Stepped hair color composition and cosmetic composition containing the same

Abstract

The present invention is characterized by providing a stepwise hair color composition that can develop color upon contact with oxygen by forming colloidal particles that can further contain a specific compound having a biphenyl core, a binder, and additionally, polyphenols. The composition allows for hair dyeing without hair damage or scalp hypersensitivity reactions, prevents phase separation and precipitation of the composition by forming the colloidal particles, exhibits excellent shelf life, can be formulated into various dosage forms, and exhibits excellent dyeing properties when repeatedly applied to hair.

Description

[Technical Field]

[0001] This invention claims the benefits as of the filing date of Korean Patent Application No. 10-2023-0036901, filed with the Korean Intellectual Property Office on March 21, 2023, and all of its contents are included in this invention.

[0002] This invention relates to a graduated hair color composition that does not induce hair damage or scalp hypersensitivity reactions, and a cosmetic composition containing the same.

[0003] This invention was supported by the research project: Development of traffic integration materials based on photoresponsive carbon nanomaterials (Research project name: Construction of research infrastructure for science and engineering, Project number: 1345350879, Project number: 2018R1A6A1A03023788, Research period: 2018.06.01~2023.02.28), and the research project: Research on cancer cell diagnostic and therapeutic properties utilizing cancer cell-specific mechanical properties and conductivity-responsive hydrogels (Research project name: Individual basic research project / mid-career follow-up research, Project number: RS-2023-00207925, Research period: 2023.03.01~2024.02.28). [Background technology]

[0004] Hair dyeing has been performed to color gray hair caused by aging, or to improve aesthetics by dyeing hair in a variety of colors or shades different from the existing ones. Conventional hair dyeing methods have involved applying a hair dye containing a hair dyeing composition to the hair and leaving it for a certain period of time to dye it. Recently, research has been conducted on methods that incorporate a hair dyeing composition into functional cosmetics for hair or scalp, thereby imparting both the inherent functions of the cosmetic and a hair dyeing effect.

[0005] Conventional hair dyeing compositions primarily contain oxidizing agents to break down and decolorize the melanin in the hair and oxidize the precursors of oxidative dyes. However, oxidizing agents such as hydrogen peroxide can damage the hair and irritate the scalp during the decolorization process, and oxidative dyes can cause allergic reactions on the scalp. In modern times, with increasing interest in both beauty and health, research is being conducted not only on the stability after dyeing, but also on methods that can improve the health of the hair and scalp. [Overview of the project] [Problems that the invention aims to solve]

[0006] The object of the present invention is to provide a DPC (Dark Polyphenol Complex), which is a stepwise hair color composition containing colloidal particles that can develop color upon contact with oxygen.

[0007] Another object of the present invention is to provide a cosmetic composition containing the aforementioned stepwise hair color composition. [Means for solving the problem]

[0008] A stepwise hair color composition according to one aspect of the present invention comprises colloidal particles containing a compound of the following chemical formula 1 and a binder, and the stepwise hair color composition can develop color upon contact with oxygen.

[0009] [ka]

[0010] During the ceremony, R1 is hydrogen, a hydroxyl group, or a carboxyl group. R2 and R3 are independent of each other: hydrogen, carboxyl group, C1-C 10 Alkyl alkyl group, C1-C 10 Haloalkyl groups, C1-C 10 Alkoxy group, C1-C 10 It is a haloalkoxy group, an amine group, or a C1-C4 aminoalkyl group.

[0011] The compound of chemical formula 1 may be present in an amount of 1 to 8% by weight, based on the total weight of the stepwise hair color composition.

[0012] The binder may be a (co)polymer containing vinyl alcohol as a monomer.

[0013] The compound of chemical formula 1 and the binder may be present in a weight ratio of 50:1 to 1:1.

[0014] The colloidal particles may have an average diameter (D50) of 200 to 500 nm.

[0015] The aforementioned stepwise hair color composition may further contain one or more polyphenols selected from the group consisting of gallic acid, tannic acid, catechin, caffeic acid, cyanidin, anthocyanidin, cyanidin-3-glucoside, and cyanidin-3-rutinoside.

[0016] The compound of chemical formula 1 and the polyphenol may be present in a weight ratio of 40:1 to 1:1.

[0017] A cosmetic composition according to another aspect of the present invention includes a stepwise hair color composition according to one aspect described above.

[0018] The cosmetic composition may include one or more selected from the group consisting of hair shampoo, hair rinse, hair dye pen, hair tonic, hair conditioner, hair essence, hair lotion, hair treatment, hair cream, hair wax, hair pack, hair oil, hair drying agent, hair preservation agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair gloss, hair lacquer, hair moisturizer, hair mousse, and hair spray.

[0019] The compound of chemical formula 1 may be present in an amount of 0.01 to 2% by weight, based on the total weight of the cosmetic composition. [Effects of the Invention]

[0020] The stepwise hair color composition according to the present invention and the cosmetic composition containing the same can dye hair without damaging the hair and causing allergic reactions on the scalp, and can prevent phase separation and formation of precipitates of the stepwise hair color composition by forming colloidal particles, showing excellent storage stability.

[0021] In addition, the cosmetic composition according to the present invention can be formulated into a hair shampoo or the like, and can show excellent dyeability when repeatedly treated on hair.

Brief Description of the Drawings

[0022] [Figure 1] (a) is an image of the stepwise hair color compositions of Examples 1 and 2 and Comparative Examples 1 to 3, and (b) is an image after storing the composition for one week. [Figure 2] (a) is the UV-vis spectrum of the stepwise hair color compositions of Examples 1 and 2 and Comparative Example 1 before oxidation, and (b) is the UV-vis spectrum after oxidation. [Figure 3] (a) is the FT-IR spectrum according to the temperature of the stepwise hair color compositions of Examples 2 and 3 before oxidation, and (b) is the UV-vis spectrum according to the temperature before oxidation. [Figure 4] Images after treating the bleached hair sample once with the hair shampoo composition, once with the hair conditioner composition, and once with the hair conditioner after once treating with the hair shampoo.

Modes for Carrying Out the Invention

[0023] Hereinafter, each configuration of the present invention will be described in more detail so that those having ordinary knowledge in the technical field to which the present invention pertains can easily implement it. However, this is merely an example, and the scope of the rights of the present invention is not limited by the following content. [[ID=,33]]

[0024] As used herein, the term “including” is used to list materials, compositions, apparatus, and methods useful to the present invention, and is not limited to such listed examples.

[0025] In this invention, "hair" refers to thread-like structures that protrude from the surface of the skin, encompassing both body hair and scalp hair.

[0026] In the present invention, "DPC (Dark Polyphenol Complex)" means a stepwise hair color composition containing the compound of the following chemical formula 1 and a binder, preferably a stepwise hair color composition containing the compound of the following chemical formula 1, a binder and a polyphenol.

[0027] A stepwise hair color composition according to one specific example of the present invention comprises colloidal particles containing a compound of the following chemical formula 1 and a binder, and the stepwise hair color composition can develop color upon contact with oxygen.

[0028] [ka]

[0029] During the ceremony, R1 is hydrogen, a hydroxyl group, or a carboxyl group. R2 and R3 are independent of each other: hydrogen, carboxyl group, C1-C 10 Alkyl alkyl group, C1-C 10 Haloalkyl groups, C1-C 10 Alkoxy group, C1-C 10 It is a haloalkoxy group, an amine group, or a C1-C4 aminoalkyl group.

[0030] Specifically, in the above chemical formula 1, R1 may be hydrogen or a hydroxyl group, and R2 and R3 may be hydrogen, a carboxyl group, or an amine group independently of each other. Preferably, R1 may be hydrogen or a hydroxyl group, and R2 and R3 may be hydrogen.

[0031] The stepwise hair color composition can include a solvent and the colloidal particles. The compound of Chemical Formula 1 and the binder can form a complex through intermolecular interaction, and at least a part of the complex can be dissolved in the solvent, and the rest can exist in the form of the colloidal particles. The colloidal particles can be oxidized upon contact with oxygen to develop color and can impart a dyeing effect when applied to hair.

[0032] Based on the total weight of the stepwise hair color composition, the compound of Chemical Formula 1 may be contained at 1% to 8% by weight. Specifically, the compound of Chemical Formula 1 may be contained at a content of 2% to 7% by weight, 3% to 6% by weight, or 4% to 5% by weight. Preferably, the compound of Chemical Formula 1 may be contained at 4% to 6% by weight. A composition with a content of the compound of Chemical Formula 1 less than 1% by weight cannot exhibit a dyeing effect on hair, and if it exceeds 8% by weight, precipitation occurs during storage of the composition, and the composition with precipitation has a reduced dyeing effect on hair.

[0033] The binder can form a complex with the compound of Chemical Formula 1 through intermolecular interaction. The binder may be one that forms a hydrogen bond with the compound of Chemical Formula 1. Specifically, the binder may be a polymer or copolymer containing vinyl alcohol as a monomer. For example, the binder may be one or more selected from the group consisting of PEG-136 polyvinyl alcohol, Elvanol TM ) and other polyvinyl alcohols; and copolymers of vinyl alcohol and glyoxal. Preferably, the binder may be polyvinyl alcohol. The binder increases the solubility of the compound of Chemical Formula 1, forms a complex with the compound of Chemical Formula 1, and can develop color upon contact with oxygen.

[0034] The compound of chemical formula 1 and the binder may be present in a weight ratio of 50:1 to 1:1. Specifically, the compound of chemical formula 1 and the binder may be present in a weight ratio of 45:1, 40:1, 35:1, 30:1, 25:1, 20:1, 15:1, 10:1, or 5:1. Preferably, the compound of chemical formula 1 and the binder may be present in a weight ratio of 20:1 to 3:1. The binder may be present in excess of the compound of chemical formula 1 by weight, forming a complex surrounding the compound of chemical formula 1. If the ratio is less than 50:1, precipitation will occur during storage of the composition, and compositions in which precipitation occurs will have a reduced dyeing effect on hair, while compositions with a ratio exceeding 1:1 will not exhibit a dyeing effect on hair.

[0035] The colloidal particles may be formed by stirring a mixture of the compound of chemical formula 1 and a binder, or additionally, polyphenols, in a solvent. In this case, the presence or absence of colloidal particle formation can be determined by the stirring temperature of the mixture. The stirring temperature of the mixture may be 25°C or higher and 75°C or lower. Specifically, the stirring temperature of the mixture may be 30°C or higher and 60°C or lower, 35°C or higher and 55°C or lower, or 40°C or higher and 50°C or lower. Preferably, the stirring temperature of the mixture may be 40°C or higher and 70°C or lower. If the stirring temperature of the mixture is below 25°C, colloidal particles will not be formed, and if it exceeds 75°C, the average diameter of the colloidal particles will exceed the range described below, causing precipitation in the composition.

[0036] The colloidal particles may have an average diameter (D50) of 200 to 500 nm. Specifically, the average diameter of the colloidal particles may be 250 nm or more and 450 nm or less, or 300 nm or more and 400 nm or less. Preferably, the average diameter of the colloidal particles may be 200 nm or more and 450 nm or less. When the content of the compound of chemical formula 1 and the weight ratio of the compound to the binder described above are satisfied, the average diameter of the colloidal particles may be 200 nm or more, and if the average diameter of the colloidal particles exceeds 500 nm, precipitation will occur during storage of the composition.

[0037] The aforementioned stepwise hair color composition may, but is not limited to, contain water as a solvent. For example, the solvent may be distilled water, ethanol, a pH buffer solution, a shampoo base, or any other solvent that does not cause damage upon contact with skin or hair and can be used in cosmetic compositions.

[0038] Another specific example of the present invention provides a stepwise hair color composition which may include colloidal particles comprising the compound of chemical formula 1 and a binder, and polyphenols. The colloidal particles may comprise the compound of chemical formula 1 and a binder, or may comprise the compound of chemical formula 1, a binder, and polyphenols.

[0039] The polyphenol may be capable of intermolecular interaction with the complex consisting of the compound of chemical formula 1 and the binder, or it may bind to at least a portion of the surface of the complex to increase the solubility of the compound of chemical formula 1, thereby improving the dyeing effect of the composition on hair. For example, the polyphenol may form hydrogen bonds with the compound of chemical formula 1 and the hydrogen or hydroxyl groups contained in the binder via hydrogen or hydroxyl groups.

[0040] The aforementioned polyphenol may include one or more selected from the group consisting of gallic acid, tannic acid, catechin, caffeic acid, cyanidin, anthocyanidin, cyanidin-3-glucoside, and cyanidin-3-rutinoside. For example, the term "anthocyanidin" can encompass derivatives such as aurantinidin, capensinidin, delphinidin, europhinidin, hirsutidin, malvidin, pelargonidin, peonidin, petunidin, pulchelidin, and rosinidin.

[0041] The compound of chemical formula 1 and the polyphenol may be present in a weight ratio of 40:1 to 1:1. Specifically, the compound of chemical formula 1 and the polyphenol may be present in a weight ratio of 35:1, 30:1, 25:1, 20:1, 15:1, 10:1, or 5:1. Preferably, the compound of chemical formula 1 and the polyphenol may be present in a weight ratio of 10:1 to 3:1. When the content ratio of the compound of chemical formula 1 and the polyphenol is adjusted to the above range, the polyphenol can improve the dispersibility of the compound of chemical formula 1 and provide a viscosity suitable for a graded hair color composition or cosmetic composition.

[0042] The aforementioned stepwise hair color composition can develop color upon exposure to air or oxygen for 1 to 60 minutes, preferably 1 to 30 minutes, and most preferably 1 to 3 minutes. Therefore, the aforementioned stepwise hair color composition uses oxygen in the air, which is harmless to the human body, as an oxidizing agent, does not require an oxidizing agent such as hydrogen peroxide, and can color hair without damaging the hair or irritating the scalp caused by hydrogen peroxide.

[0043] Another specific example of the present invention relates to a cosmetic composition comprising a stepwise hair color composition according to the above example. The cosmetic composition may comprise DPC and a functional cosmetic composition for application to hair or scalp, and the hair cosmetic composition may include one or more selected from the group consisting of hair shampoo, hair rinse, color pen, hair tonic, hair conditioner, hair essence, hair lotion, hair treatment, hair cream, hair wax, hair pack, hair oil, hair drying agent, hair preservation treatment agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair gloss, hair lacquer, hair moisturizer, hair mousse, and hair spray.

[0044] The term "cosmetic composition" can also encompass a first agent in any one dosage form and a second agent in a dosage form different from the first agent. Specifically, the first and second agents may each be a stepped hair color composition containing the colloidal particles. For example, the first agent, a stepped hair color composition, may be a hair shampoo, and the second agent, a stepped hair color composition, may be a hair conditioner. In this case, the second agent, a hair conditioner, may be used after the first agent to boost the color development effect of the first agent.

[0045] The cosmetic composition may be such that when the first and second components are mixed, they constitute a single dosage form. Specifically, the first component may be a stepped hair color composition containing the colloidal particles, and the second component may be a polyphenol solution. For example, the first component, which is the stepped hair color composition, may be an aqueous solution of the colloidal particles, and the second component may be a shampoo base to which polyphenols have been added. In this case, the first and second components may be mixed when the cosmetic composition is used, and the color development effect of the first component can be enhanced.

[0046] The cosmetic composition may be a mixture of a stepwise hair color composition and a composition in the dosage form of the cosmetic composition. For example, the cosmetic composition may be a single-dosage hair shampoo composition, or the cosmetic composition may be a mixture of a stepwise hair color composition and a shampoo base composition. Alternatively, the cosmetic composition may be a single-dosage hair conditioner composition, or the cosmetic composition may be a mixture of a stepwise hair color composition and a hair conditioner base composition.

[0047] Specifically, if the cosmetic composition is a hair shampoo composition, the shampoo base composition may include edelweiss callus extract, purified water, and sodium C. 14-16 It may contain olefin sulfonate, disodium laureth sulfosuccinate, glycerin, sorbitol, sodium cocoyl isethionate, cocamidopropyl hydroxysultaine, lauryl glucoside, 1,2-hexanediol, PPG-3-caprylyl ether, sodium chloride, guar hydroxypropyltrimonium chloride, panthenol, polyquaternium-10, ethylhexylglycerin, caprylyl glycol, menthol, caramel, citric acid, and salicylic acid.

[0048] Specifically, if the cosmetic composition is a hair conditioner composition, the hair conditioner base composition may include purified water, glycerin, cetearyl alcohol, isopropyl myristate, behentrimonium chloride, mineral oil, stearyl alcohol, jojoba oil, cetrimonium chloride, amodimethicone, isopropyl alcohol, hydroxyethylcellulose, guar hydroxypropyltrimonium chloride, isopropyl palmitate, arachidyl alcohol, cetyl alcohol, trideceth-12, citric acid, and sodium benzoate. Based on the total weight of the cosmetic composition, the compound of chemical formula 1 may be present in an amount of 0.01 to 2% by weight. Specifically, the compound of chemical formula 1 may be present in an amount of 0.1% to 1.5% by weight, or 1% to 2% by weight. Preferably, the compound of chemical formula 1 may be present in an amount of 0.1% to 0.7% by weight. Cosmetic compositions containing less than 0.01% by weight of the compound of chemical formula 1 cannot exhibit a dyeing effect on hair, and if the content exceeds 2% by weight, precipitation occurs during storage of the composition, and the composition in which precipitation occurs has a reduced dyeing effect on hair.

[0049] Another specific example of the present invention relates to a method for dyeing hair, comprising the step of bringing a stepwise hair color composition according to the above specific example into contact with hair. The step of bringing a stepwise hair color composition into contact with hair may also be the step of bringing a cosmetic composition containing the stepwise hair color composition into contact with hair. The step may involve immersing or supporting the hair in the composition, applying the composition to the hair using hands or other tools such as a comb, or pouring the composition onto the hair or spraying it using a sprayer, etc., but is not limited thereto.

[0050] The hair dyeing method may further include a step of drying the hair that has come into contact with the stepwise hair color composition in the air. This step may involve leaving the hair in the air for 1 to 60 minutes, or drying it with a hairdryer for 1 to 5 minutes, but is not limited to these steps. Next, the hair dyeing method may further include a step of washing away any remaining stepwise hair color composition from the hair with water after the hair has been dyed. Preferably, the hair dyeing method may involve repeating the steps of contacting the hair with the composition and drying the hair in the air at predetermined time intervals. In this case, the hair treated with the composition can maintain a more pronounced color for a longer period of time.

[0051] The present invention will be described in more detail below through specific examples and experimental cases. The following examples and experimental cases are for illustrative purposes only and do not limit the present invention to the following examples and experimental cases.

[0052] Examples 1-3 and Comparative Examples 1-3 As the compound of chemical formula 1, commercially available 2,2',4,4',5,5'-hexahydroxybiphenyl (HDP) was used.

[0053] In Examples 1 and 2 and Comparative Examples 1 to 3, 3 mL of distilled water was added to a reaction vessel exposed to nitrogen, and HDP, a binder, or gallic acid as a polyphenol as shown in Table 1 below (unit: g). The mixture was then stirred at 50°C and 100-300 rpm for 10 minutes to produce stepwise hair color compositions.

[0054] In Example 3, a stepwise hair color composition was prepared in the same manner as in Example 1, except that the mixture was stirred at 25°C after adding the contents shown in Table 1 below.

[0055] [Table 1]

[0056] Examples 4-6 and Comparative Examples 4-17 In Examples 4 and 5 and Comparative Examples 5 to 17, 3 mL of distilled water was added to a reaction vessel exposed to nitrogen, and the compound of chemical formula 1 shown in Table 2 below, a binder (polyvinyl alcohol), or gallic acid as a polyphenol, or a mixture of gallic acid, tannic acid, and catechin was added (in units: g). The mixture was then stirred at 50°C and 100-300 rpm for 10 minutes to produce a stepwise hair color composition.

[0057] Thereafter, the above composition is used as a shampoo base and contains 42.5g of edelweiss callus extract, 30g of purified water, and sodium C 14-16 6g of olefin sulfonate, 8g of disodium laureth sulfosuccinate, 1.5g of glycerin, 1.2g of sorbitol, 2g of sodium cocoyl isethionate, 1.8g of cocamidopropyl hydroxysultaine, 1.15g of lauryl glucoside, 1.05g of 1,2-hexanediol, 0.8g of PPG-3-caprylyl ether, 0.1g of niacinamide, 0.5g of sodium chloride, 0.45g of guar hydroxypropyltrimonium chloride, 0.2g of panthenol, 0.2g of polyquaternium-10, 0.1g of ethylhexylglycerin, 0.1g of caprylyl glycol, 0.05g of menthol, 0.3g of caramel, 0.03g of citric acid, and 0.2g of salicylic acid were further added, and the mixture was stirred at 50°C and 50-100 rpm for 5 minutes to produce a hair shampoo composition.

[0058] In Example 6, a hair shampoo composition was produced in the same manner as in Example 4, except that after adding the contents shown in Table 2 below, the mixture was stirred at 25°C to produce a stepwise hair color composition, and the shampoo base was further mixed and stirred at 25°C to produce a hair shampoo composition.

[0059] Comparative Example 4 involved preparing a hair shampoo composition in the same manner as in Example 4, except that THB (1,2,4-trihydroxybenzene) was used instead of the compound of chemical formula 1.

[0060] [Table 2]

[0061] Examples 7-13 Examples 7-13 used compounds in which R1-R3 in the following chemical formula 1 are listed in Table 3 below.

[0062] [ka]

[0063] [Table 3]

[0064] In Examples 7-13, hair shampoo compositions were produced in the same manner as in Example 4, except that 3 mL of distilled water was added to a reaction vessel exposed to nitrogen, and the contents shown in Table 4 below were added (in units: g).

[0065] [Table 4]

[0066] Examples 14-16 and Comparative Example 18 In Examples 14-15 and Comparative Example 18, 3 mL of distilled water was added to a reaction vessel exposed to nitrogen, and HDP, a binder (polyvinyl alcohol), or gallic acid as a polyphenol, or a mixture of gallic acid, tannic acid, and catechin (unit: g) as shown in Table 5 below was added, and the mixture was stirred at 50°C and 100-300 rpm for 10 minutes to produce a stepwise hair color composition.

[0067] Subsequently, the following were added to the aforementioned composition as a conditioner base: 76g purified water, 6g glycerin, 5g cetearyl alcohol, 3.5g isopropyl myristate, 2g behentrimonium chloride, 1.5g mineral oil, 1.25g stearyl alcohol, 1g jojoba oil, 1g cetrimonium chloride, 0.8g amodimethicone, 0.5g isopropyl alcohol, 0.33g hydroxyethylcellulose, 0.2g guar hydroxypropyltrimonium chloride, 0.18g isopropyl palmitate, 0.15g arachidyl alcohol, 0.125g cetyl alcohol, 0.15g trideceth-12, 0.12g citric acid, and 0.1g sodium benzoate. The mixture was then stirred at 50°C and 50-100 rpm for 5 minutes to produce a hair conditioner composition.

[0068] In Example 16, a hair conditioner composition was produced in the same manner as in Example 14, except that after adding the contents shown in Table 5 below, a stepwise hair color composition was produced by stirring at 25°C and 100-300 rpm for 10 minutes, and then the conditioner base was further mixed and stirred at 25°C to produce a hair conditioner composition.

[0069] [Table 5]

[0070] Experimental Example 1. Confirmation of the stability of a stepwise hair color composition. The stepwise hair color compositions prepared in Examples 1 and 2 and Comparative Examples 1 to 3 were injected into test tubes in 1 mL increments, sealed, and stored at room temperature for one week while the stability of each composition was visually confirmed. Figure 1(a) shows the stepwise hair color composition immediately after preparation, and Figure 1(b) shows the stepwise hair color composition after one week of storage.

[0071] Referring to Figure 1, in the compositions of Comparative Examples 1-3, the HDP was not well dispersed, and the HDP particles precipitated over time.

[0072] Experimental Example 2. Confirmation of structural changes due to oxidation of stepwise color compositions. The compositions of Examples 1 and 2 and Comparative Example 1 were exposed to air and stored for 24 hours to oxidize. The absorbance of the compositions before and after oxidation was checked using UV-vis (Ubi-490, Micro Digital) to confirm whether or not there was any structural change due to oxidation. Figure 2(a) shows the UV-vis spectrum of each composition before oxidation, and Figure 2(b) shows the UV-vis spectrum after oxidation.

[0073] Referring to Figure 2, in the example composition, the absorbance increased at a wavelength of 280 nm after oxidation, and considering the hair experiment described later, it was confirmed that the oxidation of the composition resulted in a dyeing effect on hair.

[0074] Experimental Example 3. Structural Analysis of Hair Color Compositions in Steps Based on Manufacturing Temperature The stepwise hair color compositions prepared in Examples 2 (manufacturing temperature 50°C) and 3 (manufacturing temperature 25°C) were structurally analyzed using FT-IR (Madison, Thermo Scientific) and UV-vis. Figure 3(a) shows the FT-IR spectra of each composition, and Figure 3(b) shows the UV-vis spectra of each composition in a sealed state after manufacturing.

[0075] As can be seen in Figure 3(a), it is clear that the -OH bond moves with increasing manufacturing temperature, and it was confirmed that increasing the manufacturing temperature increases the hydrogen bonding force, making it easier to form colloidal particles.

[0076] Referring to Figure 3(b), we confirmed that increasing the manufacturing temperature increased the hydrogen bonding force, leading to an increase in solubility and an increase in absorbance.

[0077] The size of colloidal particles contained in the stepwise hair color compositions prepared according to Examples 2 and 3 was confirmed by dynamic light scattering (Dynamic Light Scattering Spectrometer, Zetasizer Nano, Malvern (concentration: 0.01 mg / mL)). Two days after the preparation of each composition, the average diameter (D50, unit: nm) of the colloidal particles contained in each composition was measured and is shown in Table 6 below.

[0078] [Table 6]

[0079] Experimental Example 4. Evaluation of the dyeing properties of hair shampoo compositions based on the binder content. The hair shampoo compositions prepared in Example 4 and Comparative Examples 6-9 were used to evaluate their ability to dye hair.

[0080] Each decolorized hair sample was shampooed with the hair shampoo composition according to Example 4 and Comparative Examples 6-9, and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo composition were calculated using a colorimeter and are shown in Table 7 below.

[0081] [Table 7]

[0082] In Comparative Example 6, the high binder content resulted in the blockage of the compound of chemical formula 1 by the binder, slowing down the rate of color change due to oxidation and reducing the color development power. In Comparative Examples 7-9, the low binder content resulted in reduced color development power due to decreased dispersibility of the colloidal particles.

[0083] Experimental Example 5. Evaluation of the dyeing properties of hair shampoo compositions based on the content of the compound of chemical formula 1. The hair shampoo compositions prepared in Example 4 and Comparative Examples 10-13 were used to evaluate their ability to dye hair.

[0084] Each decolorized hair sample was shampooed with the hair shampoo compositions of Example 4 and Comparative Examples 10-13 and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo compositions were calculated using a colorimeter and are shown in Table 8 below.

[0085] [Table 8]

[0086] Comparative Examples 10 and 11 showed that the low content of the compound of chemical formula 1, based on the total weight of the graded hair color composition, resulted in reduced color development. Comparative Examples 12 and 13 showed that the high content of the compound led to reduced dispersibility, with precipitate visible to the naked eye after 7 days, and the color development was lower compared to Example 4.

[0087] Experimental Example 6. Evaluation of the dyeing properties of hair shampoo compositions based on polyphenol content. The hair shampoo compositions prepared in Example 4 and Comparative Examples 14-17 were used to evaluate their ability to dye hair.

[0088] Each decolorized hair sample was shampooed with the hair shampoo composition prepared in Example 4 and Comparative Examples 14-17, and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo composition were calculated using a colorimeter and are shown in Table 9 below.

[0089] [Table 9]

[0090] Comparative Examples 16 and 17 showed that the low polyphenol content resulted in reduced color development due to decreased dispersibility of colloidal particles. Comparative Examples 14 and 15 showed that the high polyphenol content led to increased bonding between colloidal particles, resulting in precipitation, which was visually confirmed, and a decrease in color development was also observed.

[0091] Experimental Example 7. Evaluation of the dyeing properties of hair shampoo compositions based on the type of compound of chemical formula 1. The hair shampoo compositions prepared in Examples 4 and 7-13 were used to evaluate their ability to dye hair.

[0092] Each decolorized hair sample was shampooed with the hair shampoo composition according to Examples 4 and 7-13 and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo composition were calculated using a colorimeter and are shown in Table 10 below.

[0093] [ka]

[0094] [Table 10]

[0095] Experimental Example 8. Evaluation of the dyeability of hair shampoo compositions based on the presence or absence of binders, polyphenol composition, and manufacturing temperature. The hair shampoo compositions prepared in Examples 4 and 5 and Comparative Example 5 were used to evaluate their ability to dye hair.

[0096] Each decolorized hair sample was shampooed with the hair shampoo compositions of Examples 4, 5, and Comparative Example 5, and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo compositions were calculated using a colorimeter and are shown in Table 11 below.

[0097] [Table 11]

[0098] The hair shampoo compositions prepared in Examples 5 and 6 were used to evaluate their ability to dye hair.

[0099] Each decolorized hair sample was shampooed with the hair shampoo composition according to Examples 5 and 6 and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair shampoo composition were calculated using a colorimeter and are shown in Table 12 below.

[0100] [Table 12]

[0101] Referring to Tables 11 and 12, it was confirmed that, even considering the errors from repeated experiments, the hair shampoo composition of Example 5, prepared using a binder, three combinations of polyphenols, and a manufacturing temperature of 50°C, exhibited the best color development ability.

[0102] Experimental Example 9. Evaluation of the dyeability of hair conditioner compositions based on the presence or absence of binders, polyphenol composition, and manufacturing temperature. The hair conditioner compositions prepared in Examples 14 and 15 and Comparative Example 18 were used to evaluate their ability to dye hair.

[0103] Each bleached hair sample was treated with the hair conditioner composition according to Examples 14, 15, and Comparative Example 18, and then dried. The color difference values ​​(ΔL*) of the hair samples before and after treatment with the hair conditioner composition were calculated using a colorimeter and are shown in Table 13 below.

[0104] [Table 13]

[0105] The hair conditioner compositions prepared in Examples 15 and 16 were used to evaluate their ability to dye hair.

[0106] Each decolorized hair sample was shampooed and dried using the hair conditioner compositions from Examples 15 and 16. The color difference values ​​(ΔL*) before and after treatment with the hair conditioner compositions were calculated using a colorimeter for each hair sample and are shown in Table 14 below.

[0107] [Table 14]

[0108] Referring to Tables 13 and 14, it was confirmed that, even considering the errors from repeated experiments, the hair conditioner composition of Example 15, prepared using a binder, three combinations of polyphenols, and a manufacturing temperature of 50°C, exhibited the best color development ability.

[0109] Experimental Example 10. Evaluation of dyeing properties by stepwise use of hair shampoo and hair conditioner compositions. The hair shampoo compositions from Examples 4, 5 and Comparative Example 5, and the hair conditioner compositions from Examples 14, 15 and Comparative Example 18 were used to evaluate their ability to dye hair.

[0110] Decolorized hair samples were prepared, and each sample was treated once with a hair shampoo composition and dried; once with a hair conditioner composition and dried; or once with a hair shampoo composition, dried, and then once with a hair conditioner composition and dried. Figure 4 shows the staining results of each hair sample according to the treatment method, and the color difference value (ΔL*) for each sample is shown in Table 15 below.

[0111] [Table 15]

[0112] Experimental Example 11. Evaluation of the repeatability of hair shampoo compositions. The hair shampoo compositions from Examples 4 and 5 and Comparative Example 5 were repeatedly applied, and their ability to dye hair was evaluated.

[0113] Decolorized hair samples were prepared, and each sample was treated with a hair shampoo composition once and dried, or the treatment and drying process was repeated five times. The color difference value (ΔL*) for each hair sample according to the treatment method, along with the degree of improvement in dyeing, is shown in Table 16 below.

[0114] Specifically, "1-time ΔL*" is the color difference value of the hair shampoo composition before and after one treatment, "5-time ΔL*" is the color difference value of the hair shampoo composition after five treatments compared to one treatment, and "ΔΔL*" (unit: %) represents the degree of improvement in dyeing, which was calculated as follows.

[0115] ΔΔL*={(5 times ΔL*)-(1 time ΔL*)} / (1 time ΔL*)×100

[0116] [Table 16]

[0117] As shown in Table 16, the hair shampoo compositions used in the examples showed rich color development despite only a few repeated treatments (approximately 5 times), and were found to be superior to the comparative examples in terms of the degree of improvement in dyeing with repeated treatments.

Claims

1. A stepwise hair color composition containing colloidal particles, The colloidal particles comprise the compound of the following chemical formula 1 and a binder. The aforementioned stepwise hair color composition develops color upon contact with oxygen: 【Chemistry 1】 During the ceremony, R 1 is hydrogen, a hydroxyl group, or a carboxyl group, R 2 and R 3 are each independently hydrogen, a carboxy group, C 1 -C 10 alkyl group, C 1 -C 10 haloalkyl group, C 1 -C 10 alkoxy group, C 1 -C 10 haloalkoxy group, an amine group, or C 1 -C 4 aminoalkyl group.

2. The compound of chemical formula 1 is The stepwise hair color composition according to claim 1, wherein it is contained in an amount of 1 to 8% by weight based on the total weight of the stepwise hair color composition.

3. The aforementioned binder is The stepwise hair color composition according to claim 1, which is a (co)polymer containing vinyl alcohol as a monomer.

4. The stepwise hair color composition according to claim 1, wherein the compound of chemical formula 1 and the binder are contained in a weight ratio of 50:1 to 1:

1.

5. The stepwise hair color composition according to claim 1, wherein the colloidal particles have an average diameter (D50) of 200 to 500 nm.

6. The stepwise hair color composition according to claim 1, further comprising one or more polyphenols selected from the group consisting of gallic acid, tannic acid, catechin, caffeic acid, cyanidin, anthocyanidin, cyanidin-3-glucoside, and cyanidin-3-rutinoside.

7. The stepwise hair color composition according to claim 6, wherein the compound of chemical formula 1 and the polyphenol are contained in a weight ratio of 40:1 to 1:

1.

8. A cosmetic composition comprising the stepwise hair color composition according to any one of claims 1 to 7.

9. The cosmetic composition according to claim 8, wherein the cosmetic composition is in the form of a hair shampoo, hair rinse, dye pen, hair tonic, hair conditioner, hair essence, hair lotion, hair treatment, hair cream, hair wax, hair pack, hair oil, hair drying agent, hair preservation agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair gloss, hair lacquer, hair moisturizer, hair mousse, or hair spray.

10. The compound of chemical formula 1 is The cosmetic composition according to claim 8, wherein it is contained in an amount of 0.01 to 2% by weight based on the total weight of the cosmetic composition.

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