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WO2003017961A1 - Composition orale antimicrobienne et sa methode d'utilisation - Google Patents

Composition orale antimicrobienne et sa methode d'utilisation Download PDF

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Publication number
WO2003017961A1
WO2003017961A1 PCT/US2001/026439 US0126439W WO03017961A1 WO 2003017961 A1 WO2003017961 A1 WO 2003017961A1 US 0126439 W US0126439 W US 0126439W WO 03017961 A1 WO03017961 A1 WO 03017961A1
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WIPO (PCT)
Prior art keywords
solution
weight
range
hydrogen peroxide
composition
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Application number
PCT/US2001/026439
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English (en)
Inventor
Joseph A. Sasson
Ricardo Panicucci
Original Assignee
Sasson Joseph A
Ricardo Panicucci
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 Sasson Joseph A, Ricardo Panicucci filed Critical Sasson Joseph A
Priority to PCT/US2001/026439 priority Critical patent/WO2003017961A1/fr
Publication of WO2003017961A1 publication Critical patent/WO2003017961A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the present invention describes a two-stage system capable of in situ generation of chlorine dioxide (ClO 2 ) in the presence of hydrogen peroxide (H 2 O 2 ) for use in a chemical formulation, more specifically an antimicrobial composition suitable for prophylactic and therapeutic use, including the treatment and prevention of oral disease.
  • the system is capable of generating sufficient ClO 2 so that, when used in the oral cavity, the composition may inhibit plaque formation, inhibit gingival inflammation and periodontal inflammation, reduce dental caries, and control oral malodor.
  • ClO 2 a strong oxidizing agent. ClO 2 is well documented as a bactericidal, bacteriostatic, fungicidal, fungistatic, viricidal, and viralstatic agent. It is approved by the EPA under Registration Number 9048-3 for both water purification and food preparation and preservation because of this antimicrobial activity.
  • ClO 2 is also effective in treating malodor. It achieves this efficacy by two mechanisms of action. First, ClO 2 oxidizes the sulfide bonds of volatile and odoriferous sulfur compounds (specifically hydrogen sulfide and di-methyl mercaptan bonds) that are metabolic byproducts released by certain anaerobic bacteria documented to reside in the oral cavity; and second, its antimicrobial activity lowers the number of such microorganisms that release these volatile sulfur compounds.
  • volatile and odoriferous sulfur compounds specifically hydrogen sulfide and di-methyl mercaptan bonds
  • ClO 2 is unstable in an aqueous solution and, as such, cannot be stored at room temperature. Furthermore, since ClO 2 is a gas, it cannot be stored in liquid form at room temperature. Thus, various references to "stabilized" ClO 2 do not refer to gaseous ClO 2 , but rather to various chlorous acid- liberating compounds. Unfortunately, chlorous acid, even when buffered, will dernineralize tooth enamel and lead to even more significant oral health problems.
  • One such chlorous acid-liberating compound used is sodium chlorite (NaClO 2 ).
  • compositions for treating oral malodor that employ chlorine-containing compounds are disclosed in U.S. Pat. No. 5,772,986 to Richter; U.S. Pat. No. 5,738,840 to Kross; U.S. Pat. No. 4,552,679 to Schubel, and U.S. Pat. No. 4,808,389 to Ratcliff.
  • These references disclose various vehicles for introducing the compositions to the oral cavity, including liquid rinses, toothpastes (either with or without suds), lozenges, and sprays, as disclosed in U.S. Pat. No. 4,837,009 to Ratcliff.
  • the chemical mechanisms for producing compositions containing chlorous acid are varied.
  • Some references, such as Ratcliff '215 describe the generation of chlorous acid at controlled pH levels using phosphate buffers.
  • U.S. Pat. Nos. 4,891,216 to Kross and 4,902,498 to Agricola et al. disclose a two part system that generates chlorous acid by mixing a metal chlorite or other chlorous acid-liberating compound with a protic acid at acidic pH levels.
  • U.S. Pat. No. 5,667,817 to Kross discloses a two-stage system that requires the use of lactic acid and that results in a composition having a very disagreeable taste, making it unsuitable for use in oral healthcare. As a consequence, this product is not commercially available. However, even those products that are commercially available have significant drawbacks due to their complex chemistries, poor shelf life, poor taste, and poor efficacy.
  • reaction is unidirectional, not only is the product's shelf-life determined by the amount of metal chlorite initially present in the system and its pH, but the end-user is unable to determine how much chlorous acid is present at any given time, as the amount of chlorous acid in the system decays over time.
  • Non-chlorous acid-containing products such as Mentadent ® (active ingredients: baking soda and H 2 O 2 ) and Listerine ® (active ingredients: thymol, eucalyptol, and methyl salicilate) oral rinses achieve plaque inhibition rates of only 15% and 30%, respectively. These levels are well below the therapeutic and prophylactic benchmark of about 50% plaque inhibition achieved by Peridex ® oral rinse (active ingredient: chlorhexidine gluconate), which is available only by prescription.
  • Peridex ® active ingredient: chlorhexidine gluconate
  • Peridex ® is the most-effective, commercially available plaque inhibitor, it has serious drawbacks that limit its applicability. Most significant among these drawbacks is severe staining to hard oral tissues observed even with brief use.
  • the ideal oral care composition would be available over-the-counter yet achieve plaque inhibition rates comparable to compositions currently available only by prescription, inhibit gingival inflammation and periodontal inflammation, reduce dental caries, and control oral malodor.
  • the ideal composition should provide equivalent or superior efficacy to known compositions, yet be pleasing to the taste, thereby increasing patient compliance.
  • the ideal composition should have a superior shelf life due to the chemical stability of the component reactants.
  • the composition should be easy to use and have a simple chemistry that reacts under normal environmental conditions (i.e., at ambient temperature and pressure and without the need for multiple steps, pressurized containers, etc.).
  • the composition once fully constituted should have a pH value that is suitable for oral use and not be harmful to the teeth or oral tissues.
  • the ideal composition should have an effervescent quality for increased aeration of the oral tissues to facilitate the reduction of anaerobic bacteria and other microbes.
  • the ideal composition should not stain the teeth, provide an environment for future plaque buildup, require additional treatment, or make the teeth more susceptible to caries.
  • the ideal composition would enable the rapid, reliable, and predictable generation in situ of therapeutic levels of ClO 2 .
  • the present invention is directed to a method of treating or reducing the risk of a microbial infection using a composition made by mixing a solution of a water soluble metal chlorite with a solution of hydrogen peroxide and an oxidizing agent (other than hydrogen peroxide).
  • the composition is especially useful as an oral rinse for treating or reducing the risk those microbial infections associated with dental disease, such as gingivitis, dental caries and oral malodor.
  • the method comprises the steps of: a) providing a first solution comprising a water-soluble chlorite compound, said chlorite compound present at a concentration in the range of about 0.1 to 0.5% by weight, and said first solution having an alkaline pH; b) providing a second solution comprising an oxidizing agent and hydrogen peroxide, said oxidizing agent present at a concentration in the range of about 1.0 to 10% by weight, said hydrogen peroxide present at a concentration in the range of about 0.3 to 1.5% by weight, and said second solution having a pH in the range of about 1 to 6; c) mixing the first solution and the second solution together to provide an antimicrobial composition, wherein said composition has a pH below about 7; and d) applying the composition of step (c) to the locus of the microbial infection.
  • a preferred water soluble chlorite compound for the first solution is NaClO 2 .
  • other water soluble metal salts of chlorite including other alkali metal salts and group (IT) salts (e.g., calcium and magnesium salts) can also be used.
  • the water soluble chlorite is present at a concentration in the range of about 0.1 to 0.5% by weight, preferably about 0.25 to 0.32%.
  • This first solution is maintained at an alkaline pH above about 7, preferably around pH 8.
  • the oxidizing agent is required to be physiologically acceptable, i.e., suitable for administration to humans.
  • the oxidizing agent is also required to be suitable for oxidizing the chlorite to ClO 2 .
  • Suitable oxidizing agents generally have a reduction potential greater than the value of 0.954 volts and include, but are not limited to: (1) inorganic oxidants (e.g., salts of persulfate, iodate (IO 3 " ), bromate (BrO 3 ), permanganate (MnO 4 " ), hypochlorite (OC1 " ) and the like); (2) organic peroxides (e.g., alkyl and aryl hydroperoxides such as tert-butyl hydroperoxide and benzoyl hydroperoxide, and dialkyl, diaryl, or mixed alkyl aryl peroxides having the required reduction potential); (3) organic peracids (e.g., alkyl and aryl peracids, such as per
  • metal persulfate salts are preferred, i.e., metal persulfate salts suitable for administration to humans.
  • metal persulfate salts suitable for administration to humans. Examples include persulfate salts of sodium, potassium, lithium, calcium and the like. Sodium persulfate is a preferred oxidizing agent.
  • the second solution comprising the oxidizing agent preferably sodium persulfate and hydrogen peroxide (H 2 O 2 ) is maintained at a pH in the range of about 1 to 6.
  • the oxidizing agent is present at a concentration in the range of about 1.0 to 10%) by weight, preferably in the range of about 3 to 5%.
  • the term "hydrogen peroxide" as used herein includes hydrogen peroxide itself as well as any peroxide generator such as urea peroxide, zinc peroxide, calcium peroxide, sodium percarbonate and the like.
  • the hydrogen peroxide is present at a concentration in the range of 0.3 to 1.5% by weight, preferably in the range of about 0.3 to 0.75%.
  • ClO 2 is formed by the oxidation of the water-soluble chlorite compound as described by the reactions shown below.
  • Chlorine dioxide is a known antimicrobial agent. Hydrogen peroxide is also believed to be responsible in part for the therapeutic effectiveness of the present compositions, even though it is known that in the presence of H 2 O 2 , ClO 2 is reduced back to ClO 2 " and hydrogen peroxide is consumed.
  • Applicants have found that when there is an adequate amount of oxidizing agent, as described herein, relatively small amounts of water soluble metal chlorite and hydrogen peroxide may be used together to provide an effective oral rinse.
  • the amounts of water soluble metal chlorite compound, hydrogen peroxide and oxidizing agent ingredients described above are based on mixing the first and second solutions in approximately equal volumes. These volumes may be varied to adjust for variations in the concentration of the ingredients in the first and second solutions.
  • another embodiment of the invention relates to a method for treating or reducing the risk of a microbial infection comprising the step of applying an antimicrobial composition having a pH below about 7 to the locus or surface of the microbial infection, wherein said composition is prepared by mixing a first solution with a second solution, the first solution comprising a water soluble metal chlorite and the second solution comprising a suitable oxidizing agent, as described above (e.g., sodium persulfate), and hydrogen peroxide.
  • a suitable oxidizing agent as described above (e.g., sodium persulfate), and hydrogen peroxide.
  • the resulting mixture comprises about 0.05 to 0.25% of the water soluble metal chlorite, about 0.5 to 5% of the oxidizing agent (e.g., sodium persulfate) and about 0.15 to 0.75% hydrogen peroxide, wherein all quantities are based on the weight of the antimicrobial composition.
  • the oxidizing agent e.g., sodium persulfate
  • hydrogen peroxide e.g., sodium persulfate
  • ClO 2 at a concentration in the range of about 1 to 100 ppm, preferably in the range of about 2 to 20 ppm; hydrogen peroxide in the range of about 0.15 to 0.75%, preferably in the range of about 0.15 to 0.4%; oxidizing agent in the range of about 0.5 to 5%, preferably 1.5 to 2.5%; and ClO 2 " in the range of about 0.05 to 0.5%.
  • another embodiment of this invention relates to a method for treating or reducing the risk of microbial infection comprising the step of applying to the locus of the microbial infection an antimicrobial composition
  • an antimicrobial composition comprising (a) ClO 2 at a concentration in the range of about 1 to 100 ppm, preferably in the range of about 2 to 20 ppm; (b) hydrogen peroxide in the range of about 0.15 to 0.75% by weight, preferably in the range of about 0.15 to 0.4%; (c) oxidizing agent in the range of about 0.5 to 5% by weight, preferably 1.5 to 2.5%; and (d) ClO 2 " in the range of about 0.05 to 0.5% by weight, wherein the pH of the composition is below about 7.
  • any suitable buffer may optionally be used such as a bicarbonate buffer, a citrate buffer or a phosphate buffer. When used, the buffer will typically be present at a concentration in the range of about 0.1 to 1.0% by weight. Bicarbonate is a preferred buffer system. Any suitable food-grade acid or base may be used to prepare the buffer system or to otherwise adjust the pH. Preferred acids are phosphoric acid and citric acid, optionally supplemented by tannic acid, and a preferred base is sodium bicarbonate.
  • the composition may contain optional ingredients to improve taste, appearance or mouthfeel in order to enhance its appeal to the consumer.
  • optional ingredients include colorants, sweeteners, flavorings and surfactants that are known ingredients in commercially available mouthwash.
  • colorants include FDC Red 40, FDC Green 3, FDC Brown mixture, FDC Yellow 5, DC Red 19, DC Red 33, DC Yellow 10, and the like, which are typically present in about 0.01 to 0.2 weight percent.
  • suitable sweeteners include glycerin and sugar alcohols like sorbitol or artificial sweeteners such as aspartame, saccharin or acesulfame.
  • Sweetening agents are generally used at levels of from about 0.005% to about 2% by weight of composition.
  • flavorants include oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, cinnamon, lemon, orange, and methyl salicylate.
  • Flavorants are used in a quantity of about 0.1 percent by weight.
  • a surfactant can be added as an optional ingredient in a quantity of about 0.2-2 weight percent, and preferably is selected from orally-compatible nonionic and anionic polymers which are commercially available for oral hygiene applications.
  • Nonionic oral surfactants are illustrated by laurate esters of sorbitol consisting of the monoester condensed with about 15-25 moles of ethylene oxide, such as Tween 20 (ICI Americas).
  • Another suitable type of oral surfactants are the polymers of polyoxyethylene and polyoxypropylene, such as Pluronic F-108 (BASF- Wyandotte).
  • Anionic oral surfactants are illustrated by alkyl sulfonates and sulfates, such as sodium lauryl sulfate or a sulfonated monogJyceride of a C, 0 -C lg fatty acid.
  • the present composition may also contain deodorizing agents, anti-foam agents, ethanol or other alcohols, as well as other conventional ingredients.
  • the present composition be prepared fresh from the two solutions and used at or near the time of preparation.
  • the composition is best used between about 1 to 5 minutes after it is prepared. However, if the composition is left to sit for several hours, its effectiveness will begin to diminish.
  • suitable containers have been developed for maintaining separate solutions that are to be mixed at the time of use by the consumer. US Patents 5,252,312, 5,289,950 and 5,392,947, incorporated herein by reference, describe such dispensing containers for dental moutwash.
  • the containers have at least two discreet compartments so that the contents of the compartments maybe dispensed simultaneously.
  • kits or dental mouthwash products comprising two components.
  • the kit or dental mouthwash product can be used in therapy, for example, for treating and/or reducing the risk of microbial infections such as those associated with dental disease.
  • Thetician ⁇ . -. shall make sure that i-n t ⁇ » m nii ⁇ rtiirp nf ⁇ TnpHirnm f vnt for use in treating or reducing the risk of said microbial infections.
  • the kit or dental mouthwash product comprises: a) first liquid component comprising a water-soluble chlorite compound, said chlorite compound present at a concentration in the range of about 0.1 to 0.5% by weight, and said first component having an alkaline pH; and b) a second liquid component comprising a second solution comprising an oxidizing agent, as described herein (preferably sodium persulfate) and hydrogen peroxide, said oxidizing agent at a concentration in the range of about 1.0 to 10% by weight, said hydrogen peroxide present at a concentration in the range of about 0.3 to 1.5% by weight, and said second component having a pH in the range of about 1 to 6.
  • an oxidizing agent as described herein (preferably sodium persulfate) and hydrogen peroxide
  • the kit or dental mouthwash product additionally comprises: c) dispensing container which houses a first compartment with an outlet end containing the first liquid component and a second compartment with an outlet end containing the second liquid component; d) a closure mechanism for closing the compartments over the outlet ends; and e) a closure means for allowing the first and second liquid components to be simultaneously dispensed.
  • dispensing container which houses a first compartment with an outlet end containing the first liquid component and a second compartment with an outlet end containing the second liquid component
  • a closure mechanism for closing the compartments over the outlet ends
  • a closure means for allowing the first and second liquid components to be simultaneously dispensed.
  • Such containers are especially well-suited to simultaneously dispensing equal quantities of the two liquid components.
  • the outer walls of one or both of the compartments may be constructed of a translucent or clear material so that the liquid level within the container may be viewed.
  • the composition may be used as an oral rinse for treating dental disease.
  • Such disease includes gingivitis, dental caries and oral malodor.
  • the amount of composition and the frequency of treatment may be varied depending on the type and severity of the disease and on the mode of application.
  • the amount of composition used per treatment may vary from about 0.1 ml to 100 ml depending on the application. The lower amounts may be sufficient if the composition is to be applied directly, for example, by using a syringe or other means of direct application.
  • the amounts typically vary from a few milliliters to about 100 ml per treatment, preferably from about 25 to 50 ml.
  • composition may be used as a mouthwash daily or multiple times during the day or in accordance with a treatment regimen that would be prescribed by one skilled in the art of dental care.
  • treatments will generally be made once to a few times per day, preferably twice per day.
  • the composition may also be used in dental appliance therapy, especially for treating extra-oral appliances such as removable partial dentures, full dentures, night guards, and orthodontic appliances.
  • the appliance is treated by immersing it in the composition for a suitable period of time, usually about 10 to 15 minutes.
  • the pH of the resulting composition should be below 7, but above the pK a of chlorous acid. It is known that ClO 2 is generated from NaClO 2 at pH values below 7 in the absence of an oxidizing agent such as However, the generation is quite slow (on the order of days and months). In the presence of an oxidizing agent such as under the conditions described above, therapeutic levels of ClO 2 are believed to be generated in seconds. Increasing the concentration of the oxidizing by weight will cause a more rapid generation of ClO 2 . Table 1 shows that for a constant level of NaClO 2 the generation of ClO 2 increases with increasing The levels of ClO 2 generated by this reaction are within the levels that are expected to' inhibit the formation of gingival plaque.
  • the pH of the persulfate/peroxide- containing component should be sufficiently acidic such that upon mixing with the NaClO 2 /bicarbonate-containing component the resulting pH is less than 7.
  • Table 3 below shows a formula for the two-component system of the present invention.
  • the ranges given below represent the various conditions that could result in levels of ClO 2 that inhibit plaque.
  • the ClO 2 levels will be dependent on the level of NaClO 2 in the base and the level of H 2 O 2 and in the activator.
  • the level of NaHCO 3 in the base will determine the level of phosphoric acid (H 3 PO 4 ) that should be used in order to adjust the pH of the activator.
  • the resulting pH should be below 7.
  • Increasing levels of NaHCO j in the base therefore will require increasing levels of phosphoric acid in the activator to achieve a final pH of less than 7 when the two phases are mixed.
  • the lower levels of NaClO 2 and Na 2 S 2 O g can be used to generate the desired levels of ClO 2 if the H 2 O 2 is eliminated from the formulation.
  • the level of NaHCO 3 will not effect the generation of ClO 2 where no H 2 O 2 is present.
  • the pH of the resulting solution should be below 7 if NaHCO 3 is used in the formula. It may be desirable in some applications to include bicarbonate but not H 2 O 2 .
  • Flavor 0.5 Flavor 0.5
  • Table 5 Clinical results obtained in the double-blind, two-cell, 48 hour plaque inhibition study against a water placebo control
  • the mean values shown in Table 5 are mean plaque scores for each tooth surface examined on the Ramfjord teeth. The greater the mean value, the greater the relative plaque accumulation.
  • the data show that the ClO 2 group mean plaque scores were significantly lower than the water placebo group mean scores for all individual surfaces and for the total mouth. Therefore it can be concluded that the ClO 2 rinse is significantly more efficacious than water in the inhibition of dental plaque on the teeth, over a 48 hour period with four applications.
  • the present invention has applicability for use on the vaginal, anal, nasal, and ocular mucous membrane surfaces, topically, and in vitro, as, e.g., as a contact lens wash or dental apparatus wash. While this invention has been particularly shown and described with references to preferred embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention encompassed by the appended claims.

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Abstract

L'invention concerne une composition antimicrobienne liquide particulièrement utile en tant que bain de bouche pour traiter ou pour réduire le risque de maladie dentaire. Cette composition est préparée au moyen d'un mélange d'une première solution comprenant un constituant de chlorite métallique soluble dans l'eau et d'une seconde solution comprenant un agent d'oxydation physiologiquement acceptable pouvant oxyder un chlorite pour obtenir du ClO2 et du peroxyde d'hydrogène. La composition obtenue, contenant du dioxyde de chlore, est de préférence utilisée au moment de la préparation en appliquant la composition à l'endroit où le traitement est voulu.
PCT/US2001/026439 2001-08-24 2001-08-24 Composition orale antimicrobienne et sa methode d'utilisation WO2003017961A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005006462A1 (de) * 2005-02-12 2006-09-07 Templa Tech Gmbh Mittel zur Behandlung von Infektionen
WO2015084295A1 (fr) * 2013-12-02 2015-06-11 Colgate-Palmolive Company Système d'oxydation pour compositions de soin buccal
WO2015084296A1 (fr) * 2013-12-02 2015-06-11 Colgate-Palmolive Company Système oxydant bicomposant pour compositions de soins buccaux

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271242A (en) * 1963-03-29 1966-09-06 Alexander R Reed Iii Stable chlorine dioxide composition and method of making same
US4296103A (en) * 1980-08-08 1981-10-20 Felipe Laso Stabilized solution of chlorine oxides
DE3403631A1 (de) * 1983-02-25 1984-08-30 Peter 6900 Heidelberg Berger Verfahren zur herstellung einer modifizierten waessrigen chloritloesung, die danach hergestellte loesung sowie deren verwendung
US4574084A (en) * 1983-02-25 1986-03-04 Peter Berger Process for the preparation of a modified aqueous chlorite solution, the solution prepared by this process and the use thereof
WO1990006101A1 (fr) * 1986-03-31 1990-06-14 Ratcliff Perry A Procede et composition ameliores de prevention de la formation de plaque et de maladies associees a la plaque
DE19854349A1 (de) * 1998-11-25 2000-05-31 Up To Dent Ag Balzers Mundpflegemittel

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271242A (en) * 1963-03-29 1966-09-06 Alexander R Reed Iii Stable chlorine dioxide composition and method of making same
US4296103A (en) * 1980-08-08 1981-10-20 Felipe Laso Stabilized solution of chlorine oxides
DE3403631A1 (de) * 1983-02-25 1984-08-30 Peter 6900 Heidelberg Berger Verfahren zur herstellung einer modifizierten waessrigen chloritloesung, die danach hergestellte loesung sowie deren verwendung
US4574084A (en) * 1983-02-25 1986-03-04 Peter Berger Process for the preparation of a modified aqueous chlorite solution, the solution prepared by this process and the use thereof
WO1990006101A1 (fr) * 1986-03-31 1990-06-14 Ratcliff Perry A Procede et composition ameliores de prevention de la formation de plaque et de maladies associees a la plaque
DE19854349A1 (de) * 1998-11-25 2000-05-31 Up To Dent Ag Balzers Mundpflegemittel

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005006462A1 (de) * 2005-02-12 2006-09-07 Templa Tech Gmbh Mittel zur Behandlung von Infektionen
WO2015084295A1 (fr) * 2013-12-02 2015-06-11 Colgate-Palmolive Company Système d'oxydation pour compositions de soin buccal
WO2015084296A1 (fr) * 2013-12-02 2015-06-11 Colgate-Palmolive Company Système oxydant bicomposant pour compositions de soins buccaux
CN105792799A (zh) * 2013-12-02 2016-07-20 高露洁-棕榄公司 用于口腔护理组合物的氧化体系
CN105792896A (zh) * 2013-12-02 2016-07-20 高露洁-棕榄公司 用于口腔护理组合物的两部分氧化体系
US20160296433A1 (en) * 2013-12-02 2016-10-13 Colgate-Palmolive Company Two-part oxidizing system for oral care compositions
AU2013406828B2 (en) * 2013-12-02 2017-03-09 Colgate-Palmolive Company Two part oxidizing system for oral care compositions
AU2013406827B2 (en) * 2013-12-02 2017-05-18 Colgate-Palmolive Company Oxidizing system for oral care compositions

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