composition can be obtained when lauroyl sarcosine isopropyl / PEG-20 glyceryl triisostearate satisfies ≥1. In some embodiments, when the weight ratio of ferulic acid to the mixed solvent (lauroyl sarcosine isopropyl compounded with PEG-20 glyceryl triisostearate) is 1 / 10, a clear and transparent ferulic acid oil-based system composition can be obtained when lauroyl sarcosine isopropyl / PEG-20 glyceryl triisostearate satisfies ≥1.5.

[0047] In some embodiments, when the weight ratio of ferulic acid / mixed solvent (isopropyl lauroyl sarcosinate combined with PEG-20 glyceryl triisostearate) is 1 / 9, and the ratio of isopropyl lauroyl sarcosinate / PEG-20 glyceryl triisostearate is ≥ 6 / 3 (i.e., 2 / 1), a clear and transparent ferulic acid oil-based system composition can be obtained, and the long-term stability is good.

[0048] The present invention is further described below in conjunction with specific examples. It is necessary to point out that the examples are only used to further illustrate the present invention and cannot be construed as limiting the scope of the present invention. Those skilled in the art can make some non-essential improvements and adjustments based on the content of the present invention described above. The test methods in the following examples that do not specify specific conditions are usually based on conventional conditions or the conditions recommended by the manufacturer. Unless otherwise stated, all percentages and parts are by weight.

[0049] 1. Experimental Materials

[0050]

[0051] 2. Experimental Instruments

[0052] 1. Weighing balance METTLER TOLEDO PL602-S

[0053] 2. Fixed agitator IKA RW20

[0054] 3. Electric constant temperature water bath Shanghai Yiheng Scientific Instrument Co., Ltd. HWS28

[0055] 3. Embodiment and process description

[0056] First, Tables 1-3 respectively study the solubility of ferulic acid in common oil solvents (caprylic / capric triglyceride, coconut oil alcohol-caprylate / caprate and dibutyl adipate).

[0057] Table 1: Dissolution of ferulic acid in caprylic / capric triglyceride (heated to 80°C)

[0058] Ferulic acid 1 1 1 Caprylic / capric triglyceride 10 20 30 Phenomenon Insoluble Insoluble Insoluble

[0059] Table 2: Dissolution of Ferulic Acid in Coconut Oil Caprylate / Caprate (heated to 80°C)

[0060] Ferulic acid 1 1 1 Coco-Caprylate / Caprate 10 20 30 Phenomenon Insoluble Insoluble Insoluble

[0061] Table 3: Dissolution of ferulic acid in dibutyl adipate (heated to 80°C)

[0062]

[0063] The following example studies the dissolution of ferulic acid in PEG-20 glyceryl triisostearate.

[0064] Example 1: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 20

[0065] Weigh 0.5 g of ferulic acid and 10 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80°C, keep stirring until completely dissolved, let stand and cool to room temperature for use.

[0066] Example 2: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 15

[0067] Weigh 0.5 g of ferulic acid and 7.5 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80°C, keep stirring until completely dissolved, let stand and cool to room temperature for use.

[0068] Example 3: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 13

[0069] Weigh 0.5 g of ferulic acid and 6.5 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80°C, keep stirring until completely dissolved, let stand and cool to room temperature for use.

[0070] Example 4: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 12

[0071] Weigh 0.5 g of ferulic acid and 6.0 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80°C, keep stirring until completely dissolved, let stand and cool to room temperature for use.

[0072] Example 5: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 11

[0073] Weigh 0.5 g of ferulic acid and 5.5 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80°C, keep stirring until completely dissolved, let stand and cool to room temperature for use.

[0074] Comparative Example 1: Ferulic acid / PEG-20 glyceryl triisostearate = 1 / 10

[0075] Weigh 0.5 g of ferulic acid and 5.0 g of PEG-20 glyceryl triisostearate respectively, mix thoroughly, heat to above 80° C., and keep stirring for 30 minutes. If the two are still not completely dissolved or are not fully dissolved,

[0076] Test Example 1: Room Temperature Stability Test

[0077] The samples prepared in Examples 1-5 and Comparative Example 1 were stored at room temperature and protected from light, and the appearance of the samples was observed for one month. The results of the inspection test are recorded in the following table.

[0078] Table 4 shows the stability of samples with different ratios of ferulic acid / PEG-20 glyceryl triisostearate at room temperature.

[0079] Table 4

[0080]

[0081]

[0082] As shown in Table 4, it can be seen from Examples 1-5 and Comparative Example 1 that when ferulic acid and PEG-20 glyceryl triisostearate are mixed and heated to above 80°C, a clear and transparent ferulic acid oil phase composition can be obtained by satisfying ferulic acid / PEG-20 glyceryl triisostearate ≤ 1 / 11, but when ferulic acid / PEG-20 glyceryl triisostearate = 1 / 10, it still cannot be dissolved above 80°C. The long-term stability results show that a clear, transparent and stable ferulic acid oil-based composition can be obtained when ferulic acid / PEG-20 glyceryl triisostearate ≤ 1 / 12.

[0083] The following example shows the dissolution of ferulic acid in isopropyl lauroyl sarcosinate.

[0084] Example 6: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 11

[0085] Weigh 0.5 g of ferulic acid and 5.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 55°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0086] Example 7: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 10

[0087] Weigh 0.5 g of ferulic acid and 5.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 55°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0088] Example 8: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 9

[0089] Weigh 0.5 g of ferulic acid and 4.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 55°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0090] Example 9: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 8

[0091] Weigh 0.5 g of ferulic acid and 4.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 65°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0092] Example 10: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 8

[0093] Weigh 0.5 g of ferulic acid and 4.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0094] Example 11: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 7

[0095] Weigh 0.5 g of ferulic acid and 3.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 75°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0096] Example 12: Ferulic acid / lauroyl sarcosine isopropyl ester = 1 / 7

[0097] Weigh 0.5 g of ferulic acid and 3.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0098] Comparative Example 2: Ferulic acid / Isopropyl lauroyl sarcosinate = 1 / 6

[0099] Weigh 0.5 g of ferulic acid and 3.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, and heat to above 80°C. If the two still cannot be dissolved, let them stand and cool to room temperature to completely precipitate.

[0100] Test Example 2: Room Temperature Stability Test

[0101] The samples prepared in Examples 6-12 were stored at room temperature and protected from light, and the appearance of the samples was observed for one month. The results of the inspection test are recorded in the following table.

[0102] Table 5 shows the stability of samples with different ratios of ferulic acid / isopropyl lauroyl sarcosinate at room temperature.

[0103] Table 5

[0104]

[0105]

[0106] *Comparative Example 2 showed crystallization of ferulic acid at the end of preparation.

[0107] As shown in Table 5, from Examples 6-8, when ferulic acid / lauroyl sarcosine isopropyl ester≤1 / 9, a clear and transparent ferulic acid oil phase composition can be obtained at more than 55°C, and the long-term stability is good. From Examples 9-12, when ferulic acid / lauroyl sarcosine isopropyl ester=1 / 8, it is necessary to be heated to at least 65°C to dissolve ferulic acid, but a small amount of crystallization will be precipitated after standing for one week, and more crystallization will be precipitated as time goes on, and even if the dissolution temperature is further increased to more than 80°C, the stability test result is not improved. When ferulic acid / lauroyl sarcosine isopropyl ester=1 / 7, it is necessary to be heated to more than 75°C to dissolve ferulic acid, but crystallization will occur after standing for 24 hours, and even if the dissolution temperature is further increased to more than 80°C, the stability test result is the same. Further explanation, the dissolution effect of lauroyl sarcosine isopropyl ester on ferulic acid depends more on the relative proportion of the two, and the influence of dissolution temperature on the dissolution effect is less. Meanwhile, it can be further known from Comparative Example 2 that when the ratio of ferulic acid to isopropyl lauroyl sarcosinate is 1 / 6, ferulic acid cannot be dissolved even at a high temperature of 80° C. This indicates that to dissolve ferulic acid with isopropyl lauroyl sarcosinate, the amount of isopropyl lauroyl sarcosinate must be at least 9 times that of ferulic acid.

[0108] Comparative Example A: Water resistance test

[0109] Weigh 0.31g of ferulic acid and 20g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, cool to room temperature, add 80g of deionized water, stir evenly and let stand to obtain a two-phase liquid, in which the upper layer is a colorless transparent oil layer, the lower layer is a colorless transparent water layer, and there is a bubble layer between the two layers. Figure 1 shown.

[0110] Comparative Example B: Water resistance test

[0111] Weigh 0.5g of ferulic acid, 6.0g of isopropyl lauroyl sarcosinate and 0.5g of caprylic / capric / succinic triglyceride respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, cool to room temperature, add 93g of deionized water, stir evenly and let stand to obtain a two-phase liquid, of which the upper layer is a light yellow transparent oil layer and the lower layer is a colorless transparent water layer. Figure 2 shown.

[0112] In the following examples, PEG-20 glyceryl triisostearate and isopropyl lauroyl sarcosinate are used in combination as a mixed solvent, and an oil-based system composition containing ferulic acid is prepared by changing the ratio of ferulic acid / mixed solvent and the relative ratio of PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate in the mixed solvent.

[0113] Example 13: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 1 / 9

[0114] Weigh 0.5 g of ferulic acid, 0.5 g of PEG-20 glyceryl triisostearate and 4.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0115] Example 14: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 2 / 8

[0116] Weigh 0.5 g of ferulic acid, 1.0 g of PEG-20 glyceryl triisostearate and 4.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0117] Example 15: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 3 / 7

[0118] Weigh 0.5 g of ferulic acid, 1.5 g of PEG-20 glyceryl triisostearate and 3.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0119] Example 16: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 4 / 6

[0120] Weigh 0.5 g of ferulic acid, 2.0 g of PEG-20 glyceryl triisostearate and 3.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0121] Example 17: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 5 / 5

[0122] Weigh 0.5 g of ferulic acid, 2.5 g of PEG-20 glyceryl triisostearate and 2.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0123] Example 18: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 6 / 4

[0124] Weigh 0.5 g of ferulic acid, 3.0 g of PEG-20 glyceryl triisostearate and 2.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0125] Example 19: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 7 / 3

[0126] Weigh 0.5 g of ferulic acid, 3.5 g of PEG-20 glyceryl triisostearate and 1.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0127] Comparative Example 3: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 8 / 2

[0128] Weigh 0.5 g of ferulic acid, 4.0 g of PEG-20 glyceryl triisostearate and 1.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved and transparent in appearance, let stand and cool to room temperature, and ferulic acid completely precipitates and has a turbid appearance.

[0129] Test Example 3: Room Temperature Stability Test

[0130] Table 6 shows the sample information of Examples 13-19.

[0131] Table 6

[0132]

[0133] The samples prepared in Examples 13-19 were stored at room temperature and protected from light, and the appearance of the samples was observed for one month. The results of the inspection test are recorded in the following table.

[0134] Table 7 shows the stability of samples with different ratios of ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate (ferulic acid / mixed solvent=1 / 10) at room temperature.

[0135] Table 7

[0136]

[0137] *Comparative Example 3 showed crystallization of ferulic acid at the end of preparation.

[0138] By comparing the above examples 1-5 with the examples 13-19 in Tables 6-7, it can be seen that lauroyl sarcosine isopropyl compounded with PEG-20 glyceryl triisostearate has a better solubility for ferulic acid than using PEG-20 glyceryl triisostearate alone. When a certain amount of lauroyl sarcosine isopropyl compounded in the solvent, ferulic acid can be well dissolved when the ratio of ferulic acid / mixed solvent is 1 / 10, while when using PEG-20 glyceryl triisostearate alone, ferulic acid / PEG-20 glyceryl triisostearate cannot be dissolved even when heated for a long time at 80°C when the ratio of ferulic acid / PEG-20 glyceryl triisostearate is 1 / 10.

[0139] When ferulic acid / mixed solvent=1 / 10, when lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate meets ≥6 / 4 (i.e. 3 / 2), a clear and transparent ferulic acid oil-based system composition can be obtained. However, when lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate=5 / 5 and 4 / 6, very small crystals will appear after one week, but there is no significant change with the extension of the standing time. When lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate=3 / 7, although the initial state obtains a clear and transparent ferulic acid oil-based system composition, ferulic acid is precipitated after standing for 24h, which is not satisfied. As shown in Comparative Example 3, when lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate=2 / 8, after dissolving above 80°C, it is immediately precipitated when cooled to room temperature.

[0140] In summary, it can be seen that when ferulic acid / mixed solvent = 1 / 10 to dissolve ferulic acid, the ratio of isopropyl lauroyl sarcosinate / PEG-20 glyceryl triisostearate > 1 / 1 is required to achieve a relatively ideal dissolution effect.

[0141] Example 20: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 1 / 8

[0142] Weigh 0.5 g of ferulic acid, 0.5 g of PEG-20 glyceryl triisostearate and 4.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0143] Example 21: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 2 / 7

[0144] Weigh 0.5 g of ferulic acid, 1.0 g of PEG-20 glyceryl triisostearate and 3.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0145] Example 22: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 3 / 6

[0146] Weigh 0.5 g of ferulic acid, 1.5 g of PEG-20 glyceryl triisostearate and 3.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0147] Example 23: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 4 / 5

[0148] Weigh 0.5 g of ferulic acid, 2.0 g of PEG-20 glyceryl triisostearate and 2.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0149] Example 24: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 5 / 4

[0150] Weigh 0.5 g of ferulic acid, 2.5 g of PEG-20 glyceryl triisostearate and 2.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0151] Example 25: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 6 / 3

[0152] Weigh 0.5 g of ferulic acid, 3.0 g of PEG-20 glyceryl triisostearate and 1.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0153] Comparative Example 4: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 7 / 2

[0154] 0.5 g of ferulic acid, 3.5 g of PEG-20 glyceryl triisostearate and 1.0 g of isopropyl lauroyl sarcosinate were weighed separately, mixed thoroughly, and heated to above 80°C. If the mixture still could not be completely dissolved, it was allowed to stand and cool to room temperature. Ferulic acid was completely precipitated and had a turbid appearance.

[0155] Test Example 4: Room Temperature Stability Test

[0156] Table 8 shows the sample information for Examples 20-25.

[0157] Table 8

[0158]

[0159] The samples prepared in Examples 20 to 25 were stored at room temperature and protected from light, and the appearance of the samples was observed for one month. The results of the inspection test are recorded in the following table.

[0160] Table 9 shows the stability of samples with different ratios of ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate (ferulic acid / mixed solvent=1 / 9) at room temperature.

[0161] Table 9

[0162]

[0163] *Comparative Example 4 showed crystallization of ferulic acid at the end of preparation.

[0164] From Examples 20-25 and Comparative Example 4 in Tables 8-9, it can be seen that when ferulic acid / mixed solvent=1 / 9, a clear and transparent ferulic acid oil-based system composition can be obtained when the ratio of lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate is ≥6 / 3 (i.e., 2 / 1), and the long-term stability is good. When the ratio of lauroyl sarcosine isopropyl ester / PEG-20 glyceryl triisostearate is lower than 6 / 3 (i.e., 2 / 1), ferulic acid will crystallize.

[0165] Example 26: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 1 / 7

[0166] Weigh 0.5 g of ferulic acid, 0.5 g of PEG-20 glyceryl triisostearate and 3.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0167] Example 27: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 2 / 6

[0168] Weigh 0.5 g of ferulic acid, 1.0 g of PEG-20 glyceryl triisostearate and 3.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for use.

[0169] Example 28: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 3 / 5

[0170] Weigh 0.5 g of ferulic acid, 1.5 g of PEG-20 glyceryl triisostearate and 2.5 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0171] Example 29: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 4 / 4

[0172] Weigh 0.5 g of ferulic acid, 2.0 g of PEG-20 glyceryl triisostearate and 2.0 g of isopropyl lauroyl sarcosinate respectively, mix thoroughly, heat to above 80°C, stir until completely dissolved, let stand and cool to room temperature for later use.

[0173] Comparative Example 5: Ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate = 1 / 5 / 3

[0174] Weigh 0.5 g of ferulic acid, 2.5 g of PEG-20 glyceryl triisostearate and 1.5 g of isopropyl lauroyl sarcosinate respectively, mix them thoroughly, heat to above 80°C and keep stirring, but they still cannot dissolve.

[0175] Test Example 5: Room Temperature Stability Test

[0176] Table 10 shows the sample information for Examples 26-29.

[0177] Table 10

[0178] Example Embodiment 26 Embodiment 27 Embodiment 28 Embodiment 29 Ferulic acid / g 0.5 0.5 0.5 0.5 PEG-20 glyceryl triisostearate / g 0.5 1.0 1.5 2.0 Isopropyl lauroyl sarcosinate / g 3.5 3.0 2.5 2.0

[0179] The samples prepared in Examples 26-29 were stored at room temperature and protected from light, and the appearance of the samples was observed for one month. The results of the inspection test are recorded in the following table.

[0180] Table 11 shows the stability of samples with different ratios of ferulic acid / PEG-20 glyceryl triisostearate / isopropyl lauroyl sarcosinate (ferulic acid / mixed solvent=1 / 8) at room temperature.

[0181] Table 11

[0182]

[0183] *Comparative Example 5 Even under heating conditions of 80°C, ferulic acid still cannot be dissolved.

[0184] It can be seen from Examples 26-29 and Comparative Example 5 in Tables 10-11 that when ferulic acid / mixed solvent = 1 / 8, even if the ratio of lauroyl sarcosinate / PEG-20 glyceryl triisostearate reaches 7 / 1, a clear, transparent and stable ferulic acid oil-based system composition cannot be obtained; and when the ratio of lauroyl sarcosinate / PEG-20 glyceryl triisostearate is ≤3 / 5, ferulic acid cannot be dissolved at all.

[0185] Based on the above findings, when the ratio of lauroyl sarcosinate propyl ester / PEG-20 glyceryl triisostearate in the mixed solvent satisfies ≥6 / 3 (i.e., 2 / 1), the mixed solvent can achieve a clear and transparent ferulic acid oil-based system composition when the amount is 9 times that of ferulic acid, further indicating that the minimum amount of the mixed solvent that can better dissolve ferulic acid is 9 times that of ferulic acid, which is consistent with the ratio of solvent / solute when lauroyl sarcosinate propyl ester is used alone to dissolve ferulic acid in Example 8.

[0186] Compared with the case where PEG-20 glyceryl triisostearate is used alone to dissolve ferulic acid, a clear, transparent and stable ferulic acid oil-based composition can only be obtained when ferulic acid / PEG-20 glyceryl triisostearate ≤ 1 / 12. It can be seen that lauroyl sarcosinate propyl can indeed help PEG-20 glyceryl triisostearate to dissolve ferulic acid. Moreover, when the proportion of PEG-20 glyceryl triisostearate in the mixed solvent of the two is relatively small, the mixed solvent has the same dissolution effect on ferulic acid as lauroyl sarcosinate propyl itself, that is, solvent / ferulic acid ≥ 9 / 1.

[0187] Application Example 1: Preparation of skin care essence oil (solvent is PEG-20 glyceryl triisostearate)

[0188]

[0189] Application Example 2: Preparation of skin care essence oil (solvent is isopropyl lauroyl sarcosinate)

[0190]

[0191]

[0192] Application Example 3: Preparation of skin care essence oil (the solvent is a mixed solvent)

[0193]

[0194] Application Example 4: Preparation of facial cream

[0195]

[0196]

[0197] Application Example 5: Preparation of Emulsion

[0198]

Claims

1. An oil-based composition comprising isopropyl lauroyl sarcosinate and ferulic acid, characterized in that: The weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is ≤1 / 9.

2. The oil-based composition according to claim 1, characterized in that The weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is 1 / 11 to 1 / 9.

3. The oil-based composition according to claim 2, characterized in that The weight ratio of ferulic acid / isopropyl lauroyl sarcosinate is 1 / 10 to 1 / 9.

4. The oil-based composition according to claim 1, characterized in that The composition also includes a solubilizer / emulsifier.

5. The oil-based composition according to claim 4, characterized in that The solubilizer / emulsifier is selected from: PEG-20 glyceryl triisostearate, sorbitan polyether-30 tetraoleate, polyglyceryl-10 dioleate, polyglyceryl-6 dicaprate or a combination thereof.

6. The oil-based composition according to claim 4, characterized in that The solubilizer is PEG-20 glyceryl triisostearate.

7. The oil-based composition according to claim 6, characterized in that The weight ratio of ferulic acid: (isopropyl lauroyl sarcosinate + PEG-20 glyceryl triisostearate) is 1 / 10, and the weight ratio of isopropyl lauroyl sarcosinate to PEG-20 glyceryl triisostearate is ≥1.

8. The oil-based composition according to claim 6, characterized in that The weight ratio of ferulic acid: (isopropyl lauroyl sarcosinate + PEG-20 glyceryl triisostearate) is 1 / 9, and the weight ratio of isopropyl lauroyl sarcosinate to PEG-20 glyceryl triisostearate is ≥2.

9. Use of the composition according to any one of claims 1 to 8 in an external skin preparation.

10. The use according to claim 9, characterized in that The skin external preparation is selected from: skin care essential oil, face cream, and lotion.

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