WO1994006294A1 - Microbicidal compositions and methods - Google Patents
Microbicidal compositions and methods Download PDFInfo
- Publication number
- WO1994006294A1 WO1994006294A1 PCT/GB1993/001823 GB9301823W WO9406294A1 WO 1994006294 A1 WO1994006294 A1 WO 1994006294A1 GB 9301823 W GB9301823 W GB 9301823W WO 9406294 A1 WO9406294 A1 WO 9406294A1
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- WO
- WIPO (PCT)
- Prior art keywords
- peracid
- aliphatic
- acid
- process according
- composition
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/358—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N37/16—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; 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/10—Preserving with acids; Acid fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/157—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
- C07C407/006—Stabilisation; Use of additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- the present invention concerns microbicidal compositions and methods. More specifically, the present invention concerns microbicidal compositions and methods employing aliphatic peracids as microbicide.
- aliphatic peracids as microbicides is well known in the art. Such solutions have found favour because they offer a microbicidal system which has reduced environmental impact and are completely biodegradable.
- the reduction in numbers of viruses is important in controlling or reducing the spread of disease, especially in areas where there is a risk of cross-infection, for example in hospitals and clinics.
- the peracid In many applications of aliphatic peracids, the peracid is supplied as a relatively concentrated solution, and is diluted just prior to use to a concentration that will give good activity in the chosen application. In many cases, it is convenient to dilute with mains water supplied to the site of use, which, in many parts of the world, can contain significant levels of cations, particularly calcium and magnesium ions, which make the water "hard".
- the presence of hardness ions has been shown in the course of the studies leading to the present invention to reduce the stability and hence the efficacy of aliphatic peracids, and although the effect of the hardness ions can to a certain degree be ameliorated by the inclusion in the formulation of a sequestrant for water hardness, eg EDTA, the benefit is somewhat limited.
- aliphatic peracid compositions intrinsically having improved stability in hard water, in the absence of or in addition to that obtained by the incorporation of a sequestrant.
- the microbicidal activity of aliphatic peracids is believed to derive from the oxidation of chemical components of micro-organisms, and so the peracid is decomposed during such action.
- peracids As such, the activity of solutions containing peracids as the only active component is normally restricted by the stability of the peracid in use.
- the mechanism of action of peracids means that they are very suitable for use in shock treatment regimes wherein the levels of micro ⁇ organism are reduced significantly by periodic dosing.
- the substrate that has been treated with a shock dose of peracid is subject to re- contamination during eg storage or further processing, the numbers of micro ⁇ organisms can rapidly reach similar levels to those prior to the treatment, thus necessitating further treatment. It would therefore be desirable to reduce the frequency of these chemical treatments by providing an aliphatic peracid system which maintains its anti-microbial activity over an extended period. It is an object of certain aspects of the present invention to provide aliphatic peracid solutions having improved activity against viruses.
- compositions comprising an aqueous solution of an aliphatic peracid, the corresponding aliphatic acid, hydrogen peroxide, and optionally one or more other aliphatic acids, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- compositions with improved activity against viruses which comprise an aqueous solution of at least one aliphatic peracid, at least one aliphatic acid and hydrogen peroxide, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- compositions with improved stability when diluted with hard water which comprise an aqueous solution of at least one aliphatic peracid at least one aliphatic acid and hydrogen peroxide, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- compositions with improved residual activity which comprise an aqueous solution of at least one aliphatic peracid, at least one aliphatic acid and hydrogen peroxide, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- a virucidal process in which a virus is contacted with an aqueous solution which comprises at least one aliphatic peracid at least one aliphatic acid and hydroge peroxide, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- a process for producing a dilute aqueous solution of an aliphatic peracid having improved stability in which a concentrate containing an aliphatic peracid, aliphatic acid and hydrogen peroxide is diluted with hard water, characterised in that the mole ratio of aliphatic acid to peracid is greater than 5 : 1.
- a microbicidal process having improved residual activity in which a substrate which may be contaminated by micro-organisms is contacted with an aqueous solution which comprises at least one aliphatic peracid at least one aliphatic acid and hydrogen peroxide, characterised in that the mole ratio of aliphatic acids to peracid is greater than 5 : 1.
- an aqueous solution which comprises at least one aliphatic peracid at least one aliphatic acid and hydrogen peroxide, characterised in that the mole ratio of aliphatic acids to peracid is greater than 5 : 1.
- the aliphatic peracid can be any aliphatic peracid that has a disinfectant effect.
- the aliphatic peracid is selected from the group containing soluble peracids, which may include low molecular weigh aliphatic peroxyacids, for example containing up to 6 carbon atoms, of which especially preferred examples comprise peracetic acid and perpropionic acid.
- Other examples include perbutyric acid, persuccinic acid, perglutaric acid and peradipic acid, particularly mixtures of persuccinic, perglutaric and peradipic acids.
- the peracid may alternatively be selected from hydroxy-peracids, for example percitric or pertartaric acid.
- the peracid is peracetic acid.
- the other aliphatic acids which are optionally included in the compositions according to the present invention are selected from the group containing from 1 to 6 carbon atoms, and are preferably acetic or propionic acid.
- compositions according to the present invention and employed in processes according to the present invention are often solutions comprising an equilibrium mixture of an aliphatic peracid, the corresponding aliphatic acid, hydrogen peroxide, water and, when optional additional aliphatic acids are also present, the corresponding peracid.
- aliphatic peracids comprise greater than about 0.1 by weight of the composition, often from about 0.5% to about 20% by weight and most often from about 1 to about 15% by weight.
- the mole ratio of aliphatic acid to peracid is greater than 5 : 1 .
- the mole ratio is from about 10 : 1 to about 40 : 1 , and some preferred embodiments, the mole ratio is from about 13 : 1 to about 25 : 1 .
- Hydrogen peroxide typically comprises from about 0.5 to 20% by weight o the compositions according to the present invention, often from about 0.75 to about 15%, and most often from about 1 to about 10% by weight.
- compositions according to the present invention will usually have a greater microbicidal activity for a given active oxygen concentration than compositions not according to the present invention.
- compositions according to the present invention often additionally comprise one or more stabilisers to further prolong the storage stability of the peracid.
- stabilisers are well known in the art, and often comprise alkyleneaminopolymethylene phosphonic acids, eg cyclohexyldiaminomethylen phosphonic acid and its salts or hydroxyethylidene diphosphonic acid or salts thereof.
- compositions according to the present invention are mineral acids, especially sulphuric, phosphoric and nitric acid, which are often employed as catalysts to speed the equilibration of the compositions during manufacture, corrosion inhibitors, wetting agents, thickeners, dyes and perfumes.
- Suitable corrosion inhibitors can be selected from the group consisting of alkali metal phosphate salts, especially disodium and dipotassium hydrogenphosphate, triazoles, phosphonates, especially cyclohexyldiaminomethylene phosphonic acid and its salts.
- compositions according to the invention can also be employed separately from the compositions according to the invention by supplying a two pack system in which one solution is a composition according to the present invention and the other is a solution of other components. These two packs can then both be diluted in the same solution to form a further composition, also according to th present invention.
- Such an approach has the advantage that it is possible to include in the diluted composition components with desirable properties that would adversely affect the storage stability of the peracid solution over an extended period, but which do not significantly affect the stability of the peracid over the storage period of the diluted solution, which is often less than that of the non-diluted compositions, or at the concentration in the dilution.
- Wetting agents can be either anionic, cationic, amphoteric or nonionic. Particularly suitable wetting agents are alkaryl sulphonic acids or their salts, and alcohol ethoxylates.
- compositions according to the present invention can conveniently be prepared by mixing an organic acid or anhydride with hydrogen peroxide in aqueous solution, in the presence of any additional components, at a temperature in the region of from 10°C to about 50°C and allowing to reach equilibrium.
- compositions according to the present invention can be employed as anti-viral agents, especially in the field of medical instrument disinfection.
- the compositions are often diluted just prior to use.
- the dilution is chosen to be such that the concentration of peracid can often be up to about 2% by weight, although the concentration is usually from about 0.001 % to about 1 %, preferably from about 0.002% to about 0.75%.
- the dilution is by a factor of from about 10 times to about 10,000 times, more often from about 25 times to about 5,000 times, depending on amongst other factors, the concentration of peracid in the starting composition.
- the temperature employed for use of the composition is often greater than about 10°C, often between about 15°C and 75°C, more often between about 17°C and 35°C. It is particularly preferable that the compositions are employed at ambient temperature, and so it will be recognised that this can vary significantly, although the temperature is often likely to be controlled to a certain extent by the use of, for example, air conditioning.
- the compositions can be employed as virucidal agents on or in a wide range of articles, surfaces or media that are contaminated with viruses, and may also be employed on objects where there is a risk of virus contamination. They are particularly suited to the disinfection of hard surfaces and objects containing metal, especially aluminium, brass, copper and steel. The compositions are also suited to the disinfection of cloth articles, for example medical dressings, and aqueous media.
- compositions can be applied to the article or surface in a large number of ways. For example, they can be sprayed or can be wiped using a suitable distributor, eg a cloth. In many embodiments, however, the compositions are employed as a soak bath in which the article to be disinfected is immersed in the bath, and then rinsed after treatment to remove substantially all of the disinfectant.
- the contact period employed can vary widely depending on the area of application, and the concentration of disinfectant. In many embodiments, the contact period is greater than about 30 seconds. In certain preferred embodiments, the contact period is from about 1 minute to about 60 minutes, although it will be recognised that periods significantly longer than this may be employed in cases where the compositions are employed as a soak bath, for example, up to 24 hours or more.
- the peracid solution is in the form of a relativel concentrated solution which is diluted with water prior to use
- the dilute solution produced is employed within a reasonably short period after dilution because, unless the dilution water has been treated to remove impurities prior to use as a diluent, the impurities present in the water can cause a significant reduction in the peracid concentration, and thus reduce the effectiveness of the solution.
- the impurities which can cause such a decomposition are those which are the cause of water hardness, for example, divalent metal carbonate or bicarbonate salts.
- compositions according to the present invention are diluted with hard water, ie water containing greater than about 75ppm and up to about 1500ppm (expressed as CaCO3) of hardness, the solutions produced have improved stability when compared to similar dilutions of peracid compositions not according to the present invention.
- hard water ie water containing greater than about 75ppm and up to about 1500ppm (expressed as CaCO3) of hardness
- the peracid in solutions diluted just prior to use can be stable for a period of several days depending on the application, sometimes up to 10 days, often up to 6 days and in many instances up to 3 days.
- the peracid solutions prepared just prior to use can have a very wide range of peracid concentrations depending on the application, and the conditions under which they are to be applied.
- the concentration of peracid can often be up to about 2% by weight, although the concentration is usually from about 0.001 % to about 1 %, preferably from about 0.002% to about 0.75%.
- the solution is employed as a shock treatment and is required to have a rapid biocidal effect without any need for residual activity.
- the substrate is subject to re- contamination, for example when the substrate is recycled aqueous process liquors as in the paper industry or in cooling water treatment, it is advantageous if the solution has activity which remains beyond the normal activity period of the peracid alone.
- the recycled process liquors are subject to regular shock treatment, but there are often periods when the shock treatment biocide is less effective and so unless all the micro- organisms have been killed, the microbial numbers can increase. Also in these less effective periods, the disinfectant can often be insufficiently active to control fresh microbial contamination. In these cases, it is often not necessary for the residual activity to be sufficient to have a significant biocidal effect; it is sufficient for the residual activity to be sufficient to prevent or inhibit significant increases in the microbial population, ie to be biostatic.
- the peracid compositions according to the present invention have superior residual microbicidal activity, and also that ⁇ their performance as a shock treatment are improved when compared to similar peracid compositions not according to the present invention.
- concentration of peracid employed in applications as a shock treatment with residual activity can vary widely depending on application and the conditions under which it is employed.
- concentration of peracid is often up to about 2% by weight, although the concentration is usually from about 0.001 % to about 1 %, preferably from about 0.002% to about 0.75%.
- compositions according to the present invention where the improved residual activity is of advantage.
- Examples include the disinfection of sugar beet process liquors, cooling water and other circulating water systems, aqueous pulp and paper process liquors, animal feed and grain.
- the peracid compositions may be dosed manually, but in many embodiments, the dosing is automatically controlled by the use of a metering pump and a suitable control system which can deliver the peracid according to a pre-determined programme.
- the peracid can be dosed in a number of different ways, for example as a liquid or as a spray by using suitable equipment known in the art.
- Another area of application for compositions according to the present invention is in the area of fruit and vegetable disinfection.
- Peracid systems are well known for disinfection in this area, either alone or in a two stage process in combination with a reducing agent which prevents excess peracid from oxidising and discolouring the fruit or vegetable being disinfected.
- the concentration of peracid is often up to about 0.2% by weight, although the concentration is usually from about 0.0001 % to about 0.1 %, preferably from about 0.0005% to about 0.05% by weight.
- Typical reducing agents include alkali metal salts of sulphite, metabisulphite and thiosulphate, ascorbic acid and such like, with the most preferred reducing agent being sodium thiosulphate.
- concentration of reducing agent employed is typically chosen to ensure adequate removal of excess peracid and so the concentration can vary quite widely depending on, for example, the concentration of peracid employed. In many cases, the concentration of reductant solution is in the range of from about 0.5g/l to about 50g/l, preferably from about 1 g/l to about 10g/l.
- peracid compositions according to the present invention give superior disinfection and residual activity compared to peracid compositions not according to the present invention.
- Use of compositions according to the present invention in a two stage process with sodium thiosulphate as reducing agent also surprisingly gives superior fruit and vegetable appearance after storage for up to 5 days, particularly in the case of lettuce disinfection.
- the treatment time for use of compositions according to the present invention in fruit and vegetable disinfection is often from about 1 minute to about 60 minutes, and is most often from about 2 minutes to about 30 minutes.
- the contact time for the reductant is often from about 1 minute to about 30 minutes, most often from about 2 minutes to about 15 minutes.
- the temperature at which the disinfection and any subsequent reduction stage take place can vary over a wide range, but is often ambient temperature, and so is usually likely to range from about 10°C to about 30°C in the United Kingdom, but may differ in other countries.
- Example 1 Preparation of Peracid Composition according to the present invention.
- a stock of Polio 2 virus containing 1.8 x 10** plaque forming units per ml (pfu/ml) was treated in a disinfection suspension test at room temperature (about 20 - 25°C) in the presence of horse serum (10%v/v) with a solution of peracetic acid according to the present invention of formula A below, and also with a solution of peracetic acid not according to the invention of formula B below.
- the two solutions were each diluted to give applied peracetic acid concentrations of 800ppm and 1600ppm.
- Contact times of both 5 and 10 minutes were evaluated. Neutralisation after the contact time was by 1 /10th dilution in 5% w/v sodium thiosulphate solution also containing 0.025 %w/v catalase.
- AA acetic acid
- PAA peracetic acid
- Example 4 Residual Activity of Peracetic Acid
- the residual activity and disinfection performance of the formulations given in Table 4 below were evaluated in a suspension test against a mixed culture of 4 asporogenous bacteria, Escherichia coli. Pseudomonas aeruqinosa, Staphylococcus aureus and Streptococcus faecalis, as an initial inoculum of 1 .3 x 1 ⁇ 6 colony forming units/ml (cfu/ml), and as a rechallenge inoculum of 2.6 x 10 ⁇ cfu/ml after 2 days, and 2.1 x 10 ⁇ cfu/ml after 9 days.
- the conditions employed were a temperature of 20°C, water having 100 - 1 20 ppm hardness as CaCO3, and in the presence of 4 g/l yeast extract.
- the viable cell counts were determined after contact times of 10 minutes, and then at intervals over 14 days by one tenth dilution into a universal neutraliser containing 0.25% w/w catalase to prevent further activity and then by decimal dilutions of the neutraliser with Maximal Recovery Diluent. The dilutions were plated out on Plate Count Agar, incubated for 48 hrs at 37°C, and the plate counts measured. The results are given in Table 4 below. Table 4. Results of Disinfection and Residual Activity Trial
- AA acetic acid
- PA propionic acid
- PAA peracetic acid
- PAA 2.4 1 2.4x10 3 1.9x10 4 2.3x10 9 5.1x10 9 5.1 x10 9 6.9x10 9 + 56ppm AA
- compositions according to the present invention ie those with a mole ratio of aliphatic acid to peracid of greater than 5 : 1 give superior initial disinfection compared to the composition not according to the present invention. This is surprising as the acids alone do not have any significant disinfectancy.
- the good residual activity of compositions according to the present invention is clearly demonstrated by the results for 3 days. These results are 24 hours after a challenge with 2.6 x 10 8 cfu/ml.
- the results for both compositions according to the present invention are extremely low compared to the results for the other compositions.
- a similar pattern of results is demonstrated for the results after 10 and 14 days, showing the consistently better performance of compositions according to the present invention.
- Example 5 Vegetable Disinfection.
- the control had 8.4 x 10 ⁇ colony forming units per cm 8 after 3 days
- 100 ppm peracetic acid solutions were produced by aqueous dilution of peracetic acid formulations according to formulations A (according to the invention) and B (not according to the invention) in Example 2 above.
- a 100 ppm peracetic acid solution was produced by aqueous dilution of a third formulation, D.
- Formulation D (not according to the invention) comprised 15% w/w peracetic acid, 14% w/w hydrogen peroxide and 28% w/w acetic acid, with a mole ratio of acetic acid to peracetic acid of 2.4 : 1 .
- formulation A was the only formulation that gave bacteriostasis.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6507877A JPH08502047A (en) | 1992-09-15 | 1993-08-26 | Bactericidal compositions and methods |
BR9307056A BR9307056A (en) | 1992-09-15 | 1993-08-26 | Virucidal process compositions for the preparation of a diluted aqueous solution of microbiological aliphatic peracid and for the disinfection of fruits and vegetables |
AU49709/93A AU680831B2 (en) | 1992-09-15 | 1993-08-26 | Microbicidal compositions and methods |
EP94910253A EP0660666A1 (en) | 1992-09-15 | 1993-08-26 | Microbicidal compositions and methods |
FI951197A FI951197A (en) | 1992-09-15 | 1995-03-15 | Microbicidal compositions and methods |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9219465.3 | 1992-09-15 | ||
GB929219465A GB9219465D0 (en) | 1992-09-15 | 1992-09-15 | Microbicidal compositions and methods |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994006294A1 true WO1994006294A1 (en) | 1994-03-31 |
Family
ID=10721907
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1993/001823 WO1994006294A1 (en) | 1992-09-15 | 1993-08-26 | Microbicidal compositions and methods |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0660666A1 (en) |
JP (1) | JPH08502047A (en) |
AU (1) | AU680831B2 (en) |
BR (1) | BR9307056A (en) |
CA (1) | CA2144340A1 (en) |
FI (1) | FI951197A (en) |
GB (1) | GB9219465D0 (en) |
WO (1) | WO1994006294A1 (en) |
Cited By (25)
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WO1997042984A1 (en) * | 1996-05-09 | 1997-11-20 | Solvay Interox Limited | Slurry deodorisation |
US6024986A (en) * | 1999-05-24 | 2000-02-15 | Ecolab Inc. | Method of protecting growing plants from the effects of plant pathogens |
US6096348A (en) * | 1996-02-12 | 2000-08-01 | Healthpoint, Ltd. | Quick acting chemical sterilant |
US6165483A (en) * | 1998-04-06 | 2000-12-26 | Ecolab Inc. | Peroxy acid treatment to control pathogenic organisms on growing plants |
WO2000078153A1 (en) * | 1999-06-18 | 2000-12-28 | Tare Shyti Shpetim | Aqueous disinfecting solution |
US6506416B1 (en) | 1999-06-30 | 2003-01-14 | Kao Corporation | Virucide composition and sporicide composition |
US6506417B1 (en) * | 2001-06-28 | 2003-01-14 | Fmc Technologies, Inc. | Composition and process for reducing bacterial citrus canker organisms |
US6627657B1 (en) | 2000-03-22 | 2003-09-30 | Ecolab Inc. | Peroxycarboxylic acid compositions and methods of use against microbial spores |
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EP1378172A1 (en) * | 2002-07-03 | 2004-01-07 | Societe D'exploitation De Produits Pour Les Industries Chimiques, S.E.P.P.I.C. | Method and use of peracetic acid solutions for washing vegetable food products of the fourth category |
WO2004108171A1 (en) * | 2003-06-04 | 2004-12-16 | Klaver Trend, S.A.R.L. | Disinfecting, aqueous and ready-to-use composition of a stabilized complex of peracetic acid, hydrogen peroxide, peroxyacids and acetic acid |
WO2005029959A1 (en) * | 2003-09-18 | 2005-04-07 | Barry Graham Danvers | Preservative for algae product |
EP1550376A1 (en) * | 2003-12-29 | 2005-07-06 | SOLVAY (Société Anonyme) | Process for the disinfection and/or preservation of harvested plant material |
WO2010050634A1 (en) * | 2008-10-30 | 2010-05-06 | Lee, Jin Tae | Manufacturing method for peracetic acid solution using column-type reactor and coil-tube-type aging reactor |
BE1020013A3 (en) * | 2011-07-11 | 2013-03-05 | Christeyns Nv | PRODUCTION OF MORE STABLE PERSONS. |
US8957246B2 (en) | 2006-10-18 | 2015-02-17 | Ecolab USA, Inc. | Method for making a peroxycarboxylic acid |
US8999175B2 (en) | 2004-01-09 | 2015-04-07 | Ecolab Usa Inc. | Methods for washing and processing fruits, vegetables, and other produce with medium chain peroxycarboxylic acid compositions |
US9167814B2 (en) | 2005-07-06 | 2015-10-27 | Ecolab USA, Inc. | Surfactant peroxycarboxylic acid compositions |
US9247738B2 (en) | 2000-07-12 | 2016-02-02 | Ecolab Usa Inc. | Method and composition for inhibition of microbial growth in aqueous food transport and process streams |
US9491965B2 (en) | 2004-01-09 | 2016-11-15 | Ecolab Usa Inc. | Medium chain peroxycarboxylic acid compositions |
US9511161B2 (en) | 2004-01-09 | 2016-12-06 | Ecolab Usa Inc. | Methods for reducing the population of arthropods with medium chain peroxycarboxylic acid compositions |
US9560874B2 (en) | 1998-08-20 | 2017-02-07 | Ecolab Usa Inc. | Treatment of animal carcasses |
US11241658B2 (en) | 2018-02-14 | 2022-02-08 | Ecolab Usa Inc. | Compositions and methods for the reduction of biofilm and spores from membranes |
US11659844B1 (en) | 2016-08-12 | 2023-05-30 | Zee Company I, Llc | System for increasing antimicrobial efficacy in a poultry processing tank |
US11839858B1 (en) | 2016-02-17 | 2023-12-12 | Zee Company I, Llc | Peracetic acid concentration and monitoring and concentration-based dosing system |
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FR2874154B1 (en) * | 2004-08-13 | 2009-05-01 | Moulins Soufflet Sa | PROCESS FOR DECONTAMINATION OF GRAINS |
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Also Published As
Publication number | Publication date |
---|---|
FI951197A0 (en) | 1995-03-15 |
GB9219465D0 (en) | 1992-10-28 |
AU4970993A (en) | 1994-04-12 |
EP0660666A1 (en) | 1995-07-05 |
JPH08502047A (en) | 1996-03-05 |
CA2144340A1 (en) | 1994-03-31 |
BR9307056A (en) | 1999-06-29 |
FI951197A (en) | 1995-03-15 |
AU680831B2 (en) | 1997-08-14 |
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