WO2000069778A1 - Procedes d'utilisation d'acide percarboxylique ou ses anions et leurs procedes de production - Google Patents

Procedes d'utilisation d'acide percarboxylique ou ses anions et leurs procedes de production Download PDF

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Publication number
WO2000069778A1
WO2000069778A1 PCT/US2000/012711 US0012711W WO0069778A1 WO 2000069778 A1 WO2000069778 A1 WO 2000069778A1 US 0012711 W US0012711 W US 0012711W WO 0069778 A1 WO0069778 A1 WO 0069778A1
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anions
acid
microorganism
peracetyl
ppm
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PCT/US2000/012711
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WO2000069778A9 (fr
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Percy A. Jaquess
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Buckman Laboratories International, Inc.
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Priority to AU49981/00A priority Critical patent/AU4998100A/en
Publication of WO2000069778A1 publication Critical patent/WO2000069778A1/fr
Publication of WO2000069778A9 publication Critical patent/WO2000069778A9/fr

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    • 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
    • C02F1/722—Oxidation by peroxides
    • 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

Definitions

  • the present invention relates to reactions which produce percarboxylic acid and/or anions thereof.
  • the present invention further relates to a variety of methods for using percarboxylic acid and the anions thereof in a variety of applications. Further the present invention relates to controlling the growth of a variety of microorganisms.
  • Bio fouling is a serious economic problem in many commercial and industrial aqueous processes and water handling systems.
  • the fouling is caused by a biomass which is the build up of microorganisms and/or extracellular substances and by dirt or debris that become trapped in the biomass.
  • Bacteria, fungi, yeast, diatoms, and protozoa are only some of the organisms which can cause buildup of a biomass. If not controlled, the biofouling caused by these organisms can interfere with process operations, lower the efficiency of the processes, waste energy, and reduce product quality.
  • Biofilm is the buildup of layers of organisms. Cooling water systems are commonly contaminated with airborne organisms entrained by air/water contact in cooling towers as well as waterborne organisms from the systems makeup water supply. The water in such systems is generally an excellent growth medium for these organisms. If not controlled, the biofilm biofouling resulting from such growth can plug towers, block pipelines, and coat heat transfer surfaces with layers of slime, and thereby prevent proper operation and reduce equipment efficiency.
  • Industrial processes subjected to problems with biofouling include those used for the manufacture of pulp, paper, paperboard, and textiles, particularly water laid non-woven fabrics.
  • paper machines handle very large volumes of water in recirculating systems called '"white water systems.”
  • the white water contains pulp dispersions.
  • the furnish to a paper machine typically contains only about 0.5 % of fibers and non- fiberous paper making solids, which means that for each ton of paper, almost 200 tons of water passes through the paper machine, most of it being recirculated in the white water system.
  • Aqueous systems such as emulsions, suspensions, or solutions containing organic material are also highly subject to microbiological attack.
  • aqueous systems include dyes, latexes, paint, surfactants, dispersants, stabilizers, thickeners, adhesives, starches, waxes, proteins, emulsifying agents, detergents, cellulose products, resins, metalworking fluids, cooling tower fluids, papermill liquids, tanning liquors, and recreational aqueous systems, i.e., pools, spas, and the like.
  • Slime can reduce yields from industrial processes using aqueous systems and render recreational aqueous systems unsuitable for use.
  • Slime consists of matted deposits of microorganisms, fibers, and debris and may be stringy, pasty, rubbery, tapioca-like or hard and may have a characteristic undesirable odor that is different from that of aqueous liquid systems in which it is formed.
  • the microbiological contaminates involved in slime formation are primarily different species of spore-forming and non spore-forming bacteria, particularly capsulated forms of bacteria that secrete gelatinous substances that envelop or encase the cells.
  • Slime microorganisms also include filamentous bacteria, fungi of the mold type, yeast, and yeast-like organisms.
  • the microbiological organisms responsible for biological fouling of various aqueous systems include various bacterial, fungi, mildews, algaes. and the like.
  • various industrial microbiocides are used. Workers in the trade have continued to seek improved biocides that have low toxicity and are capable of exhibiting a prolonged biocidal effect against a wide variety of microorganisms at normal use.
  • stringent environmental and safety regulations as well as escalating development cost have created a need for new microbicidal agents selected from known safe and economical materials.
  • peracetic acid was previously used essentially in the food industries at high concentrations. In the food industries, peracetic acid is used as a sterilant. Until recently, peracetic acid has also been used in combination with other biocides to yield synergistic effects. Peracetic acid has also been an unpopular component in controlling microorganisms especially in industrial water systems due to the significant explosive nature of peracetic acid. At especially high concentrations, peracetic acid can be quite explosive and there have been instances where explosions have occurred. Since peracetic acid is typically transported at high concentrations, users typically introduce high concentrations in their industrial water systems (since trying to dilute peracetic acid can also be a dangerous operation which again can lead to explosions). Thus, those skilled in the art have been quite cautious with the use of peracetic acid as a component in biocides due to this problem.
  • An additional feature of the present invention is to provide a system to generate percarboxylic acid and/or percarboxyl anions which addresses the safety concerns which are present when adding percarboxylic acid directly into an aqueous system.
  • Another feature of the present invention is to provide a variety of applications of the system which generates percarboxylic and/or percarboxyl anions.
  • the present invention relates, in part, to systems which generate percarboxylic acid and/or percarboxyl anions.
  • the percarboxylic acid is preferably a C 2 -C 1 5 percarboxylic acid or mixtures thereof. More preferably, the percarboxylic acid and/or percarboxyl anion is peracetic acid and/or peracetyl anions.
  • Other examples of percarboxylic acid and/or percarboxyl anions include, but are not limited to. peroctanoic, perdecanoic, and the like.
  • the present invention further relates to a method to produce peracetic acid, peracetyl anions, or both by reacting a sulfate containing reactant with tetraacetylethylenediamine in an aqueous solvent and at a sufficient temperature and in sufficient amounts to produce a product comprising peracetic acid and/or peracetyl anions.
  • the present invention further relates to a method to produce percarboxylic acid, percarboxyl anions, or both by reacting a sulfate containing reactant with at least one acid generating acyl activator in an aqueous solvent and at a sufficient temperature and in sufficient amounts to produce a product comprising percarboxylic acid, percarboxyl anions. or both.
  • the present invention relates to a method for controlling the growth of at least one microorganism in an aqueous system involving the step of reacting a sulfate containing reactant with tetraacetylethylenediamine in an aqueous solvent and at a sufficient temperature and in sufficient amounts to produce a product comprising peracetic acid, peracetyl anions, or both and then introducing said product to said aqueous system in an amount effective to control at least one microorganism.
  • the present invention relates to products formed by the above-described processes, including the percarboxylic and/or percarboxyl anions, and preferably the peracetic acid and/or peracetyl anions and any additional products of the reaction. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the present invention as claimed.
  • the present invention relates, in part, to systems which generate percarboxylic acid and/or percarboxyl anions.
  • the percarboxylic acid is preferably a C2-C15 percarboxylic acid or mixtures thereof. More preferably, the percarboxylic acid and or percarboxyl anion is peracetic acid and/or peracetyl anions.
  • Other examples of percarboxylic acid and/or percarboxyl anions include, but are not limited to, peroctanoic, perdecanoic, and the like.
  • a sulfate containing reactant is reacted with an acid generating acyl activator, such as acetylsalicylic acid, diacetyl dioxohexahydrotriazine, tetracetyl glycoluril, tetracetyl methylmethylene diamine, pentacetylglucose. tetraacetylethylenediamine (TAED). and the like.
  • the acid generating acyl activator is TAED.
  • This reaction produces a product preferably containing diacetylethylenediamine (DAED) and peracetic acid and/or peracetyl anions.
  • DAED diacetylethylenediamine
  • sulfate containing compounds or salts thereof include, but are not limited to. sulfolanes. sulfophenyls; sulfoxides; sulfamic acids; sulfanilic acids; and the like.
  • the cation can be any cation and preferably is not explosive.
  • any amount of the reactants can be used so long as there is sufficient amounts to produce percarboxylic acid and/or percarboxyl anions.
  • about 2 moles of the sulfate containing reactant is combined with about 1 mole of the TAED to form about 1 mole of DAED and about 2 mole of peracetic acid and/or peracetyl anions.
  • a hydrogen donating species such as an acid like organic acids or mineral acids can be included in the reaction.
  • the hydrogen donating species acts like a catalyst by increasing the conversion yields of the percarboxylic acid and/or percarboxyl anions and further lowers the pH of the mixture containing the reactants.
  • the amount of the hydrogen donating species is any amount which will lower the pH and/or increase the conversion yield of the products formed from the reaction. Examples of amounts of the hydrogen donating species is from about 5% by weight based on concentration of dry components to about 50% by weight, and more preferably from about 10% to about 30%, and most preferably from about 15% to about 20% by weight.
  • a preferred hydrogen donating species is citric acid.
  • the hydrogen donating species has the ability to control the speed of the reaction.
  • the various reactants are commercially available from numerous sources.
  • the sulfate containing reactant can be obtained from DuPont and the TAED can be obtained from Warwick Chemical, Ltd.
  • the concentration of the sulfate containing reactant is from about
  • the concentration of the TAED is from about 10% to about 40% and more preferably from about 15% to about 25% by weight in solution.
  • the sulfate containing reactant and/or hydrogen donating species have the ability to control the reaction which is advantageous when the reaction is occurring at an end-user site.
  • the reactants can be introduced to an aqueous solvent and preferably agitated.
  • the reaction can occur at any temperature below the boiling point of the reactants to above the freezing point of the reactant.
  • the reaction occurs at ambient temperatures which is quite advantageous for end-user sites.
  • the reaction can occur in a separate system such as in a vessel and then introduced into the aqueous solution to be treated. This is the preferred manner of forming and introducing the products formed from the reactants. However, it is possible to essentially have this reaction occur in situ in the aqueous system to be treated.
  • the reaction is endothermic which is preferred and advantageous for a variety of reasons.
  • Another advantage of the present invention is that the ingredients are preferably solids which can be transported to the end-user site and then added to an aqueous solvent. Further, the system of the present invention preferably kills microorganisms at about 200 ppm or more of the active ingredient and be effective within 10 minutes. Preferred effective concentration ranges include from about 5 ppm to about 3000 ppm or more.
  • an advantage of the present invention is the conversion yields which can be achieved.
  • conversion rates of from about 10% to about 20% are common.
  • a sulfate containing reactant and especially an alkaline persulfate such as potassium persulfate or sodium persulfate
  • conversion yields on the order of from about 70% to 98% are achieved.
  • from about 70% to 98% of the TAED is converted to peracetic acid and/or peracetyl anions. This type of conversion makes the reaction quite economical and effective for end-use applications.
  • the system to generate percarboxylic acid and/or percarboxyl anions can be used in a variety of end-use applications.
  • the conversion yields and the safety considerations provided by this system make it a desirable system to use at end-use applications.
  • this system can be used in any system in need of treatment to control the growth of microorganisms.
  • Aqueous systems which can be treated by the present invention include, but are not limited to, recreational, industrial, and residential aqueous systems.
  • Preferred end-user sites include, but are not limited to, aqueous systems used in the manufacturing of pulp, paper, or paperboard products.
  • the system of the present invention can also be used to treat the aqueous systems used in breweries and other pasteurization systems as well as reverse osmosis systems, holding tanks, cooling towers, swimming pools, hot tubs, Jacuzzis, ponds, and the like.
  • the present invention can also be used with spray washers, water rides, and the like.
  • microbiological control in a water system is very important, since water comes into contact with bottles and cans after they are filled and closed.
  • the system to generate percarboxylic acid and/or percarboxyl anions can be used in such a water system which would be advantageous over current microbicidal systems since the percarboxylic acid and/or percarboxyl anions in the aqueous system would be less corrosive to mild steel and stainless steel unlike the current halogen based treatment programs.
  • much less system maintenance would be needed since less corrosion would occur in such systems when using the present invention.
  • the present invention has advantages over conventional air washer treatment programs including no smell, less corrosive, no sensitizer issues, and its microbicidal effects over a wide spectrum of microorganisms, including pink slime forming species that are difficult to treat.
  • the present invention will have these types of advantages in tobacco plants and textile mills and the like.
  • the present invention will provide air charge control benefits that effect textile operations in spinning and weaving operations.
  • microbiological control in the textile industry has additional concerns.
  • the threads are sprayed with water as they leave the spinnerets and thus the potential for slime forming bacteria problems occur.
  • halogens and quite a few of the non-oxidizers damage the thread strength.
  • the system of the present invention can provide the necessary control of microorganisms and yet not effect the thread strength or other qualities of the synthetic and natural fibers being processed.
  • the present invention's treatment system will provide a less corrosive and more environmental friendly treatment from a discharge permit view point.
  • the treatment system of the present invention will provide a highly effective treatment against these species with the above-identified advantages.
  • microbiological growth in oil storage tanks in particular, in crude and #4, 5, and 6 fuel oils can be a problem.
  • microbiologically induced corrosion problems with down holes for oil production as well as pipeline corrosions are concerns.
  • the system of the present invention can be effective in controlling microorganism growth without corrosion concerns.
  • the system of the present invention will provide an effective means of controlling the growth of microorganisms without the corrosion concerns and odor concerns.
  • the reactants are combined first with or without the optional hydrogen donating species to form the products wherein the reaction occurs in an aqueous solvent, such as water.
  • an aqueous solvent such as water.
  • the solution is introduced into the aqueous system to be treated.
  • the manner in which the products formed from the reaction are introduced can be by any conventional means of introducing a solution into an aqueous system such as, but not limited to. pouring or by metering with a suitable device.
  • biocides such as formaldehyde releasing biocides
  • essentially any other ingredient can be introduced at any time as long as these additional components do not interfere w ith the production of the percarboxylic acid and/or percarboxyl anions.
  • biocides include, but are not limited to.
  • Bronopol 5-Chloro-2-Mehtyl-4-isothiazolin-3-one, 2- Methyl-4-isothiazolin-3-one, Sodium Dichloro-s-triazinetrione, Alkyl*dimethyl benzyl ammonium chloride (*40% C12, 50% C14, 10% C16), Trichloro-s-triazinetrione.
  • biocides e.g., percarboxylic acid/anion and second biocide
  • biocides e.g., percarboxylic acid/anion and second biocide
  • a mixture of 2- (thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate) is used with the peracetic acid, peracetyl anions, or both. This combination is effective in providing a composition that is rapid in response time and yet provides extended control of microorganisms.
  • the present invention accordingly also provides a composition to control the growth of at least one microorganism comprising a) a mixture of 2-(thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate) with b) peracetic acid, peracetyl anions, or both where the components are preferably present in a combined amount effective to control the growth of at least one microorganism.
  • the compositions of the present invention preferably provide superior microbicidal activity at low concentrations against a wide range of microorganisms.
  • the present invention also provides a method for controlling the growth of at least one microorganism in or on a material or medium susceptible to attack by the microorganism which comprises the step of adding to the material or medium a composition of the present invention, where the components of the composition are preferably present in synergistically effective amounts to control the growth of the microorganism.
  • the synergistically effective amount varies in accordance with the material or medium to be treated and can, for a particular application, be routinely determined by one skilled in the art in view of the present invention.
  • the present invention also embodies the separate addition of a mixture of 2- (thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate) with peracetic acid, peracetyl anions, or both to the products, materials, or media described above.
  • the components are individually added to the system so that the final amount of the mixture of 2- (thiocyanomethylthio) benzothiazole and methylene-bis(thiocyanate), and the peracetic acid, peracetyl anions, or both present in the system at the time of use is the amount effective to control the growth of at least one microorganism.
  • 2-(thiocyanomethylthio)benzothiazole is described in U.S. Patent Nos. 3,520,976 and 5,073,638 and the preparation of methylene-bis(thiocyanate) (MTC) is described in U.S. Patent No. 3,524,871, and these disclosures are fully incorporated by reference herein.
  • 2- (thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate) are both commercially available and they are also easily synthesized from commercially available raw materials.
  • MTC is also known as 2-methylene-bis(thiocyanate).
  • the 2-(thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate) mixture is sold in varying concentrations under such commercial names as Busan® 1009, MECT, etc. These commercial products are available from Buckman Laboratories International, Inc. and other distributors.
  • Busan ® 1009 is an emulsifiable concentrate of 10% by weight of 2- (thiocyanomethylthio) benzothiazole and 10% by weight of methylene-bis(thiocyanate).
  • the amounts of the active ingredients in the mixture used as a component in this invention can preferably vary from about 1% to about 80%, preferably from about 1% to about 40%, by weight of 2- (thiocyanomethylthio)benzothiazole and from about 1% to about 80%, preferably 1% to about 40%, by weight of methylene-bis(thiocyanate).
  • the most preferred amounts of these ingredients are those found in Busan® 1009.
  • components (a) and (b) are used preferably in synergistically effective amounts.
  • the weight ratios of (a) to (b) vary depending on the type of microorganisms, products, materials, or media to which the composition is applied. One skilled in the art can readily determine in view of this disclosure, and without undue experimentation, the appropriate weight ratios for a specific application.
  • the ratio of component (a) to component (b) preferably ranges from about 99: 1 to about 1 :99, more preferably from about 1 :30 to about 30: 1 , and most preferably from about 1 :5 to about 5: 1.
  • an effective fungicidal, bactericidal, and/or algicidal response can be obtained when the synergistic combination is employed in concentrations (based on the media to be treated or emulsion used) ranging from about 0.01 to about 5000 ppm of the mixture 2- (thiocyanomethylthio)benzothiazole and methylene-bis(thiocyanate), preferably from about 0.1 to about 1000 ppm, and most preferably from about 0.1 to about 500 ppm; and from about 0.1 ppm to about 5000 ppm of the peracetic acid, peracetyl anions, or both, preferably from about 0.1 to about 500 ppm.
  • the composition may be in the form of a solid, dispersion, emulsion, or solution, depending upon the particular application. Further the components of the composition are preferably applied separately to the product, material, or medium. In lieu of peracetic components as described above, percarboxcylic acid, percarboxyl anions, or both can be used with the biocide(s) in the same manner.
  • an aqueous source is any source containing water or which is water-based or aqueous-based.
  • the production of the products from the reaction will be at a sufficient concentration to control the growth of at least one microorganism. It is understood that by "controlling" the growth of at least one microorganism, the growth of the microorganism is inhibited and/or prevented. In other words, there is no growth or essentially no growth of the microorganism. "Controlling" the growth of at least one microorganism can further include maintaining the microorganism population at a desired level, reducing the population to a desired level (even to undetectable limits, e.g., zero population), and/or inhibits the growth of at least one microorganism.
  • controlling the growth of at least one microorganism can also include biostatically reducing and/or maintaining a low level of microorganism such that the attack by a microorganism and any resulting spoilage or other detrimental are mitigated, i.e., the microorganism growth rate or microorganism attack rate is slowed down or eliminated.
  • microorganisms include, but are not limited to, fungi, bacteria, algae, yeast, spores, and mixtures thereof.
  • the present invention also has the ability to inhibit enzymatic catalase in the same manner that microorganisms can be controlled.
  • the present invention is capable of producing effective amounts of percarboxylic acid and/or percarboxyl anions which are effective in controlling the growth of at least one microorganism
  • the present invention is also directed to methods for controlling the growth of at least one microorganism by reacting the reactants together to form the percarboxylic acid and/or percarboxyl anions which have the ability to control the growth of at least one microorganism.
  • the amount of the percarboxylic acid and/or percarboxyl anions formed from this reaction can be any amount based on the amount of reactants used and the amount of aqueous solvent present during the reaction, however, it is desirable to have a sufficient amount of aqueous solvent as well as reactants to form a solution which contains from about 1 to about 40% (by weight) percarboxylic acid and/or percarboxyl anions and more preferably about 5% (by weight) percarboxylic acid and/or percarboxyl anions by concentration in the aqueous solution.
  • This solution can then be introduced as discussed above to treat the aqueous system.
  • Citric Acid (Anhydrous) 15%-40%, more preferably 17%
  • TAED is supplied as 75% active.
  • K peroxysulfate is supplied as 42.8% active
  • a sample of microbial slime was procured from a paper mill.
  • the inclusive microbial species prefer culture conditions typical of a mill : Temperature 40-50 C, pH 6.5 - 8.0, some available soluble starch. Efficacy assays were run at these preferred conditions in synthetic paper mill water to simulate these conditions. Peracetic acid and peroxide residuals were assayed by chemical strips supplied by EM SCIENCE Industries, located in Gibbstown, NJ. Strips were manufactured in Germany.
  • Peracid Level 10 ppm 50% reduction in microbial population in 1 hour 20 ppm 90 to 98% reduction in microbial population in 1 hour 40 ppm 99% reduction in microbial population in 1 hour 60 ppm 99.8% reduction in microbial population in 1 hour
  • Date Conditions Temp. 40 C, pH ⁇ 7.5 to 7.6, Exposure 1 hour
  • Busan 1009 Level 20 ppm no significant reduction in microbial population 40 ppm 80% reduction in microbial population
  • Reacting Composition is defined as the composition of formulated materials which would generate 1% 3%, and 5% peracetic acid in a process vessel
  • Formulated composition is substantially not reactive until contact with water
  • Example 2 the organism E. cterogenes was introduced into artificial pulp white water having a pH of from about 6.6 to 6.8.
  • the amount of organisms present was 1 X 10 6 organisms per ml of white water.
  • the temperature of the solution was 25° C and the test was run for approximately 3 hours(contact time).
  • a 20% solution of (17% by wt. TAED, 17% by wt. citric acid, and 67% by wt. potassium peroxy sulfate made up in a balance of water to produce a 20% solution) was introduced in the amounts indicated in Table 1.
  • the percentage of organism killed is based on a comparison of the control where no peracetic acid solution was present. As can be seen in Table 1, the peracetic acid made by the present invention was quite effective in controlling this organism. -18-
  • a bacterial alkaline fine paper slime inoculum containing three species was treated with the peracetic acid of the present invention at various temperatures and pHs as indicated in Table 3.
  • the inoculum was approximately 2-3 X 10 /ml of synthetic alkaline white water.
  • the peracetic acid of the present invention was quite effective at various pHs and temperatures with contact times of 1 hour.
  • the peracetic acid of the present invention using methods of the present invention is quite effective in controlling a whole host of microorganisms and inhibiting catalase enzymatic activity.

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  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé de production d'acides percarboxyliques et/ou d'anions percarboxyle, tels que l'acide peracétique et/ou des anions peracétyle, ainsi que l'utilisation de ce système pour traiter ou éliminer la croissance d'au moins un micro-organisme dans des systèmes aqueux tels que les systèmes de production de papier et de pâte, des tours d'eau de refroidissement, des piscines, des jacuzzis, des cuves thermales, des bassins, des brasseries, des systèmes de pasteurisation et analogues. Le système consiste à faire réagir, dans un solvant aqueux, un réactif contenant du sulfate avec un activateur d'acyle générateur d'acide, tel que la tétraacétylènediamine, pour former un produit contenant de l'acide percarboxylique et/ou des anions percarboxyle, tels que l'acide peracétique et/ou des anions peracétyle. L'invention concerne également des procédés de lutte contre au moins un micro-organisme utilisant le système.
PCT/US2000/012711 1999-05-17 2000-05-10 Procedes d'utilisation d'acide percarboxylique ou ses anions et leurs procedes de production WO2000069778A1 (fr)

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AU49981/00A AU4998100A (en) 1999-05-17 2000-05-10 Methods of using percarboxylic acid or anions thereof and methods of making the same

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US60/134,563 1999-05-17
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Cited By (12)

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WO2001070030A2 (fr) * 2000-03-22 2001-09-27 Ecolab Inc. Compositions d'acide peroxycarboxylique et procedes d'utilisations contre des spores microbiennes
US7560033B2 (en) 2004-10-13 2009-07-14 E.I. Dupont De Nemours And Company Multi-functional oxidizing composition
US20120165407A1 (en) * 2010-12-28 2012-06-28 Amit Gupta Strategy for on-site in situ generation of oxidizing compounds and application of the oxidizing compound for microbial control
WO2017100284A1 (fr) * 2015-12-07 2017-06-15 Clean Chemistry, Inc. Procédés de lutte microbienne
US10259729B2 (en) 2014-09-04 2019-04-16 Clean Chemistry, Inc. Systems and method of water treatment utilizing reactive oxygen species and applications thereof
US10472265B2 (en) 2015-03-26 2019-11-12 Clean Chemistry, Inc. Systems and methods of reducing a bacteria population in high hydrogen sulfide water
US10501346B2 (en) 2012-09-07 2019-12-10 Clean Chemistry, Inc. System and method for generation of point of use reactive oxygen species
US10577698B2 (en) 2011-05-31 2020-03-03 Clean Chemistry, Inc. Electrochemical reactor and process
US10883224B2 (en) 2015-12-07 2021-01-05 Clean Chemistry, Inc. Methods of pulp fiber treatment
US11001864B1 (en) 2017-09-07 2021-05-11 Clean Chemistry, Inc. Bacterial control in fermentation systems
US11136714B2 (en) 2016-07-25 2021-10-05 Clean Chemistry, Inc. Methods of optical brightening agent removal
US11311012B1 (en) 2017-09-07 2022-04-26 Clean Chemistry, Inc. Bacterial control in fermentation systems

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