JPH0826967A - Cosmetic containing chlorogenic acid or its derivative - Google Patents

Abstract

PURPOSE:To obtain the cosmetic containing one or more kinds of chlorogenic acid and/or its derivatives and useful for beautifully whitening skin, preventing the aging of the skin, and protecting hair. CONSTITUTION:In the cosmetic, the lipid peroxide production-inhibiting action, UV light-absorbing action and melanin production-inhibiting action of the chlorogenic acid and/or its derivatives are applied to the cosmetic. The cosmetic is utilized in the fields of medicines, quasi-drugs and cosmetics, and can concretely be utilized in the forms of lotions, emulsions, creams (including ointments), oils, packs, soaps (including medicinal soaps), body soaps, bath agents, shampoos, rinses, hair tonics, hair sprays, etc.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to cosmetics containing one or more chlorogenic acid and / or chlorogenic acid derivatives. It can be used as various cosmetic compositions in the fields of pharmaceuticals / quasi-drugs or cosmetics (various preparations used for humans and other animals). Specifically, lotions, emulsions, creams ( Applications include ointments), oils, packs, soaps (including medicated soaps), body soaps, bath agents, shampoos, rinses, hair nicks, hair sprays, etc.

[0002]

2. Description of the Related Art The skin and hair cover the surface of the living body and protect the living body from various factors such as bad environment such as ultraviolet rays, bacteria and dust. In other words, the skin and hair are those environments. Constantly exposed to the factors and hurt.

Therefore, research has been conducted for a long time for cosmetics and the like that protect skin and hair from environmental factors that have an adverse effect on the inside and outside of the body, and that promote regeneration of damaged skin and hair. Furthermore, in recent years, research aiming at beauty has been actively conducted, not only for the purpose of health, but also for the background of the psychology of always wanting to be beautiful.

[0004] In addition, various kinds of pharmaceuticals, quasi drugs, and cosmetics for the purpose of removing / eliminating factors that have an adverse effect on the inside and outside of the living body are currently on the market. Among them, a lipid peroxide production inhibitory action, an ultraviolet ray absorbing action, a melanin production inhibitory action and the like are known.

[0005] For example, the lipid peroxide production inhibitory action is an action of preventing lipids (oils) existing in the living body from being oxidized. For example, lipid peroxides formed by the oxidation of lipids impair the function of cell membranes in the body, inactivate various enzymes, denature biological proteins, etc., and adversely affect biological tissues. These are also considered to lead to diseases such as aging and cancerous changes, and in recent years, suppression of this lipid peroxidation has been regarded as important in dermatology.

Further, the ultraviolet rays of the sun rays are
Although it is useful in health and hygiene such as vitamin D synthesis, sterilization and disinfection, it also has harmful effects such as sunburn, suntan, skin aging, and skin cancer.

[0007] In a word, even if it is called ultraviolet rays, due to the difference in biological action, it is in the UV-C region of 290 nm or less, 2
90-320 nm UV-B region, 320-400 nm
It is divided into 3 regions of UV-A region, and UV-C region is an ultraviolet ray that has a strong effect on living organisms and is highly carcinogenic, but it does not reach the ground because it is almost absorbed by the ozone layer in the stratosphere. However, the decrease of the ozone layer has become a problem in recent years, and there is a concern that skin cancer will increase. UV rays in the UV-B and A areas also promote sunburn (acute inflammation), suntan (pigmentation), skin aging, skin cancer, etc., but when UV rays are applied to the skin, UV-
B penetrates the stratum corneum and epidermis, erythema appears after about 3 to 6 hours, and reaches a peak after 24 hours. Then, in 4 to 15 days, the erythema gradually shifts to blackening, which occurs because the melanocytes are activated by the inflammatory reaction by UV-B and the melanin production amount increases. In addition, keratinization progresses in the damaged epidermal tissue, causing rough skin due to a decrease in the water content of the stratum corneum.

[0008] Further, it is said that UV-A reaches the dermis layer, causes immediate blackening, and disappears in a short time. This is considered to be because existing melanin is temporarily oxidized and blackened. . With continuous exposure, delayed blackening occurs, and although erythema does not appear, melanocyte activation is remarkable and the degree of blackening becomes strong. Furthermore, since the skin permeability is high, the dermal tissue is severely damaged, the elasticity of the skin is lost, deep wrinkles are caused, and the color becomes dark brown. It is also necessary to protect the area, UV-A area).

Further, there are various enzymes involved in oxidation and reduction in the living body. Among them, as one of the causes of skin darkening, for example, tyrosinase enzyme is raised, and
Several metabolic mechanisms are considered in relation to the change (phenomenon) of pigments in plants. One of them is the activation of tyrosinase enzyme in melanocytes to oxidize tyrosine and convert it into dopaquinone. However, it is further known that it is oxidized to dopachrome, 5,6-dihydroxyindole, which is polymerized and finally produces black melanin. Therefore, there is a demand for a substance that prevents abnormal blackening of the skin based on such a biochemical mechanism. There is also a need for a substance that inhibits the activation of tyrosinase, which is also involved in the formation of melanin pigment.

On the other hand, chlorogenic acid is said to have been industrially isolated from green coffee beans for the first time, and it is known that Robusta seeds have a higher chlorogenic acid content than Arabica seeds. ing. In addition, chlorogenic acid is widely present in other plants and is contained in fruits of many dicotyledons, leaves, and examples of plants containing chlorogenic acid are tobacco leaves, pear leaves, apple pulp, sweet potato, mulberry,
Tea etc. are known.

Incidentally, a report on the application of chlorogenic acid to the industrial field has been recently made, and the publication is 1: JP-A-57-83250 (Sugar and starch syrup as a method for producing candy). Chlorogenic acid is added to the main ingredient candy to prevent browning of the candy),
2: JP-A-57-115147 (chlorogenic acid and other substances are added to foods and drinks containing saccharides to prevent browning due to caramelization of sugars).
17566 (Similarly, chlorogenic acid and other substances are added to the paprika pigment to prevent the fading of the paprika pigment over time) 4: JP-A-58-138347 (natural edible antioxidant substance of enzymatically decomposed coffee beans) 5: JP-A-60
-192555 (Anti-allergic food containing chlorogenic acid as an essential component), 6: JP-A-62-111671
(Natural anti-acid agent for hot water extract of green coffee beans), 7:
Table 63-502349 (Isolated chlorogenic acid is administered before or during the administration of food, beverage or drug that damages the mucous membrane of the stomach or duodenum or promotes gastric acid secretion,
Protecting gastric mucosa against progression of ulcer) 8: JP-A-02-
100600 (Mulberry / tea extract is added to food, this food is wrapped in wrapping paper having far-infrared radiation and ethylene gas adsorption, and stored at low temperature to maintain long-term freshness and browning of food surface. Prevention), 9: JP-A-04-
27374 (containing chlorogenic acid and vitamin C and the like in food and drink to suppress the reduction and change of aroma and flavor during the processing and storage of food and drink and the generation of off-flavors), 10: JP-A-04-04
-283501 (Cut flower freshness-retaining agent), 11: JP-A-06-06
-9603 (stabilization method of vitamin C) and the like have been reported.

[0012]

As described above, most of the utilization of chlorogenic acid is to prevent fading and browning of foods and drinks, to suppress off-flavors, to protect mucous membranes of stomach and duodenum, and vitamin C. It is intended to stabilize the drug, and the action and effect can be obtained by oral administration. On the other hand, in the field of cosmetics, none has been effectively used. Therefore, the present inventors have made extensive efforts to study and pursue the unique novel and useful use of chlorogenic acid and its action.

[0013]

In view of the above circumstances, the present inventors have investigated chlorogenic acid or its derivatives and have the above-mentioned lipid peroxide production suppressing action, ultraviolet absorbing action, and melanin production inhibiting action. It was confirmed that it was very effective to apply to cosmetics, and the present invention was completed. The process leading to the present invention will be described below.

The chlorogenic acid of the present invention means mono- and dicaffeoylquinic acid and a mixture thereof, preferably 3-, 4- and 5-caffeoylquinic acid or a mixture thereof, and chlorogenic acid is Free acid,
Or, in the form of physiologically acceptable derivatives, specifically, salts formed by metals such as sodium, potassium, magnesium, calcium, zinc, barium, and aluminum, ammonium, alcohols, fatty acids, alkylhalogenides, etc. An ester such as an alkyl ester obtained by the reaction of and a salt thereof,
Further, a phosphorylated compound introduced with a phosphoric acid group, a sulfated compound introduced with a sulfuric acid group, and further C _{2 to} C ₄ such as ethylene glycol, propylene glycol and butylene glycol
Alkyl ether derivatives obtained by reaction with alkylene oxides having carbon chains of the order of 4; such as glycidyltrialkylammonium halogenides
It can be used in the form of a quaternary alkylamine derivative and a salt thereof which are formed by a reaction with a substrate having a primary amine in the molecule.

The chlorogenic acid or chlorogenic acid derivative of the present invention may be a general commercial product (made by Janssen, etc.), or a chlorogenic acid derivative substance obtained by a known chemical synthesis method can be used. Yes, it does not necessarily have to be a pure product. Further, chlorogenic acid or chlorogenic acid derivative can be used as they are, or in the state of using an organic solvent, water or hot water as a solvent, or if necessary, dissolved in an organic solvent or a mixed solvent with water, It can also be used in a state in which organic solvent extraction and water extraction are combined. As the organic solvent, methanol, ethanol, n-
Butanol, acetone, chloroform, ethyl acetate, n
-Hexane, 1,3-butylene glycol, propylene glycol and the like can be used, and the form can be a solution, paste, gel or powder.

Further, the substance obtained by the chemical synthesis method of chlorogenic acid or a chlorogenic acid derivative can be used as it is in many cases, but if necessary, it is deodorized and decolorized within a range that does not affect its efficacy. Purification treatment such as the above may be added. In addition, as a purification processing means such as deodorization and decolorization,
An activated carbon column or the like may be used, and a generally applied ordinary means may be arbitrarily selected.

The chlorogenic acid or chlorogenic acid derivative of the present invention can be used as it is, but the amount of the chlorogenic acid or chlorogenic acid derivative to be blended as a cosmetic varies slightly depending on the kind of the cosmetic and the expected degree of action. Usually, 0.001% by weight or more, preferably 0.1 to 5.0% (hereinafter, represented by% by weight) is good. If the blending amount is less than 0.001%, the effect cannot be expected sufficiently.

The cosmetics containing the chlorogenic acid or the chlorogenic acid derivative of the present invention include various components generally used in cosmetics, pharmaceuticals, quasi-drugs, etc. within a range not impairing the effects of the present invention. , Oils (animal and vegetable oils, mineral oils, ester oils, wax oils, silicone oils, higher alcohols, phospholipids, fatty acids, etc.), surfactants (anionic, cationic, amphoteric or nonionic surfactants) ),
Vitamin (vitamin A group, vitamin B group, folic acid, nicotinic acid, pantothenic acid, biotin, vitamin C
Group, vitamin D group, vitamin E group, other ferulic acid,
γ-oryzanol, etc., ultraviolet absorber (p-aminobenzoic acid, anthranil, salicylic acid, coumarin, benzotriazole, tetrazole, imidazoline, pyrimidine, dioxane, furan, pyrone, camphor, nucleic acid,
Allantoin and derivatives thereof, amino acid compounds,
Shikonin, baicalin, baicalein, berberine, etc.), antioxidants (stearate, nordihydroguaselethenoic acid, dibutylhydroxytoluene, butylhydroxyanisole, parahydroxyanisole, propyl gallate, sesamol, sesamolin, gossypol, etc.), increase Sticky agent (hydroxyethyl cellulose, ethyl cellulose, carboxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, hydroxypropyl cellulose, nitrocellulose, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, polyvinyl methacrylate, polyacrylate, carboxyvinyl Polymer, gum arabic, gum tragacanth, agar, casein, dextrin, ze Tin, pectin, starch, alginic acid and its salts), moisturizers (propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycerin, chondroitin sulfate and its salts, hyaluronic acid and its salts, sodium lactate, etc.) and others , Lower alcohol, polyhydric alcohol, water-soluble polymer,
pH adjuster, antiseptic / antifungal agent, colorant, fragrance, cooling agent,
Stabilizers, animal and plant extracts, animal and plant proteins and their degradation products, animal and plant polysaccharides and their degradation products, animal and plant glycoproteins and their degradation products, microbial culture metabolic components, blood flow promotion Agent, anti-inflammatory agent, anti-inflammatory agent, anti-allergic agent, cell activating agent, amino acid and its salt, keratolytic agent, astringent agent, wound healing agent, foaming agent, oral agent, deodorant / deodorant agent,
It can also be used in combination.

The dosage form of the cosmetic composition containing the chlorogenic acid or chlorogenic acid derivative of the present invention is arbitrary, and may be prepared by a conventional method, for example, a lotion, cream, ointment, lotion, emulsion, pack, It may be in the form of oil, soap (including medicated soap), face wash, fragrance, cologne, bath agent, shampoo, conditioner, hair tonic, hair spray and the like. In addition, various forms of oral drugs, as well as non-woven fabrics such as sanitary cotton and wet tissue,
It can also be used as a composition for oral cavity caused by stomatitis and the like.

Further, the form of the cosmetic is arbitrary, and it can be used in the form of solution, cream, paste, gel, gel, foam, solid or powder.

The production examples (dissolution examples) will be disclosed and described in more detail below, but the method shown by the following is used in the confirmation test for the action and the like described later, and is not limited to this. .

Dissolution Example 1: (Chlorogenic acid solution) 20 mg of 1.6 mg of chlorogenic acid (Jansen) powder was added.
% Ethanol solution and add 100 ml
And

Dissolution Example 2: (Potassium Chlorogenate Solution) 1.6 mg of potassium chlorogenate powder was added to a 20% aqueous ethanol solution to make a solution of 100 ml.

Dissolution Example 3: (Chlorogenic acid fatty acid ester solution) Chlorogenic acid was dispersed in a mixed solution of dimethylformamide and pyridine, and a fatty acid halogenide or a fatty acid anhydride was added thereto and reacted at about 60 ° C for about 2 hours. rear,
The reaction product is separated, washed with ethanol or the like, and then dried to obtain a chlorogenic acid fatty acid ester. In addition, 1.6 mg of the obtained chlorogenic acid fatty acid ester was added to a 60% 1,3-butylene glycol aqueous solution, and the solution was dissolved to 100 m.
l.

Dissolution Example 4: (Chlorogenic Acid Sulfate Solution) Chlorogenic acid was dissolved in a mixture of dimethyl sulfoxide and pyridine, and chlorosulfonic acid was slowly added dropwise.
After reacting at about 85 ° C. for about 3 hours, the product is purified using a basic ion exchange resin (Amberlite IR-20: manufactured by Organo) to obtain a chlorogenic acid sulfate. In addition, the obtained chlorogenic acid sulfate 1.6 mg was added with 20% 1,3-butylene glycol aqueous solution, and the solution was made up to 100 ml.

Dissolution Example 5: (Hydroxypropyl chlorogenic acid solution) Chlorogenic acid was dissolved in dimethylsulfoxide, propylene oxide was added, and etherification reaction was carried out at about 20 to 80 ° C for several hours, followed by concentration under reduced pressure to give hydroxy. Propyl chlorogenic acid is obtained. The obtained hydroxypropylchlorogenic acid (1.6 mg) was added with a 20% 1,3-butylene glycol aqueous solution, and the resulting solution was made up to 100 ml.

Dissolution Example 6: (Chlorogenic acid quaternary alkylamine derivative solution) Glycidyltrimethylammonium chloride was added dropwise to the chlorogenic acid solution to carry out the substitution reaction, and the pH was adjusted to about 7.0 with 1N hydrochloric acid, and the like. A certain amount of n-butanol is added for liquid separation, the n-butanol layer is separated and concentrated under reduced pressure to obtain chlorotrimethylammonium glycidyl chlorogenic acid. In addition, 1.6 mg of the obtained chlorotrimethyl ammonium glycidyl chlorogenic acid was added to 60% 1,3-
Add a butylene glycol aqueous solution and add 10
The volume was 0 ml.

In the production (reaction) related to the chlorogenic acid derivative, by appropriately adjusting the addition amount, type, reaction time, reaction temperature, pH and the like of the desired reactant,
Since the average substitution degree can be controlled, the substitution degree for the chlorogenic acid derivative is not particularly limited.

[0031]

[Examples] Examples will be disclosed and described in more detail below, but the method shown below was used in the confirmation test for the action and the like described later, and is not limited thereto.

Example 1 Lipid Peroxide Production Inhibition Test TBA Method (Analytical, Biochemistry Vol.95, p.351-358, 1)
979), the inhibitory effect of linolenic acid on peroxide generation was examined and measured by the following test method.

[Test Method] 0.1% linolenic acid was added to 0.8% sodium lauryl sulfate aqueous solution and dissolved, and 3.9 ml of this solution was placed in a 10 ml transparent glass screw bottle. 0.1 ml of the sample solution was added to this, and ultraviolet rays (Toshiba: 3 FL-20SE lamps and 3 FL-20SBL lamps were lit in parallel at a distance of 15 cm) were irradiated for 1 hour, and 1 ml of this solution was taken. 1 ml of a mixture of 0.67% thiobarbituric acid aqueous solution and 15% acetic acid aqueous solution (pH 3.5),
Add 20 μl of 4.5% dibutyl hydroxytoluene,
Heat at 95 ° C. for 1 hour. After cooling, add 4 ml of methanol: n-butanol (15:85), shake well, and centrifuge. Next, the absorbance at 534 nm of this n-butanol layer was measured and used as the amount of lipid peroxide. The amount of lipid peroxide when a sample is added and irradiated with ultraviolet light is a, the amount of lipid peroxide when a sample is added and not irradiated with ultraviolet light is b, and ethanol or 1,3-butylene glycol is used instead of the sample. Suppression of lipid peroxide production as lipid peroxide amount a'when UV radiation is added and ultraviolet rays are added, and ethanol peroxide or 1,3-butylene glycol is added instead of the sample and UV radiation is not irradiated. The rate was calculated by the equation 1. "Preparation of sample" As a sample, the above-mentioned dissolution examples 1 to
As a control, a solution prepared by dissolving 1 g of α-tocopherol (manufactured by Kishida Chemical Co., Ltd.) in 100 ml of an ethanol solution was used.

[0034]

[Equation 1]

[0035]

[Table 1]

[Test Results] As shown in Table 1, it was confirmed that the chlorogenic acid or the chlorogenic acid derivative of the present invention exhibited a stronger lipid peroxide production suppressing action than the tocopherol solution of Comparative Example 1.

Example 2 Ultraviolet Absorption Action Test "Test Method" Using a spectrophotometer (1 cm layer length: quartz cell), the absorbance of ultraviolet light was measured by the absorbance measurement method, and the result was taken as the ultraviolet absorption action. The sample used was the dissolution example 1 of Example 1, and the same concentration of paraaminobenzoic acid (PAB) was used as a control.
A) was used.

[0038]

[Figure 1]

[Test Results] The results are shown in FIG. 1, in which chlorogenic acid was compared with para-aminobenzoic acid in the ultraviolet wavelength range (2
It was confirmed that the absorption of 80 to 350 nm) was dominant. Also, the chlorogenic acid derivative was confirmed to have almost the same UV absorbance.

Example 3: Tyrosinase activity inhibitory activity test "Test method" tyrosine solution (L-tyrosine 0.3 mg /
1.0 ml, Macklevine buffer (pH 6.
5) Mix 2.0 ml and 0.2 ml of the sample solution,
After leaving for about 10 minutes in a 37 ° C constant temperature bath, add a tyrosinase solution (derived from mushrooms, 2500 unit
/ Ml) 0.1 ml was added, and then the absorbance at 475 nm was measured (A). After that, this reaction solution was allowed to stand for 20 minutes in a 37 ° C. constant temperature bath, and then the absorbance at 475 nm was similarly measured (A). '). At the same time, as a blank, instead of the sample solution, purified water was used to measure the absorbances (a) and (a ′) in the same manner, and the tyrosinase activity inhibition rate was calculated by Equation 2. The samples used were the dissolution examples 1 to 6 of Example 1 and the comparative example 1.

[0041]

[Equation 2]

[0042]

[Table 2]

"Test Results" As shown in Table 2, it was confirmed that the chlorogenic acid or chlorogenic acid derivative of the present invention has a stronger tyrosinase activity inhibitory action than the tocopherol solution of Comparative Example 1.

Example 4: Melanin production inhibitory action test Referring to the method of "Test Method", 1) (Cosmetics Technical Journal 26 (1), 8, 1992), C57BL mice (8W♀) were exposed to ultraviolet rays (made by Toshiba). : UV FL20-SE lamp) 15.2 mJ / cm ² , 1 day
Irradiation was repeated once for 3 days. One week after the final irradiation day, the auricle was collected, the cartilage was removed, and the skin of the outer ear was dipped in a 2N-sodium bromide solution. Then, the epidermis was peeled off from the direct skin, and the epidermis was immersed in a 0.1% L-dopa solution (0.1 M phosphate buffer, pH 7.2) for dopa staining. The samples (dissolution examples 1 to 6) were added to the dopa solution in Table 3
The purified water (dissolving examples 1-2, 4-5) and the mixed solution of the purified water and the surfactant (dissolving examples 3, 6) used at the time of drug preparation were the same. The number of melanocytes in a certain portion (5 mm ² ) was measured with a microscope and evaluated by the number of cells per 1 mm ² , and the results are shown in Table 3.

[0045]

[Table 3]

"Test Results" The results are shown in Table 3. The chlorogenic acid or chlorogenic acid derivative of the present invention was found to induce melanocytes in the epidermis of colored mouse auricles, which were activated by ultraviolet light,
When specifically stained with dopa fluid, a decrease in the number of melanocytes (melanocytes) was observed predominantly.
It was confirmed that it has a melanin production inhibitory action.

Example 5: Tensile strength test "Test method and evaluation method" 50 untreated human hairs were rinsed with warm water, 50 untreated human hairs were allowed to soak into the sample solution for 10 minutes, and then air-dried well. , UV (Toshiba: FL-20SE
Three lamps and three FL-20SBL lamps were arranged in parallel and irradiated at a distance of 15 cm) for 1 hour, finally rinsed with warm water, rinsed off, and dried for 10 minutes to measure tensile strength.
In the measurement, untreated human hair having a uniform length of about 10 cm was pulled one by one at a speed of 2 cm / min, and the load at break was determined. The samples used were the dissolution examples 1 to 6 and the comparative example 1 of Example 1, and the tensile strength was measured using a tensilon meter (manufactured by Toyo Baldwin) under the conditions of temperature 20 ° C. and humidity 60%. . Numerical values in the table represent average values, and the results are shown in Table 4.

[0048]

[Table 4]

[Test Results] The results are shown in Table 4. Human hair treated with the chlorogenic acid or chlorogenic acid derivative of the present invention was compared with human hair treated with Comparative Example 1 (α-tocopherol solution). Good results were obtained with a high breaking load and a protective effect of suppressing the decrease in the tensile strength of the hair due to ultraviolet rays.

Example 6: Persistence of water retention effect "Test method and evaluation method" Human hair (weight: 4 g, length: 10 c)
To m), apply 5 g of the hair rinse shown in Table 5 below, rinse with warm water, rinse with air for 10 minutes, store at constant humidity, and measure the water content immediately after and after 3 hours to obtain the change rate. The sustainability of the effect was evaluated. The evaluation method is
The results were shown in Table 5 by performing a 3-level evaluation of -C. Evaluation A: Change rate of less than 50%. Evaluation B: Change rate of 50% or more and less than 70%. Evaluation C: Change rate of 70% or more.

Example 7: Feeling sensory test (smoothness / moistness / combability) "Testing method and evaluation method" 70 female panelists, 1 in each section
The hair rinses of the present invention product and the comparative product shown in Table 5 below were handed over to each of 5 groups of 0 persons and washed with commercial shampoo, rinsed well with warm water and rinsed well, and then actually applied directly to the hair. Was applied and thoroughly permeated, rinsed with warm water, rinsed off, and sensory-evaluated for smoothness after air-drying, moist feeling, and combability. In addition, the evaluation method was performed by the following three-stage evaluation of 1 to 3, and the average value of 10 persons was measured, and the results are shown in Table 5. Evaluation 3: Good. Evaluation 2: Normal. Evaluation 1: Bad.

Example 8: Sensory sensation test (luster of hair) "Test method and evaluation method" 70 female panelists, 1 in each section
The hair rinses of the present invention product and the comparative product shown in Table 5 below were handed over to each of 5 groups of 0 persons and washed with commercial shampoo, rinsed well with warm water and rinsed well, and then actually applied directly to the hair. Was applied, thoroughly permeated, rinsed with warm water, rinsed, and air-dried, and a sensory evaluation was made on the gloss of the hair. In addition, the evaluation method was performed by the following three-stage evaluation of 1 to 3, and the average value of 10 persons was measured, and the results are shown in Table 5. Evaluation 3: Shiny. Evaluation 2: There is a gloss. Evaluation 1: Matte.

"Test Results" Hair rinses having the composition shown in Table 5 were prepared, and the durability of the water retention effect of the hair, the smoothness of the hair, the moist feeling, the combability, and the gloss of the hair were evaluated together with the comparative product. The results are shown in Table 5, and the products of the present invention 1 to 6
Is the tensile strength, the retention of moisture on the hair, the smoothness of the hair, the moist feeling, the comb-through, the gloss, both of which are compared to the comparative product.
Overall, good results were obtained.

[0054]

[Table 5]

Example 9: Use effect test "Test method and evaluation method" 70 adult male and female panelists were divided into 7 groups with 10 groups each, and the sunscreen emulsions of the present invention and comparative products shown in Table 6 below were prepared. 30g handed every day,
Before going out, I took an appropriate amount by hand, applied it on my face, and conducted a continuous use effect test for one month.
When the face was washed by sweating, an appropriate amount was taken and applied each time. The evaluation method was based on the following criteria. "Skin aging prevention effect" Effective: The skin's suppleness and gloss were improved. Slightly effective: The skin's elasticity and gloss were slightly improved. Ineffective: No change from before use. "Effect of rough skin improvement" Effective: The roughness and roughness of the skin were improved. Slightly effective: The bulkiness and roughness of the skin are slightly improved. Ineffective: No change from before use. "Skin color improvement effect" Effective: The skin color was improved to white. Slightly effective: The skin color was improved to be slightly white. Ineffective: No change from before use. The numerical values in Table 7 represent the number of people, and the results are shown in Table 7.

[0056]

[Table 6]

[Test Results] As shown in Table 7, the products 1 to 6 of the present invention are improved in prevention of skin aging, rough skin, and complexion.
Compared to the comparative product, overall improvement and good results were obtained, confirming that it was effective.

[0058]

[Table 7]

Example 10: Safety test [Primary skin irritation test] Chlorogenic acid powder and dissolution example
20% of 1 g of the chlorogenic acid derivative obtained in 2, 4 to 5
Dissolved in 100 ml of 1,3-butylene glycol aqueous solution
Liquid, chlorogenic acid derivative obtained in dissolution examples 3 and 6
1 g of 60% 1,3-butylene glycol aqueous solution 100
Rabbits with hair removed from a solution dissolved in ml (3 animals per group, body weight
About 3,800 g) was applied to the skin. Judgment is 24, 48, 7 after pasting
Marked erythema and edema by scoring method of primary irritation every 2 hours
Went as. As a result, in all animals,
Etc., erythema and edema were not observed, and it was determined to be negative. [Skin cumulative irritation test] Similarly, chlorogenic acid powder and
1 g of the chlorogenic acid derivative obtained in Dissolution Example 2 and 4 to 5
To 100 ml of 20% 1,3-butylene glycol aqueous solution
Dissolved liquid or chlorogenic acid obtained in Dissolution Examples 3 and 6
Derivative 1g 60% 1,3-butylene glycol aqueous solution
Removes hair from the flank of a solution dissolved in 100 ml (2 x 4 cm²)
Hartley guinea pig (female, 5 per group, weight 320)
(about g) once a day, 5 times a week, 0.5 ml / per animal
Was applied. Apply for 4 weeks, and remove hair at the end of each week.
It was done on the last application day. Judgment is made on the first day after the last day of each week
Erythema and edema were used as indices by the stimulus scoring method.
Was. As a result, 1 to 4 weeks after application in all animals
No erythema or edema was observed over the eyes, and the result was negative.
Was. [Acute toxicity test] Similarly, chlorogenic acid powder and dissolution examples
2 hours before test, the chlorogenic acid derivative obtained in 2-6
2,000 to fasted ddy mice (5 mice per group, weight 30g)
Orally administered in mg / kg dose, and observed the onset and degree of toxicity symptoms over time
I observed it. As a result, 14 days in all mice
No abnormalities were observed during the period, and there were no abnormalities in the autopsy results. LD
_{Five 0} Was determined to be 2,000 mg / kg or more.

The use of the present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples and is applicable to various cosmetics, pharmaceuticals, quasi-drugs and the like. It can be contained and compounded before use. In addition, each Example may be manufactured by a conventional method for manufacturing each product, and only the compounding amount is shown.

Example 11: Cold Cream Weight% 1. White beeswax 11.0 2. Liquid paraffin 22.0 3. Lanolin 10.0 4. Almond oil 15.0 5. Borax 0.5 6. Dissolution Example 1 (chlorophosphoric acid solution) 1.5 7. Preservative proper amount 8. Perfume proper amount 9. Residue of purified water 100

Example 12: Cream Weight% 1. Squalane 20.0 2. Beeswax 5.0 3. Refined jojoba oil 5.0 4. Glycerin monostearate 2.0 5. Polyoxyethylene (20) sorbitan monostearate 2.0 6. Glycerin 5.0 7. Dissolution Example 2 (potassium chloroformate solution) 2.0 8. Preservative proper amount 9. Suitable amount of perfume 10. Residue of purified water 100

Example 13: Lotion Weight% 1. Sorbit 2.0 2.1,3-butylene glycol 2.0 3. Polyethylene glycol 1000 1.0 4. Polyoxyethylene oleyl ether (25E.O.) 2.0 5. Ethanol 10.0 6. Dissolution Example 4 (Chlorophosphoric acid sulfate solution) 0.5 7. Suitable amount of perfume 8. Residue of purified water 100

Example 14: Cream Foundation Weight% 1. Stearic acid 4.0 2. Glycerin monostearate 3.0 3. Cetanol 1,5 4. Isopropyl myristate 7.0 5. Liquid paraffin 10.0 6. White beeswax 3.0 8. Kaolin 3.0 9. Talc 1.0 10. Chlorophosphoric acid phosphorous oxide solution 1.0 11. Color pigment 1.0 12. Triethanolamine 3.0 13. Glycerin 3.0 14. Bentonite 1.0 15. Preservative proper amount 16. Suitable amount of perfume 17. Residue of purified water 100

Example 15: Shampoo Weight% 1. Lauryl sulfate triethanolamine 5.0% 2. Sodium polyoxyethylene lauryl ether sulfate 12.0 3.1,3-butylene glycol 4.0 4. Lauric acid diethanolamide 2.0 5. Disodium edetate 0.1 6. Dissolution Example 5 (human benzyloxypropylchlorophosphoric acid solution) 5.0 7. Preservative proper amount 8. Perfume proper amount 9. Residue of purified water 100

Example 16: Hair Liquid Weight% 1. Ethanol 25.0% 2. Polyoxypropyl ethyl ether phosphate 12.0 3. Polyoxypropylene monobutyl ether 5.0 4. Triethanolamine ruamide 2.0 5. Disodium edetate 0.1 6. Dissolution Example 6 (Chlorophosphoric acid quaternary alkylamine derivative solution) 3.0 7. Preservative proper amount 8. Perfume proper amount 9. Residue of purified water 100

Example 17: Heartonic Weight% 1. Ethanol 35.0% 2. Ethyl oleate 2.0 3. Polyoxyethylene (40) hydrogenated castor oil 2.0 4. Dissolution Example 3 (chlorocarboxylic acid fatty acid ester solution) 5.0 Perfume proper amount 6. Residue of purified water 100

Example 18: Bath agent Weight% 1. Sodium hydrogen carbonate 60.0 2. Anhydrous sodium sulfate 32.0 3. Borax 3.0 4. Chlorophosphonic acid (1,3-butylene glycol) solution 5.0

[0069]

EFFECT OF THE INVENTION The chlorogenic acid and / or chlorogenic acid derivative of the present invention has a lipid peroxide production inhibitory action, an ultraviolet absorbing action, and a melanin production inhibitory action. Whitening, skin aging prevention,
A hair protection effect can be expected. The fields of use thereof include various cosmetic compositions in the fields of pharmaceuticals / quasi-drugs or cosmetics (various preparations used for humans and other animals), specifically, lotions, emulsions, It is applied to creams (including ointments), oils, packs, soaps (including medicated soaps), body soaps, bath agents, shampoos, rinses, hairnics, hair sprays, etc.

[Brief description of drawings]

1 is a spectrophotometer (1 cm layer length: quartz cell),
The absorbance of ultraviolet rays was measured by the absorbance measuring method. As a sample, the dissolution example 1 used in Example 1 was used, and as a control, a para-aminobenzoic acid (PABA) solution having the same concentration was used.

Claims (3)

[Claims] 1. A whitening cosmetic comprising one or more chlorogenic acids and / or chlorogenic acid derivatives. 2. A cosmetic for preventing skin ageing, which comprises one or more chlorogenic acids and / or chlorogenic acid derivatives. 3. A hair-protecting cosmetic composition comprising one or more chlorogenic acids and / or chlorogenic acid derivatives.