WO2023120346A1 - 抗菌抗カビ組成物 - Google Patents

抗菌抗カビ組成物 Download PDF

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WO2023120346A1
WO2023120346A1 PCT/JP2022/046145 JP2022046145W WO2023120346A1 WO 2023120346 A1 WO2023120346 A1 WO 2023120346A1 JP 2022046145 W JP2022046145 W JP 2022046145W WO 2023120346 A1 WO2023120346 A1 WO 2023120346A1
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test
antibacterial
amount
oil
component
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French (fr)
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誠治 立花
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Earth Corp
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Earth Corp
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Disinfection or sterilisation of materials or objects, in general; Accessories therefor
    • A61L2/16—Disinfection or sterilisation of materials or objects, in general; Accessories therefor using chemical substances
    • A61L2/22—Phase substances, e.g. smokes or aerosols

Definitions

  • the present invention relates to an antibacterial antifungal composition and a spray thereof.
  • the purpose of the present invention is to provide an antibacterial and antifungal composition and a spray thereof that can exhibit antimicrobial activity for a long period of time in a wet environment such as a bathroom.
  • the gist of the present invention is as follows. 1. An antibacterial and antifungal composition comprising (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component. 2.1. A spray containing the antibacterial and antifungal composition described in 1. above in a spray container.
  • Component (A) in the present invention is an oil-soluble antibacterial component.
  • the oil-soluble antibacterial component in the present invention means a component exhibiting antibacterial, antifungal, and antiviral activity with a water solubility of less than 1 w/w% at 25°C.
  • Component (A) in the present invention is preferably an antibacterial component with a water solubility of less than 0.1 w/w% at 25°C, more preferably less than 0.06 w/w%.
  • the water solubility in the present invention is calculated by EPI suite version 4.11, which is one of the physical property estimation software for chemical substances available from the United States Environmental Protection Agency (EPA). /w%).
  • Component (A) in the present invention is not particularly limited as long as it is the oil-soluble antibacterial component described above. compounds known to have antibacterial activity of In addition, antibacterial fragrance ingredients, environmental hygiene antibacterial ingredients such as 3-iodo-2-propynylbutylcarbamate (IPBC), capric acid monoglyceride, [(4-chlorophenoxy)methyl]3-iodo-2-propynyl ether, procymidone , bioreton, morestan and other agricultural chemical bactericidal components. Among them, phenol compounds and antibacterial fragrance ingredients are preferred as the component (A) in the present invention, since they can stably exert antibacterial and antifungal effects even in a wet environment. In addition, the component (A) in the present invention does not contain components with positive electrical properties such as cationic compounds.
  • Phenolic compounds suitable as the component (A) in the present invention are those having oil-soluble (water-insoluble) antibacterial activity and having a basic skeleton of a chemical structure in which one of the hydrogen atoms of benzene is substituted with a hydroxyl group. .
  • phenol compounds examples include alkyl-substituted phenols such as cresol, ethylphenol, propylphenol, butylphenol, pentylphenol, hexylphenol, cyclohexylphenol, xylenol, methylethylphenol, isopropylmethylphenol, and di-t-butylphenol;
  • alkyl ether derivatives of dihydric phenol such as eugenol, hydroxybenzoic acid such as methylparaben, ethylparaben, propylparaben, butylparaben, salicylic acid, and hydroxybenzoic acid alkyl ester derivatives such as methyl salicylate.
  • phenol compounds having no heteroatoms other than oxygen atoms are preferred, alkyl-substituted phenols are more preferred, and alkyl-substituted phenols substituted with one or two alkyl groups having 1 to 6 carbon atoms are more preferred, particularly , a dialkyl-substituted phenol substituted with two alkyl groups having 1 to 6 carbon atoms.
  • alkyl-substituted phenol isopropylmethylphenol is preferable.
  • 4-isopropyl-3- is preferred because high antibacterial, antifungal, and antiviral effects can be obtained by using it in combination with the cationic antibacterial component of component (B), which will be described later.
  • the water solubility at 25°C is 0.002 w/w% linalyl acetate, 0.0039 w/w% citronellal, 0.026 w/w% geraniol, 0.068 w/w% linalool, and 0.043 w/w menthol, respectively.
  • X ⁇ is a counterion.
  • R 5 is an alkyl group having 8 to 18 carbon atoms
  • X - is a counterion.
  • each R 6 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms
  • each R 7 is independently a an alkylene group
  • R 8 is an alkylene group having 2 to 8 carbon atoms
  • each R 9 is independently an alkyl group having 1 to 18 carbon atoms
  • X 2- is a counterion.
  • any of the groups which may be the same or different from R 1 and have an alkyl group having 1 to 4 carbon atoms or 8 to 18 carbon atoms, a benzyl group, or an alkyl chain having 8 to 10 carbon atoms
  • An alkylphenyldiethoxy group is preferable, and an alkyl group having 8 to 18 carbon atoms, a benzyl group, and an alkylphenyldiethoxy group having an alkyl chain having 8 carbon atoms are more preferable.
  • R 3 and R 4 are alkyl groups having 1 to 4 carbon atoms, which may be the same or different, and are preferably methyl groups.
  • Specific examples of the compound represented by the general formula (3) include 1,4-bis(3,3′-(1-decylpyridinium)methyloxy)butane bromide, 1,4-bis(3,3 '-(1-decylpyridinium)methyloxy)butane chloride, 1,4-bis(3,3'-(1-decylpyridinium)methyloxy)butane dimethosulfate and the like.
  • the spray member (spray button) in the present invention is a member that is attached to the pressure container via an aerosol valve for fixed quantity spray.
  • the spray button is formed with a passage in the operating part through which the aerosol composition taken from the pressure container passes through the stem hole of the aerosol valve for fixed quantity spray, and a nozzle hole through which the aerosol composition is sprayed.
  • the inner diameter of the nozzle of the spray button is preferably ⁇ 0.45 to 3.0 mm, more preferably ⁇ 0.5 to 2.0 mm, from the viewpoint of keeping the spray time within the desired range. , ⁇ 0.6 to 1.6 mm are more preferable.
  • a digital force gauge for example, manufactured by Imada Co., Ltd., model number: DS2-2N placed at a distance of 20 cm from the nozzle of the metered aerosol. It can be measured by calculating the average of the maximum value when the aerosol composition is sprayed toward the center of a circular flat plate with a diameter of ⁇ 60 mm attached to the device.
  • the metered dose aerosol in the present invention has a spraying time of 1 second or less in one spraying operation.
  • spraying an aerosol composition with a predetermined amount in the range of 0.1 to 3.0 mL per spray within 1 second (A) oil-soluble contained in the antibacterial antifungal composition of the present invention Since the diffusibility of the antibacterial component and (B) the cationic antibacterial component can be efficiently increased, (A) the oil-soluble antibacterial component and (B) the cationic antibacterial component adhere to the object existing in the moist environment. It is believed that not only the amount but also the fixing amount can be improved.
  • the particle size of the antibacterial and antifungal composition when sprayed from the nozzle is not particularly limited, but if the average particle size at a spray distance of 50 cm from the nozzle is in the range of 5 ⁇ m or more and less than 100 ⁇ m, This is preferable in terms of improving not only the amount of adhesion to an object in a wet environment but also the amount of fixation.
  • the particle size means a numerical value measured by a particle size distribution measuring container. Specifically, from a position where the distance between the laser beam emitted from the laser light emitting part of the particle size distribution measurement container to the light receiving part and the injection port of the test sample is 50 cm, the sprayed matter passes through the laser beam perpendicularly.
  • the antibacterial and antifungal composition containing (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component contains deodorant components (flavonoids, etc.) and the like, as long as the effects of the present invention are not impaired.
  • a perfume component other than the antibacterial perfume component, etc. may be blended.
  • commonly used formulation aids such as liquid carriers, surfactants, solid carriers, antifreezing agents, antifoaming agents, antiseptics, etc. agents, antioxidants, perfume ingredients, antistatic agents, film-forming agents, thickeners and the like may be added.
  • Example 2 As shown in Table 2, the test specimens of Examples 1 and 2, which are specific examples of the antibacterial and antifungal composition of the present invention using (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component, were used in bathrooms in Japan.
  • the adhesion amount of (A) the oil-soluble antibacterial component to the test member of the mortar plate imitating the wall material is about 1.5 compared to the test specimen of Comparative Example 1 containing only the (A) oil-soluble antibacterial component It has been clarified that the efficiency is improved by about 1.9 times.
  • the obtained acetone cleaning solution was quantitatively analyzed by gas chromatography / high performance liquid chromatography, and (A) oil-soluble adhering to the test member
  • 4-isopropyl-3-methylphenol was analyzed by gas chromatography, and benzalkonium chloride was analyzed by high performance liquid chromatography. The test was performed in duplicate.
  • the amount of fixation of the test specimen of Example 1 which is a specific example of the antibacterial and antifungal composition of the present invention, which uses (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component in combination, is
  • the (B) cationic antibacterial component (BZC) on the test member of the mortar board imitating the wall material of a bathroom in Japan is 76% with respect to the adhesion amount of the (B) cationic antibacterial component (BZC) shown in Table 3.
  • the amount of fixation of the test specimen of Comparative Example 2 was about 40% of the amount of adhesion shown in Table 3.
  • Example 1 which is a specific example of the antibacterial and antifungal composition of the present invention that uses (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component, was used for the wall of a bathroom in Japan.
  • the amount of (A) oil-soluble antibacterial component adhered to the FRP and mortar test members imitating wood is about 1.8 times that of the test specimen of Comparative Example 1 containing only (A) the oil-soluble antibacterial component.
  • a pressure can for aerosol (capacity 133 mL) is filled with 6 mL of each test sample stock solution of Example 3, Comparative Examples 3 and 4, and an aerosol valve (one spray amount 1 mL, stem hole (shape: rectangular, area 0.7 mm 2 (1.0 mm x 0.7 mm) x 2)) to close the aerosol pressure can.
  • an aerosol valve one spray amount 1 mL, stem hole (shape: rectangular, area 0.7 mm 2 (1.0 mm x 0.7 mm) x 2
  • 14 mL of liquefied petroleum gas (0.49 MPa (25° C.) was filled under pressure as a propellant.
  • Test specimen preparation of test specimen stock solution
  • the test specimens of Example 1 and Comparative Example 1 of the above-mentioned "adhesion amount improvement effect confirmation test-1" were used as the test specimen undiluted solutions.
  • a pressure can for aerosol (capacity 133 mL) is filled with 6 mL of each test sample stock solution of Example 1 and Comparative Example 1, and an aerosol valve (one spray amount 1 mL, stem hole (shape: rectangular, area 0.7 mm 2 (1 0 mm x 0.7 mm) x 2)) to close the aerosol pressure can.
  • Test method The same mortar plate (5 cm x 5 cm, about 20 g) imitating the wall material of a bathroom in Japan, which was prepared in the above "Deposited amount improvement effect confirmation test-1", was used as a test member. Ten test members (a total of 20 pieces) were affixed to each of two locations on a ceiling and a side wall measuring .8m x 1.8m x height 2m. The humidity in the bathroom (25 ° C.) was adjusted to 90% or more, and 20 test members at two locations were sufficiently wetted with water. The test specimen is sprayed (once sprayed) from the entrance of each bathroom toward the center of the bathroom, and 30 minutes after the spray treatment, two test members on the ceiling and two test members on the side walls are collected.
  • Test specimens The following test specimens were prepared by adding 0.001 to 20 parts by weight of the oil-soluble antibacterial component (A) to 1 part by weight of the cationic antibacterial component (B).
  • the oil-soluble antibacterial component (A) shown in Table 11 below was diluted with ethanol to 13 w/v%, and diluted to 52 v/v% and purified water to 48 v/v%. This diluted solution was centrifuged (3500 rpm, 12 minutes), and the water layer part was added with (B) cationic antimicrobial component benzalkonium chloride or 1,4-bis(3,3'-(B) shown in Table 11 below.
  • Dibutyl phthalate was added as an internal standard to the obtained acetone cleaning solution, and quantitative analysis was performed by gas chromatography to analyze the amount (mg) of the (A) oil-soluble antibacterial component adhering to the test member.
  • the composition of each example test specimen a to f or comparative example test specimen a and the adhesion amount of (A) oil-soluble antibacterial component adhered to the test member are shown in Table 11 below as "adhesion amount (mg / test piece)". Shown together.
  • the example test specimen a which is a specific example of the antibacterial and antifungal composition of the present invention that uses (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component in combination, is a bathroom wall material in Japan.
  • the amount of (A) the oil-soluble antibacterial component attached to the test member of the mortar plate imitating the (A) compared to the comparative example test specimen a containing only the oil-soluble antibacterial component is improved by about 1.5 times. It became clear.
  • (A) the oil-soluble antibacterial component and (B) the cationic antibacterial component were used in combination to suppress (A) the oil-soluble antibacterial component against objects present in a moist environment. It was confirmed that the effect of greatly improving the amount of the component attached was obtained.
  • test member was immersed in each (10 mL) of the test samples a to f of the examples and the test sample a of the comparative example, and mixed by inversion 10 times.
  • a test member taken out from each test specimen was immersed for 1 second in purified water (50 mL) stirred at 200 rpm, and thoroughly washed with about 5 mL of acetone.
  • Dibutyl phthalate was added as an internal standard to the obtained acetone cleaning solution, and quantitative analysis was performed by gas chromatography to analyze the amount (mg) of the (A) oil-soluble antibacterial component adhered to the test member.
  • Example test specimens a to f the amount of (A) fixed amount of oil-soluble antibacterial component is "fixed amount (mg/test piece)", and the percentage of the value obtained by dividing this fixed amount by the adhesion amount shown in Table 11 above ( %) is collectively shown in Table 12 below as “fixed amount/deposited amount (%)”.
  • Example test specimens c, d, e, and f used in the “adhesion amount/fixation amount improvement effect confirmation test-3” were used.
  • test specimens in which borneol in example test specimen d was replaced with linalool and 1,8-cineol were used in example test specimens g and j, and IPMP in example test specimen b was replaced with geraniol and camphor.
  • Example test sample k was obtained by replacing “BZC” of example test sample c with cetylpyridinium chloride in example test samples h and i.
  • test samples obtained by replacing “IPMP” of Comparative Example Test Specimen a with borneol, citronellal, linalool, geraniol, camphor, and 1,8-cineole were prepared as Comparative Example Test Specimens b, c, d, e, f, g.
  • Adhesion amount improvement effect confirmation test The same mortar plate (5 cm ⁇ 5 cm, about 20 g) imitating the wall material of a bathroom in Japan, which was prepared in the above "Adhesion amount improvement effect confirmation test-1", was used as a test member.
  • test member is immersed in each (150 mL) of example test samples c to k or comparative example test samples b to g (150 mL) and each test solution is stirred for 10 minutes, and about 10 mL of acetone for washing is used.
  • Adhesion amount improvement effect confirmation test of the above "Adhesion amount/fixing amount improvement effect confirmation test-3".
  • Fixing amount improvement effect confirmation test The same mortar plate (5 cm ⁇ 5 cm, about 20 g) imitating the wall material of a bathroom in Japan, which was prepared in the above “Adhesion amount improvement effect confirmation test-1”, was used as a test member.
  • test member was immersed in each (150 mL) of test samples c to k of Examples or test samples b to g of Comparative Examples, and each test solution was stirred for 10 minutes.
  • a test member taken out from each test solution was immersed for 1 second in purified water (300 mL) stirred at 200 times/min, and then thoroughly washed with about 10 mL of acetone.
  • the subsequent quantitative analysis was performed in the same manner as in "(3) Fixing amount improvement effect confirmation test" of the above "Adhesion amount/fixing amount improvement effect confirmation test-3".
  • composition of each example test specimen c to k or comparative example test specimen b to g, and the adhesion amount of (A) oil-soluble antibacterial component adhered to the test member is "adhesion amount (mg / test piece)", and the fixing amount is "Fixed amount (mg/test piece)” and the percentage (%) of the value obtained by dividing this fixed amount by the adhered amount is shown in Table 13 below as “Fixed amount/adhered amount (%)".
  • benzalkonium chloride is indicated as "BZC”
  • 1,4-bis(3,3'-(1-decylpyridinium)methyloxy)butane bromide is indicated as "hygenia”
  • cetylpyridinium chloride is indicated as "CPC”.
  • example test specimens c to j which are specific examples of the antibacterial and antifungal composition of the present invention that uses (A) an oil-soluble antibacterial component and (B) a cationic antibacterial component in combination, were used in bathrooms in Japan.
  • the adhesion amount of (A) the oil-soluble antibacterial component to the test member of the mortar plate imitating the wall material is about 1.1 compared to the comparative test specimens b to g containing only the (A) oil-soluble antibacterial component. It was clarified that it improved by ⁇ 1.3 times.
  • example test specimens c to k which are specific examples of the antibacterial and antifungal composition of the present invention, are the amount of (A) the oil-soluble antibacterial component fixed to the test member of a mortar plate imitating the wall material of a Japanese bathroom. was 58 to 87% of the adhesion amount.
  • the values of (A) the amount of fixation/adhesion (%) of the oil-soluble antibacterial component in Examples c to k correspond to the amounts of fixation/adhesion (%) of the (A) oil-soluble antibacterial component in Comparative Examples b to g. It was found to be 1.1 to 1.5 times as high as the amount (%) and to be excellent in fixability. That is, it was confirmed that even when an antibacterial fragrance component was employed as (A) the oil-soluble antibacterial component in the present invention, excellent fixability to objects existing in a wet environment could be achieved. In addition, it was also confirmed that compared to the comparative test specimens b to g containing only the antibacterial fragrance component as the (A) oil-soluble antibacterial component, the fixability to objects in a wet environment is excellent.
  • Test Specimen The test specimens of Example 1 and Comparative Example 1 used in the above-mentioned "adhesion amount improvement effect confirmation test-1" were used.
  • test members an acrylic resin plate (manufactured by Hikari Co., Ltd., Sumiholiday A000-2SS) and an ABS resin plate (manufactured by Nippon Test Panel Co., Ltd.), each measuring 5 cm ⁇ 5 cm, were used.
  • Test method 10 ⁇ L of each of the test specimens of Example 1 and Comparative Example 1 was dropped onto each test member and left for 5 minutes.
  • Example 1 did not have a large effect on the test member even though it contained (A) 4-isopropyl-3-methylphenol, which is an oil-soluble antibacterial component, as in Comparative Example 1.
  • (B) combined use with benzalkonium chloride, which is a cationic antibacterial component, 4-isopropyl-3-methylphenol was suppressed from penetrating into the interior of the test member and remained on the surface of the test member.
  • the (A) oil-soluble antibacterial component in the present invention may cause external effects such as whitening and swelling on plastic materials such as acrylic resins and ABS resins used for bathroom accessories and drains.

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0616511A (ja) * 1991-01-31 1994-01-25 Kiyasupa Kk 抗菌剤及びその製造方法
JPH11286405A (ja) * 1998-03-31 1999-10-19 Dainippon Jochugiku Co Ltd 防カビ剤
JP2000355512A (ja) * 1999-06-14 2000-12-26 S T Chem Co Ltd 環境抗菌剤および抗菌性物質の製造法
JP2006151908A (ja) * 2004-11-30 2006-06-15 Lion Corp ヌメリ抑制用組成物およびヌメリ抑制方法
JP2007306978A (ja) * 2006-05-16 2007-11-29 Aasu Biochem Kk 防臭消臭剤
JP2017002007A (ja) * 2015-06-15 2017-01-05 大日本除蟲菊株式会社 水系防カビ剤
JP2017039646A (ja) * 2015-08-17 2017-02-23 大日本除蟲菊株式会社 殺菌効力増強剤およびそれを含有する液状殺菌組成物
JP2019151735A (ja) * 2018-03-02 2019-09-12 花王株式会社 硬質表面用殺黴洗浄剤組成物
JP2021166821A (ja) * 2020-03-13 2021-10-21 大日本除蟲菊株式会社 特定有害物防除用定量噴射エアゾール製品、及びこれを用いた特定有害物防除方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0616511A (ja) * 1991-01-31 1994-01-25 Kiyasupa Kk 抗菌剤及びその製造方法
JPH11286405A (ja) * 1998-03-31 1999-10-19 Dainippon Jochugiku Co Ltd 防カビ剤
JP2000355512A (ja) * 1999-06-14 2000-12-26 S T Chem Co Ltd 環境抗菌剤および抗菌性物質の製造法
JP2006151908A (ja) * 2004-11-30 2006-06-15 Lion Corp ヌメリ抑制用組成物およびヌメリ抑制方法
JP2007306978A (ja) * 2006-05-16 2007-11-29 Aasu Biochem Kk 防臭消臭剤
JP2017002007A (ja) * 2015-06-15 2017-01-05 大日本除蟲菊株式会社 水系防カビ剤
JP2017039646A (ja) * 2015-08-17 2017-02-23 大日本除蟲菊株式会社 殺菌効力増強剤およびそれを含有する液状殺菌組成物
JP2019151735A (ja) * 2018-03-02 2019-09-12 花王株式会社 硬質表面用殺黴洗浄剤組成物
JP2021166821A (ja) * 2020-03-13 2021-10-21 大日本除蟲菊株式会社 特定有害物防除用定量噴射エアゾール製品、及びこれを用いた特定有害物防除方法

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