KR102272901B1 - Composition for external application to the skin containing meso-2,3-butanediol as a preservative - Google Patents

Abstract

The present invention contains meso-2,3-butanediol, which is an isomer of 2,3-butanediol, represented by the following formula (1), so that it has excellent preservative power and less irritation to the skin without including a chemical preservative. It relates to an excellent composition for external application to the skin.
[Formula 1]

Description

Composition for external application to the skin containing meso-2,3-butanediol as a preservative {Composition for external application to the skin containing meso-2,3-butanediol as a preservative}

The present invention relates to a composition for external application for skin that contains meso-2,3-butanediol, which is an isomer of 2,3-butanediol, and has excellent preservative power without containing chemical preservatives and has less irritation to the skin and thus has excellent feeling of use will be.

The composition for external application for skin may be contaminated with microorganisms through various routes such as contamination by microorganisms that may be generated during the manufacturing process, contamination of bacteria by skin contact such as fingers during use, or contamination by water during use. Therefore, in order to inhibit or kill the growth of microorganisms in the composition, and to improve the preservation of the product, the formulation of a preservative or the like is required.

Commonly used preservatives include, for example, paraoxybenzoic acid esters (collectively referred to as 'parabens'), imidazolidinylurea, phenoxyethanol or chlorophenesin. These chemical preservatives may exhibit effectiveness as a preservative used in the composition for external application for skin. However, these chemical preservatives formulated in the composition may exhibit skin irritation, allergies, and the like, and in severe cases may also exhibit skin toxicity.

It is also possible to prepare a composition for external application for skin that does not contain preservatives such as parabens or phenoxyethanol. For example, aseptic manufacturing, internal content or usage period can be limited, and in some cases, complicated means such as small portions or non-refillable containers (bagless tubes, containers with dispensers, etc.) are employed. Therefore, there is a problem that it is not economical.

On the other hand, the preservative power of some diols is known. For example, in the case of 1,2-butanediol and 1,2-hexanediol, they are partially used due to their excellent preservative power. However, the use of 1,2-butanediol and 1,2-hexanediol for the preservation of external preparations such as cosmetics is limited due to safety issues such as skin irritation and irritation.

Korean Patent Publication No. 10-2003-0026065 (published on March 31, 2003)

Accordingly, the present inventors tried to find a material that can replace chemical preservatives with high irritation and poor safety for the skin, and found that meso-2,3-butanediol has excellent preservative power and low irritation to the skin. The present invention has been completed.

Accordingly, it is an object of the present invention to provide a composition for external application for skin including a preservative component having high preservative power, which can replace conventional chemical preservatives, and has high safety and feeling of use for the skin.

In order to achieve the above object, the present invention provides a composition for external application for skin containing meso-2,3-butanediol represented by the following formula (1).

The composition for external application for skin containing meso-2,3-butanediol according to the present invention exhibits sufficient preservative power without the use of chemical preservatives, which have low safety for the skin due to high irritation, while at the same time providing stability to the skin and feeling of use. It has the advantage of being excellent, and therefore it can be used in various ways in the cosmetic field.

The present invention provides a composition for external application for skin containing meso-2,3-butanediol.

2,3-butanediol is generally produced by fermentation, Klebsiella pneumoniae , Bacillus It is produced by bacteria such as polymyxa and Enterobacter aerogenes, and is also chemically synthesized using pentoses, xylose, and arabinose as raw materials.

In particular, in external preparations such as cosmetics, 2,3-butanediol has been conventionally used as a component such as an emollient, humectants or wetting agent in the composition.

2,3-butanediol can be classified into three isomers stereochemically. That is, it can be divided into meso-2,3-butanediol, S,S-2,3-butanediol, and R,R-2,3-butanediol, and their respective structures are shown in Formulas 1 to 3 below, have.

[Formula 1]

Among these three stereoisomers of 2,3-butanediol, meso-2,3-butanediol, in particular, has better antiseptic properties and lower irritation compared to other stereoisomers.

Therefore, the composition according to the present invention uses meso-2,3-butanediol, which has antibacterial activity, as a preservative as an alternative to chemical preservatives, so that chemical preservatives such as parabens, imidazolidinyl urea, phenoxy ethanol, and 1, It is possible to provide a composition with less irritation than a composition using diols such as 2-butanediol and 1,2-hexanediol. In addition, by adjusting the blending amount of meso-2,3-butanediol according to the intended use, sufficient antiseptic properties and preservative power can be secured without any chemical preservatives. In particular, when used in cosmetics, it is excellent in safety and usability for the skin. And it has better compatibility with other ingredients of cosmetics.

In the present invention, "composition for external application to the skin" is a concept that encompasses the overall composition used for external application to the skin, and includes, for example, various cosmetics such as basic cosmetics, makeup cosmetics, and hair cosmetics (including body products); Or it refers to a composition that can be widely applied to various pharmaceuticals such as ointments or quasi-drugs, and the present invention is to individually provide these types of external compositions.

In the present invention, "preservative" means that the product can be stably preserved for a long period of time by preventing the material from being deteriorated by the proliferation of contaminating microorganisms such as bacteria, mold and yeast in the product to contaminate the product, The term "preservative power" refers to the ability to prevent the product from being contaminated by surrounding contaminants such as these contaminating microorganisms and thereby preventing the material from being deteriorated.

In the present invention, in order to effectively exert an effective preservative power in the composition for external application for skin, meso-2,3-butanediol is 0.001% by weight or more, preferably 0.5% by weight or more, specifically 1.0 based on the total weight of the composition. It may be formulated in a proportion of at least 1.5 wt%, more preferably at least 1.5 wt%. In addition, in consideration of the effectiveness of the formulation as an effective content of the other components in the composition for external application for skin and the formulation of meso-2,3-butanediol, the content of meso-2,3-butanediol is 20 wt% or less, or 10 wt% or less , more preferably, it may be limited to 4% by weight or less.

The meso-2,3-butanediol used in the composition of the present invention may be prepared through a conventionally known method and blended in the composition for external application, and a commercially available product may be blended in the composition for external application.

The composition for external use in the present invention does not need to additionally blend other antibacterial agents or preservatives in the composition for external application of the present invention when only the desired effect of the present invention is considered, but is usually used in the composition for external application within a range that does not impair the above effects It is also ok to additionally mix other antibacterial agents to be used in the composition for external use of the present invention. In addition, in the composition of the present invention, as long as it does not impair the desired effect, the ingredients normally formulated in external preparations according to the properties of the external composition composition, for example, moisturizing agents, ultraviolet absorbers, vitamins, animal and plant extracts, digestive agents, whitening agents , it is possible to mix vasodilators, astringents, cooling agents, hormones, and the like.

The composition for external application for skin of the present invention may be a cosmetic composition, a pharmaceutical composition, or the like. In addition, the composition may be formulated in the form of, for example, softening lotion, astringent lotion, nourishing lotion, eye cream, nourishing cream, massage cream, cleansing cream, cleansing foam, cleansing water, powder, essence or pack. , the formulation is not particularly limited. In addition, in each formulation, other components may be appropriately selected and formulated by those skilled in the art without difficulty depending on the type or purpose of use of other compositions.

Hereinafter, the present invention will be described in more detail through preferred test examples of the present invention, but the following test examples and the like are for exemplarily confirming the effects of the present invention, and the scope of the present invention is not limited thereto.

[Formulation Examples 1-4 and Comparative Formulation Examples 1-4] Nutrient lotion (lotions)

Formulation Examples 1 to 9 and meso-2,3-butanediol containing meso-2,3-butanediol in a conventional manner according to the composition of Table 1 below, and no meso-2,3-butanediol (Comparative Formulation Example 1), or instead of conventional 1, Samples of Comparative Formulation Examples 1 to 4 were prepared in which 2-hexanediol (Comparative Formulations 2 and 3) or methylparaben (Comparative Formulation Example 4), which is a conventional chemical preservative, was added.

Raw material name Formulation example Comparative formulation example One 2 3 4 5 6 7 8 9 One 2 3 4 Purified water remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount remaining amount liquid paraffin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 glycerin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 cetyloctanoate 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 concentrated glycerin 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 cyclomethicone 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 dimethicone 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 stearic acid 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 0.8 cetostearyl alcohol 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 Glycerin Stearate 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 triethanolamine 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Carboxyvinyl Polymer 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Sodium ethylenediamine acetate 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Spices appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount appropriate amount Meso-2,3-butanediol 0.5 One 1.5 2 3 4 5 10 12 - - - _ 1,2-Hexanediol - - - - - - - - - - 0.5 One - methylparaben - - - - - - - - - - - - 0.5

[Test Example 1] Antiseptic test

Escherichia coli (Escherichia) in 20 g of the cosmetics of Formulation Examples 1 to 94 and Comparative Formulation Examples 1 to 4 in order to evaluate the preservative power coli ; ATCC 8739), Staphlyococcus aureus aureus ; ATCC 6538) and Pseudomonas aeruginosa aeruginosa ; ATCC 99027) and the like ^{were added and mixed so that the initial concentration per sample was 10 6} cfu (colony forming unit)/g. While these were cultured in a 22.5°C thermostat for 4 weeks, 1 g of each cosmetic was taken at intervals of 1, 7, 14, 21 and 28 days, and the number of viable cells was measured, and the results are shown in Table 32 below.

In the case of the fungus, Penicillium citrinum citrinum ; ATCC 9849) and Aspergillus niger (ATCC 16404) were added to an initial concentration of 10 ⁶ cfu/g per sample, mixed, and then cultured in a thermostat at 25° C. The presence or absence of mycelium and spores on the surface was observed, and the results are shown in Table 2 below.

cosmetics Bacteria (cfu/g) mold ^* Initial number of bacteria 1 day 7 days 14 days 21 days 28 days Formulation Example 1 1 × 10 ⁶ 1425 <1000 <1000 <1000 <1000 + Formulation Example 2 1 × 10 ⁶ 1324 <1000 <100 <100 <10 - Formulation Example 3 1 × 10 ⁶ <1000 <100 <10 <10 <10 - Formulation Example 4 1 × 10 ⁶ <1000 <100 <10 <10 <10 - Formulation Example 5 1 × 10 ⁶ <100 <10 <10 <10 <10 - Formulation Example 6 1 × 10 ⁶ <10 <10 <10 <10 <10 - Formulation Example 7 1 × 10 ⁶ <10 <10 <10 <10 <10 - Formulation Example 8 1 × 10 ⁶ <10 <10 <10 <10 <10 - Formulation Example 9 1 × 10 ⁶ <10 <10 <10 <10 <10 - Comparative Formulation Example 1 1 × 10 ⁶ 2200 10000 4000 3500 <1000 ++ Comparative Formulation Example 2 1 × 10 ⁶ 1250 <1000 <10 <10 <10 - Comparative Formulation Example 3 1 × 10 ⁶ 1000 100 <10 <10 <10 - Comparative Formulation Example 4 1 × 10 ⁶ <10 <10 <10 <10 <10 -

- : No odor and no mycelium and spores for 8 weeks, good

+ : Mold on the wall or lid within 4 weeks

++ : Odor and mold on a part of the surface within 4 weeks

+++ : Bad odor and mold on the entire surface within 4 weeks

Through the results of Table 2, the formulation example using meso-2,3-butanediol may exhibit an antiseptic effect, and in particular, when meso-2,3-butanediol is contained in an amount of 1.5 wt% or more (Formulation Example 3 and In 4), the preservative power of Comparative Formulation Examples 2 and 3 using the existing 1,2-hexanediol preservative was similar or superior to that of Comparative Formulation Examples 2 and 3, and meso-2,3-butanediol was contained in an amount of 4% by weight or more. In the case of (Formulation Examples 6 to 9), it can be confirmed that it exhibits a very good preservative power similar to that of Comparative Formulation Example 4 using the existing methylparaben preservative.

[Test Example 2] Usability (irritation) test

An experiment was conducted to evaluate the irritation with respect to the samples of Formulation Example 6 and Comparative Formulation Examples 1 to 4. Specifically, 0.5 ml of each of the samples of Formulation Example 6 and Comparative Formulation Examples 1 to 4 were applied to 15 panelists by changing the left and right sides at random. After rubbing the samples on the skin, irritants such as 'stinging' and 'burning' were evaluated, and the results are shown in Table 3 below.

<Evaluation Criteria>

0 - 0.4 : None

0.4 ~ 1.0 : Slight (insignificant)

1.1 ~ 2.0 : Moderate

2.1 ~ 3.0 : Severe

test substance Formulation Example 6 Comparative Formulation Example 1 Comparative Formulation Example 2 Comparative Formulation Example 3 Comparative Formulation Example 4 sting 0.19 0.20 0.32 0.38 0.92 hot flashes 0.62 0.54 0.79 0.94 0.85 Average 0.41 0.37 0.56 0.66 0.89

As shown in Table 3 above, compared to Comparative Formulation Examples 2 and 3 using the existing 1,2-hexanediol and Comparative Formulation Example 4 using the existing methylparaben preservative, a larger amount of meso-2 as a preservative, It was found that the degree of irritation in Formulation Example 6 using 3-butanediol was very low.

[Test Example 3] Skin irritation test

Meso-2,3-butanediol, S,S-2,3-butanediol, and R,R-2,3-butanediol, which are stereoisomers of 2,3-butanediol, have different hydroxy positions but are similar to 1,3-butanediol A 24-hour patch test was performed to evaluate the skin safety of butanediol, 1,2-butanediol, and 1,2-hexanediol, an existing diol, in the human body. The patch was attached to the upper back of the subject, and 20 μl of the prepared test material was applied using an IQ chamber (chemotechique, Sweeden). The patch was removed after 24 hours had elapsed after the patch was applied. The first reading was performed 30 minutes after the patch was removed, and the second reading was performed after 24 hours.

In order to find out the strength of the skin irritation of the sample, weights were given according to the degree of positive skin reaction, and the skin irritation of the sample was determined by obtaining the average skin reactivity. The skin average reactivity was calculated through Equation 1 below, and the determination criteria are shown in Table 4 below. The experimental results are shown in Table 5.

Score skin irritation intensity Less than 1 (Grade I) non-irritant 1 to less than 3 (Grade II) mild stimulation 3 or more and less than 5 (Grade III) central stimulus 5 or higher (Grade IV) strong stimulus

test substance content(%) Score Purified water 100 0.32 1,3-butanediol 30 0.52 1,2-Butanediol 30 2.48 S,S-2,3-butanediol 30 2.12 R,R-2,3-butanediol 30 1.45 Meso-2,3-butanediol 30 0.41 1,2-Hexanediol 20 2.54

In the results of Table 5, meso-2,3-butanediol showed a lower skin irritation level than 1,2-hexanediol, and the other stereoisomers S,S-2,3-butanediol, R, It was found that the skin irritation level was lower than that of R-2,3-butanediol.

Through the above test examples, the composition for external application for skin according to the present invention uses meso-2,3-butanediol, which is a stereochemically isomer, without using conventional chemical preservatives or 1,2-hexanediol. This is excellent, and at the same time, the level of skin irritation or irritation is very low compared to conventional chemical preservatives or 1,2-hexanediol, and thus the feeling of use is improved.

Claims (10)

It contains meso-2,3-butanediol represented by the following formula (1) as a preservative,
A composition for external application to the skin that does not contain S , S -2,3-butanediol or R , R -2,3-butanediol as a preservative.
[Formula 1]

The composition for external application for skin according to claim 1, wherein the content of meso-2,3-butanediol is 0.001 to 20% by weight based on the total weight of the composition. The composition for external application for skin according to claim 2, wherein the content of meso-2,3-butanediol is 1.5 to 4% by weight based on the total weight of the composition. The composition for external application for skin according to claim 1, wherein the composition uses meso-2,3-butanediol as the sole preservative. The composition for external application for skin according to claim 1, wherein the composition has little irritation to the skin. The composition for external application for skin according to any one of claims 1 to 5, wherein the composition is a cosmetic composition. A preservative comprising meso-2,3-butanediol represented by the following formula (1),
The preservative is less irritating to the skin than S , S -2,3-butanediol or R , R -2,3-butanediol,
antiseptic.
[Formula 1]

8. The method of claim 7,
The preservative is less irritating to the skin than methylparaben or 1,2-hexanediol.
A composition for external application to the skin comprising the preservative of claim 7 or 8.
The composition for external application for skin according to claim 9, wherein the amount of meso-2,3-butanediol is 0.001 to 20% by weight based on the total weight of the composition for external application for skin.