KR101201524B1 - Composition for improvement of health of scalp and hair comprising dibenzo-p-dioxin derivatives - Google Patents

Abstract

The present invention relates to a scalp and hair health improving composition comprising a dibenzo-ｐ-dioxin derivative as an active ingredient. The scalp and hair health improvement composition prevents hair loss, promotes hair growth, prevents dandruff, improves scalp itch by safely and effectively inhibiting the growth of malassezia (Malassezia resista), oxidative stress, and inflammatory reactions occurring in the scalp and hair. It provides an excellent effect on suppression. In addition, the composition of the present invention provides an effect of maintaining the appearance of hair healthy and beautiful by effectively preventing the destruction of the surface of the hair and contamination by microorganisms.

Description

Composition for improvement of health of scalp and hair comprising dibenzo-p-dioxin derivatives}

The present invention relates to a composition comprising a dibenzo-p-dioxin derivative that maintains and improves the health of the scalp and hair.

The space formed by the scalp and hair is hot and humid to create an environment suitable for microorganisms. The scalp and hair tissues, which are maintained by proper hygiene and lifestyle, are properly restrained by the growth of harmful bacteria through a balance of blood circulation, metabolism, and immunity. However, when such balance is broken due to factors such as hormonal imbalance, various stresses, and insufficient hygiene management, various pathological phenomena may occur on the scalp and hair. For example, when harmful bacteria thrive on the scalp and hair surface tissues and inflammatory reactions increase, oxidative stress increases, tissue destruction, poor blood circulation, cell growth inhibition, and allergic symptoms appear around the scalp and hair roots. This can eventually cause hair loss, hair growth inhibition, excessive dandruff, scalp inflammation and itching. In addition to these serious symptoms, such special conditions of the scalp and hair can easily contaminate the hair surface, thereby compromising the aesthetic appearance of the hair. That is, even in a healthy state, the surface of the hair is contaminated by sweat, sebum, other skin debris, and microorganisms secreted from the scalp, so that the color of the hair, touch and smell are easily degraded. It is accelerated even more.

Sources that break the homeostasis of scalp and hair physiology include hormonal imbalances, various stresses, and poor hygiene. These factors interact with the human body in a variety of conditions, leading to complex physiological and biochemical imbalances in the scalp and hair, and ultimately to a variety of scalp and hair related symptoms.

On the other hand, the main products that have been developed to improve scalp and hair health have been reported to have serious side effects by seeking only suppression of one factor affecting scalp and hair health. For example, due to genetic factors, DHT synthase inhibitors have been developed and marketed to prevent hair loss caused by excessive male hormone DHT. However, there are many side effects, and it is fundamental to help homeostasis of scalp and hair physiology. There is a limit. In addition, products that use antifungal drugs to reduce dandruff have been released, but there is a concern of side effects as well, there is a limit to fundamental hair health improvement. In addition, in view of pursuing human safety and overall health, herbal medicines have been developed and commercialized. However, these products have better human safety than products using synthetic ingredients, but are difficult to standardize and difficult to derive correlations between effects and complex ingredients. Therefore, there is a need for the development of ingredients that can easily control the major factors that damage the scalp and hair health while being safe and standardized.

The present invention is to overcome the limitations of the prior art and to more effectively improve the scalp and hair health, while excellent antibacterial, antioxidant and anti-inflammatory effects that can be a key factor in maintaining and improving the health of the scalp and hair. In addition, by including a component having excellent affinity with hair, it is an object to provide a composition for improving scalp and hair health, effectively maintaining and improving the health of the scalp and hair even at low concentrations.

The present invention provides a composition for improving scalp and hair health comprising dibenzo-p-dioxine derivative as an active ingredient.

The dibenzo-p-dioxin derivative may be at least one compound selected from the group consisting of compounds represented by the following Chemical Formulas 1 to 10:

[Formula 1]

 (2)

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Chemical Formula 9]

[Formula 10]

In Chemical Formulas 1 to 10,

R is independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl, phenyl, C7-C12 phenylalkyl, C2-C20 alkanoyl, C3-C20 alkenoyl, hydroxyphenyl, dihydroxy Phenyl or trihydroxyphenyl.

The composition for improving scalp and hair health comprising the dibenzo-p-dioxine derivative of the present invention is safe for breeding malassezia resista, oxidative stress, and inflammatory reactions occurring in the scalp and hair. It effectively inhibits hair loss, promotes hair growth, prevents dandruff, improves scalp inflammation, and suppresses scalp itch. In addition, the composition of the present invention provides an effect of maintaining the appearance of hair healthy and beautiful by effectively preventing the destruction of the surface of the hair and contamination by microorganisms.

The present invention relates to a scalp and hair health improving composition comprising a dibenzo-p-dioxine derivative as an active ingredient.

The present inventors recognize the concept that it is difficult to effectively and safely improve scalp and hair health only by controlling one factor because the action of physiological and biochemical factors, such as dandruff, inflammation, and oxidative stress, which harm the scalp and hair, are combined with each other. The study was conducted with the aim of finding components or compositions capable of simultaneous and effective control of harmful bacteria, inflammatory reactions and oxidative stress. It also aimed to find a component or composition that ensures absolute safety that can prevent physiological imbalances that can occur through continuous use.

In order to achieve this goal, the present inventors have a structure derived from natural products that are not irritant / toxic, and have excellent affinity with hair and scalp tissue, and have excellent anti-oxidation, anti-inflammatory and antibacterial effects, and are harmful to hair and scalp tissue. Efforts have been made to find a component that can effectively block proliferation, inflammation, and oxidative stress in the long term, and have found that natural compounds having a dibenzo-p-dioxin skeleton satisfy these conditions very well.

Increased factors such as hair loss, hair growth inhibition, dandruff production, inflammation, and itching, such as hormonal imbalance, various stressors according to lifestyle, secondary harmful bacteria caused by hygiene, inflammatory reaction, and oxidative stress When combined, their action is more complex, resulting in allergic reactions, poor blood circulation, cell metabolism and growth inhibition. In addition, these causes eventually cause hair loss, hair growth inhibition, dandruff production, inflammation, itching, and the like.

As one of the secondary factors mentioned above, Malassezia restrica has recently been known (Christina M. Gemmer, Thomas L. Dawson Jr, et al., Journal of Clinical Microbiology, Sept Vol. 40, No. 9, p3350-3357 (2002)). This bacteria has been reported to cause dandruff, itching and seborrheic dermatitis when it is present in the scalp as part of the normal flora and overproliferated by environmental factors such as stress, climate change, sweat and food (Bergbrant IM Seborrhoeic). dermatitis and Pityrosporum yeasts.Current Topics in Medical Mycology. 6: 95-112 (1995)). In addition, when a lot of dandruff occurs, the scalp is excessively rubbed due to itching, thereby causing a wound or, in some cases, causing secondary inflammation and causing hair loss. Currently, antifungal agents such as ketoconazole, zinc pyrithion, itraconazole, and pyroctone olamine are mainly used as anti-dandruff agents. As these are artificially synthesized materials, questions about human safety have been raised. The present inventors have continued to confirm that dibenzo-p-dioxine derivatives are safe while effectively controlling Malassezia restrica.

In addition, the inflammatory response, which is one of the secondary factors described above, is also caused by stimulation of harmful bacteria, but is also chronically caused by metabolic syndrome due to westernized lifestyle, which is characterized by high calorie and lack of exercise. It may be caused temporarily by mental stress or shock. Inflammatory reactions damage the health of the scalp and hair tissues by accelerating tissue degeneration, inhibiting cell growth, and stimulating allergies by making the immune system overly sensitive. The inventors have found that dibenzo-p-dioxine derivatives are safe while effectively controlling inflammation.

In addition, oxidative stress, which is one of the secondary factors, is caused by the action of ultraviolet rays and pollutants, attacking DNA, cell membranes, and proteins of the scalp tissue, destroying the hair and the scalp tissue, and causing inflammation. Harm your health. The present inventors have found that dibenzo-p-dioxine derivatives are safe while effectively controlling oxidative stress.

In addition, these secondary factors are constantly supplied from lifestyles and the environment, continually stimulating hair and scalp, so that these factors can minimize the chances of working on the scalp and hair, for example to control these harmful factors. At the same time, it is necessary to develop a component that can be coated on the scalp and hair to protect more effectively. The inventors have found that the dibenzo-p-dioxine derivative has a very good hair affinity.

The above factors (harmful bacteria, inflammation, oxidative stress) in combination with each other, causing a vicious cycle that continues and worsens, causing hair loss, hair growth inhibition, excessive dandruff, scalp inflammation, itching and the like. Therefore, dibenzo-p-dioxine derivatives, which provide excellent effects on all of these complex factors, are excellent in promoting hair loss, inhibiting hair growth, excessive dandruff production, scalp inflammation, and itching. Provide effect.

The composition for improving scalp and hair health of the present invention, unlike conventional compounds having antimicrobial, antioxidant, and anti-inflammatory activity, has strong irritation and toxicity and thus adversely affects scalp health, it is not toxic or irritating, but rather It also has the feature of providing a function of relieving stimulation caused by other components. Also, due to the affinity between the scalp and the hair tissue, it is possible to concentrate the antibacterial, antioxidant and anti-inflammatory functions on the scalp and the hair tissue even with a small amount of use, thus effectively blocking or eliminating risk factors (microorganisms, free radicals, inflammatory reactions). It is characterized by. In addition, the existing antimicrobial agent should minimize the new stay in the scalp and hair tissue due to toxicity and irritation, but also has a problem of generating resistance, but the composition of the present invention is not toxic and irritant, so microorganisms in the scalp and hair tissue breeding There is no problem even if the antimicrobial layer is formed so as not to have any resistance.

In the present invention, the dibenzo-p-dioxin derivative may be one or more compounds selected from the group consisting of compounds represented by the following formula 1 to 10:

[Formula 1]

 (2)

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Chemical Formula 9]

[Formula 10]

In Chemical Formulas 1 to 10,

R is independently hydrogen, C1-C5 alkyl, C2-C5 alkenyl, phenyl, C7-C12 phenylalkyl, C2-C20 alkanoyl, C3-C20 alkenoyl, hydroxyphenyl, dihydroxy Phenyl or trihydroxyphenyl.

R is each independently hydrogen; methyl; Ethenyl; benzyl; Acetyl or oleoyl; 4-hydroxyphenyl; 2,4-hydroxyphenyl; Or 2,4,6-trihydroxyphenyl. More preferably hydrogen.

In the scalp and hair health improving composition of the present invention, dibenzo-p-dioxine derivatives are two or more selected from the group consisting of Chemical Formulas 3, 5, 6 and 8 It may be composed of a compound, wherein R = H in the formula 3, 5, 6 and 8 is preferred.

The dibenzo-p-dioxine derivatives are 10 to 60% by weight of the compound of Formula 3, 15 to 60% by weight of the compound of Formula 5, and 10 to 10% of the compound of Formula 6 based on the total weight of the derivative. 40 wt% and 5 to 30 wt% of the compound of Formula 8 may be included.

In addition, the dibenzo-p-dioxine derivative is 12 to 38% by weight of the compound of Formula 3, 18 to 57% by weight of the compound of Formula 5, 10 to 10 of the compound of Formula 6 based on the total weight of the derivative More preferably, it comprises 30% by weight and 10-30% by weight of the compound of the formula (8).

The dibenzo-p-dioxine derivative may be represented by Chemical Formula 1, Chemical Formula 2, Chemical Formula 4, in addition to two or more compounds selected from the group consisting of Chemical Formula 3, Chemical Formula 5, Chemical Formula 6 and Chemical Formula 8. It may be further comprises one or more compounds selected from the group consisting of Formula 9 and Formula 10. In this case, at least one compound selected from the group consisting of Chemical Formula 1, Chemical Formula 2, Chemical Formula 4, Chemical Formula 9 and Chemical Formula 10 may be included in an amount of 0.1 to 50 wt% based on the total weight of the derivative.

The composition for improving scalp and hair health of the present invention may be used not only as a medical use but also as a cosmetic. For example, the composition for improving scalp and hair health of the present invention includes pharmaceutical products for preventing hair loss and promoting hair growth, cosmetics having hair growth preventing and hair growth promoting functions, and the like. Cosmetics in the above means specifically hair cosmetics, shampoo, rinse, lotion, tonic, essence, soap, gel, mousse and the like.

The composition for improving scalp and hair health of the present invention may form various formulations with excipients commonly used in the medical and cosmetic compositions.

The daily amount of the dibenzo-p-dioxine derivative included in the scalp and hair health improving composition of the present invention is preferably about 1 to 100 mg. The amount of use is not limited to the above range. The composition for improving scalp and hair health of the present invention can be used for preventing hair loss, promoting hair growth, preventing dandruff, improving scalp inflammation, inhibiting scalp itch and the like. In addition, the composition may be used as a use for facilitating health promotion and hair care of the hair surface by effectively preventing the destruction and contamination of the hair surface.

The dibenzo-VII-dioxin derivatives included in the scalp and hair health improving composition of the present invention can be obtained by all conventional methods, can be synthesized using commercially available reagents, and extracted from natural products, in particular, seaweeds. It can also be obtained separately.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Example 1 Separation and Purification of Dibenzo-VII-dioxin Derivatives

1-1: Extraction of Polyphenol Mixtures from Brown Algae

After removing rhubarb ( Eisenia bicyclis , 1kg) using a juicer in a fresh state, adding 95% ethyl alcohol (4L), stirring at room temperature for 30 minutes, filtering only the solution, and drying to obtain 58 g of brown powder. All. The obtained dry powder was dissolved in 20 times distilled water (50 ° C.), mixed with a polyvinylpyrrolidone (PVPP) resin (10 times the weight of the dry powder), stirred (50 ° C., 1hr), and the solution was filtered off. And washed with a sufficient amount of distilled water (more than 5 times of PVPP resin by weight). 95% ethanol (3 times the weight of PVPP resin in weight ratio) was added to the washed PVPP resin, stirred at room temperature for 30 minutes, filtered, and the solution was taken and dried to obtain 8 g of a dark brown powder. The total polyphenol content was measured using the Pauline reagent and found to be 96.7%.

1-2: Separation of dibenzo-p-dioxin derivatives from purified polyphenol mixtures

The polyphenol mixture obtained in Example 1 was filtered through a 0.2 μm membrane filter and loaded on high performance liquid chromatography. In high-performance liquid chromatography, the column was HP ODS Hypersil column, distilled water and methanol as solvent, and the supply of solvent was linear over 30 minutes from 15% to 70% methanol at a flow rate of 1.0 ml / min. 10 active materials were separated by a gradient. Each compound was identified to be a dibenzo-VII-dioxin derivative of Formulas 1-10.

[Formula 1]

 (2)

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Chemical Formula 9]

[Formula 10]

In Formulas 1 to 10, R is hydrogen.

Example 2: Evaluation of hair affinity, antioxidant, anti-inflammatory and antimicrobial activity

Hair affinity to dibenzo-p-dioxin derivatives isolated in Example 1, and natural ingredients quercetin, EGCG (Epigallocatechin gallate), catechin and salicylic acid, which are well known for their excellent antioxidant, anti-inflammatory or antibacterial properties Antioxidative activity, anti-inflammatory activity, antimicrobial activity was evaluated and the results are shown in Table 1 below.

2-1: Hair Affinity Evaluation

The affinity evaluation with the hair of the dibenzo-p-dioxin derivative isolated in Example 1 was performed as follows.

A total of 100 g of hair (approximately 1 cm long) obtained by 5 male and 5 female haircuts were secured in total, 10 g each, and placed in a 1 mM TX-100 aqueous solution (1 L) and stirred at room temperature. After washing with 10 L of distilled water, it was dried for 30 minutes in a 40 ℃ convection oven (Convection Oven). Meanwhile, a sample solution of each of the dibenzo-p-dioxin derivatives separated in Example 1 was dissolved in DMSO to make 0.1 wt%. 30 microliters of sample solution was added to 10 mL of phosphate buffer solution (pH 7.0, 0.1 mM), and the mixture was sufficiently mixed. Then, 1 g of prepared hair was added and stirred vigorously at 40 ° C. for 10 minutes. The same procedure was followed for each sample solution without hair. Only the solution was withdrawn from each solution, and the respective absorbances were measured at 254 nm and 25 ° C.

For each sample, the absorbance of the solution in the absence of interaction with the hair is A100, and the absorbance in the presence of the interaction is A, and the hair affinity of each sample is calculated using the following equation. It is shown in Table 1 below.

Hair Affinity (%) = 100 X (A100-A) / A100

2-2: Antioxidant Evaluation

Antioxidant activity evaluation of the dibenzo-p-dioxin derivative isolated in Example 1 was carried out as follows.

2 mg of DPPH reagent was accurately weighed, and 1.2 ml of a solution dissolved in 15 ml of EtOH was mixed again with 3 ml of EtOH and 0.5 ml of DMSO to prepare a DPPH solution. Each sample solution to be evaluated was dissolved in DMSO to prepare a respective sample solution so as to have a concentration of 100 µg / ml. 50 μl of each sample solution and the prepared DPPH solution were mixed and reacted at room temperature for 10 minutes, and then absorbance was measured at 518 nm. The absorbance of the control group without adding the sample is A0, and the absorbance of the solution to which the sample is added is A, and the DPPH radical scavenging activity is calculated by the following equation and is shown in Table 1 below.

DPPH radical scavenging activity (%) = 100 X (A0-A) / A0

2-3: Anti-inflammatory effect evaluation

The anti-inflammatory effect of the dibenzo-p-dioxin derivative isolated in Example 1 was evaluated as follows. Mouse macrophage RAW 264.7 (Korean Cell Line Bank) was incubated in DMEM (10% fetal bovine serum and 1% penicillin / streptomycin) medium at 37 ° C., 5% CO ₂ (fully humidified air). The cultured cells were transferred to 96-well plates (200 microliters / well) and dissolved in LPS (E. coli, serotype 055: B5, final concentration of 1 mg / mL) and DMSO and prepared at a concentration of 100 µg / ml. Each sample solution (final concentration = 10 μg / mL) was added and incubated for 18 hours. For the solution not treated with LPS, a negative control group, LPS treatment, but a solution treated with saline instead of the sample was used as a positive control group. After separating the supernatant, the PGE2 concentration (pg / mL) indicating the degree of inflammatory response was measured according to the guide provided by the EIA kit manufacturer (Cayman Chemical Co.), and the relative anti-inflammatory effect (%) was calculated according to the following equation. It was calculated and shown in Table 1 below.

When PGE2 concentration in the positive control group was CM, PGE2 concentration in the negative control group was C0, and PGE2 concentration at each sample treatment was C.

Anti-inflammatory effect (%) = 100 X (CM-C) / (CM-C0)

2-4.Antibacterial activity measurement

Evaluation of the antimicrobial activity of the dibenzo-p-dioxin derivative isolated in Example 1 was carried out by measuring the inhibitory activity against Malassezia restricta fungi, the causative agent of dandruff, using the Agar diffusion method. Antibacterial activity was carried out by plate medium diffusion method using a paper disk containing each sample. First, Malassezia restricta strains were cultured (Modified Leeming and Notman agar medium, 0.1% polypeptone, 2.0% glucose, 5.0% Malt extract, 2.0% desiccated ox bile, 0.2% glycerol, 1.0% Tween 40 and 2.0% agar in distilled water Cultured at 36 ° C. Meanwhile, 5 mg of each sample was dissolved in 50 μl of ethanol, and then absorbed to spread evenly on a circular paper having a diameter of 8 mm and a thickness of 1.5 mm, and the solvent was completely evaporated, followed by inoculation of the cultured Malassezia fungi. The antimicrobial activity was tested in mLNA (Modified Leeming and Notman agar medium) plate medium. After 48 hours of incubation in the above culture conditions, the diameter of the circular growth-resistant ring formed around the paper disc impregnated with each sample was measured, and then the diameter of the disc (8 mm) was subtracted by 2 ( Relative antimicrobial activity was compared. The results are shown in Table 1 below.

sample Hair affinity
(%) DPPH radical scavenging activity (%) Anti-inflammatory effect (%) Antibacterial activity (lower radius, mm) Formula 1 66 87 72 6 (2) 71 92 74 6 (3) 72 93 85 6 Formula 4 68 74 76 6 Formula 5 82 88 82 10 6 85 88 70 8 Formula 7 83 87 74 8 8 87 86 83 8 Formula 9 65 78 73 6 10 67 77 85 8 Formula 5 (R = acetyl): Formula 5 (R = H) = 3: 7 54 72 71 5 Formula 8 (R = oleoyl): Formula 8 (R = H) = 1: 9 73 83 77 7 Formula 3 (R = methyl): Formula 3 (R = H) = 2: 8 67 72 70 6 Quercetin 26 77 23 One EGCG 35 89 38 2 catechin 21 75 18 0 Salicylic acid 5 23 81 8

Example 3 Preparation of Composition

It was confirmed from Examples 1 and 2 that the dibenzo-p-dioxin derivatives are all excellent in hair affinity, antibacterial activity, anti-inflammatory effect and antioxidant effect. In particular, hair affinity, antimicrobial activity and anti-inflammatory effect were remarkably superior to other natural products. Antioxidant effect also showed the highest level. From these results, it was expected that the dibenzo-p-dioxin derivatives of the present invention would have an excellent effect on improving scalp and hair health. And it was expected to show a better effect through the combination between them. Therefore, Compositions 1 to 5 were prepared by selecting components having excellent activity. The chemical composition of each composition is shown in Table 2 below.

sample Composition of the sample
(R = H in formula 1 to 10, the following ratio is the weight ratio) Composition 1 Formula 3: Formula 5: Formula 6: Formula 8 = 25: 35: 20: 20 Composition 2 Formula 5: Formula 6: Formula 7: Formula 8 = 43: 22: 12: 23 Composition 3 Formula 3: Formula 5: Formula 6: Formula 8: Formula 10
= 50: 15: 10: 10: 15 Composition 4 Chemical Formula 1: Chemical Formula 2: Chemical Formula 3: Chemical Formula 4: Chemical Formula 5: Chemical Formula 6: Chemical Formula 7: Chemical Formula 8: Chemical Formula 9: Chemical Formula 10
= 5: 5: 20: 3: 25: 15: 8: 12: 2: 5 Composition 5 Formula 1: Formula 2: Formula 3: Formula 10 = 16: 8: 60: 16

Example 4: Evaluation of the hair growth promoting effect of the composition

The hair growth effects of the compositions according to the invention were tested. 7 weeks old mouse (C57BL / 6) was removed from the back of the hair region, and the back skin was selected to select the five to each material group to clean the composition of Examples 1 to 5 of each mouse group each day 150 μl was applied for 21 days. In the comparative group, EGCG which showed a relatively good effect in the comparative sample of Example 2, and the negative control group to contain no sample, so as to water / ethanol / 1, 3- butylene glycol (volume ratio: 5/3/2) A configured solvent was used. 23 days after the start of application, the weight of the newly grown hair was measured and compared with the negative control group, and the results are shown in Table 3 below.

Treatment Sample Newly grown hair weight (mg) Voice control 22 ± 19 Composition 1 96 ± 17 Composition 2 88 ± 15 Composition 3 85 ± 18 Composition 4 90 ± 17 Composition 5 70 ± 10 EGCG 65 ± 15

As can be seen from Table 3, when the composition according to the present invention and EGCG were contained, the average value of hair weight was higher than that of the group coated with the general solution (water / ethanol / 1,3-butylene glycol). In particular, it was confirmed that the compositions 1 to 4 containing high components of high hair affinity generally have a high hair growth promoting effect as compared to the composition 5 having a high component of high affinity for hair. Composition 1, which had a balance of hair affinity, antioxidant power, anti-inflammatory and antibacterial activity, had the best hair growth promoting effect.

Example 5 Determination of Scalp Inflammation and Inhibitory Effect of the Composition

MEST (Mouse Ear Swelling Test) method was applied to measure the effect of inhibiting and inhibiting scalp inflammation by stimulation of the hair dye of the composition. To this end, compositions 1 to 5 of Example 3 were used, and EGCG was used as a comparative group.

As animals, 6-8 week old female CF-1 mice were used. Mice were divided into seven groups after approximately two weeks of acclimatization, with 10 animals in each group. The animal laboratory was controlled to light at a 12 hour cycle while maintaining a humidity of 20 ± 2 ℃, 50 ± 10%. Animal food was supplied throughout the entire experimental period and water was freely available for drinking.

Hair was removed from the abdomen of the rat, and 25 μl of Freund's complete adjuvant (FCA) was injected twice into the dermal layer of the abdominal skin. After removing the stratum corneum of the mouse abdominal skin with strong tape, 100 μl of hair dye was applied to the abdominal skin of the mouse, and after 30 minutes, the same amount of the composition 1 to 5 or the comparative material was applied to the skin. The same experiment was repeated after 3 days. Six days after the start of the experiment, the thickness of the swelling ear (ear swelling) and the frequency of swelling occurrence were measured.

Treatment Sample Ear thickness (㎛) occurrence frequency Negative control group 402 ± 32 9/10 Composition 1 264 ± 21 3/10 Composition 2 284 ± 26 3/10 Composition 3 271 ± 24 5/10 Composition 4 268 ± 30 4/10 Composition 5 287 ± 19 4/10 EGCG 350 ± 26 6/10

As can be seen from Table 4, when the composition according to the present invention is treated with a hair dye, it can be seen that the swelling frequency of the ear is significantly reduced, and the thickness of the ear is also significantly reduced, thereby confirming the effect of alleviating inflammation. there was. Thereby, it can be judged that the composition by this invention has the effect of alleviating the inflammation by a hair dye.

Example 6 Scalp Itching

The anti-itch effect of the composition according to the present invention was tested. Hairless mice were used to facilitate skin application of Compositions 1-5 and Comparative Material (EGCG) of Example 3. All hairless mice were males of 7 weeks old, and 10 mice were used in each group. After treating the composition 1 to 3 or 100 μl of the comparative substance twice a day for 5 days, itching substance (Compound 48/80) was dissolved in physiological saline at a concentration of 1 mg / ml and injected into the dermal layer. Immediately after the injection, the hairless mice were placed in the cage for observation and photographed for 30 minutes, and the number of scratches on the itch with the hind legs was measured and displayed in numbers. Except for scratching by the forefoot or biting by mouth, only the action of scratching the injection site with the hind feet was considered as an indication of the itch behavior, and the measurement results are shown in Table 5 below.

Treatment Sample Average number of scratches in 30 minutes Negative control group 180.6 ± 15.3 Composition 1 130.2 ± 16.3 Composition 2 126.2 ± 15.6 Composition 3 135.2 ± 14.9 Composition 4 125.3 ± 21.3 Composition 5 120.5 ± 19.2 EGCG 160.3 ± 16.3

As can be seen in Table 5, when the pre-treatment with the composition 1 to 5 of Example 3 according to the present invention can be confirmed that the number of scratches to reduce the effect of suppressing itching.

Example 7: Preparation of Formulations

The compositions, which showed overall excellent effects in the in vivo experiments, were prepared in various types of formulations to be applied to actual scalp and hair in daily life.

7-1: Hair tonic preparation with the composition shown in Table 6 below

Ingredient (% by weight) Formulation Example 1 Comparative Example 1 Comparative Example 2 ethanol 50.00 50.30 50.00 Active ingredient 0.30 (Composition 1) 0.30 (quercetin) 0.30 (EGCG) glycerin 3.00 3.00 3.00 Silicic acid 0.05 0.05 0.05 menthol 0.02 0.02 0.02 Purified water 46.63 46.63 46.63

7-2: hair shampoo in the composition shown in Table 7 below

Ingredient (% by weight) Formulation Example 2 Comparative Example 3 Comparative Example 4 Purified water 50.74 50.74 50.74 Active ingredient 0.15 (Composition 1) 0.15 (salicylic acid) 0.15 (EGCG) Sodium Laureth Sulfate 36.00 36.00 36.00 Cocamidopropyl Betaine 8.00 8.00 8.00 Propylene glycol 2.00 2.00 2.00 Glycol distearate 1.50 1.50 1.50 Purified salt 1.00 1.00 1.00 Polyquaternium-7 0.50 0.50 0.50 Citric acid 0.10 0.10 0.10 Spices 0.01 0.01 0.01

7-3: Hairliner prepared by the composition of Table 8 below

Ingredient (% by weight) Formulation Example 3 Purified water 89.09 Composition 2 0.20 Protylene glycol 2.00 Cetyltrimethylammonium chloride 1.00 Cetyl alcohol 3.00 Stearyl alcohol 3.00 Mineral oil 0.50 Citric acid 0.20 Polydimethylsiloxane 1.00 Spices 0.01

7-4: Hair lotion was prepared using the composition shown in Table 9 below.

Ingredient (% by weight) Formulation Example 4 Purified water 92.14 Composition 4 0.15 Cetostearyl alcohol 2.00 Disoudium EDTA 0.20 Hydroxyethyl cellulose 0.50 Mineral oil 5.00 Spices 0.01

Example 8. Hair loss prevention effect (hair tonic) evaluation

Twenty subjects with initial hair loss were tested for anti-hair loss for 12 weeks. After the hair tonic of Formulation Example 1, Comparative Example 1, and Comparative Example 2 of Example 7-1 of Example 7 for 12 weeks once a day, after 12 weeks have elapsed after collecting the hair loss hairs to collect the number The results are shown in Table 10 below.

Treated group Dropout Count Formulation Example 1 50 Comparative Example 1 80 Comparative Example 2 75

As can be seen in Table 10, it was confirmed that the treatment of the hair tonic of the formulation example 1 according to the present invention significantly reduced the number of hair loss compared to the case of treating the comparative example 1 or 2.

Example 9 Evaluation of Prevention of Dandruff and Itching Prevention

9-1: Anti-dandruff effect measurement

The anti-dandruff production effect was measured for the hair shampoo (Formulation Example 2, Comparative Example 3, or Comparative Example 4) of 7-2 of Example 7.

Ten men and women with relatively high dandruff were selected, triturated with a conventional shampoo before the start of the test, and the dandruff accumulated for 3 days was collected, and the weight of the collected dandruff, the composition (Formulation Example 2), salicylic acid (Comparative Example 3) or EGCG The hair shampoo containing (Comparative Example 4) was triturated for 1 month and the weight of the dandruff accumulated for 3 days was evaluated.

At this time, the collection of the accumulated dandruff was allowed to test the scalp of the test subjects using about 5g of normal shampoo, and then washed with about 2 to 3 liters of water. The washed water was filtered through a 800 microporous filter, and the dry weight of dandruff on the filter was measured. The rate of dandruff reduction was determined by the following equation. 11 is shown.

Dandruff reduction rate (%) = [(weight of dandruff before test start-mg weight of dandruff after start of test (mg)) / weight of dandruff before start of test (mg)] x 100

group Average reduction rate (%) Has anti-dandruff effect No dandruff effect I do not know Tested embroidery Formulation Example 2 30.2 5 2 3 10 Comparative Example 3 15.3 One 5 4 10 Comparative Example 4 12.6 2 5 3 10

As can be seen in Table 11, the hair shampoo of the formulation example 2 according to the present invention was confirmed to significantly increase the anti-dandruff effect compared to the case of treatment with Comparative Example 3 or 4.

9-2: Evaluation of Itching Prevention Effect

The anti-itch effect was measured for the hair shampoo (Formulation Example 2, Comparative Example 3 or Comparative Example 4) of 7-2 of Example 7.

Men and women who usually feel itching to use the product of Formulation Example 2, Comparative Example 3 or Comparative Example 4 for 8 weeks, once every two days, 10 people per product for 8 weeks, and then evaluated in accordance with the evaluation criteria of Table 12 below through an interview In Table 13, the average of the ratings is given.

Evaluation division (itch reduction effect) grade Is very 5 have 4 is average 3 none 2 No One

Formulation Scalp itching effect Formulation Example 2 4.5 Comparative Example 3 3.2 Comparative Example 4 2.8

As can be seen in Table 13, when the hair shampoo of Formulation Example 2 according to the present invention it was confirmed that compared to the case of treatment with Comparative Example 3 or 4 it was confirmed that the anti-dandruff scalp itching effect significantly increased.

Example 10. Evaluation of Usability Improvement Effect

Twenty females 25 to 50 years old were used to use the hair shampoo (Formulation Example 2, Comparative Example 3 or Comparative Example 4) of Example 7 on the hair according to the general usage, and after 30 minutes of drying, Satisfaction with feeling of gloss, smoothness and combing was evaluated. We also evaluated the satisfaction with the shine, smoothness and combing felt after 12 hours. Each participant asked to use all three different shampoos at weekly intervals, but did not know what kind of shampoo they were.

For the satisfaction evaluation, the highest level was 5 and the lowest level was 1 for each item, and one of 5, 4, 3, 2, and 1 was selected. The average of the evaluation scores for each item is shown in Table 14 below. Immediately after use, the satisfaction of all shampoos was high overall, and the use of shampoos of Formulation Example 2 was relatively high. However, when the shampoos of Comparative Examples 3 and 4 were used in the gloss, smoothness, and combing after 12 hours, the satisfaction was remarkably decreased, whereas when using Formulation Example 2, the satisfaction was maintained at a very high level. Thus, it can be seen that the composition of the present invention maintains a satisfactory touch of hair significantly for a long time.

Claims (12)

delete delete delete To prevent hair loss, characterized in that it comprises at least two dibenzo-p-dioxine derivatives selected from the group consisting of compounds represented by the formula (3), (5), (6) and (8) Cosmetic composition for promoting hair growth:
[Formula 3]

[Formula 5]

[Formula 6]

[Formula 8]

R is H in the above formulas. The dibenzo-p-dioxine derivative according to claim 4, wherein the dibenzo-p-dioxine derivative is 10 to 60% by weight of the compound of Formula 3, 15 to 60% by weight of the compound of Formula 5, based on the total weight of the derivative. 10 to 40% by weight of the compound of formula 6 and 5 to 30% by weight of the compound of formula (8) comprising a cosmetic composition for preventing hair loss and promoting hair growth. The method of claim 5, wherein the cosmetic composition for preventing hair loss and promoting hair growth is at least one dibenzo-p- selected from the group consisting of compounds represented by the following Chemical Formulas 1, 2, 4, 9 and 10: A cosmetic composition for preventing hair loss and promoting hair growth, further comprising a dibenzo-p-dioxine derivative:
[Chemical Formula 1]

(2)

[Formula 4]

[Formula 9]

[Chemical formula 10]

R is H in the above formulas. The method according to claim 6, wherein at least one dibenzo-p-dioxine derivative selected from the group consisting of compounds represented by Formula 1, Formula 2, Formula 4, Formula 9 and Formula 10 is a composition. Hair loss prevention and hair growth cosmetic composition, characterized in that it comprises 0.1 to 50% by weight relative to the total weight of the total dibenzo-p-dioxine (dibenzo-p-dioxine) derivative. delete delete delete delete The cosmetic for preventing hair loss and promoting hair growth according to any one of claims 4 to 7, which is prepared in a formulation selected from the group consisting of shampoo, rinse, lotion, tonic, essence, soap, gel and mousse. Composition.