JP2008063271A - Antibacterial cosmetic - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an antibacterial agent for a cosmetic, used in a low adding amount and also having a low skin irritation. <P>SOLUTION: This antibacterial agent for the cosmetic contains at least one compound expressed by general formula (1) [wherein, R is a 6-30C aliphatic or alicyclic hydrocarbon group; AO is a 2-6C alkyleneoxy group; and (m), (n) are each 0, or an integer of 1 to 30 and at least one of them is not 0]. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an antibacterial agent for cosmetics, and more particularly to an antibacterial agent containing a compound having a hydroxyalkyl ether group derived from a diol.

Conventionally, in order to prevent alteration due to contamination by bacteria such as bacteria and fungi during production and use in cosmetics, benzoic acid and its salt, isopropylmethylphenol, paraoxybenzoic acid ester (paraben), phenoxyethanol, salicylic acid and its salt, Antibacterial agents such as dehydroacetic acid and its salts, benzalkonium chloride, benzethonium chloride, alkyltrimethylammonium chloride have been used. However, these antibacterial agents are irritating to the skin, and there has been a demand for safer antibacterial agents.
Thereafter, 1,2-alkanediol, which has been used as a moisturizing agent, has been proposed as an antibacterial agent having relatively low skin irritation, and it has been announced that the effect as an antibacterial agent is also excellent. (Patent Documents 1 to 4) However, these required a relatively large amount of addition and had a characteristic odor of 1,2-alkanediol.
As these improvement methods, recently, combined use with a chelating agent, combined use of two or more 1,2-alkanediols having different carbon numbers, and the like have been proposed. (Patent Documents 5 and 6 and Non-Patent Documents 1 to 3)
However, with the recent increase in the safety orientation of consumers, cosmetics with less allergic and tingling sensations and less allergenic and less irritating are desired. An antibacterial agent having an antibacterial effect and low skin irritation is desired.
Japanese Patent Laid-Open No. 11-322591 JP 2001-48720 A JP-A-10-53510 JP 11-310506 A JP 2004-307484 A JP 2005-15467 A FRAGRANCE JOURNAL 2006-4 P34 FRAGRANCE JOURNAL 2006-4 P47 FRAGRANCE JOURNAL 2006-4 P68

  The present invention is intended to provide a cosmetic antibacterial agent having a low additive amount and low skin irritation.

As a result of intensive studies to solve the above problems, the present inventors have reached the present invention.
That is, the present invention is a cosmetic antibacterial agent containing at least one compound represented by the general formula (1), and a cosmetic containing 0.01 to 3% by weight of the antibacterial agent.

  In the formula, R is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms; AO is an alkyleneoxy group having 2 to 6 carbon atoms; m and n are 0 or an integer of 1 to 30, and at least one of them is It is not zero.

  The antibacterial agent for cosmetics of the present invention is excellent in antibacterial properties and has low skin irritation. Therefore, the amount to be added to the cosmetic is small, and the cosmetic has low skin irritation.

  The antibacterial agent for cosmetics of this invention contains 1 or more types of the compound shown by General formula (1), Preferably 2 or more types, More preferably, 3-10 types are contained.

In the general formula (1), R preferably has 8 to 20 carbon atoms, more preferably 8 to 16, and when R is less than 6 carbon atoms, sufficient antibacterial properties cannot be obtained, and when the carbon number exceeds 30 carbon atoms. , Cosmetic solubility and compatibility are reduced, and it is difficult to achieve uniformity.
Examples of the aliphatic hydrocarbon group in R include a linear or branched alkyl group (n-hexyl group, n-heptyl group, n-octyl, n-decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl, 3,5,7-trimethyloctyl group, etc.) and linear or branched alkenyl groups (1-hexenyl, 1-decenyl, 6-dodecenyl, oleyl group, etc.).
Examples of the alicyclic hydrocarbon group in R include a cycloalkyl group (such as cyclohexyl), an alkylcyclohexyl group (such as propylcyclohexyl group and octylcyclohexyl group), a cycloalkylalkyl group (such as cyclohexylbutyl group and cyclohexyloctyl group), and the like. A cycloalkenyl group (2-cyclohexenyl group) etc. are mentioned.
Of these, R is preferably an aliphatic hydrocarbon group, and two or more of them may be used in combination.

  Examples of the alkyleneoxy group having 2 to 6 carbon atoms represented by AO in the general formula (1) include an ethyleneoxy group, a 1,2-propyleneoxy group, a 1,3-propyleneoxy group, a 1,2-butyleneoxy group, Examples include 1,4-butyleneoxy group and 1,6-hexyleneoxy group. Of the AOs, ethyleneoxy groups, 1,2-propyleneoxy groups, and combinations thereof are preferred from the viewpoint of antibacterial properties and skin irritation.

In the general formula (1), m and n are 0 or an integer of 1 to 30, preferably 0 or an integer of 1 to 10, and at least one of m and n is not 0, and m + n is 1 to 60, preferably Is an integer from 1 to 10.
The compound in which both m and n are 0 includes 1,2-alkanediol which is a conventionally known antibacterial agent, but is insufficient in antibacterial properties and low skin irritation as described above.
A compound in which both m and n are 0 has a 1,2-diol group as a hydrophilic group at the end of the molecule, but the antibacterial agent of the present invention has at least 1 as shown in the general formula (1). It contains a hydrophilic group with two hydroxyalkyl ether groups (—O— (AO) —H).
It has traditionally been said that microorganisms need a minimum amount of water to grow.
In the 1,2-diol group, a hydroxyl group is present at an adjacent carbon atom and the occupied volume of the hydrophilic group is relatively small. However, the antibacterial agent represented by the general formula (1) has a hydrophilic group by having a hydroxyalkyl ether group. As the distance between the hydroxyl groups increases and the distance between the hydroxyl groups increases, it is estimated that a large amount of water of hydration that cannot be obtained with the 1,2-diol group is required, and the growth of microorganisms is suppressed because it deprives the microorganisms of water. The
Further, in a system having a very high water content, a hydrophilic group having at least one hydroxyalkyl ether group (—O— (AO) —H) as shown in the general formula (1) rather than a 1,2-diol group is used. It is presumed that the microorganism has a higher adsorption power to the cell membrane surface, and easily exhibits antibacterial properties.
In the antibacterial agent of the present invention, the hydrophobic group (R in the general formula (1)) has a preferable carbon number, and as described above, preferably has 8 to 20 carbon atoms, more preferably 8 to 16 carbon atoms. In this range of carbon number, it is presumed that it is convenient for destruction of the cell membrane because it is easily adsorbed on the cell membrane of microorganisms.

Moreover, it is preferable that the antibacterial agent of this invention contains 2 or more types of compounds shown by General formula (1).
When two or more types are included, there may be two or more types with different R, two or more types with different A, and two or more types with different m + n.
Among these, 2 or more types with different R and 2 or more types with different m + n are preferable, 2 or more types with different m + n are more preferable, 3 or more types with different m + n are particularly preferable, and 3 to 10 different types are particularly preferable. It is preferable to have.
By having two or more different m + n types, a synergistic effect is exhibited, antibacterial properties are improved, skin irritation is reduced, and the antibacterial spectrum tends to be broadened.

  When the antibacterial agent for cosmetics of the present invention contains two or more compounds having different m + n of the compound represented by the general formula (1), the alkylene oxide is usually added to the 1,2-diol represented by the general formula (2). Is an alkylene oxide adduct obtained by addition reaction.

  In the formula, R is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms.

The alkylene oxide adduct is usually a mixture of two or more kinds of compounds having a distribution of the number of added moles of alkylene oxide and different numbers of added moles.
In the present invention, the average addition mole number of alkylene oxide per molecule of 1,2-diol is preferably 0.5 to 10, more preferably 0.5 to 5, and particularly preferably 0.5 to 2.
If the average number of added moles is 0.5 or more, the antibacterial property is easily exerted and the skin irritation is sufficiently low. Moreover, if the average number of added moles is 10 or less, the antibacterial property is sufficiently exerted.
The number of moles of alkylene oxide added in each compound constituting the mixture is preferably 1 to 30, more preferably 1 to 20, and particularly preferably 1 to 10.

A compound having 0 addition moles, that is, less unreacted 1,2-diol is preferable. However, when a relatively small number of moles of alkylene oxide is added to 1,2-diol, unreacted 1, 2-diol tends to remain.
The content of unreacted 1,2-diol is preferably less than 50% by weight, more preferably 40% by weight or less, particularly preferably based on the weight (100% by weight) of the obtained alkylene oxide adduct. 30% by weight or less. If it is less than 50% by weight, the effects of the present invention are easily exerted, the odor is small, and it is preferable from the viewpoints of antibacterial properties, low skin irritation and hypoallergenicity.
Even if less than 50% by weight of unreacted 1,2-diol remains, if the alkylene oxide adduct coexists, the overall antibacterial properties tend to exhibit the effect of the alkylene oxide adduct.
Similarly, with regard to skin irritation, even when unreacted 1,2-diol is contained, the skin irritation tends to be canceled by the alkylene oxide adduct.

  The alkylene oxide adduct of 1,2-diol can be produced by a usual alkylene oxide addition reaction.

For example, 1,2 diol represented by the general formula (2) may be added to an alkaline catalyst (alkali metal hydroxide, alkaline earth metal hydroxide, alkaline earth metal oxide, etc.) or acid catalyst (sulfuric acid, hydrochloric acid, etc.). Inorganic acids, Lewis acids such as BF ₃ ), and the like, and a reaction is performed while injecting a predetermined amount of alkylene oxide at a temperature of 90 to 180 ° C. and a pressure of 0.3 MPa or less.
Further, a specific catalyst in the production method described in JP-A No. 2002-114844 (an acid having an acid strength H ₀ by Hammett acidity function H ₀ of −30.0 to −11.0 or a metal salt thereof, and Schrodinger's wave equation Or a strong acid salt of a metal having the lowest empty orbit in -10 to -3).

The distribution of the number of added moles of alkylene oxide can be measured under the following conditions by liquid chromatography after reacting a sample with an excess of phenyl isocyanate (special reagent grade) to label hydroxyl groups.
Model: LC-10ADVP manufactured by Shimadzu Corporation
Column: μ-Porasil (Waters)
Mobile phase: 2% isopropyl alcohol / butyl chloride
Gradient detector up to 32% isopropyl alcohol / butyl chloride; UV (240 nm)
Temperature: 40 ° C
From the ratio of the value obtained by dividing the peak area of each added mole number by the molecular weight of the corresponding added mole number compound, the weight ratio of each added mole number can be known, and the weight% can be calculated based on the ratio. .

  The antibacterial agent for cosmetics of the present invention is a mixture of two compounds of a compound represented by the general formula (1) wherein m is 1 and n is 0 and a compound where m is 0 and n is 1. In general, low molecular weight diols (2 to 6 carbon diols such as ethylene glycol, propylene glycol and butylene glycol) and long chain aliphatic 1,2-epoxy compounds (for example, 1,2-epoxydodecane, etc.) For example, it can be produced by the method described in JP-A No. 2003-96435.

  The antibacterial agent of the present invention is usually solid or liquid at 25 ° C., and is preferably liquid from the viewpoint of ease of handling.

The cosmetic of the present invention comprises the above-described antibacterial agent for cosmetics of the present invention as an essential component.
The cosmetics of the present invention are usually further oils, silicone compounds, alcohols, gelling agents, anionic surfactants, nonionic surfactants, amphoteric surfactants, cationic surfactants, chelating agents, pH adjustments. It is obtained by mixing and stirring arbitrary components selected from cosmetic raw materials such as agents, refreshing agents, whitening agents, moisturizing agents, conditioning agents, fragrances and coloring agents.

  Examples of the oil include olive oil, soybean oil, rapeseed oil, beef tallow, lard, lanolin, stearic acid, and liquid paraffin.

  Examples of the silicone compound include silicone resin, methylphenylpolysiloxane, methylpolysiloxane, octamethylcyclotetrasiloxane, dimethylsiloxane / methyl (polyoxyethylene) siloxane copolymer, decamethylcyclopentanesiloxane, dimethylsiloxanemethyl ( Polyoxyethylene / polyoxypropylene) siloxane copolymer, methylhydrogenpolysiloxane, dodecamethylcyclohexasiloxane, methylpolycyclosiloxane, dimethylsiloxane / methylstearoxysiloxane copolymer, methylpolysiloxane emulsion, octamethyltrisiloxane , Cyclic silicon resin, highly polymerized methylpolysiloxane, tetradecamethylhexasiloxane, trimethylsiloxysilicate, etc. It is.

  Examples of the alcohols include monohydric alcohols (methanol, ethanol, isopropyl alcohol, n-butyl alcohol, lauryl alcohol, stearyl alcohol, etc.), 2-6 polyhydric alcohols (ethylene glycol, diethylene glycol, triethylene glycol, Polyethylene glycol, propylene glycol, dipropylene glycol, 1,3-butanediol, diglycerin and sorbitol) and cholesterol.

  Examples of the gelling agent include sucrose palmitate, dextrin stearate, monobenzylidene sorbitol, N-lauroyl-L-glutamic acid, and the like.

  Examples of the anionic surfactant include hydrocarbon ether carboxylic acids having 8 to 24 carbon atoms or salts thereof, [sodium (poly) oxyethylene lauryl ether acetate, disodium (poly) oxyethylene lauryl sulfosuccinate, etc.], carbon Hydrocarbon sulfate salts of formula 8-24 [sodium lauryl sulfate, sodium (poly) oxyethylene lauryl sulfate, (poly) oxyethylene lauryl sulfate triethanolamine, (poly) oxyethylene coconut oil fatty acid sodium monoethanolamide sulfate, ], C8-24 hydrocarbon sulfonate [sodium dodecylbenzenesulfonate, etc.] and C8-24 hydrocarbon phosphate ester [sodium lauryl phosphate, (poly) oxyethylene lauryl ether phosphorus Acid sodium etc.], Fatty acid salts [sodium laurate, triethanolamine laurate, etc.], acylated amino acid salts [coconut oil fatty acid methyl taurine sodium, coconut oil fatty acid sarcosine sodium, coconut oil fatty acid sarcosine triethanolamine, N-coconut oil fatty acid acyl -L-glutamic acid triethanolamine, N-coconut oil fatty acid acyl-L-glutamic acid sodium, lauroylmethyl-β-alanine sodium, etc.].

  Examples of the nonionic surfactant include aliphatic alcohols (8 to 24 carbon atoms) alkylene oxide (2 to 8 carbon atoms) adducts, (poly) oxyalkylene (2 to 8 carbon atoms) higher fatty acids (8 carbon atoms). To 24) ester [polyethylene glycol monostearate], polyethylene glycol distearate, etc., polyvalent (divalent to 10-valent or more) alcohol fatty acid (carbon number 8 to 24) ester [glyceryl monostearate, monostearic acid Ethylene glycol, sorbitan monolaurate, etc.], (poly) oxyalkylene (2 to 8 carbon atoms) polyvalent (2 to 10 valent or higher) alcohol higher fatty acid (8 to 24 carbon atoms) ester [polyoxyethylene monolaurate] Sorbitan, polyoxyethylene dioleic acid methyl glucoside, etc.], Fatty acid alkanolamides [1: 1 type coconut oil fatty acid diethanolamide, 1: 1 type lauric acid diethanolamide, etc.], (poly) oxyalkylene (2 to 8 carbon atoms) alkyl (1 to 22 carbon atoms) phenyl ether, ( Poly) oxyalkylene (2 to 8 carbon atoms) alkyl (8 to 24 carbon atoms) amino ether and alkyl (8 to 24 carbon atoms) dialkyl (1 to 6 carbon atoms) amine oxide [lauryl dimethylamine oxide and the like] It is done.

  Examples of the amphoteric surfactant include betaine-type amphoteric surfactants [coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryl. Hydroxysulfobetaine, lauroylamidoethylhydroxyethylcarboxymethylbetaine hydroxypropyl phosphate sodium and the like], and amino acid type amphoteric surfactants [sodium β-laurylaminopropionate and the like].

Examples of the cationic surfactant include tetraalkyl (C1 to C18) ammonium salts (except those exemplified as antibacterial agents other than the antibacterial agent of the present invention described later), alkyl (C1 to C4). ) Higher fatty acid aminoalkyl sulfate (2 to 4 carbon atoms) trialkyl (1 to 4 carbon atoms) ammonium salt [(such as ethyl lanolin sulfate fatty acid aminopropylethyldimethylammonium)] and the like.
Further, anionic surfactants, amphoteric surfactants, cationic surfactants and nonionic surfactants described in US Pat. No. 4,331,447 are also included.

Examples of the chelating agent include edetic acid, polyphosphoric acid, pyrophosphoric acid, gluconic acid, and salts thereof.
Examples of the pH adjuster include potassium carbonate, sodium hydrogen carbonate, ammonium hydrogen carbonate, lactic acid, succinic acid, citric acid and the like.
Examples of the refreshing agent include L-menthol and camphor.

  Examples of the whitening agent include glutathione, hydroquinone, hydroquinone derivatives, resorcin, resorcin derivatives, and globrene.

  Examples of the humectant include glycerin, polyethylene glycol, sorbitol, sodium lactate, sodium pyrrolidonecarboxylate, sodium hyaluronate, chondroitin sulfate, and the like.

  Examples of the conditioning agent include cationized cellulose, cationized guar gum, silicones, polyethylene glycol, sodium polyacrylate, hydroxyethyl cellulose, protein derivatives, ceramides, pseudoceramides having a weight average molecular weight in the range of 5 to 5 million, 18 -Linear or branched fatty acids having 16 to 40 carbon atoms such as methyl eicosane, hydroxy acids, panthenol and the like.

  Examples of the perfume include d-limonene, β-caryophyllene, cis-3-hexenol, linalool, farnesol, β-phenylethyl alcohol, 2,6-nonadienal, citral, α-hexylcinnamaldehyde, β-ionone, l-carvone, cyclopentadecanone, linalyl acetate, benzylbenzoate, γ-undecalactone, eugenol, rose oxide, indole, phenylacetaldehyde dimethyl acetal, auran thiol, symamic aldehyde, methyl ionone musk, anise essential oil, silica Skin essential oil, jasmine essential oil, etc. are mentioned.

  Examples of the colorant include Blue No. 1, Blue No. 2, Green No. 3, Red No. 1 and the like, and all those that can be used for cosmetics can be used.

The preferred contents of the above optional components in the components other than water in the cosmetic of the present invention are as follows.
The oil agent, silicone compound, alcohol, anionic surfactant, nonionic surfactant, amphoteric surfactant, cationic surfactant and humectant are each preferably 50% by weight or less, more preferably 30% by weight or less. It is.
The chelating agent, gelling agent, whitening agent and conditioning agent are each preferably 20% by weight or less, more preferably 10% by weight or less.
The pH adjusting agent, the refreshing agent, the fragrance and the coloring agent are each preferably 10% by weight or less, more preferably 5% by weight or less.

Moreover, you may use together antibacterial agents other than the antibacterial agent of this invention with the cosmetics of this invention as needed. Antibacterial agents other than the antibacterial agent of the present invention include, for example, benzoic acid and its salts, salicylic acid and its salts, dehydroacetic acid and its salts, isopropylmethylphenol, paraben, 2-phenoxyethanol, quaternary ammonium salts (benzalkco chloride). Nium, benzethonium chloride, alkyltrimethylammonium chloride, etc.), polyhexamethylene biguanilide, chlorhexidine glucuronate, polylysine, and 2- (4-thiocyanomethylthio) benzimidazole.
The ratio of the combined use when the antibacterial agent other than the antibacterial agent of the present invention is used in combination is 100 parts by weight or less, preferably 50 parts by weight or less with respect to 100 parts by weight of the antibacterial agent of the present invention.

The cosmetic product of the present invention is preferably contained so that the content of the antibacterial agent of the present invention is 0.01 to 3% by weight in the cosmetic product, more preferably 0.01 to 2% by weight, particularly 0.01%. It is preferable to contain so that it may become -0.8weight%.
The cosmetic of the present invention is preferably contained so that the content of the antibacterial agent of the present invention is 0.01 to 5% by weight in components other than water in the cosmetic, more preferably 0.01 to The content is preferably 3% by weight, particularly 0.01 to 1.5% by weight.

  The content of water in the cosmetic of the present invention is appropriately selected depending on the type of cosmetic, but is usually 99% by weight or less, preferably 0 to 98% by weight, based on the weight of the cosmetic. Moreover, the solid content concentration (ratio of components other than water) of the cosmetic of the present invention is usually 1 to 100% by weight, preferably 2 to 100% by weight.

  The specific use of the cosmetic product of the present invention is not particularly limited. For example, basic cosmetics such as milky lotion, cream, lotion, cleansing agent, etc .; cleansing agents such as face wash, whole body cleaner, shampoo; hair treatment, rinse, Hair conditioners such as conditioners, hair restorers and hair nourishing agents; makeup cosmetics such as foundations, lipsticks and eye shadows; and odorants.

<Example>
EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these. Hereinafter, the part means part by weight.
The distribution of the number of added moles of alkylene oxide in (A) was measured under the following conditions by the liquid chromatography described above after the sample was reacted with excess phenyl isocyanate (special reagent grade) to label the hydroxyl groups.
Model: LC-10ADVP manufactured by Shimadzu Corporation
Column: μ-Porasil (Waters)
Mobile phase: 2% isopropyl alcohol / butyl chloride
Gradient detector up to 32% isopropyl alcohol / butyl chloride; UV (240 nm)
Temperature: 40 ° C
The ratio of the value obtained by dividing the peak area of each added mole number by the molecular weight of the corresponding added mole number compound is defined as the weight ratio of each added mole number, and the weight percent of each added mole number is calculated based on that ratio. Calculated.

Example 1
Into a glass autoclave with stirring and temperature control functions, 202 parts (1, 1 part by mole) of 1,2-dihydroxydodecane and 0.1 part of potassium hydroxide were added, and the inside of the mixed system was replaced with nitrogen. (About 20 mmHg) and dehydration were performed at 120 ° C. for 1 hour. Next, 30.8 parts (0.7 mol parts) of EO was introduced at 150 ° C. so that the gauge pressure was 1 to 3 kgf / cm 2. 3 parts of “Kyoward 600” was added to the reaction product, and the catalyst was adsorbed at 90 ° C., followed by filtration to obtain a 1,2-diol alkylene oxide adduct (A-1).
The added mole number distribution of (A-1) is shown in Table 1.

Example 2
In a glass autoclave with stirring and temperature control functions, 174 parts (1 mole part) of 1,2-dihydroxydecane and 0.1 part of aluminum perchlorate 9 hydrate were added, and the inside of the mixed system was replaced with nitrogen. Thereafter, dehydration was performed at 120 ° C. for 1 hour under reduced pressure (about 20 mmHg). Subsequently, 55.0 parts (1.25 mol parts) of EO were introduced at 95 ° C. so that the gauge pressure was 1 to 2 kgf / cm 2. 2 parts of “Kyoward 500 (manufactured by Kyowa Chemical Industry Co., Ltd.)” was added to the reaction product, and after the catalyst was adsorbed at 90 ° C., the 1,2-diol alkylene oxide adduct (A-2) of the present invention was filtered. Got.
The added mole number distribution of (A-2) is shown in Table 1.

Examples 3 to 6 and Comparative Example 1
The same procedure as in Example 1 was conducted except that the type and amount of 1,2-diol as a raw material, the amount of potassium hydroxide as a catalyst, and the type and amount of alkylene oxide were changed as shown in Table 1. The 1,2-diol alkylene oxide adducts (A-3) to (A-6) and (X-1) of Examples 3 to 6 and Comparative Example 1 were obtained. These added mole number distributions are shown in Table 1.
Abbreviations in Table 1 are as follows.
6D: 1,2-dihydroxy-n-hexane 8D: 1,2-dihydroxy-n-octane 10D: 1,2-dihydroxy-n-decane 12D: 1,2-dihydroxy-n-dodecane 16D: 1,2- Dihydroxy-n-hexadecane 24D: 1,2-dihydroxy-n-tetraeicosane EO: ethylene oxide PO: 1,2-propylene oxide

(A-1) to (A-6), and (X-1), 10D (1,2-dihydroxy-n-decane), 12D (1,2-dihydroxy-n-dodecane), paraben as comparisons And 2-phenoxyethanol were used to evaluate antibacterial and skin irritation. The test method is as follows, and the results are shown in Table 2.

<Antimicrobial properties>
Antibacterial properties were evaluated by the minimum inhibitory concentration (MIC) test. In other words, Heart infusion broth (HIB) was used as a medium, and measurement was performed according to a dilution method (reference; microbial science practical training edited by the Institute of Medical Science, University of Tokyo). The above antibacterial agents or these blends were diluted with HIB to prepare a solution having a concentration of 25 ppm to 0.39 ppm. 50 μl of an overnight culture solution of the test strain Escherichia coli (medium; number of HIB bacteria 10 ° C. CFU / ml) was added and cultured overnight at 37 ° C. Thereafter, the minimum inhibitory drug concentration (MIC) for observing the growth of the test bacteria to grow was determined.

<Skin irritation>
The antibacterial agent was evaluated for skin irritation by a closed batch test (48 hours later, inside the upper arm) by 5 men and women, and evaluated according to the following criteria.
0: No erythema 1: Very mild erythema 2: Clear erythema 3: Medium to strong erythema 4: Meat-like erythema

The following cosmetics were prepared using the antibacterial agent of the present invention or the antibacterial agent of the comparative example, and the skin irritation was evaluated.
<Emollient emulsion (O / W type)>
Squalane 5.0
Glycerin 4.0
Polyoxyethylene (20) glyceryl triisostearate 2.0
PEG-6000 0.5
Antibacterial agent 0.1
Fragrance 0.1
Purified water Balance squalane, glycerin and polyoxyethylene (20) glyceryl triisostearate are stirred while heating to 70 ° C to prepare an oil phase, and other components are heated to 70 ° C and dissolved in another container. The aqueous solution was added to the oil phase with stirring and emulsified.

The obtained emollient emulsion was actually used by 10 women, and the tingling feeling after use was evaluated according to the following criteria.
0: Not tingling at all 1: Slightly tingling 2: Slightly tingling

<Moisturizing cream>
Squalane 12.0
Jojoba oil 4.2
Paraffin 3.0
Behenyl alcohol 2.2
1,3-butylene glycol 3.2 3.2
Stearic acid 4.0
Cetanol 2.0
Polyoxyethylene (15) glyceryl monostearate 2.0
Antibacterial agent 0.3
Purified water balance

The obtained moisturizing cream was actually used by 10 women, and the tingling sensation after use was evaluated according to the following criteria.
0: Not tingling at all 1: Slightly tingling 2: Slightly tingling

  The antibacterial agent of the present invention can be used as an antibacterial agent for various uses such as cosmetics, pharmaceuticals, beverages, wood and plastics. In particular, cosmetics, for example, basic cosmetics such as emulsions, creams, lotions, cleansing agents, etc .; cleansing agents such as facial cleansers, whole body cleaners, shampoos, etc .; Useful in makeup cosmetics such as lipsticks and eye shadows;

Claims (7)

An antibacterial agent for cosmetics comprising at least one compound represented by the general formula (1).

Wherein R is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms; AO is an alkyleneoxy group having 2 to 6 carbon atoms; m and n are 0 or an integer of 1 to 30, and at least one of them Is not 0.) The antibacterial agent for cosmetics according to claim 1, comprising two or more compounds represented by the general formula (1). The antibacterial agent for cosmetics according to claim 1 or 2, which is an alkylene oxide adduct obtained by addition reaction of alkylene oxide with 1,2-diol represented by the general formula (2).

(In the formula, R is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms.) The antibacterial agent for cosmetics according to claim 3, wherein the average addition mole number of alkylene oxide per molecule of 1,2-diol in the alkylene oxide adduct is 0.5 to 10. The antibacterial agent for cosmetics according to claim 3 or 4, wherein the content of unreacted 1,2-diol is less than 50% by weight based on the weight of the alkylene oxide adduct. A cosmetic comprising 0.01 to 3% by weight of the antibacterial agent for cosmetics according to any one of claims 1 to 5. In addition, benzoic acid and its salts, salicylic acid and its salts, dehydroacetic acid and its salts, isopropylmethylphenol, paraben, 2-phenoxyethanol, quaternary ammonium salts, polyhexamethylene biguanide, chlorhexidine glucuronate, polylysine and 2- ( The cosmetic according to claim 6, comprising at least one antibacterial agent selected from the group consisting of 4-thiocyanomethylthio) benzimidazole.