|Publication number||US3431339 A|
|Publication date||Mar 4, 1969|
|Filing date||Jul 20, 1966|
|Priority date||Jul 20, 1966|
|Publication number||US 3431339 A, US 3431339A, US-A-3431339, US3431339 A, US3431339A|
|Inventors||Kenneth W Gyarmathy, Alexander W Bouchal|
|Original Assignee||Colgate Palmolive Co|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (4), Referenced by (55), Classifications (11)|
|External Links: USPTO, USPTO Assignment, Espacenet|
March 4, 1969 K. w. GYARMATHY ETAL 3,431,339
DENTIFRICES Filed July 20, 1966 INVENTORS. KENNETH WILLIAM GYARMATHY BY ALEXANDER WILLIAM BOUCHAL ATTORNEY United States Patent 3,431,339 DENTIFRICES Kenneth W. Gyarmathy, Old Bridge, and Alexander W.
Bouchal, Westfield, N.J., assignors to Colgate-Palmolive Company, New York, N.Y., a corporation of Delaware Filed July 20, 1966, Ser. No. 566,610
US. Cl. 42452 12 Claims Int. Cl. A61k 7/16 ABSTRACT OF THE DISCLOSURE Dental tablet for use in place of toothpaste. The tablet contains an intimate blend of water-soluble, anticaries fluorine containing agents, such as stannous fluoride or sodium monofluorophosphate, polishing agent, such as agent including insoluble sodium metaphosphate, foaming agent, such as sodium lauryl sulfate, and releasable matrix, such as waxy polyethylene glycol.
The present invention relates to dentifrices.
Toothpastes are, of course, the most commonly used dentifrices but, as generally employed, they do not ac complish as thorough a cleaning of the teeth as is desirable. One problem arises through carelessness in brushing, particularly a lack of thoroughness in brushing posterior teeth. This is the location where caries occur most frequently.
In addition, while toothpastes containing anticaries agents such as stannous fluoride have been widely used, it has been found that the activity of the added agent may diminish substantially on storage depending upon the particular formulation.
It is therefore an object of this invention to provide a dentifrice which promotes more thorough cleaning of the posterior teeth on brushing.
Another object of this invention is the provision of a dentifrice containing an anticaries agent which is resistant to loss of activity in the dentifrice on storage.
Other objects of this invention will be apparent from the following detailed description and claims. In this description and claims, all proportions are by weight unless otherwise indicated.
In accordance with one aspect of this invention, there is provided a unique compressed dental tablet for use, with a toothbrush, in place of toothpaste. The tablet, which contains an intimate blend of a water-soluble, anticaries fluorine containing agent, polishing agent, foaming agent and releasable matrix, has upper and lower convex surfaces, has a thickness at its thickest point of about 3 to 20 mm., has a Stokes hardness of about 2.5 to 6.0 kg. The size, shape and consistency of the tablet are such that it is readily crushed between the teeth and, when so crushed, breaks up to form simultaneously a multiple combination of (a) powdery material which is released to form with the saliva a slurry containing a nonpalpable polishing agent and which has the effect of a toothpaste slurry and (b) larger, palpable, gritty fragments of the tablet. The tablet has a pH of about 4.5-6.5 when slurried in water at 20% concentration. We have found that this substantially improves the cleaning of the lingual surfaces. Thus, in comparative tests, the use of the dental tablet of this invention gave a considerably better removal of plaques and debris from the lingual surfaces than was obtained by the use of toothpaste.
The tablet preferably has straight sides and has a length of about 8 mm. to 20 mm., a width of about mm. to 13 mm. and the maximum depth of the convexly curved top and bottom is preferably about to 25% of the tablet width. Advantageously it is oblong, most preferably oval. The preferred tablet will be oblong in shape so as to better fit between the posterior teeth when used.
A preferred form of tablet in accordance with this invention is illustrated in the drawing, in Which ITIGURE l is the top view of the tablet, drawn to sea e;
FIGURE 2 is a side view of the tablet, drawn to scale;
FIGURE 3 is a cross-sectional view taken along the line 3-3 of FIGURE 1;
FIGURE 4 is a view showing the tablet just before it is crushed between the teeth.
In accordance with this invention there is provided a crushable dental tablet containing a water-soluble, anticaries fluorine containing agent such as stannous fluoride, sodium monofluorophosphate or sodium fluoride in combonation with polishing agent, forming agent, a releasable matrix, all in a substantially anhydrous form. The amount of moisture in the tablet should preferably not exceed about 1%. We have found that the anticaries agent in such a dry tablet retains its effectiveness on storage for very long periods of time, in sharp contrast to the deterioration which takes place in toothpaste.
In a preferred embodiment of the invention, the tablet contains the anticaries fluorine containing agent, a stabilizer for the anticaries fluorine containing agent, a surface active foaming agent, a releasable matrix, and an agent to promote disintegration and a gelling agent together with a flavoring agent and an absorbent for the flavoring agent.
The preferred active anticaries ingredients are stannous fluoride and sodium monofluorophosphate, which are preferably supplied in finely divided form, e.g., having a particle size in the range of about 880 microns to 1,800 microns. This is considerably finer than the material conventionally employed in making toothpaste where a coarse agent, such as stannous fluoride, is dissolved in water. The amount of anticaries agent in the tablet may be varied but should provide an effective, nontoxic amount containing above 0.01% fluoride ppm.) per tablet. The maximum fluoride content of the tablet is typically about 1%. The preferred fluoride content is about 0.076 to 0.3%, say 0.1%. Thus stannous fluoride, when employed, would be typically in amount of about 0.04 to 4.1%, preferably about 0.3 to 1.24%, say 0.4%. Sodium monofluorophosphate, when employed, would be typically in amount of about 0.076 to 7.6%, preferably about 0.57 to 2.3%, say 0.76%. It is within the scope of this invention to use other active ingredients together with the anticaries fluorine-containing agent such as stannous fluoride or sodium monofluorophosphate. Examples of such ingredients are quaternary ammonium salts such as diisobutylphenoxyethoxyethyl dimethyl ammonium chloride. In addition urea may be employed in certain of the compositions when packaged in moisture retardant packages.
The preferred polishing agents are insoluble phosphate salts, most preferably the insoluble sodium metaphosphate which has been found to be compatible with Water-soluble, anticaries fluorine-containing agent. Other specific polishing agents include insoluble potassium metaphosphate, calcium pyrophosphate, magnesium orthophosphate, trimagnesium phosphate, tricalcium phosphate and dicalcium phosphate dihydrate, calcium carbonate, anhydrous dicalcium phosphate and alumina. It is also within the broader scope of the invention to employ other dental cleaning abrasives, which will not scratch the enamel surface of the teeth or abrade the dentin, such as calcium or magnesium carbonate, particularly when active ingredients other than fluorides are used in the tablet.
This invention permits the use of combinations of fluorides and polishing agents which heretofore were not used in toothpaste. Many polishing agents. contain calcium and cannot be used in fluoride containing toothpastes because the calcium reacts with the fluoride salt and reduces the available fluorine. Thus, where cost of polishing agent is of importance, it is possible to select the cheapest polishing agent for a far larger group of compounds and to use the polishing agent as a powder. The average particle size of the polishing agent may be the same as that usually employed for dentifrices, e.g., in the range of about 2 to 6 microns, preferably 3.5 to microns, with about 99.9% of the polishing agent passing a standard 200 mesh sieve which has openings about 0.074 mm. in diameter and well over 95%, typically 99%, passing a standard 325 mesh sieve (which has openings about 0.044 mm. in diameter). The amount of polishing agent in the composition is advantageously in the range of about to 95%, preferably about 50 to 85%.
Insoluble sodium metaphosphate often contains a soluble impurity, soluble sodium trimetaphosphate. In order to avoid certain undesirable effects of the sodium trimetaphosphate, it is preferable to include in the composition a material which inactivates or neutralizes this soluble impurity such as anhydrous dicalcium phosphate. Other suitable inactivators would be any of the slightly soluble magnesium or aluminum phosphates. A suitable proportion of the anhydrous dicalcium phosphate is up to about 5% by weight of the insoluble sodium metaphosphate.
The foaming agent in the composition may be any of those surface active agents employed as detergents and sudsing agents in dentifrices. Water-soluble sulfates of compounds having long chain alkyl radicals (e.g., chains of 10 to 18 carbon atoms) are suitable. One preferred material is a long chain fatty acid rnonoglyceride sulfate, such as the sodium salt of hydrogenated coco fatty acid rnonoglyceride sulfate used alone or in combination with sodium lauryl sulfate. Other suitable materials are the fatty acid amides of amino acids such as sodium N-lauroyl sarcosinate. The proportion of the detergent is advantageously in the range of about l-10%.
The releasable matrix in the composition is a binder which serves to unite the fine particles of the composition into a coherent mass when the composition is compressed as a tablet. A particularly suitable binder is a waxy polyethylene glycol, such as a polyethylene glycol of average weight of about 300 to 8,000, e.g. the products sold as Carbowax 6000 and Carbowax 4000. In the manufacture of the tablets we have found it highly advantageous to supply the binder ingredient in a finely divided solid condition, e.g., in the form of fine particles which will pass a US. Standard 80 mesh screen (which has openings about 0.177 mm. in diameter) and preferably a 100 mesh screen (which has openings about 0.149 mm. in diameter). Particularly good results have been obtained, in the manufacturing procedure, by bringing the fine binder particles into contact with the much more finely divided polishing agent before the substantial addition of the other ingredients of the composition. In place of the waxy polyethylene glycol, other waxy material such as tristearin, paraflin and the like may be used. The amount of binder is advantageously in the range of about 420% of the composition.
The preferred compositions of this invention also contain a small amount of a gelling or thickening agent which helps to produce a stronger foam on brushing. Suitable gelling agents are generally natural and synthetic gums and gumlike materials, such as sodium carboxymethyl cellulose, Irish Moss, gum tragacanth, gum acacia, gelatin, sodium alginate, methyl cellulose, polyvinyl-pyrroli done and the like. The proportion of gelling agent in the composition is advantageously in the range of up to about 2%.
The stability of the stannous fluoride in the composition may be enhanced by the inclusion of tetrasodium pyrophosphate, advantageously present in proportions in the range of about 0.1% to 0.4% based on the weight of the composition. Less preferably, other nontoxic sequestering agents may be employed together with, or in place of, the tetrasodium pyrophosphate.
The final disintegration of the tablet in the saliva is promoted by the presence of small amounts of starch, e.g., in amounts up to about 4%, that, about 0 to 4%, preferably about 2 to 3%, Arrowroot starch, corn starch, purified cellulose, olginic acid, methyl cellulose and the like are particularly suitable for this purpose.
Any suitable flavoring oils, e.g. menthol or oils of Spearmint, peppermint, Wintergreen or fruit flavors alone or in combination, may be used in the composition in amount suflicient to give the desired flavor, generally less than about 2%. The flavor oil is desirably absorbed on a finely divided flavor retainer. A preferred flavor retainer is very finely divided silica (e.g., having a particle size of under one micron, and a correspondingly large surface area). Other flavor retainers, known in the art, may also be used, e.g., the natural gums such as gum karaya and gum arabic. Microcrystalline cellulose has also given good results as a flavor retainer. The amount of flavor retainer to be used is in part dependent on the amount of flavoring agent in the composition; in general the amount of flavor retainer is about 0.5 to 3.0%.
To contribute desirable sweetness to the taste of the flavor, a sweetening agent such as sodium saccharin or sodium, potassium and calcium alts of cyclohexylsulf-amic acid is advantageously added in amounts up to about 0.67%.
It is advantageous to include a lubricant in the composition to aid in its processing in the tabletting machinery. Talc is excellent for this purpose. Magnesium and calcium stearate are also suitable. The proportion of lubricant is generally in the range of about 0.1 to 5% by Weight.
In the preferred compositions of this invention, mannitol is included. This ingredient aids in the disintegration of the table-t in the saliva of the mouth and improves the smoothness of the tablet during disintegration, thereby permitting the tablet to melt readily in the mouth. It also enhances the flavor and sweetness of the mixture. The amount of mannitol is advantageously in the range of up to 50% of the composition.
The inclusion of finely divided cellulose in the composition, in amounts up to about 10%, enhances the effect of the binder and also aids in the disintegration of the tablet in the saliva of the mouth. It also serves as a filler.
Suitable coloring agents may be incorporated in the mixture for esthetic effect. The moisture content of the tablet is desirably less than about 1%, e.g. about 0.5 to 1.0%. Preferably the tablet when made into a 20% solids slurry will have a pH of 5 .06.0.
In the manufacture of the tablet it is advantageous to first blend the insoluble powdered abrasives or polishing agents and the powdered releasable matrix binder in a powder mixer, than add the water soluble anticaries fluorine-containing powder together with the foaming agent, all in dry condition, to the mixer. A stabilizer for the anticaries agent and a gelling agent may also be blended together with the anticaries agent and the foaming agent. The flavoring agent, sweetener (e.g., saccharin) and flavor retainer may then be separately blended to form a dry powdery mass which is then blended thoroughly in the powder mixer with the previously mentioned mixed ingredients. The disintegrators and fillers, in dry, powdered condition, may then be incorporated. Prior to tabletting the powdered talc may be mixed thoroughly with the powder. The mixture is then fed to a suitable tablet press, such as a rotary tablet press, where it is compressed at a pressure high enough to produce a tablet of the desired hardness, generally about 350-l,400 kg./sq. cm. In the case of the preferred compositions, this pressure is about 1,125 kg./sq. cm.
In accordance with certain aspects of this invention, the preferred tablet contains a unit dosage for dental use, say about 500550 mg, typically about 520 mg.
EXAMPLE 1 The tablet was made up of the following composition.
Ingredients: Parts by weight Insoluble sodium metaphosphate (microcrystalline powder of food grade purity) 61.13 Anhydrous dicalcium phosphate (microcrystalline powder, food grade purity, meeting NFXI purity limits) 6 Polyethylene glycol having an average molecular weight of 6,000-7,500 (Carbowax 6000) 10 F.C. & C. Blue #1 Lake (Blue #1, 10%
precipitated on alumina substrate 0.017 F.D. & C. Violet #1 Lake (Violet #1, 10%
precipitated on alumina substrate) 0.017 Stannous fluoride 0.4 Tetrasodium pyrophosphate 0.4
Sodium salt of hydrogenated coco fatty acid monoglyceride sulfate 2 Sodium lauryl sulfate Sodium carboxymethylcellulose (CMC-7 MP) 1.25 Silica (particle size 0.015-0.020 micron, Cab- O-Sil M-S) 1.25 Flavoring oil Sodium saccharin 0.325 Finely divided woodpulp cellulose (Solka Floc BW 100) 5.475 Mannitol (Nil?) 5 Arrowroot starch 2.5 Alabama talc (U.S.P.) 2
The ingredients were blended in the manner previously described and compressed in a tabletting machine at a pressure of 1,125 kg./ sq. cm. to produce tablet slugs. The slugs were crushed through an 8-12 U.S. standard mesh screen (having openings 2.38-1.68 mm. in diameter) and the resulting granules were tab'letted at 1,125 kg./ sq. cm. to produce tablets having a Stokes hardness of 3-4.5 kgs. Each tablet had the doubly convex shape 4 illustrated in the drawing (which is drawn to scale) and was 0.127 cm. long and 0.0724 cm. wide and, at its thickest point, Was 0.0524 cm. thick. Each tablet had a circumferential straight-sides surface band (reference numeral 3) 0.0318 cm. in height, whose straight sides 4 were parallel to the short (thickness) axis of the tablet.
EXAMPLE 2 The tablet was made up of the following composition.
6 Ingredients: Parts by weight Tetrasodium pyrophosphate 0.4 Sodium salt of hydrogenated coco fatty acid monoglyceride sulfate 2 Sodium lauryl sulfate 0.5 Sodium carboxymethylcellulose (CMC-7 MP) 1.25 Silica (particle size 0015-0020 micron, Cab- O-Sil M-5) 1.25 Flavoring oil 1.75 Sodium saccharin 0.325 Finely divided woodpulp cellulose (Solka Floc BW 100) 5.475 Mannitol (N.F.) 5 Arrowroot starch 2.5 Alabama talc (-U.S.P.) 2
The tablets were made in the manner previously described by blending, compressing at 1,125 kg./sq. cn1., crushing, and tabletting at 1,125 kg/sq. cm. thereby obtaining tablets having a Stokes hardness of 3-4.5 'kgs. Each tablet had the doubly convex shape illustrated in the drawing (which is drawn to scale) and was 0.127 cm. long and 0.0724 cm. wide and, at its thickest point, was 0.0524 cm. thick. Each tablet had a circumferential straight-sides surface band (Reference numeral 3) 0.0318 cm. in height, whose straight sides were parallel to the short (thickness) axis of the tablet.
When the tablets of each of the examples are used, the average user naturally bites down on it with the posterior teeth, usually crushing the tablet between the .first molar and either a bicuspid or another molar. The
dentifrice then follows the usual food paths in and around the posterior teeth. The bits and pieces formed (together with powder) when the dentifrice is crushed make the user more apt (than when toothpaste is used) to clean away food debris that collects in the interproximals and along gingival margins. Because the user feels the presence of these particles he tends to continue brushing until the particles are removed. In this way the user is automatically encouraged to brush the buccal surfaces of posterior teeth and the lingual surfaces of all teeth, and thus to clean more thoroughly the areas where caries occur most frequently.
In addition, the fluoride-containing tablets of this invention have demonstrated much better retention of their content of active material on storage than fluoride-containing toothpaste.
Although the present invention has been described with reference to particular embodiments and examples, it will be apparent to those skilled in the art that variations and modifications of this invention can be made and that equivalents can be substituted therefor without departing from the principles and true spirit of the invention.
1. A dental tablet crushable with the teeth into powdery material containing a polishing agent and larger palpable, gritty fragments for use in the brushing of teeth with a toothbrush comprising an intimate blend of watersoluble, anticaries, fluorine-containing agent selected from the group consisting of stannous fluoride and sodium monofiuorophosphate in an amount to provide a fluorine content in said tablet of about 0.01% to 1% by weight, about 20% to 95% by weight of a polishing agent, about 1% to 10% by Weight of foaming agent, and about 4% g to 20% of waxy releasable matrix selected from the group consisting of a polyethylene glycol, tristearin and paraffin; said tablet having a moisture content up to about 0.01% to about 1% by weight, said tablet having upper and lower convex surfaces, a thickness at its thickest point of about 3 to 20 'mm. and a Stokes hardness of about 2.5 to 6.0 kgs.; said tablet having a pH of about 4.5 to 6.5 when slurried in water at 20% concentration.
2. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said tablet further comprises about 0.1% to 0.4% by weight of a stabilizer for said water-soluble anticaries containing agent, up to about 4% by weight of an agent to promote disintegration, up to about 2% by weight of a gelling agent, less than about 2% of a flavoring agent and about 0.5 to 3.0% of an absorbent for said flavoring agent.
3. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said watersoluble anticaries fluorine-containing compound is stannous fluoride.
4. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said waxy releasable matrix is a polyethylene glycol.
5. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said tablet has a length of about 8 mm. to 20 rnnr, a width of about 5 mm. to 13 mm. and the maximum depth of the convexly curved top and bottom is preferably about to 25% of the width of said tablet.
6. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said tablet contains a unit dosage for dental use and comprises about 0.49 to 0.55 mg. of fluorine provided by said watersoluble, anticaries fluorine-containing compound, about 331.6 to 366.5 :mg. of said polishing agent, about 12.35 to 13.65 mg. of said foaming agent and about 49.3 to 54.7 mg. of said releasable matrix.
7. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said fluorine content of said tablet is about 0.076 to 0.3% by weight.
8. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 7 wherein said watersoluble anticaries fluorine-containing compound is sodium monofluorophosphate.
9. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said polishing agent is a powdered insoluble phosphate salt having an average particle size of about 2 to 6 microns.
10. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 9 wherein said polishing agent comprises sodium metaphosphate and anhydrous dicalcium phosphate, said anhydrous dicalcium phosphate being present in amount up to 5% by weight of said sodium metaphosphate.
11. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 1 wherein said foaming agent is a surface active detergent.
12. A dental tablet for use in brushing of teeth with a toothbrush as claimed in claim 11 wherein said surface active detergent is selected from the group consisting of sodium N-lauroyl sarcosinate, sodium lauryl sulfate, and the sodium salt of hydrogenated coco fatty acid monoglyceride sulfate.
References Cited UNITED STATES PATENTS 834,676 10/1906 Luyties 16793 840,738 1/1907 Barnard 16793 3,116,208 12/1963 Emond 167-93 3,227,617 1/1966 Manahan et a1.
RICHARD L. H'UFF, Primary Examiner.
U.S. C1. X.R. 42457, 49
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,431,339 March 4, 1969 Kenneth W. Gyarmathy et a1.
It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:
In the heading to the printed specification, lines 3 and 4, "Kenneth W. Gyarmathy, Old Bridge, and Alexander W. Bouchal, Westfield, N. J." should read Kenneth William Gyarmathy, Old Bridge, and Alexander William Bouchal, Westfield, N. J.
Signed and sealed this 7th day of April 1970.
WILLIAM E. SCHUYLER, JR.
Commissioner of Patents Edward M. Fletcher, Jr.
|Cited Patent||Filing date||Publication date||Applicant||Title|
|US834676 *||Feb 23, 1906||Oct 30, 1906||Herman C G Luyties||Dentifrice.|
|US840738 *||May 11, 1906||Jan 8, 1907||Woodman Davis Company||Dentifrice.|
|US3116208 *||Nov 21, 1960||Dec 31, 1963||Sr Joseph S Emond||Dental cleanser in tablet form|
|US3227617 *||Mar 14, 1957||Jan 4, 1966||Colgate Palmolive Co||Fluoride dentifrice composition|
|Citing Patent||Filing date||Publication date||Applicant||Title|
|US3962417 *||Mar 27, 1974||Jun 8, 1976||Howell Charles J||Dentifrice|
|US4071614 *||Jan 9, 1976||Jan 31, 1978||Colgate Palmolive Company||Dentifrice containing encapsulated flavoring|
|US4157386 *||May 18, 1978||Jun 5, 1979||Rochelle Paul J||Soft, chewable lozenge forming a sticky coating on teeth when combined with saliva in the mouth which is removable only by brushing|
|US4169885 *||Mar 14, 1978||Oct 2, 1979||Blendax-Werke R. Schneider Gmbh & Co.||Dental and oral hygiene preparations|
|US4202878 *||Jun 22, 1978||May 13, 1980||The Procter & Gamble Company||Compositions of matter for coloring toothpaste and method of preparing same|
|US4203966 *||Dec 28, 1978||May 20, 1980||William F. McCord||Dentifrice with topical and systemic phosphate fluoride system|
|US4292306 *||Nov 8, 1979||Sep 29, 1981||Faunce Frank R||Dentifrice with topical and systemic phosphate fluoride system|
|US4308252 *||Oct 31, 1979||Dec 29, 1981||Young Dental Mfg. Co.||Dentifrice composition|
|US4367218 *||Oct 5, 1981||Jan 4, 1983||Jacobson Jerry I||Anti-caries oral rinse|
|US4411885 *||Mar 22, 1982||Oct 25, 1983||Barels Ronald R||Vitamin E oil based dentifrice|
|US4419341 *||Mar 4, 1983||Dec 6, 1983||Rizhsky Meditsinsky Institut||Drug for treatment of dental caries|
|US4419346 *||Aug 13, 1982||Dec 6, 1983||Nabisco Brands, Inc.||Method and composition to inhibit the growth of Streptococcus mutans by the use of saccharin/fluoride combination|
|US4515772 *||Mar 19, 1984||May 7, 1985||The Procter & Gamble Company||Oral compositions|
|US4624849 *||Nov 2, 1984||Nov 25, 1986||The Procter & Gamble Company||Antimicrobial lozenges|
|US4753792 *||Nov 10, 1986||Jun 28, 1988||Aberg T||Tooth cleaning tablet|
|US4806339 *||Jun 9, 1987||Feb 21, 1989||The Procter & Gamble Company||Oral compositions|
|US4859467 *||Sep 25, 1986||Aug 22, 1989||Colgate-Palmotive Company||Sustained release fluoride composition|
|US4861590 *||Sep 25, 1986||Aug 29, 1989||Colgate-Palmolive Company||Sustained release fluoride and calcium composition|
|US4885155 *||Feb 8, 1989||Dec 5, 1989||The Procter & Gamble Company||Anticalculus compositions using pyrophosphate salt|
|US4950479 *||Nov 6, 1986||Aug 21, 1990||Hill Ira D||Method of interrupting the formation of plaque|
|US4999184 *||Oct 4, 1989||Mar 12, 1991||The Procter & Gamble Company||Oral compositions|
|US5032387 *||Nov 6, 1986||Jul 16, 1991||Princeton Pharmaceutical Inc.||Dental and oral hygiene preparations|
|US5057305 *||Jan 22, 1988||Oct 15, 1991||Dentab, Inc.||Tooth cleaning tablet|
|US5057306 *||Jun 8, 1990||Oct 15, 1991||Hill Ira D||Method of manufacturing oral hygiene gels|
|US5057307 *||Jun 8, 1990||Oct 15, 1991||Hill Ira D||Method of relieving gum discomfort|
|US5057308 *||Jun 8, 1990||Oct 15, 1991||Hill Ira D||Method of treating the oral cavity with oral hygiene preparations containing active SnF2|
|US5057309 *||Jun 8, 1990||Oct 15, 1991||Hill Ira D||Oral hygiene preparations|
|US5098711 *||Dec 20, 1989||Mar 24, 1992||Ira Hill||Method of treating the oral cavity with dental floss containing chemotherapeutic agents|
|US5143720 *||Nov 28, 1990||Sep 1, 1992||Microcide, Inc.||Disinfecting and sanitizing compositions|
|US5158764 *||Oct 9, 1991||Oct 27, 1992||Degussa||Dentifrice|
|US5165913 *||Aug 29, 1991||Nov 24, 1992||Ira Hill||Controlled release interproximal delivery system|
|US5280042 *||May 26, 1992||Jan 18, 1994||Microcide, Inc.||Disinfecting and sanitizing compositions|
|US5804165 *||Jul 24, 1996||Sep 8, 1998||Arnold; Michael J.||Antiplaque oral composition|
|US5965110 *||Jul 10, 1998||Oct 12, 1999||Arnold; Michael J.||Plaque adsorbent oral composition and method|
|US6235318||Jan 21, 1999||May 22, 2001||Charles M. Lombardy, Jr.||Effervescent chewing gum|
|US6471991||Jun 13, 2001||Oct 29, 2002||Mcneil-Ppc, Inc.||Soft chewable tablets having convexed shaped face surfaces|
|US7029699||Aug 22, 2002||Apr 18, 2006||Robinson Ronni L||Soft chewable tablets|
|US7074390||Mar 6, 2003||Jul 11, 2006||Mackinnon Carol L||Encapsulated dentifrice and method of use|
|US7287643 *||Jan 21, 2005||Oct 30, 2007||Glover Sr Larry D||Tooth care device, kit and method of use|
|US8192724 *||Nov 2, 2005||Jun 5, 2012||Tower Laboratories, Ltd.||Oral care tablet|
|US20030049316 *||Aug 22, 2002||Mar 13, 2003||Robinson Ronni L.||Soft chewable tablets|
|US20040101493 *||Nov 12, 2003||May 27, 2004||Scott Douglas Craig||Chewable solid unit dosage forms and methods for delivery of active agents into occlusal surfaces of teeth|
|US20040101494 *||Nov 12, 2003||May 27, 2004||Scott Douglas Craig||Chewable solid unit dosage forms and methods for delivery of active agents into occlusal surfaces of teeth|
|US20040175334 *||Mar 6, 2003||Sep 9, 2004||Mackinnon Carol L.||Encapsulated dentifrice and method of use|
|US20040223921 *||May 7, 2003||Nov 11, 2004||Rau Allen H.||Oral care tablet|
|US20060057078 *||Nov 2, 2005||Mar 16, 2006||Rau Allen H||Oral care tablet|
|US20070071817 *||Sep 26, 2005||Mar 29, 2007||Phyzz, Inc.||Effervescent oral care compositions and method of use|
|DE4109518A1 *||Mar 22, 1991||Sep 26, 1991||Yoshimi Adachi||Individual dentifrice supply for direct oral delivery - from water soluble or frangible capsule, ensures use of correct amt. of dentifrice|
|EP0997143A2 *||Aug 17, 1999||May 3, 2000||McNEIL-PPC, INC.||Soft chewable tablets|
|EP0997143A3 *||Aug 17, 1999||Nov 14, 2001||McNEIL-PPC, INC.||Soft chewable tablets|
|WO1988010110A1 *||Jun 22, 1988||Dec 29, 1988||Dentab, Inc.||A tooth cleaning and fluoridating tablet|
|WO1997019668A2 *||Nov 26, 1996||Jun 5, 1997||Tame Said Jorge Isaac||Toothpaste and mouthwash in tablets|
|WO1997019668A3 *||Nov 26, 1996||Jul 24, 1997||Tame Said Jorge Isaac||Toothpaste and mouthwash in tablets|
|WO1999033437A1 *||Dec 29, 1997||Jul 8, 1999||The Procter & Gamble Company||Tooth cleaning composition in tablet form|
|WO2016156161A1||Mar 23, 2016||Oct 6, 2016||Unilever Plc||Solid oral care compositions|
|U.S. Classification||424/52, 424/57, 424/49|
|International Classification||A61K8/21, A61Q11/00|
|Cooperative Classification||A61Q11/00, A61K8/0216, A61K8/21|
|European Classification||A61K8/02M, A61Q11/00, A61K8/21|