Composition for dyeing hair

Abstract

The present invention provides a composition for dyeing hair, the composition comprising: a polyphenolic compound; and at least one selected from the group consisting of an acid addition salt of a 5,6-dihydroxyindoline-based compound of chemical formula 1, a 5,6-dihydroxyindole-based compound of chemical formula 2, and a polydihydroxyindole compound of chemical formula 3. The present invention can be used in dyeing shampoos, hair dyes (dyeing agents), etc.

Description

Composition for hair dyeing

[0001] The present invention relates to a composition for hair dyeing, and more specifically, to a composition that can be used in a hair dyeing shampoo, hair dye (dye agent), etc.

[0002] Hair dyes are classified into permanent hair dyes, semi-permanent hair dyes, and temporary hair dyes depending on the color retention after dyeing, oxidizing hair dyes and non-oxidizing hair dyes depending on whether or not the dye undergoes oxidation, and single-component (single-component) hair dyes and two-component (mixed-component) hair dyes depending on whether or not the ingredients are mixed during dyeing.

[0003] Temporary hair dyes use a film-forming agent (coating agent) to temporarily attach pigments (tar pigments) or other substances to the cuticle, the outermost layer of the hair, so their principle is different from that of regular hair dyes.

[0004] Semi-permanent hair dyes are generally non-oxidizing dyes, such as acidic or basic dyes. These dyes, which possess their own color without the need for oxidative polymerization, attach to the hair through ionic bonds with amino acids in the hair, resulting in dyeing. The dyes in semi-permanent hair dyes are generally large and do not penetrate the hair cortex (codex) layer well, resulting in shorter dyeing durations compared to permanent hair dyes.

[0005] Permanent hair dyes are generally oxidative hair dyes, which are two-component (mixed) hair dyes consisting of a first component and a second component. The first component contains a dye precursor and an alkaline agent (usually ammonia) to help the dye precursor penetrate well into the cortex (codex). The second component contains an oxidizing agent such as hydrogen peroxide to break down the melanin in the hair and promote the oxidation reaction of the dye precursor in the first component. These oxidative hair dyes are used as general hair dyes because they have excellent color retention, a rich color tone, and the ability to dye in a preferred color tone. p-Phenylenediamine (PPD) is the most commonly used dye intermediate (precursor) in oxidative hair dyes. These oxidative hair dyes have a relatively long reaction time between the first and second components and high hair penetration, so they stain skin such as hands and nails severely. Therefore, careful dyeing is required using a comb or brush to avoid contact with the skin. In addition, if the dye stains the skin, it is difficult to erase. In addition, oxidizing hair dyes not only damage hair but can also cause allergic reactions, so special care must be taken when using them, and they also have the problem of producing a strong ammonia smell.

[0006] Recently, so-called "dye shampoos," which gradually darken gray or grey hair by simply washing it with shampoo, have emerged as an alternative to traditional hair dyes. These dye shampoos are applied by hand, so they should not stain the skin other than the hair. They should also be used for a shorter period of time (typically less than five minutes) than hair dyes.

[0007] Recently, a dyeing shampoo utilizing the browning phenomenon of polyphenol compounds is being developed. Polyphenol (polyphenol) compounds are a general term for phenol compounds with two or more hydroxyl groups bonded to a benzene ring. They are found in various plants, including soybeans, green tea, persimmons, blueberries, aronia, and onions. Polyphenol compounds range in molecular weight from relatively large substances, such as tannins, flavonoids, catechins, epicatechins, anthocyanins, and isoflavones, to relatively small substances, such as pyrogallol, catechol, gallic acid, and alkyl gallates. They are known to have antioxidant effects.

[0008] Plant browning refers to the brown or black discoloration that occurs when plants are injured. When plant cells are destroyed, polyphenol peroxidase within the cells is exposed to the air. This polyphenol peroxidase then reacts with oxygen in the air, triggering enzymatic activity. This oxidation of polyphenols leads to the production of pigments such as melamine. However, the oxidation of polyphenols by polyphenol peroxidase is not very fast, so hair dyeing utilizing this browning effect is minimal.

[0009] Korean Patent Publication No. 10-2021-0003404 discloses a hair dyeing composition comprising a mixture of tannic acid and gallic acid in a molar ratio of 1:0.1 to 1:50, a divalent iron salt, and water. The composition of the patent describes a process in which complex compound 1 (divalent iron salt) forms complex compound 2 (trivalent iron salt) upon contact with oxygen, which is then deposited on the hair and coated.

[0010] Korean Patent Publication No. 10-2023-0009144 discloses a hair dye composition containing trihydroxybenzene. The patent states that trihydroxybenzene, due to its adhesive / adsorbent properties to proteins, remains on the hair surface in trace amounts even after washing with water. The patent describes that when the trihydroxybenzene present on the hair surface comes into contact with oxygen, an oxidation reaction occurs, and as a result of this oxidation, the hair gradually develops a darker color. Among these, a shampoo containing 1,2,4-trihydroxybenzene (THB) is commercially available under the brand name "Modamoda™ Shampoo."

[0011] The Ministry of Food and Drug Safety (MFDS) of the Republic of Korea has placed 1,2,4-trihydroxybenzene (THB), a key ingredient in Modamoda™ products, on the banned list in 2022. The MFDS based its decision on an evaluation report from the European Scientific Committee on Consumer Safety (SCCS), which determined that THB is potentially toxic and raises concerns about skin sensitization (a symptom in which the skin becomes sensitive).

[0012] The purpose of the present invention is to provide a hair dyeing composition that can be used in a short period of time compared to conventional hair dyes, has excellent coloring power, and does not easily stain the skin, so that it can be effectively used as a hair dye (dyeing agent) as well as a hair dyeing shampoo.

[0013] The present invention provides a hair dyeing composition comprising a polyphenol compound; and at least one selected from the group consisting of an acid addition salt of a 5,6-dihydroxyindoline compound of the following chemical formula 1, an acid addition salt of a 5,6-dihydroxyindole compound of the following chemical formula 2, and a polydihydroxyindole of the following chemical formula 3.

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 2]

[0017]

[0018] [Chemical Formula 3]

[0019]

[0020] (In the above chemical formulas,

[0021] R 1 , R 3 , R 4 and R 5 are each independently H or C 1-4 It is alkyl,

[0022] R 2 is H, C 1-4 Alkyl or carboxyl,

[0023] X is greater than or equal to 2.)

[0024] In one aspect of the present invention, when the hair dyeing composition is a single-part composition, the pH value of the composition may be 5 to 8, preferably 6 to 7.

[0025] In one aspect of the present invention, when the hair dyeing composition is a two-component type, the first component contains the 5,6-dihydroxyindoline compound acid addition salt or the 5,6-dihydroxyindoline compound acid addition salt and has a pH value of 2 to 6, the second component has a pH value of 7 to 13, and the first or second component may contain a polyphenol compound.

[0026] In one aspect of the present invention, the 5,6-dihydroxyindoline compound of the chemical formula 1 may be 5,6-dihydroxyindoline or 5,6-dihydroxyindoline-2-carboxylic acid.

[0027] In one aspect of the present invention, the 5,6-dihydroxyindole compound of the above chemical formula 2 may be 5,6-dihydroxy-1H-indole-2-carboxylic acid.

[0028] In one aspect of the present invention, the acid addition salt may be at least one selected from the group consisting of hydrobromide, hydrochloride, sulfate, phosphate, acetate, propionate, lactate, and citrate.

[0029] In one aspect of the present invention, the polyphenol compound may be a plant-derived compound, a plant extract, or a synthetic compound.

[0030] In one aspect of the present invention, the polyphenol compound is gallic acid, C 1~10 Alkyl gallate, 2,3,4-Trihydroxybenzoic acid, syringic acid, protocatechic acid, vanillic acid, caffeic acid, tannin, catechin, catechin gallate, epicatechin, gallocatechin, gallocatechin gallate, epigallocatechin, epigallocatechin gallate, quercetin, kaempferol, rutin, myricetin, anthocyanin, anthocyanidin, It may be at least one selected from the group consisting of cyanidin, petudinin, malvidin, delphinidin, pelargonidin, curcumin, genistein, daidzein, naringenin, hesperitin, hesperidin, neohesperitin, baicalein, baicalin, naringin, apigenin, luteolin, chrysin, and resveratrol.

[0031] In one aspect of the present invention, the pH value of the first agent may be 3 to 4.

[0032] In one aspect of the present invention, the pH value of the second agent may be 7 to 9.

[0033] In one aspect of the present invention, the acid addition salt of the 5,6-dihydroxyindoline compound or the acid addition salt of the 5,6-dihydroxyindoline compound may be 0.1 to 10 wt% based on the total weight of the hair dyeing composition.

[0034] In one aspect of the present invention, the polyphenol compound may be present in an amount of 0.1 to 10 wt% based on the total weight of the hair dyeing composition.

[0035] In one aspect of the present invention, the hair dyeing composition may further include one or more selected from a surfactant, an antioxidant, a swelling agent, a buffer, a viscosity control agent, and a moisturizer.

[0036] In one aspect of the present invention, the hair dyeing composition may be formulated as a liquid, foam, cream, lotion, gel, spray or powder.

[0037] In one aspect of the present invention, the hair dyeing composition may be a hair dye, shampoo, hair foam, hair conditioner, hair treatment, hair spray, hair lotion, hair gel, hair cream or hair essence formulation, or may be included in the formulation.

[0038] The hair dyeing composition according to the present invention not only can be used in a short period of time compared to conventional oxidizing hair dyes, but also has excellent coloring power and does not easily stain the skin when dyeing hair, so it can be usefully used as a dyeing shampoo, and has the effect of enabling the implementation of various color tones.

[0039] In addition, since the hair dyeing composition according to the present invention is a two-part composition, it is stable to oxygen in the air, so there is no need to use an expensive special oxygen-blocking container, and thus it has excellent effects in terms of manufacturing cost and long-term storage stability.

[0040] Figure 1 shows the dyeing characteristics according to changes in pH concentration of a hair dyeing composition according to Example 1 (polyphenol: gallic acid. Reaction initiator: 5,6-dihydroxyindoline hydrobromide).

[0041] Figure 2 shows the dyeing characteristics of a single-component dyeing shampoo according to Example 2.

[0042] Figure 3 shows the dyeing characteristics of a two-component dyeing shampoo according to Example 3.

[0043] Figure 4 shows the dyeing characteristics of the two-component dyeing shampoos according to Examples 4 to 9.

[0044] Figure 5 shows the dyeing characteristics of a two-component dyeing shampoo according to Example 10 (polyphenol: polyphenol extract. Reaction initiator: 5,6-dihydroxyindoline).

[0045] Figure 6 shows the dyeing characteristics of a two-component dyeing shampoo according to Example 11 (polyphenol: propyl gallate. Reaction initiator: 5,6-dihydroxyindoline).

[0046] Figure 7 shows the dyeing characteristics according to the change in pH concentration of the hair dyeing composition according to Example 12 (polyphenol: gallic acid. Reaction initiator: 2-carboxyl-5,6-dihydroxyindoline hydrochloride).

[0047] Figure 8 shows the dyeing characteristics of the two-component dyeing shampoos according to Examples 13 to 18.

[0048] Figure 9 shows the dyeing characteristics according to the change in pH concentration of the hair dyeing composition according to Example 19 (polyphenol: gallic acid. Reaction initiator: 5,6-dihydroxy-1H-indole-2-carboxylic acid).

[0049] Figure 10 shows the dyeing characteristics of the two-component dyeing shampoos according to Examples 20 to 25.

[0050] Figure 11 shows the dyeing characteristics of a two-component dyeing shampoo according to Example 26 (reaction initiator: 5,6-dihydroxyindoline and polydihydroxyindole).

[0051] The present inventors studied hair dyeing ingredients that can activate the browning of polyphenols by replacing polyphenol peroxidase in order to develop a hair dyeing composition utilizing the browning of polyphenols, and as a result, confirmed that 5,6-dihydroxyindoline compounds, 5,6-dihydroxyindole compounds, and polydihydroxyindole compounds effectively activate the browning of polyphenols depending on the pH concentration, thereby completing the present invention.

[0052] Since 5,6-dihydroxyindole is known to be involved in the biosynthesis of eumelanin, there have been attempts to develop a hair dye using it. However, 5,6-dihydroxyindole is extremely unstable in both free and salt forms, and it is known that it cannot be used as a hair dye due to the unstable polymerization product (water-insoluble dye) that cannot be fixed (dyed) to hair in the presence of oxygen in the air and rapid color oxidation.

[0053] It has been reported that 5,6-dihydroxyindoline, an analog of 5,6-dihydroxyindole, can be used as an ingredient in hair dyes.

[0054] U.S. Patent No. 5,178,637, U.S. Patent No. 6,719,811, and International Patent Publication No. WO1991 / 017739 disclose oxidation-type hair dyes containing 5,6-dihydroxyindoline compounds as dye precursors. 5,6-dihydroxyindoline reacts with oxygen to form radicals, and these radicals chain react to form dyes such as melanin. The patents disclose that 5,6-dihydroxyindoline compounds alone can be used as dye precursors, and can be used as color modifiers that react with dye precursors of oxidation-type hair dyes, such as p-phenylenediamine, p-tolylenediamine, and 2-chloro-p-phenylenediamine. Additionally, the above patent describes that hydrogen peroxide, ammonium peroxide disulfate, potassium peroxide disulfate, water-soluble iodine peroxide salts, etc. can be used as oxidizing agents for 5,6-dihydroxyindoline compounds.

[0055] Meanwhile, European Patent Publication No. EP 1254650A1 relates to a hair dye using a 5,6-dihydroxyindoline compound as a dye precursor, and to solve the problem of hair turning reddish when ammonia is used as an alkaline agent, H2N-CH2-R (wherein R is H, substituted or unsubstituted C) is used instead of ammonia. 1-5 The patent discloses a single-component hair dyeing composition using an amine compound represented by an alkyl or phenyl group and having a pH of 8.5 to 11 (preferably 9 to 10.5). The patent describes that the composition may include an antioxidant such as sodium sulfite, ascorbic acid, thioglycolic acid, L-cysteine, or N-acetyl-L-cysteine ​​to prevent the dyeing ability from being weakened due to oxidation of the 5,6-dihydroxyindoline compound over time.

[0056] The present inventors confirmed that in acid addition salt solutions of 5,6-dihydroxyindoline and 5,6-dihydroxyindoline-2-carboxylic acid, these compounds do not react with oxygen in the salt form, but react with oxygen in the free form to produce a dye. The acid addition salt solution of these compounds has a higher content of the free form as the pH concentration increases, and a dye is produced through reaction with oxygen. In particular, at a basic pH of 8 or higher, the oxygen reaction is fast, so that the discoloration of the skin (hands and nails) is very severe. Therefore, it can be used as an oxidation-type hair dye, but it is not suitable as a dyeing shampoo that requires hand use. In addition, it was confirmed that at pH 5 or higher, an insoluble dye is produced when reacting with oxygen in the air upon long-term storage.

[0057] Accordingly, the inventors of the present invention confirmed that when a polyphenol compound and a 5,6-dihydroxyindoline compound were mixed with each other as dye active ingredients, the dyeing characteristics and storage stability greatly changed depending on pH.

[0058] The hair dyeing composition according to the present invention comprises, as a dye active ingredient, a polyphenol-based compound and at least one selected from the group consisting of an acid addition salt of a 5,6-dihydroxyindoline-based compound of the following chemical formula 1, a 5,6-dihydroxyindoline-based compound of the following chemical formula 2, and a polydihydroxyindole compound of the following chemical formula 3.

[0059] [Chemical Formula 1]

[0060]

[0061] [Chemical Formula 2]

[0062]

[0063] [Chemical Formula 3]

[0064]

[0065] (In the above chemical formulas,

[0066] R 1 , R3 , R 4 and R 5 are each independently H or C 1-4 It is alkyl,

[0067] R 2 is H, C 1-4 Alkyl or carboxyl,

[0068] X is greater than or equal to 2.)

[0069] In one aspect of the present invention, the 5,6-dihydroxyindoline compound of the chemical formula 1 may be 5,6-dihydroxyindoline of the following chemical formula 4 or 5,6-dihydroxyindoline-2-carboxylic acid of the following chemical formula 5.

[0070] [Chemical Formula 4]

[0071]

[0072] [Chemical Formula 5]

[0073]

[0074] In one aspect of the present invention, the 5,6-dihydroxyindole compound may be 5,6-dihydroxy-1H-indole-2-carboxylic acid of the following chemical formula 6.

[0075] [Chemical Formula 6]

[0076]

[0077] The acid addition salt of the above compound may be selected from, but is not limited to, hydrobromide, hydrochloride, sulfate, phosphate, acetate, propionate, lactate, or citrate. Preferably, the acid addition salt is hydrobromide. In 2003, the European Commission (SCCNFP) announced that 5,6-dihydroxyindoline hydrobromide is harmless to the human body when used as a dye ingredient at a concentration of 2% or less.

[0078] From the perspective of a dyeing shampoo, the hair dyeing composition of the present invention may have a pH value of 5 to 8, preferably 6 to 7, and more preferably 6.2 to 6.8.

[0079] When the pH value of the hair dyeing composition of the present invention exceeds 8, the dye is quickly produced with oxygen in the air, but when used as a shampoo ingredient, it causes severe staining on hands and nails, and if stained on hands, the staining lasts for more than a week. Therefore, when using the hair dyeing composition of the present invention as a dyeing shampoo, the pH value is preferably 8 or lower. The research results of the present invention have confirmed that skin staining is reduced as the pH value decreases.

[0080] If the pH value of the hair dyeing composition of the present invention is less than 5, the 5,6-dihydroxyindoline compound or the 5,6-dihydroxyindole compound is almost always present in a salt form, and thus has low oxidation reactivity (hair dyeing activity), and may not be suitable for a dyeing shampoo that requires a quick use time (within about 5 minutes, preferably within 3 minutes).

[0081] The hair dyeing composition of the present invention may further include a pH adjuster to lower or raise the pH of the composition in addition to the dye active ingredient. The pH adjuster for lowering the pH may be an organic acid or an inorganic acid, and the pH adjuster for raising the pH may be an organic base or an inorganic base.

[0082] The organic acid may be, but is not limited to, citric acid, lactic acid, tartaric acid, acetic acid, salicylic acid, butanoic acid, pentanoic acid, palmitic acid, oxalic acid, succinic acid, glutaric acid, propionic acid, maleic acid, sulfonic acid, and the like.

[0083] The above inorganic acid may be, but is not limited to, hydrobromic acid, hydrochloric acid, sulfuric acid, phosphoric acid, etc.

[0084] The organic base may be, but is not limited to, trihexylamine, triisobutylamine, triethanolamine, trioctylamine, triisodecylamine, trimethylene dipiperidine, and the like.

[0085] The above inorganic base may be, but is not limited to, sodium bicarbonate, potassium bicarbonate, calcium bicarbonate, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc.

[0086] The hair dyeing composition of the present invention may be composed of a single formulation or a two-component formulation. A single formulation means that the composition of the present invention can be used alone as a single formulation, and a two-component formulation means that the composition of the present invention is divided into a first formulation and a second formulation, and hair dyeing is possible by mixing them.

[0087] If the hair dyeing composition of the present invention is a single-part type, it must be stored in an oxygen-blocking container.

[0088] Since the pKa value of 5,6-dihydroxyindoline hydrogen bromide is around 6.2, when the pH of the salt solution is adjusted to 6.2, the salt form and free form exist in a ratio of 50%:50%, and at pH 6.6, the salt form and free form exist in a ratio of 28.5%:71.5%, so the higher the pH, the more the free form exists, which reacts with oxygen and causes coloring.

[0089] In the present invention, it is disclosed that the pH of the 5,6-dihydroxyindoline bibromide solution that does not react with oxygen is 5 or less. Therefore, if a shampoo solution having a pH of 6.6 is prepared, it must be stored in an oxygen-blocking container to enable long-term storage.

[0090] Meanwhile, the hair dyeing composition of the present invention may be formulated as a two-component formulation comprising a first component and a second component to address the issue of requiring an oxygen-blocking container when manufactured as a single-component formulation. The two-component formulation of the present invention has the advantage of not requiring storage in an expensive, special oxygen-blocking container.

[0091] The above first agent contains an acid addition salt of the 5,6-dihydroxyindoline compound or an acid addition salt of the 5,6-dihydroxyindole compound, and does not react with oxygen in the air under acidic conditions of pH 5 or lower, thereby not causing dye activity.

[0092] As the pH value of the above first agent decreases, the risk of skin irritation increases, and as the pH value increases, the reactivity with oxygen increases, which may result in the creation of insoluble dyes during storage, making it difficult to color hair.

[0093] In one embodiment of the present invention, the pH value of the first agent may be 2 to 6, preferably 2.5 to 5, and more preferably 3 to 4. If the pH value is strongly acidic, which is less than 2, there is a risk of skin irritation during dyeing, and if the pH value is greater than 6, the dye is highly reactive with oxygen, and thus, when stored in a general pumping container that does not block oxygen, an insoluble dye may be generated, making it difficult to color hair.

[0094] The above-mentioned second agent is a composition having basicity or neutrality, and when mixed with the first agent, it increases the pH of the first agent, thereby causing the hair dyeing activity of the 5,6-dihydroxyindoline compound or the 5,6-dihydroxyindoline compound. That is, as the pH of the first agent increases, the free form of the active ingredient increases and reacts with oxygen in the air, thereby activating the ingredient.

[0095] The pH value of the above-mentioned second agent is 7 to 13, preferably 7 to 10, and more preferably 7 to 9. However, the pH value of the above-mentioned second agent may vary depending on the pH of the first agent and the amount of mixing with the first agent.

[0096] Since the above-mentioned first and second agents perform a hair dyeing action by being mixed together, they can be contained in separate spaces within a single container or in independent individual containers. Since the above-mentioned first and second agents are stable to oxygen, they do not need to be stored in separate oxygen-blocking containers, offering advantages in terms of storage and cost compared to the single-agent type.

[0097] When the first and second agents of the present invention are mixed, the pH value may be pH 5 to 8, preferably pH 6 to 7, and more preferably 6.2 to 6.8.

[0098] The pKa value of 5,6-dihydroxyindoline bibromide is approximately 6.2, and when the pH of the solution is 6.2, the salt form and the free form exist in a ratio of 50%:50%. At pH 6.6, the salt form and the free form exist in a ratio of 28.5%:71.5%, and as the pH increases, the oxygen reactivity increases.

[0099] In the present invention, the term "mixing" of Agent 1 and Agent 2 may refer to sequential application to the hair during the hair dyeing process, or to mixing Agent 1 and Agent 2 and applying them to the hair prior to dyeing. When applying them sequentially to the hair, it is preferable to apply Agent 1 first and then Agent 2.

[0100] In the present invention, applying to hair may mean holding it in one's hand and washing the hair, or using a tool such as a comb or brush.

[0101] The above polyphenol compound may be included in the first and / or second agents.

[0102] In the present invention, polyphenol or polyphenol-based compound refers to a compound or pigment compound that can cause a browning phenomenon by polyphenol peroxidase. The present invention is characterized in that, instead of polyphenol peroxidase having a slow oxidation reaction rate, at least one selected from the group consisting of an acid addition salt of a 5,6-dihydroxyindoline-based compound of the above-described chemical formula 1, a 5,6-dihydroxyindoline-based compound of the chemical formula 2, and a polydihydroxyindole compound of the chemical formula 3 is used as a reaction initiator for polyphenol polymerization.

[0103] The above polyphenol compound may be a plant-derived compound or a plant extract, or may also be a chemical compound.

[0104] Polyphenols are known to be present in thousands of plant species, including catechin in green tea, resveratrol in grape skin, quercetin in apples and onions, as well as anthocyanins and proanthocyanins. Flavonoids, which are abundant in fruits, and isoflavones, which are abundant in soybeans, are also types of polyphenols. Polyphenols are pigments and bitter-tasting components of plants produced through photosynthesis, so they are mainly found in foods with bright colors and astringent or bitter tastes, such as grapes.

[0105] In the present invention, the term 'polyphenol compound' may be abbreviated as 'polyphenol', and is used to mean not only polyphenol but also decomposition compounds of polyphenol.

[0106] The polyphenol compound of the present invention may be a trihydroxybenzoic acid compound, a dihydroxybenzoic acid compound, dihydroxycinnamic acid or a derivative thereof. The trihydroxybenzoic acid compound or a derivative thereof may be gallic acid, C 1~10 Alkyl gallate, 2,3,4-trihydroxybenzoic acid, syringic acid, etc. Dihydroxybenzoic acid compounds or derivatives thereof may be protocatechic acid, vanillic acid, etc. Dihydroxycinnamic acid may be caffeic acid, etc.

[0107] The polyphenol compound of the present invention may be a tannin compound or a flavonoid compound.

[0108] In the present invention, the tannin compound may be, for example, gallotannin, ellagic acid, ellagitannin, punicalin, punicalagin, etc.

[0109] In the present invention, the flavonoid may be flavanol, flavonol, isoflavonol, flavanone, flavone, flavanonol, or anthocyanin.

[0110] The above flavanol may be, for example, catechin, catechin gallate, epicatechin, gallocatechin, gallocatechin gallate, epigallocatechin, epigallocatechin gallate, etc.

[0111] The above flavonol may be, for example, quercetin, kaempferol, rutin, myricetin, etc.

[0112] The above anthocyanin may be, for example, anthocyanidin, cyanidin, petudinin, malvidin, delphinidin, pelargonidin, etc.

[0113] The above isoflavonol may be, for example, curcumin, genistein, daidzein, etc.

[0114] The above flavanone may be, for example, naringenin, hesperitin, hesperidin, neohesperitin, etc.

[0115] The above flavone may be, for example, baicalein, baicalin, naringin, apigenin, luteolin, chrysin, etc.

[0116] The above polyphenol compound may be a plant extract. In the present invention, using a plant extract containing a polyphenol compound means using a polyphenol compound.

[0117] The above plant extract contains a polyphenol compound, but may contain other ingredients in addition to the polyphenol compound. Furthermore, the polyphenol compound may be a compound manufactured through chemical synthesis. This chemical synthesis allows for mass production.

[0118] Gallic acid can be produced by hydrolyzing tannins found in plants such as beech and acorns.

[0119] Alkyl gallates are ester compounds of gallic acid, which can be extracted from natural sources or synthesized. For example, methyl gallate is found in several plants, including moutan bark and Galla rhois. Ethyl gallate is used as a food additive and is found in various plants, including walnuts and Terminalia chebula, as well as in wine. Propyl gallate is used as a food additive and as a cosmetic ingredient. Alkyl gallates can be prepared by heating gallic acid and an alcohol in the presence of a catalyst, such as sulfuric acid or p-toluene sulfonic acid.

[0120] 2,3,4-Trihydroxybenzoic acid can be extracted from plants such as Betula pendula, Phaseolus vulgaris, and Pachysandra terminalis, or can be synthesized chemically. Ester compounds of 2,3,4-trihydroxybenzoic acid can be synthesized through an ester reaction in the same way as gallic acid esters.

[0121] Natural extracts according to the present invention may be, for example, black bean extract, black sesame extract, rose flower extract, mulberry fruit extract, grape skin extract, green tea extract, onion extract, Pinus thunbergii leaf extract, acacia extract, blueberry extract, aronia extract, and acai berry extract, but these are merely examples and are not limited thereto, and any plant extract containing a large amount of polyphenol can be used in the present invention.

[0122] The natural extract may be an organic solvent extract such as ethanol or methanol, or a hot water extract. The natural extract may be a crude extract or a purified extract. The natural extract may be in the form of a powder or a concentrated liquid.

[0123] Black bean skins contain a large amount of procyanidin, a type of polyphenol. Procyanidin is an oligomeric compound formed from catechin and epicatechin molecules. Black sesame seeds are rich in anthocyanins, a type of polyphenol, and lignans such as sesamin and sesamolin. Rose petals are also rich in anthocyanins, a type of polyphenol.

[0124] The hair dyeing composition of the present invention may be a single-component or two-component type (single-component and double-component), and the hair dyeing composition may be formulated as a liquid, foam, cream, lotion, gel, spray, or powder. The hair dyeing composition may be a hair dye, shampoo, hair foam, hair conditioner, hair treatment, hair spray, hair lotion, hair gel, hair cream, or hair essence formulation, or may be included in the above formulations.

[0125] To prepare the above-described formulation, the hair dyeing composition of the present invention may further include additives such as a pH adjuster, a surfactant, an antioxidant, a swelling agent, a buffer, a viscosity control agent, and a moisturizer. Any additive commonly used in the art may be used without particular limitation.

[0126] The above surfactant may be a nonionic surfactant, a cationic surfactant, an anionic surfactant, an amphoteric surfactant, or a mixture thereof. For example, the surfactant may be a monoglyceride, a diglyceride, a propylene glycol fatty acid ester, a sorbitan monofatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyalkylene and an alkylglyceryl ether, an alkyl sulfate, an alkyl ether sulfate, a sodium alkane sulfonate, an alkyl trimethyl ammonium halide, an alkyl pyridinium halide, an alkyl imidazolium halide, a polyethylene oxide surfactant, a polyvinyl water-soluble polymer, and non-limiting examples thereof include sodium C14-16 olefin sulfonate, sodium dodecyl sulfate, and sodium octylbenzene sulfonate. Examples of the surfactant include, but are not limited to, sodium dodecylbenzene sulfonate, ammonium lauryl sulfate, Triton X-100, and polyvinyl pyrrolidone, cetearyl olivate / sorbitan olivate, sorbitan sesquioleate, etc. The surfactant may be, but is not limited to, 1 to 70 wt% based on the total composition weight. In the case of a two-part form, the surfactant may be included in the first part or the second part or each of them.

[0127] The antioxidant may be, but is not limited to, cysteine, cysteine ​​hydrochloride, N-acetylcysteine, reduced glutathione, D-cysteine, L-cysteine, DL-cysteine ​​or a salt thereof, ascorbic acid or a salt thereof, etc. The antioxidant may be present in an amount of 0.001 to 1 wt% based on the total weight of the composition, but is not limited thereto. In the case of a two-component formulation, the antioxidant may be included in the first or second composition, or each of them.

[0128] The swelling agent is used to enhance the penetration of the hair dyeing composition into the hair. For example, the swelling agent may be urea, thiourea, urea peroxide, polyoxymethylene urea, hydroxyethyl urea, ammonia, triethanolamine, monoethanolamine, and salts thereof, but is not limited thereto. The swelling agent may be present in an amount of 0.01 to 5 wt% based on the total weight of the composition, but is not limited thereto. In the case of a two-component formulation, the swelling agent may be included in the first or second component, or each of them.

[0129] The above buffer may be used without particular limitation as long as it is commonly used in the art, and may include, but is not limited to, salicylic acid, sodium salicylate, lactic acid, sodium lactate, etc.

[0130] The viscosity modifier is used to increase the viscosity of the hair dyeing composition, and may be, for example, a polyacrylic acid polymer, agar, guar gum, gum arabic, dextran, gelatin, xanthan gum, natural cellulose, hydroxypropylmethylcellulose, methyl cellulose, cetearyl alcohol, etc., but is not limited thereto. The viscosity modifier may be present in an amount of 0.01 to 10 wt% based on the total weight of the composition, but is not limited thereto. In the case of a two-part formulation, the viscosity modifier may be included in the first part, the second part, or each of them.

[0131] The above moisturizer may be used without particular limitation as long as it is commonly used in the art, and examples thereof include glycols such as polyethylene glycol, propylene glycol, butylene glycol, oils, etc., but are not limited thereto. The moisturizer may be present in an amount of 0.01 to 10 wt% based on the total weight of the composition, but is not limited thereto. In the case of a two-component formulation, the moisturizer may be included in the first or second component, or each of them.

[0132] Foam (foam) types can be aerosol or non-aerosol. Aerosol types contain a mixture of contents and gas, and the contents are expelled by gas pressure. Non-aerosol types do not contain gas, and the contents form bubbles as they pass through a mesh.

[0133] When the hair dyeing composition of the present invention is a two-component type consisting of a first agent and a second agent, it is possible to mix the first agent and the second agent, which contain a dyeing active ingredient, in advance and then apply them to the hair. Alternatively, the first agent may be first sufficiently applied to the hair and then the second agent may be applied and mixed. In general, since the reaction speed between the first agent and the second agent is fast, the method of applying the second agent after applying the first agent is more preferable.

[0134]

[0135] Hereinafter, the present invention will be described in more detail with reference to the following examples. However, these examples are provided solely to aid understanding of the present invention and are not intended to limit the scope of the present invention in any way.

[0136]

[0137] Example 1: Preparation of Formulation 1

[0138] A hair dyeing composition according to the present invention was prepared using gallic acid as a polyphenol compound and 5,6-dihydroxyindoline hydrobromide as a polyphenol reaction initiator.

[0139] Gallic acid and 5,6-dihydroxyindoline hydrobromide were added to purified water and stirred at 50°C until completely dissolved. Then, sodium bicarbonate or citric acid was added in small amounts as a pH adjuster to adjust the pH of the composition as shown in Table 1 below, thereby preparing a hair dyeing composition. The compositions were stored in an airtight container.

[0140]

[0141] The hair dyeing properties of the hair dyeing composition manufactured in Example 1 were evaluated. About 1 g of the hair dyeing composition was added to a bleached hair sample, shampooed by hand for about 1 minute, rinsed thoroughly with running water, and dried. The above process was repeated twice, and the dyed hair sample is shown in Fig. 1. As shown in Fig. 1, dyeing was poor in the pH 4.0 and pH 5.0 samples, but the sample with a pH of 6.0 or higher was colored black, indicating excellent dyeing properties. However, the composition with a pH of 8.0 caused dye discoloration on the hand, and the sample with a pH of 9.0 was more severely colored, indicating that it is not suitable as a dyeing shampoo.

[0142] The storage stability of the hair dyeing composition manufactured in Example 1 was evaluated.

[0143] The hair dyeing composition of Example 1 was placed in an oxygen-blocking container and a general pumping container, respectively, and after 30 days, the presence or absence of precipitation of solids was checked, and dyeing was performed on a bleached hair sample using the same method as Example 1, and the results are shown in Table 2 below.

[0144]

[0145] The composition of Example 1 demonstrated excellent storage stability, as no sedimentation occurred even after 30 days in an oxygen-blocking container, regardless of pH concentration. This is because the oxygen blocking inhibits the activity of 5,6-dihydroxyindoline. However, under oxygen-blocking conditions, the composition at pH 4.0 exhibited poor hair dyeing properties, and at pH 9.0, severe dye discoloration occurred on the hands.

[0146] The composition of Example 1 generated insoluble black precipitates over time in a general shampoo container, except for the cases of pH 4.0 and pH 5.0. The higher the pH, the faster the precipitate generation rate tended to be, and when the precipitated composition was used to dye bleached hair samples, the dyeing was found to be very poor. This means that at pH 5.0 or higher, the dye component of the present invention reacts with oxygen in the air to generate an insoluble dye substance, which does not color the hair.

[0147] From the above results, the hair dye composition of the present invention can be usefully used as a single-component dyeing shampoo under oxygen blocking and pH 5.0 to 8.0 conditions, more preferably pH 6.0 to 7.0 conditions.

[0148]

[0149] Example 2: Preparation of Formulation 1

[0150] A dyeing shampoo was prepared using the hair dyeing active ingredient and shampoo ingredients of Example 1.

[0151] Sodium C14-16 olefin sulfonate (anionic), coco-glucoside (nonionic), and lauryl hydroxysultaine (amphoteric) were used as surfactants, polyquaternium-7 was used as a conditioning agent, 1,2-hexanediol was used as a moisturizer, and sodium chloride was used as a viscosity modifier. These were added to purified water together with the hair dyeing active ingredient of Example 1, stirred at 50°C until completely dissolved, and then a small amount of sodium bicarbonate was added to raise the pH of the composition to 6.6.

[0152] Table 3 below shows the composition of the dyeing shampoo of Example 2.

[0153]

[0154] After storing the composition in an oxygen-blocking container for 30 days, hair was dyed using the same method as in Example 1, and the results are shown in Fig. 2. The dyeing shampoo composition of this example was found to have excellent dyeing properties. In addition, no dye staining occurred on the hands after the hair dyeing.

[0155]

[0156] Example 3: Preparation of a two-composition composition

[0157] The first agent (acidic composition) in Table 4 and the second agent (basic composition) in Table 5 were each prepared.

[0158] The first and second agents were stored in their respective general pumping containers.

[0159]

[0160]

[0161] Agent 1 is an acidic composition with a pH of 3.5, and Agent 2 is a basic composition with a pH of 8.5, and is designed so that when Agent 1 and Agent 2 are mixed in equal amounts, the pH is approximately 6.6. Agents 1 and 2 were stable without any sedimentation even when stored in a general pumping container for 30 days. After applying about 1 g of Agent 1 to a bleached hair sample for about 1 minute, applying about 1 g of Agent 2 to the bleached hair sample, shampooing for about 1 minute, rinsing in running water, and drying, the dyeing process was performed twice, and the results are shown in Fig. 3.

[0162] As shown in Fig. 3, the dyeability was found to be very excellent. In addition, no discoloration occurred on the hands after dyeing the hair.

[0163]

[0164] Examples 4 to 8: Preparation of a two-component composition

[0165] As shown in Table 6 below, a first composition having a pH of 3.5 was prepared using a natural extract (powder) known to contain gallic acid and a large amount of polyphenol components.

[0166]

[0167] Agent 1 is an acidic composition with a pH of 3.5, and Agent 2 is a basic composition with a pH of 8.5, and was designed to be adjusted to about pH 6.6 when Agent 1 and Agent 2 were mixed. Agents 1 and 2 were stable without any precipitation even when stored in a general pumping container for 30 days. Agent 2 was used in the same manner as Agent 2 manufactured in Example 3, and the hair dyeing process was also performed twice in the same manner, and the results are shown in Fig. 4.

[0168] As shown in Figure 4, the composition of this example demonstrated excellent dyeability without discoloration of the hands. Furthermore, the color tones of the dyed samples varied somewhat depending on the type of natural extract. Therefore, by varying or mixing the types of natural extracts, it is possible to produce a composition capable of dyeing in a variety of hues.

[0169]

[0170] Example 10: Preparation of a two-composition composition

[0171] As shown in Table 7 below, a first composition was prepared using various types of natural extracts as polyphenol components.

[0172] The second composition was used in the same manner as the second composition prepared in Example 3, and the hair dyeing process was also carried out in the same manner, and the results are shown in Fig. 5.

[0173]

[0174] As shown in Fig. 5, the dyeability was found to be very excellent. In addition, no discoloration occurred on the hands after dyeing the hair.

[0175]

[0176] Example 11: Preparation of a two-composition composition

[0177] The first agent in Table 8 below was prepared using propyl gallate and natural extracts as polyphenol components.

[0178] Agent 2 was used in the same manner as Agent 2 manufactured in Example 3, and the hair dyeing process for Agents 1 and 2 was also carried out in the same manner, and the results are shown in Fig. 6.

[0179]

[0180] As shown in Fig. 6, the dyeability was found to be very excellent. In addition, no discoloration occurred on the hands after dyeing the hair.

[0181]

[0182] Example 12: Preparation of Formulation 1

[0183] A hair dyeing composition according to the present invention was prepared using gallic acid as a polyphenol compound and 2-carboxyl-5,6-dihydroxyindoline hydrochloride as a polyphenol reaction initiator.

[0184] Gallic acid and 2-carboxyl-5,6-dihydroxyindoline hydrochloride were added to purified water and stirred at 50°C until completely dissolved. Then, sodium bicarbonate or citric acid was added in small amounts as a pH adjuster to adjust the pH of the composition as shown in Table 9 below, thereby preparing a hair dyeing composition. The compositions were stored in an airtight container.

[0185]

[0186] The hair dyeing properties of the hair dyeing composition manufactured in Example 12 were evaluated. About 1 g of the hair dyeing composition was added to a bleached hair sample, shampooed by hand for about 1 minute, rinsed thoroughly with running water, and dried. The above process was repeated twice, and the dyed hair sample is shown in Fig. 7. As shown in Fig. 7, dyeing was poor in the pH 4.0 and pH 5.0 samples, but the sample with a pH of 6.0 or higher was colored black, indicating excellent dyeing properties. However, the composition with a pH of 8.0 caused dye discoloration on the hand, and the sample with a pH of 9.0 was more severely colored, indicating that it is not suitable as a dyeing shampoo.

[0187] The storage stability of the hair dyeing composition manufactured in Example 12 above was evaluated.

[0188] The hair dyeing composition of Example 12 was placed in an oxygen-blocking container and a general pumping container, respectively, and after 30 days, the presence or absence of precipitation of solids was checked, and bleached hair dyeing was performed using the same method as Example 1, and the results are shown in Table 10 below.

[0189]

[0190] The composition of Example 12 demonstrated excellent storage stability, as no sedimentation occurred even after 30 days in an oxygen-blocking container, regardless of pH concentration. This is because the activity of 5,6-dihydroxyindoline was inhibited by oxygen blocking. However, under oxygen-blocking conditions, the composition at pH 4.0 exhibited poor hair dyeing properties, and at pH 9.0, severe dye discoloration occurred on the hands.

[0191] The composition of Example 12 produced insoluble black precipitates over time in a general shampoo container, except for pH 4.0 and pH 5.0. The higher the pH, the faster the precipitate formation rate, and when the precipitated composition was used to dye bleached hair samples, the dyeing was found to be very poor. This means that at pH 5.0 or higher, the dye component of the present invention reacts with oxygen in the air to produce an insoluble dye substance, which does not color the hair.

[0192] From the above results, the hair dye composition of the present invention can be usefully used as a single-component dyeing shampoo under oxygen blocking and pH 5.0 to 8.0 conditions, more preferably pH 6.0 to 7.0 conditions.

[0193]

[0194] Examples 13 to 18: Preparation of a two-component composition

[0195] As shown in Table 11 below, a first composition having a pH of 3.5 was prepared using a natural extract known to contain gallic acid and a large amount of polyphenol components as polyphenol components, and 2-carboxyl-5,6-dihydroxyindoline hydrochloride as a reaction initiator.

[0196]

[0197] Agent 1 is an acidic composition with a pH of 3.5, and Agent 2 is a basic composition with a pH of 8.5, and was designed to be adjusted to about pH 6.6 when Agent 1 and Agent 2 were mixed. Agents 1 and 2 were stable without any precipitation even when stored in a general pumping container for 30 days. Agent 2 was used in the same manner as Agent 2 of Table 5 manufactured in Example 3, and the hair dyeing process was also performed twice in the same manner, and the results are shown in Fig. 8.

[0198] As shown in Figure 8, the composition of this example demonstrated excellent dyeability without discoloration of the hands. Furthermore, the color tones of the dyed samples varied somewhat depending on the type of natural extract. Therefore, by varying or mixing the types of natural extracts, it is possible to produce a composition capable of dyeing in a variety of hues.

[0199] Example 19: Preparation of Formulation 1

[0200] A hair dyeing composition according to the present invention was prepared using gallic acid as a polyphenol compound and 5,6-dihydroxyindole-1H-2-carboxylic acid as a polyphenol reaction initiator.

[0201] Gallic acid and 5,6-dihydroxyindole-1H-2-carboxylic acid were added to purified water and stirred at 50°C until completely dissolved. Then, sodium bicarbonate or citric acid was added in small amounts as a pH adjuster to adjust the pH of the composition as shown in Table 12 below, thereby preparing a hair dyeing composition. The compositions were stored in an airtight container.

[0202]

[0203] The hair dyeing properties of the hair dyeing composition manufactured in Example 19 were evaluated. About 1 g of the hair dyeing composition was added to a bleached hair sample, shampooed by hand for about 1 minute, rinsed thoroughly with running water, and dried. The above process was repeated twice, and the dyed hair sample is shown in Fig. 9. As shown in Fig. 9, dyeing was poor in the pH 4.0 and pH 5.0 samples, but the sample with a pH of 6.0 or higher was colored black, indicating excellent dyeing properties. However, the composition with a pH of 8.0 caused dye discoloration on the hand, and the sample with a pH of 9.0 was more severely colored, indicating that it is not suitable as a dyeing shampoo.

[0204] The storage stability of the hair dyeing composition manufactured in Example 19 was evaluated.

[0205] The hair dyeing composition of Example 19 was placed in an oxygen-blocking container and a general pumping container, respectively, and after 30 days, the presence or absence of precipitation of solids was checked, and bleached hair dyeing was performed in the same manner as Example 1, and the results are shown in Table 13 below.

[0206]

[0207] The composition of Example 19 exhibited excellent storage stability, as no sedimentation occurred even after 30 days in an oxygen-blocking container, regardless of pH concentration. This is because the activity of 5,6-dihydroxyindoline was inhibited by oxygen blocking. However, under oxygen-blocking conditions, the composition at pH 4.0 exhibited poor hair dyeing properties, and at pH 9.0, severe dye discoloration occurred on the hands.

[0208] The composition of Example 19 produced insoluble black precipitates over time in a general shampoo container, except for the cases of pH 4.0 and pH 5.0. The higher the pH, the faster the precipitate formation rate tended to be, and when the precipitated composition was used to dye bleached hair samples, the dyeing was found to be very poor. This means that at pH 5.0 or higher, the dye component of the present invention reacts with oxygen in the air to produce an insoluble dye substance, which does not color the hair.

[0209] From the above results, the hair dye composition of the present invention can be usefully used as a single-component dyeing shampoo under oxygen blocking and pH 5.0 to 8.0 conditions, more preferably pH 6.0 to 7.0 conditions.

[0210]

[0211] Examples 20 to 25: Preparation of a two-component composition

[0212] As shown in Table 14 below, a first composition having a pH of 3.5 was prepared using a natural extract known to contain gallic acid and a large amount of polyphenol components as polyphenol components, and 5,6-dihydroxyindole-1H-2-carboxylic acid as a reaction initiator.

[0213]

[0214] Agent 1 is an acidic composition with a pH of 3.5, and Agent 2 is a basic composition with a pH of 8.5, and was designed to be adjusted to about pH 6.6 when Agent 1 and Agent 2 were mixed. Agents 1 and 2 were stable without any precipitation even when stored in a general pumping container for 30 days. Agent 2 was used in the same manner as Agent 2 of Table 5 manufactured in Example 3, and the hair dyeing process was also performed twice in the same manner, and the results are shown in Fig. 10.

[0215] As shown in Figure 10, the composition of this example demonstrated excellent dyeability without discoloration of the hands. Furthermore, the color tones of the dyed samples varied somewhat depending on the type of natural extract. Therefore, by varying or mixing the types of natural extracts, it is possible to produce a composition capable of dyeing in a variety of hues.

[0216]

[0217] Example 26: Preparation of a two-composition composition

[0218] As shown in Table 15 below, a first composition having a pH of 3.5 was prepared using gallic acid and black bean extract as polyphenol components and 5,6-dihydroxyindoline hydrobromide and polyhydroxyindole as reaction initiators.

[0219]

[0220] Agent 1 is an acidic composition with a pH of 3.5, and Agent 2 is a basic composition with a pH of 8.5, and was designed to be adjusted to about pH 6.6 when Agent 1 and Agent 2 were mixed. Agents 1 and 2 were stable without any precipitation even when stored in a general pumping container for 30 days. Agent 2 was used in the same manner as Agent 2 prepared in Example 3, and the hair dyeing process was also performed twice in the same manner, and the results are shown in Fig. 11.

[0221] The present invention relates to a composition for hair dyeing, and more specifically, to a composition that can be used in a hair dyeing shampoo, hair dye (dye agent), etc.

Claims

1. 1) Polyphenol compounds; and 2) Containing at least one selected from the group consisting of an acid addition salt of a 5,6-dihydroxyindole compound of the following chemical formula 1, a 5,6-dihydroxyindole compound of the following chemical formula 2, and a polydihydroxyindole compound of the following chemical formula 3. Composition for hair dyeing. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] (In the above chemical formulas, R 1 , R 3 , R 4 and R 5 are each independently H or C 1-4 It is alkyl, R 2 is H, C 1-4 Alkyl or carboxyl, X is greater than or equal to 2.) 2. In paragraph 1, A hair dyeing composition, characterized in that the above hair dyeing composition has a pH value of 5 to 7.

3. In paragraph 1, The above hair dyeing composition is, 1) A first agent comprising at least one selected from the group consisting of acid addition salts of the above 5,6-dihydroxyindole compounds, 5,6-dihydroxyindole compounds and polydihydroxyindole compounds and having a pH value of 2 to 6; and 2) Contains two agents with a pH value of 7 to 13, A hair dyeing composition, characterized in that the first or second agent comprises a polyphenol compound.

4. In any one of paragraphs 1 to 3, The above 5,6-dihydroxyindoline compound is 5,6-dihydroxyindoline or 5,6-dihydroxyindoline-2-carboxylic acid, A hair dyeing composition, characterized in that the above 5,6-dihydroxyindole compound is 5,6-dihydroxy-1H-indole-2-carboxylic acid.

5. In any one of paragraphs 1 to 3, A hair dyeing composition, characterized in that the acid addition salt is at least one selected from the group consisting of hydrobromide, hydrochloride, sulfate, phosphate, acetate, propionate, lactate, and citrate.

6. In any one of paragraphs 1 to 3, A hair dyeing composition, characterized in that the polyphenol compound is a plant-derived compound, a plant extract, or a synthetic compound.

7. In any one of paragraphs 1 to 3, The above polyphenol compounds include gallic acid, C 1~10 Alkyl gallate, 2,3,4-Trihydroxybenzoic acid, syringic acid, protocatechic acid, vanillic acid, caffeic acid, tannin, catechin, catechin gallate, epicatechin, gallocatechin, gallocatechin gallate, epigallocatechin, epigallocatechin gallate, quercetin, kaempferol, rutin, myricetin, anthocyanin, anthocyanidin, A hair dyeing composition characterized in that it comprises at least one selected from the group consisting of cyanidin, petudinin, malvidin, delphinidin, pelargonidin, curcumin, genistein, daidzein, naringenin, hesperitin, hesperidin, neohesperitin, baicalein, baicalin, naringin, apigenin, luteolin, chrysin, and resveratrol.

8. In paragraph 3, A hair dyeing composition characterized in that the pH value of the first agent is 3 to 4.

9. In paragraph 3, A hair dyeing composition characterized in that the pH value of the above two agents is 7 to 9.

10. In any one of paragraphs 1 to 3, A hair dyeing composition, characterized in that the compound comprising at least one selected from the group consisting of an acid addition salt of the above 5,6-dihydroxyindole compound, a 5,6-dihydroxyindole compound, and a polydihydroxyindole compound is present in an amount of 0.1 to 10 wt% based on the total weight of the hair dyeing composition.

11. In any one of paragraphs 1 to 3, A hair dyeing composition, characterized in that the polyphenol compound is 0.1 to 10 wt% based on the total weight of the hair dyeing composition.

12. In any one of paragraphs 1 to 3, A hair dyeing composition characterized in that the above hair dyeing composition further comprises at least one selected from a surfactant, an antioxidant, a swelling agent, a buffer, a viscosity modifier, and a moisturizer.

13. In any one of paragraphs 1 to 3, A hair dyeing composition, characterized in that the hair dyeing composition is formulated as a liquid, foam, cream, lotion, gel, spray or powder.

14. In any one of paragraphs 1 to 3, The above hair dyeing composition is a hair dye, shampoo, hair foam, hair conditioner, hair treatment, hair spray, hair lotion, hair gel, hair cream or hair essence formulation, or a hair dyeing composition included in the above formulation.

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