KR20070042739A - Composition for preventing and treating of dandruff comprising vitamin b1 derivatives - Google Patents

Abstract

The present invention relates to a derivative of vitamin B ₁ and a composition containing the same related to the prevention and treatment of dandruff, more specifically the thiamine dodecylbenzenesulfonate salt represented by the following formula (1) and thiamine lauryl represented by the following formula (2) A salt of at least one vitamin B ₁ selected from the group consisting of sulfates, thiamine dodecylbenzenesulfonate salts represented by the following formula (1), thiamine lauryl sulfate salts represented by the following formula (2), and thiamine hydrochloride represented by the following formula (3) Or it relates to a composition for preventing or treating dandruff, characterized in that it contains a salt of vitamin B ₁ including at least one selected from the group consisting of sulfate group, carbonyl group, and vinyl group.

The composition according to the present invention is environmentally and ecologically friendly by using a salt of vitamin B ₁ which is a naturally-derived substance, and has an excellent antimicrobial effect because it can increase the solubility in water at the same time without a problem of safety for the human body. In particular, it is effective to inhibit the growth and activity of dandruff Pityrosporum ovale ( Pityrosporum ovale ) can prevent or treat dandruff.

[Formula 1]

[Formula 2]

[Formula 3]

Dandruff, vitamin B1, salts, thiamine hydrochloride, thiamine dodecylbenzenesulfonate salt, thiamine lauryl sulfate, phytirosporum obale, composition.

Description

Composition for preventing and treating dandruff comprising vitamin B1 derivatives}

1 is a result of measuring an antimicrobial effect of vitamin B ₁ derivatives and of vitamin B _1, Fig.

The present invention relates to derivatives of vitamin B ₁ and compositions containing them which are involved in the prevention and treatment of dandruff.

In general, dandruff means that dead or peeled cells of the scalp caused by the active metabolism of the human body are peeled off and separated into a hard keratin-like mass formed by the dryness of the scalp sebaceous glands. Dandruff is a noticeable increase in the amount of dandruff, which in many cases is likely to recur, usually accompanied by itching. When dandruff occurs, the scalp is excessively rubbed due to the dandruff or itching, and the scalp is injured. In some cases, the scalp may be inflamed or cause hair loss. .

Therefore, dandruff is a type of seborrhoeic dermatitis in the scalp, which is known to be caused by the accumulation and accumulation of sebaceous glands, sweat glands, and keratinized substances in the epidermis and infection of microorganisms. Actively active face, head, armpits, genitals, etc. It occurs well after birth or after puberty.

Recently, it has been known that the causative agent of dandruff is yeast, and the interest of this has recently increased due to the discovery of a fungus called Pityrosporum ovale or Malassezia furfur . The role it plays in the development of dandruff is still unknown.

Pytyrosporum obale and Malassezia puffer are the normal fungi in the scalp and are found in about the same number in people with or without dandruff. It is believed that dandruff is caused by a difference in sensitivity to dandruff.

Anti-dandruff substances used in conventional shampoo compositions have a problem that most of them are in the form of lumps and are not soluble in water. In order to solve this problem, it was used in a high viscosity opaque cream (cream) or lotion (lotion).

In addition, most antidandruff activators have a variety of colors and have a problem of discoloration when they are exposed to light or air. To prevent this, it is inevitable to add large amounts of color additives, opaque containers are used, and color protectors may be added.

Meanwhile, the most common anti-dandruff therapeutic ingredient is zinc pyrithione (hereinafter referred to as ZPT). Zinc pyrithione is effective in treating and improving dandruff by inhibiting scleroderma hyperkeratosis and antifungal effect, but it is difficult to uniformly disperse in the composition due to water insolubility and high specific gravity. NH, Allergic contact dermatitis caused by zinc pyrithione associated with pustular psoriasis, Am. J. Contact Dermat ., 8 , p170, 1997) and environmental toxicity have been reported, which has limited problems in applying it to hair cosmetics at high concentrations. .

The ZPT is generally sold in powder or 48% dispersion, has a slight odor, is off-white, and insoluble in water, alcohol, isopropyl myristate, and common solvents. In addition, since ZPT decomposes when exposed to light, a UV absorption prevention factor should be added or an opaque container should be used.

In addition, ZPT forms complex salts with heavy metals, combines with Fe, Cu, and the like to form strong tint compounds and destroys the prototype of shampoo formulations, so heavy metals or divalent cation compounds must be removed.

In addition, since ZPT adsorbs to the hair, not to the scalp, it has a limitation that the conditioning effects such as hair softness, glossiness, and smoothness are inferior.

Selenium sulfide (SES), another anti-dandruff therapeutic ingredient, is a bright orange and hardly soluble in most solvents. Because of this property, SeS must be dispersed in the shampoo composition like ZPT by adding a thickening agent such as hydroxypropyl methylcellulose or sodium chloride. In addition, magnesium aluminum silicate, methyl cellulose, and ammonium chloride are used as viscosity huilders, and the anti-dandruff component does not easily sink due to the high viscosity enhancer.

Salicylic acid is also used as a dandruff prevention, sterilization and keratin dissolving agent, but also has a weak sterilizing power against dandruff.

Pyroctone olamine (Piroctone Olamine: manufactured by Hoechst) is known to have several effects and is particularly effective against antioxidants, but its antimicrobial activity is weak and it is known to be effective only when used in large quantities. 0.5 to 2.0% should be used for the olamine to have sufficient effect. However, this component also has restrictions on the amount of use due to safety issues on the human body (Cosmetics and Toiletries, 102, 6, Dec., 1987).

Currently, ketoconazole is used as an active ingredient of an anti-dandruff treatment agent such as nizoral, but there is a problem that can cause adverse effects on the endocrine system when ketoconazole is used for a long time. Oral administration over a long period of time causes side effects such as hepatotoxicity and fungal infections of the skin, nails and toenails, or hair with little or no vascular distribution, making it difficult to distribute and accumulate a sufficient amount of drugs. In the same case, it is difficult to penetrate the drug deeply, and many antifungal drugs are insoluble in water.

Therefore, itraconazole was newly synthesized through research to develop an antibacterial agent that is safer to humans while having a stronger antibacterial effect than ketoconazole. This triazole derivative has been found to be very effective against many pathogenic fungi associated with humans and has a high affinity for keratinous tissues. However, because itraconazole is not transported through the sweat glands like ketoconazole, it should be taken as an oral medication, which has the disadvantage of slow transportation, and requires at least 1,000 mg of prescription daily to satisfy satisfactory treatment and prevent recurrence. There is a report. In addition, the majority of patients are prescribed several kinds of drugs at the same time, but the administration of the combination may cause problems that can affect the liver cells toxicity and immune system, and can increase the efficiency or adverse effect of a drug, It can also cause symptoms like headaches or nausea.

As described above, the anti-dandruff agents used in the conventional anti-dandruff hair composition have a common disadvantage that the use of the anti-dandruff anti-dandruff prevents dandruff prevention or treatment because the sterilization power is limited due to legally limited usage. In addition, because it is a synthetic chemical can give consumers a negative thought, a natural-derived anti-dandruff composition that is environmentally and ecologically friendly and excellent in human safety is required.

The present inventors to solve the problems of the conventional anti-dandruff agents described above, the environment and ecology-friendly, While reviewing a material having even dandruff prevention or treatment effect without causing the problem of safety to human body, vitamin B ₁ It was confirmed that the salt of the antibacterial effect against the common bacteria and the antibacterial effect of Pytirosporum ovale (danger bacteria) to complete the present invention.

Accordingly, an object of the present invention is to provide a salt of vitamin B ₁ and at the same time, by using a salt of vitamin B ₁ which is a naturally derived substance, it is environmentally and ecologically friendly, and solubility in water without problems of safety to the human body. At the same time it can be increased to have an excellent antimicrobial effect, in particular to inhibit the proliferation and activity of the dandruff ptyrosporum obale to provide a composition that can prevent or treat dandruff.

In order to achieve the above object, the present invention provides a thiamine dodecylbenzenesulfonate salt represented by the following formula (1).

[Formula 1]

The present invention also provides thiamine lauryl sulfate represented by the following formula (2).

[Formula 2]

In addition, the present invention is at least one vitamin B ₁ selected from the group consisting of thiamine dodecylbenzenesulfonate salt represented by the formula (1), thiamine lauryl sulfate salt represented by the formula (2) and thiamine hydrochloride represented by the formula (3) It provides a composition for preventing or treating dandruff, characterized in that it contains a salt of.

[Formula 1]

[Formula 2]

[Formula 3]

In another aspect, the present invention provides a composition for preventing and treating dandruff, characterized in that it contains a salt of vitamin B ₁ including at least one selected from the group consisting of a sulfate group, a carbonyl group, and a vinyl group.

In the composition for the prevention or treatment of dandruff, the composition is characterized in that it inhibits the growth and activity of the strain Ptyrosporum ovale ( Pityrosporum ovale).

In the composition for preventing or treating dandruff, the composition is characterized in that it contains 0.001 to 1.0% by weight of the salt of vitamin B _{1 relative} to the total weight of the composition.

In the composition for preventing or treating dandruff, the composition is characterized in that the hair cosmetic composition.

In the composition for preventing or treating dandruff, the hair cosmetic composition is characterized in that it has a formulation selected from the group consisting of shampoo, rinse, hair conditioner, hair tonic, hair cream, hair treatment, hair spray and hair mousse.

In the composition for preventing or treating dandruff, the formulation is characterized in that the shampoo.

In the composition for preventing or treating dandruff, the composition is characterized in that the pharmaceutical composition.

In addition, the present invention is the first step of adding anhydrous chemotaxis to thiamine hydrochloride and then melting at room temperature; A second step of adding sodium dodecylbenzenesulfonate to the solution, stirring at room temperature for 2 to 4 hours, and then standing at 10 to 40 ° C. for 3 hours 30 minutes to 4 hours; And it provides a method for producing a thiamine dodecylbenzenesulfonate salt, characterized in that it comprises a third step of filtering the solution under reduced pressure.

Hereinafter, the present invention will be described in detail.

Thiamin (Thiamine) has a chemical name of vitamin B _1, is a vitamin extracted from rice bran. Thiamin is one of the earliest known vitamins, synthesized by green plants and microorganisms, contained in rice bran, embryos, yeast, and also found in animal nerves. If you take nutrition that is unbalanced in the white rice, each of which is a deficiency, neuritis symptoms, heart failure, etc. cause.

Anionic surfactants are activators whose ion dissociation in aqueous solution and anionic moieties exhibit surfactant activity. The hydrophilic groups of the anionic surfactants are most commonly used as soluble salts, such as carboxylic acid, sulfate ester, and sulfonic acid. Anionic surfactants generally have excellent properties as surfactants, but their antimicrobial action is weak and cannot be used as a bactericide. However, in combination with a suitable acid, it may be a useful fungicide, or may be combined with other fungicides and formulated as a cleaning and fungicide.

The present inventors have prepared new salts of vitamin B ₁ by combining dodecylbenzenesulfonate salts, lauryl sulfate, and the like, which are anionic surfactants to vitamin B _1, ie, thiamin, and the salt and thiamine hydrochloride of the prepared vitamin B ₁ It has been found to have antimicrobial activity and, in particular, to inhibit the proliferation and activity of the dandruff, phytirosporum obale.

Dandruff is a normal fungus that has lived on the scalp since puberty and is found in about the same number in people who have or have not had dandruff.It is thought that dandruff occurs when they multiply due to differences in sensitivity to environmental and physiological factors. . The causative agent of such dandruff is yeast. Therefore, in order to prevent or treat dandruff, it is necessary to suppress abnormal overgrowth of dandruff, and a salt of vitamin B ₁ capable of inhibiting the growth and activity of the bacterium has an effect of preventing or treating dandruff.

As the salt of vitamin B ₁ contained in the composition for preventing or treating dandruff according to the present invention, thiamine dodecylbenzenesulfonate salt represented by the formula (1), thiamine lauryl sulfate represented by the formula (2) and the formula It may be at least one selected from the group consisting of thiamine hydrochloride represented by 3.

In addition, the salt of vitamin B ₁ contained in the composition for preventing or treating dandruff according to the present invention may include at least one selected from the group consisting of a sulfate group, a carbonyl group, and a vinyl group.

In the composition for preventing or treating dandruff, the salt of vitamin B ₁ is contained in an amount of 0.001 to 1.0% by weight, more preferably 0.004 to 0.01% by weight, based on the total weight of the composition. This is because if the content is less than 0.001% by weight relative to the total weight of the composition, the anti-dandruff effect can not be sufficiently exerted, and if it exceeds 1.0% by weight, it may cause problems in the stability of the formulation and the safety for the human body. More preferably, 0.004 to 0.01% by weight.

In addition, in the composition for preventing or treating dandruff, the hair cosmetic composition may have a conventional formulation, for example, shampoo, rinse, hair conditioner, hair tonic, hair cream, hair treatment, hair spray and hair mousse. And the like. The composition of each of these formulations may contain a variety of bases and additives necessary for the formulation of the formulation and are suitable, and the types and amounts of these components can be readily selected by those skilled in the art.

In addition, when the composition for preventing or treating dandruff according to the present invention is a pharmaceutical composition, it is preferable to apply an appropriate amount in the morning and evening according to the affected area once or several times with a conventional external preparation such as ointment or cream.

Hereinafter, representative base ingredients and additives will be described by taking compositions of representative shampoo formulations of hair cosmetic compositions as examples.

For example, the shampoo formulation may be a shampoo composition including synthetic surfactants and preservatives, thickeners and viscosity modifiers, pH adjusters, flavorings, dyes, hair conditioning agents and water, which are detergent components. The active agent may be any selected from anionic, amphoteric, nonionic and cationic surfactants, and may contain such surfactant in an amount of 10 to 50% by weight, more preferably 10 to 30% by weight of the composition. .

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples, but the present invention is not limited only to these examples.

Example 1 Synthesis of Thiamine Dodecyl Benzenesulfonate Salt

To 3.68 g (10.90 mmol) of thiamine hydrochloride (available from across), 50 mL of anhydrous main column was added, stirred at room temperature, and dissolved. Then, 7.60 g (21.80 mmol) of sodium dodecylbenzenesulfonate was added to the solution for 3 hours at room temperature. Stirred. The solution was allowed to stand at 10 ° C. for 3 hours 30 minutes to 4 hours, and then filtered under reduced pressure to obtain a thiamine dodecyl benzenesulfonate salt represented by Chemical Formula 1 as a white solid compound.

Example 2 Synthesis of Thiamine Lauryl Sulfate

To 3.68 g (10.90 mmol) of thiamine hydrochloride (purchased from Across), 50 mL of anhydrous main column was added and stirred at room temperature to dissolve, and then 6.29 g (21.82 mmol) of sodium lauryl sulfate was added to the solution for 3 hours at room temperature. . The solution was allowed to stand at 10 ° C. for 3 hours 30 minutes to 4 hours, and then filtered under reduced pressure to obtain thiamine lauryl sulfate represented by Formula 1 as a white solid compound.

Experimental Example 1 derivatives and antimicrobial effect measurement of vitamin B _1, vitamin B ₁

In Example 1 and 22 salt substance of vitamin B ₁ species (thiamine dodecyl benjel sulfonate and thiamine lauryl sulfate) and the hydrochloride salt form of Vitamin B ₁ (thiamine hydrochloride), of the preform forms of vitamin B ₁ (thiamine) The antimicrobial effect was compared in Bacillus. The strain used was Bacillus subtilis (KCCM11316) was incubated at 37 ℃ in NB medium (Nutrient broth).

First, using the broth dilution method, the doubling dilution method of the thiamine dodecylbenzelsulfonate of Example 1 and the thiamine lauryl sulfate, thiamine hydrochloride, and thiamin of Example 1 in a broth medium suitable for the Bacillus strain 25, 12.5, 6.25, 3.125, 1.56, 0.78, 0.39 mmol concentration (mM) method, and then incubated in the culture medium in 10 ³ ~ 10 ⁴ CFU (Colony forming unit) / ml inoculated 1 ~ After 2 days of incubation, the absorbance at 570 nm was measured to obtain the minimum microbial inhibitory concentration (MIC). The results are shown in Table 1 and FIG. 1.

Minimum Microbial Inhibitory Concentration (MIC) (%) Thiamine > 25 Thiamine Dodecylbenzenesulfonate Salt 3.13 Thiamine lauryl sulfate 0.39 Thiamine Hydrochloride 12.5

As can be seen from Table 1 and Figure 1, it was confirmed that the MIC of thiamine dodecylbenzelselfonate salt and thiamine lauryl sulfate and thiamine hydrochloride of the present invention is much lower than thiamine. Through this, vitamin B ₁ has little antibacterial effect on its own, but the salt of vitamin B ₁ has excellent antibacterial effect.

Experimental Example 2 Antimicrobial Effects of Derivatives of Vitamin B ₁ on General Microorganisms

Thiamine dodecylbenzenesulfonate salt used in the composition of the present invention (obtained from Example 1 above), thiamine lauryl sulfate (obtained from Example 2 above) and thiamine hydrochloride and the disinfectant methylparaben used as a control for the following The antimicrobial effect against the 5 strains was measured using a broth dilution method to determine the minimum microbial inhibitory concentration (MIC) as follows.

At this time, Aspergillus and this (Aspergillus niger, KCCM11724) and Candida albicans (Candida albican s, KCCM11282) was cultured in PDB medium (potato dextrose broth) in 25 ℃, Staphylococcus aureus (Staphylococcus aureus, KCCM40050 ) And Pseudomonas aeruginosa (KCCM11266) were incubated at 37 ° C. in NB medium (Nutrient broth). Also, Escherichia coli , KCCM11234) were incubated at 37 ° C. in LB medium (lactose broth).

First, using the broth dilution method, the broth medium suitable for each strain, the thiamine dodecylbenzenesulfonate salt of Example 1, the thiamine lauryl sulfate salt of Example 2, thiamine hydrochloride and the control methylparaben 7.68, 3.84, 1.92, 0.96, 0.48 · · 0.007% by weight, and then inoculated at 10 ³ to 10 ⁴ CFU (Colony forming unit) / ml of each strain cultured in broth medium 2 After incubation for 3 days, the absorbance at 570 nm was measured to determine the minimum microbial inhibitory concentration (MIC), and the results are shown in Table 2 below.

Sample Name Minimum Microbial Inhibitory Concentration (MIC) (%) Aspergillus Niger Candida Albicans Staphylococcus aureus Pseudomonas aeruginosa Escherichia coli Methyl paraben 1.92 0.96 1.92 3.84 3.84 Thiamine Dodecylbenzenesulfonate Salt 0.03 0.06 0.06 0.96 0.96 Thiamine lauryl sulfate 0.03 0.015 0.007 0.03 0.06 Thiamine Hydrochloride 0.06 0.12 0.03 0.48 1.92

As a result, as can be seen in Table 1, it was confirmed that the MIC for the five strains of the thiamine dodecylbenzenesulfonate salt, thiamine lauryl sulfate and thiamine hydrochloride of the present invention was much lower than the control methyl paraben. Through this, it was found that the antibacterial effect of the salt of vitamin B ₁ is superior to the methyl paraben fungicide.

Experimental Example 3 Inhibitory Effect of Dandruff

Thiamine dodecylbenzenesulfonate salt used in the composition of the present invention (obtained from Example 1 above), thiamine lauryl sulfate (obtained from Example 2 above), thiamine hydrochloride and ketoconazole used as a control as dandruff In order to measure the antimicrobial effect, the minimum microbial inhibitory concentration (MIC) was measured by the following method using a broth dilution method. At this time, as the dandruff was used Pytirosporum ovale (ATCC 14521).

First, the thiamine dodecylbenzenesulfonate salt, thiamine lauryl sulfate, and thiamine hydrochloride and the control ketoconazole in SGB (Sabouraud's Glucose broth) medium containing corn oil were prepared by 2-fold dilution method, respectively, 3.2 and 1.6. , 0.8, 0.4, 0.2, 0.1, 0.05% by weight, and inoculated in the amount of 10 ³ to 10 ⁴ CFU (colony forming unit) / ml of pytirospor ovale and incubated for 2 to 3 days, at 570 nm After measuring the absorbance to determine the minimum microbial inhibitory concentration (MIC), it is shown in Table 3.

Sample Name Minimum Microbial Inhibition Concentration (MIC,%) Ketoconazole 0.4 Thiamine Dodecylbenzenesulfonate Salt 0.8 Thiamine lauryl sulfate 0.2 Thiamine Hydrochloride 0.05

As a result, as can be seen in Table 3, the MIC for dandruff of thiamin lauryl sulfate and thiamin hydrochloride of Example 2 of the present invention is much lower than the control ketoconazole, the thiamine dode of Example 1 of the present invention It was confirmed that the silbenzenesulfonate salt also exhibited low MIC.

Examples of the formulation of the composition will be described below, but the present invention is not intended to be limited thereto, but is intended to be described in detail.

Formulation Example 1 Preparation of Shampoo

Thiamine dodecylbenzelsulfonate salt ................. 1.00 (%)

Cocamidopropyl Betaine ..................... 8.0 (%)

Cocoyl diethanolamide ............... 0.5 (%)

Disodium ethylenediaminetetraacetic acid .............. 0.1 (%)

Propylene Glycol ...................... 4.0 (%)

Hydroxypropyltrimonium chloride .............. 0.2 (%)

Polyquaternium-10 ............... 0.5 (%)

Sodium Lauryl Sulfate ............ 30.0 (%)

Sodium lauryloxyethylene sulfate ..... 30.0 (%)

Ethylene Glycol Monostearate ..... 1.0 (%)

Titanium Dioxide ............... 0.05 (%)

Methylchloroisothiazolinone ......... 0.01

The whole amount was 100 with purified water, and the shampoo was prepared by the above compounding ratio.

As described above, the components that are effective in preventing or treating dandruff in the composition according to the present invention are environmentally and ecologically friendly by using salts of vitamin B ₁ which is a naturally derived substance, unlike conventional dandruff inhibitors, It can increase the solubility in water at the same time without any safety problems, and it is an excellent bactericidal effect, especially the effect of inhibiting the growth and activity of Pyrosporum ovale , an dandruff bacterium, is an excellent effect to prevent or treat dandruff. There is.

Claims (11)

Thiamine dodecylbenzenesulfonate salt represented by following formula (1). [Formula 1] Thiamine lauryl sulfate represented by the following formula (2). [Formula 2]

Containing a salt of at least one vitamin B ₁ selected from the group consisting of thiamine dodecylbenzenesulfonate salt represented by the following formula (1), thiamine lauryl sulfate represented by the following formula (2), and thiamine hydrochloride represented by the following formula (3) Dandruff prevention or treatment composition, characterized in that. [Formula 1]

[Formula 2]

[Formula 3]

A composition for preventing and treating dandruff, comprising a salt of vitamin B ₁ including at least one selected from the group consisting of sulfate group, carbonyl group, and vinyl group. The composition for preventing or treating dandruff according to claim 3 or 4, wherein the composition inhibits the proliferation and activity of the Pityrosporum ovale strain, which is an dandruff bacterium. The composition for preventing or treating dandruff according to claim 3 or 4, wherein the composition contains 0.001 to 1.0% by weight of a salt of vitamin B _{1 based} on the total weight of the composition. The method for preventing or treating dandruff according to claim 3 or 4, wherein the composition is a hair cosmetic composition. The dandruff according to claim 3 or 4, wherein the hair cosmetic composition has a formulation selected from the group consisting of shampoo, rinse, hair conditioner, hair tonic, hair cream, hair treatment, hair spray and hair mousse. Prophylactic or therapeutic composition. The method for preventing or treating dandruff according to claim 8, wherein the formulation is a shampoo. The composition for preventing or treating dandruff according to claim 3 or 4, wherein the composition is a pharmaceutical composition. A first step of adding anhydrous mainstream to thiamin hydrochloride and then dissolving at room temperature; A second step of adding sodium dodecylbenzenesulfonate to the solution, stirring at room temperature for 2 to 4 hours, and then standing at 10 to 40 ° C. for 3 hours 30 minutes to 4 hours; And a third step of filtering the solution under reduced pressure.

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