Emulsion preparation

Abstract

To provide an emulsion preparation containing a paraben, which ensures excellent dispersion of the paraben in water and is capable of maintaining a dispersed state over an extended period of time.SOLUTION: The present invention relates to an emulsion preparation containing: a component (A), a 4-hydroxybenzoate represented by formula (1) [wherein R represents an alkyl group having 5 to 8 carbon atoms] or a salt thereof, in an amount of 0.0001-50 mass%; a component (B), a fatty acid ester having an IOB value of 0.12 to 1.0, in an amount of 0.0001-40 mass%; a component (C), a surfactant other than the component (B), in an amount of 0.0001-15 mass%; and water, wherein a mass ratio (B) / (A) of the component (B) to the component (A) is 0.40-70.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an emulsifying preparation containing a 4-hydroxybenzoic acid ester or a salt thereof. [Background technology]

[0002] Parabens (also known as 4-hydroxybenzoic acid esters or paraoxybenzoic acid esters) have excellent antibacterial and antiseptic properties and are widely used as preservatives for cosmetics, pharmaceuticals, food, etc. They have also been reported to have a repellent effect against pests such as mites and slugs (Patent Document 1).

[0003] A technology has been developed to incorporate parabens into synthetic resins, thereby imparting their efficacy to the resin itself. For example, an antibacterial resin composition has been proposed that contains at least one agent selected from quaternary ammonium salts and at least one agent selected from 4-hydroxybenzoic acid ester compounds (Patent Document 2).

[0004] On the other hand, since it is difficult to knead paraben into resins for natural fibers such as feathers and cotton or ready-made products, if it is desired to impart the efficacy of paraben to these objects, one possible method is to disperse paraben in water and apply, sprinkle, spray or immerse the dispersion.

[0005] However, because parabens have low water solubility, an auxiliary agent is required to dissolve or emulsify them in water. For example, a method of adding decaglycerin mono-fatty acid ester to emulsify parabens in water has been proposed (Patent Document 3). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Publication No. 2019-069934 [Patent Document 2] Japanese Patent Application Publication No. 10-237317 [Patent Document 3] Japanese Patent Application Laid-Open No. 2002-161005 Summary of the Invention [Problem to be solved by the invention]

[0007] However, the method described in Patent Document 3 requires acidic conditions and is therefore not suitable for use in a wide range of fields.

[0008] An object of the present invention is to provide an emulsion preparation containing paraben, which has excellent dispersibility of paraben in water and can maintain the dispersed state for a long period of time. [Means for solving the problem]

[0009] As a result of extensive research into emulsion formulations of parabens, the present inventors discovered that an emulsion formulation with good dispersibility can be obtained by adding a specific fatty acid ester, a surfactant, and water to a 4-hydroxybenzoic acid ester, and thus completed the present invention.

[0010] That is, the present invention includes the following preferred embodiments. [1] Component (A) Formula (1) [ka] [wherein R represents an alkyl group having 5 to 8 carbon atoms] 0.0001 to 50 mass% of a 4-hydroxybenzoic acid ester represented by the formula (I) or a salt thereof, Component (B) 0.0001 to 40 mass% of a fatty acid ester having an IOB value of 0.12 to 1.0; Component (C) 0.0001 to 15% by mass of a surfactant other than component (B), and water Contains An emulsified preparation, wherein the mass ratio (B) / (A) of component (B) to component (A) is 0.40 to 70. [2] The emulsion formulation according to [1], wherein component (A) is n-hexyl 4-hydroxybenzoate. [3] The emulsion formulation according to [1] or [2], wherein component (B) is one or more selected from the group consisting of propylene glycol monocaprylate, isopropyl myristate, butyl stearate, ethylhexyl palmitate, cetyl ethylhexanoate, diisopropyl adipate, dibutyl sebacate, propylene glycol dicaprylate, methyl acetylricinoleate, propylene glycol dicaprate, butyl acetylricinoleate, diethylhexyl sebacate, dibutyloctyl sebacate, and glyceryl triethylhexanoate. [4] The emulsion preparation according to any one of [1] to [3], wherein component (C) is a nonionic surfactant and / or anionic surfactant. [5] The emulsion formulation according to [4], wherein the nonionic surfactant is one or more selected from the group consisting of polyoxyethylene stearyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, polyoxyethylene distyrenated phenyl ether, polyoxyethylene tristyrenated phenyl ether, and polyoxyethylene tribenzyl phenyl ether. [6] The emulsion formulation according to [4] or [5], wherein the anionic surfactant is polyoxyethylene tristyrenated phenyl ether sulfate, polyoxyethylene tristyrenated phenyl ether sulfosuccinate, and / or polyoxyethylene alkyl ether phosphate and its salt. [7] The emulsion preparation according to any one of [1] to [6], which has a turbidity reduction rate of 5% or less after being left standing at 25°C for 7 days. [8] Component (A) Formula (1) [ka] [wherein R represents an alkyl group having 5 to 8 carbon atoms] 0.0001 to 50 mass% of a 4-hydroxybenzoic acid ester represented by the formula (I) or a salt thereof, Component (B) 0.0001 to 40 mass% of a fatty acid ester having an IOB value of 0.12 to 1.0; Component (C) 0.0001 to 15 mass% of a surfactant other than component (B), and water A method for producing an emulsified preparation comprising: mixing components including component (A), component (B), and component (C) and heating the mixture to obtain a melt; and A step of mixing the melt with water under stirring to emulsify and disperse component (A) in the water. Including, The method wherein the mass ratio (B) / (A) of the component (B) to the component (A) in the emulsion preparation is 0.40 to 70. [9] A method for applying the emulsion preparation according to any one of [1] to [7] to a region or body to be treated, wherein the application is carried out by kneading, scattering, spraying, coating or impregnation.

[10] A textile product containing the emulsion preparation according to any one of [1] to [7]. [Effects of the Invention]

[0011] According to the present invention, it is possible to obtain an emulsified preparation containing a 4-hydroxybenzoic acid ester, which has excellent dispersibility in water and can maintain the dispersed state for a long period of time. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 1 shows the appearance of the emulsified preparation obtained in Example 1. [Figure 2] FIG. 1 is a diagram showing the appearance of the composition obtained in Comparative Example 1. DETAILED DESCRIPTION OF THE INVENTION

[0013] The emulsifying preparation of the present invention contains, as component (A), a 4-hydroxybenzoic acid ester represented by formula (1) or a salt thereof.

[0014] The 4-hydroxybenzoic acid ester represented by formula (1) may be one or more selected from the group consisting of n-pentyl 4-hydroxybenzoate, n-hexyl 4-hydroxybenzoate, n-heptyl 4-hydroxybenzoate, n-octyl 4-hydroxybenzoate, and 2-ethylhexyl 4-hydroxybenzoate. Among these, n-hexyl 4-hydroxybenzoate is preferred because it provides excellent dispersibility in the resulting emulsion preparation.

[0015] The 4-hydroxybenzoic acid ester represented by formula (1) or its salt used as component (A) in the emulsified preparation of the present invention may be a commercially available product, or may be, for example, a product obtained by reacting 4-hydroxybenzoic acid with an alcohol in the presence of an acid catalyst.

[0016] The salt of the 4-hydroxybenzoic acid ester represented by formula (1) used as component (A) in the emulsified preparation of the present invention is preferably an alkali metal salt or alkaline earth metal salt of the 4-hydroxybenzoic acid ester. Specific examples of the alkali metal include one or more selected from the group consisting of sodium, potassium, and lithium, and specific examples of the alkaline earth metal include magnesium and / or calcium.

[0017] The emulsified preparation of the present invention contains, as component (A), 0.0001 to 50% by mass of a 4-hydroxybenzoic acid ester represented by formula (1) or a salt thereof, preferably 0.00025 to 48% by mass, more preferably 0.01 to 45% by mass, even more preferably 1.0 to 40% by mass, still more preferably 5.0 to 35% by mass, and particularly preferably 10 to 30% by mass.

[0018] The emulsifying preparation of the present invention contains, as component (B), a fatty acid ester having an IOB value of 0.12 to 1.0.

[0019] IOB is an abbreviation for "Inorganic / Organic Balance," and is a value corresponding to the ratio of a compound's inorganic value to its organic value, and is an index that indicates the degree of polarity of an organic compound. Specifically, IOB value = inorganic value / organic value.

[0020] Regarding inorganic and organic values, based on the report by Koda et al. (see pages 11-17 of Organic Conceptual Diagram - Fundamentals and Applications, by Yoshio Koda, Sankyo Publishing, 1984), inorganic and organic values ​​are set according to the various atoms or functional groups, such as an organic value of 20 for one carbon atom in a molecule and an inorganic value of 100 for one hydroxyl group in the molecule. The IOB value of an organic compound can be calculated by adding up the inorganic and organic values ​​of all atoms and functional groups in the organic compound.

[0021] The IOB value of component (B) is 0.12 to 1.0, preferably 0.14 to 0.9, more preferably 0.16 to 0.8, and even more preferably 0.18 to 0.7. When the IOB value of component (B) is within the above range, the resulting emulsion preparation has excellent dispersibility.

[0022] The number of carbon atoms in component (B) is preferably 5 to 35, more preferably 7 to 33, even more preferably 10 to 30, and particularly preferably 13 to 28. When the number of carbon atoms in component (B) is within the above range, the resulting emulsion preparation tends to have excellent dispersibility.

[0023] Specific examples of component (B) include propylene glycol monocaprylate (carbon number = 11, IOB = 0.73), isopropyl myristate (carbon number = 17, IOB = 0.18), butyl stearate (carbon number = 22, IOB = 0.14), ethylhexyl palmitate (carbon number = 24, IOB = 0.13), cetyl ethylhexanoate (carbon number = 24, IOB = 0.13), diisopropyl adipate (carbon number = 12, IOB = 0.55), dibutyl sebacate (carbon number = 18, IOB = 0.33), and propylene glycol dicaprylate (carbon number = 19 , IOB=0.32), methyl acetylricinoleate (number of carbon atoms=21, IOB=0.29), propylene glycol dicaprate (number of carbon atoms=23, IOB=0.26), butyl acetylricinoleate (number of carbon atoms=24, IOB=0.25), diethylhexyl sebacate (number of carbon atoms=26, IOB=0.24), dibutyloctyl sebacate (number of carbon atoms=34, IOB=0.35), and glyceryl triethylhexanoate (number of carbon atoms=27, IOB=0.35), of which diisopropyl adipate and / or dibutyl sebacate are more preferred.

[0024] The emulsion preparation of the present invention contains component (B) in an amount of 0.0001 to 40% by mass, preferably 0.01 to 35% by mass, more preferably 1.0 to 30% by mass, even more preferably 5 to 25% by mass, and particularly preferably 10 to 20% by mass.

[0025] The emulsified preparation of the present invention contains a surfactant other than component (B) as component (C).

[0026] The surfactant other than (B), which is component (C) used in the emulsified preparation of the present invention, is preferably a nonionic surfactant and / or anionic surfactant, and more preferably a combination of a nonionic surfactant and an anionic surfactant.

[0027] Examples of nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyglycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene polyoxypropylene block copolymers, and preferred specific examples include one or more selected from the group consisting of polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, polyoxyethylene distyrenated phenyl ether, polyoxyethylene tristyrenated phenyl ether, and polyoxyethylene tribenzyl phenyl ether.

[0028] Examples of the anionic surfactant include higher fatty acid salts, alkylarylsulfonates, alkylnaphthalenesulfonates, alkyldiphenyletherdisulfonates, alkylsulfuric acid ester salts, polyoxyethylene alkyl ether sulfate salts, polyoxyethylene alkylaryl ether sulfate salts, alkyl sulfosuccinate salts and derivatives thereof, polyoxyethylene styrenated phenyl ether sulfosuccinate salts, polyoxyethylene styrenated phenyl ether sulfate salts, polyoxyethylene alkyl ether phosphate esters and salts thereof, and polyoxyethylene styrenated phenyl ether phosphate esters and salts thereof. Preferred specific examples include polyoxyethylene tristyrenated phenyl ether sulfate ester salts, polyoxyethylene tristyrenated phenyl ether sulfosuccinate ester salts and / or polyoxyethylene alkyl ether phosphate esters and salts thereof.

[0029] The emulsion preparation of the present invention contains 0.0001 to 15 mass %, preferably 0.01 to 13 mass %, more preferably 0.5 to 10 mass %, and even more preferably 1.5 to 7 mass % of a surfactant other than (B) as component (C).

[0030] In the emulsifying preparation of the present invention, the mass ratio (B) / (A) of component (B), i.e., the fatty acid ester having an IOB value of 0.12 to 1.0, to component (A), i.e., the 4-hydroxybenzoic acid ester represented by formula (1) or a salt thereof, is 0.40 to 70, preferably 0.50 to 20, more preferably 0.60 to 2.0, and even more preferably 0.67 to 1.2.

[0031] The mass ratio (C) / (A) of component (C), i.e., surfactant other than (B), to component (A), i.e., 4-hydroxybenzoic acid ester represented by formula (1) or its salt, is preferably 0.01 to 20, more preferably 0.05 to 2.0, and even more preferably 0.1 to 0.5.

[0032] The emulsion preparation of the present invention exhibits excellent dispersibility by containing each of the components (A) to (C) within the above ranges.

[0033] The emulsion preparation of the present invention is a so-called oil-in-water (O / W) emulsion composition and contains water. The type of water is not particularly limited, and any of distilled water, pure water, ultrapure water, ion-exchanged water, tap water, etc. can be used.

[0034] The emulsion preparation of the present invention preferably has a turbidity of 10 to 500 NTU. When the turbidity of the emulsion preparation is within the above range, the 4-hydroxybenzoic acid ester represented by formula (1) is uniformly dispersed, and various effects such as antibacterial properties can be uniformly exhibited.

[0035] The emulsified preparation of the present invention preferably has a turbidity reduction rate of 5% or less, more preferably 4% or less, and even more preferably 3% or less, after standing for 7 days at 25° C., expressed as [(turbidity before standing - turbidity after standing) / turbidity before standing] × 100 (%). When the turbidity reduction rate of the emulsified preparation is within the above range, it is possible to maintain a dispersed state for a long period of time.

[0036] As used herein, "turbidity" refers to a value measured using a formazin standard solution in accordance with JIS K 0101 (Testing Method for Industrial Water). Turbidity can be measured using a spectrophotometer such as NanoDrop2000 (manufactured by ThermoFisher Scientific).

[0037] To measure turbidity, first prepare dilutions (20 to 400 NTU) by diluting a formazin standard solution (400 NTU) to a predetermined concentration, and create a calibration curve based on the absorbance (wavelength 660 nm) of each dilution. Then, measure the absorbance (wavelength 660 nm) of the emulsion formulation, and calculate the turbidity from the calibration curve. Commercially available formazin standard solutions (400 NTU) can be used.

[0038] The emulsion preparation of the present invention may contain other components, such as organic solvents, stabilizers, antifoaming agents, parabens other than component (A), preservatives other than parabens, etc., as needed, provided that the effects of the present invention are not impaired.

[0039] The organic solvent is preferably a water-miscible organic solvent, and examples of the water-miscible organic solvent include alcohols such as methanol and ethanol; ethers such as tetrahydrofuran; ketones such as acetone; amides such as dimethylformamide and dimethylacetamide; and glycols such as butyl glycol and phenyl glycol.

[0040] Examples of stabilizers include xanthan gum, polyvinyl alcohol and modified products thereof, polyacrylic acid amide and derivatives thereof, ethylene-vinyl acetate copolymer, styrene-maleic anhydride copolymer, ethylene-maleic anhydride copolymer, isobutylene-maleic anhydride copolymer, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, vinyl acetate-acrylic acid copolymer, carboxymethyl cellulose, methyl cellulose, casein, gelatin, starch derivatives, gum arabic, and sodium alginate.

[0041] Examples of the antifoaming agent include silicone-based, higher fatty acid amide-based, polyethylene glycol-based, fatty acid lower alcohol ester-based, and polypropylene glycol-based antifoaming agents.

[0042] Examples of parabens other than component (A) include methylparaben, ethylparaben, propylparaben, butylparaben, and benzylparaben.

[0043] Examples of preservatives other than component (A) include sodium benzoate and salicylic acid derivatives.

[0044] The content of other ingredients in the emulsion preparation is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 20% by mass or less, even more preferably 10% by mass or less, even more preferably 5% by mass or less, and most preferably 1% by mass or less.

[0045] The present invention also provides a compound represented by the formula (1): [ka] [wherein R represents an alkyl group having 5 to 8 carbon atoms] 0.0001 to 50 mass% of a 4-hydroxybenzoic acid ester represented by the formula (I) or a salt thereof, Component (B) 0.0001 to 40 mass% of a fatty acid ester having an IOB value of 0.12 to 1.0; Component (C) 0.0001 to 15% by mass of a surfactant other than component (B), and water A method for producing an emulsified preparation comprising: mixing components including component (A), component (B), and component (C) and heating the mixture to obtain a melt; and A step of mixing the melt with water under stirring to emulsify and disperse component (A) in the water. Including, The mass ratio (B) / (A) of the component (B) to the component (A) in the emulsion preparation is 0.40 to 70.

[0046] First, the components (A) to (C) are mixed, and the resulting mixture is heated and melted to prepare a melt. The resulting melt is emulsified by mixing it with water under stirring, resulting in an emulsion formulation in which component (A) is emulsified and dispersed in water. The melt and water may be mixed by adding water while stirring the melt, or by adding the melt while stirring the water. For such emulsification under stirring, a magnetic stirrer, mechanical stirrer, homomixer, vacuum emulsifier, low-pressure homogenizer, high-pressure homogenizer, grinder, cutter mill, ball mill, jet mill, single-screw extruder, twin-screw extruder, ultrasonic agitator, or household juicer mixer can be used. The emulsification may be performed by combining two or more operations.

[0047] The temperature and time during emulsification of each component are not particularly limited, but are preferably within the temperature range of 5 to 50°C and the time range of 1 minute to 3 hours, for example.

[0048] The preferred range of the content of each component when mixed is the same as the preferred range of the content of each component in the emulsified preparation of the present invention described above.

[0049] The emulsified preparation of the present invention can be prepared into dosage forms such as sprays, aerosols, pump formulations, liquid formulations, liniments, matting agents, sheets, tapes, powders, granules, gels, creams, films, containers, and paints.

[0050] The emulsion preparation of the present invention can be applied to a region or body to be treated to impart the antibacterial, anti-algae, pest repellent, and other effects of paraben.

[0051] The emulsified preparation of the present invention can be applied to the area to be treated by methods such as scattering, spraying, and coating, and can be applied to the object to be treated by methods such as kneading, scattering, spraying, coating, and impregnation.

[0052] Specific examples of the treated area or object include clothing such as suits, dress shirts, T-shirts, polo shirts, blouses, slacks, skirts, and underwear; footwear such as socks, tabi socks, shoes, boots, sandals, clogs, slippers, and insoles; accessories such as hats, scarves, and gloves; bedding such as futons, sofas, blankets, and pillows; textile and leather shoe products such as towels, bath mats, entrance mats, and carpets; and building materials such as tatami mats, tiles, flooring, wall materials, and flooring.

[0053] By applying the emulsion preparation of the present invention to textile products in particular, textile products containing the emulsion preparation can be obtained.

[0054] The emulsified preparation of the present invention may be prepared at a high concentration and then diluted as appropriate for use. [Example]

[0055] The present invention will be described in detail below with reference to examples, but these examples are not intended to limit the scope of the present invention.

[0056] The storage stability, turbidity and antibacterial activity shown in the examples were measured by the methods described below. <Storage stability> Emulsified preparations (20 g) having the compositions shown in Table 1 were left to stand at 0°C and 25°C for one month, and then filtered through a sieve (20 mesh openings) to observe whether or not there was any precipitate. If there was no precipitate on the sieve, it was marked as ◯, and if there was precipitate, it was marked as ×. This evaluation was carried out to confirm whether or not there was any precipitation of large crystals of 20 mesh (0.84 μm) or larger, which could be visually determined.

[0057] <Turbidity> A formazin standard solution (turbidity 400 NTU, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was diluted 2, 4, 8, and 16 times with purified water to prepare standard solutions with turbidities of 200, 100, 50, and 25 NTU, respectively. The absorbance (measurement wavelength: 660 nm) of each turbidity standard solution was measured using the absorbance measurement device described below, and a calibration curve was created. 2.5 μL of the emulsion preparation prepared in the examples and 9997.5 μL of purified water were added to a sample tube and stirred for 30 seconds using a vortex mixer to prepare a 4000-fold diluted solution (0.00375% by mass of the 4-hydroxybenzoic acid ester represented by formula (1)). The absorbance (measurement wavelength: 660 nm) was measured, and the turbidity was determined by applying the calculated value to the calibration curve. The measured sample was allowed to stand at 25°C, and the absorbance was measured again after 1 and 7 days to determine the turbidity. Unlike the storage stability test described above, which checks for the presence or absence of large, visually detectable crystal precipitation, this evaluation was carried out with the aim of checking for the presence or absence of precipitation or sedimentation at the fine particle level. Absorbance measurement equipment: Spectrophotometer NanoDrop2000 (manufactured by ThermoFisher SCIENTIFIC)

[0058] <Antibacterial> The minimum inhibitory concentrations of various emulsion formulations against each bacterial species were measured according to the standard method (broth microdilution method) of the Japanese Society of Chemotherapy. 0.10 g of the emulsion formulation prepared in the Examples, 500 μL of dimethyl sulfoxide (DMSO), and 9.40 mL of sterile water were placed in a sample tube and stirred for 1 minute using a vortex mixer to prepare a pre-adjusted solution (emulsion formulation concentration 10,000 ppm). 180 μL of the pre-adjusted solution was added to each well in the first column from the left of a 96-well (12 columns x 8 rows) microplate, and 90 μL of sterile water was added to each well in the second to eleventh columns from the left. Next, 90 μL was taken from the well in the first column from the left and added to the adjacent well to the right, diluting it to half the concentration. This procedure was repeated for the second column and subsequent columns, preparing solutions containing emulsion formulations at concentrations of 10,000 to 10 ppm in the 96-well microplate. The remaining wells were filled with 90 μL of sterile water alone to serve as blanks.

[0059] Mueller-Hinton (MH) medium (Becton, Dickinson & Company) prepared at 67.5 g / L was sterilized and dispensed at 80 μL into each well. Next, each test fungus was cultured in MH medium at 30°C for 20 hours. The bacterial suspension was then diluted with saline to a concentration of 10 cfu / mL. 10 μL of this suspension was added to each of two horizontal rows of wells and then cultured at 30°C for 24 to 72 hours. After visually confirming the growth of each fungus in the blank, the growth of each fungus in each well was visually observed, and the minimum inhibitory concentration (MIC: μg / mL) was measured. The results are shown in Table 1.

[0060] The fungi used for the test are listed below. [Fungi to be tested] Fungus 1: Staphylococcus aureus (NBRC13276) Fungus 2: Candida albicans NBRC1594 Fungus 3: Aspergillus brasilliensis ATCC16404 Fungus 4: Trichophyton mentagrophytes NBRC32409

[0061] [Example 1] 15 g of n-hexyl 4-hydroxybenzoate, 15 g of dibutyl sebacate, 3 g of polyoxyethylene stearyl ether, and 2.1 g of polyoxyethylene tristyrenated phenyl ether sulfate ammonium salt were mixed in a 50 mL beaker and heated to 50 °C to obtain a homogeneous melt. Separately, 64.9 g of 50 °C water was placed in a 100 mL beaker and a homogenizer (TK Robomix, Primix Corporation) was installed. The melt was gradually added while stirring at 5000 rpm. Stirring was continued for 30 minutes to emulsify the n-hexyl 4-hydroxybenzoate and dibutyl sebacate, resulting in a finely dispersed emulsion. The antibacterial activity and turbidity of the resulting emulsion were measured. The results are shown in Table 1. The appearance of the emulsion is shown in Figure 1.

[0062] [Example 2] An emulsified preparation was obtained in the same manner as in Example 1, except that dibutyl sebacate was changed to diisopropyl adipate. The antibacterial activity and turbidity of the obtained emulsified preparation were measured. The results are shown in Table 1.

[0063] [Example 3] An emulsified preparation was obtained in the same manner as in Example 1, except that dibutyl sebacate was replaced with glyceryl triethylhexanoate. The antibacterial activity and turbidity of the obtained emulsified preparation were measured. The results are shown in Table 1.

[0064] [Example 4] An emulsified preparation was obtained in the same manner as in Example 1, except that dibutyl sebacate was replaced with butyl acetylricinoleate. The antibacterial activity and turbidity of the obtained emulsified preparation were measured. The results are shown in Table 1.

[0065] [Example 5] An emulsified preparation was obtained in the same manner as in Example 1, except that dibutyl sebacate was changed to dibutyl octyl sebacate. The antibacterial activity and turbidity of the obtained emulsified preparation were measured. The results are shown in Table 1.

[0066] [Example 6] An emulsified preparation was obtained in the same manner as in Example 1, except that dibutyl sebacate was replaced with ethylhexyl palmitate. The antibacterial activity and turbidity of the obtained emulsified preparation were measured. The results are shown in Table 1.

[0067] [Comparative Example 1] The same procedure as in Example 1 was carried out except that n-hexyl 4-hydroxybenzoate was replaced with butyl 4-hydroxybenzoate, but butyl 4-hydroxybenzoate precipitated, making it impossible to obtain an emulsified preparation. The appearance is shown in Figure 2.

[0068] Comparative Example 2 The same procedure as in Example 1 was carried out except that dibutyl sebacate was replaced with isocetyl myristate, but n-hexyl 4-hydroxybenzoate precipitated, and therefore an emulsified preparation could not be obtained.

[0069] Comparative Example 3 The same procedure as in Example 1 was carried out except that dibutyl sebacate was replaced with octyldodecyl myristate, but n-hexyl 4-hydroxybenzoate precipitated, and therefore an emulsified preparation could not be obtained.

[0070] Comparative Example 4 The same procedure as in Example 1 was carried out except that dibutyl sebacate was not added, but n-hexyl 4-hydroxybenzoate precipitated, and therefore an emulsion could not be obtained.

[0071] Comparative Example 5 The same procedure as in Example 1 was conducted except that polyoxyethylene stearyl ether and polyoxyethylene tristyrenated phenyl ether sulfate ammonium salt were not added, but n-hexyl 4-hydroxybenzoate precipitated, and therefore an emulsion could not be obtained.

[0072] [Table 1]

[0073] (A-1): n-Hexyl 4-hydroxybenzoate (A-2): n-butyl 4-hydroxybenzoate (B-1): Dibutyl sebacate (IOB value = 0.33) (B-2): Diisopropyl adipate (IOB value = 0.55) (B-3): Glyceryl triethylhexanoate (IOB value = 0.35) (B-4): Butyl acetylricinoleate (IOB value = 0.25) (B-5): Dibutyloctyl sebacate (IOB value = 0.18) (B-6): Ethylhexyl palmitate (IOB value = 0.13) (B-7): Isocetyl myristate (IOB value = 0.10) (B-8): Octyldodecyl myristate (IOB value = 0.09) (C-1): Polyoxyethylene stearyl ether (C-2): Polyoxyethylene tristyrenated phenyl ether sulfate ester ammonium salt

[0074] The emulsion preparations of the present invention (Examples 1 to 6) have good storage stability because no precipitation or sedimentation can be visually confirmed when they contain specific fatty acid esters. Furthermore, the rate of decrease in turbidity over time is low, confirming the absence of precipitation or sedimentation at the microparticle level, demonstrating excellent dispersibility in water. It is also understood that the preparations exhibit antibacterial effects against fungi.

Claims

1. Component (A) Formula (1) 【Chemistry 1】 [wherein R represents an alkyl group having 5 to 8 carbon atoms] 0.0001 to 50 mass% of a 4-hydroxybenzoic acid ester represented by the formula (I) or a salt thereof, Component (B) 0.0001 to 40% by mass of a fatty acid ester having an IOB value of 0.12 to 1.0, Component (C) 0.0001 to 15 mass% of a surfactant other than component (B), and water, An emulsifying preparation, wherein the mass ratio (B) / (A) of component (B) to component (A) is 0.40 to 70.

2. 2. The emulsion preparation according to claim 1, wherein component (A) is n-hexyl 4-hydroxybenzoate.

3. 2. The emulsion preparation according to claim 1, wherein component (B) is one or more selected from the group consisting of propylene glycol monocaprylate, isopropyl myristate, butyl stearate, ethylhexyl palmitate, cetyl ethylhexanoate, diisopropyl adipate, dibutyl sebacate, propylene glycol dicaprylate, methyl acetylricinoleate, propylene glycol dicaprate, butyl acetylricinoleate, diethylhexyl sebacate, dibutyloctyl sebacate, and glyceryl triethylhexanoate.

4. 2. The emulsion preparation according to claim 1, wherein component (C) is a nonionic surfactant and / or anionic surfactant.

5. 5. The emulsion preparation according to claim 4, wherein the nonionic surfactant is one or more selected from the group consisting of polyoxyethylene stearyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, polyoxyethylene distyrenated phenyl ether, polyoxyethylene tristyrenated phenyl ether, and polyoxyethylene tribenzyl phenyl ether.

6. 5. The emulsion preparation according to claim 4, wherein the anionic surfactant is polyoxyethylene tristyrenated phenyl ether sulfate, polyoxyethylene tristyrenated phenyl ether sulfosuccinate, and / or polyoxyethylene alkyl ether phosphate and its salt.

7. 2. The emulsion preparation according to claim 1, which exhibits a turbidity reduction rate of 5% or less after standing at 25°C for 7 days.

8. Component (A) Formula (1) 【Chemistry 2】 [wherein R represents an alkyl group having 5 to 8 carbon atoms] 0.0001 to 50 mass% of a 4-hydroxybenzoic acid ester represented by the formula (I) or a salt thereof, Component (B) 0.0001 to 40% by mass of a fatty acid ester having an IOB value of 0.12 to 1.0, Component (C) 0.0001 to 15% by mass of a surfactant other than component (B), and water A method for producing an emulsified preparation comprising: mixing components including component (A), component (B), and component (C) and heating the mixture to obtain a melt; and A step of mixing the melt with water under stirring to emulsify and disperse component (A) in the water. Including, The method, wherein the mass ratio (B) / (A) of the component (B) to the component (A) in the emulsified preparation is 0.40 to 70.

9. A method for applying the emulsion preparation according to any one of claims 1 to 7 to a region or body to be treated, wherein the application is carried out by kneading, scattering, spraying, coating or impregnation.

10. A textile product containing the emulsion preparation according to any one of claims 1 to 7.

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