WO1989003179A1 - Compose germicide au dioxyde de chlore - Google Patents

Compose germicide au dioxyde de chlore Download PDF

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Publication number
WO1989003179A1
WO1989003179A1 PCT/US1988/003512 US8803512W WO8903179A1 WO 1989003179 A1 WO1989003179 A1 WO 1989003179A1 US 8803512 W US8803512 W US 8803512W WO 8903179 A1 WO8903179 A1 WO 8903179A1
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Prior art keywords
chlorine dioxide
water
organic solvent
free organic
composition
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Application number
PCT/US1988/003512
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English (en)
Inventor
Lester M. Partlow
François JOOSTE
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New Generation Products, Inc.
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 New Generation Products, Inc. filed Critical New Generation Products, Inc.
Publication of WO1989003179A1 publication Critical patent/WO1989003179A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B11/00—Oxides or oxyacids of halogens; Salts thereof
    • C01B11/02—Oxides of chlorine
    • C01B11/022—Chlorine dioxide (ClO2)
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/40—Peroxides
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • Chlorine dioxide (C10 2 ) is an oxychlorine compound thought to exist almost entirely as a free radical. Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 5, page 612. It has a melting point of -59° Centigrade (C) and a boiling point of 11°C. It exists as a yellow gas at 25°C, which is explosive, and may detonate at pressures greater than 40 kilo pascals (kPa) .
  • Chlorine dioxide is soluble in water, and decomposes slowly even in a neutral aqueous solution in the absence of heat or light. Thus, 1% per week decomposes even when a neutral aqueous solution of 3-5 millimolar C10 2 is kept in a sealed container at a pH 7 in the refrigerator (approximately 4°C) .
  • Granstrom, et al. “Generation and Use of Chlorine Dioxide in Water Treatment," Journal of the American Waterworks
  • CI0 2 preparations e.g., chlorine (Cl 2 ) or hypochlorous acid (HOCl ⁇ a q ⁇ ) are thought to cause C10 2 to oxidize according to the following reactions, which reactions go to completion:
  • chlorine dioxide decomposition is markedly stimulated by light. For example, decomposition of a neutral aqueous solution of chlorine dioxide stored
  • chlorine dioxide has many useful applications. Its disinfecting capabilities have been known since the beginning of the twentieth century, and it has been used to disinfect swimming pool and drinking water since the 1950's.
  • chlorine dioxide has been used as a sterilizer for medical and dental equipment, Tsuchikura, Mitsuru, "Stabilized chlorine dioxide as medical and dental equipment sterilizer," Chemical Abstracts, No. 147203n, Vol. 103, 1985; as a fungicide, Tsuchikura, Mitsuru, "Stabilized chlorine dioxide as fungicide and drinking water disinfectant," Chemical Abstracts, No.
  • This invention comprises chlorine dioxide germicidal compositions, methods for using chlorine dioxide in general and the germicidal compositions in particular, and a method of storing chlorine dioxide.
  • One chlorine dioxide germicidal composition of the present invention comprises an aqueous-organic solution and chlorine dioxide dissolved in said aqueous- organic solution.
  • the aqueous organic solution consists essentially of an organic solvent (e.g. absolute alcohol) , water and C10 . It may be derived by diluting a non- aqueous concentrate with water to a desired concentration.
  • Another germicidal composition of the present invention consists essentially of a germicidally effective I
  • Preferred water-free organic solvents include absolute alcohol, carbon tetrachloride, or isopropanol, which do not react C10 2 or catalyze the 5 decomposition of C10 2 and are germicidal in their own right.
  • Constant concentration of chlorine dioxide designates the amount of free (i.e. available) chlorine dioxide present in solution, as distinguished from the
  • stabilized chlorine dioxide e.g. C10 2 ⁇
  • Free chlorine dioxide will be present in solution in amounts varying
  • a method of storing high concentrations of chlorine dioxide comprising dissolving chlorine dioxide into a water-free organic solvent to form a storage solution of C10 2 .
  • the chlorine dioxide for storage can be
  • the chlorine dioxide gas may be passed through a desiccator (e.g. a column packed with a desiccant or desiccating agent)
  • Water-free solvents useful in the invention include absolute alcohol, propylene glycol, polyethylene glycol, mineral oil, tween-80, surfactants, and emulsifiers. These water-free solvents, and others within
  • the water-free organic solvent and resultant storage solution of C10 2 is preferably soluble in, miscible with, or emulsifiable in water. Such water- free solvents can then be more readily incorporated for use in the aforementioned water-containing germicidal composition.
  • the resultant storage solution of C10 2 should be stored in containers made of materials compatible with the components of the storage solution. Preferably, the storage solution is stored in a light- and air-tight container to minimize decomposition of the C10 2 . Also, preferably no gas is allowed to exist in the storage container (i.e. the storage container is "topped off" with the storage solution.) Lack of a nongaseous phase is also preferred even after use of a portion of the storage container's contents.
  • chlorine dioxide is synthesized as either a liquid or a gas. If it is synthesized as a liquid, it may be converted into a gas in conventional fashion. In any event, chlorine dioxide gas is dissolved for storage in a water-free organic solvent. In most cases, adequate dissolution can be effected by simply permitting the gas to bubble through the solvent, although alternative techniques could be utilized.
  • the solvent should contain no constituent (e.g. water) which disassociates into hydroxyl (OH ⁇ ) or other basic groups.
  • Absolute alcohol is a preferred water-free organic solvent, although generally any organic solvent of C10 2 (i.e. any organic solvent in which C10 2 dissolves) might be used which is soluble in or miscible with water (e.g. propylene glycol) or can be suspended in water via action or a detergent or other emulsifier (e.g., mineral oil) and is nonreactive with C10 2 . If necessary, a chlorine scrubber and a desiccator are placed between the chlorine dioxide generator and the water-free solvent to remove any water and Cl 2 present before dissolution into the organic solvent.
  • the procedures of this invention produce a concentrated solution of chlorine dioxide in a water-free organic solvent. Although higher concentrations are achievable, for most purposes currently within contemplation, concentrations of less than about 5% by weight chlorine dioxide are preferred. In the absence of heat, light, or oxygen, a solution in this form can be stored indefinitely. Shortly before use, the concentrated organic solution may be -diluted with water (H 2 0) to attain a desired use concentration of chlorine dioxide in aqueous solution as described in the first C10 2 composition. Alternatively, the concentrated organic solutions can be diluted to the final working concentration in either the same organic liquid initially used to capture the C10 2 or in another organic liquid.
  • the diluted aqueous or organic solutions prepared in accordance with this invention may be applied to a surface which is to be disinfected or sanitized.
  • the diluted solution is left in contact with the surface for a period of time sufficient to permit disinfection to take place. Typical contact times range from about one second to about five minutes, depending upon the strength of the solution, the nature of the surface to be treated, and the resistance of the specific microorganisms on the surface.
  • the germicidal compositions of the present invention comprise chlorine dioxide dissolved in one or more solvents. Chlorine dioxide is present in said compositions at concentrations sufficient to destroy microorganisms (a "germicidally effective concentration") .
  • concentrations sufficient to destroy microorganisms
  • the total concentration of the chlorine dioxide should be sufficiently low so as not to damage the living tissue of the user significantly (e.g. less than 1000 ppm of C10 in an aqueous, mixed aqueo.us-organic or organic solution) .
  • the composition is used as a disinfectant, i.e. used to destroy microorganisms on an inanimate surface, no such concentration limitation need be adhered to.
  • a typical germicidal composition of the present invention comprises chlorine dioxide dissolved in either an aqueous (i.e. water-containing) or an organic solution such as absolute alcohol.
  • an aqueous i.e. water-containing
  • an organic solution such as absolute alcohol.
  • concentration of C10 2 can be as high as 20,000 ppm.
  • the germicidal composition will typically be made by 1) generating chlorine dioxide gas; 2) passing the generated gas through a chlorine scrubber to remove any free chlorine (Cl 2 ) ; 3) passing the resulting gas through a desiccator to remove water; 4) bubbling the resulting gas through a water-free organic solvent; and 5a) at or near the time of use, diluting the resulting C10 2 water- free organic solvent with an aqueous solution, or 5b) diluting the C10 2 concentrate with the same or a different organic liquid, either at the time of manufacture or at or near the time of use.
  • chlorine dioxide is preferably passed, as a gas, through a chlorine (Cl ) scrubber.
  • Chlorine scrubbers are well known in the art and include passing the generated gas through a column containing either arsenite or solid sodium chlorite or a concentrated sodium chlorite solution. The column or solution absorbs the Cl 2 while allowing the C10 2 to pass unaltered.
  • Industrial methods for purifying chlorine dioxide are described in Masschelein, supra, on pages 135-138, the contents of which are hereby incorporated by reference. Removing chlorine (Cl 2 ) is desirable since Cl 2 tends to increase the rate of oxidation, and thus deactivation, of the chlorine dioxide.
  • the C10 2 gas After passing through the chlorine scrubber, the C10 2 gas is then preferably passed through a desiccator in order to remove any water vapor present. Desiccants which do not react with C10 2 are preferred.
  • the C10 2 gas after being passed through the scrubber and the desiccator, is then bubbled through a water-free, organic solvent.
  • the organic solvent is water free because the presence of water in solution may deactivate the C10 2 , making it unavailable for use as a germicide. Water disassociates into hydride (H + ) and hydroxyl (0H ⁇ ) groups, and hydroxyl ion can stimulate the decomposition of chlorine dioxide and thus inactivate its germicidal effects.
  • Water-free organic solvents useful in the present invention 1) are soluble in, miscible, with or emulsifiable in water, 2) do not react with or encourage the inactivation of C10 2 (e.g. contain no basic groups, amines, alkenes, alkyne bonds or other reactive groups) , and 3) are generally non toxic when applied topically to an animal.
  • C10 2 e.g. contain no basic groups, amines, alkenes, alkyne bonds or other reactive groups
  • Other considerations when selecting a water- free organic solvent ' for use in the invention, especially in considering use as an antiseptic include possible toxicity to sites other than the skin, mutagenicity, carcinogenicity, teratogenicity, and the presence or absence of undesirable odors.
  • Typical solvents are water- free alcohols, containing from one to four carbon atoms, glycerol, polyethylene glycol, propylene glycol, biocompatible emulsifying agents or other surfactants, and non-toxic alkenes such as mineral oil.
  • An ideal water-free organic solvent is absolute alcohol. This substance is greater than 99% ethyl alcohol, contains little or no water, is readily available and is relatively non-toxic to humans. Concentrations of greater than 5% chlorine dioxide by weight dissolved in absolute alcohol should generally be avoided, however, as these mixtures are potentially explosive. If used, the bubbling step for introducing C10 2 gas into the chosen solvent should be accomplished in the presence of an inert gas such as nitrogen as a diluent to avoid explosions and may prevent undesired deactivation of the chlorine dioxide by the presence of oxygen or air. Once dissolved in the water-free organic solvent, the resulting solution can be stored and transported safely. The C10 2 does not degrade appreciably. Greater than 99% of the C10 2 is free and available for use in absolute alcohol. If the chlorine dioxide was produced by one of the "cleaner" techniques, e.g. the Oxidation of Chlorite -li ⁇
  • the solution can be diluted with a predetermined quantity of an aqueous solution to form an "aqueous organic solution.”
  • the aqueous-organic solution can be compounded to attain any concentration of C10 2 desired for the particular germicidal composition.
  • Techniques for determining the amount of aqueous solution needed for a particular concentration of chlorine dioxide in the aqueous-organic solution are straight forward concentration calculations known to anyone skilled in the art. For aqueous solutions, this step will take place at the time of usage or when the germicidal composition is incorporated into a dosage form. For organic solutions, dilution to the final working concentration may occur either during manufacture and prior to packaging, or at the site of application.
  • the aqueous solution used to dilute the C10 2 - organic solvent mix will generally contain water with or without buffering agents.
  • the buffering agents will generally be used to maintain the pH between 2.0 and 7.0, although most pH values will work. Amine compounds and compounds which disassociate into amines, many compounds possessing double (alkenes) or triple (alkynes) carbon- carbon bonds, phenol-like compounds, chlorine, oxychlorine compounds other than C10 2 and other similar components are to be avoided because these substances tend to either react with or increase the deactivation rate of chlorine dioxide. Methods for choosing buffering systems are disclosed in Chase, et al. Remington's Pharmaceutical Sciences. Mack Printing Co., Easton, Pennsylvania, 16th ed. 1980, pages 238-240, the contents of which are hereby incorporated by reference. Typical buffering agents include borates and phosphates.
  • the resulting mixtures should be kept free from ultraviolet or other light, oxygen (0 2 ) and air. Preferably, the mixture is kept cool until use.
  • the germicidal composition can be incorporated into several pharmaceutical dosage forms.
  • These pharmaceutical dosage forms include aerosol containers, various foams, douches, enemas, saline rinses or washes, creams, gels, soaps, lotions, etc.
  • the solution itself can be used to disinfect or sterilize inanimate items which come into contact with blood, such as razors, medical and dental tools, blood bank equipment, etc.
  • Another use is as a general purpose sanitizer for toilet seats and bathrooms. Water, oil-water, alcohol- water, or entirely organic aerosols can be all be used as carriers for C10 2 solutions.
  • the C10 2 -containing organic solvent may be kept separate from the aqueous solution until the composition is to be used. Such a separation can be accomplished by using a pharmaceutical dosage form which maintains the separateness of the two solutions, but which combine the solutions at the time of use.
  • the C10 2 containing organic solvent can be kept in a separate container from the aqueous solution with which it is to be diluted. When the composition is to be used, the two separate solutions can then be combined for use. If the diluted solution is to be stored after mixing, it should be kept away from heat and light.
  • the diluted solutions of this invention can also be incorporated into an aerosol container.
  • Aerosols are well known to those skilled in the art. Typical aerosol dosage forms are described in Remington's, supra, chapter 92, pages 1614-1618, the contents of which are hereby incorporated by reference.
  • the aerosol dosage form is ideal, as the chlorine dioxide composition is kept free from light and air, both of which may increase the rate of breakdown of the chlorine dioxide into germicidally inactive compounds.
  • chlorine dioxide destroys most pathogens including HTLV-III virus (the putative cause of AIDS) , Herpes simplex I and II, Newcastle disease virus, phage OX-174, Sendai virus, Vaccinia virus, Poliovirus A, B, and C, Rotavirus, Echovirus, Coxsackieviruses A9 and B5, bacteriophage f2, Yersinia enterocolitica, Klebsiella pneumoniae, Escherichia coli ATCC No. 1129, three species of Salmonella.
  • pathogens including HTLV-III virus (the putative cause of AIDS) , Herpes simplex I and II, Newcastle disease virus, phage OX-174, Sendai virus, Vaccinia virus, Poliovirus A, B, and C, Rotavirus, Echovirus, Coxsackieviruses A9 and B5, bacteriophage f2, Yersinia enterocolitica, Klebsiella pneumoniae, Escherichia coli
  • Staphylococcus aureus Legionella pneumophila, Pseudomonas species, Listeria monocytogenes, both the bacteria and spores of four Bacillus species, wild type Actinomyces. Niphargus larvae, Arsellus aquaticus larvae, various alga (Scenede us, volvox, synedra, and sphaerotilus) , Nisseria gonorrhoeae. Treponema pallidum, Candida albicans, Trichomonas vaginalis, Lvmphogranuloma venerum chlamydia, and Cytomegalovirus. As little as 1 ppm of chlorine dioxide in solution will destroy 99,999 of 100,000 E .
  • germicidally effective concentrations of C10 2 are typically greater than about 2 ppm. Once made, the composition is easily used. The surface to be sanitized (either an inanimate object or living tissue) is contacted with the composition. Although destruction of many pathogens occurs at strengths as low as 0.75 ppm, the contact time required at such a low concentration to kill some pathogens may be longer than desirable.
  • the concentration of free chlorine dioxide in the germicidal composition varies from about 2 ppm to about 20,000 ppm. Concentrations of less than 1,000 ppm are considered desirable for antiseptic applications.
  • the composition is then allowed to remain in contact with the surface being treated for a sufficient amount of time to allow the chlorine dioxide to destroy any susceptible micro-organisms present. Contact times vary from about one second to about five minutes, depending on the organism to be destroyed, the concentration of chlorine dioxide in the solution, degree of dilution due to presence of fluids on th surface, degree of efficacy necessary, and the surface area of the surface to be treated.
  • the composition can be washed away after the germicidal or other desired activity has taken place.
  • germicidal compositions range from inanimate objects, such as operating tables, to living tissues such as damaged or infected skin or body cavities or tissues, including the nose, mouth, vagina, rectum, eye and ear.
  • Surface disinfection of patient's skin and/or doctor's hands could be accomplished with the same germicidal composition.
  • a longer contact time or a higher concentration may be needed for treating a body cavity, such as the vagina, due to either rugae, or the presence of material which might react with or dilute the C10 2 , such as semen or saliva, which would lower the available concentration of C10 2 and prolong the contact time needed for C10 2 's biocidal effect.
  • an aqueous solution of chlorine dioxide in general, or of one of the specific compositions herein described is for the treatment of gastrointestinal infections.
  • a dry pharmaceutical dosage form which will generate C10 2 in the gastrointestinal tract might be used for destroying such pathogens.
  • An appropriate dry dosage form might comprise 1) sodium chlorite powders or crystals; and 2) an inert material in admixture with the sodium chlorite. The admixture of sodium chlorite and inert material will generate C10 2 in an acidic aqueous solution.
  • the aqueous solution can already be acidic, can be made acidic by the separate addition of an acidifying agent (e.g.
  • stomach acid or can be made acidic by the incorporation of a dry water soluble acidifying agent into the pharmaceutical dosage form.
  • Typical dosage forms would include tablets, capsules, and pills. Methods for making tablets, capsules, and pills, and their respective ingredients are disclosed in Remington' s, supra, chapter 89, pages 1553-1593, the contents of which are hereby incorporated by reference.
  • Typical inert materials would be diluents, binders, lubricants, disintegrators, coloring agents, and flavoring agents, all of which are well known to those skilled in the art.
  • a typical pharmaceutical dosage form for use in destroying pathogens of the gastrointestinal tract includes:
  • the dosage form would be a tablet which was "dry granulated," i.e. enough ingredients for 10,000 tablets would be mixed thoroughly, compressed into slugs, ground and screened into 14-16 mesh granules, and recompressed into tablets using a 1/4-inch concave punch.
  • Typical acidifying agents which could be included into the dosage form would be powders which when dissolved into the aqueous solution would be sufficiently strong enough to react with the NaC10 2 to form C10 2 (e.g. powdered citric acid) .
  • the previously described tablets are taken orally by a user with a predetermined quantity of water (e.g. 500 ml. for the described tablet) to form a germicidally effective concentration of C10 2 to destroy pathogens in the gastrointestinal tract, such as the causative pathogens of cholera, gastric enteritis, and amoebic dysentery.
  • the user's stomach acid would be sufficient to acidify the sodium chlorite solution to generate the C10 2 .
  • an acidifying agent may be incorporated into the dosage form.
  • a liquid solution of C10 2 in general, the specific compositions described herein, or a dry preparation might be used to stabilize blood clots, a problem of real significance on moist tissue such as is encountered in body cavities such as the (1) gastrointestinal tract (from mouth to rectum inclusively) , (2) the urogenital tissues, (3) in the nose, ears and eyes, (4) in surgically exposed body cavities or tissues, and (5) at other sites where blood clot stabilization would be advantageous.
  • body cavities such as the (1) gastrointestinal tract (from mouth to rectum inclusively)
  • the urogenital tissues (3) in the nose, ears and eyes
  • (4) in surgically exposed body cavities or tissues and (5) at other sites where blood clot stabilization would be advantageous.
  • healing of wounds, surgical scars, ulcers, tears and fissures might all be speeded.
  • compositions containing C10 2 such as those described hereinabove could be mixed with saline or other solutions used for lavage of body cavities, tissues, orifices, wounds, or surgical sites to disinfect, reduce tissue swelling, and/or stabilize blood clots.
  • liquids containing C10 2 in general, the specific compositions described herein, and/or dry preparations could be used as an antihistamine and/or anti autacoid preparation.
  • Chlorine dioxide reacts with amines so that both the C10 2 and the amine are altered.
  • Applying C10 2 incorporated into one or more of the aforementioned compositions to an area of skin irritated due to the presence of histamine (e.g. a rash) causes the irritation to subside sooner than when no treatment is given, due to the deactivation of histamine and at least some autacoids.
  • Autacoids likely to be inactivated by the C10 2 compositions include histamine, serotonin, prosta glandins, prostacyclin, thromboxane, angiotensins, plasma kinins (kallidin and bradykinin) and other autacoids yet to be discovered which have similar chemical reactivity.
  • Concentrations of C10 used in formulating a topical antihistamine or anti-autacoid compositions might vary from about 15 to about 100 ppm, but could contain as much as several thousand ppm.
  • C10 2 to inactivate histamine, bradykinin, and prostaglandin-like compounds may be used advantageously in a topical analgesic composition. Histamine, bradykinin, and the prostaglandin-like compounds are thought to serve as pain-carrying chemical messengers in the human body. The C10 2 deactivates these pain-carrying compounds, thereby decreasing the user's sensation of pain.
  • the aforementioned anti-autacoid compositions are useful for the topical analgesic composition.
  • the solvents used in the composition preferably carry the C10 2 through the surface to which the composition is applied to the location of the autacoid molecules. However, even C10 2 dissolved in just water may be useful in this topical analgesic composition.
  • the composition can be used as a free radical scavenger.
  • Chlorine dioxide being a free radical, reacts with other free radicals to deactivate them.
  • Chlorine dioxide dissolved in a water-free organic solvent can then be diluted with another solution, such as normal saline, and the resulting solution may be used as a free radical scavenger.
  • Concentrations of C10 2 used in formulating such a free radical scavenging solution vary from about 15 to about 100 ppm.

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Abstract

On stabilise et on stocke du dioxyde de chlore dans un solvant organique exempt d'eau dans des concentrations de préférence inférieures à environ 5 % en poids. Le dioxyde de chlore est stable dans le solvant organique exempt d'eau et ne se dégrade sensiblementpas. Une fois sous forme de composé, on peut diluer la solution avec une solution aqueuse et l'utiliser comme composé germicide ou composés antihistaminiques topiques. Sont également décrits des procédés de fabrication et d'utilisation du composé.
PCT/US1988/003512 1987-10-13 1988-10-11 Compose germicide au dioxyde de chlore WO1989003179A1 (fr)

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US10813187A 1987-10-13 1987-10-13
US108,131 1987-10-13

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Cited By (18)

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EP0519152A1 (fr) * 1991-06-17 1992-12-23 Rio Linda Chemical Co., Inc. Production de dioxyde de chlore dans un milieu non-aqueux
EP0561145A1 (fr) * 1992-03-19 1993-09-22 Oxo Chemie Ag Utilisation d'une matrice faite à base de chlorite pour la manufacture de préparations médicinales pour le traitement d'infections causées par le HIV
WO1995027472A1 (fr) * 1994-04-07 1995-10-19 Richter Jon L Solution pour bains de bouche et procede de traitement de la bromopnee
WO1996002264A2 (fr) * 1994-07-20 1996-02-01 Allergan, Compositions contenant du dioxyde de chlore a utilisation ophtalmique
EP0748161A1 (fr) * 1994-03-04 1996-12-18 Alcide Corporation Desinfection et reparation de lesions
WO1997008954A1 (fr) * 1995-09-08 1997-03-13 Alcide Corporation Compositions et procedes pour la prevention et le traitement des maladies associees aux abeilles domestiques
US5707546A (en) * 1991-06-17 1998-01-13 Rio Linda Chemical Co., Inc. Generation and storage of chlorine dioxide in a non-aqueous medium
US6077502A (en) * 1998-02-27 2000-06-20 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6132702A (en) * 1998-02-27 2000-10-17 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6251372B1 (en) 1998-02-27 2001-06-26 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6350438B1 (en) 1998-02-27 2002-02-26 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6582682B2 (en) 2000-10-30 2003-06-24 Noville, Inc. Oral care compositions comprising stabilized chlorine dioxide
US6696047B2 (en) 2001-09-13 2004-02-24 The Procter & Gamble Company Stable oral care compositions comprising chlorite
EP2133083A1 (fr) * 2007-03-27 2009-12-16 Taiko Pharmaceutical Co. Ltd. Agent thérapeutique pour une maladie infectieuse cutanée ou des muqueuses
EP2525802A2 (fr) * 2010-01-19 2012-11-28 Sinox Pharma, Inc. Procédé de traitement de la sinusite, comprenant la sinusite chronique
US8992831B2 (en) 2009-09-25 2015-03-31 E. I. Du Pont De Nemours And Company Stabilized chlorine dioxide to preserve carbohydrate feedstocks
WO2018202897A1 (fr) 2017-05-04 2018-11-08 Schaub Walter Compositions et procédures de traitement pour le traitement d'infections pathogènes
CN115068500A (zh) * 2022-06-20 2022-09-20 张海杰 一种治疗幽门螺杆菌的药物

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US4073888A (en) * 1974-06-18 1978-02-14 Pettibone Laboratories, Inc. Chlorine dioxide and quaternary ammonium salts as sterilizing agents
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US4317814A (en) * 1980-06-12 1982-03-02 Felipe Laso Preparation and method for treating burns
US4330531A (en) * 1976-03-26 1982-05-18 Howard Alliger Germ-killing materials
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EP0519152A1 (fr) * 1991-06-17 1992-12-23 Rio Linda Chemical Co., Inc. Production de dioxyde de chlore dans un milieu non-aqueux
EP0561145A1 (fr) * 1992-03-19 1993-09-22 Oxo Chemie Ag Utilisation d'une matrice faite à base de chlorite pour la manufacture de préparations médicinales pour le traitement d'infections causées par le HIV
US6086922A (en) * 1992-03-19 2000-07-11 Oxo Chemie Ag Use of a chemically-stabilized chlorite matrix for the parenteral treatment of HIV infections
US5736165A (en) * 1993-05-25 1998-04-07 Allergan In-the-eye use of chlorine dioxide-containing compositions
EP0748161A1 (fr) * 1994-03-04 1996-12-18 Alcide Corporation Desinfection et reparation de lesions
EP0748161A4 (fr) * 1994-03-04 1998-12-09 Alcide Corp Desinfection et reparation de lesions
WO1995027472A1 (fr) * 1994-04-07 1995-10-19 Richter Jon L Solution pour bains de bouche et procede de traitement de la bromopnee
WO1996002264A2 (fr) * 1994-07-20 1996-02-01 Allergan, Compositions contenant du dioxyde de chlore a utilisation ophtalmique
WO1996002264A3 (fr) * 1994-07-20 1996-03-14 Allergan Inc Compositions contenant du dioxyde de chlore a utilisation ophtalmique
US6096350A (en) * 1995-09-08 2000-08-01 Alcide Corporation Compositions and methods for prevention and treatment of diseases associated with honey bees
WO1997008954A1 (fr) * 1995-09-08 1997-03-13 Alcide Corporation Compositions et procedes pour la prevention et le traitement des maladies associees aux abeilles domestiques
US6235269B1 (en) 1998-02-27 2001-05-22 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6132702A (en) * 1998-02-27 2000-10-17 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6077502A (en) * 1998-02-27 2000-06-20 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6251372B1 (en) 1998-02-27 2001-06-26 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6264924B1 (en) 1998-02-27 2001-07-24 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
US6350438B1 (en) 1998-02-27 2002-02-26 The Procter & Gamble Company Oral care compositions comprising chlorite and methods
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US6696047B2 (en) 2001-09-13 2004-02-24 The Procter & Gamble Company Stable oral care compositions comprising chlorite
EP2133083A4 (fr) * 2007-03-27 2012-02-15 Taiko Pharmaceutical Co Ltd Agent thérapeutique pour une maladie infectieuse cutanée ou des muqueuses
EP2133083A1 (fr) * 2007-03-27 2009-12-16 Taiko Pharmaceutical Co. Ltd. Agent thérapeutique pour une maladie infectieuse cutanée ou des muqueuses
US8992831B2 (en) 2009-09-25 2015-03-31 E. I. Du Pont De Nemours And Company Stabilized chlorine dioxide to preserve carbohydrate feedstocks
US9504710B2 (en) 2009-09-25 2016-11-29 E I Du Pont De Nemours And Company Stabilized chlorine dioxide to preserve carbohydrate feedstocks
EP2525802A2 (fr) * 2010-01-19 2012-11-28 Sinox Pharma, Inc. Procédé de traitement de la sinusite, comprenant la sinusite chronique
EP2525802A4 (fr) * 2010-01-19 2013-11-06 Sinox Pharma Inc Procédé de traitement de la sinusite, comprenant la sinusite chronique
US10201563B2 (en) 2010-01-19 2019-02-12 Sinox Pharma, Inc. Method of treating sinusitis, including chronic sinusitis
WO2018202897A1 (fr) 2017-05-04 2018-11-08 Schaub Walter Compositions et procédures de traitement pour le traitement d'infections pathogènes
JP2020519683A (ja) * 2017-05-04 2020-07-02 ウォルター ショーブ 病原性感染の処置のための組成物及び処置手順
JP7299876B2 (ja) 2017-05-04 2023-06-28 ウォルター ショーブ 病原性感染の処置のための組成物及び処置手順
CN115068500A (zh) * 2022-06-20 2022-09-20 张海杰 一种治疗幽门螺杆菌的药物

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