WO1990006054A1 - Anti-microbial agent - Google Patents

Anti-microbial agent Download PDF

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Publication number
WO1990006054A1
WO1990006054A1 PCT/GB1989/001436 GB8901436W WO9006054A1 WO 1990006054 A1 WO1990006054 A1 WO 1990006054A1 GB 8901436 W GB8901436 W GB 8901436W WO 9006054 A1 WO9006054 A1 WO 9006054A1
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WO
WIPO (PCT)
Prior art keywords
aldehyde
complex
fluid
glutaraldehyde
bacteria
Prior art date
Application number
PCT/GB1989/001436
Other languages
French (fr)
Inventor
Eric Wrench
Original Assignee
National Research Development Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by National Research Development Corporation filed Critical National Research Development Corporation
Priority to MC@@@@D priority Critical patent/MC2140A1/en
Priority to KR1019900701668A priority patent/KR900701160A/en
Priority to BR898907796A priority patent/BR8907796A/en
Priority to IN47/CAL/90A priority patent/IN170040B/en
Publication of WO1990006054A1 publication Critical patent/WO1990006054A1/en
Priority to MW20/91A priority patent/MW2091A1/en
Priority to GB9111655A priority patent/GB2244216B/en
Priority to NO91912109A priority patent/NO912109L/en
Priority to DK911045A priority patent/DK104591D0/en
Priority to FI912644A priority patent/FI912644A0/en

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Classifications

    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/60—Compositions for stimulating production by acting on the underground formation
    • C09K8/605—Compositions for stimulating production by acting on the underground formation containing biocides

Definitions

  • This invention relates to anti-microbial agents and, more particularly, to such agents and their use to control bacteria in such locations as the cooling towers of the air conditioning systems of large buildings, anaerobic fluids in oil wells, and water-based slurries in industrial process plant.
  • 1,5-Pentanedial (commonly known as glutaraldehyde) is known for use as a disinfectant.
  • Proprietary compositions include BASF's PROTECTOL (Trade Mark) and Union Carbide's AQUCAR (trade Mark). Essentially, these products are aqueous solutions of glutaraldehyde. They are used in particular to control growth of bacteria in cooling towers, and the anaerobic bacterium Desulfovibrio desulfuricans in oil well environments.
  • Glutaraldehyde is, however, relatively reactive and so is liable to lose effectiveness unless stored and used in particular ways, As temperature rises above about 30°C or pH above about 7 it is liable to polymerise. In the hot environment of an oil well this loss of effectiveness is a serious problem and expense.
  • a bisulphite addition complex of an aldehyde or di-aldehyde for use as an anti-microbial agent.
  • a method of controlling the growth of bacteria at a particular site by introducing to the site a bisulphite addition complex of an aldehyde or di-aldehyde.
  • the site may be, for example, a body of water in the cooling tower of an air conditioning system of a building.
  • the addition complex may be added as an aqueous solution, so the aldehyde or di-aldehyde complex should be water-soluble. Including a surfactant may assist contact between the complex and the organisms to be combated.
  • the action of the cooling tower brings the water into intimate contact with atmospheric oxygen, which oxidises the complex to release the aldehyde or di-aldehyde which is thereby available in the body of water to disinfect it.
  • the addition complex has proved effective in controlling Legionella pneumophila.
  • the site may instead be within an oil well, where the presence of Desulfovibrio desulfuricans is a problem.
  • Tests conducted by the Applicants have established the effectiveness of the bisulphite complex in combating this bacterium. It may be that Desulfovibrio desulfuricans utilises the sulphite content of the complex as a terminal electron acceptor and, in so doing, liberates the aldehyde or di-aldehyde which is effective then to kill the bacterium. Conventionally, glutaraldehyde is used to control this bacterium.
  • the bisulphite addition complex can be used in slurries of ground calcium carbonate as are used in the paper trade as a filler. These products are frequently contaminated with Desulfovibrio desulfuricans, to become objectionable slurries smelling highly of hydrogen sulphide and similar noxious products. Addition of the complex provides protection from this effect at very low concentrations. It is therefore relatively economic and yet effective over a long period of time, with very little adverse effect on the slurry and its uses compared to the addition of other conventional bactericides.
  • the addition complex is thermally more stable than the uncomplexed aldehyde or di-aldehyde, and less likely to polymerise.
  • the cooling tower oxidation acts as a slow release machanism, of uncomplexed biocide from dissolved complex in the water body.
  • the complex may remain indefinitely, to police bacterial. growth, being consumed only when sulphate reducing bacteria are present and utilising it.
  • it is likely that less of the anti-microbial agent will be consumed, and that its replenishment need take place less frequently. Initial concentrations will tend to be less, and there is much less prospect of po-llution damage if there is a release of the fluid containing the anti-microbial agent.
  • Aldehyde bisulphite complexes were made by the following method.
  • the anti-microbial activity of the bisulphite complex of the aldehydes in Table 1 at 35°C was examined by incubating test tubes, inoculated at zero time with sulphate reducing bacteria, and monitoring the extent of bacterial cell growth with time.
  • the bacterial inoculant was a culture of Desulfovibrio desulfuricans (NCIB 8307) grown and inoculated at 35°C in anaerobic conditions in Postgates medium.
  • the composition of this medium is given below in Table 2.
  • Test tubes were prepared in groups of three. Each control tube contained 20mls of a mixture of Postgates medium and a saline reductant (9g NaCl and 0.1g sodium thioglycollate per litre of distilled water).
  • Each tube exemplifying the invention also contained, in the 20ml charge, one or other of the bisulphite complexes of Table 1, at a concentration of 100, 1000 or 5000mg/litre.
  • the inoculated tubes were examined daily for bacterial growth as evidenced by blackening of the growth medium.
  • the Most Probable Numbers (MPN) method provides a basis for a quantitative assessment of the numbers of sulphate reducing bacteria present at any particular time.
  • MPN Most Probable Numbers
  • Table 3 the results are shown for each test tube monitored, growth being signified by (+) and the absence of growth by (-).
  • the individual anti-microbial agent is identified by the abbreviation used in Table 1, suffixed B when the bisulphite complex was used.
  • a glutaraldehyde complex was compared with straight glutaraldehyde with an without air oxidation using the minimum inhibitory concentration test (MIC) following the German guidelines and recommendations as applied by Kelsey and Sykes. Tests were carried out against Legionella bacteria and Pseudomonas specie using the following media cultures.
  • MIC minimum inhibitory concentration test
  • Mueller-Hinton broth medium absorbs biocidal chemical medium. Any reduction in growth in a bacteriostatic test would indicate an active biocide. Thus, where only small colonies are noted, in a case of a large initial concentration of cells, inhibition of growth is indicated, and thus as active biocide.
  • the Table shows strong inhibition of growth of Streptococcus faecalis by the glutaraldehyde and benzaldehyde bisulphite complex and good, but less strong, inhibition of growth of Escherichia coli.
  • the other anti-microbial agents has an inhibitory effect, but not so pronounced.
  • the bisulphite complex of a low molecular weight aldehyde or di-aldehyde is easier to handle, and less toxic, than the corresponding free aldehyde or di-aldehyde. Its accidental release causes less environmental damage, and it is more thermally stable and resistant to polymerisation. Yet it can be at least as effective as the free aldehyde or di-aldehyde as an anti-microbial agent, in that it will readily release the free aldehyde for biocidal action, for example by oxidation or by the action of the microbe itself on the aldehyde complex. It may therefore be possible to achieve anti-microbial effects comparable with existing glutaraldehyde treatment regimes, but at lower consumption of the anti-microbial agent.
  • the rate of release of the biocide into, for example, a body of water in a cooling tower will generally be over a period of time determined by the rate of oxidation of the bisulphite complex.
  • the rate of oxidation can be controlled by, for example, the vigour and intimacy with which the water is mixed with ambient air.
  • the sodium or potassium addition complex is employed, and normally the aldehyde or di-aldehyde is chosen so as to yield a water-soluble bisulphite addition complex of wide utility, which is cheap to manufacture and easy to use.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Agronomy & Crop Science (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

Glutaraldehyde is a useful anti-microbial agent, but is dangerous and unpleasant to handle and is thermally unstable. Despite these disadvantages, it is specified for use against bacteria in cooling towers of air conditioning plants of buildings and to control anaerobic sulphate-reducing bacteria in oil wells. The invention provides the bisulphite addition complex of an aldehyde or di-aldehyde, for use as an anti-microbial agent. The complex is less toxic than free glutaraldehyde. In cooling towers it slowly oxidises to the free di-aldehyde. In oil wells, its digestion by the sulphate-reducing bacteria releases the free di-aldehyde which controls the bacteria. In these ways, a more economic and environmentally safer use of anti-microbial additives is likely.

Description

ANTI-MICROBIAL AGENT
Technical Field
This invention relates to anti-microbial agents and, more particularly, to such agents and their use to control bacteria in such locations as the cooling towers of the air conditioning systems of large buildings, anaerobic fluids in oil wells, and water-based slurries in industrial process plant.
Background Art
1,5-Pentanedial (commonly known as glutaraldehyde) is known for use as a disinfectant. Proprietary compositions include BASF's PROTECTOL (Trade Mark) and Union Carbide's AQUCAR (trade Mark). Essentially, these products are aqueous solutions of glutaraldehyde. They are used in particular to control growth of bacteria in cooling towers, and the anaerobic bacterium Desulfovibrio desulfuricans in oil well environments.
Glutaraldehyde is, however, relatively reactive and so is liable to lose effectiveness unless stored and used in particular ways, As temperature rises above about 30°C or pH above about 7 it is liable to polymerise. In the hot environment of an oil well this loss of effectiveness is a serious problem and expense.
Uncontrolled release of glutaraldehyde at high concentration is undesirable because it is biologically so harmful. In situations where release of pollutants is strictly controlled, therefore, glutaraldehyde can only be used with extreme care.
It is an object of the present invention to provide the anti-microbial effectiveness of glutaraldehyde more economically and with reduced risk of environmental damage.
Summary of the Invention
According to a first aspect of the invention there is provided a bisulphite addition complex of an aldehyde or di-aldehyde, for use as an anti-microbial agent.
According to a second aspect of the invention there is provided a method of controlling the growth of bacteria at a particular site by introducing to the site a bisulphite addition complex of an aldehyde or di-aldehyde.
The site may be, for example, a body of water in the cooling tower of an air conditioning system of a building. In such a case it may be convenient to add the addition complex as an aqueous solution, so the aldehyde or di-aldehyde complex should be water-soluble. Including a surfactant may assist contact between the complex and the organisms to be combated. The action of the cooling tower brings the water into intimate contact with atmospheric oxygen, which oxidises the complex to release the aldehyde or di-aldehyde which is thereby available in the body of water to disinfect it. As shown below, the addition complex has proved effective in controlling Legionella pneumophila.
The site may instead be within an oil well, where the presence of Desulfovibrio desulfuricans is a problem. Tests conducted by the Applicants have established the effectiveness of the bisulphite complex in combating this bacterium. It may be that Desulfovibrio desulfuricans utilises the sulphite content of the complex as a terminal electron acceptor and, in so doing, liberates the aldehyde or di-aldehyde which is effective then to kill the bacterium. Conventionally, glutaraldehyde is used to control this bacterium. As a di-aldehyde its addition complex has two bisulphite groups, both of which have to be utilised by the bacterium before the uncomplexed aldehyde is released. Effectiveness may depend on the availability to the bacterium of the sulphite in the addition complex relative to that of the sulphite in the oil, which it would utilise in the absence of the addition complex.
In a similar way, the bisulphite addition complex can be used in slurries of ground calcium carbonate as are used in the paper trade as a filler. These products are frequently contaminated with Desulfovibrio desulfuricans, to become objectionable slurries smelling highly of hydrogen sulphide and similar noxious products. Addition of the complex provides protection from this effect at very low concentrations. It is therefore relatively economic and yet effective over a long period of time, with very little adverse effect on the slurry and its uses compared to the addition of other conventional bactericides.
In all these applications, it is valuable that the addition complex is thermally more stable than the uncomplexed aldehyde or di-aldehyde, and less likely to polymerise. The cooling tower oxidation acts as a slow release machanism, of uncomplexed biocide from dissolved complex in the water body. In the oil well situation, the complex may remain indefinitely, to police bacterial. growth, being consumed only when sulphate reducing bacteria are present and utilising it. Thus, it is likely that less of the anti-microbial agent will be consumed, and that its replenishment need take place less frequently. Initial concentrations will tend to be less, and there is much less prospect of po-llution damage if there is a release of the fluid containing the anti-microbial agent.
Description of Preferred Embodiments
Aldehyde bisulphite complexes were made by the following method.
Sodium metabisulphite in the required quantity was dissolved in water and its temperature brought to 40°C. Aldehyde as required was added and the mixture stirred for one hour. Each mixture became homogeneous over the course of the hour and was assumed to have reacted completely. Individual experiments are shown in Table 1 below. Because benzaldehyde is of limited solubility it was reacted at 50°C. After one hour most of the benzaldehyde had reacted.
The invention is illustrated by the following Examples.
EXAMPLE 1
The anti-microbial activity of the bisulphite complex of the aldehydes in Table 1 at 35°C was examined by incubating test tubes, inoculated at zero time with sulphate reducing bacteria, and monitoring the extent of bacterial cell growth with time.
The bacterial inoculant was a culture of Desulfovibrio desulfuricans (NCIB 8307) grown and inoculated at 35°C in anaerobic conditions in Postgates medium. The composition of this medium is given below in Table 2.
Test tubes were prepared in groups of three. Each control tube contained 20mls of a mixture of Postgates medium and a saline reductant (9g NaCl and 0.1g sodium thioglycollate per litre of distilled water).
Each tube exemplifying the invention also contained, in the 20ml charge, one or other of the bisulphite complexes of Table 1, at a concentration of 100, 1000 or 5000mg/litre. The inoculated tubes were examined daily for bacterial growth as evidenced by blackening of the growth medium. The Most Probable Numbers (MPN) method provides a basis for a quantitative assessment of the numbers of sulphate reducing bacteria present at any particular time. In Table 3, the results are shown for each test tube monitored, growth being signified by (+) and the absence of growth by (-). The individual anti-microbial agent is identified by the abbreviation used in Table 1, suffixed B when the bisulphite complex was used.
EXAMPLE 2
The anti-microbial action of the bisulphite complexes of Table 1 against a yeast ( Saccharomyces cerevisiae), a gram positive bacterium (Streptococcus faecalis) and a gram negative bacterium (Escherichia coli) and at a concentration of 5000mg/1 was examined by inoculation into cell cultures in test tubes at time 0, followed by incubation with continuous shaking of the tubes, and estimation of cell numbers after 5hrs and 24hrs. The results are shown in Table 4, expressed as a percentage reduction in the initial concentration of bacteria cells. EXAMPLE 3
A glutaraldehyde complex was compared with straight glutaraldehyde with an without air oxidation using the minimum inhibitory concentration test (MIC) following the German guidelines and recommendations as applied by Kelsey and Sykes. Tests were carried out against Legionella bacteria and Pseudomonas specie using the following media cultures.
1 . Pseudomonas fluorescens - Muellor Hinton Broth
2. Legionella pneumophila - Muellor Hinton Broth with Legionella C7E base and supplement. The dilution tubes were incubated at room temperature for Pseudomonas and 35°C for Legionella pneumophila. All tubes were unshaken. The results of the tests are set out in Table 5 below. Bacterial growth is signified by (+) and absence of growth by (-).
The effect of glutaraldehyde complex on the viability of Pseudomonas fluorescens in water and enrichment broth under conditions of air oxidation was next examined. For the results obtained see Table 6 below, in which the upper half of the table relates to water amd the lower half to enrichment broth. Strong growth, is indicated by (+++), weak growth by (+) and absence of growth by (-).
EXAMPLE 4
Mueller-Hinton broth medium absorbs biocidal chemical medium. Any reduction in growth in a bacteriostatic test would indicate an active biocide. Thus, where only small colonies are noted, in a case of a large initial concentration of cells, inhibition of growth is indicated, and thus as active biocide.
Starter broth cultures grown overnight at 35° were diluted in distilled water. Gram negative (Escherichia coli) and Gram positive (Streptococcus faecalis) test organism cultures were diluted 1:100 and 1:10,000 and plated on to Mueller Hinton medium containing various stated concentrations (mg/1) of specified biocides. The spread plates were incubated at 35°C. The Escherichia coli plates were read after 1 day and the Streptococcus faecalis plates after 3 days. The results are set out below in Table 7. In the Table, the indicia used in earlier Tables have the same meaning. "NN" means "too numerous to count". "W" means "weak growth" and "WW" extremely weak growth.
The Table shows strong inhibition of growth of Streptococcus faecalis by the glutaraldehyde and benzaldehyde bisulphite complex and good, but less strong, inhibition of growth of Escherichia coli. The other anti-microbial agents has an inhibitory effect, but not so pronounced.
INDUSTRIAL APPLICATION
The bisulphite complex of a low molecular weight aldehyde or di-aldehyde is easier to handle, and less toxic, than the corresponding free aldehyde or di-aldehyde. Its accidental release causes less environmental damage, and it is more thermally stable and resistant to polymerisation. Yet it can be at least as effective as the free aldehyde or di-aldehyde as an anti-microbial agent, in that it will readily release the free aldehyde for biocidal action, for example by oxidation or by the action of the microbe itself on the aldehyde complex. It may therefore be possible to achieve anti-microbial effects comparable with existing glutaraldehyde treatment regimes, but at lower consumption of the anti-microbial agent.
The rate of release of the biocide into, for example, a body of water in a cooling tower will generally be over a period of time determined by the rate of oxidation of the bisulphite complex. The rate of oxidation can be controlled by, for example, the vigour and intimacy with which the water is mixed with ambient air. Thus, in aiming for an optimum use of the present bisulphite agents, a more precise specification of cooling tower construction and operation may result.
Normally, the sodium or potassium addition complex is employed, and normally the aldehyde or di-aldehyde is chosen so as to yield a water-soluble bisulphite addition complex of wide utility, which is cheap to manufacture and easy to use.
Figure imgf000010_0001
Figure imgf000012_0001
Figure imgf000013_0001
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Claims

C L A I M S
1. For use as an anti-microbial agent a bisulphite addition compound of an aldehyde or di-aldehyde.
2. An anti-microbial composition, characterised in that it contains, as an active ingredient, a bisulphite addition compound of an aldehyde or di-aldehyde.
3. A composition as claimed in claim 2 wherein the aldehyde or di-aldehyde comprises glutaraldehyde.
4. A composition as claimed in claim 2, wherein the aldehyde or di-aldehyde comprises benzaldehyde.
5. A composition as claimed in claim 2, 3, or 4 characterised by the presence of a surfactant.
6. A method of controlling the growth of bacteria in a body of fluid comprising the step of adding to the fluid a quantity of a bisulphite addition compound of a water-soluble aldehyde or di-aldehyde.
7. A method according to claim 6, wherein the fluid is water contained within a cooling tower of an air conditioning plant.
8. A method according to claim 6, wherein the fluid is a water-based slurry within an industrial manufacturing process.
9. A method according to claim 6, wherein the body of fluid is in an anaerobic environment.
10. A method according to claim 9, wherein the body of fluid is at the bottom of a well.
11. A method according to claim 10, wherein the body of fluid is at the bottom of a well from which a petroleum product is being won.
PCT/GB1989/001436 1988-12-02 1989-12-01 Anti-microbial agent WO1990006054A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
MC@@@@D MC2140A1 (en) 1988-12-02 1989-12-01 ANTIMICROBIAL AGENT
KR1019900701668A KR900701160A (en) 1988-12-02 1989-12-01 Antibacterial agents
BR898907796A BR8907796A (en) 1988-12-02 1989-12-01 ANTI MICROBIAL AGENT
IN47/CAL/90A IN170040B (en) 1988-12-02 1990-01-17
MW20/91A MW2091A1 (en) 1988-12-02 1991-05-28 Anti-microbial agent
GB9111655A GB2244216B (en) 1988-12-02 1991-05-30 Anti-microbial agent
NO91912109A NO912109L (en) 1988-12-02 1991-05-31 ANTI-MICROBIAL AGENT.
DK911045A DK104591D0 (en) 1988-12-02 1991-05-31 ANTIMICROBIAL AGENT
FI912644A FI912644A0 (en) 1988-12-02 1991-05-31 ANTIMICROBISC MEDICINE.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB888828246A GB8828246D0 (en) 1988-12-02 1988-12-02 Method of release of biocides
GB8828246.2 1988-12-02
CN90100430A CN1053727A (en) 1988-12-02 1990-01-31 Antibacterial agent

Publications (1)

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WO1990006054A1 true WO1990006054A1 (en) 1990-06-14

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Country Status (15)

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EP (1) EP0446266A1 (en)
JP (1) JPH04502457A (en)
CN (1) CN1053727A (en)
AU (1) AU4747290A (en)
BR (1) BR8907796A (en)
CA (1) CA2004556A1 (en)
DK (1) DK104591D0 (en)
FI (1) FI912644A0 (en)
GB (2) GB8828246D0 (en)
IN (1) IN170040B (en)
MC (1) MC2140A1 (en)
MW (1) MW2091A1 (en)
NO (1) NO912109L (en)
OA (1) OA09356A (en)
WO (1) WO1990006054A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1561474A1 (en) * 2004-01-30 2005-08-10 Ethicon, Inc. Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds of compositions for disinfection or sterilization
EP2775834A4 (en) * 2011-11-03 2015-10-07 Yoram Tsivion Biologically active compositions containing phenolic residue

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111718693A (en) * 2020-07-01 2020-09-29 秦丹志 Energy conversion liquid

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DE2554587A1 (en) * 1974-12-11 1976-06-16 Arbrook Inc DISINFECTANT
FR2442012A1 (en) * 1978-11-22 1980-06-20 Petteruti Alfredo APPLICATION OF FORMAL ALDEHYDE DERIVATIVES AND THEIR POLYMERS AS FUNGICIDES AND BACTERICIDES IN AGRICULTURE
EP0066759A1 (en) * 1981-05-21 1982-12-15 Union Carbide Corporation Dialdehyde containing compositions
EP0126591A1 (en) * 1983-05-16 1984-11-28 Eli Lilly And Company Dinitroaniline compositions stabilized by incorporation of addition compound of bisulfite and aldehyde or ketone
DE3517548A1 (en) * 1985-05-15 1986-11-20 Schülke & Mayr GmbH, 2000 Norderstedt Solid sporicidal disinfectant, and process for its preparation

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Publication number Priority date Publication date Assignee Title
DE2554587A1 (en) * 1974-12-11 1976-06-16 Arbrook Inc DISINFECTANT
FR2442012A1 (en) * 1978-11-22 1980-06-20 Petteruti Alfredo APPLICATION OF FORMAL ALDEHYDE DERIVATIVES AND THEIR POLYMERS AS FUNGICIDES AND BACTERICIDES IN AGRICULTURE
EP0066759A1 (en) * 1981-05-21 1982-12-15 Union Carbide Corporation Dialdehyde containing compositions
EP0126591A1 (en) * 1983-05-16 1984-11-28 Eli Lilly And Company Dinitroaniline compositions stabilized by incorporation of addition compound of bisulfite and aldehyde or ketone
DE3517548A1 (en) * 1985-05-15 1986-11-20 Schülke & Mayr GmbH, 2000 Norderstedt Solid sporicidal disinfectant, and process for its preparation

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Title
Chemical Abstracts, volume 109, no. 10, 5 September 1988, (Columbus, Ohio, US), see page 419, abstract 79783h, & JP,, 63112532 (Jpn. Kokai Tokkyo Koho Jp) 17 May 1988 *
Chemical Abstracts, volume 110, no. 12, 20 March 1989, (Columbus, Ohio, US), Tashima Toshio et al : "Prevention of precipitation in alkaline aqueous solution of glutaraldehyde for chemosterilization by addition of sulfur oxyacid salts ", see page 424, abstract 101743q, & Bokin Bobai 1988, 16(10), 465- 75. *
The Merck Index, An encyclopedia of chemicals, drugs and biologicals, Eleventh Edition, Susan Budavari, Merck & Co., Inc., Rahway, N.J., USA, 1989, see page 662, No. 4149 and 4150; page 1358, No. 8533 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1561474A1 (en) * 2004-01-30 2005-08-10 Ethicon, Inc. Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds of compositions for disinfection or sterilization
US7476767B2 (en) 2004-01-30 2009-01-13 Ethicon, Inc. Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization
EP2775834A4 (en) * 2011-11-03 2015-10-07 Yoram Tsivion Biologically active compositions containing phenolic residue

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CA2004556A1 (en) 1990-06-02
IN170040B (en) 1992-02-01
JPH04502457A (en) 1992-05-07
MW2091A1 (en) 1993-01-12
GB8828246D0 (en) 1989-01-05
DK104591A (en) 1991-05-31
NO912109D0 (en) 1991-05-31
CN1053727A (en) 1991-08-14
FI912644A0 (en) 1991-05-31
OA09356A (en) 1992-09-15
GB2244216B (en) 1992-09-16
MC2140A1 (en) 1992-02-18
GB2244216A (en) 1991-11-27
NO912109L (en) 1991-05-31
DK104591D0 (en) 1991-05-31
EP0446266A1 (en) 1991-09-18
GB9111655D0 (en) 1991-07-24
BR8907796A (en) 1991-08-27
AU4747290A (en) 1990-06-26

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