WO1989001023A1 - Nettoyage microbicide ou compositions desinfectantes et leur preparation - Google Patents

Nettoyage microbicide ou compositions desinfectantes et leur preparation Download PDF

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Publication number
WO1989001023A1
WO1989001023A1 PCT/US1988/002647 US8802647W WO8901023A1 WO 1989001023 A1 WO1989001023 A1 WO 1989001023A1 US 8802647 W US8802647 W US 8802647W WO 8901023 A1 WO8901023 A1 WO 8901023A1
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Prior art keywords
group
carbon atoms
alkyl group
approximately
microbiocidal
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PCT/US1988/002647
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English (en)
Inventor
Robert H. Mcintosh
Original Assignee
Interface Research Corporation
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Publication date
Application filed by Interface Research Corporation filed Critical Interface Research Corporation
Priority to KR1019890700490A priority Critical patent/KR910005713B1/ko
Publication of WO1989001023A1 publication Critical patent/WO1989001023A1/fr
Priority to DK160589A priority patent/DK160589D0/da

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/362—Phosphates or phosphites

Definitions

  • the present invention relates to microbiocidal compositions and methods for the preparation and use of such compositions.
  • these microbiocidal compositions are effective in killing or inhibiting a wide variety of harmful, destructive, or offensive microorganisms including viruses, bacteria, algae, yeasts, and molds.
  • microorganism means any organism that cannot easily be seen with the naked eye and includes organisms such as bacteria, molds, yeasts, fungi, algae and viruses.
  • Antimicrobial and “microbiocidal” describe the killing of, as well as the inhibition of the growth of, bacteria, yeasts, fungi, algae, and molds.
  • Bacicidal describes the killing or inhibition of the growth of bacteria.
  • Fungicidal describes the killing of, as well as the inhibition of the growth of, fungi, yeasts and molds..
  • viralicidal is used to describe the inactivation of virus particles so that they are unable to infect host cells.
  • plastic includes both thermosetting and thermoplastic materials.
  • plastic materials include, but are not limited to, polyolefins (such as polyethylenes, polypropylenes, polybutylenes) polystyrenes, vinyl phenolics, vinyl acetates, polymeric vinyl chlorides, ureas, melamines, acrylics, polyesters, epoxies and nylons.
  • molded as used in this application is used in its broad sense to include any technique for forming plastic or other materials. Molding is generally, but not always, accomplished with elevated temperature and includes, but is not limited to, forming methods such as potting, extruding, sheeting, calendering, pulltruding, casting, vacuum forming, blow molding, and the like.
  • cleaning agent includes any substance capable of cleaning, emulsifying, or removing unwanted material from a surface.
  • detergent describes any substance or product which is capable of dislodging, removing, or dispersing solid and liquid soils from a surface being cleansed.
  • detergent also includes soaps comprising metal salts of long chain fatty acids.
  • disinfectant includes any liquid that is capable of killing or inhibiting microorganisms.
  • free hydroxyl as used herein means an oxygen that is bonded to a phosphorus in a phosphate group.
  • microorganisms Bacteria, fungi, viruses, algae and other microorganisms are always present in our environment. Such microorganisms are frequently an essential part of ecological systems, industrial processes, and healthy human and animal bodily functions, such as digestion. In other instances, however, the presence of microorganisms is highly undesirable because they may cause illnesses or death of humans and animals, create odors and damage or destroy a wide variety of materials.
  • the species and numbers of microorganisms present vary depending on the general environment, on the nutrients and the moisture available for the growth of the microorganisms, and on humidity and temperature of the local environment. Nutrients for microorganisms abound in the normal environment. Any protein matter such as dried skin, discarded foods, plants, and animal wastes all are excellent nutrient media for many types of potentially harmful microorganisms. Furthermore, many organic synthetic and natural materials like plastic coatings and objects, and wood, paper and natural fibers can serve as nutrients for microorganisms which will degrade those materials. In addition, certain bacteria are capable of remaining viable in a dormant state on floors or on objects for long periods of time until they are deposited in the proper media for growth. Consequently, potentially harmful microorganisms can be transported merely by walking on floors, brushing against walls or furniture or by handling objects.
  • Potentially dangerous microorganisms are spread in health care facilities and elsewhere by a variety of vectors.
  • One of the most common vectors is health care personnel. For example, a nurse or doctor may administer care to one patient and then be called upon to treat a second patient. Even though he or she may carefully wash his or her hands before treating the second patient, potentially dangerous microorganisms may be transferred from the first patient to the second patient. The microorganism can then cause a serious infection in the second patient.
  • bacteria which are classified as procaryotes, can be killed or inhibited by many different types of antibiotics.
  • antibiotics that are effective against procaryotic organisms are usually ineffective against eucaryotic microorganisms, such as fungi and yeasts.
  • Gram-positive and Gram- negative bacteria Even within the family of Bacteriaceae, there are two broad categories of bacteria known as Gram-positive and Gram- negative bacteria. These classifications stem from the ability or non-ability of bacteria to absorb certain vital stains, and the two groups of bacteria generally respond differently to the same microbiocidal agent. A particular agent that may be effective against one group may not be effective against the other group.
  • One conventional method of inhibiting the growth of both eucaryotes and procaryotes or both Gram-negative and Gram- positive bacteria is to combine two or more microbiocidal inhibitors, each designed to inhibit or kill a specific organism or class of organisms.
  • various problems arise when introducing two or more additives into a material such as a detergent.
  • the multiple additive system may alter the physical properties of the detergent into which it is mixed.
  • the multiple components must be tested to insure compatibility and continued microbiocidal effectiveness when combined with the detergent.
  • the relative microbiocidal or microbiostatic strength of each of the components in the multiple system must be determined.
  • microbiocidal additives it is not uncommon for the combination of microbiocidal additives to initially have effective inhibiting or killing properties for both Gram-positive and Gram-negative organisms whereupon, with the passage of time, one or the other of the inhibiting additives will deteriorate and lose its effectiveness while the other inhibiting additive remains effective. In addition, one additive may have an unexpected inhibitory effect on the other additive. In addition, the requirement of adding two or more additives can become prohibitively expensive.
  • microbiocidal additive must be non-toxic to humans and animals around which the additive is used. Such an additive should not cause an allergic reaction and must have no long term detrimental health effects on humans or animals. Finally, such an microbiocidal additive should be compatible with the material with which it is being used and not cause the material to deteriorate or lose its desired properties.
  • the present invention solves the problems described above by providing a composition including a broad spectrum, safe, microbiocidal additive that is effective in killing or inhibiting a wide variety of microorganisms including viruses, bacteria, yeasts, molds and fungi and algae.
  • the microbiocidal additive comprises a phosphate derivative having microbiocidal activity.
  • the microbiocidal phosphate derivative has at least one free hydroxyl group thereon.
  • the present invention solves the above problems by providing a safe cleansing solution containing a microbiocidal additive.
  • the additive can be added to water to provide a microbiocidal agent or can be added to a conventional detergent to provide a microbiocidal cleansing agent.
  • the detergents that can be used in the present invention include, but are not limited to, linear alkyl sulfonates and alkyl benzene sulfonates. These detergents also include, but are not limited to, metal salts of long chain fatty acids.
  • the microbiocidal cleansing agent of the present invention is effective in killing or significantly inhibiting the growth of a wide spectrum of both procaryotic and eucaryotic microorganisms which may reside on surfaces to be cleaned or treated with the microbiocidal detergent.
  • certain alkyl phosphate additives provide unique and unexpected fungicidal, viricidal and bactericidal properties to a conventional detergent.
  • the microbiocidal cleansing agent of the present invention has the capacity to kill or inhibit the growth of many types of bacteria, fungi, viruses, yeasts and other destructive or disease-producing microorganisms which might be on a surface cleaned with the microbiocidal detergent of the present invention.
  • the microbiocidal cleansing agent of the present invention is particularly effective against both Gram-positive bacteria, such as Staphylococcus aureus, and Gram-negative bacteria, such as Pseudomonas aeruginosa.
  • the microbiocidal cleansing agent of the present invention also comprises a method for the preparation of and the incorporation into detergents of the alkyl phosphate additives that give the detergents the ability to kill or significantly reduce bacterial growth, fungal growth and yeast growth on surfaces that are cleaned with the detergent.
  • the microbiocidal cleansing agent of the present invention also inactivates virus particles that may be on the surface that is cleaned with the microbiocidal detergent of the present invention.
  • the concentration of the reactants in the preparation of the alkyl phosphate additive the bactericidal activity of the resulting alkyl phosphate additive can be selected.
  • the alkyl phosphate additive can be prepared so that it is effective primarily against Gram-negative bacteria, against Gram-positive bacteria or both.
  • the microbiocidal additive of the present invention is a phosphate derivative with at least one free hydroxyl group.
  • the phosphate derivative has the following general formula:
  • R and R' may be alkyl, aryl, aralkyl and alkaryl groups including, but not limited to, straight chain, branched chain or cyclic alkyl groups having from 1 to 24 carbon atoms, polyoxyethylene or polyoxypropylene having from 2 to 32 ethylene oxide or propylene oxide units respectively, alkyl phenoxy polyoxyethylene containing 2 to 32 ethylene oxide units, alkyl phenoxy polyoxyethylene containing ethylene oxide units and 1 to 24 carbon atoms in the phenolic alkyl chain, and polyhydroxy compounds, including but not limited to, ethylene glycol, glycerol, or sorbitol, wherein R and R' include at least one free hydroxyl group.
  • X is selected from the group consisting of Group IA metals, Group IIA metals, transition metals, hydrogen, and an organic ion.
  • the positively charged ion is not necessary for microbiocidal activity.
  • microbiocidal additive of the present invention can be added to a wide variety of materials in accordance with the present invention to impart microbiocidal activity to those materials.
  • the microbiocidal additive of the present invention can be added to aqueous solutions of detergents in accordance with the present invention to provide microbiocidal cleansing agents, hi addition, the present invention can be added to water or other solvents to provide an effective disinfectant.
  • Th microbiocidal additive of the present invention is capable of killing the causitive organism of Legionaires' disease, Legionella pneumophilia.
  • the present invention embraces addition of the identified compound to cooling tower water to control the growth of this pathological organism.
  • Another object of the present invention is to provide for the use of microbiocidally effective phosphate derivatives which can be added to an aqueous detergent to impart microbiocidal activity to the detergent.
  • Yet another object of the present invention is to provide for the addition of microbiocidally effective phosphate derivatives to water or other solvents to provide effective disinfectants.
  • Another object of the present invention is to provide for incorporation of microbiocidally effective phosphate derivatives into detergents to provide a cleansing agent with microbiocidal activity against a wide variety of organisms including bacteria, fungi, molds, algae and viruses.
  • Another object of the present invention is to provide for incorporation into products or application onto products of microbiocidally effective phosphate derivatives to preserve the products from degradation by microorganisms.
  • Another object of the present invention is to provide an effective insecticidal phosphate derivatives which can be mixed with an aqueous detergent solution and used to wash an animal or object to kill or repel insects or related organisms.
  • Another object of the present invention is to provide a microbiocidal phosphate derivative.
  • the present invention relates to microbiocidal and insecticidal compositions comprising certain derivatives of phosphates.
  • the phosphate derivatives are capable of killing or inhibiting the growth of a wide variety of microorganisms including fungi, yeasts, viruses, algae and bacteria.
  • the phosphate derivative utilized in accordance with the present invention inhibits the growth of the following representative Gram-negative and Gram-positive bacteria: Sarcina lutea, Staphylococcus species, Pseudomonas aeruginosa, Pseudomonas cepacia, Escherichia coli, Escherichia communior, Bacillus subtilis, Klebsiella species, Salmonella species, Legionella pneumophilia, Enterobacter aerogenes and Streptococcus species.
  • the phosphate derivative also inhibits the growth of the following representative fungi and yeasts: Candida albicans, Trichophyton metagrophytes, Trichophyton rubrum, Trichophyton interdigitale and Aspergillus niger.
  • the phosphate derivative also inactivates Herpes simplex virus.
  • the foregoing microorganisms are representative of those organisms that are responsible for infections in hospitals and other health care facilities.
  • the microbiocidal additive of the present invention can be added to water or other solvents to provide a disinfectant formulation or can be added to a conventional detergent to provide a microbiocidal cleansing agent.
  • the detergents that can be used in the present invention include, but are not limited to, linear alkyl sulfonates and alkyl benzene sulfonates. These detergents also include, but are not limited to, metal salts of long chain fatty acids.
  • microbiocidal cleansing agent is effective in killing or significantly inhibiting the growth of a wide spectrum of both procaryotic and eucaryotic microorganisms which may reside on surfaces to be cleaned or treated with the microbiocidal detergent.
  • certain phosphate derivatives impart fungicidal, algaecidal, viricidal and bactericidal properties to a conventional detergent.
  • the microbiocidal additive of the present invention can be mixed in water at various concentrations and be used as a disinfectant formulation to kill or inhibit microorganisms that may reside on that surface.
  • a solution of the additive of the present invention containing from approximately 500 to 1000 parts per million (PPM) of the phosphate derivative makes an excellent disinfectant formulation for light duty such as mopping and cleaning of hard surfaces such as vinyl walls, floors, counters and table tops.
  • the phosphate derivative can be mixed in with a conventional detergent at a concentration of between approximately 15% and 70% by weight.
  • microbiocidal cleansing agent prepared by the addition of the microbiocidal additive of the present invention to a conventional cleansing agent has the capacity to kill or inhibit the growth of many types of bacteria, fungi, viruses, yeasts and other destructive or disease-producing microorganisms which might be on a surface.
  • a microbiocidal cleansing agent is particularly effective against both Gram-positive bacteria, such as Staphylococcus aureus, and Gram-negative bacteria, such as Pseudomonas aeruginosa.
  • the phosphate derivative can be added to the water in cooling towers or can be included in a coating that is used to coat the surfaces in cooling towers to kill or inhibit the growth of the pathogen that causes Legionaire's disease, Legionella pneumophilia.
  • the phosphate derivative has also been found to be an effective deodorant.
  • the phosphate derivative will no longer exhibit microbiocidal activity. It is believed that, in general, the more hydroxyl groups that are free, the greater the gram negative microbiocidal activity will be exhibited by the phosphate derivative.
  • microbiocidal additive of the present invention can be more specifically defined as a phosphate ester with at least one free hydroxyl group with the following general formula:
  • R and R' may be alkyl, aryl, aralkyl and alkaryl groups including, but not limited to, straight chain, branched chain or cyclic alkyl groups having from 1 to 24 carbon atoms, polyoxyethylene or polyoxypropylene having from 2 to 32 ethylene oxide or propylene oxide units respectively, alkyl phenoxy polyoxyethylene containing 2 to 32 ethylene oxide units, alkyl phenoxy polyoxyethylene containing ethylene oxide units and 1 to 24 carbon atoms in the phenolic alkyl chain, and polyhydroxy compounds, including but not limited to, ethylene glycol, glycerol, or sorbitol, wherein R and R' include at least one free hydroxyl group.
  • R may also be hydrogen, but only if X is a quaternary amine.
  • X is selected from the group consisting of Group IA metals, Group IIA metals, transition metals, hydrogen, and an organic ion.
  • a preferred structure of the phosphate derivative comprises the following formula:
  • R and R * an alkyl group of from 6 to 18 carbon atoms and one group can be H.
  • X is selected from the group consisting of Group IA metals, Group HA metals, transition metals, hydrogen, and an organic ion.
  • the microbiocidal additive defined by this formula is water insoluble or only slightly soluble in water and is especially useful for addition to non-aqueous products such as plastics, fibers and non-aqueous coatings.
  • An aqueous suspension of the phosphates with the alkyl group of greater than 6 carbon atoms in the R position can be prepared by adding a surfactant such as Tween 80 (Sigma Chemical Company, St. Louis, MO) or other suitable nonionic surfactant..
  • An especially preferred structure of the microbiocidal additive of the present invention comprises a phosphate with the following formula: O
  • R and R' an alkyl group of from 1 to 5 carbon atoms and one group can be H.
  • X is selected from the group consisting of Group IA metals, Group IIA metals, transition metals, hydrogen, and an organic ion.
  • microbiocidal additive defined by this formula is water soluble and is especially useful as an additive for a disinfectant or for a detergent.
  • An additional preferred structure of the microbiocidal additive of the present invention has the following formula:
  • X is selected from the group consisting of Group IA metals, Group HA metals, transition metals, hydrogen, and an organic ion.
  • R H or C 2 H 5 ; and X is selected from the group consisting of Group IA metals, Group HA metals, transition metals, hydrogen, and an organic ion.
  • This embodiment of the microbiocidal additive of the present invention is soluble in water.
  • the microbiocidal activity of the product can be improved by substituting for "X" a large organic ion such as a quaternary amine.
  • X a large organic ion such as a quaternary amine.
  • An example of such a compound is a tertiary amine with the following general formula:
  • Ri an alkyl group of from 4 to 18 carbon atoms or a hydroxy alkyl group of from 1 to 18 carbon atoms.
  • the Ri groups are not necessarily identical.
  • R 2 an alkyl group of from 8 to 18 carbon atoms.
  • This especially preferred embodiment can be prepared by partially neutralizing phosphoric acid with between 1 to 2 moles of the tertiary amine. If more tertiary amine is used to neutralize the phosphoric acid, the free hydroxyls on the phosphate group will be e___minated and it is believed that the microbiocidal activity of the compound will be diminished.
  • the type of component to be used as the "X" substituent will depend largely upon the compatibility of the base material for the "X" substituent.
  • the microbiocidal additive of the present invention may be prepared as follows: One mole of phosphorous pentoxide is reacted with between approximately 1 to 3 moles of an alcohol.
  • the alcohol can be an alkyl or an aryl compound.
  • the alkyl alcohol can be straight chained, branched chain or cyclic. It is believed that the important aspect of the phosphate derivative is that the compound have at least one free hydroxyl.
  • the alcohol should be heated to a temperature of between approximately 60° and 120° C depending upon the boiling point of the alcohol used.
  • the phosphorous pentoxide is slowly added to the alcohol while the mixture is vigorously agitated. The reaction is complete two to four hours after the addition of phosphorous pentoxide is completed.
  • the product formed in this reaction is a mixture of mono-ester phosphate and di-ester phosphate.
  • the reaction equation is as follows:
  • R is the alkyl or aryl group depending upon the substituent used.
  • the phosphate derivative is an effective microbiocidal compound and is capable of killing or inhibiting a wide variety of microorganisms including bacteria, yeasts, fungi, algae, molds and viruses.
  • the phosphate can be partially neutralized with a tertiary amine as shown in the following reaction equation:
  • the preferable range for X is between approximately 1 and 1.5 moles with the especially preferable range of approximately 1.3 moles.
  • R a straight chain or a branched chain alkyl group of from 1 to 18 carbon atoms
  • Ri an alkyl group of from 4 to 18 carbon atoms or a hydroxyalkyl group of from 1 to 1 8 carbon atoms .
  • R a straight chain or a branched chain alkyl group of from 8 to 18 carbon atoms .
  • the microbiocidal activity of the phosphate derivative of the present invention is evaluated as follows. Petri dishes are prepared using appropriate nutrient agar as a food source for the microorganism to be tested. The microorganism is seeded into the agar as is well known to one or ordinary skill in the art. A hole 6mm in diameter and 5mm deep is cut into the agar. 0.05 ml. of each of the indicated test compounds is placed in the hole and the inoculated petri dish is incubated for 24 hours at 37°C.
  • the relative susceptibility of the test organisms to the phosphate derivative of the present invention is demonstrated by a clear zone of growth inhibition around the test solution.
  • This zone of inhibition is the result of two processes: (1) the diffusion of the compound and (2) growth of the bacteria.
  • the area of the suppressed microbial growth, the zone of inhibition is determined by the concentration of the phosphate derivative present in the area. Therefore, within the limitations of the test, the area of the inhibition zone is proportional to the relative susceptibility of the microorganisms to the phosphate derivative of the present invention.
  • each plate is examined and the diameters of the complete inhibition zones are noted and measured using either reflected light and a measuring device such as sliding calipers, a ruler, or a template prepared for this purpose and held on the bottom of the plate.
  • the end point measured to the nearest millimeter, is the point at which no visible growth that can be detected with the unaided eye minus the diameter of the test drop or sample.
  • the area of the zone of inhibition is then calculated.
  • the mono-ethyl alkyl phosphate derivative is prepared as follows: One mole of phosphorous pentoxide is reacted with three moles of ethanol at a temperature of 60°C. The phosphorous pentoxide is slowly added to the ethanol while the mixture is vigorously agitated. At the reaction temperature of 60° C the reaction is complete in about two hours. The progress of the reaction is determined by titrating the acid that is produced with a solution of potassium hydroxide. The reaction products include approximately equimolar quantities of the mono-ethyl alkyl phosphate and the di-ethyl alkyl phosphate. The mono-ethyl alkyl phosphate is the more microbiocidally active species.
  • the mono-(2-ethylhexyl) phosphate derivative is prepared as follows. One mole of phosphorous pentoxide is reacted with three moles of 2-ethylhexanol at a temperature of 100°C. The phosphorous pentoxide is slowly added to the ethanol while the mixture is vigorously agitated. At the reaction temperature of 100°C the reaction is complete in about two hours. The progress of the reaction is dete ⁇ nined by titrating the acid that is produced with a solution of potassium hydroxide. The reaction products include approximately equimolar quantities of the mono-(2-ethylhexyl) alkyl phosphate and the di(2-ethylhexyl) alkyl phosphate. The mono-(2-ethylhexyl) alkyl phosphate is the more microbiocidally active species.
  • Petri dishes are prepared using trypticase soy nutrient agar (Baltimore Biological Laboratory, Cockeysville, MD).
  • the microorganisms used in this test are the Gram-positive Staphylococcus aureus and the Gram-negative Pseudomonas aeruginosa.
  • Each microorganism is seeded into the agar as is well known to one of ordinary skill in the art.
  • a hole 6mm in diameter and 5mm deep is cut into the agar.
  • 0.05 ml. of each of the indicated test compounds is placed in the hole, and the inoculated petri dish is incubated for 24 hours at 37°C. After the 24 hour incubation period, the relative susceptibility of the test organisms to the phosphate derivative of the present invention is demonstrated by a clear zone of growth inhibition around the test solution.
  • each plate After the 24 hour incubation period, each plate is examined and the diameters of the complete inhibition zones are noted and measured as described above. Each test is performed at least 6 times. The areas shown in Table A are the average of the 6 separate tests.
  • the reaction product of Example II is partially neutralized with bis(hydroxyethyl) cocoamine. 1.3 moles of bis(hydroxyethyl) cocoamine per mole each of the reaction products from Example I is slowly added to the reaction product from Example I until the pH is between approximately 3.2 and 3.8 in a 75% ethanol solution. This reaction is carried out at a temperature of 100°C. The reaction mixture is vigorously agitated during the reaction.
  • An aqueous mixture of the microbiocidal alkyl phosphate is prepared by mixing the alkyl phosphate derivative from Example II with an aqueous detergent solution. The concentration of alkyl phosphate derivative is .05%.
  • the microbiocidal detergent is heated to 85°C. Cotton fabric is then introduced and remains in the heated solution for 15 minutes. The fabric is then rinsed in water at 40° C, removed, and dried.
  • Example V To produce a microbiocidal alkyl phosphate derivative that can be used with a detergent to make a microbiocidal detergent, the reaction product of Example II is neutralized with bis(hydroxy ethyl) cocoamine. 1.3 moles of bis(hydroxyethyl) cocoamine per mole each of the reaction products from Example I is slowly added to the reaction product from Example II until the pH is between approximately 3.2 and 3.8 in a 75% ethanol solution. This reaction is carried out at a temperature of 100°C. The reaction mixture is vigorously agitated during the reaction.
  • a dry free-flowing mixture comprising the microbiocidal cleansing agent of the present invention is prepared by mixing 0.3 grams of the above alkyl phosphate amine derivative with 138.5 grams of "All" detergent as purchased over the counter. One gram of the cleansing agent mixture is then placed in the center of appropriately inoculated petri dishes and incubated for 24 hours at 37°C. Control plates are also prepared with one gram samples of the detergent without any phosphate derivative. After this period of incubation, each plate is examined and the diameters of the inhibition zones are measured. The results are shown in Table B.
  • the detergent alone exhibits some microbiocidal activity probably because of the presence of sodium hypochlorite which would be washed out of fabrics during the rinsing process.
  • the detergent plus additive demonstrates a significant increase in microbiocidal activity over the detergent alone.
  • microbiocidal capability of an alkyl phosphate amine is demonstrated by the following example. Between 0.5 moles and 3.0 moles of bis (hydroxy ethyl) cocoamine per mole of the reaction products from Example II is slowly added to the reaction products from Example II until the pH of the solution is between approximately 2.5 and 6 in a 75% ethanol solution. This reaction is carried out at a temperature of 100°C. The reaction mixture is vigorously agitated during the reaction. The resulting compounds are tested for microbiocidal activity.
  • Petri dishes are prepared using trypticase soy nutrient agar (Baltimore Biological Laboratory, Cockeysville, MD).
  • the microorganisms used in this test are the Gram-positive Staphylococcus aureus and the Gram-negative Pseudomonas aeruginosa.
  • the microorganisms are seeded into nutrient agar as is well known to one of ordinary skill in the art.
  • a hole 6mm in diameter and 5mm deep is cut into the agar.
  • 0.05 ml. of each of the indicated test compounds is placed in the hole and the inoculated petri dish is incubated for 24 hours at 37°C. After the 24 hour incubation period, the relative susceptibility of the test organisms to the phosphate derivative of the present invention is demonstrated by a clear zone of growth inhibition around the test solution.
  • each plate is examined and the diameters of the complete inhibition zones are noted and measured.
  • sample A which is the reaction product from Example II, has excellent microbiocidal activity against both the Gram positive Staphylococcus aureus and the Gram negative Pseudomonas aeruginosa.
  • the reaction product from Example II retains its microbiocidal activity against both these organisms even when reacted with up to 2 moles of the bis- hydroxyethyl cocoamine. When one mole each of the reaction product from Example II is reacted with more than 2 moles of the cocoamine, the microbiocidal activity is diminished.

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  • Detergent Compositions (AREA)

Abstract

Compositions microbicides et procédés de préparation et d'utilisation de ces compositions. Utilisées de manière appropriée selon la présente invention, ces compositions microbicides tuent ou inhibent efficacement une grande variété de microorganismes nuisibles, destructeurs ou toxiques, y compris des virus, des bactéries, des levures, des algues et des moisissures. Ces compositions microbicides peuvent être utilisées avec des détergents conventionnels pour fournir des agents microbicides de nettoyage. On peut également mélanger ces compositions microbicides avec un liquide de façon à obtenir un désinfectant efficace.
PCT/US1988/002647 1987-08-03 1988-08-03 Nettoyage microbicide ou compositions desinfectantes et leur preparation WO1989001023A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1019890700490A KR910005713B1 (ko) 1987-08-03 1988-08-03 살균성 세척 또는 소독제제 및 그의 제법
DK160589A DK160589D0 (da) 1987-08-03 1989-04-03 Mikrobiocide rengoerings- eller desinficeringspraeparater og fremstilling deraf

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8078787A 1987-08-03 1987-08-03
US080,787 1987-08-03

Publications (1)

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WO1989001023A1 true WO1989001023A1 (fr) 1989-02-09

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PCT/US1988/002647 WO1989001023A1 (fr) 1987-08-03 1988-08-03 Nettoyage microbicide ou compositions desinfectantes et leur preparation

Country Status (6)

Country Link
EP (1) EP0486484A1 (fr)
JP (1) JPH02504401A (fr)
KR (1) KR910005713B1 (fr)
AU (1) AU2426688A (fr)
DK (1) DK160589D0 (fr)
WO (1) WO1989001023A1 (fr)

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EP0371803A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
EP0371542A2 (fr) * 1988-12-01 1990-06-06 Unilever N.V. Composition orale
EP0371802A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
EP0371804A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
WO1995001414A1 (fr) * 1993-07-01 1995-01-12 Allergan, Inc. Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaire
FR2727289A1 (fr) * 1994-11-30 1996-05-31 Derives Resiniques Terpenique Composition desinfectante comprenant au moins un alcool terpenique et au moins un tensio-actif acide bactericide, et utilisation de tels tensio-actifs
EP1389909A1 (fr) * 2001-05-03 2004-02-25 Oligos Etc. Inc. Composes antimicrobiens et leurs procedes de mise en oeuvre
US7868162B2 (en) 1998-12-30 2011-01-11 Lakewood-Amedex, Inc. Antimicrobial and antiviral compounds and methods for their use
US8435960B2 (en) 1998-12-30 2013-05-07 Lakewood-Amedex, Inc. Devices for improved wound management

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Publication number Priority date Publication date Assignee Title
JP2010202817A (ja) * 2009-03-05 2010-09-16 Seiren Co Ltd アレルゲン低減化組成物、及びアレルゲン低減化布帛
CN117794373A (zh) * 2021-08-05 2024-03-29 日华化学株式会社 抗菌/抗病毒剂组合物、抗菌/抗病毒性结构体、及抗菌/抗病毒性结构体的制造方法

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US4272395A (en) * 1978-05-30 1981-06-09 Lever Brothers Company Germicidal compositions
US4235733A (en) * 1978-07-13 1980-11-25 Kao Soap Co., Ltd. Antibacterial soap containing trichlorohydroxy diphenyl ether bactericide and an organic phosphoric ester as a stabilizer therefor
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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5180579A (en) * 1988-12-01 1993-01-19 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Topical composition comprising a mixture of particular di-alkyl or alkenyl phosphate esters and mono-alkyl or alkenyl phosphate esters
EP0371803A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
EP0371804A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
EP0371542A3 (en) * 1988-12-01 1990-09-26 Unilever Nv Oral composition
US5015471A (en) * 1988-12-01 1991-05-14 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Topical composition
US5019373A (en) * 1988-12-01 1991-05-28 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Oral composition
US5078991A (en) * 1988-12-01 1992-01-07 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Topical composition
EP0371802A1 (fr) * 1988-12-01 1990-06-06 Unilever Plc Composition pour application topique
EP0371542A2 (fr) * 1988-12-01 1990-06-06 Unilever N.V. Composition orale
WO1995001414A1 (fr) * 1993-07-01 1995-01-12 Allergan, Inc. Solution de nettoyage de lentilles de contact a base d'esters phosphates d'ammonium quaternaire
WO1996016548A1 (fr) * 1994-11-30 1996-06-06 Action Pin Composition desinfectante ou antiseptique comprenant au moins un alcool terpenique et au moins un tensio-actif acide bactericide, et utilisation d'un tel melange
FR2727289A1 (fr) * 1994-11-30 1996-05-31 Derives Resiniques Terpenique Composition desinfectante comprenant au moins un alcool terpenique et au moins un tensio-actif acide bactericide, et utilisation de tels tensio-actifs
US5763468A (en) * 1994-11-30 1998-06-09 Action Pin Disinfectant or antiseptic composition comprising at least one terpene alcohol and at least one bactericidal acidic surfactant, and use of such a mixture
US8435960B2 (en) 1998-12-30 2013-05-07 Lakewood-Amedex, Inc. Devices for improved wound management
US7176191B2 (en) 1998-12-30 2007-02-13 Oligos Etc. Inc. Antimicrobial compounds and methods for their use
US7868162B2 (en) 1998-12-30 2011-01-11 Lakewood-Amedex, Inc. Antimicrobial and antiviral compounds and methods for their use
EP1389909A4 (fr) * 2001-05-03 2005-03-30 Oligos Etc Inc Composes antimicrobiens et leurs procedes de mise en oeuvre
EP2311466A3 (fr) * 2001-05-03 2012-04-25 Lakewood-Amedex, Inc Composés antimicrobiens et leurs procédés de mise en oeuvre
EP1389909A1 (fr) * 2001-05-03 2004-02-25 Oligos Etc. Inc. Composes antimicrobiens et leurs procedes de mise en oeuvre

Also Published As

Publication number Publication date
KR890701720A (ko) 1989-12-21
EP0486484A1 (fr) 1992-05-27
DK160589A (da) 1989-04-03
KR910005713B1 (ko) 1991-08-02
AU2426688A (en) 1989-03-01
DK160589D0 (da) 1989-04-03
EP0486484A4 (fr) 1991-02-01
JPH02504401A (ja) 1990-12-13

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