CN103002732A - Antibacterial agent - Google Patents
Antibacterial agent Download PDFInfo
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- CN103002732A CN103002732A CN2011800346150A CN201180034615A CN103002732A CN 103002732 A CN103002732 A CN 103002732A CN 2011800346150 A CN2011800346150 A CN 2011800346150A CN 201180034615 A CN201180034615 A CN 201180034615A CN 103002732 A CN103002732 A CN 103002732A
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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
- 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
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2027—Monohydric alcohols unsaturated
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2034—Monohydric alcohols aromatic
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2068—Ethers
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
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Abstract
Provided is an antibacterial agent which is useful for the removal of pink mold produced in the living environments. The antibacterial agent is obtained by combining a quaternary ammonium salt that is described as the component (A) below and an organic solvent that is described as the component (B) below. (A) One or more quaternary ammonium salts selected from among dialkyl dimethyl ammonium salts and alkyl benzyl dimethyl ammonium salts. (B) One or more organic solvents selected from among aromatic alcohols, aromatic aldehydes and the compounds represented by formulae (1) and (2) (wherein R represents an alkyl group or alkenyl group having 5-10 carbon atoms or a benzyl group; A represents an alkylene group having 1-10 carbon atoms; and n represents a number of 0-5 and the n-numbered A groups may be the same or different).
Description
Technical field
The present invention relates to the adhering to of pink dirt that produces in the living environment prevented and remove useful antibacterial agent.
Background technology
In the last few years, people had improved the requirement of the cleaning of the living environments such as further maintenance family or job site, communal facility.But on the other hand, because office block or apartment seal height in the last few years the building, particularly city accumulate moisture easily, thereby be in the easily environment of breeding of the microorganisms such as bacterium or mould.Particularly in the toilet, the water place such as bathroom, washroom, kitchen, because of easier breedings of condition microorganism such as moisture or moisture or temperature.
In the living environments such as water place, significant a kind of dirty be to present red or the attachment of the color that pink isogonic is red or the pink dirt that mucus is representative.The pink dirt is remarkable especially in the positions such as bottom of the containers such as floor, washing bucket or Shampoo bottle in discharge outlet, liner, drinking valve place, bathroom.The pink dirt can be regenerated again after cleaning immediately, thereby is the dirt that bothers very much for cleaning person.In addition, pink dirt not only is difficult to remove, and brings discomfort because of mucus sense and the difference that looks to the user at water place.Therefore wish to develop the Clean method that effectively to remove pink dirt, keep the water place.
As the mushroom of from pink dirt, separating, the report have rhodotorula (
Rhodotorula) belong to yeast, methyl bacillus (
Methylobacterium) belong to bacterium, Brevundimonas sp (
Brevundimonas) belong to bacterium, microbacterium (
Microbacterium) belong to bacterium etc. (patent documentation 1, non-patent literature 1).Wherein rhodotorula (
Rodotorula) to belong to yeast fast with other bacterial classification phase specific growth rate, so as the main pathogenic fungi of pink dirt and known (patent documentation 1).Therefore, as for rhodotorula (
Rhodotorula) belong to yeast antibacterial activity high, to the effective composition of the inhibition of mucus, reported silver-colored class, zinc class, titanium class, copper class the mineral-type antibacterial agents such as antibiotic property metal, alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium salt, zephiran (
Benzalkonium) salt, imidazoline salt etc. (patent documentations 1) such as surfactant-based antibacterial agents.
Yet, about pink dirt, be not conceived to so far the methyl bacillus (
Methylobacterium) belong to bacterium, inquire into the report of removing pink dirt from the viewpoint of the growth and breeding that suppresses this bacterium.
The prior art document
Patent documentation
Patent documentation 1: Japanese patent application laid is willing to the 2006-151908 communique
Non-patent literature
Non-patent literature 1: the science of cleaning,, 16 ~ 22 pages of No. 4,52 volumes in 2007
Summary of the invention
The present invention relates to following invention.
1) quaternary ammonium salt that following composition (A) is represented and (B) antibacterial agent that combines of represented organic solvent.
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt.
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2).
[in the formula, R represents that carbon number is 5 ~ 10 alkyl or thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.]
2) contain above-mentioned 1) the bactericidal composition of antibacterial agent.
3) a kind of pink dirt adhere to the method that prevents or remove, it is characterized in that above-mentioned antibacterial agent or bactericidal composition are applied to the place of easy generation microbial contamination.
4) the represented quaternary ammonium salt of following composition (A) and (B) combination of represented organic solvent as the use of antibacterial agent.
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt.
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2).
[in the formula, R represents that carbon number is 5 ~ 10 alkyl or thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.]
5) the represented quaternary ammonium salt of following composition (A) and (B) combination of represented organic solvent for the manufacture of the use in the antibacterial agent.
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt.
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2).
[in the formula, R represents that carbon number is 5 ~ 10 alkyl or thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.]
6) a kind of antibiotic method is characterized in that being used in combination the represented quaternary ammonium salt of following composition (A) and (B) represented organic solvent.
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt.
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2).
[in the formula, R represents that carbon number is 5 ~ 10 alkyl or thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.]
Description of drawings
Fig. 1 is the SEM picture of pink dirt.
Fig. 2 is the confocal laser microscopic iage (confocal laser microscope) that uses the FISH of pink dirt.
Embodiment
The present invention relates to provide for preventing and remove in living environment near the antibacterial agent that is attached with usefulness of the pink dirt that particularly produces on the hard surface toilet, bathroom, kitchen etc.
The present inventors use sweep electron microscope (SEM) or confocal laser microscope (CLSM) to analyze actual pink dirt, its found that the main pathogenic fungi that produces pink dirt be previously known rhodotorula (
Rhodotorula) belong to yeast, not equal to be the methyl bacillus (
Methylobacterium) the genus bacterium.So, for can establishment or stop the methyl bacillus (
Methylobacterium) composition that belongs to the growth and breeding of bacterium inquires into, find in the situation that is used in combination specific quaternary ammonium salt and organic solvent, can to the methyl bacillus (
Methylobacterium) belong to the excellent antibacterial activity of bacterium performance, useful for removing of pink dirt.
By antibacterial agent of the present invention, in the time of on the hard surfaces such as the wall that is used for living environment, particularly kitchen or bathroom, toilet, washstand etc. or floor, apparatus machine, can carry out sterilization and antifouling to this hard surface, specifically can prevent adhering to and removing easily accompanying pink dirt of pink dirt.
In the present invention, dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt as the quaternary ammonium salt of composition (A) is as the known compound of antibiotic property cationic surfactant.
In the present invention, as dialkyl dimethyl ammonium salt and alkyl dimethyl ammonium salt, can preferably enumerate respectively dialkyl group (C
8-18) dimethyl ammonium, alkyl (C
8-18) dimethyl ammonium.
At this, can enumerate carbon number as alkyl is 8 ~ 18 straight chained alkyl, for example be octyl group, decyl, dodecyl (lauryl), myristyl (myristyl), cetyl (cetyl), heptadecyl, octadecyl (stearyl), be preferably octyl group, decyl, dodecyl.
As preferred dialkyl dimethyl ammonium salt, can enumerate didecyldimethyl ammonium salt, as the alkyl benzyl dimethyl ammonium salt, can enumerate octyl group benzyl dimethyl ammonium salt, dodecylbenzyl dimethyl ammonium etc.
Ammonium salt can be enumerated and F
-, Cl
-, Br
-, I
-Deng halide ion, NO
-And SO
4 2-Deng salt, be preferably the salt with halide ion, further the salt of preferred and chloride ion.
As more preferred quaternary ammonium salt, can enumerate octyl group benzyl dimethyl ammonium chloride, dodecylbenzyl alkyl dimethyl ammonium chloride, DDAC etc.
The quaternary ammonium salt of the composition of the invention described above (A) can use known method manufacturing, also can use commercially available product.Make such as can buy QUARTAMIND10(Kao Corp as dialkyl dimethyl ammonium salt), as the alkyl benzyl dimethyl ammonium salt can buy SANISOL08, SANISOLC(Kao Corp makes) etc. use.
Quaternary ammonium salt of the present invention in general known its shows excellent antimicrbial power to bacterium etc. separately.But, as described later shown in the embodiment, to Escherichia coli (
E.coli), staphylococcus aureus (
S.aureus), pseudomonas aeruginosa (
P.aeruginosa)Show under the concentration of enough antimicrbial powers, to the methyl bacillus (
Methylobacterium) belong to bacterium and do not show antibacterial activity, and must just can observe significant bacterial population and reduce to use the time of contact more than 30 minutes with the concentration more than 10 times.That is, distinguish the methyl bacillus (
Methylobacterium) to belong to bacterium very high for the patience of this quaternary ammonium salt.
And find, in these cases, be used in combination by the organic solvent with this quaternary ammonium salt and composition (B) and can improve extraordinarily its antimicrbial power.Therefore, with the quaternary ammonium salt of mentioned component (A) more than a kind and the antibacterial agent that combines more than a kind of the organic solvent of composition (B) can be used as suppress to comprise the methyl bacillus (
Methylobacterium) belong to bacterium in the breeding growth (antibacterial) of interior microorganism or stop the antibacterial agent of its breeding growth (sterilization) or the antibacterial agent that adheres to for the pink dirt that prevents or remove living environment.
At this, " living environment " comprises family, the workplace, school, whole environment that the people of the work of communal facility etc. or animal can survive, be preferably, the environment that the environment that particularly moisture is many and pink dirt produce easily, for example, the bathroom, the washroom, the washing chamber, the water place such as toilet or kitchen, the drinking water place, swimming pool, clean facility, and other water pipe facility periphery, more specifically, can enumerate kitchen or bathroom, the toilet, the wall of washstand etc. or ground, the bottom of washing bucket, the bottle bottom of shampoo etc., discharge outlet, near the tap, the hard surface of the water line section in the closet of toilet etc.
In addition, " pink dirt " refers to the dirt from microorganism that a little just presents partially red color take attachment or mucus as representative.At this, partially red color comprises the Neutral colour of redness, pink or these colors.For example, can be near 490nm, have maximum absorption wavelength color (mud that produces in the living environment such as bathroom: fungi-proofing mildew-resistant vol.24, No.11, p.723-728,1996).
In the organic solvent of composition (B), as aromatic alcohols, preferred benzylalcohol, BOE, phenoxetol, 1-phenoxy group-2-propyl alcohol etc., wherein further preferred benzylalcohol.
As aromatic aldehyde, preferred benzaldehyde, phenylacetaldehyde, 4-tolyl aldehyde, 2-benzenpropanal etc., wherein, preferred further benzaldehyde, phenylacetaldehyde.
In the aldehyde compound shown in hydroxy compounds shown in the formula (1), the formula (2), be 1 ~ 10 alkylidene as the represented carbon number of A, be preferably carbon number and be 2 or 3 alkylidene.
As the alkyl or the thiazolinyl that by the represented carbon number of R are 5 ~ 10, can be that straight chain can be side chain also, be preferably carbon number and be 5 ~ 8 alkyl, such as enumerating normal-butyl, n-hexyl, 2-ethylhexyl etc.
N is 0 ~ 3 number, is preferably 1 ~ 3, is more preferably 1 or 2.In addition, n A is identical or different.
As the preferred object lesson of the organic solvent of composition (B), such as enumerating benzylalcohol, glycol monomethyl n-butyl ether, ethylene glycol ether, 2-(2-ethyl hexyl oxy) ethanol, diethylene glycol list n-butyl ether, diethylene glycol monohexyl ether, 2-[2-(2-ethyl hexyl oxy) ethyoxyl] ethanol, 2-BOE, 2-phenoxetol, benzaldehyde, phenylacetaldehyde, 4-tolyl aldehyde, 2-benzenpropanal, hexanal, 2-ethyl butyraldehyde, diethylene glycol single-benzyl ether, amylalcohol, 1-phenoxy group-2-propyl alcohol etc.
Therefore, as the preferred compositions of composition (A) and composition (B), can enumerate following situation:
Composition (A) is for being selected from octyl group benzyl dimethyl ammonium chloride, in dodecylbenzyl alkyl dimethyl ammonium chloride and the DDAC more than a kind, composition (B) is for being selected from benzylalcohol, the glycol monomethyl n-butyl ether, ethylene glycol ether, the 2-(2-ethyl hexyl oxy) ethanol, diethylene glycol list n-butyl ether, the diethylene glycol monohexyl ether, the 2-[2-(2-ethyl hexyl oxy) ethyoxyl] ethanol, the 2-BOE, the 2-phenoxetol, benzaldehyde, phenylacetaldehyde, the 4-tolyl aldehyde, the 2-benzenpropanal, hexanal, 2-ethyl butyraldehyde, the diethylene glycol single-benzyl ether, the situation more than a kind in amylalcohol and the 1-phenoxy group-2-propyl alcohol;
Composition (A) for be selected from octyl group benzyl dimethyl ammonium chloride, dodecylbenzyl alkyl dimethyl ammonium chloride and the DDAC more than a kind, composition (B) is for being selected from the situation more than a kind in benzylalcohol, ethylene glycol ether and the diethylene glycol list n-butyl ether;
Composition (A) is octyl group benzyl dimethyl ammonium chloride, (B) is the situation of benzylalcohol.
In antibacterial agent of the present invention, composition (A) and mass ratio (B) (A)/(B) are preferably 200/1 ~ 1/200, and more preferably 10/1 ~ 1/10.
Antibacterial agent of the present invention, can only contain composition (A) and (B), perhaps also can be as required, be the further raising of antibacterial effect or the continuation of effect etc., and contain other composition, for example, chelating agent, water-soluble solvent, other cationic surfactant, spices, pH adjusting agent etc.In addition, also can be as the material of giving above-mentioned various living environment or the product that in living environment, uses or preparation (for example, scrubbing-and-drying unit cleaning agent, discharge outlet cleaning agent, tap age resister, bathing pool with cleaning agent, lavatory with cleaning agent etc.) antibiotic property.
At this, as chelating agent, can enumerate (1) tripolyphosphate, pyrophosphoric acid, orthophosphoric acid, hexa metaphosphoric acid and their alkali metal salt, (2) ethylenediamine tetra-acetic acid, hydroxyl imide base oxalic acid, dihydroxyethylglycin, NTA, HEDTA, diethylene-triamine pentaacetic acid, triethylenetetraaminehexaacetic acid and their alkali metal salt or alkali earth metal salt, (3) ATMP, 1-hydroxy ethylene-1, the 1-di 2 ethylhexyl phosphonic acid, ethylenediamine tetramethylene phosphonic acid, diethylenetriamine pentamethylenophosphonic acid, the N-oxide of ATMP and their alkali metal salt or alkali salt, (4) be selected from single polymers or the copolymer of the monomer in acrylic acid and the methacrylic acid, acrylic acid-maleic acid, poly-Alpha-hydroxy acrylic acid and alkali metal salt thereof, (5) be selected from citric acid, succinic acid, malic acid, fumaric acid, tartaric acid, malonic acid, in polybasic carboxylic acid in the maleic acid and their alkali metal salt more than a kind, (6) alkyl glycine-N, the N-oxalic acid, aspartic acid-N, the N-oxalic acid, serine-N, the N-oxalic acid, the glutamic acid oxalic acid, EDDS or their salt etc.
In addition, antibacterial agent of the present invention can be as required, suitably cooperate additives such as oil content, higher fatty acid, silicone, pH adjusting agent, tackifier, suspension, powder composition, natural extract, pigment, spices, mix and make it dispersing and dissolving, thereby make antimicrobial composition of the present invention.
At this, can be separately or the inorganic acids such as compound use hydrochloric acid or sulfuric acid as pH adjusting agent, the perhaps sour agent such as organic acid such as citric acid, succinic acid, malic acid, fumaric acid, tartaric acid, malonic acid, maleic acid, perhaps sodium hydroxide or potassium hydroxide, the ammonia or derivatives thereof, the amine salt such as MEA or diethanol amine, triethanolamine etc., the alkaline agents such as sodium carbonate, potash.In addition, also can make up these sour agent and alkaline agent uses as system buffer.
The antimicrobial composition of the invention described above preferably is adjusted to 2 ~ 12 by above-mentioned pH adjusting agent with the pH under 20 ℃ from the viewpoint of antibiotic property, particularly preferably is adjusted to pH4 ~ 11.
The content of the composition in the antimicrobial composition of the present invention (A) is preferably 0.1 ~ 100,000ppm from the viewpoint of antibiotic property, and more preferably 10 ~ 10,000ppm.
In addition, the content of composition (B) is preferably 100ppm ~ 100,000ppm, and 100ppm ~ 50 more preferably, 000ppm is more preferably 2,000ppm ~ 20,000ppm.
More particularly, composition (A) and content (B), using octyl group benzyl dimethyl ammonium salt, dodecylbenzyl dimethyl ammonium or didecyldimethyl ammonium salt as composition (A), and use as composition (B) in the situation of benzylalcohol, for example can enumerate composition (A) is 2,000 ~ 6,000ppm, composition (B) is 5,000ppm ~ 20,000ppm; Composition (A) is 2,400 ~ 6,000ppm, and composition (B) is 5,000ppm; Composition (A) is 25 ~ 400ppm, and composition (B) is 2,000 ~ 5,000ppm etc.
In addition, using octyl group benzyl dimethyl ammonium salt as composition (A), dodecylbenzyl dimethyl ammonium or didecyldimethyl ammonium salt, and use benzylalcohol as composition (B), ethylene glycol ether, diethylene glycol list n-butyl ether, the diethylene glycol monohexyl ether, the 2-[2-(2-ethyl hexyl oxy) ethyoxyl] ethanol, the 2-BOE, the 2-phenoxetol, benzaldehyde, the diethylene glycol single-benzyl ether, in the situation of amylalcohol or 1-phenoxy group-2-propyl alcohol, for example, can enumerate composition (A) is 10 ~ 10,000ppm, composition (B) is 4,000 ~ 760,000ppm etc.
In addition, using octyl group benzyl dimethyl ammonium salt, dodecylbenzyl dimethyl ammonium or didecyldimethyl ammonium salt as composition (A), and use as composition (B) in the situation of diethylene glycol list n-butyl ether or ethylene glycol mono hexyl ether, for example can enumerate composition (A) is 10,000 ~ 100,000ppm, composition (B) is 100ppm ~ 100,000ppm etc.
In addition, as mentioned above, antibacterial agent of the present invention can be only by composition (A) and (B), perhaps with other composition together, perhaps be matched with in the product that in various living environments, uses or the preparation and use, no matter but in which kind of situation, all preferably use with composition (A) when contacting with microorganism and the mode of concentration (B) in above-mentioned scope.Therefore, antimicrobial composition of the present invention also can be to infer dilution to be the composition that further concentrates in the above-mentioned scope under actual operating position.
Antibacterial agent of the present invention or the bactericidal composition that contains this antibacterial agent can be prevented adhering to of pink dirt or remove pink dirt by the place that is applied to easy generation microbial contamination.
Particularly, antibacterial agent of the present invention or contain the antimicrobial composition of this antibacterial agent can be in the living environment, (the bathroom, living space that raises easily of temperature or humidity particularly, the kitchen, the washroom, toilet etc.) etc. produce easily the hard surface in the place of microbial contamination, for example, for kitchen or bathroom, the toilet, the wall of washstand etc. or floor, the bottom of washing bucket, the bottle bottom of shampoo etc., discharge outlet, near the tap, water line section in the closet of toilet etc., before producing pink dirt or after producing, use by coating.At this, coating method is not particularly limited, and can enumerate composition directly is applied on the object face, is filled in and sprays in the sprayer units such as trigger (Trigger) or aerosol etc.
Embodiment
Below, based on embodiment the present invention is further elaborated.
The analysis of the pathogen of reference example 1 pink dirt
(1) carries out the analysis of the pathogen of pink dirt by the SEM observation
From the bathroom of 14 families, wipe the pink dirt of getting 39 sample bathrooms with toothpick, after outstanding turbid the fixing of the glutaraldehyde solution with 2.5%, with the 100mM phosphate buffer cleaning of pH7.6, dewater with rising gradient ethanol system.Again after the upper evaporation platinum vanadium in surface, use scanning electron microscope (SEM) (S4300SE/N, Hitachi) under 7 ~ 15kV, to observe after further freeze-dried.An example of SEM observed result is shown in Fig. 1.
In whole samples, all bacteriums all are the following sizes of 3 μ m basically, do not observe the above bacterium of 5 μ m.That is, in whole samples, there is advantage in the bacterium with bacterium size and shape, and there is not advantage in the bacterium of yeast size.Therefore, the main pathogenic fungi that represents pink dirt be not yeast rhodotorula (
Rhodotorula) belong to.
(2) use is by the analysis of the microscopical pink dirt of confocal laser of FISH
The bathroom of 13 families reclaims 17 samples of the container that is attached with pink dirt, cut simultaneously with the pink dirt on this container with the part of pink dirt and to take off, be placed on 3%(v/v) fix 2 hours in the paraformaldehyde aqueous solution (Sigma-Aldrich Japan K.K.).Remove after the unnecessary moisture with paper handkerchief, be embedded in the polyacrylamide gel.With this embedding sample use for detection of the methyl bacillus (
Methylobacterium) belong to the fluorescence probe of bacterium (to AGCGCCGTCGGGTAAGA(sequence number 1, Pirttila, A., M., Laukkanen, H., Pospiech, H., Myllyla, R., and Hohtola, Anja. (2000) " Detection of intracellular bacteria in the buds of Scotch pine (
Pinus sylvestrisL.) by in situ hybridization. " Appl.Envion.Microbiol.vol.66 (7): 3073-3077.); modified the probe of rhodamine (rhodamine) X at 5 ' end side) hybridize processing; next again with fluorescence probe (the GCTGCCTCCCGTAGGAGT(sequence number 2; Amann; R.; I. that can detect most bacteriums, Krumholz, L., and Stahl, D., A. (1990) " Fluorescent-oligonucleotide probing of whole cells for determinative; phylogenetic; and environmental studies in microbiology. " J Bacteriol.vol.172 (2): 762 – 770.), modified the probe of fluorescein isothiocyanate (fluorescein isothiocyanate) at 5 ' end side) hybridize processing after, with the fluorometric reagent Calcofluor white(BD that is used in particular for dyeing to containing more polysaccharide in the fungi) dye, (Carl Zeiss LSM META) observes with confocal laser microscope (CLSM).In addition, in the hybridization of fluorescence probe is processed, for improve the methyl bacillus (
Methylobacterium) belong to Bacteria Detection and use assist probes with the specificity of probe and fluorescence intensity.Probe is not for modifying the oligonucleotides of fluorchrome, design AGCGCCGTCTGGTAAGA(sequence number 3) and CCAACTCCCATGGTGACGA(sequence number 4) use.Assist probes improves specificity to the binding sequence of probe by being combined with the sequence similar with the binding sequence of probe, perhaps, by and the calmodulin binding domain CaM of probe near DNA in conjunction with the three-dimensional structure that changes DNA, thereby performance makes probe be incorporated into easily effect on the binding sequence.Assist probes is to add simultaneously with mode and the probe of the identical molal quantity of probe.An example of CLSM picture as shown in Figure 2.Red expression methyl bacillus (
Methylobacterium) belong to bacterium, yellow green and represent other bacterium, light blue expression mould and polysaccharide.
In observed whole 17 samples, hinted the methyl bacillus (
Methylobacterium) belong to bacterium and exist advantageously.Thus hint produce the main pathogenic fungi of pink dirt be the methyl bacillus (
Methylobacterium) the genus bacterium.
The analysis of the pink dirt that (3) is undertaken by the separation of bacterium
The pink dirt of 17 samples that will from the bathroom of 13 families, gather (sample A ~ Q), use potato dextrose agar (Potato Dextrose Agar, PDA) (Difco), PDA+ chloramphenicol (Chloramphenicol) (50 μ g/ml), nutrient agar (Nutrient Agar, NA) (Difco) as medium, at room temperature cultivate in 3 days.In this state, because various bacteriums can form overlapping bacterium colony on agar medium, therefore, use each bacterium colony of platinum loop picking, be inoculated on the new medium, to R2A under 25 ℃, other medium is cultivated 3 ~ 7 day time under 30 ℃, and repeatedly repeated this operation, isolate mushroom.To the analysis by the biochemical proterties of using API test (bioMerieux) be estimated as the methyl bacillus (
Methylobacterium) belong to the bacterial classification of bacterium, determine the base sequence of the DNA in its 16SrRNA zone, by homology search and the evaluation of carrying out bacterial classification based on the network analysis of base sequence.
Except the rhodotorula that judges by morphologic observation (
Rhodotorula) belong to beyond the yeast, also isolated a lot of methyl bacillus (
Methylobacterium) the genus bacterium.
The analysis result of sample A ~ Q is as shown in table 1.The result is presented in the pink dirt and not only has bacterium but also have yeast, but in the bacterium that exists substantially by the methyl bacillus (
Methylobacterium) to belong to bacterium occupied.
[table 1]
Notes) zero this bacterium of expression in the table is detected.
Reference example 2 methyl bacillus (
Methylobacterium) belong to the antibacterial agent patience of bacterium
Will be from reference example 1(3) separate among the bathroom pink dirt sample F of record identify have a liking for middle temperature methyl bacillus (
M.mesophilicum) thalline of FP4 uses PDA plating medium (Difco) 30 ℃ of lower cultivations a night, on the picking one platinum loop medium have a liking for middle temperature methyl bacillus (
M.mesophilicum) thalline of FP4, cultivated 3 days 30 ℃ of lower concussions in the outstanding turbid potato glucose liquid nutrient medium in other (Potato Dextrose Broth, PDB).(7000g * 5min.) removes after the supernatant, makes it outstanding turbid with the physiological saline of equivalent with its centrifugation.Afterwards again centrifugation (7000g * 5min.), be modulated into the bacterium liquid of OD0.8 with physiological saline.With respect to this bacterium liquid of 10 μ l, add the water-reducible octyl group benzyl dimethyl ammonium chloride solution (SANISOL08, Kao Corp) of sterilizing of using of 1ml, make it to contact 5 minutes.Then with respect to lecithin-polysorbate (LP, Lecithin Polysorbate) dilution (with the pure pharmaceutical worker's industry of light) is 1/10th amount interpolation dilution octyl group benzyl dimethyl ammonium chloride, make it inactivation, try to achieve the survival bacterial population by the agar semar technique.According to same step modulation Escherichia coli (
E.coli) NBRC3972, staphylococcus aureus (
S.aureus)NBRC13276 and pseudomonas aeruginosa (
P.aeruginosa)NBRC13275(is by Biological Genetic Resources department of NBRC(independent administrative corporation product evaluation technical foundation mechanism) buy) bacterium liquid, try to achieve the survival bacterial population after octyl group benzyl dimethyl ammonium chloride solution adds.
As shown in table 2, Escherichia coli (
E.coli), staphylococcus aureus (
S.aureus), pseudomonas aeruginosa (
P.aeruginosa)In by contacting 5 minutes with the octyl group benzyl dimethyl ammonium chloride solution of the concentration of 240 ~ 480ppm, can observe the above bacterial population of log2 and reduce, with respect to this, have a liking for middle temperature methyl bacillus (
M.mesophilicum) in by contacting with the octyl group benzyl dimethyl ammonium chloride solution of 6000ppm concentration in 60 minutes the situation, can observe significant bacterial population and reduce.By this result, demonstration methyl bacillus (
Methylobacterium) belong to bacterium and have very high patience with respect to antibacterial agent.
By this result also hint the high methyl bacillus of survival ability (
Methylobacterium) to belong to bacterium be the main pathogenic fungi of pink dirt.
[table 2]
*Numeric representation in the table contacts the log value of the minimizing bacterial population (c.f.u./ml) after each time.
* 1) octyl group benzyl dimethyl ammonium chloride concentration (ppm)
1 pair of methyl bacillus of embodiment (
Methylobacterium) belong to the evaluation (1) of the antimicrbial power of bacterium
According to reference example 2 same steps modulation have a liking for middle temperature methyl bacillus (
M. Mesophilicum) FP4 bacterium liquid.In addition, according to the steps modulation octyl group benzyl dimethyl ammonium chloride solution same with reference example 2 (2400 ~ 6000ppm), to wherein adding benzylalcohol (BA) to 5000ppm.With this octyl group benzyl dimethyl ammonium chloride+BA solution (1ml) add to have a liking for middle temperature methyl bacillus (
M.mesophilicum) contact 5 minutes in the FP4 bacterium liquid (10 μ l) with bacterium.The result is as shown in table 3.
As shown in Table 3, be in the solution of 2400 ~ 6000ppm using and in 5 minute contact time, do not have the octyl group benzyl dimethyl ammonium chloride concentration of antibiotic property separately, by adding BA5000ppm, can obtain high combined effect.
[table 3]
2 pairs of methyl bacillus of embodiment (
Methylobacterium) belong to the evaluation (2) of the antimicrbial power of bacterium
According to the various methyl bacillus shown in the same step modulomenter 4 of reference example 2 (
Methylobacterium) genus Bacteria liquid.In addition, according to have a liking for middle temperature methyl bacillus (
M. Mesophilicum) the same method of FP4 separates from the bathroom and obtain
M.fujisawaenseGP1 and the methyl of anti-ray bacillus (
M.radiotolerans) AP2.Other bacterial strain is buied by Physical Chemistry Inst living resources center (BioResource Center).In addition, and the same steps modulation dodecylbenzyl alkyl dimethyl ammonium chloride solution of reference example 2 (39 ~ 313ppm), to wherein adding benzylalcohol (BA) to 2000 ~ 5000ppm.This dodecylbenzyl alkyl dimethyl ammonium chloride+BA solution (1ml) is added in each Bacteria liquid (10 μ l) contacts 5 minutes with bacterium.The result is as shown in table 4.Order with " +++﹥ ++ ﹥+" in the table represents to confirm that vigorous propagation is arranged.On the other hand, "-" expression does not find to have breeding.Therefore, the step with " ﹥+﹥ ++ ﹥ +++" represents that antibiotic property is high.
Confirmed for whole bacterial strains by table 4, can improve antibiotic property by in the dodecylbenzyl alkyl dimethyl ammonium chloride, adding BA.
[table 4]
Have a liking for middle temperature methyl bacillus (M.mesophilicum) FP4
M.fujisawaense?GP1
The methyl of anti-ray bacillus (M.radiotolerans) AP2
Have a liking for middle temperature methyl bacillus (M.mesophilicum) JCM2829
Turn round demethylation bacillus (M.Extorquens) JCM2805
The methyl of anti-ray bacillus (M.radiotolerans) JCM2805
3 pairs of methyl bacillus of embodiment (
Methylobacterium) belong to the evaluation (3) of the antimicrbial power of bacterium
According to reference example 2 same steps modulation have a liking for middle temperature methyl bacillus (
M. Mesophilicum) FP4 bacterium liquid.In addition, according to the steps modulation octyl group benzyl dimethyl ammonium chloride solution same with reference example 2 (10 ~ 10000ppm), to wherein adding the various organic solvents shown in the table 5 to the concentration shown in the table 5.With this octyl group benzyl dimethyl ammonium chloride+organic solvent solution (1ml) be added into have a liking for middle temperature methyl bacillus (
M.mesophilicum) contact 5 minutes with bacterium in the FP4 bacterium liquid (10 μ l).The result is as shown in table 5.
By confirming in the table 5, for benzylalcohol, ethylene glycol ether, diethylene glycol monohexyl ether, 2-[2-(2-ethyl hexyl oxy) ethyoxyl] use separately as solvent the ethanol, 2-BOE, 2-phenoxetol, diethylene glycol single-benzyl ether, amylalcohol, 1-phenoxy group-2-propyl alcohol, benzaldehyde, diethylene glycol list n-butyl ether, perhaps do not have under the concentration of antibiotic property with the independent use of octyl group benzyl dimethyl ammonium chloride, have the effect with octyl group benzyl dimethyl ammonium chloride and usefulness.
[table 5]
4 pairs of methyl bacillus of embodiment (
Methylobacterium) belong to the evaluation (4) of the antimicrbial power of bacterium
According to reference example 2 same steps modulation have a liking for middle temperature methyl bacillus (
M. Mesophilicum)FP4 bacterium liquid.In addition according to the steps modulation octyl group benzyl dimethyl ammonium chloride solution same with reference example 2 (10000 ~ 100000ppm), to wherein adding various organic solvents shown in the table 6 to the concentration of putting down in writing.With add in this octyl group benzyl dimethyl ammonium chloride+organic solvent solution (1ml) have a liking for middle temperature methyl bacillus (
M.mesophilicum) FP4 bacterium liquid (10 μ l) makes it to contact 1 minutes.The result is as shown in table 6.
Can be confirmed by table 6, for using separately as solvent with diethylene glycol list n-butyl ether, ethylene glycol ether, perhaps do not show the concentration of antibiotic property with the independent use of octyl group benzyl dimethyl ammonium chloride and under time of contact, have and effect octyl group benzyl dimethyl ammonium chloride and usefulness.
[table 6]
5 pairs of methyl bacillus of embodiment (
Methylobacterium) belong to the evaluation (5) of the antimicrbial power of bacterium
According to embodiment 2 same steps modulation have a liking for middle temperature methyl bacillus (
M. Mesophilicum)FP4 bacterium liquid.In addition according to the quaternary ammonium salt solution (25ppm or 400ppm) shown in the same step modulomenter 7 of reference example 2, to wherein adding benzylalcohol to 5000ppm.With this quaternary ammonium salt+benzylalcohol solution (1ml) be added into have a liking for middle temperature methyl bacillus (
M.mesophilicum)Contact 5 minutes in the FP4 bacterium liquid (10 μ l) with bacterium.The result is as shown in table 7.
Can be confirmed except octyl group benzyl dimethyl ammonium chloride, also to have very high combined effect in dodecylbenzyl alkyl dimethyl ammonium chloride or the DDAC by table 7.
[table 7]
*BA+ has represented to add the system of BA in the table, and BA-represents not add the system of BA.
Embodiment 6 is for the clean-up performance evaluation of model pink dirt
According to reference example 2 same steps modulation have a liking for middle temperature methyl bacillus (
M. Mesophilicum) FP4 bacterium liquid (OD0.8).Next, fibre reinforced composites with 10 * 10 * 2(mm) (Fiber Reinforced Plastics, being called for short FRP) section use the UV radiation sterilization after impregnated in ethanol, this FRP section of packing in the microtiter plates (Microtiter dish), interpolation 1mL bacterium liquid.It is left standstill cultivation 6 days under 30 ℃, only the FRP section is transplanted in the 24 new orifice plates, at 30 ℃ of lower dry one late analogue formation pink dirts.
Dipping is attached with the FRP section of model dirt in octyl group benzyl dimethyl ammonium chloride (10000ppm) solution or octyl group benzyl dimethyl ammonium chloride (10000ppm)+BA(5000ppm) solution, after leaving standstill 5 minutes, with the section dislocation in dispensing the test tube of LP dilution of 1mL, by peeling off bacterium with the vortex mixer high degree of agitation, make it to disperse, mensuration is peeled off, the bacterial population of dispersed bacterium.To peel off in addition, the section of the FRP after the disperse bacterial packs in the microtiter plates again, leaves standstill cultivation under 30 ℃, measures the time that bacterium breeds again.The result is shown in table 8 and table 9.
Impregnated in octyl group benzyl dimethyl ammonium chloride, added BA solution for the methyl bacillus (
Methylobacterium) belong in the FRP section in the solution that bacterium has high degerming ability, bacterial population has greatly reduced.And extremely the upper bacterium of section breeds again needs the plenty of time.On the other hand, in the FRP section that impregnated in octyl group benzyl dimethyl ammonium chloride solution, bacterial population does not reduce, and finds rapidly the again propagation of bacterium.
[table 8]
*BA+ has represented to add the system of BA in the table, and BA-represents not add the system of BA.
[table 9]
| ? | Water | Octyl group benzyl dimethyl ammonium chloride | Octyl group benzyl dimethyl ammonium chloride+BA |
| 2 days | 6/6 | 3/6 | 0/6 |
| 3 days | 6/6 | 5/6 | 0/6 |
| 5 days | 6/6 | 6/6 | 1/6 |
| 6 days | 6/6 | 6/6 | 3/6 |
*Pollute the time that needs after antibiotic property shown in the table test, denominator represents the sum of pilot region in the table again, and minute subrepresentation is polluted test region number again.
Claims (16)
1. antibacterial agent, wherein,
Described antibacterial agent is the quaternary ammonium salt that following composition (A) is represented and (B) antibacterial agent that combines of represented organic solvent,
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt,
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2),
In the formula, R represents that carbon number is 5 ~ 10 alkyl, thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.
2. antibacterial agent as claimed in claim 1, wherein,
The organic solvent of composition (B) is that carbon number is that 1 ~ 3 alkylidene and n are the organic solvent more than a kind in the compound of 0 ~ 2 number for being selected from A in the represented compound in formula (1) and (2).
3. antibacterial agent as claimed in claim 1, wherein,
The organic solvent of composition (B) is for being selected from benzylalcohol, ethylene glycol ether, diethylene glycol list n-butyl ether, diethylene glycol monohexyl ether, 2-[2-(2-ethyl hexyl oxy) ethyoxyl] in ethanol, 2-BOE, 2-phenoxetol, benzaldehyde, diethylene glycol single-benzyl ether, amylalcohol and the 1-phenoxy group-2-propyl alcohol more than a kind.
4. antibacterial agent as claimed in claim 1, wherein,
The organic solvent of composition (B) is benzylalcohol.
5. require the described antibacterial agent of any one in 1 ~ 4 such as power, wherein,
The quaternary ammonium salt of composition (A) be selected from octyl group benzyl dimethyl ammonium salt, dodecylbenzyl dimethyl ammonium and the didecyldimethyl ammonium salt more than a kind.
6. antibacterial agent as claimed in claim 5, wherein,
Ammonium salt is the salt with chloride ion.
7. antibacterial agent as claimed in claim 1, wherein,
The quaternary ammonium salt of composition (A) is octyl group benzyl dimethyl ammonium chloride, and the organic solvent of composition (B) is benzylalcohol.
8. such as the described antibacterial agent of any one in the claim 1 ~ 7, wherein,
With respect to the methyl bacillus (
Methylobacterium) belong to bacterium and have antibacterial action.
9. antimicrobial composition, wherein,
Contain just like the described antibacterial agent of any one in the claim 1 ~ 8.
10. antimicrobial composition as claimed in claim 8, wherein,
In composition, contain composition (A) 0.1 ~ 100,000ppm, composition (B) 100ppm ~ 100,000ppm.
11. antimicrobial composition as claimed in claim 10, wherein,
Use octyl group benzyl dimethyl ammonium salt, dodecylbenzyl dimethyl ammonium or didecyldimethyl ammonium salt as composition (A), use as composition (B) in the situation of benzylalcohol, contain composition (A) 2,000 ~ 6,000ppm, composition (B) 5,000ppm ~ 20,000ppm perhaps contains composition (A) 2,400 ~ 6,000ppm, composition (B) 5,000ppm perhaps contains composition (A) 25 ~ 400ppm, composition (B) 2,000 ~ 5,000ppm.
12. a pink dirt prevent from adhering to or removing method, it is characterized in that,
To or be applied to the place of easy generation microbial contamination such as the described antimicrobial composition of any one in the claim 9 ~ 11 such as the described antibacterial agent of any one in the claim 1 ~ 8.
13. the quaternary ammonium salt that following composition (A) is represented and (B) combination of represented organic solvent as the purposes of antibacterial agent,
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt,
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2),
In the formula, R represents that carbon number is 5 ~ 10 alkyl, thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.
14. the quaternary ammonium salt that following composition (A) is represented and (B) combination of represented organic solvent for the manufacture of the purposes in the antibacterial agent,
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt,
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2),
In the formula, R represents that carbon number is 5 ~ 10 alkyl, thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.
15. an antibiotic method is characterized by,
Be used in combination the represented quaternary ammonium salt of following composition (A) and (B) represented organic solvent,
(A) be selected from the quaternary ammonium salt more than a kind in dialkyl dimethyl ammonium salt and the alkyl benzyl dimethyl ammonium salt,
(B) be selected from the organic solvent more than a kind in the represented compound in aromatic alcohols, aromatic aldehyde, following formula (1) and (2),
In the formula, R represents that carbon number is 5 ~ 10 alkyl, thiazolinyl or benzyl, and A represents that carbon number is 1 ~ 10 alkylidene, and n represents 0 ~ 5 number, and n A is identical or different.
16. antibiotic method as claimed in claim 15, wherein,
Described antibiotic method suppress or stop contain the methyl bacillus (
Methylobacterium) belong to the microbial growth breeding of bacterium.
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| JP2014132062A (en) * | 2012-12-07 | 2014-07-17 | Kao Corp | Liquid detergent composition for hard surface |
| JP2014132063A (en) * | 2012-12-07 | 2014-07-17 | Kao Corp | Liquid detergent composition for hard surface |
| CN104509532A (en) * | 2015-01-07 | 2015-04-15 | 北京中海诚达科贸有限公司 | Ionic targeted sterilization intermediate compounding technology |
| CN106993613A (en) * | 2017-03-31 | 2017-08-01 | 蒙建都 | A kind of ion targeting sterilizing intermediate compounded technology |
| WO2023123421A1 (en) * | 2021-12-31 | 2023-07-06 | 振德医疗用品股份有限公司 | Long-acting antibacterial disinfectant, preparation method therefor and application thereof |
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| JP5784920B2 (en) * | 2011-02-10 | 2015-09-24 | 花王株式会社 | Anti-residential fungi |
| JP6345427B2 (en) * | 2014-01-30 | 2018-06-20 | 花王株式会社 | Microbicidal composition |
| JP6249404B2 (en) * | 2014-03-10 | 2017-12-20 | 花王株式会社 | Liquid deodorant disinfectant composition |
| JP7042553B2 (en) * | 2014-04-08 | 2022-03-28 | アークサーダ，エルエルシー | Fast-acting disinfectant composition |
| JP6334265B2 (en) * | 2014-05-29 | 2018-05-30 | 花王株式会社 | Screening method for antibacterial substances |
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