WO2011094872A1 - Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients - Google Patents
Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients Download PDFInfo
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- WO2011094872A1 WO2011094872A1 PCT/CH2010/000029 CH2010000029W WO2011094872A1 WO 2011094872 A1 WO2011094872 A1 WO 2011094872A1 CH 2010000029 W CH2010000029 W CH 2010000029W WO 2011094872 A1 WO2011094872 A1 WO 2011094872A1
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- 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
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- 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
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- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
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- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
Definitions
- the invention relates to liquid oral care compositions, particularly in the form of a mouth spray or gurgling rinse, comprising non-ionic surfactants, flavoring oils, precursors of C102.
- the invention further relates to the manufacture and use thereof.
- Chlorine dioxide (C102) is known in the field to function as bactericidal, bacteristatic, fungicidal, fungistatic, antimicrobial, antiseptic and antiviral as well as oxidizing agents (especially towards VSC's) even at very low concentrations, making it the most efficient and oral care application suitable agent towards reducing plaque count, halitosis and other related disadvantageous issues. Precursors thereof are typically used to formulate oral compositions.
- these precursors due to their strong oxidizing property, are difficult to formulate commercial end-user products with, particularly, o/w microemulsions that possess (1) reasonable shelf-life (preferably more than 24 months), (2) stability of the ingredients used over the shelf-life, (3) stability of the composition over the shelf-life, (4) retention of quality of flavor, fragrance, taste and color, and (5) retention of packaging material.
- US 2008/247972 discloses a alcohol-free aqueous mouthwash comprising an oxidizing agent and a bactericide, for the prevention and treatment of halitosis.
- the disclosed example provides 0.6% H202, 0.5% Polysorbate 20 and 0.15% flavors.
- the composition disclosed in this document does not form a stable isotropic clear o/w microemulsion. Further, the composition disclosed has a short shelf-life and instability in flavor.
- US 6696047 discloses certain oral care compositions comprising chlorite and a chlorite stable flavor system, such as a dual phase rinse, for treatment of halitosis.
- Chlorite stable flavor systems of this document are substantially free of chlorite sensitive compounds that degrade in the presence of chlorite (see claim 1). Consequently, a number of known and well accepted flavors, such as Peppermint-, Wintergreen- or Eucalyptus oil, are less suited for this composition. Further, the presence of ethanol in a dual phase rinse (see ex.
- VSCs volatile sulfur compounds
- US 6582682 discloses certain oral care compositions in the form of a microemulsion comprising chlorite and ethoxylated hydrogenated castor oil, for treatment of halitosis. It has been found that none of these examples provided are stable for more than 3 weeks (stability test at 40°C) , resulting (1) phase separation, (2) yellowing and (3) depletion in NaC102 concentration by more than 90%.
- micellar aggregates were not (1) stable enough towards leaking entrapped flavor / lipophilic substance from the micellar core, (2) micellar aggregates were not efficient enough to avoid confrontation between flavor phase and aqueous phase containing NaC102, and (3) micellar aggregates may be too large which facilitates intermicellar coalescence within a short time during storage releasing entrapped flavoring agents to confront with aqueous NaC102 and stipulating phase separation to the overall composition. Therefore the disclosed compositions in this prior art document are not stable and suitable in formulating practical and commercial oral-care products.
- treatment of a disorder shall, in the context of this invention, also include the prevention and/or delay of progression of said disorder.
- microemulsion is known in the field. It particularly denotes a thermodynamically stable isotropic disper- sion of two immiscible liquids stabilized by a surfactant, often in combination with a co-surfactant. Such dispersion comprises homogeneously distributed droplets with diameter less than lOOnm throughout a continuous phase making it clear and transparent or opalescent.
- An aqueous phase (which is typically the continuous phase) may contain dissolved electrolytes and any water-soluble species.
- the oil phase (which typically form the dispersed phase, droplets) may be a mixture of water-insoluble lipophilic substances.
- microemulsions appear to be a clear transparent / opalescent mono-phase solution to human eye, they are actually a three-component (ternary) system, designated as oil / surfactant / water or water / surfactant / oil, wherein surfactant molecules form the interface through self-assembly with various possible structures of which micellar assembly is most frequent and common.
- oil / surfactant / water or water / surfactant / oil wherein surfactant molecules form the interface through self-assembly with various possible structures of which micellar assembly is most frequent and common.
- the second type is "reverse” / "inverse” wherein water, which is the minor component, is dispersed in the oil, which is the major component, designated by w/o.
- M n aggregate / shelf-assembly of surfactant molecules (nM) dispersed in a liquid colloid
- M denotes a surfactant molecule, often referred to as surfactant monomer
- M n denotes a micelle due to aggregation of n surfactant monomers
- n is number of surfactant molecule/monomers.
- micelles there are two types of micelles: (1) Direct / typical micelle, designated by o/w, and (2) reverse / inverse micelle, denoted by w/o.
- Co-surfactant is known in the field.
- a co-surfactant is either a mono- or a poly-ol species.
- the term "Micellar migration” is known in the field. It particularly denotes the exchange of surfactant monomers, solubilized ingredients and fragment of micelle (fragment of surfactant aggregate that comprises surfactant monomers, solubilized ingredients and co-surfactant molecules) among the micelles.
- liquid oral solution composition is known in the field. It particularly denotes a mouthwash, mouth spray, gurgling rinse and mouth rinse.
- the invention relates to a liquid oral care composition, preferably in the form of a micro- emulsion, containing (i.e. comprising or consisting of) a) one or more non-ionic surfactants, preferably selected from the group consisting of polyoxyethylene sorbitan mono-esters of Ci2 ⁇ i8 fatty acids;
- one or more lipophilic excipients preferably selected from flavoring oils
- alkali metal chlorites selected from the group consisting of alkali metal chlorites, - chlorates and - hypochlorites
- phosphate compound selected from the group consisting of alkali pyrophosphate
- inventive compositions have a shelf-life of 36 months or longer at room temperature, do not suffer from yellowing discoloration, do not suffer from denaturation of flavor and taste and do not develop undesirable chlorine odor. Further, the inventive compositions retain 80% of sodium chlorite at the length of 36 months. Further, the inventive compositions show a pronounced effect on oral hygiene and / or oral health, particularly provide excellent results in controlling halitosis .
- Microemulsion The inventive composition is typically present as an o/w microemulsion.
- the flavoring oils (constituent b) are in the micellar interior, surrounded by the surfactant (constituent a) .
- the remaining constituents are present in the continuous aqueous phase.
- Non-ionic surfactants produce relatively larger o/w micelles than ionic surfactants, which are more spacious towards accommodating greater amount of lipophilic substances and more efficient in wrapping up solubilized molecules in their lipophilic core.
- Intermicellar migration involves (1) exit from one micelle, followed by (2) diffusion .in water phase and (3) association to another micelle.
- Migration mechanism involving intermicellar collisions (fusion-fission) is excluded due to strong repulsion potential amongst ionic micelles.
- Micellar collisions take place among the non- ionic micelles due to absence of intermicellar repulsive interaction.
- Intermicellar collision involves (1) temporary coalescence of two micelles during which exchange of surfactant monomers, solubilized additives and micellar fragments between the merged micelles take place, followed by (2) separation and re-formation.
- Micellar migration may take place for both ionic and non-ionic micelles via a third mechanism involving (1) loss of a micellar fragment that contains surfactant monomers, solubilized additives and co-surfactant, followed (2) diffusion in aqueous phase and (3) coagulation to other micelle. Solubilized additives are not embedded in such a fragment as good as in a full micelle, and therefore its diffusion through aqueous phase raises opportunity and probability of confrontation between solubilized lipophilic ingredients and the ingredients soluble in the aqueous phase.
- each constituent a) to g) may be present as one single component (e.g. a single flavoring oil) or as a combination of components (e.g. two or more flavoring oils) .
- the constituents of the inventive composition are known per se (i.e. commercially available or available by known methods) although not combined as disclosed herein.
- Non-ionic surfactants are known in the field.
- pharmaceutically acceptable liquid non-ionic surfactants having a mean HLB number between 10 and 20, preferably between 14 and 19.5, more preferably between 15 and 19 are suitable.
- Such surfactants include Polysorbate 20-80, PEG-PPG-PEG block polymers having molecular weight ranging between 1000 and 6000, and PPG-PEG-PPG block polymers having molecular weight between 1000 and 4000.
- One or more surfactants, preferably one surfactant may be employed in the inventive composition, Particularly good results are obtained when using Polysorbate 20 (e.g. supplied by Goldschmid under the trade name, TEGO SML 20)
- Suitable amounts of constituent a) are in the range of 15 - 30 wt.-%, preferably 18 - 22 wt.-%.
- the amount of surfactant used in the inventive composition is comparatively high. Without being bound to theory, it is believed that such high concentration improves stability of the composition and avoids the use of co-surfactants, as discussed below .
- Constituent b) One or more lipophilic excipients, particularly flavoring oils, may be employed in the inventive composition.
- flavoring oils are selected from the group consisting of Peppermint oil, Spearmint oil, Wintergreen oil, Eucalyptus oil. Particularly good results are obtained when said flavoring oils are extracted from leaves of the corresponding plants.
- Such oils are commercially available as "extra pure” (e.g. supplied by Essencia, Winterthur, Switzerland) . It was surprisingly found that flavoring oils of "extra pure” grade provided particularly good results. Without being bound to theory, it is believed that the absence of impurities in the flavoring oil stabilized the inventive composition, thereby providing an advantageous embodiment of the present invention.
- Suitable amounts of constituent b) are in the range of 0.2 - 8 wt.-%, preferably 0.5 - 5 wt.-%.
- chlorine dioxide precursors water-soluble chlorine dioxide releasing agents
- Such chlorine dioxide releasing agents are known in the field and include alkali metal chlorites, - chlorates and - hypochlorites, preferably alkali metal chlorites and - chlorates, particu ⁇ larly preferably sodium chlorite, potassium chlorite, sodium chlorate and potassium chlorate.
- sodium chlorite is used.
- Suitable amounts of constituent c) are in the range of 0.01 - 0.5 wt.-%, preferably 0.1 - 0.5 wt.-%, particularly preferably 0.2 - 0.35 wt-%.
- Constituent d) One or more water-soluble phosphate com- pounds may be employed in the inventive composition.
- Phosphate compounds are commonly used to regulate the pH and / or to provide an anti - tartar effect.
- Suitable phosphate compounds or combinations thereof, are known in the field and include alkali metal pyrophosphate. Advanta- geously, tetrasodium pyrophosphate is used.
- Suitable amounts of constituent d) are in the range of 0.1 - 2 wt . - %, preferably 0.5 - 1 wt.-%.
- the water employed may be any purity grade of water compliant with the intended use as an oral care product.
- de-ionized water is used. Suitable amounts of water are in the range of 60.05 - 84.5 wt.-%, preferably 70 - 80 wt.-%.
- Constituent f) One or more natural or artificial sweeteners may be added to the inventive composition. The addition of sweeteners is commonly done to improve consumer acceptance; any sweetener or combination of sweeteners known in the field may be used. Preferred are sweeteners that are stable towards oxidizing conditions and soluble in aqueous media, such as Acesulfame-K. Suitable amounts of constituent f) are in the range of 0 - 2 wt.-%, preferably 0.2 - 1 wt.-%.
- Constituent g) One or more isotonic agents may be added to the inventive composition.
- the addition of isotonic agents is commonly done to improve osmotic diffusion through rending the osmotic pressure of the composition close to that of oral mucosa; any isotonic agent or combination of isotonic agents known in the field may be used. It is understood that isotonic agents must be compatible with the intended use as oral care compositions, constituent g) may thus be more precisely defined as "oral isotonic agent” .
- Suitable formulations of the inventive composition are any liquid formulations known in the field.
- the invention thus relates to a composition as described herein, which is an oral care composition, particularly a mouth spray, mouth wash, mouth rinse, gurgling rinse and the like.
- the inventive composition is formulated as a mouth spray.
- Such formulations are suitable for cosmetic and therapeutic treatment, such as described below.
- the inventive composition is formulated as a gurgling rinse.
- Such formulations are particularly suitable for the treatment of flu and bacterial infections to throat and larynx.
- the invention thus relates to an oral care composition as described herein, which is free of, or substantially free of co-surfactants . It was found that the inventive oral care composition is stable and transparent without addition of further co-surfactants. This is surprising considering the compositions disclosed in the prior art. Typically, co-surfactants, such as poly- oles or mono-alcohols, e.g. glycol or ethanol, are used to improve stability of oral care formulations. In an advantageous embodiment, the invention thus relates to an oral care composition as described herein, wherein no additional bactericides and / or no preservatives are present .
- co-surfactants such as poly- oles or mono-alcohols, e.g. glycol or ethanol
- the invention thus relates to an oral care composition as described herein, having a pH between 7 and 11, preferably between 7.5 and 9.5, much preferred between 8 and 9.
- the invention relates to an oral care composition as described herein, having a viscosity similar to water; typically in the range between 2.5 10 "4 and 1.5 10 "3 Pas.
- the invention relates to the use of a compound or composition as described herein in cosmetic applications and / or therapeutic applications.
- the invention provides a composition as disclosed herein as pharmaceutical, particularly for the treatment, prevention and / or delay of progression of halitosis.
- halitosis is known in the field; it also includes oral malodor and bad breath.
- the compositions and methods of treatment of the present invention are particularly effective for treating or preventing halitosis.
- Halitosis may be caused from consumption of disadvantageous foods or drinks; from smoking.
- Halitosis may also be caused from high plaque count. Treatment may be effective irrespective of the underlying cause.
- the invention provides composition as disclosed herein as pharmaceutical, particu larly for the treatment, prevention and / or delay o progression of diseases or conditions of the oral cavity
- diseases or conditions of the oral cavity i known in the field; it particularly denotes periodonta disease, gingivitis, periodontitis, periodontosis, adult and juvenile periodontitis, and other inflammatory conditions of the tissues within the oral cavity, plus caries, necrotizing ulcerative gingivitis, and other conditions such as herpetic lesions, and infections that may develop following dental procedures such as osseous surgery, tooth extraction, periodontal flap surgery, dental implantation, and scaling and root planing.
- dentoalveolar infections e.g., cellulitis of the jaw; osteomyelitis of the jaw), acute necrotizing ulcerative gingivitis (i.e., Vincent's infection), infectious stomatitis (i.e., acute inflammation of the buccal mucosa), and Noma (i.e., gangrenous stomatitis or cancrum oris) .
- dental abscesses e.g., cellulitis of the jaw; osteomyelitis of the jaw
- acute necrotizing ulcerative gingivitis i.e., Vincent's infection
- infectious stomatitis i.e., acute inflammation of the buccal mucosa
- Noma i.e., gangrenous stomatitis or cancrum oris
- compositions and methods of treatment of the present invention are particularly effective for treating or preventing periodontal disease (gingivitis and/or periodontitis) and resulting breath malodor.
- periodontal disease gingivitis and/or periodontitis
- the term “diseases or conditions of the oral cavity” covers systemic and local causes; it thus includes underlying diseases, disorders or malfunctions, such as periodontal diseases and disorders; tongue and throat diseases associated infections, viral infections (such as influenza) , related bad-breath, shore throat problems, and bacterial infections to throat and larynx.
- the term “disease or condition of the oral cavity” covers tooth whitening, tooth discoloration, tooth stain- ing, tooth decay and tooth hypersensitivity.
- the invention provides the use of composition as disclosed herein for the treatment, prevention and / or delay of progression of halitosis and / or diseases or conditions of the oral cavity. In one further embodiment, the invention provides the use of composition as disclosed herein for the manufacturing of a pharmaceutical for the treatment, prevention and or delay of progression of halitosis and / or diseases or conditions of the oral cavity.
- the invention provides a method of treating halitosis and / or diseases or conditions of the oral cavity in a subject in need thereof comprising the step of contacting the oral cavity of said subject with an effective amount of a composition as described herein.
- the invention provides the use of composition as disclosed herein for the cosmetic treatment of oral malodor.
- the invention provides a method of cleaning the oral cavity of a subject in need thereof comprising the step of contacting the oral cavity with an effective amount of a composition as described herein.
- compositions as described herein are clearly different. While a cosmetic effect (such as treatment of halitosis) is directly achieved by one single application, a therapeutic effect (such as treatment of diseases of the oral cavity) is obtained by an application over a prolonged period, e.g. daily application over one week.
- the cosmetic treatment comprises the step of applying once one or two doses of 0.1-1 ml, e.g. 0.25 ml, of the inventive composition.
- the therapeutic treatment comprises the step of multiple applications of one or two doses of 0.1 - 1 ml, e.g. 0.25 ml, of a composition as described above.
- Such multiple applications include applications once a day, twice a day, or 3 times a day over a period of 2 or more days, such as 2 days, 5 days, 1 week, 2 weeks, 1 month.
- the invention relates to the manufacture of compositions as described herein.
- the manufacturing of microemulsions is known in the field and generally comprises the combination of the required constituents at room temperature or elevated temperatures using standard equipment .
- the invention relates to a method for manufacturing composition as described herein, comprising the steps of
- phase A in the form of a microemulsion, containing constituents a) , b) and water;
- composition A and B containing constituents c) , d) , f ) , g) and water c) combining said composition A and B to obtain a microemulsion .
- phase A is manufactured by providing a solution of constituents a) and b) and adding water to this solution under moderate agitation to obtain a microemulsion .
- manufacturing takes place at 15 - 85 °C, preferably at temperature .
- phase A A mixer was charged with Polysorbate. The oils were added with moderate agitation until a clear solution / micro- emulsion was obtained. Water was added slowly to the microemulsion with moderate agitation; the resulting mixture was agitated until a clear / transparent microemul ⁇ sion was obtained: phase A.
- phase B water soluble additives
- Phase B was slowly added to phase A with high agitation. Agitation was continued until a transparent microemulsion was obtained.
- compositions of ex. 1 - 6 possess 36 months of shelf- life.
- compositions of ex. 1 - 6 possess 36 months of shelf- life.
- compositions of ex. 1 - 6 are suitable as a mouthspray.
- a composition according to ex. 1 was clinically tested on more than 100 volunteers of different age and sex groups with halitosis problem, using a halimeter.
- Clinical study furnishes (1) instant extinction of bad-breath with longer than 5 hours of after-effect, (2) reduction of halitosis problem upon systematic intake of the composition over between one and three weeks, and (3) an improvement in whiteness and brightness to the tooth has been observed through "Spectroshade" study on the volunteers upon systematic use of the composition for a week.
- Oxyguard II was tested out on the volunteers, with positive outcome, after consumption of foods and drinks, which are known to cause bad breath, such as garlic enriched foods, beers, vodka, etc.
- it has been tested on the volunteers suffering from Flu and shore-throat problems due to bacterial infections by means of gurgling and rinsing; while an immediate relief was noticed, it beneficially improved their health within 3 days of systematic intake.
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Abstract
The invention relates to liquid oral care compositions, particularly in the form of a mouth spray or gurgling rinse, comprising non-ionic surfactants, flavoring oils, precursors of ClO2. The invention further relates to the manufacture and use thereof.
Description
ORAL CARE COMPOSITION COMPRISING A PRECURSOR OF CHLORINE DIOXIDE AND LIPOPHILIC EXCIPIENTS
The invention relates to liquid oral care compositions, particularly in the form of a mouth spray or gurgling rinse, comprising non-ionic surfactants, flavoring oils, precursors of C102. The invention further relates to the manufacture and use thereof.
Chlorine dioxide (C102) is known in the field to function as bactericidal, bacteristatic, fungicidal, fungistatic, antimicrobial, antiseptic and antiviral as well as oxidizing agents (especially towards VSC's) even at very low concentrations, making it the most efficient and oral care application suitable agent towards reducing plaque count, halitosis and other related disadvantageous issues. Precursors thereof are typically used to formulate oral compositions. However, these precursors, due to their strong oxidizing property, are difficult to formulate commercial end-user products with, particularly, o/w microemulsions that possess (1) reasonable shelf-life (preferably more than 24 months), (2) stability of the ingredients used over the shelf-life, (3) stability of the composition over the shelf-life, (4) retention of quality of flavor, fragrance, taste and color, and (5) retention of packaging material.
Various oral care products are known for their ability to disrupt / prevent plaque formation, remove plaque, reduce and/or extinguish growth of microorganisms in plaque and to treat oral malodor, diseases and disorders, and for the attempts to incorporate them in commercial oral care products .
US 2008/247972 discloses a alcohol-free aqueous mouthwash comprising an oxidizing agent and a bactericide, for the prevention and treatment of halitosis. Specifically, the disclosed example provides 0.6% H202, 0.5% Polysorbate 20
and 0.15% flavors. The composition disclosed in this document does not form a stable isotropic clear o/w microemulsion. Further, the composition disclosed has a short shelf-life and instability in flavor.
US 6696047 discloses certain oral care compositions comprising chlorite and a chlorite stable flavor system, such as a dual phase rinse, for treatment of halitosis. Chlorite stable flavor systems of this document are substantially free of chlorite sensitive compounds that degrade in the presence of chlorite (see claim 1). Consequently, a number of known and well accepted flavors, such as Peppermint-, Wintergreen- or Eucalyptus oil, are less suited for this composition. Further, the presence of ethanol in a dual phase rinse (see ex. 4) is considered disadvantageous due to the fact that it dehydrates and desiccates oral mucosa, increasing cell desquamation and consequently increasing the formation of tongue coating and tonsilloliths, since proteolytic bacteria shall decompose these peeled off cells, originating volatile sulfur compounds (VSCs) in such process, as also being pointed out by US 2008/247972.
US 6582682 discloses certain oral care compositions in the form of a microemulsion comprising chlorite and ethoxylated hydrogenated castor oil, for treatment of halitosis. It has been found that none of these examples provided are stable for more than 3 weeks (stability test at 40°C) , resulting (1) phase separation, (2) yellowing and (3) depletion in NaC102 concentration by more than 90%. These effects may be ascribed by the fact that the micellar aggregates were not (1) stable enough towards leaking entrapped flavor / lipophilic substance from the micellar core, (2) micellar aggregates were not efficient enough to avoid confrontation between flavor phase and aqueous phase containing NaC102, and (3) micellar aggregates may be too large which facilitates intermicellar coalescence within a short time during
storage releasing entrapped flavoring agents to confront with aqueous NaC102 and stipulating phase separation to the overall composition. Therefore the disclosed compositions in this prior art document are not stable and suitable in formulating practical and commercial oral-care products.
Consequently, it is an object of the present invention to provide improved compositions and to mitigate at least some of these drawbacks of the state of the art. In particular, it is an aim of the present invention to provide a composition that has a pronounced effect on oral hygiene and / or oral health, particularly halitosis, and improved shelf life.
These objectives are achieved by a composition as defined in claim 1. Further aspects of the invention are disclosed in the specification and independent claims, preferred embodiments are disclosed in the specification and the dependent claims.
The present invention will be described in more detail below. It is understood that the various embodiments, preferences and ranges may be combined at will. Further, depending on the specific embodiment, selected definitions, embodiments or ranges may not apply.
Unless otherwise stated, the following definitions shall apply in this specification:
The term "containing" shall, in the context of this invention, also include the meaning of comprising or consisting of.
The term "treatment of a disorder shall", in the context of this invention, also include the prevention and/or delay of progression of said disorder.
The term "microemulsion" is known in the field. It particularly denotes a thermodynamically stable isotropic disper-
sion of two immiscible liquids stabilized by a surfactant, often in combination with a co-surfactant. Such dispersion comprises homogeneously distributed droplets with diameter less than lOOnm throughout a continuous phase making it clear and transparent or opalescent. An aqueous phase (which is typically the continuous phase) may contain dissolved electrolytes and any water-soluble species. The oil phase (which typically form the dispersed phase, droplets) may be a mixture of water-insoluble lipophilic substances. Although the microemulsions appear to be a clear transparent / opalescent mono-phase solution to human eye, they are actually a three-component (ternary) system, designated as oil / surfactant / water or water / surfactant / oil, wherein surfactant molecules form the interface through self-assembly with various possible structures of which micellar assembly is most frequent and common. There are two types of microemulsions of which one is "direct" wherein the oil, which is the minor component, is dispersed in water, which is the major component, designated by o/w. The second type is "reverse" / "inverse" wherein water, which is the minor component, is dispersed in the oil, which is the major component, designated by w/o.
The term "Micelle" is known in the field. It particularly denotes an aggregate / shelf-assembly (Mn) of surfactant molecules (nM) dispersed in a liquid colloid, where M denotes a surfactant molecule, often referred to as surfactant monomer, Mn denotes a micelle due to aggregation of n surfactant monomers and n is number of surfactant molecule/monomers. It is also known that there are two types of micelles: (1) Direct / typical micelle, designated by o/w, and (2) reverse / inverse micelle, denoted by w/o. The term "Co-surfactant" is known in the field. It particularly denotes the substance that collaborates with surfactants in reducing interfacial tension. In context to the present invention, a co-surfactant is either a mono- or a poly-ol species.
The term "Micellar migration" is known in the field. It particularly denotes the exchange of surfactant monomers, solubilized ingredients and fragment of micelle (fragment of surfactant aggregate that comprises surfactant monomers, solubilized ingredients and co-surfactant molecules) among the micelles.
The term "liquid oral solution composition" is known in the field. It particularly denotes a mouthwash, mouth spray, gurgling rinse and mouth rinse.
In a first aspect, the invention relates to a liquid oral care composition, preferably in the form of a micro- emulsion, containing (i.e. comprising or consisting of) a) one or more non-ionic surfactants, preferably selected from the group consisting of polyoxyethylene sorbitan mono-esters of Ci2→i8 fatty acids;
b) one or more lipophilic excipients, preferably selected from flavoring oils;
c) one or more chlorine dioxide precursors, preferably
selected from the group consisting of alkali metal chlorites, - chlorates and - hypochlorites,
d) one or more phosphate compound selected from the group consisting of alkali pyrophosphate;
e) water
f) one or more sweeteners;
g) one or more isotonic agents.
It was surprisingly found that the inventive compositions have a shelf-life of 36 months or longer at room temperature, do not suffer from yellowing discoloration, do not suffer from denaturation of flavor and taste and do not develop undesirable chlorine odor. Further, the inventive compositions retain 80% of sodium chlorite at the length of 36 months. Further, the inventive compositions show a pronounced effect on oral hygiene and / or oral health,
particularly provide excellent results in controlling halitosis .
The invention is explained in further detail below:
Microemulsion: The inventive composition is typically present as an o/w microemulsion. In this microemulsion, the flavoring oils (constituent b) are in the micellar interior, surrounded by the surfactant (constituent a) . The remaining constituents are present in the continuous aqueous phase. Non-ionic surfactants produce relatively larger o/w micelles than ionic surfactants, which are more spacious towards accommodating greater amount of lipophilic substances and more efficient in wrapping up solubilized molecules in their lipophilic core. Migration of surfactant monomers, solubilized additives/ingredients and micellar fragments among ionic micelles exclusively occur via intermicellar migration involving (1) exit from one micelle, followed by (2) diffusion .in water phase and (3) association to another micelle. Migration mechanism involving intermicellar collisions (fusion-fission) is excluded due to strong repulsion potential amongst ionic micelles. Micellar collisions take place among the non- ionic micelles due to absence of intermicellar repulsive interaction. Intermicellar collision involves (1) temporary coalescence of two micelles during which exchange of surfactant monomers, solubilized additives and micellar fragments between the merged micelles take place, followed by (2) separation and re-formation. Micellar migration may take place for both ionic and non-ionic micelles via a third mechanism involving (1) loss of a micellar fragment that contains surfactant monomers, solubilized additives and co-surfactant, followed (2) diffusion in aqueous phase and (3) coagulation to other micelle. Solubilized additives are not embedded in such a fragment as good as in a full micelle, and therefore its diffusion through aqueous phase raises opportunity and probability of confrontation between
solubilized lipophilic ingredients and the ingredients soluble in the aqueous phase. Confrontation between aqueous phase containing precursors of C102 and solubilized lipophilic agents (flavor / fragrance in particular) in micelles is severely disadvantageous, since it will reduce the stability of the ingredients of the composition. If the micelles are too large, the probability of intermicellar collision and as a result permanent coalescence releasing solubilized oil phase, increases. Therefore, surfactants as defined below are preferred in the context of this invention .
Constituents: It is understood that each constituent a) to g) may be present as one single component (e.g. a single flavoring oil) or as a combination of components (e.g. two or more flavoring oils) . The constituents of the inventive composition are known per se (i.e. commercially available or available by known methods) although not combined as disclosed herein.
Constituent a) Non-ionic surfactants are known in the field. For the inventive compositions, pharmaceutically acceptable liquid non-ionic surfactants having a mean HLB number between 10 and 20, preferably between 14 and 19.5, more preferably between 15 and 19 are suitable. Such surfactants include Polysorbate 20-80, PEG-PPG-PEG block polymers having molecular weight ranging between 1000 and 6000, and PPG-PEG-PPG block polymers having molecular weight between 1000 and 4000. Preferred are polyoxyethylene sorbitan mono-esters of lauric acid (Polysorbate 20) , palmitic acid (Polysorbate 40) , stearic acid (Polysorbate 60) and oleic acid (Polysorbate 80) , respectively; such derivatives are known and commercially available (e.g. TEGO SML 20-80 supplied by Goldschmid and Tween 20-80 supplied by Croda) , such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 80. Also preferred are the above identified block polymers; such PEG-PPG-PEG and PPG-PEG-PPG
block polymer surfactants are known and commercially available as Pluronic (e.g. supplied by BASF) . One or more surfactants, preferably one surfactant, may be employed in the inventive composition, Particularly good results are obtained when using Polysorbate 20 (e.g. supplied by Goldschmid under the trade name, TEGO SML 20)
Suitable amounts of constituent a) are in the range of 15 - 30 wt.-%, preferably 18 - 22 wt.-%. The amount of surfactant used in the inventive composition is comparatively high. Without being bound to theory, it is believed that such high concentration improves stability of the composition and avoids the use of co-surfactants, as discussed below .
Constituent b) One or more lipophilic excipients, particularly flavoring oils, may be employed in the inventive composition. Advantageously, such flavoring oils are selected from the group consisting of Peppermint oil, Spearmint oil, Wintergreen oil, Eucalyptus oil. Particularly good results are obtained when said flavoring oils are extracted from leaves of the corresponding plants. Such oils are commercially available as "extra pure" (e.g. supplied by Essencia, Winterthur, Switzerland) . It was surprisingly found that flavoring oils of "extra pure" grade provided particularly good results. Without being bound to theory, it is believed that the absence of impurities in the flavoring oil stabilized the inventive composition, thereby providing an advantageous embodiment of the present invention. Suitable amounts of constituent b) are in the range of 0.2 - 8 wt.-%, preferably 0.5 - 5 wt.-%.
Constituent c) One or more water-soluble chlorine dioxide releasing agents ("chlorine dioxide precursors") may be employed in the inventive composition. Such chlorine dioxide releasing agents are known in the field and include
alkali metal chlorites, - chlorates and - hypochlorites, preferably alkali metal chlorites and - chlorates, particu¬ larly preferably sodium chlorite, potassium chlorite, sodium chlorate and potassium chlorate. Advantageously, sodium chlorite is used. Suitable amounts of constituent c) are in the range of 0.01 - 0.5 wt.-%, preferably 0.1 - 0.5 wt.-%, particularly preferably 0.2 - 0.35 wt-%.
Constituent d) One or more water-soluble phosphate com- pounds may be employed in the inventive composition. Phosphate compounds are commonly used to regulate the pH and / or to provide an anti - tartar effect. Suitable phosphate compounds or combinations thereof, are known in the field and include alkali metal pyrophosphate. Advanta- geously, tetrasodium pyrophosphate is used. Suitable amounts of constituent d) are in the range of 0.1 - 2 wt . - %, preferably 0.5 - 1 wt.-%.
Constituent e) The water employed may be any purity grade of water compliant with the intended use as an oral care product. Advantageously, de-ionized water is used. Suitable amounts of water are in the range of 60.05 - 84.5 wt.-%, preferably 70 - 80 wt.-%. Constituent f) One or more natural or artificial sweeteners may be added to the inventive composition. The addition of sweeteners is commonly done to improve consumer acceptance; any sweetener or combination of sweeteners known in the field may be used. Preferred are sweeteners that are stable towards oxidizing conditions and soluble in aqueous media, such as Acesulfame-K. Suitable amounts of constituent f) are in the range of 0 - 2 wt.-%, preferably 0.2 - 1 wt.-%.
Constituent g) One or more isotonic agents may be added to the inventive composition. The addition of isotonic agents is commonly done to improve osmotic diffusion through rending the osmotic pressure of the composition close to
that of oral mucosa; any isotonic agent or combination of isotonic agents known in the field may be used. It is understood that isotonic agents must be compatible with the intended use as oral care compositions, constituent g) may thus be more precisely defined as "oral isotonic agent" . Preferred are isotonic agents that are stable towards oxidizing conditions and soluble in aqueous media, such as NaCl. Suitable amounts of constituent g) are in the range of 0 - 1 wt.-%, preferably 0.05 - 0.5 wt.-%.
Suitable formulations of the inventive composition are any liquid formulations known in the field. In an advantageous embodiment, the invention thus relates to a composition as described herein, which is an oral care composition, particularly a mouth spray, mouth wash, mouth rinse, gurgling rinse and the like.
In one advantageous embodiment, the inventive composition is formulated as a mouth spray. Such formulations are suitable for cosmetic and therapeutic treatment, such as described below.
In a further advantageous embodiment, the inventive composition is formulated as a gurgling rinse. Such formulations are particularly suitable for the treatment of flu and bacterial infections to throat and larynx.
In an advantageous embodiment, the invention thus relates to an oral care composition as described herein, which is free of, or substantially free of co-surfactants . It was found that the inventive oral care composition is stable and transparent without addition of further co-surfactants. This is surprising considering the compositions disclosed in the prior art. Typically, co-surfactants, such as poly- oles or mono-alcohols, e.g. glycol or ethanol, are used to improve stability of oral care formulations.
In an advantageous embodiment, the invention thus relates to an oral care composition as described herein, wherein no additional bactericides and / or no preservatives are present .
In an advantageous embodiment, the invention thus relates to an oral care composition as described herein, having a pH between 7 and 11, preferably between 7.5 and 9.5, much preferred between 8 and 9.
In an advantageous embodiment, the invention relates to an oral care composition as described herein, having a viscosity similar to water; typically in the range between 2.5 10"4 and 1.5 10"3 Pas.
In a second aspect, the invention relates to the use of a compound or composition as described herein in cosmetic applications and / or therapeutic applications.
In one embodiment, the invention provides a composition as disclosed herein as pharmaceutical, particularly for the treatment, prevention and / or delay of progression of halitosis. The term "halitosis" is known in the field; it also includes oral malodor and bad breath. The compositions and methods of treatment of the present invention are particularly effective for treating or preventing halitosis. Halitosis may be caused from consumption of disadvantageous foods or drinks; from smoking. Halitosis may also be caused from high plaque count. Treatment may be effective irrespective of the underlying cause.
In one further embodiment, the invention provides composition as disclosed herein as pharmaceutical, particu larly for the treatment, prevention and / or delay o progression of diseases or conditions of the oral cavity The term "diseases or conditions of the oral cavity" i known in the field; it particularly denotes periodonta
disease, gingivitis, periodontitis, periodontosis, adult and juvenile periodontitis, and other inflammatory conditions of the tissues within the oral cavity, plus caries, necrotizing ulcerative gingivitis, and other conditions such as herpetic lesions, and infections that may develop following dental procedures such as osseous surgery, tooth extraction, periodontal flap surgery, dental implantation, and scaling and root planing. Also specifically included are dentoalveolar infections, dental abscesses (e.g., cellulitis of the jaw; osteomyelitis of the jaw), acute necrotizing ulcerative gingivitis (i.e., Vincent's infection), infectious stomatitis (i.e., acute inflammation of the buccal mucosa), and Noma (i.e., gangrenous stomatitis or cancrum oris) . Oral and dental infections are more fully disclosed in Finegold, Anaerobic Bacteria in Human Diseases, chapter 4, pp 78-104, and chapter 6, pp 115-154 (Academic Press, Inc., NY, 1977). The compositions and methods of treatment of the present invention are particularly effective for treating or preventing periodontal disease (gingivitis and/or periodontitis) and resulting breath malodor. Further, the term "diseases or conditions of the oral cavity" covers systemic and local causes; it thus includes underlying diseases, disorders or malfunctions, such as periodontal diseases and disorders; tongue and throat diseases associated infections, viral infections (such as influenza) , related bad-breath, shore throat problems, and bacterial infections to throat and larynx. Further, the term "disease or condition of the oral cavity" covers tooth whitening, tooth discoloration, tooth stain- ing, tooth decay and tooth hypersensitivity.
In one further embodiment, the invention provides the use of composition as disclosed herein for the treatment, prevention and / or delay of progression of halitosis and / or diseases or conditions of the oral cavity.
In one further embodiment, the invention provides the use of composition as disclosed herein for the manufacturing of a pharmaceutical for the treatment, prevention and or delay of progression of halitosis and / or diseases or conditions of the oral cavity.
In one further embodiment, the invention provides a method of treating halitosis and / or diseases or conditions of the oral cavity in a subject in need thereof comprising the step of contacting the oral cavity of said subject with an effective amount of a composition as described herein.
In one further embodiment, the invention provides the use of composition as disclosed herein for the cosmetic treatment of oral malodor.
In one further embodiment, the invention provides a method of cleaning the oral cavity of a subject in need thereof comprising the step of contacting the oral cavity with an effective amount of a composition as described herein.
The cosmetic and therapeutic effects of the composition as described herein are clearly different. While a cosmetic effect (such as treatment of halitosis) is directly achieved by one single application, a therapeutic effect (such as treatment of diseases of the oral cavity) is obtained by an application over a prolonged period, e.g. daily application over one week.
In a further advantageous embodiment, the cosmetic treatment comprises the step of applying once one or two doses of 0.1-1 ml, e.g. 0.25 ml, of the inventive composition.
In a further advantageous embodiment, the therapeutic treatment comprises the step of multiple applications of one or two doses of 0.1 - 1 ml, e.g. 0.25 ml, of a composition as described above. Such multiple applications include
applications once a day, twice a day, or 3 times a day over a period of 2 or more days, such as 2 days, 5 days, 1 week, 2 weeks, 1 month.
In a third aspect, the invention relates to the manufacture of compositions as described herein. The manufacturing of microemulsions is known in the field and generally comprises the combination of the required constituents at room temperature or elevated temperatures using standard equipment .
In one embodiment, the invention relates to a method for manufacturing composition as described herein, comprising the steps of
a) providing a phase A, in the form of a microemulsion, containing constituents a) , b) and water;
b) providing a phase B, in the form of a solution,
containing constituents c) , d) , f ) , g) and water c) combining said composition A and B to obtain a microemulsion .
In one embodiment, phase A is manufactured by providing a solution of constituents a) and b) and adding water to this solution under moderate agitation to obtain a microemulsion .
Depending on the constituents and the equipment used, manufacturing takes place at 15 - 85 °C, preferably at temperature .
The following examples further illustrate the invention without any limitation.
Manufacturing Process:
A mixer was charged with Polysorbate. The oils were added with moderate agitation until a clear solution / micro- emulsion was obtained. Water was added slowly to the
microemulsion with moderate agitation; the resulting mixture was agitated until a clear / transparent microemul¬ sion was obtained: phase A.
In a separate container, water soluble additives ("electro¬ lytes") were added to the water with moderate agitation and agitate until a clear aqueous solution was obtained: phase B.
Phase B was slowly added to phase A with high agitation. Agitation was continued until a transparent microemulsion was obtained.
Stability Test
The compositions of ex. 1 - 6 possess 36 months of shelf- life. In particular, the compositions of ex. 1 - 6
(1) did not show phase separation in 36 months of storage at room temperature as well as three months of storage at 40°C;
(2) retained 99.5%, 95% and 90% of C102 precursor in one, two and three years of storage at room temperature;
(3) retained 98%, 92% and 88% of C102 precursor in one, two and three years of storage at 40°C and
(4) no development of malodor, mal-taste and mal-flavor did occur in 36 months of storage in room temperature as well as three months storage in 40°C.
Clinical Test:
The compositions of ex. 1 - 6 are suitable as a mouthspray.
A composition according to ex. 1 was clinically tested on more than 100 volunteers of different age and sex groups with halitosis problem, using a halimeter. Clinical study furnishes (1) instant extinction of bad-breath with longer than 5 hours of after-effect, (2) reduction of halitosis problem upon systematic intake of the composition over between one and three weeks, and (3) an improvement in whiteness and brightness to the tooth has been observed through "Spectroshade" study on the volunteers upon systematic use of the composition for a week. In addition, Oxyguard II was tested out on the volunteers, with positive outcome, after consumption of foods and drinks, which are known to cause bad breath, such as garlic enriched foods, beers, vodka, etc. Furthermore, it has been tested on the volunteers suffering from Flu and shore-throat problems due to bacterial infections by means of gurgling and rinsing; while an immediate relief was noticed, it beneficially improved their health within 3 days of systematic intake.
Claims
1. A liquid oral care composition, in the form of a micro- emulsion, containing
a) 15 - 30 wt.-% non-ionic surfactants selected from the group consisting of polyoxyethylene sorbitan mono-esters of lauric acid, palmitic acid, stearic acid and oleic acid;
b) 0.2 - 8 wt.-% lipophilic excipients selected from the group consisting of Peppermint-, Spearmint-, intergreen-, Eucalyptus oil;
c) 0.01 - 0.5 wt.-% of a chlorine dioxide precursor, d) 0.1 - 2 wt.-l of a phosphate compound selected from the group consisting of alkali metal pyrophosphate; e) 65 - 85 wt.-% of water;
f) 0 - 2 wt.-% of a sweetener;
g) 0 - 1 wt.-l of an isotonic agent.
2. The composition according to claim 1, which is a mouth spray or gurgling rinse.
3. The composition according to any of claims 1 - 2,
wherein no Co-surfactants, particularly no alcohols, are present.
4. The composition according to any of claims 1 - 3,
wherein no additional bactericides and / or preservatives are present.
5. The composition according to any of claims 1 - 4,
having a pH between 7 and 11.
6. The composition according to any of claims 1 - 6,
wherein constituent a) is PEG 20 sorbitan monolaurate.
7. The composition according to any of claims 1 - 7,
wherein said flavoring oils are extracted from leaves.
8. The composition according to any of claims 1 - 7 wherein said chlorite precursor is potassium chlorite.
9. The composition according to any of claims 1 - 7
wherein said chlorite precursor is sodium chlorite.
10. The composition according to any of claims 1 - 9
wherein said phosphate compound is selected from the group consisting of tetrapotassium- and tetrasodium pyrophosphate .
11. The composition according to any of claims 1 - 10
wherein constituent e) is de-ionized water.
12. The composition according to any of claims 1 - 11
having a shelf life of 36 months or more, in particular wherein 88% of component c) are retained during storage for 36 months at 40°C.
13. A method for manufacturing an oral care composition according to any of claims 1-12, comprising the steps of a) providing a composition A a composition containing all ingredients of said oral care composition, except the calcium ion releaser, phosphate ion releaser and fluoride ion releaser (if present);
b) providing a composition B
c) combining said composition A and B to obtain a mi- croemulsion .
14. A Composition according to any of claims 1 - 12 for use as pharmaceutical.
15. A Composition according to any of claims 1 - 12 for the treatment, prevention and / or delay of progression of (i) disorders related to halitosis and (ii) of disorders or conditions of the oral cavity.
16. Use of a composition according to any of claims 1 - 12 a) for the treatment, prevention and / or delay of progression of disorders related to halitosis; or b) for the treatment, prevention and / or delay of
progression of diseases or conditions of the oral cavity; or
c) for the manufacturing of a pharmaceutical for the treatment, prevention and / or delay of progression of disorders related to halitosis; or
d) for the manufacturing of a pharmaceutical for the treatment, prevention and / or delay of progression of diseases or conditions of the oral cavity; or e) for the cosmetic treatment of halitosis.
17. A method of cleaning the oral cavity of a subject in need thereof, comprising the step of contacting the oral cavity with an effective amount of a composition according to any of claims 1 to 12.
18. A method of treatment, prevention and / or delay of progression of disorders related to halitosis of a subject in need thereof, comprising the step of contacting the oral cavity with an effective amount of a composition according to any of claims 1 to 12.
19. A method of treatment, prevention and / or delay of progression of diseases or conditions of the oral cavity in a subject in need thereof, comprising the step of contacting the oral cavity with an effective amount of a composition according to any of claims 1 to 12.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CH2010/000029 WO2011094872A1 (en) | 2010-02-03 | 2010-02-03 | Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients |
EP10702235.2A EP2531262B1 (en) | 2010-02-03 | 2010-02-03 | Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/CH2010/000029 WO2011094872A1 (en) | 2010-02-03 | 2010-02-03 | Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients |
Publications (1)
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WO2011094872A1 true WO2011094872A1 (en) | 2011-08-11 |
Family
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Family Applications (1)
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PCT/CH2010/000029 WO2011094872A1 (en) | 2010-02-03 | 2010-02-03 | Oral care composition comprising a precursor of chlorine dioxide and lipophilic excipients |
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WO (1) | WO2011094872A1 (en) |
Cited By (3)
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GB2499317A (en) * | 2012-02-10 | 2013-08-14 | Periproducts Ltd | Multicomponent oral care composition |
WO2015041523A1 (en) | 2013-09-18 | 2015-03-26 | Glymur B.V. | Oral hygiene compositions |
CN108697597B (en) * | 2016-02-29 | 2021-08-06 | 株式会社资生堂 | Cleansing cosmetic |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2499317A (en) * | 2012-02-10 | 2013-08-14 | Periproducts Ltd | Multicomponent oral care composition |
GB2499317B (en) * | 2012-02-10 | 2014-01-08 | Periproducts Ltd | Multicomponent oral care composition |
WO2013117913A3 (en) * | 2012-02-10 | 2014-07-03 | Periproducts Ltd | Multicomponent oral care composition |
US9211240B2 (en) | 2012-02-10 | 2015-12-15 | Periproducts Ltd | Multicomponent oral care composition |
US9408788B2 (en) | 2012-02-10 | 2016-08-09 | Periproducts Ltd | Multicomponent oral care composition |
EP3207934A1 (en) * | 2012-02-10 | 2017-08-23 | Periproducts Ltd | Multicomponent oral care composition |
WO2015041523A1 (en) | 2013-09-18 | 2015-03-26 | Glymur B.V. | Oral hygiene compositions |
CN108697597B (en) * | 2016-02-29 | 2021-08-06 | 株式会社资生堂 | Cleansing cosmetic |
Also Published As
Publication number | Publication date |
---|---|
EP2531262B1 (en) | 2016-05-25 |
EP2531262A1 (en) | 2012-12-12 |
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