JP4091498B2 - Antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant - Google Patents

Description

  The present invention relates to an antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant. More specifically, it contains 1,2-alkanediol having 5 to 10 carbon atoms and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as active ingredients. The present invention relates to an antiseptic fungicide that synergistically enhances the antibacterial activity inherent in diol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, and a cosmetic, a pharmaceutical and a food containing the antiseptic fungicide.

  Parabens, benzoic acids, salicylic acids, and the like are used as antiseptic fungicides in cosmetics (including quasi drugs), pharmaceuticals, and foods. However, the above-mentioned conventional antiseptic disinfectant has a drawback that the concentration range in use is easily limited because of low safety such as high skin irritation. For example, the use restriction concentration of paraben and benzoate is 1%, and the use restriction concentration of benzoic acid and salicylic acid is 0.2%. Moreover, since these antiseptic disinfectants are easily affected by pH, the stability of the antiseptic disinfecting effect is poor, and the antiseptic disinfecting effect may be remarkably lowered when used in combination with other compounding ingredients such as surfactants. Also had. In recent years, the number of people who cause allergic reactions to these antiseptics has increased, so the consumer safety has become stronger. There is an increasing demand for reduced cosmetics, pharmaceuticals and foods.

  Therefore, it has been reported that 1,2-alkanediol has antibacterial activity against Escherichia coli, Staphylococcus aureus and the like as a technique related to antiseptic fungicides using 1,2-alkanediol (see Patent Document 1). ). In addition, as a technique using a combination of 1,2-alkanediol and another substance having antiseptic sterilization power, an external composition composed of 1,2-pentanediol and 2-phenoxyethanol (see Patent Document 2), 1,2 -An antiseptic disinfectant composed of alkanediol and paraben (see Patent Document 3), an external composition composed of 1,2-alkanediol and hinokitiol (see Patent Document 4), and the like are disclosed.

  On the other hand, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate is also known to have antibacterial activity, and as a technique used in combination with other substances having antiseptic sterilization power, cosmetics used in combination with hinokitiol (Patent Document 5) is disclosed.

Japanese Patent Laid-Open No. 11-322591 JP-A-10-53510 JP 11-310506 A JP 2001-48781 A JP-A-8-157322

  However, conventional technology related to antiseptics using 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate reduces the amount of antiseptics such as parabens and benzoic acids. Or in order to eliminate 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, wherein 1,2-alkanediol and N-coconut oil fatty acid acyl- No attempt has been made to further enhance the antibacterial activity inherent to L-arginine ethylpyrrolidone carboxylate.

  The present invention has been made in view of the above prior art, and when 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate are used together as active ingredients, -Antiseptic disinfectant capable of synergistically enhancing antibacterial activity inherent in alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant It is an issue to provide.

  That is, the invention according to claim 1 includes a 1,2-alkanediol having 5 to 10 carbon atoms represented by the following formula 1 (chemical formula 1) and an N-coconut oil fatty acid acyl represented by the following formula 2 (chemical formula 2). The present invention relates to an antiseptic disinfectant characterized by containing -L-arginine ethylpyrrolidone carboxylate.

（但し、ｎは２〜７の整数を示す。）

(However, n represents an integer of 2 to 7.)

（但し、ＲＣＯはヤシ油脂肪酸残基を示す。）
請求項２に係る発明は、前記１，２−アルカンジオールが、１，２−ヘキサンジオール及び／又は１，２−オクタンジオールであることを特徴とする請求項１に記載の防腐殺菌剤に関する。
請求項３に係る発明は、前記１，２−アルカンジオールが、１，２−オクタンジオールであることを特徴とする請求項１に記載の防腐殺菌剤に関する。
請求項４に係る発明は、請求項１乃至３のいずれかに記載の防腐殺菌剤を配合していることを特徴とする医薬品または食品に関する。
請求項５に係る発明は、請求項１乃至３のいずれかに記載の防腐殺菌剤を配合していることを特徴とする化粧品（但し、１，２−ペンタンジオール又は１，２−ヘキサンジオールを含有するものを除く）に関する。

(However, RCO represents a coconut oil fatty acid residue.)
The invention according to claim 2 relates to the antiseptic fungicide according to claim 1, wherein the 1,2-alkanediol is 1,2-hexanediol and / or 1,2-octanediol.
The invention according to claim 3 relates to the antiseptic fungicide according to claim 1, wherein the 1,2-alkanediol is 1,2-octanediol.
The invention according to claim 4 relates to a medicine or food characterized by containing the antiseptic disinfectant according to any one of claims 1 to 3 .
The invention according to claim 5 is a cosmetic product comprising the antiseptic disinfectant according to any one of claims 1 to 3 (however, 1,2-pentanediol or 1,2-hexanediol is added). Excluding those contained).

  According to the present invention, 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethyl pyrrolidone carboxylate have a synergistically enhanced antibacterial activity and inherently contain the antiseptic disinfectant. Cosmetics, medicines and foods can be provided.

Hereinafter, the antiseptic disinfectant according to the present invention will be described in detail. The antiseptic fungicide according to the present invention contains 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as active ingredients.
The first component of the antiseptic fungicide according to the present invention is a 1,2-alkanediol having 5 to 10 carbon atoms represented by the following formula 3 (Chemical formula 3), specifically, 1,2-pentanediol. 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol.

（但し、ｎは２〜７の整数を示す。）

(However, n represents an integer of 2 to 7.)

In the present invention, one of the above-mentioned 1,5-alkanediols having 5 to 10 carbon atoms can be used alone, or two or more kinds can be mixed and used.
1,2-alkanediol itself has excellent antibacterial activity, and has the effect of increasing the antibacterial activity of the antiseptic disinfectant according to the present invention. In particular, in the present invention, since it exhibits an excellent antibacterial action against general bacteria, yeast and the like, among 1,2-alkanediols having 5 to 10 carbon atoms, 1,2-hexanediol, 1,2-octanediol It is preferable to use 1,2-octanediol.

  The second component of the antiseptic fungicide according to the present invention is an N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate represented by the following formula 4 (Chemical formula 4).

（但し、ＲＣＯはヤシ油脂肪酸残基を示す。）
Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩は、Ｌ−アルギニンとヤシ油脂肪酸との縮合物をエタノールでエステル化し、ＤＬ−ピロリドンカルボン酸塩としたものである。このような市販のＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩としては、商品名ＣＡＥ（登録商標、味の素株式会社製）を例示することができる。

(However, RCO represents a coconut oil fatty acid residue.)
N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate is obtained by esterifying a condensate of L-arginine and palm oil fatty acid with ethanol to form DL-pyrrolidone carboxylate. As such commercially available N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, trade name CAE (registered trademark, manufactured by Ajinomoto Co., Inc.) can be exemplified.

  In the antiseptic disinfectant according to the present invention, the first component of 1,2-alkanediol having 5 to 10 carbon atoms and the second component of N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate Although content is not specifically limited, It mix | blends so that it may become 1: 10-10: 1 by weight ratio, Preferably it is 1: 5-5: 1. When 1,2-alkanediol is added in an amount exceeding 10 times the amount of N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylic acid If the salt is added in an amount exceeding 10 times the amount of 1,2-alkanediol, it is not preferable because an antibacterial activity enhancing effect cannot be expected.

  The antiseptic disinfectant according to the present invention contains 1,2-alkanediol as the first component and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as the second component. As shown in the test, the synergistic effect of the first component and the second component exerts a synergistically enhanced antiseptic and bactericidal action against bacteria such as general bacteria and mold. Therefore, it is not necessary to blend or blend a preservative antibacterial agent such as paraben, benzoic acid or salicylic acid, which has been used before, and extremely high safety can be obtained.

The antiseptic disinfectant according to the present invention described above can be used by blending it in cosmetics, pharmaceuticals, foods and the like.
Specifically, cosmetics for skin such as face wash, lotion, milky lotion, cream, foundation, mascara, nail enamel, lipstick, shampoo, hair treatment, hair nourishing and hair restorer, hair cream, hair lotion, hair foam, Hair cosmetics such as permanent wave agents, medicinal cosmetics (quasi-drugs) with specific uses such as stains and freckles, acne medicines, gargles, lozenges, chewing gum, candy, It can use suitably for foodstuffs, such as a drink.

In the case of preparing cosmetics, pharmaceuticals or foods using the antiseptic disinfectant according to the present invention, components usually used in cosmetics, pharmaceuticals or foods can be arbitrarily arbitrarily blended within the range where the effects of the present invention are not impaired. . For example, in the case of cosmetics and pharmaceuticals (including quasi drugs), fats and oils, waxes, higher fatty acids, lower alcohols, higher alcohols, sterols, fatty acid esters, humectants, surfactants, polymer compounds, inorganic pigments, dyes , Fragrances, antioxidants, ultraviolet absorbers, vitamins, astringents, whitening agents, animal and plant extracts, sequestering agents, purified water, and the like.
In the case of foods, animal and vegetable oils, polysaccharides, sweeteners, colorants, gum bases and the like can be exemplified.
When preparing cosmetics, pharmaceuticals or foods, the amount of the antiseptic disinfectant according to the present invention is not particularly limited, but is 0.01 to 20% by weight, preferably 0.05 to 5% by weight in the composition. Even if it exceeds 20% by weight, no further effect can be expected. Moreover, when it is less than 0.01% by weight, the antibacterial effect is inferior, which is not preferable.

(Bactericidal test)
As test bacteria, Staphylococcus aureus IFO13276 and black mold (Aspergillus niger IFO9455) were used.

(Preparation of bacterial solution for inoculation)
In the case of Staphylococcus aureus, the bacterial solution for inoculation was cultured on an agar medium at 35 ° C., then transplanted to a bouillon medium, and cultured at 35 ° C. A solution obtained by diluting the obtained culture solution to about 10 ⁸ cells / ml with a bouillon medium was used as a bacterial solution for inoculation.
In the case of Aspergillus niger, Tween 80 after incubated at 25 ° C. (polyoxyethylene (20) sorbitan monooleate) as prepared in about 10 ⁶ cells / ml suspension of spores 0.2 percent pressurized saline Was used as an inoculum.

(Preparation of dilution series of test substance)
A 20 w / w% ethyl cellosolve was used as a diluent solvent to prepare a 5 w / v% 1,2-octanediol liquid (mother liquid). This mother liquor was diluted twice to prepare a 10-step dilution series.
Further, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate (trade name CAE, registered trademark, manufactured by Ajinomoto Co., Inc.) and 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone Similarly, a 10-step dilution series was prepared for each of the equal weight mixtures of carboxylates.

(Measurement of minimum inhibitory concentration (MIC))
Each agar medium to which the dilution series containing the substance to be studied was added was placed in a petri dish, and the inoculum for the inoculum was streaked to a length of about 1 cm.
The culture was performed at 35 ° C. for Staphylococcus aureus, and the presence or absence of the growth of the bacteria after 2 days was determined. Moreover, about black mold, it culture | cultivated at 25 degreeC and the presence or absence of the growth of a microbe after 3 days was determined. At this time, the minimum concentration at which no growth was observed was determined as MIC. As a result, as for Staphylococcus aureus, 1,2-octanediol was 2250 μg / ml, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate was 10 μg / ml, and a mixture of both was 10 μg / ml. Met. As for black mold, 1,2 octanediol was 1250 μg / ml, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate was 625 μg / ml, and an equivalent mixture of both was 625 μg / ml.
The antibacterial activity can be evaluated by the minimum inhibitory concentration (MIC). There is no effect on microorganisms when the concentration of the test substance is low, but growth inhibition occurs when the concentration is increased. This degree of growth proceeds depending on the concentration, and finally the growth stops. The concentration at that time is expressed as MIC. Therefore, when the concentration is higher than MIC, the microorganisms are killed.

(Dual minimum inhibitory concentration)
1,2-octanediol, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate obtained, 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate, etc. Each MIC of the weight mixture was plotted against the blending amount of 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate to obtain a binary minimum inhibitory concentration diagram. The results are shown in FIGS.
In addition, the effect at the time of mix | blending two types of substances which have antimicrobial property can be determined with a binary minimum growth inhibitory density | concentration. Specifically, when two types of substances having antibacterial properties are blended, the resulting action is roughly classified into synergistic action, additive action, and antagonism. The synergistic action is an action in which two drugs act synergistically to further enhance the inherent antibacterial power. The additive action is an action in which the antibacterial powers of the respective drugs are combined. Antagonism is the action when one drug counteracts the antibacterial activity of another drug. Then, the method using the binary minimum growth inhibitory concentration is a method of determining from the graph by measuring the MIC for each of the A substance and the B substance while changing their ratios as shown in FIG. According to this, when MIC (point A) in only substance A and MIC (point B) only in substance B are connected, the MIC when both substances are used is on the inner side of this line (point C) is a synergistic effect in which antibacterial activity is enhanced by the combined use, when it is on the line (point D), when it is an additive action, when it is outside the line (point E), one or both It can be determined that the antibacterial activity is an antagonism that counteracts the antibacterial activity and decreases the antimicrobial activity.

(Evaluation of antibacterial effect)
From the results of FIG. 1 and FIG. 2, it can be seen that by combining 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, a synergistic effect of the antibacterial activity of both is recognized. .

Hereinafter, formulation examples of cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant according to the present invention will be shown.
<Formulation Example 1: Moisturizing cream>
Decaglyceryl monolaurate 1.0
Monostearic acid POE (15) glyceryl 1.0
Hydrogenated soybean phospholipid 1.0
Stearic acid 4.0
Cetanol 2.0
Behenyl alcohol 2.0
Paraffin 3.0
Squalane 12.0
Jojoba oil 4.0
Methylpolysiloxane 0.2
1,3-butylene glycol 3.0
L-Arginine 0.1
Xanthan gum 0.001
1,2-octanediol 0.25
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.10
Purified water
Total 100.0% by weight

<Formulation Example 2: Hydrophilic ointment>
Ascorbic acid 0.5
Polyoxyethylene cetyl ether 2.0
Hydrogenated soybean phospholipid 1.0
Stearic acid 4.0
Glycerol monostearate 10.0
Liquid paraffin 10.0
Vaseline 4.0
Cetanol 5.0
Propylene glycol 5.0
1,2-hexanediol 0.5
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.2
Purified water
Total 100.0% by weight

<Prescription Example 3: Beverage>
Glucose liquid sugar 33.0
Grapefruit juice 64.0
1,2-pentanediol 0.5
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.1
Fragrance 0.5
Acidulant appropriate amount
Total 100.0% by weight

2 is a binary minimum growth inhibitory concentration diagram of Staphylococcus aureus of Example 1. FIG. 2 is a binary minimum growth inhibitory concentration diagram of black mold of Example 1. FIG. It is a figure which shows an example of the method of judging the effect produced by the case where two types of substances which have antimicrobial property are mix | blended from binary minimum growth inhibitory density | concentration.

Claims (5)

A 1,2-alkanediol having 5 to 10 carbon atoms represented by the following formula 1 (Chemical formula 1), and an N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate represented by the following formula 2 (Chemical formula 2): An antiseptic disinfectant characterized by containing.

(However, n represents an integer of 2 to 7.)

(However, RCO represents a coconut oil fatty acid residue.)   The antiseptic disinfectant according to claim 1, wherein the 1,2-alkanediol is 1,2-hexanediol and / or 1,2-octanediol.   The antiseptic disinfectant according to claim 1, wherein the 1,2-alkanediol is 1,2-octanediol. A pharmaceutical or food comprising the antiseptic disinfectant according to any one of claims 1 to 3 . A cosmetic product containing the antiseptic disinfectant according to any one of claims 1 to 3 (excluding those containing 1,2-pentanediol or 1,2-hexanediol).

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