Hair color composition

Abstract

The present invention provides a hair color composition which contains a compound having a biphenyl nucleus and thus can develop color upon contact with oxygen. The composition enables hair dyeing without hair damage or a hypersensitive response from the scalp, can be used together with a surfactant to prevent phase separation and precipitation of the composition, thereby exhibiting excellent preservation, and can exhibit excellent dyeability without discoloration even when used together with a pigment.

Description

Hair color composition

[0001] This application is based upon and claims priority to Korean Patent Application No. 10-2024-0042527, filed with the Korean Intellectual Property Office on March 28, 2024, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a hair color composition that does not cause hair damage and scalp hypersensitivity.

[0003] Hair dyeing has traditionally been used to tone down gray hair that develops with aging, or to enhance aesthetics by dyeing hair in a variety of colors or shades. Traditionally, hair dyeing involved applying a hair dye containing a hair dye composition to the hair, leaving it for a set period of time, and then dyeing. Recently, research is being conducted into methods for incorporating hair dye compositions into functional cosmetics for the hair or scalp, thereby imparting a hair dyeing effect in addition to the inherent functionality of the cosmetic.

[0004] Traditional hair dyeing compositions primarily contained oxidizing agents to decompose and bleach hair melanin and oxidize oxidizing dye precursors. However, oxidizing agents such as hydrogen peroxide can damage hair during the bleaching process and cause scalp irritation, while oxidizing dyes can cause scalp allergic reactions. With the growing interest in both beauty and health, research is being conducted on methods to improve not only the stability of hair dyeing but also the health of hair and scalp.

[0005] An object of the present invention is to provide a hair color composition capable of imparting color to hair without ingredients such as hydrogen peroxide and ammonia that cause skin irritation.

[0006] A hair color composition according to one specific example of the present invention may include a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] Among the foods,

[0010] R1 is hydrogen, hydroxyl or carboxyl group,

[0011] R2 and R3 are independently hydrogen, carboxyl group, C1-C 10 Alkyl group, C1-C 10 Haloalkyl group, C1-C 10 Alkoxy group, C1-C 10 It is a haloalkoxy group, an amine group, or a C1-C4 aminoalkyl group.

[0012] In the above formula, R1 may be a hydroxy group, and R2 and R3 may each be hydrogen.

[0013] The hair color composition may contain 0.01 wt% to 1.95 wt% of the compound of the above chemical formula 1 based on the total weight of the above hair color composition.

[0014] The above hair color composition may further include 0.2 wt% to 21 wt% of a surfactant based on the total weight of the hair color composition.

[0015] The above surfactant may be at least one selected from the group consisting of cationic surfactants, anionic surfactants, nonionic surfactants, and amphoteric surfactants.

[0016] The above hair color composition further includes a pigment, and the weight ratio of the pigment to the weight of the surfactant may be 0.00005 to 0.5.

[0017] The above hair color composition can be formulated as a 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 treatment agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair glaze, hair lacquer, hair moisturizer, hair mousse or hair spray.

[0018] The hair color composition according to the present invention can dye hair without hair damage or scalp hypersensitivity, and can exhibit excellent preservation properties without color transfer.

[0019] Figure 1 is an image confirming the appearance of hair color compositions according to Examples 1 to 4 and Comparative Examples 1 and 2.

[0020] FIG. 2 shows (a) an image and (b) a colorimetric value L* of bleached hair samples treated with hair color compositions according to Examples 1 to 4 and Comparative Examples 1 and 2.

[0021] Figure 3 is an image confirming the appearance of the hair color composition according to Examples 2 and 5 and Comparative Examples 3 and 4.

[0022] FIG. 4 is (a) an image and (b) a colorimetric value L* of a bleached hair sample after treatment with a hair color composition according to Examples 2 and 5 and Comparative Examples 3 and 4.

[0023] Figure 5 is an image confirming the appearance of the hair color composition according to Examples 2, 6 to 15.

[0024] FIG. 6 is an image of a bleached hair sample after treatment with a hair color composition according to Examples 2, 6 to 15.

[0025] FIG. 7 is the colorimetric value L* of bleached hair samples treated with hair color compositions according to Examples 2, 6 to 15.

[0026] Figure 8 is an image confirming the appearance of hair color compositions according to Examples 2, 6, 16, 17 and Comparative Examples 5 and 6.

[0027] FIG. 9 is an image (a) and a colorimetric value L* (b) of bleached hair samples treated with hair color compositions according to Examples 2, 6, 16, 17 and Comparative Examples 5 and 6.

[0028] Fig. 10 is an image showing the appearance of a hair color composition according to Examples 2, 18 to 21 and Comparative Examples 7 and 8, and the appearance after the composition is applied to a plastic plate and a palm and then washed with water.

[0029] FIG. 11 is (a) an image and (b) a colorimetric value L* of a bleached hair sample after treatment with a hair color composition according to Examples 2, 18 to 21 and Comparative Examples 7 and 8.

[0030] Hereinafter, each component of the present invention will be described in more detail so that a person having ordinary skill in the art to which the present invention pertains can easily practice it; however, this is only an example, and the scope of the rights of the present invention is not limited by the following contents.

[0031] The term "comprises" as used herein is used to list materials, compositions, devices, and methods useful in the present invention, but is not limited to the listed examples.

[0032] In the present invention, “hair” refers to a thread-like structure that emerges from the surface of the skin, and encompasses body hair and scalp hair.

[0033]

[0034] A hair color composition according to one specific example of the present invention comprises a compound of the following chemical formula 1, and the hair color composition can be colored by contact with oxygen.

[0035] [Chemical Formula 1]

[0036]

[0037] Among the foods,

[0038] R1 is hydrogen, hydroxyl or carboxyl group,

[0039] R2 and R3 are independently hydrogen, carboxyl group, C1-C 10 Alkyl group, C1-C 10 Haloalkyl group, C1-C 10 Alkoxy group, C1-C 10 It is a haloalkoxy group, an amine group, or a C1-C4 aminoalkyl group.

[0040] Specifically, in the above chemical formula 1, R1 may be hydrogen or a hydroxyl group, and R2 and R3 may independently be hydrogen, a carboxyl group, or an amine group. Preferably, R1 may be hydrogen or a hydroxyl group, and R2 and R3 may be hydrogen.

[0041] The compound of the above chemical formula 1 can be adsorbed onto the surface of hair when the hair color composition is applied to the hair, and the compound of the above chemical formula 1 can impart color (dyeing) to hair in the presence of oxygen. Specifically, the compound of the above chemical formula 1 can impart brown color to hair. The compound of the above chemical formula 1 can form a coating layer on at least a portion of the surface of hair when the hair color composition is applied to the hair.

[0042] The compound of the above chemical formula 1 may be a compound of the following chemical formula 2 (HDP; 1,1'-biphenyl-2,2',4,4',5,5'-hexanol) in which R1 is a hydroxy group and R2 and R3 are hydrogen.

[0043] [Chemical Formula 2]

[0044]

[0045] The above hair color composition may contain 0.01 wt% to 1.95 wt% of the compound of the above chemical formula 1 based on the total weight of the hair color composition. Specifically, for 100 wt% of the hair color composition, the compound of the formula 1 may be 0.01 wt% or more and 1.95 wt% or less, 0.05 wt% or more and 1.90 wt% or less, 0.10 wt% or more and 1.80 wt% or less, 0.20 wt% or more and 1.70 wt% or less, 0.30 wt% or more and 1.60 wt% or less, 0.40 wt% or more and 1.50 wt% or less, 0.50 wt% or more and 1.40 wt% or less, 0.60 wt% or more and 1.30 wt% or less, 0.70 wt% or more and 1.20 wt% or less, 0.80 wt% or more and 1.10 wt% or less, or 0.90 wt% or more and 1.00 wt% or less. Preferably, the compound of the chemical formula 1 may be 0.03 wt% or more and 1.00 wt% or less based on the total weight of the hair color composition. If the content of the compound of the chemical formula 1 is less than 0.01 wt%, even if the hair color composition is applied to hair, the color inherent to the compound is not expressed, and if the content of the compound of the chemical formula 1 exceeds 1.95 wt%, the compounds of the chemical formula 1 clump together and precipitate during storage of the hair color composition.

[0046] The above hair color composition may further include a surfactant. The surfactant may be a cationic surfactant, an anionic surfactant, a nonionic surfactant, and an amphoteric surfactant, but may preferably be a cationic surfactant. The surfactant may prevent precipitation of the compound of the above chemical formula 1 and improve the storage stability of the hair color composition. When used together with a pigment described below, at least a portion of the surfactant may form a physical bond with the pigment, thereby preventing the pigment from transferring to areas other than the hair.

[0047] For example, the cationic surfactant is polyquaternium-67, Miconium TM CTAC29, STAC 80KC, MITAINE LPB(N), MITAINE CA-GF, Cetrimonium Chloride, Stearimonium Chloride, Behentrimonium Chloride, Behentrimonium Methosulfate, Behenamidopropyltrimonium Methosulfate, Stearamidopropyltrimonium Chloride, Arachidtrimonium Chloride, Distearyldimonium Chloride, Dicetyldimonium Chloride, Tricetylmonium Chloride, Oleamidopropyl Dimethylamine, Linoleamidopropyl Dimethylamine, Stearamidopropyl Dimethylamine, Oleyl Hydroxyethyl Imidazoline, Stearamidopropyl Dimethylamine, Behenamidopropyl Dimethylamine, Behenamidopropyl Diethylamine, Behenamidoethyl Diethylamine, Behenamidoethyl Dimethylamine, Arachidamidopropyl Dimethylamine, It may be arachidamidopropyldiethylamine, arachidamidoethyldiethylamine, arachidamidoethyldimethylamine, etc.

[0048] For example, the nonionic surfactant is Plantacare ® 2000, Plantacare ® 818, ELOTANT TMMILCOSIDE 240 HE, PPG-2 cocamide, cocamide MEA, cocamide DEA, palm kernel oil fatty acid amide DEA, lauramido DEA, cocamide methyl MEA, 2-ethylhexylglyceryl ether, alkyl glyceryl ether, alkyl glucoside, ethylene oxide derivative of alkylphenol formalin condensate, alkyl polyglucoside, polyoxyethylene glycerin isostearate, isodecyl glyceryl ether, glycerin alkyl ether, glycerin fatty acid ester, sorbitan sesquioleate, ceteareth 60 myristyl glycol, sorbitan monostearate, sorbite fatty acid ester, tetraisostearate polyoxyethylene sorbite, tetraglycerin monolauryl ether, tetrapolyoxyalkylene ethylenediamine condensate, propylene glycol fatty acid ester, pentaerythritol Fatty acid ester, polyethylene glycol type nonionic surfactant, polyethylene glycol fatty acid ester, polyoxyalkylene alkyl co-modified organopolysiloxane, polyoxyalkylene alkyl ethers, polyoxyalkylene alkyl phenyl ethers, polyoxyalkylene alkenyl ethers, polyoxyalkylene ethers, polyoxyalkylene esters, polyoxyalkylene glycols, polyoxyalkylene glycol fatty acid esters, polyoxyalkylene glycerin fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbite fatty acid esters, polyoxyalkylene castor oil derivatives, polyoxyalkylene hydrogenated castor oil derivatives, polyoxyalkylene fatty acid amides, polyoxyalkylene fatty acid esters, polyoxyalkylene modified organopolysiloxanes, polyoxyethylene alkylamines, polyoxyethylene alkylallyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkylthio ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene isostearyl ethers, polyoxyethylene cholestanol Ether, polyoxyethylene cholesteryl ether, polyoxyethylene stanol ether, polyoxyethylene stearyl ether, polyoxyethylene sterol ether, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene nonylphenyl ether, polyoxyethylene castor oil,Polyoxyethylene phytosteryl ether, polyoxyethylene phytosterol ether, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene polyoxypropylene butyl ether, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene glyceryl ether, polyoxyethylene methyl glucoside, polyoxyethylene coconut oil fatty acid PEG-glyceryl, polyoxyethylene lauryl ether, polyoxyethylene lanolin derivative, polyoxyethylene hydrogenated castor oil, polyoxyethylene hydrogenated castor oil fatty acid ester, polyoxyethylene hydrogenated castor oil derivative, polyoxysorbitol fatty acid ester, polyoxybutylenepolyoxyethylenepolyoxypropylene glyceryl ether, polyoxypropylene alkyl ether, polyglyceryl ether, polyglyceryl monoalkyl ether, polyglycerin alkyl ether, polyglycerin laurate ester, polyglycerin fatty acid ester, polysorbate, Monoalkyl glyceryl ether, monoalkenyl glyceryl ether, ethylene glycol monooleate, monoglyceride derivative, monoglycerin alkyl ether, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monolaurate, PEG-2 laurate, PEG-4 laurate, propylene glycol laurate, hydrogenated castor oil derivative, higher fatty acid sucrose ester, fatty acid oxybutylene, fatty acid glycol ester, fatty acid glycerin ester, fatty acid deoxybutylene, etc.

[0049] For example, the anionic surfactant is an alginate surfactant, Keltrol ®F, sodium lauryl sulfate, triethanolamine lauryl sulfate, sodium myristyl sulfate, sodium stearyl sulfate, sodium cetyl sulfate, sodium polyoxyethylene lauryl ether sulfate, sodium polyoxyethylene myristyl ether sulfate, sodium tetradecene sulfonate, sodium myristoyl methyl taurine, sodium palmitoyl methyl taurine, sodium dioctyl sulfosuccinate, lauryl disodium sulfosuccinate, polyoxyethylene lauryl disodium sulfosuccinate, sodium lauryl phosphate, polyoxyethylene lauryl ether phosphate, polyoxyethylene cetyl ether phosphate, polyoxyethylene oleyl ether phosphate, sodium polyoxyethylene alkylphenyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate triethanolamine, potassium lauroyl sarcosine, triethanolamine lauroyl sarcosine, sodium myristoyl sarcosinate, Coconut oil fatty acid sarcosinate sodium, lauroyl methylalanine sodium, lauroyl methylalanine triethanolamine, myristoyl methylalanine sodium, coconut oil fatty acid methylalanine sodium, sodium myristoyl glutamate, potassium stearoyl glutamate, disodium stearoyl glutamate, coconut oil fatty acid acylglutamate sodium, coconut oil fatty acid acyl glutamate triethanolamine, coconut oil fatty acid acyl glycine potassium, coconut oil fatty acid acyl glycine sodium, lauryl glycol acetate sodium, lauryl glycol acetate potassium, myristyl glycol acetate sodium, myristyl glycol acetate potassium, palmityl glycol acetate sodium, palmityl glycol acetate potassium, stearyl glycol acetate sodium, stearyl glycol acetate potassium, etc.

[0050] For example, the amphoteric surfactant may be lauric acid amide propyl betaine, coconut oil fatty acid amide propyl betaine, alkyl glycine salt, carboxymethyl glycine salt, N-acyl amino ethyl-N-2-hydroxy ethyl glycine salt, alkyl aminopropionate, alkyldimethyl aminoacetic acid betaine, alkyl dihydroxy ethylaminoacetic acid betaine, N-alkyl-N, N-dimethylammonium-N-(2-hydroxypropyl) sulfonate, N-fatty acid amide propyl-N, N-dimethylammonium-N-(2-hydroxypropyl) sulfonate, alkylhydroxy sulfobetaine, etc.

[0051] Preferably, the surfactant may be a cationic surfactant. When the surfactant is a cationic surfactant, the adsorption capacity of the hair color composition to negatively charged hair can be further enhanced, and at the same time, the hair color composition can impart flexibility to the hair surface. Most preferably, the surfactant may be polyquaternium-67. Polyquaternium-67 has a high positive charge, so that the hair color composition can have the best adsorption capacity to hair and the flexibility-providing effect.

[0052] The hair color composition may contain the surfactant in an amount of 0.2 wt% to 21 wt% based on the total weight of the hair color composition. The surfactant contained in the hair color composition may be referred to as a surfactant contained in a base for formulation described below and a surfactant added independently of the base. For example, the hair color composition may contain a compound of Chemical Formula 1, a surfactant, and a base, and the base may also contain a surfactant. The surfactant and the surfactant contained in the base may be the same or different from each other. Specifically, with respect to 100 wt% of the hair color composition, the surfactant may be present in an amount of 0.2 wt% to 21 wt%, 1 wt% to 18 wt%, 2 wt% to 16 wt%, 3 wt% to 15 wt%, 4 wt% to 14 wt%, 5 wt% to 13 wt%, 6 wt% to 12 wt%, 7 wt% to 11 wt%, or 8 wt% to 10 wt%. Preferably, the surfactant may be present in an amount of 0.9 wt% to 21 wt%, or 14 wt% to 18 wt%. If the content of the surfactant is less than 0.2 wt%, the fluidity of the hair color composition cannot be secured due to the addition of the surfactant with respect to the content of the compound of the above-mentioned chemical formula 1, and storage stability may be deteriorated. If the content of the above surfactant exceeds 21 wt%, coagulation of solids may occur within the hair color composition due to the surfactant included in excessive amount.

[0053] The above hair color composition may further include a pigment. Specifically, the pigment may have low or no adhesion or adsorption to the hair on its own, making it difficult to form a coating layer that coats at least a portion of the hair surface. For example, the pigment may contact the hair to impart the hair with the color of the pigment, but this is temporary and the color does not last long. In the process of applying the pigment to the hair, the pigment may transfer to an unwanted part other than the hair, such as the hand or arm. A hair color composition comprising the compound of Chemical Formula 1, the surfactant, and the pigment can maintain the pigment on the surface of the hair while the compound of Chemical Formula 1 forms a coating layer on the surface of the hair, and the compound of Chemical Formula 1 and the surfactant can prevent the transfer of the pigment.

[0054] The above pigments include azo pigments such as Red No. 40 (Allura Red AC, CAS No. 25956-17-6), Red No. 228 (Permaton Red, CAS No. 2814-77-9), Yellow No. 5 (Sunset Yellow FCF, CAS No. 2783-94-0), and Black No. 401 (Naphthol Blue Black, CAS No. 1064-48-8); xanthan pigments such as Red No. 223 (Tetrabromofluorescein, CAS No. 15086-94-9); triphenylmethane pigments such as Blue No. 1 (Brilliant Blue FCF, CAS No. 3844-45-9); and indigo pigments such as Blue No. 2 (Indigo Carmine, CAS No. 860-22-0). Pyrazoles such as Blue No. 4 (tartrazine, CAS No. 1934-21-0); and may be at least one selected from the group consisting of caramel and coffee extracts.

[0055] By adjusting the content ratio of the compound of the above chemical formula 1 and the pigment, the color development by the hair color composition can be variously controlled, and the pigment can be prevented from getting on the hands. The weight ratio of the pigment to the weight of the compound of the above chemical formula 1 can be 0.005 to 5. Specifically, the weight ratio of the pigment to the weight of the compound of the above chemical formula 1 can be 0.005 to 5, 0.01 to 4, 0.03 to 3, or 0.3 to 1. Preferably, the weight ratio of the pigment to the weight of the compound of the above chemical formula 1 can be 0.03 to 3. Within the above-described range, the compound of the above chemical formula 1 can maintain a bond to the hair by interacting with the hair while wrapping or supporting at least a portion of the pigment, and can prevent color transfer.

[0056] By controlling the content ratio of the surfactant and the pigment, the pigment can be prevented from sticking to the hands. The pigment can be prevented from sticking to the hands. The weight ratio of the pigment to the weight of the surfactant may be 0.00005 to 0.5. Specifically, the weight ratio of the pigment to the weight of the surfactant may be 0.00005 or more and 0.5 or less. Preferably, the weight ratio of the pigment to the weight of the surfactant may be 0.00005 or more and 0.3 or less. Within the above-described range, the surfactant can prevent aggregation of the compound of the chemical formula 1, and when a coating layer is formed on the hair, maintain a uniform distribution of the pigment to prevent detachment from the coating layer and maintain dyeing power.

[0057]

[0058] The above hair color composition can be colored by exposure to air or oxygen for 1 to 60 minutes, preferably 1 to 30 minutes, and most preferably 1 to 3 minutes. Therefore, the hair color composition uses oxygen in the air, which is harmless to the human body, as an oxidizing agent and does not require an oxidizing agent such as hydrogen peroxide, so that hair can be colored without damage to the hair or irritation to the scalp caused by hydrogen peroxide.

[0059] The above hair color composition may include, but is not limited to, water as a solvent. For example, the solvent may be distilled water, ethanol, a pH buffer solution, or a cosmetic base such as a shampoo base or treatment base. The solvent may be any solvent that can be used in commercially available cosmetics and does not cause damage upon contact with skin or hair.

[0060] The above hair color composition can be formulated as a 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 treatment agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair glaze, hair lacquer, hair moisturizer, hair mousse or hair spray.

[0061] For example, the hair color composition may be a hair shampoo, and the hair color composition may be a shampoo base, and the shampoo base may include purified water, sodium C14-16 olefin sulfonate, cocamidopropyl betaine, glycerin, sodium chloride, caffeine, centella asiatica leaf extract, 1,2-hexanediol, bifida ferment lysate, lactobacillus ferment lysate, lactococcus ferment lysate, sodium hyaluronate, beta-glucan, ceramide NP, panthenol, asiaticoside, asiatic acid, madecassic acid, niacinamide, maltodextrin, ethylhexylglycerin, hydrogenated lecithin, dipropylene glycol, citric acid, disodium EDTA, menthol, butylene glycol, guar hydroxypropyltrimonium chloride, sodium benzoate, May contain salicylic acid and fragrance.

[0062] One specific example of the present invention relates to a method for preparing a hair color composition, comprising the step of mixing a compound of the above chemical formula 1 and a solvent. The method for preparing the hair color composition is for preparing the hair color composition of the above-described specific example, and any overlapping parts are replaced with the description of the above-described specific example.

[0063] The step of mixing the compound of the above formula 1 and the solvent may be performed at a manufacturing temperature of 40 to 60°C. Specifically, the manufacturing temperature may be 40°C or more and 60°C or less, or 45°C or more and 55°C or less. Preferably, the manufacturing temperature may be 50°C or more and 60°C or less. If the temperature is less than 40°C, the compound of the above formula 1 is not dispersed and precipitates in the hair color composition, thereby reducing the dyeing property of the composition to hair. If the temperature exceeds 60°C, precipitation is formed due to hydrogen bonds and hydrophobic bonds between the compounds of the above formula 1.

[0064] One specific example of the present invention relates to a method for dyeing hair, comprising the step of contacting hair with a hair color composition according to the preceding specific example. The step of contacting hair with the hair color composition may be contacting the hair with the hair. The step may include, but is not limited to, immersing or immersing the hair in the composition, applying the composition to the hair using a hand or other tool such as a comb, or pouring or spraying the composition onto the hair.

[0065] The above hair dyeing method may further include a step of air-drying the hair that has been contacted with the hair color composition. The step may include, but is not limited to, leaving the hair in the air for 1 to 60 minutes, or drying it using a hair dryer for 1 to 5 minutes. Subsequently, the hair dyeing method may further include a step of washing the hair color composition remaining on the hair after dyeing the hair with water to remove it. Preferably, the hair dyeing method may repeat the step of contacting the hair with the composition and the step of air-drying the hair at predetermined time intervals. In this case, the hair treated with the composition can maintain a more distinct color for a longer period of time.

[0066]

[0067] Hereinafter, the present invention will be described in more detail through specific examples and experimental examples. The following examples and experimental examples are intended to illustrate the present invention, and the present invention is not limited by the following examples and experimental examples.

[0068] Examples 1 to 4, 6 to 17 and Comparative Examples 1, 2, 5, 6

[0069] Hair color compositions in the form of hair shampoos were prepared using Examples 1 to 4, 6 to 17 and Comparative Examples 1, 2, 5, and 6.

[0070] The composition shown in Table 1 below was added to a reactor exposed to nitrogen, and stirred at 50 to 100 rpm at 60°C for 5 minutes to prepare a hair color composition.

[0071] As the compound of chemical formula 1, commercially available hexahydroxybiphenyl (HDP; 1,1'-biphenyl-2,2',4,4',5,5'-hexanol, chemical formula 2 above) was used. Hair shampoo base: purified water, sodium C14-16 olefin sulfonate, cocamidopropyl betaine, glycerin, sodium chloride, caffeine, centella asiatica leaf extract, 1,2-hexanediol, bifida ferment lysate, lactobacillus ferment lysate, lactococcus ferment lysate, sodium hyaluronate, beta-glucan, ceramide NP, panthenol, asiaticoside, asiatic acid, madecassic acid, niacinamide, maltodextrin, ethylhexylglycerin, hydrogenated lecithin, dipropylene glycol, citric acid, disodium EDTA, menthol, butylene glycol, guar hydroxypropyltrimonium chloride, sodium benzoate, salicylic acid, fragrance, total 30g (4.425g of surfactant content per 30g) was used.

[0072] Comparative Example 3

[0073] In Comparative Example 3, a hair color composition in the form of a hair shampoo was prepared according to the composition in Table 1 below, but the hair color composition was prepared in the same manner as in Example 1, except that the preparation temperature was set to 25°C.

[0074] Example 5

[0075] In Example 5, a hair color composition in the form of a hair shampoo was prepared according to the composition in Table 1 below, and the hair color composition was prepared in the same manner as in Example 1, except that the preparation temperature was set to 40°C.

[0076] Comparative Example 4

[0077] In Comparative Example 4, a hair color composition in the form of a hair shampoo was prepared according to the composition in Table 1 below, but the hair color composition was prepared in the same manner as in Example 1, except that the preparation temperature was set to 80°C.

[0078] Classification HDP (g) Surfactant Shampoo Base Manufacturing Temperature (℃) Type Content (g) Total Weight (g) Surfactant Content (g) Comparative Example 10.003--304.42560 Example 10.03--304.42560 Example 20.1--304.42560 Example 30.2--304.42560 Example 40.3--304.42560 Comparative Example 20.6--304.42560 Comparative Example 30.1--304.42525 Example 50.1--304.42540 Comparative Example 40.1--304.42580 Example 60.1 Polyquaternium-671 304.42560 Example 70.1Miconium CTAC 291304.42560Example 80.1STAC 80KC1304.42560Example 90.1MITAINE LPB(N)1304.42560Example 100.1Mitaine CA-GF1304.42560Example 110.1Plantacare 20001304.42560Example 120.1Plantacare 8181304.42560Example 130.1ELOTANT Milcoside240HE1304.42560Example 140.1alginate1304.42560Example 150.1Keltrol F1304.42560Comparative Example 50.1Polyquaternium-670.06304.42560Example 160.1Polyquaternium-670.3304.42560Example 170.1Polyquaternium-672304.42560Comparative Example 60.1Polyquaternium-674304.42560

[0079]

[0080] Examples 18 to 21 and Comparative Examples 7 and 8

[0081] Hair color compositions in the form of hair shampoos were prepared using Examples 18 to 21 and Comparative Examples 7 and 8.

[0082] The composition shown in Table 2 below was added to a reactor exposed to nitrogen, and stirred at 60°C and 50 to 100 rpm for 5 minutes to prepare a hair color composition. The compound of Chemical Formula 1 and the shampoo base were the same as those in Example 1 (surfactant content 4.425 g per 30 g of shampoo base), and black No. 401 was used as the pigment.

[0083] Classification HDP (g) Surfactant pigment (g) Shampoo base Manufacturing temperature (℃) Type Content (g) Total weight (g) Surfactant content (g) Comparative example 70.003 Polyquaternium-6710.0003304.42560 Example 180.03 Polyquaternium-6710.003304.42560 Example 190.1 Polyquaternium-6710.03304.42560 Example 200.2 Polyquaternium-6710.1304.42560 Example 210.3 Polyquaternium-6710.3304.42560 Comparative example 80.6 Polyquaternium-6711304.42560

[0084]

[0085] Experimental Example 1. Evaluation of the stability of hair color compositions according to the content of HDP.

[0086] The appearance of the hair color composition in the form of a hair shampoo immediately after being manufactured according to Examples 1 to 4 and Comparative Examples 1 to 2 is shown in Fig. 1, and this was confirmed with the naked eye.

[0087] As shown in Fig. 1, in Comparative Example 1, which had a low HDP content, no color was observed due to HDP, and in Comparative Example 2, which had a high HDP content, a precipitate formed as HDP became supersaturated in the composition was observed.

[0088]

[0089] Experimental Example 2. Evaluation of the dyeability of hair color compositions according to the content of HDP.

[0090] The dyeing ability to hair was evaluated using hair color compositions in the form of hair shampoos manufactured according to Examples 1 to 4 and Comparative Examples 1 to 2.

[0091] Each bleached hair sample was shampooed and dried using the compositions of Examples 1 to 4 and Comparative Examples 1 to 2. Images of the hair after drying are shown in Fig. 2 (a). The colorimetric values ​​(L*) of the hair samples after treatment with the hair shampoo composition using a colorimeter are shown in Fig. 2 (b) and Table 3.

[0092] Colorimetric value (L*) Comparative example 153.3 Example 142.3 Example 237.8 Example 335.6 Example 432.1 Comparative example 241.8

[0093]

[0094] Referring to FIG. 2 and Table 3, it was confirmed that the dyeing property on bleached hair was low in Comparative Example 1, which had a low HDP content. In addition, it was confirmed that the dyeing property on bleached hair was low in Comparative Example 2, which had a high HDP content, because a uniform composition was not formed due to precipitation of HDP. In the compositions of Examples 1 to 4, it was confirmed that the dyeing property on hair increased in proportion to the increase in HDP content due to the uniform dispersion of HDP.

[0095]

[0096] Experimental Example 3. FT-IR Analysis of Hair Color Compositions According to Shampoo Manufacturing Temperature

[0097] The -OH bond wavenumber of the hair color compositions manufactured according to Examples 2 and 5 and Comparative Examples 3 and 4 was confirmed using FT-IR, and the results are shown in Table 4.

[0098] Classification-OH bond wavenumber (cm) -1 )Example 23401Comparative Example 33343Example 53360Comparative Example 43410

[0099]

[0100] Referring to Table 4, it was confirmed that the hydrogen bonding force between HDPs in the composition increases as the manufacturing temperature increases through the movement of the -OH bond as the manufacturing temperature increases.

[0101]

[0102] Experimental Example 4. Evaluation of the Stability of Hair Color Compositions According to Manufacturing Temperature

[0103] The appearance of the hair color composition in the form of a hair shampoo immediately after being manufactured according to Examples 2 and 5 and Comparative Examples 3 and 4 is shown in Fig. 3, and was confirmed with the naked eye.

[0104] As shown in Fig. 3, the hair color composition manufactured according to Comparative Example 3 (manufacturing temperature 25°C), which had a lower manufacturing temperature than Examples 2 (manufacturing temperature 60°C) and 5 (manufacturing temperature 40°C), was confirmed to have low dispersibility and fluidity of HDP. The hair color composition manufactured according to Comparative Example 4 (manufacturing temperature 80°C), which had a higher manufacturing temperature than Examples 2 (manufacturing temperature 60°C) and 5 (manufacturing temperature 40°C), was confirmed to have formed precipitates of HDP. These results are consistent with the tendency in Experimental Example 3 above that hydrogen bonds and hydrophobic bonds of HDP increase as the manufacturing temperature increases.

[0105]

[0106] Experimental Example 5. Evaluation of the dyeability of hair color compositions according to manufacturing temperature.

[0107] The dyeing properties of hair were evaluated using hair color compositions prepared according to Examples 2 and 5 and Comparative Examples 3 and 4.

[0108] Each bleached hair sample was shampooed and dried using the hair color compositions according to Examples 2 and 5 and Comparative Examples 3 and 4. Images of the hair after drying are shown in Fig. 4 (a). The colorimetric values ​​(L*) of the hair samples after treatment with the hair shampoo composition using a colorimeter are shown in Fig. 4 (b) and Table 5.

[0109] Colorimetric value (L*) Example 237.8 Comparative example 348.2 Example 539.5 Comparative example 445.8

[0110]

[0111] Referring to FIG. 4 and Table 5, it was confirmed that Comparative Example 3 (manufacturing temperature 25°C) had lower fluidity of HDP in the hair color composition compared to Example 2 (manufacturing temperature 60°C), resulting in lower dyeing properties on hair. Comparative Example 4 (manufacturing temperature 80°C) had higher manufacturing temperature compared to Example 5 (manufacturing temperature 60°C), resulting in increased hydrogen bonding and hydrophobic bonding, which resulted in precipitation of particles, and thus, it was confirmed that HDP in the composition was not uniform, resulting in lower dyeing properties on bleached hair.

[0112] In addition, it was confirmed that Example 2 (manufacturing temperature 60°C) showed increased hair dyeability due to an increase in hydrogen bonding of HDP compared to Example 5 (manufacturing temperature 25°C).

[0113]

[0114] Experimental Example 6. Stability Evaluation of Hair Color Compositions According to the Type of Surfactant

[0115] The appearance of the hair color composition in the form of a hair shampoo immediately after being manufactured according to Examples 2, 6 to 15 is shown in Fig. 5, and was confirmed with the naked eye.

[0116] Referring to FIG. 5, it was confirmed that HDP was uniformly dissolved in the compositions of Examples 2, 6 to 15.

[0117]

[0118] Experimental Example 7. Evaluation of the Dyeing Properties of Hair Color Compositions According to the Type of Surfactant

[0119] The dyeing properties of hair were evaluated using hair color compositions prepared according to Examples 2, 6 to 15.

[0120] Each bleached hair sample was shampooed and dried using a hair color composition according to Examples 2, 6 to 15. Images of the hair after drying are shown in Fig. 6. The colorimetric values ​​(L*) of the hair samples after treatment with the hair shampoo composition using a colorimeter are shown in Fig. 7 and Table 6.

[0121] Colorimetric value (L*) Example 239.8 Example 633.8 Example 735.7 Example 835.9 Example 936.1 Example 1035.9 Example 1141.1 Example 1241.5 Example 1341.3 Example 1442.0 Example 1541.8

[0122]

[0123] Referring to FIG. 7 and Table 6, it was confirmed that Examples 6 to 10 using cationic additives increased the solubility of HDP and thus the dyeability of HDP compared to Examples 2 and 11 to 15.

[0124]

[0125] Experimental Example 8. Evaluation of the Stability of Hair Color Compositions According to the Content of Surfactant

[0126] The appearance of the hair color composition in the form of a hair shampoo immediately after being manufactured according to Examples 2, 6, 16, 17 and Comparative Examples 5 and 6 is shown in Fig. 8, and was confirmed with the naked eye.

[0127] Referring to FIG. 8, Comparative Example 6 confirmed that the formulation clumped due to increased bonding between HDP and surfactant as compared to Examples 2, 6, and 16 to 17 due to increased surfactant content.

[0128]

[0129] Experimental Example 9. Evaluation of the Dyeing Properties of Hair Color Compositions According to the Content of Surfactant

[0130] The dyeing properties for hair were evaluated using hair color compositions manufactured according to Examples 2, 6, 16, and 17 and Comparative Examples 5 and 6.

[0131] Each bleached hair sample was shampooed and dried using the hair color compositions according to Examples 2, 6, 16, and 17 and Comparative Examples 5 and 6. The images of the hair after each drying are shown in Fig. 9 (a). The colorimetric values ​​(L*) of the hair samples after treatment with the hair color composition using a colorimeter are shown in Fig. 9 (b) and Table 7.

[0132] Colorimetric value (L*) Example 239.8 Example 633.8 Comparative example 539.6 Example 1637.4 Example 1733.2 Comparative example 644.8

[0133]

[0134] Referring to Fig. 9 and Table 7, Comparative Example 5 added additives compared to Example 2, but it was confirmed that there was no difference in the dyeability of the hair color composition due to the small amount of additives added. Examples 16, 6, and 17 confirmed that the dyeability gradually increased in that order because the solubility and inducibility of HDP increased as the additive content increased.

[0135] In addition, Comparative Example 6 confirmed that the formulation was clumped together and the hair shampoo composition was not uniform, resulting in poor dyeing properties.

[0136]

[0137] Experimental Example 10. Stability Evaluation of Hair Color Compositions According to Pigment Content

[0138] The appearance of the hair color composition in the form of a hair shampoo immediately after being manufactured according to Examples 2, 18 to 21 and Comparative Examples 7 and 8 is shown in Fig. 10, and was confirmed with the naked eye.

[0139] Each hair color composition was applied to the surface of a plastic plate and the palm of the hand, then washed with water, and the coloring on the surface was confirmed, as shown in Fig. 10.

[0140] Referring to Fig. 10, it was confirmed that the pigment was well dispersed in each composition, but in Comparative Example 8, the pigment content was high, and it was confirmed that the pigment that was not contained in the HDP colored the plastic plate and the palm.

[0141]

[0142] Experimental Example 11. Evaluation of the dyeability of hair color compositions according to pigment content.

[0143] The hair color compositions of hair shampoo formulations manufactured according to Examples 2, 18 to 21 and Comparative Examples 7 and 8 were used to evaluate the dyeing properties for hair.

[0144] Each bleached hair sample was shampooed and dried using the hair color compositions according to Examples 2, 18 to 21 and Comparative Examples 7 and 8. The images of the hair after drying are shown in Fig. 11 (a). The colorimetric values ​​(L*) of the hair samples after treatment with the hair color composition using a colorimeter are shown in Fig. 11 (b) and Table 8.

[0145] Colorimetric value (L*) Example 239.8 Comparative example 739.5 Example 1837.8 Example 1933.7 Example 2029.4 Example 2125.1 Comparative example 824.8

[0146]

[0147] Referring to Fig. 11 and Table 8, it was confirmed that as the pigment content increased, not only HDP but also the inherent color of the pigment was expressed and the dyeability increased. However, in Comparative Example 8 compared to Example 21, the pigment content was high, so the pigment that could not combine with HDP was not dyed into the hair, and thus the dyeability did not increase even if the pigment content increased.

Claims

1. A hair color composition comprising a compound of the following chemical formula 1: [Chemical Formula 1] Among the foods, R1 is hydrogen, hydroxyl or carboxyl group, R2 and R3 are independently hydrogen, carboxyl group, C1-C 10 Alkyl group, C1-C 10 Haloalkyl group, C1-C 10 Alkoxy group, C1-C 10 It is a haloalkoxy group, an amine group, or a C1-C4 aminoalkyl group.

2. In paragraph 1, The above R1 is a hydroxy group, A hair color composition wherein R2 and R3 are each hydrogen.

3. In paragraph 1, A hair color composition comprising 0.01 to 1.95 wt% of the compound of the chemical formula 1 based on the total weight of the hair color composition.

4. In paragraph 1, A hair color composition further comprising 0.2 to 21 wt% of a surfactant based on the total weight of the hair color composition.

5. In paragraph 4, A hair color composition, wherein the surfactant is at least one selected from the group consisting of cationic surfactants, anionic surfactants, nonionic surfactants, and amphoteric surfactants.

6. In paragraph 4, Contains more pigments, A hair color composition wherein the weight ratio of the pigment to the weight of the surfactant is 0.00005 to 0.

5.

7. In paragraph 1, The above hair color composition is formulated as a 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 treatment agent, hair dye, hair waving agent, hair bleaching agent, hair gel, hair glaze, hair lacquer, hair moisturizer, hair mousse or hair spray.

Images