JP4734293B2 - Antiseptic disinfectant and human body composition - Google Patents

Description

  The present invention relates to an antiseptic disinfectant and a composition applied to the human body, and its purpose is to eliminate or reduce the amount of antiseptic disinfectants conventionally used such as parabens and benzoic acid, and to have excellent antibacterial activity. It is an object of the present invention to provide a highly safe human body application composition having a small amount or no compounding of a conventional antiseptic disinfectant and a conventional antiseptic disinfectant. In addition, in this specification, a human body application composition is a composition applied directly to the inside or the outside of the human body, such as cosmetics, pharmaceuticals, quasi drugs, and foods.

  Conventionally, parabens, benzoic acid and salts thereof, salicylic acid and salts thereof, and the like are used as antiseptic fungicides in compositions applied to human bodies such as cosmetics, pharmaceuticals, quasi drugs, and foods. However, the above-mentioned conventional antiseptic disinfectants have a drawback that the use concentration range is easily restricted because of low safety such as high skin irritation. For example, the use restriction concentration of paraben and benzoate is 1 %, The limit concentration of benzoic acid and salicylic acid is 0.2%. In addition, since it is easily affected by pH, the stability of the effect is poor, and further, there is a problem that the antibacterial activity may be remarkably lowered by the combined use with other compounding components such as surfactant. . In recent years, the number of people who have an allergic reaction to these antiseptics has increased. Therefore, the direction toward safety has increased, and no antiseptics or antiseptics have been added, or the amount applied has been reduced. There is an increasing demand for compositions.

  Therefore, various attempts have been made to overcome the disadvantages of conventional antiseptics and to reduce the amount of antiseptics used by searching for highly safe antibacterial substances and increasing the effectiveness of antiseptics. . For example, a plurality of antiseptic disinfectants are used, and the amount of the antiseptic disinfectant used is reduced by utilizing a synergistic effect thereof. Furthermore, the effectiveness of conventional antiseptic disinfectants depends on the amount present in the aqueous phase, but since many of them have low solubility in water, polyhydric alcohols such as 1,3-butylene glycol, dipropylene glycol and glycerin. In order to increase the distribution of the antiseptic disinfectant to the aqueous phase, the effect of the antiseptic disinfectant is also increased.

  However, the combined use of polyhydric alcohols such as 1,3-butylene glycol, dipropylene glycol, and glycerin with a conventional antiseptic disinfectant is not significant in the antibacterial activity of the antiseptic disinfectant. The antiseptic sterilization effect of the hydric alcohol itself is exhibited when it is blended in a large amount, for example, when 1,3-butylene glycol or dipropylene glycol is blended at 10% or more, and glycerin is blended at 30% or more. However, the amount of conventional antiseptic disinfectants used has not been significantly reduced.

  On the other hand, it has already been reported that Photosensitive Element 201 (Pionin) has an excellent antibacterial activity as a highly safe and stable antibacterial substance. Since Photosensitive Element 201 has extremely low solubility in water and alcohol, when Photosensitive Element 201 is used as an antiseptic disinfectant, it is usually a polyhydric alcohol such as 1,3-butylene glycol, dipropylene glycol, or glycerin. Is used as a solubilizer.

  However, even if Photosensitive Element 201 is used as an antiseptic disinfectant, the amount of conventional antiseptic disinfectant used has not been significantly reduced or eliminated. In other words, photosensitizer No. 201 has a slightly weaker antibacterial activity against gram-negative bacteria than antibacterial activity against gram-positive bacteria, and is extremely superior in antibacterial activity against gram-negative bacteria when used in combination with an antiseptic disinfectant such as paraben. In general, when using Photosensitive Element 201, a conventional antiseptic disinfectant such as paraben is currently used together, and the amount of conventional antiseptic disinfectant used is This has not led to a significant reduction or elimination.

  Therefore, it is hoped to create an antibacterial agent having excellent antibacterial activity that can provide a highly safe composition for human body application by eliminating or reducing the amount of antiseptic agents used conventionally. It is rare. As a result of intensive studies on antiseptic fungicides, the present inventors have determined 1,2-hexanediol, 1,2-octanediol, etc. in addition to 1,2-pentanediol, which has been conventionally used as a moisturizing agent. By using the included 1,2-alkanediol having 4 to 10 carbon atoms as a solubilizer of Photosensitive Element 201, the antibacterial activity of Photosensitive Element 201 can be enhanced. -Alkanediol itself has excellent antibacterial activity, and by using it as a preservative disinfectant in human body composition, the antibacterial activity of conventionally used antiseptic disinfectant is enhanced and the amount of antiseptic disinfectant used It has been found that the conventional antiseptic disinfectant can be eliminated and the present invention has been completed.

  That is, the invention according to claim 1 relates to an antiseptic disinfectant characterized by comprising 1,2-alkanediol having 4 to 10 carbon atoms and Photosensitive Element 201.

  The invention according to claim 2 is characterized in that the 1,2-alkanediol is at least one of 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol. The antiseptic disinfectant according to claim 1.

  Furthermore, the invention which concerns on Claim 3 is related with the human body application composition characterized by mix | blending the antiseptic disinfectant of Claim 1 or 2 as an antiseptic disinfectant.

  As described in detail above, the invention according to claim 1 relates to an antiseptic disinfectant characterized by comprising 1,2-alkanediol having 4 to 10 carbon atoms and Photosensitive Element 201. The following effects are obtained.

  That is, since 1,2-alkanediol has extremely superior antibacterial activity compared to other polyhydric alcohols, this 1,2-alkanediol is blended in a human body composition as an antiseptic disinfectant. This makes it possible to reduce or eliminate the amount of the antiseptic disinfectant having various drawbacks used conventionally. By combining such a 1,2-alkanediol and Photosensitive Element 201 and using it as an antiseptic disinfectant, 1,2-alkanediol not only becomes a solubilizer for Photosensitive Element 201, but also has a synergistic effect. Since each antibacterial power is enhanced by the above, it is possible to reduce or eliminate the amount of antiseptic disinfectant used conventionally. In addition, 1,2-alkanediol is highly safe and excellent in moisture retention. Accordingly, it is possible to provide a composition for human body application that is imparted with antiseptic sterilization properties and is highly safe and excellent in use feeling.

  The invention according to claim 2 is characterized in that the 1,2-alkanediol is at least one of 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol. Since it is related to the antiseptic disinfectant according to claim 1, the following effects can be obtained.

  That is, 1,2-alkanediol has extremely superior antibacterial activity compared to other polyhydric alcohols, and in particular, 1,2-pentanediol is effective against 1,2-hexanediol and general bacteria. Since 1,2-octanediol further exhibits an excellent antiseptic sterilization effect against yeast and mold, by blending these 1,2-alkanediols as antiseptic sterilizers into human body compositions, It is possible to further reduce or eliminate the use amount of the antiseptic disinfectant having various drawbacks.

Furthermore, the invention according to claim 3 relates to a human body composition comprising the antiseptic disinfectant according to claim 1 or 2 as an antiseptic disinfectant. Therefore, the antiseptic disinfectant is high and safe. The effect that it is excellent also in a property and a usability | use_condition is produced.
By using 1,2-alkanediol in combination with conventionally used antiseptics such as benzoic acid and salts thereof, phenoxyethanol, 4-isopropyl-3-methylphenol, etc. Since each antibacterial power is improved by the synergistic effect, the amount of the antiseptic disinfectant used conventionally can be greatly reduced. Moreover, if it is set as the human body application composition whose compounding quantity of the said phenoxyethanol is less than 0.2 weight% in a composition, there is no irritation | stimulation with respect to skin and there exists an effect that a usability | use_condition is very good.

  As described above, the present inventors have used antiseptic sterilization conventionally used by using 1,2-alkanediol having 4 to 10 carbon atoms and Photosensitive Element 201 as an antiseptic sterilizing agent for human body composition. It has been found that the agent can be eliminated or the amount used can be reduced, and the present invention has been completed. That is, in the present invention, 1,2-alkanediol having 4 to 10 carbon atoms and No. 201 photosensitive element are used as antiseptic disinfectants.

  1,2-alkanediol is a substance represented by the following formula 1 (chemical formula 1), specifically 1,2-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2- Heptanediol, 1,2-octanediol, 1,2-nonanediol, and 1,2-decanediol (wherein n represents an integer of 1 to 7 in Formula 1).

  In particular, as is clear from the test examples described later, 1,2-pentanediol represented by the following formula 2 (Chemical formula 2) exhibits an excellent antibacterial action against general bacteria, and the following formula 3 (Chemical formula 3) 1,2-hexanediol represented by formula (1) and 1,2-octanediol represented by the following formula 4 (formula 4) are preferable because they exhibit excellent antibacterial activity against general bacteria, fungi such as yeast and mold. Used. One of these 1,2-alkanediols may be used alone, but it is of course possible to use a mixture of two or more.

  Among the 1,2-alkanediols described above, 1,2-pentanediol is a kind of polyol that has been widely used as a cosmetic base, and has high safety and is readily soluble in water. It is used as an agent, stabilizer, dispersant, solvent, etc. Accordingly, the use of 1,2-pentanediol also increases the moisturizing power, so that the preparation can be made excellent in moist feeling. In addition, as is clear from the test examples described later, even when other polyhydric alcohols such as 1,2-hexanediol and 1,2-octanediol are used, the preparation should be similarly excellent in moist feeling. Can do.

  As is apparent from the results of the safety test described later, 1,2-alkanediol is extremely high in safety, so that it can be added to the human body composition up to 20% by weight. However, if it is less than 0.05% by weight, the antiseptic sterilization effect due to the 1,2-alkanediol blending is not sufficiently exerted, so the blending ratio in the composition is 0.05-20% by weight, especially 1,2- When using pentanediol, the content is desirably 1 to 10% by weight.

  As described above, 1,2-alkanediol has an excellent antibacterial activity, but the antibacterial activity is determined from the results of the minimum growth inhibitory concentration (hereinafter referred to as MIC) in the test examples described later. , The MIC of 1,2-alkanediol is larger than the MIC of the antibacterial agents such as paraben and benzoate, that is, the antibacterial activity of 1,2-alkanediol. Is small compared to antiseptics such as parabens and benzoates. However, since 1,2-alkanediol is extremely safe as will be apparent from the results of the safety test described later, it can be incorporated in the composition for human body application up to 20% by weight. That is, even if the antibacterial activity is small, sufficient antibacterial activity can be exerted by increasing the blending amount. As a result, by using 1,2-alkanediol, a conventionally used antiseptic disinfectant Can provide a sufficient antibacterial property to the human body composition without using it at all, and provides a human body composition excellent in safety and antibacterial properties can do.

  In addition, 1,2-alkanediol is used as a preservative fungicide in combination with Photosensitive Element 201 (Pionine). This Photosensitive Element 201 is a yellow crystal powder represented by the following formula 5 (Chemical Formula 5), which has high safety and excellent antibacterial properties, and thus has been conventionally used as an antiseptic disinfectant for human body compositions. Has been.

  Since Photosensitive Element 201 has extremely low solubility in water and alcohol, solubilizing agents are usually used when blended in cosmetics and the like, but when used in combination with 1,2-alkanediol having antibacterial activity, 1 , 2-alkanediol serves as a solubilizing agent for Photosensitive Element 201 and its antibacterial activity is enhanced by a synergistic effect. Therefore, in the past, when Photosensitive Element 201 was used, a preservative disinfectant such as paraben was often used in combination with a solubilizer, but by using 1,2-alkanediol in combination, It is possible to reduce the amount of the antiseptic sterilizing agent such as paraffin, and to exhibit a sufficient antiseptic sterilizing effect without using any conventional antiseptic sterilizing agent such as paraben. Furthermore, since the amount of the photosensitive element 201 used can be reduced, even if the blending amount of the photosensitive element 201 in the human body composition is less than 0.002% by weight, a sufficiently excellent antiseptic sterilizing effect is exhibited. be able to. Of course, the solubilizer of Photosensitive Element 201 may be a conventionally used solubilizer, and 1,2-alkanediol may be blended as an antiseptic disinfectant.

  In the present invention, the 1,2-alkanediol, benzoic acid represented by the following formula 6 (Chemical formula 6) and salts thereof, phenoxyethanol represented by the following formula 7 (Chemical formula 7), and the following formula 8 (Chemical formula 8) It is also possible to use in combination with conventionally used antiseptics such as 4-isopropyl-3-methylphenol shown (wherein R in formula 6 represents H or Na).

  When 1,2-alkanediol and a conventional antiseptic disinfectant are used in combination, the antibacterial activity is enhanced by a synergistic effect and excellent antiseptic properties against all types of bacteria regardless of the type of general bacteria or fungi Bactericidal action is demonstrated. For example, when 1,2-pentanediol is used alone, it exhibits an excellent antiseptic sterilization effect against general bacteria, but hardly exhibits an antiseptic sterilization effect against fungi. When an antiseptic disinfectant is used in combination, an excellent antiseptic disinfecting effect is exerted against fungi. Therefore, the usage-amount of the antiseptic | preservative used conventionally can be reduced significantly, and the human body application composition excellent in safety | security can be provided.

  When a conventional antiseptic fungicide such as benzoic acid and its salt, phenoxyethanol, 4-isopropyl-3-methylphenol, and 1,2-alkanediol are used in combination, benzoic acid, its salt, phenoxyethanol, 4-isopropyl- The compounding quantity of 3-methylphenol is not specifically limited, What is necessary is just to set it as a use restriction | limiting density | concentration or less. However, when blended in the human body composition, if the blending amount of phenoxyethanol is 0.2 wt% or more in the composition, the irritation to the skin becomes strong and the feeling of use deteriorates, so the blending amount of phenoxyethanol is The content is preferably less than 0.2% by weight in the composition. In addition, even if the blending amount of phenoxyethanol is less than 0.2% by weight in the composition, each antiseptic power is enhanced by the combined use with 1,2-alkanediol. It can be demonstrated.

  The composition for human body application according to the present invention contains the above-described 1,2-alkanediol and Photosensitive Element 201 as antiseptic fungicides, and benzoic acid and its salts, phenoxyethanol, 4-isopropyl-3-methylphenol and the like are appropriately used. It is a composition formed by blending. For example, skin and hair cosmetics such as facial cleansers, lotions, emulsions, creams, shampoos, hair treatments, medicinal cosmetics (quasi-drugs) with specific uses such as prevention of stains and freckles, and acne treatment The above-mentioned antiseptic disinfectant can be blended in pharmaceuticals intended for such purposes as well as foods, etc. to obtain the human body application composition according to the present invention.

  As described above, 1,2-alkanediol used in the present invention is an extremely safe substance. Hereinafter, the safety of 1,2-alkanediol will be described based on test results.

(Toxicity test) As a result of oral acute toxicity test and dermal acute toxicity test of 1,2-pentanediol using 10 rats of 5 males and 5 females, 50% lethal dose (LD ₅₀ ) It was 5000 mg / Kg in the case of oral administration and 2000 mg / Kg in the case of transdermal administration.

(Irritation test) Acute skin irritation tests for 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol were conducted for 3 samples of male and female, 6 rabbits in total. And the acute eye irritation test was performed using 6 male rabbits and 3 female rabbits for each sample. As a result, there was almost no skin and eye irritation in any of the samples. . Further, in the skin sensitization test with 10 males and 10 females, a total of 20 guinea pigs, there was almost no irritation to the skin.

  Further, the results of human skin compatibility test, mutagenicity test, and patch test for 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol were all negative. From the results of the above safety test, it can be said that 1,2-alkanediol including 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol is an extremely safe substance. .

<Test Examples> The present invention will be described in detail below based on test examples.
[Test Example 1: Measurement of minimum growth inhibitory concentration (MIC)] 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol, which are 1,2-alkanediols, -The antibacterial activity of 1,2-alkanediol was evaluated by measuring the MIC of 1,3-butylene glycol, dipropylene glycol, and glycerin, which are one of polyhydric alcohols as well as alkanediol.

(Test method) A 12% aqueous solution and an 8% aqueous solution were prepared for each of the above six types of polyhydric alcohols, and a serial dilution series of twice each was prepared. (12,6,3,1.5,0.75 ...% and 8,4,2,1,0.5 ...%) Escherichia coli IFO3972 (Escherichia coli) and Staphylococcus aureus IFO13276 (Staphylococcus aureus), and these bacteria are pre-cultured in bouillon medium for about 20 hours, assuming that the culture solution is 10 ⁸ cells / ml, and is about 10 ⁵ cells / ml. The diluted one was used as a bacterial suspension. The number of bacteria was confirmed by the colony count method. 1.4 ml each of the sample solution and SCD medium adjusted to various concentrations were placed in a 15 ml test tube that had been sterilized by dry heat. To this, 70 μl of the bacterial suspension was inoculated so as to be 10 ³ cells / ml, and cultured at 35 ° C. for 24 hours. The growth of the bacteria was judged visually, and the lowest concentration at which the growth of the bacteria was completely prevented was defined as the MIC value.

  The results are shown in Table 1.

  From the results of Table 1, 1,2-pentanediol is 2-5%, 1,2-hexanediol is 0.75-3%, 1,2-octanediol is 0.15-0.3%. It can be seen that the growth of E. coli and S. aureus is suppressed, whereas the three polyhydric alcohols of 1,3-butylene glycol, dipropylene glycol and glycerin do not suppress the growth of bacteria even at 6%. That is, 1,2-alkanediols such as 1,2-pentanediol, 1,2-hexanediol and 1,2-octanediol have extremely superior antibacterial activity compared to other polyhydric alcohols. It can be said. Therefore, by blending 1,2-alkanediol as a preservative fungicide in a human body composition, sufficient antiseptic properties are imparted to the human body composition even if the conventional antiseptic agent is eliminated or the amount used is reduced. Therefore, a highly safe human body application composition can be obtained.

[Test Example 2 Preservative Strength Test 1 in Formulation] Cream containing 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 1,3-butylene glycol, dipropylene glycol and glycerin And the antiseptic power was evaluated by a challenge test.

(Test method) First, creams of Examples 1 to 3 and Comparative Examples 1 to 3 were prepared according to the formulations shown in Table 2.

As a test bacterium, a mixed bacterial solution of Escherichia coli IFO3972 (E. coli), Staphylococcus aureus IFO13276 (Staphylococcus aureus) and Bacillus subtilis IFO12210 (Bacillus subtilis) was used as a general bacterium. Further, Saccharomyces cerevisiae IFO0234 (beer yeast) was used as yeast, and Aspergillus niger IFO9455 (black mold) was used as mold. The culture solution in which these bacteria are pre-cultured is diluted to about 10 ⁸ cells / ml for common bacteria, about 10 ⁷ cells / ml for S. cerevisiae, and about 10 ⁶ cells / ml for A. niger. This was used as a bacterial suspension. The number of bacteria was confirmed by the colony count method.

  20 g of the cream of Examples 1 to 3 or Comparative Examples 1 to 3 is put into a glass container that has been sterilized by dry heat, 0.2 ml of the above-mentioned bacterial suspension is inoculated, and the mixed bacteria are at 35 ° C., S. cerevisiae and A. niger was cultured at 25 ° C. 1 and 7 days after inoculation for mixed bacteria and S. cerevisiae, and 7, 14, and 21 days for A. niger, 1 g of each sample was taken out and diluted with physiological saline into the agar medium. For 48 hours, and the number of remaining bacteria in the sample was calculated. As for A.niger, measurement after confirming complete death was omitted.

  The results are shown in Table 3 and FIGS.

尚、表３中１，２−ＰＤは１，２−ペンタンジオールを、１，２−ＨＤは１，２−ヘキサンジオールを、１，２−ＯＤは１，２−オクタンジオールを、１，３−ＢＧは１，３−ブチレングリコールを、ＤＰＧはジプロピレングリコールを示し、＊は測定を省略したことを示す。（以下、表５，７，９，１０，１２に関しても同じ）
また図１は混合菌の生菌数の変化を表す図、図２はS.cerevisiaeの生菌数の変化を表す図、図３はA.niger の生菌数の変化を表す図であり、図中○印の折れ線が実施例１の結果、□印の折れ線が実施例２の結果、△印の折れ線が実施例３の結果、■印の折れ線が比較例１の結果、▲印の折れ線が比較例２の結果、●印の折れ線が比較例３の結果である。

In Table 3, 1,2-PD is 1,2-pentanediol, 1,2-HD is 1,2-hexanediol, 1,2-OD is 1,2-octanediol, 1,3 -BG represents 1,3-butylene glycol, DPG represents dipropylene glycol, and * represents that measurement was omitted. (The same applies to Tables 5, 7, 9, 10, and 12 below)
FIG. 1 is a diagram showing the change in the number of viable bacteria in the mixed bacteria, FIG. 2 is a diagram showing the change in the number of live bacteria in S. cerevisiae, and FIG. 3 is a diagram showing the change in the number of live bacteria in A. niger. In the figure, the broken line marked with ○ is the result of Example 1, the broken line with □ is the result of Example 2, the broken line with Δ is the result of Example 3, the broken line with ■ is the result of Comparative Example 1, and the broken line is marked with ▲. Is the result of Comparative Example 2, and the broken line with ● is the result of Comparative Example 3.

  From the results shown in Table 3 and FIGS. 1 to 3, 1,2-pentanediol shows a sufficient antiseptic power with a decrease in the number of bacteria over time for general bacteria and yeasts. Almost no antiseptic power is observed, and it can be seen that 1,2-hexanediol and 1,2-octanediol exhibit a sufficient antiseptic power against general bacteria, yeasts and molds. On the other hand, it can be seen that other polyhydric alcohols hardly exhibit preservative power against any of general bacteria, yeasts and molds. That is, without using any conventional antiseptic disinfectant, even if only 1,2-pentanediol is used as an antiseptic disinfectant, excellent antiseptic power is exhibited against general bacteria and yeasts. When hexanediol and 1,2-octanediol are used as an antiseptic disinfectant, an excellent antiseptic power is further exhibited against mold. Therefore, by using these 1,2-alkanediols as antiseptic disinfectants, conventional antiseptic disinfectants can be eliminated, and highly safe human body application compositions can be obtained.

[Test Example 3; Preservative Strength Test 2 in Formulation] Next, creams of Examples 4 to 7 and Comparative Examples 4 to 6 were prepared according to the formulation shown in Table 4, and the same challenge test as in Test Example 2 was performed. The antiseptic power when 1,2-alkanediol and phenoxyethanol were used in combination was evaluated.

図４は混合菌の生菌数の変化を表す図、図５はS.cerevisiaeの生菌数の変化を表す図、図６はA.nigerの生菌数の変化を表す図である。但し、図中○印の折れ線が実施例４の結果、□印の折れ線が実施例５の結果、△印の折れ線が実施例６の結果、▲印の点線折れ線が実施例７の結果、■印の折れ線が比較例４の結果、●印の折れ線が比較例５の結果である。

4 is a diagram showing changes in the viable count of mixed bacteria, FIG. 5 is a diagram showing changes in the viable count of S. cerevisiae, and FIG. 6 is a diagram showing changes in the viable count of A. niger. However, in the figure, the broken line marked with ○ is the result of Example 4, the broken line with □ is the result of Example 5, the broken line with Δ is the result of Example 6, the dotted broken line with ▲ is the result of Example 7, The broken line with the mark is the result of Comparative Example 4, and the broken line with the mark ● is the result of Comparative Example 5.

  From the results of Table 5 and FIGS. 4 to 6, when glycerin and phenoxyethanol are used in combination as in Comparative Examples 4 and 5, even if 0.5% by weight of phenoxyethanol is added, it is almost antiseptic for general bacteria. Although not effective, when 1,2-pentanediol and phenoxyethanol are used in combination as in Examples 4 and 7, even if the amount of phenoxyethanol used is reduced, it exhibits excellent antiseptic power against general bacteria, and yeast It can be seen that the antiseptic power of the same level or higher is exhibited. Further, as in Examples 5 and 6, when 1,2-hexanediol or 1,2-octanediol is used in combination with phenoxyethanol, the antiseptic power is improved for all bacterial species such as general bacteria, yeast and mold. It can be seen that the preservative power is remarkably superior to the case of adding 0.5 wt% of phenoxyethanol as in Comparative Example 5.

[Test Example 4; Preservative Strength Test 3 in Formulation] The creams of Examples 8 to 10 and Comparative Examples 7 to 9 were prepared according to the formulation shown in Table 6, and the same challenge test as in Test Example 2 was performed. The antiseptic power when 2-alkanediol and sodium benzoate were used in combination was evaluated.

The results are shown in Table 7 and FIGS. In addition, since the polyhydric alcohol was not mix | blended about the comparative example 9, since a component did not disperse | distribute and the result was not able to be obtained, the result about the cream of Examples 8-10 and Comparative Examples 7-8 was obtained. Show.

図７は混合菌の生菌数の変化を表す図、図８はS.cerevisiaeの生菌数の変化を表す図、図９はA.nigerの生菌数の変化を表す図である。但し、図中○印の折れ線が実施例８の結果、□印の折れ線が実施例９の結果、△印の折れ線が実施例１０の結果、■印の折れ線が比較例７の結果、●印の折れ線が比較例８の結果である。

FIG. 7 is a diagram showing a change in the viable count of mixed bacteria, FIG. 8 is a diagram showing a change in the viable count of S. cerevisiae, and FIG. 9 is a diagram showing a change in the viable count of A. niger. In the figure, the broken line marked with ○ is the result of Example 8, the broken line marked with □ is the result of Example 9, the broken line marked with △ is the result of Example 10, the broken line marked with ■ is the result of Comparative Example 7, and the ● mark The broken line is the result of Comparative Example 8.

  From the results of Table 7 and FIGS. 7 to 9, when glycerin and sodium benzoate are used in combination as in Comparative Examples 7 and 8, even if 0.3% by weight of sodium benzoate is added, general bacteria and yeast , Molds did not show any antiseptic effect on fungi, but when 1,2-pentanediol and sodium benzoate were used in combination as in Example 8, the amount of sodium benzoate used was reduced. However, it can be seen that it exhibits excellent antiseptic power against general bacteria. Further, as in Examples 9 and 10, when 1,2-hexanediol or 1,2-octanediol is used in combination with sodium benzoate, the antiseptic power is improved for all bacterial species of general bacteria, yeasts and molds. As shown in Comparative Example 8, it can be seen that the preservative power is remarkably superior to the case where 0.3% by weight of sodium benzoate is blended.

[Test Example 5: Preservative Strength Test 4 in Formulation] Creams of Examples 11 to 13 and Comparative Examples 10 to 12 were prepared according to the formulation shown in Table 8, and the same challenge test as in Test Example 2 was performed. -The antiseptic power when alkanediol and 4-isopropyl-3-methylphenol were used in combination was evaluated.

  The results are shown in Table 9 and FIGS. In addition, since the polyhydric alcohol was not mix | blended about the comparative example 12, since a component did not disperse | distribute and a result was not able to be obtained, the result about the cream of Examples 11-13 and Comparative Examples 10-11 is shown. Show.

図１０は混合菌の生菌数の変化を表す図、図１１はS.cerevisiaeの生菌数の変化を表す図、図１２はA.niger の生菌数の変化を表す図である。但し、図中○印の折れ線が実施例１１の結果、□印の折れ線が実施例１２の結果、△印の折れ線が実施例１３の結果、■印の折れ線が比較例１０の結果、●印の折れ線が比較例１１の結果である。

FIG. 10 is a diagram showing the change in the number of viable bacteria in the mixed bacteria, FIG. 11 is a diagram showing the change in the number of live bacteria in S. cerevisiae, and FIG. 12 is a diagram showing the change in the number of live bacteria in A. niger. However, in the figure, the broken line marked with ○ is the result of Example 11, the broken line marked with □ is the result of Example 12, the broken line marked with △ is the result of Example 13, the broken line marked with ■ is the result of Comparative Example 10, and the ● mark The broken line is the result of Comparative Example 11.

  From the results of Table 9 and FIGS. 10 to 12, when glycerin and 4-isopropyl-3-methylphenol were used in combination as in Comparative Examples 10-11, 0.1 weight of 4-isopropyl-3-methylphenol was used. %, The antibacterial effect was not shown against any of general bacteria, yeasts, and molds, whereas 1,2-pentanediol and 4-isopropyl-3-form were used as in Example 11. It can be seen that when methylphenol is used in combination, even if the amount of 4-isopropyl-3-methylphenol used is reduced, it exhibits excellent antiseptic power against general bacteria. Further, as in Examples 12 and 13, when 1,2-hexanediol or 1,2-octanediol and 4-isopropyl-3-methylphenol are used in combination, for all bacterial species of general bacteria, yeasts and molds Thus, it can be seen that the antiseptic power is improved, and the antiseptic power is significantly superior to the case where 0.1% by weight of 4-isopropyl-3-methylphenol is blended as in Comparative Example 11. Further, when 4-isopropyl-3-methylphenol and 1,2-alkanediol are used in combination, 4-isopropyl-3-methylphenol is used more than when 4-isopropyl-3-methylphenol is used alone as in Comparative Example 12. It can be seen that even if the amount of 3-methylphenol used is reduced, more excellent antiseptic power can be exhibited.

[Test Example 6: Combined Test 1 with Photosensitive Element 201] Antibacterial activity was measured when 1,2-pentanediol or 1,3-butylene glycol was used as a solubilizer for Photosensitive Element 201.

(Test method) First, Photosensitizer 201 was solubilized using 1,2-pentanediol or 1,3-butylene glycol to prepare four types of sample solutions. As test bacteria, Escherichia coli IFO3972 (Escherichia coli), Staphylococcus aureus 209P (Staphylococcus aureus), pathogenic bacteria MRSA OJ 51, and Aspergillus niger (Black mold) were used. 10 ml of a liquid medium containing samples of various concentrations was placed in a 30 ml vial serving also as a heat measurement cell, and then the bacterial suspension was inoculated so that the number of inoculated bacteria was 10 ⁶ cells / ml. This was installed in a calorimeter maintained at 30 ° C., and a heat generation signal accompanying the growth of microorganisms was observed. From the observed heat production signal, an algorithm calculated 50% inhibitory concentration (Ki) and 100% inhibitory concentration (MIC). The results are shown in Table 10.

  From the results shown in Table 10, when 1,2-alkanediol such as 1,2-pentanediol is used as a solubilizing agent for Photosensitive Element 201, the antibacterial activity of Photosensitive Element 201 can be increased. As shown, the antibacterial properties are superior to those obtained when 1,3-butylene glycol is used. Therefore, sufficient antibacterial power can be obtained even if the amount of the conventional antiseptic disinfectant is reduced or not used at all.

[Test Example 7: Combination Test 2 with Photosensitive Element 201] Creams of Examples 14 to 16 and Comparative Examples 13 to 14 were prepared according to the formulation shown in Table 11, and the same challenge test as in Test Example 2 was conducted. , 2-Alkanediol and Photosensitizer 201 were used together to evaluate the antiseptic power.

  The results are shown in Table 12 and FIGS.

図１３は混合菌の生菌数の変化を表す図、図１４はS.cerevisiaeの生菌数の変化を表す図、図１５はA.niger の生菌数の変化を表す図である。但し、図中○印の折れ線が実施例１４の結果、□印の折れ線が実施例１５の結果、△印の折れ線が実施例１６の結果、■印の折れ線が比較例１３の結果、●印の折れ線が比較例１４の結果である。

FIG. 13 is a diagram showing a change in the viable count of mixed bacteria, FIG. 14 is a diagram showing a change in the viable count of S. cerevisiae, and FIG. 15 is a diagram showing a change in the viable count of A. niger. In the figure, the broken line marked with ○ is the result of Example 14, the broken line with □ is the result of Example 15, the broken line with Δ is the result of Example 16, the broken line of ■ is the result of Comparative Example 13, and the ● mark The broken line is the result of Comparative Example 14.

  From the results of Table 12 and FIGS. 13 to 15, when glycerin and Photosensitizer 201 are used in combination as in Comparative Examples 13 and 14, a general antibacterial effect is shown, but yeast and For fungi, even when 0.002% by weight of Photosensitive Element 201 is added, no antiseptic effect is shown, whereas 1,2-alkanediol and Photosensitive Element 201 are used as in Examples 14-16. When used in combination, it can be seen that excellent antiseptic power is exhibited against yeast and mold. Therefore, by using Photosensitive Element 201 and 1,2-alkanediol in combination, even if the usage amount of Photosensitive Element 201 is reduced, sufficient antiseptic power can be exhibited, and highly safe human body application. A composition can be obtained.

  From the results of Test Examples 1 to 7, the use of 1,2-alkanediol having 4 to 10 carbon atoms eliminates the use of conventionally used antiseptics or reduces the amount used, so that the composition applied to the human body It is clear that a sufficient antibacterial property can be imparted to a product, and a human body composition excellent in safety and antibacterial properties can be provided.

[Test Example 8; Usability Evaluation] Next, the usability was evaluated using a hair styling cream and a massage cream.
(About moist feeling) According to the following prescription, a hair styling cream containing 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, or glycerin as a polyhydric alcohol according to a conventional method Prepared.
Hairdressing cream (wt%)
Methylpolysiloxane 5.00
Paraffin 10.00
POE sorbitan monostearate 3.30
Carboxyvinyl polymer 0.22
Triethanolamine 0.20
Polyhydric alcohol 5.00
Benzoic acid 0.10
Perfume appropriate amount UV absorber appropriate amount
Remaining purified water Total 100.00

Moreover, according to the following prescription, the massage cream which mix | blended 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, or glycerin as a polyhydric alcohol was prepared by the conventional method.
Massage cream (wt%)
Beeswax 15.00
Liquid paraffin 30.00
POE sorbitan monostearate 3.30
Sorbitan monostearate 3.30
Carboxyvinyl polymer 0.02
Triethanolamine 0.15
Polyhydric alcohol 3.00
Liquid isoparaffin 30.00
Benzoic acid 0.10
Perfume
Remaining purified water Total 100.00

Each of 10 female hairdressing creams and massage creams prepared according to the above prescriptions was used, and the usability was sensorially evaluated from the viewpoint of moist feeling. Based on the results of sensory evaluation, the determination was made according to the following criteria.
◎: Eight or more out of 10 people judged to have moist feeling ○; 5 out of 10 people judged to have moist feeling ×; 4 or less of 10 people judged to have moist feeling

The results are shown in Table 13.

(Irritating feeling) According to the formulation of Table 14, massage creams of Examples 17 to 21 and Comparative Example 15 were prepared by a conventional method.

Each of the six types of massage creams was used by 10 women, and the sensory evaluation was performed on the feeling of use from the viewpoint of a sense of irritation. Based on the results of sensory evaluation, the determination was made according to the following criteria.
◎: No one in 10 feels a stimulus ○: 1-3 out of 10 are judged to be stimulated x; More than 4 out of 10 are judged to be a stimulus

  The results are shown in Table 15.

表１３及び表１５の結果より、１，２−ペンタンジオール，１，２−ヘキサンジオール，１，２−オクタンジオールといった１，２−アルカンジオールが配合されたクリームは保湿力においても優れており、しかも極めて刺激性が低いことがわかる。

From the results of Table 13 and Table 15, creams containing 1,2-alkanediol such as 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol are excellent in moisturizing power, Moreover, it can be seen that the irritation is extremely low.

<Prescription Example> Hereinafter, a prescription example of the human body application composition according to the present invention will be shown.
(Prescription Example 1)
Lotion (wt%)
Polyethylene glycol 1500 2.00
1,2-hexanediol 2.00
Polyoxyethylene oleyl ether (25E.O25) 1.50
Perfume appropriate amount sodium benzoate 0.10
UV absorber
Remaining purified water Total 100.00

(Prescription example 2)
Shampoo (% by weight)
Lauryl polyoxyethylene sulfate sodium salt 30.00
(30% aqueous solution)
Lauryl sulfate sodium salt (30% aqueous solution) 10.00
Palm oil fatty acid diethanolamide 4.00
1,2-pentanediol 3.00
Fragrance Appropriate amount Dye Appropriate amount Phenoxyethanol 0.15
Chelating agent
Remaining purified water Total 100.00

(Prescription Example 3)
Acne prevention facial cleanser (wt%)
Stearic acid 10.00
Palmitic acid 10.00
Myristic acid 12.00
Lauric acid 4.00
Coconut oil 1.50
Polyoxyethylene lauryl ether 2.00
Glycerol monostearate 2.00
1,2-octanediol 1.00
Glycerin 10.00
Photosensitive element 201 0.001
Benzoic acid 0.10
Chelating agent appropriate amount perfume appropriate amount dye appropriate amount
Remaining purified water Total 100.00

(Formulation Example 4) Acne prevention cream (wt%)
Stearyl alcohol 8.00
Stearic acid 3.00
Purified lanolin 6.00
1,2-hexanediol 1.00
Glycerin 3.00
Glycerol monostearate 2.00
Polyoxyethylene cetyl alcohol ether 3.00
Isopropylmethylphenol 1.00
Sodium benzoate 0.10
Perfume proper amount antioxidant proper amount
Remaining purified water Total 100.00

(Prescription Example 5)
Orange juice <br/> Orange essence 3.0g
Citrus juice 10.0g
110.0g of sugar
1,2-pentanediol 2.0g
Citric acid 5.5g
2000ml water

(Prescription Example 6)
Foaming agent for cake (wt%)
Beef tallow monoglyceride 4.60
Sorbitan monostearate 6.90
Polyglycerin ester 11.50
70% sorbitol 30.00
1,2-octanediol 1.00
Perfume
Water 42.00
Total 100.00

It is a figure showing the change of the number of living bacteria of the mixed bacteria in Test Example 2. It is a figure showing the change of the viable count of S. cerevisiae in Test Example 2. It is a figure showing the change of the viable count of A.niger in Test Example 2. It is a figure showing the change of the number of viable bacteria of the mixed bacteria in Test Example 3. It is a figure showing the change of the viable count of S. cerevisiae in Test Example 3. It is a figure showing the change of the viable count of A.niger in Test Example 3. It is a figure showing the change of the number of living bacteria of the mixed bacteria in Test Example 4. It is a figure showing the change of the viable count of S. cerevisiae in Test Example 4. It is a figure showing the change of the viable count of A.niger in Test Example 4. It is a figure showing the change of the number of viable bacteria of the mixed bacteria in Test Example 5. It is a figure showing the change of the viable count of S. cerevisiae in Test Example 5. It is a figure showing the change of the viable count of A.niger in Test Example 5. It is a figure showing the change of the number of living bacteria of the mixed bacteria in Test Example 7. It is a figure showing the change of the viable count of S. cerevisiae in Test Example 7. It is a figure showing the change of the viable count of A.niger in Test Example 7.

Claims (3)

In an antiseptic disinfectant comprising photosensitive element 201 represented by the following formula 2 (chemical formula 2) as an active ingredient, 1,2-pentanediol represented by the following formula 3 (chemical formula 3) and / or the following formula 4 (chemical formula 4) antiseptic disinfectant, characterized in that it comprises the 1,2-hexanediol represented by 4).

At least 3,000 parts by mass of 1,2-pentanediol represented by Formula 3 (Chemical Formula 3) and / or 1,2-hexanediol represented by Formula 4 (Chemical Formula 4) with respect to 1 part by mass of Photosensitive Element 201 The antiseptic disinfectant according to claim 1, characterized by comprising . The antiseptic disinfectant according to claim 1 or 2 as an antiseptic disinfectant was formulated so that the compounding amount of 1,2-pentanediol and / or 1,2-hexanediol was 0.05 to 20% by mass. A human body composition characterized by the above.

Images