WO2002100174A1 - Liquid deodorant killing microorganism and method of microorganism-killing deodorization - Google Patents
Liquid deodorant killing microorganism and method of microorganism-killing deodorization Download PDFInfo
- Publication number
- WO2002100174A1 WO2002100174A1 PCT/JP2002/005593 JP0205593W WO02100174A1 WO 2002100174 A1 WO2002100174 A1 WO 2002100174A1 JP 0205593 W JP0205593 W JP 0205593W WO 02100174 A1 WO02100174 A1 WO 02100174A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- microbicidal
- dimethylhydantoin
- deodorant
- halogenated
- group
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
-
- 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
- A01N43/10—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 sulfur 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/72—Treatment of water, waste water, or sewage by oxidation
- C02F1/76—Treatment of water, waste water, or sewage by oxidation with halogens or compounds of halogens
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/02—Odour removal or prevention of malodour
Definitions
- the present invention relates to a microbicidal deodorant liquid, a microbicidal deodorant method using the same, and a method for stabilizing the microbicidal deodorant liquid.
- Novel microbicidal liquid containing a halogenated dialkylhydantoin and a halogenated succinimide, a microbicidal method using the same, a deodorant liquid, a deodorizing method using the same, and stabilization of each of these agents About the method.
- the slime refers to a viscous mass or a mud-like substance mainly composed of a high-molecular-weight polysaccharide secreted by a microorganism and incorporating various suspended substances in water.
- the slime when slime is generated in heat exchangers and pipes of cooling water systems in chemical factories, etc., it lowers cooling efficiency and sometimes blocks pipes.
- the slime when slime is generated on the pipe wall in the paper making process of a paper mill, the slime separates and mixes with the white water, causing spots and coloring on the product paper, thereby deteriorating the quality. Partially weakened, causing paper breakage and forced to suspend continuous operation. Therefore, controlling the microorganisms that cause this is an important issue.
- chlorine gas Conventionally, chlorine gas, sodium hypochlorite, Reamed or rolled solutions, tablets or powders of chlorinated isocyanuric acid have been used.
- chlorine gas has the disadvantages of extremely high risk of leakage and difficult handling.
- hypochlorous acid-based drugs do not penetrate slime and do not effectively act on bacterial cells.
- these drugs have problems such as loss of activity due to organic substances in water, and cannot be expected to have sufficient efficacy. It is known that it has an activity (Zn. Mikrobiol., Epidemiol. Immunobiol vol. 14, No. 9, P14-18, 1967, Japanese Patent Publication No. 46-27270).
- these compounds are distributed in a solid form such as tablets, powders or granules, and are used in this form at the site of use. Therefore, when these compounds are used, there is a problem in handling safety, such as dusting during work, which may cause skin damage, mucous membrane inflammation, and other effects on the human body. And other operational problems.
- these compounds are slow in dissolving and penetrating into target systems in terms of microbicidal efficacy. Therefore, in order to obtain a sufficient effect in a short time, it is necessary to add a large amount of these compounds.
- these compounds are used in an aqueous system with a low recirculation rate, for example, in some industrial cooling waters or papermaking process waters, the added compounds are discharged out of the system before the dissolution is completed.
- a water system with a high recirculation rate for example, cooling water for air conditioning
- the dissolution rate of the input compound is slow, so that the possibility that resistant bacteria will develop in this water system will be increased.
- liquid preparation of a bactericidal solid compound is an extremely effective means for reducing costs.
- amide is prepared as a liquid using a commonly used organic solvent, a large amount of irritating corrosive gas is immediately generated.
- the fungicidally active component is deactivated within a very short time, and cannot be used as a microbicidal or deodorant.
- Containing liquids have problems such as low corrosive gas generation and low stability.
- a liquid composition containing an octaethylgenated dialkylhydantoin derivative a method using a cyclic amide compound such as ⁇ -force prolactam / succinimide and water has already been proposed (JP-B-56-37). 9 No. 1 publication).
- this liquid composition is better in stability than liquid compositions using general organic solvents, its stability as a pharmaceutical preparation cannot be said to be sufficient.
- the object of the present invention is to solve the above-mentioned problems by using a halogenated dialkylhydantoin and ⁇ ⁇ ⁇ ⁇ or a halogenated succinimide as effective active ingredients, and having excellent operability, safety, stability and solubility, a microbicidal and deodorizing agent.
- the purpose of the present invention is to provide solutions and microbicidal and deodorizing methods.
- the present inventors have conducted intensive studies on the above problems, and as a result, have found that the main solvents are tetrahydrothiophene 1,1-dioxide, 3-methyltetrahydrothiophene 1,1 dioxide and 2,5-dihydrothiophene 1.1 dioxide.
- the use of at least one member selected from the group consisting of The result is a solution that is free and retains the active ingredient over a long period of time.
- a microbicidal solution and a deodorant solution in which succinimide is stabilized and a microbicidal method and a deodorizing method using the same. That is, the present invention includes the following.
- Y represents a halogen atom.
- Y represents a halogen atom.
- a microbicidal agent comprising at least one selected from the group consisting of 2,5-dihydrothiophene 1,1 dioxide.
- Halogenated dialkylhydantoin is 1,3-dibutane 5,5-dimethylhydantoin, 1-bromo-3-chloro-5,5-dimethylhydantoin, 3-promote 1-chloro-5,5-dimethylhydantoin, The microbicidal solution according to the above (1), which is promochloro-1,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin or 1,3-dichloro-5-ethyl-5-methylhydantoin.
- microbicidal agent which comprises:
- microbicidal agent according to any one of the above (1) to (4), further comprising at least one member selected from the group consisting of hydantoin, 5,5-dimethylhydantoin, succinimide and fluorimide.
- microbicidal liquid according to any one of the above (1) to (5), further comprising a known bactericide component.
- a microbicidal method comprising treating the microbicidal liquid according to any one of the above (1) to (6) into a microbicidal target system or a microbicidal target.
- a deodorant solution comprising: at least one selected from the group consisting of thiophene 1,1-dioxide and 2,5-dihydrothiophene 1,1-dioxide.
- the halogenated dialkylhydantoin is 1,3-dibutone-mode 5,5-dimethylhydantoin, 1-bromo-3-chloro-5,5-dimethylhydantoin, 3-bromo 1-chloro-5,5-dimethylhydantoin,
- the deodorant liquid according to the above (8) which is 5,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin or 1,3-dichloro-5-ethyl-5-methylhydantoin.
- the deodorant liquid according to the above (8), wherein the halogenated succinimide is N-chlorosuccinimide or N-bromosuccinimide.
- deodorant solution according to any one of the above (8) to (11), further comprising at least one selected from the group consisting of hydantoin, 5,5-dimethylhydantoin, succinimide and fluorimide.
- a deodorizing method which comprises treating the deodorant solution according to any one of the above (8) to (13) to a system to be deodorized or a substance to be deodorized.
- the halogenated dialkylhydantoin is represented by the general formula (1).
- Examples of the halogen represented by X 1 and X 2 in the general formula (1) include bromine and chlorine.
- X 1 and X 2 may be the same or different.
- Examples of the lower alkyl group represented by R 1 and R 2 include an alkyl group having 1 to 3, preferably 1 to 2 carbon atoms, such as a methyl group, an ethyl group, and a propyl group. These R 1 and R 2 may be the same or different.
- These halogenated dialkylhydantoins can be produced by obtaining dialkylhydantoins from dialkyl ketones, cyanide compounds and carbonates and halogenating them.
- Halogenated dialkylhydantoins are commercially available, and these can also be used.
- commercially available halogenated dialkylhydantoins include HALOCOM DBH (High Polymer Labs, the compound Al), Aquablom (AQUABR0M) (Great Lakes Chemical Co., Ltd.). (Great Lakes Chemical Corporation), the compound A2), and DANTOBROM RW (Lonza, a mixture of the compounds A4, A5, and A6).
- the halogenated succinimide used in the microbicidal deodorant solution is represented by the general formula (2).
- examples of the halogen represented by Y include bromine and chlorine.
- These halogenated succinimides are Synimide can be produced by halogenation using a halogenating agent, for example, a metal hypochlorite, a hypochlorite, or the like.
- halogenated succinimides can be used alone or in combination of two or more.
- microbicidal deodorant solution of the present invention can also be used.
- thiophene derivatives can be used alone or in combination of two or more. That is, in the microbicidal deodorant solution of the present invention, at least one selected from the group consisting of compound C1, compound C2 and compound C3 is used as the main solvent.
- the microbicidal deodorant solution of the present invention comprises at least one selected from the group consisting of a halogenated dialkylhydantoin (general formula (1)) and a halogenated succinimide (general formula (2)), and at least one of the aforementioned thiophene derivatives.
- the seeds are mixed and agitated. During the mixing and stirring, it is preferable to heat the mixture at 40 to 50 ° C. for about 10 minutes to 1 hour.
- auxiliary agent examples include at least one selected from the group consisting of hydantoin, 5,5-dimethylhydantoin, succinimide, and phthalimide.
- auxiliary agent By adding an auxiliary agent to the microbiocidal deodorant solution, the solubility of the halogenated dialkylhydantoin and / or the halogenated succinimide can be further increased.
- Auxiliary agents may be used alone or in combination of two or more as long as they are compounds selected from the above groups. Can also be used.
- the above-mentioned main solvent is preferably blended in an amount of 100 parts by mass or more with respect to 100 parts by mass of the halogenated dialkylhydantoin and / or halogenated succinimide, and more preferably 200 to 900 parts by mass. It is more preferable to mix them.
- the amount of the main solvent within this range, the stability of the microbicidal deodorant solution can be increased. It is preferable to mix in a range of 1 to 50 parts by weight, more preferably in a range of 5 to 20 parts by weight, based on 100 parts by weight of the cinimide.
- microbicidal deodorant solution of the present invention may be mixed with a generally used inexpensive organic solvent and / or water at the time of preparation or use.
- Examples of usable organic solvents include glycols such as ethylene glycol, diethylene glycol, dipropylene glycol, and polyethylene glycol; glycol ethers such as ethyl sorbent, methyl carbitol, and dipropylene glycol monomethyl ether; and propylene carbonate.
- Amides such as N-methylacetoamide, acetoamide, 2-pyrrolidinone, ⁇ -caprolactam, etc.
- alcohols such as octanol.
- propylene carbonate, 4-butyrolactone, 2-pyrrolidinone, and ⁇ -methylacetoamide are particularly preferably used. These organic solvents can be used alone or in combination of two or more.
- the microbicidal deodorant solution of the present invention may be diluted with these organic solvents and / or water at an arbitrary magnification.
- the mixing ratio of the organic solvent and / or water is preferably in the range of 1 to 99% by mass, more preferably in the range of 10 to 90% by mass, and further preferably in the range of 30 to 70% by mass. Most preferred.
- the microbicidal deodorant solution of the present invention may be used for microbicidal purposes, may be used for deodorizing purposes, or may be used for microbicidal and deodorizing purposes.
- the target of the microbicidal deodorant liquid, that is, the microbicidal deodorant target system and the microbicidal deodorant target are not particularly limited, and can be variously applied.
- the microbicidal deodorant solution of the present invention Can exhibit a faster microbicidal effect and / or a deodorant effect than solid products in a normal form.
- microbicidal deodorant examples include papermaking processes, industrial cooling water and washing water, cooling water for air conditioning, industrial water, pools, baths, activated sludge waste and residues, garbage, etc. it can.
- the microbicidal deodorant liquid can be effectively sterilized and bacteriostatic when used in the papermaking process, industrial cooling water, washing water, cooling water for air conditioning, industrial water, pools, baths, etc. It can also control slime.
- the microbicidal deodorant liquid can be effectively deodorized when used in activated sludge waste, residue, garbage, and the like.
- the appropriate dosage of the microbicidal deodorant liquid varies depending on the target system, the pH of the target substance, the content of organic and inorganic substances, the intensity of the odor, etc., and is selected as appropriate.
- the solution is introduced so as to be 0 ppm, preferably 5 to 100 ppm.
- the microbicidal deodorant solution of the present invention can provide an expanded antibacterial spectrum, and an additive or synergistic effect of antibacterial activity by being combined with a known bactericide component.
- Known bactericide components include 2,2-dibutene 2-nitroethanol, 2,2-dibutene 2-nitroethyl formate, 2,2-dibromo-2--2-troethyl acetate, 2,2 _Jib mouth mo 2-nitroethyl 2-propanoate, 2-bromo 2-nitropropane-1,3-diol, 2-bromo-2-nitropropane-1,3-diyl diformate, 2-bromo-2 —Nitropropane-1,3—dinitrodiacetate (hereinafter referred to as BNDA), etc., bromonitro compounds, methylene bisthiocyanate, 3,3,4,4-tetrachlorotetrahydrothiophene-1,1,1-dioxide, 5-chloro-1,
- Microorganisms that are the subject of the microbicidal deodorant solution of the present invention include bacteria, yeasts and filaments. Fungi such as fungi and algae can be mentioned. Examples of the bacteria include bacteria belonging to the genus Escherchia, bacteria belonging to the genus Pseudomonas, bacteria belonging to the genus Vibrio, bacteria belonging to the genus Enterobacter, bacteria belonging to the genus Serratia, and genus Legionella. Bacteria, Gram-negative bacteria such as Salmonel la bacteria, Staphylococcus bacteria, Bacillus bacteria, Streptococcus bacteria, Lactobacillus bacteria, etc. Can be exemplified.
- yeast examples include Saccharomyces, Candida, Geotrichum, Hansenula, Wiodotrula, Kluyveromyces, and Picliia. Etc. can be exemplified.
- filamentous fungi examples include Aspergillus, Penicullum, Trichoderma, Mucor, Rhizopus, Fusarium, and Cladosporium.
- Genus and Alternaria genus examples of the algae include the genus Chlorel la, the genus Oscilla lata, the genus Anabaena, the genus Senedesmus, and the genus Clostetium. Industrial applicability
- the microbicidal deodorant liquid agent of this invention can maintain the stable state over a long term from halogenated dialkyhydantoin and / or halogenated succinimide which were difficult to liquefy stably. Therefore, according to the present invention, it is possible to provide a microbicidal deodorant liquid which can be stored for a long time without changing its properties as a liquid.
- the microbicidal deodorant solution of the present invention is a liquid, it can exhibit a rapid microbicidal action and / or deodorant action not found in solid products. Therefore, it is possible to provide a microbicidal deodorant liquid that is free of powder, which is a drawback of solid products, and is excellent in safety and workability.
- each component was obtained by mixing and stirring and heating at 45 ° C. for 15 minutes.
- the mixture of compounds A4, A5 and A6 used in the test was a mixture of 60 parts by weight, 30 parts by weight and 10 parts by weight, respectively.
- a test tube with a volume of 20 ml is filled with the compound, etc., with the composition shown in Table 1, and bubbles are left with a silicon stopper through which a glass tube bent into a U-shape is inserted to discharge the generated gas. Plugged so as not to.
- the entire device was gently placed in a glass beaker and the mouth of the beaker was covered with aluminum foil. This was allowed to stand in a constant temperature incubator at 40 ° C for a specified number of days. The amount of gas generated over time was read from the scale, and the state of corrosion of the aluminum foil by the generated gas was observed. The results are shown in Tables 2 and 3. Tables 2 and 3 show the results of two separate runs under the above-mentioned conditions, respectively.
- the bacterium belonging to the genus Escherichia washed with the cells was diluted with a pH 8 phosphate citrate buffer to about 1 O SCFUZml, and 1 L of the diluted solution was added to a glass beaker. To this was added the powdered bulk of Example 1 or Example 8 and Compound A1 so as to have a predetermined concentration (indicated by the active ingredient), and the mixture was stirred for 90 minutes. After 5 10 30 and 90 minutes, a portion was taken and diluted with sterile water. The diluted solution was inoculated on a normal agar medium and cultured in a thermostat at 30 ° C for 3 days to count the number of viable cells. The results are shown in Tables 6 and 7 for CFUZm 1. Tables 6 and 7 show the results of two separate runs under the conditions described above.
- Example has higher solubility in the microbicidal target than the solid form, and exhibits excellent bactericidal efficacy in a very short time. . This property is required for sterilization and slime control applications such as papermaking process water, various industrial cooling water, and washing water, which require rapid sterilization. From these results, it can be seen that the Example is a microbicidal deodorant liquid suitable for disinfecting and preventing slime of papermaking process water or the like, which requires quick disinfecting power.
- Test example 4 (Deodorizing effect persistence test of activated sludge)
- the deodorizing effect was tested using activated sludge (dewatered cake, water content 70%) from a certain sewage treatment plant.
- the obtained activated sludge was made into a 40% suspension with distilled water, and a predetermined amount (indicated by an active ingredient) of the powder of Example 9, Comparative Example 2, or Compound A2 was added to the suspension and stirred. .
- 200 g of the suspension containing the powder of Example 9, Comparative Example 2 or Compound A2 was transferred to a 1 L Erlenmeyer flask, and two glass tubes provided with a rubber tube and a pinch cock were provided. The 1 L Erlenmeyer flask was stoppered with a rubber stopper.
- the example shows an excellent deodorizing effect within a shorter time than the solid form. From this result, it was found that the example was a microbicidal deodorant liquid which exhibited an excellent deodorizing effect in a short time. In addition, even in the case where the stirring was particularly weak and the mixing was insufficient, the Example showed sufficient deodorizing effect in a smaller amount and quickly because it sufficiently dissolved and penetrated into the object.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/343,749 US6881418B2 (en) | 2001-06-08 | 2002-06-06 | Liquid deodorant killing microorganism and method of microorganism-killing deodorization |
EP02738630A EP1393628A4 (en) | 2001-06-08 | 2002-06-06 | MICROORGANISMS KILL THE LIQUID DESODORING AGENT AND PROCESS FOR MICROORGANISM KILLING DESODORATION |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001-174176 | 2001-06-08 | ||
JP2001174176 | 2001-06-08 |
Publications (1)
Publication Number | Publication Date |
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WO2002100174A1 true WO2002100174A1 (en) | 2002-12-19 |
Family
ID=19015500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2002/005593 WO2002100174A1 (en) | 2001-06-08 | 2002-06-06 | Liquid deodorant killing microorganism and method of microorganism-killing deodorization |
Country Status (4)
Country | Link |
---|---|
US (1) | US6881418B2 (ja) |
EP (1) | EP1393628A4 (ja) |
CN (1) | CN1494378A (ja) |
WO (1) | WO2002100174A1 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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PL218746B1 (pl) * | 2002-12-20 | 2015-01-30 | Lonza Ag | Sposób dezintegracji biofilmu w środowisku wodnym oraz sposób usuwania biofilmu z podłoża w środowisku wodnym |
US7704380B2 (en) * | 2004-04-07 | 2010-04-27 | K•I Chemical Industry Co., Ltd. | Method of removing sulfides including hydrogen sulfide and mercaptan |
US7793666B2 (en) * | 2005-07-28 | 2010-09-14 | Innovation Biomedical Devices, Inc. | Apparatus and method for treatment of infected nail |
CN100407923C (zh) * | 2005-12-19 | 2008-08-06 | 南京工业大学 | 一种杀菌消毒剂及其应用 |
US20070196359A1 (en) * | 2006-02-23 | 2007-08-23 | Minntech Corporation | Halosuccinimide biocide |
WO2010011354A2 (en) * | 2008-07-25 | 2010-01-28 | Innovation Biomedical Devices, Inc. | Enchanced trans-keratin drug delivery |
EP2165981A1 (en) * | 2008-08-21 | 2010-03-24 | Lonza, Inc. | Antimicrobial water treatment |
RS62386B1 (sr) | 2014-10-21 | 2021-10-29 | Hexima Ltd | Postupak za lečenje gljivičnih infekcija |
CN106824054A (zh) * | 2017-01-23 | 2017-06-13 | 福建海西滤水龙头研究中心有限公司 | 一种吸附型杀菌除臭过滤芯及其制作方法 |
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CH478866A (de) * | 1967-06-09 | 1969-09-30 | Inventa Ag | Verfahren zur Herstellung von hitzebeständigen, linearen, thermoplastischen aromatischen Polythioäthern |
US4119535A (en) * | 1973-04-16 | 1978-10-10 | White Eugene B | Method of sanitizing a volume of water in conjunction with chlorine |
JPS5334923A (en) * | 1976-09-14 | 1978-03-31 | Kurita Water Ind Ltd | Industrial fungicide |
JPS56158333A (en) * | 1980-05-13 | 1981-12-07 | Teijin Chem Ltd | Treatment of waste photographic developer |
JPH1147755A (ja) * | 1997-07-29 | 1999-02-23 | Hakuto Co Ltd | スライムコントロール剤および方法 |
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2002
- 2002-06-06 WO PCT/JP2002/005593 patent/WO2002100174A1/ja not_active Application Discontinuation
- 2002-06-06 US US10/343,749 patent/US6881418B2/en not_active Expired - Fee Related
- 2002-06-06 CN CNA028056965A patent/CN1494378A/zh active Pending
- 2002-06-06 EP EP02738630A patent/EP1393628A4/en not_active Withdrawn
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EP0232737A2 (en) * | 1986-01-16 | 1987-08-19 | Ppg Industries, Inc. | Halophor composition |
JPH0680518A (ja) * | 1991-09-18 | 1994-03-22 | Shinto Paint Co Ltd | 殺菌組成物 |
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WO2000018689A1 (fr) * | 1998-09-28 | 2000-04-06 | Ebara Corporation | Procede et dispositif de desinfection de residus de drainage |
JP2002275008A (ja) * | 2001-03-15 | 2002-09-25 | Shinto Fine Co Ltd | ヒダントイン安定化組成物 |
Non-Patent Citations (1)
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See also references of EP1393628A4 * |
Also Published As
Publication number | Publication date |
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US6881418B2 (en) | 2005-04-19 |
CN1494378A (zh) | 2004-05-05 |
US20030157051A1 (en) | 2003-08-21 |
EP1393628A1 (en) | 2004-03-03 |
EP1393628A4 (en) | 2007-11-14 |
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