CA1190150A - Alkali metal salts of poly(vinylbenzoic acid) as dental plaque barrier agents - Google Patents
Alkali metal salts of poly(vinylbenzoic acid) as dental plaque barrier agentsInfo
- Publication number
- CA1190150A CA1190150A CA000413631A CA413631A CA1190150A CA 1190150 A CA1190150 A CA 1190150A CA 000413631 A CA000413631 A CA 000413631A CA 413631 A CA413631 A CA 413631A CA 1190150 A CA1190150 A CA 1190150A
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- CA
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- Prior art keywords
- poly
- plaque
- alkali metal
- vinylbenzoic acid
- dental plaque
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
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Abstract
ALKALI METAL SALTS OF POLY(VINYLBENZOIC ACID) AS DENTAL
PLAQUE BARRIER AGENTS
ABSTRACT OF DISCLOSURE
Compositions and methods for preventing the attachment of dental plaque to the surfaces of the teeth of mammals comprises certain alkali metal salts of poly(vinylbenzoic acid) in pharmaceutically acceptable vehicles, and the periodic applications thereof to teeth.
PLAQUE BARRIER AGENTS
ABSTRACT OF DISCLOSURE
Compositions and methods for preventing the attachment of dental plaque to the surfaces of the teeth of mammals comprises certain alkali metal salts of poly(vinylbenzoic acid) in pharmaceutically acceptable vehicles, and the periodic applications thereof to teeth.
Description
~LKALI MET~L SALTS OF POLY(VIN~LBE~JZOIC ACID) AS DENTAL
PLAQUE BARRIER AGENTS
Technical Field This invention relates to oral hygiene compositions and methods using such compositions to prevent attachment of bacteria to teeth~ More particularly it relates to certain alkali metal salts oE poly(vinylbenzoic acid) that have been found useful in inhibiting the agglutination of oral microbes on teeth.
Background Art The prevention of the deposition of dental plaque on teeth is a highly desired resultO Dental plaque results when cariogenic bacteria aggregate in colonies on the surface of teeth and form a tenacious deposit thereon. The pre-sence of plaque on teeth is believed to be a precursor to development of gingivitis, dental caries and periodontal disease.
While many attempts have been made to control the effects of cariogenic bacteria and the dental plaque they produce, for example, fluoride, flossing, brushing, etc., treat-ments, these are typically directed to either counteract-ing the secondary effects of plaque on the teeth and gums, or to the removal of plaque that is already formed on and adhering to the teeth and surrounding tissue. Such treat-ments are not, however, entirel~ successful, and must be supplemented with periodic treatment by dental profes-sionals. To date, there is no commercially feasible home treatment method for preventing the formation of plaque or its adhesion to teeth.
J&J 1023 V~(3 The Invention Certain alkali metal salts of poly(vinylbenzoic acid) have been found to inhibit the deposition of dental plaque onto human teeth when applied from various dentifrice formula-tions, mouth rinses, or other oral hygiene procedures.These hydrophilic polymers are substantially soluble in water or water/organic solvent vehicles and have good film forming characteristics. While the mechanism of action of the hydrophilic polymeric films in retarding plaque deposition is not known with absolute certainty, it is presumed that the films of anionically-charged polymers deposited on teeth effect a mutual repulsion between the negatively charged polymer film and the negatively charged microorganisms responsible for plaque generation. The polymeric salts of this invention are especially effective as components of dentifrices and other oral hygiene pre-parations in reducing dental plaque deposition on teeth.
The hydrophilic, polymeric salts found useful for dental plaque control in accordance with the present invention are essentially alkali metal salts of the homopolymers of vinylbenzoic acid, wherein the repeating unit of the polymer is represented by structure (A), ~ c~ C~
(~) where M is selected from the group consisting of sodium, potassium, and lithium.
The poly(vinylbenzoic acid) polymers required as interme-diates for the preparation of the salts of structure (A) are readily prepared by the free radical polymerization of vinylbenzoic acid monomers, typified by the ~-vinylbenzoic acid available from Pfaltz and Bauer. Neutralization of the poly(vinylbenzoic acid) polymers with alkali metal J&J 1023 v hydroxides, or addition of at least stoichiometric quanti-~ies of an alkali metal o~ide, carbonate, chloride, nitrate, acetate, or sulfate, suffices to produce the polymeric salts of this invention. If desired, the S aqueous solutions of the polymeric salts can be purified by dialysis and the dialyzed polymer solution freeze-dried, spray-dried, or evaporated to afford the polymeric salts in ~he solid form.
The alkali metal salts of the poly(vinylbenzoic acid) pol~mers of this invention are highly effective in reduc-ing the deposition of pla~ue during 1n vitro testing. For example, sodium poly(4-vinylbenzoate) prepared from poly-(4-vinylbenzoic acid) exhibited a 91% reduction in the deposition o~ plaque when tested. The in vitro test pro-cedure employed begins with growth of plaque in small jars containing sterilized trypticase media that has been supplemented with sucrose. T~pically, ten jars are individually inoculated with 0.5 ml of unpooled freshly collected human plaque from 10 subjectsO In a control series, a presterilized glass slide or an extracted human tooth is inserted into each jar. In the test series, the tooth or glass slide is pretrea-ted with a 1% solution of the test compound (dissolved in water or other vehicle), allowed to dry in order to deposit a thin film of the compound on the surface, and the glass slide or tooth placed in the growth media. The jars are incubated under anaerobic conditions for two days at 37C. The tooth or glass slide is removed, air dried, and stained with 0.15%
FD&C #3 red dye solution to reveal the accumulated plaque deposits. The tooth or glass slide is scored for plaque density on a 0 to 5 scale. Plaque barrier activity is reported as the % of average plaque reduction, as compared to appropriate controls for ten subjects.
J&J 1~23 ~9~)~5(~
Example 1 Sodium poly(~-vinylbenzoate) suspension of 4.0 g (0.027 mole) 4-vinylbenzoic aci~ and 0.0~ g azobisisobutyronitrile in 25 ml. benzene was heated under nitro~en at 80C. for about 8 hours, during which time heavy precipitation of polymer took place. The suspension was cooled to room temperature, diluted with 25 ml. benzene, and filtered to give 4.0 g of poly(4-vinylbenzoic acid).
A solution of 1.663~ g of the poly (4-vinylbenzoic acid) in 30 ml. methanol was adjusted from pH 2.5 to pH 11.0 with 23~3 ml. 0.480 N methanolic sodium hydroxide. The resultant solution was solvent stripped to white solids of sodium poly(4~vinylbenæoate). The NMR and IR spectra were consistent with the structure of the polymeric salt.
The plaque barrier oral compositions of this invention may comprise any conventional pharmaceutically acceptable oral hygiene formulation that contains (and is compatible with) an effective amount of a plaque barrier agent as defined herein. Such formulations include, for example, mouth-washes, rinses, irrigating solutions, nonabrasive gel dentifrices, denture cleansers, coated dental floss and interdental stimulator coatings, chewing gums, lozenges, breath fresheners, foams and sprays.
The plaque barrier agents may be present in these formula-tions in effective concentrations generally in the range 30 of from about 0.05 weight percent to as much as 30 weight percent or the limit of compatibility with the vehicle.
However, no advantage will be derived from concentrations in excess of about 20 weight percent. A preferred concen-tration range for the plaque barrier agents in the formu-35 lations of the invention i5 from about 0.5 to about 10 weight percent. A more preferred range is from about 2 to J~J 1023 5~3 a~out 8 percent by weigh-t, about 5% ~eing the presently most preferred concentration in a nonabrasive yel ve-hicle.
The pH of these plaque barrier preparations should be between pH 5.0 and 10.0, preferably between pH 5.0 and 8.0, more preferably between about p~ 6.0 and 7.5.
Lower pH than 5.0 is undesirable because of the possi-ble enhancement of enamel demineralization.
Suitable conventional pharmaceutically acceptable ve-hicles that can be employed with the plaque barrier agents to prepare the barrier compositions of this invention may comprise water, ethanol, such humectants as polypropylene glycol, glycerol and sorbitol, such gelling agents as cellulose derivatives, for example, METHOCE~*, carboxymethylcellulose (CMC 7MF) and KLUCEL*
HF, polyoxypropylene~polyoxyethylene block copolymers, for example, PLURO~IC* F-127, PLURONIC F-108, PLURONIC
P-103, PLURONIC P-104, PLURO~IC P-105, and PLURO~IC
P-123, colloidial magnesium aluminosilicate complexes such as V~EGUM*, and mucoprotein thickening agents such as CARBOPOL* 934, gel stabilizers such as the silicon dioxides, for example, CAB-O-SIL* M5 and poly-vinylpyrrolidone, sweeteners such as sodium saccharin preservatives such as citric acid, sodium benzoate, cetylpyrridinium chloride, potassium sorbate, methyl and ethyl parabens, detergents such as sodium lauryl sulfate, sodium cocomonoglyceride sulfonate, sodium lauryl sarcosinate and polyoxyethylene isohexadecyl ether (ARLASOLVE* 200) and approved colors and flavors.
Anticaries fluoride compounds, such as sodium fluoride, can also be incorporated into the compositions of this invention.
The following specific examples will serve further to illustrate the plaque barrier compositions of this invention.
*Trade mark 3(31~
EXAMPLE A - Mouthwash Solution Barrier Agent 0.5-2.0 ~ w/w Glycerol (humectant) 6.0 Pluronic F 108 1.0 Sodium saccharin (sweetener) 0.3 Deionized Water q~s.
Flavors 1.0 EXAMPLE B - Mouthwash Solution Plaque Barrier Agent0.5-3.0 % w/w Ethanol, USP 15.0 Pluronic F-108 (foaming agent) 2.0 Glycerol (humectant)10.0 Sorbitol (humectant)10.0 Sodium saccharin (sweetener) 0.2 Deionized Water q.s.
Flavors o.z 100 .0 EXAMPLE C - Abrasive Dentrifice Gel Plaque Barrier Agent2.0-10.0 % w/w Fumed Silica (abrasive) 55.0 Sodium Lauryl Sulfate (detergen~) 1.5 Glycerol (humectant) 10.0 Carboxymethylcellulose (gelling agent) 2.0 Sodium saccharin (sweetener)0.2 Sorbitol (humectant) 10.0 E`lavors 1.0 Deionized Water q.s.
Preservative 0.05 100 .0 Jh J 1023 3~
EXAMPLE D Chewlng Gum Plaque Barrier Agent 1.0-11.0% w/w Gum Base 21.3 Sugar 48.5-58.5 Corn 5yrup (Baume 45)18.2 Flavors 1.0 100 . O
EXAMPLE ~ - Nonabrasive Gel Dentifrice 10 Plaque Barrier Agent 0.05-30.0% w/w Sorbistat (preservative) 0.15 Deionized Water q.s.
Silicon Dioxide (gel stabilizer) 1.0 Pluronic F 127 (gelling agen-t~ 20,0 Sodium Saccharin 0.2 Flavors 1.5 100 .0 Example F
The following formulation illustrates a presently preferred nonabrasive gel composition containing a barrier agent in accordance with the present invention.
Ingredients % w/w Distilled Water q.s.
Sodium Saccharin (sweetener) 0.20 Sodium Benzoate (preservative) 0.30 FD~C ~lue #1 (0.1%aq. soln.) 0.27 D&C Yellow ~10 (0.5~ aq. soln.) 0.50 Gelling agent 18.00 Glycerol (Humectant) 2Q.00 Cab-O-Sil M5 (Silicon Dioxide) 1.00 Plaque Barrier Agent 5.00 (dry basis) Flavor 0.80 100 .0 J&J 10~3 3~5~
.~
While the details of preparing all of the above formula-tions are well within the skill of the art, a suggested procedure for preparing the gel formulation of this example will be described for completeness.
In a first container the water, sodium saccharin, sodium benzoate and dyes are mixed. Then the container is put into an ice bath. When the temperature reaches 6C, the gelling agent is added and the contents mixed slowly until the gelling agent is dissolved. Then the solution is heated to 70C.
Into a second container is added the glycerin. Then the Cab~O-Sil M5 is sprinkled in with mixing. Then the plaque barrier agent is added and mixing continued to a smooth paste. The paste is then heated in a water bath with mixing to a temperature of 70C.
The contents of the first container are added to the second container and blended together until the batch is homogenous while maintaining a 70C temperature. Then the flavoring is added, all mixing is stopped, and the formu-lation allowed to settle for approximately one hour. If necessary to remove air bubbles, overnight refrigeration may be employed.
These compositions are preferably employed from one to three times daily in a routine oral hygiene program to prevent the attachment of plaque to the teeth.
Variations can, of course, be made without departing from the spirit or scope of the invention.
J&J 1023
PLAQUE BARRIER AGENTS
Technical Field This invention relates to oral hygiene compositions and methods using such compositions to prevent attachment of bacteria to teeth~ More particularly it relates to certain alkali metal salts oE poly(vinylbenzoic acid) that have been found useful in inhibiting the agglutination of oral microbes on teeth.
Background Art The prevention of the deposition of dental plaque on teeth is a highly desired resultO Dental plaque results when cariogenic bacteria aggregate in colonies on the surface of teeth and form a tenacious deposit thereon. The pre-sence of plaque on teeth is believed to be a precursor to development of gingivitis, dental caries and periodontal disease.
While many attempts have been made to control the effects of cariogenic bacteria and the dental plaque they produce, for example, fluoride, flossing, brushing, etc., treat-ments, these are typically directed to either counteract-ing the secondary effects of plaque on the teeth and gums, or to the removal of plaque that is already formed on and adhering to the teeth and surrounding tissue. Such treat-ments are not, however, entirel~ successful, and must be supplemented with periodic treatment by dental profes-sionals. To date, there is no commercially feasible home treatment method for preventing the formation of plaque or its adhesion to teeth.
J&J 1023 V~(3 The Invention Certain alkali metal salts of poly(vinylbenzoic acid) have been found to inhibit the deposition of dental plaque onto human teeth when applied from various dentifrice formula-tions, mouth rinses, or other oral hygiene procedures.These hydrophilic polymers are substantially soluble in water or water/organic solvent vehicles and have good film forming characteristics. While the mechanism of action of the hydrophilic polymeric films in retarding plaque deposition is not known with absolute certainty, it is presumed that the films of anionically-charged polymers deposited on teeth effect a mutual repulsion between the negatively charged polymer film and the negatively charged microorganisms responsible for plaque generation. The polymeric salts of this invention are especially effective as components of dentifrices and other oral hygiene pre-parations in reducing dental plaque deposition on teeth.
The hydrophilic, polymeric salts found useful for dental plaque control in accordance with the present invention are essentially alkali metal salts of the homopolymers of vinylbenzoic acid, wherein the repeating unit of the polymer is represented by structure (A), ~ c~ C~
(~) where M is selected from the group consisting of sodium, potassium, and lithium.
The poly(vinylbenzoic acid) polymers required as interme-diates for the preparation of the salts of structure (A) are readily prepared by the free radical polymerization of vinylbenzoic acid monomers, typified by the ~-vinylbenzoic acid available from Pfaltz and Bauer. Neutralization of the poly(vinylbenzoic acid) polymers with alkali metal J&J 1023 v hydroxides, or addition of at least stoichiometric quanti-~ies of an alkali metal o~ide, carbonate, chloride, nitrate, acetate, or sulfate, suffices to produce the polymeric salts of this invention. If desired, the S aqueous solutions of the polymeric salts can be purified by dialysis and the dialyzed polymer solution freeze-dried, spray-dried, or evaporated to afford the polymeric salts in ~he solid form.
The alkali metal salts of the poly(vinylbenzoic acid) pol~mers of this invention are highly effective in reduc-ing the deposition of pla~ue during 1n vitro testing. For example, sodium poly(4-vinylbenzoate) prepared from poly-(4-vinylbenzoic acid) exhibited a 91% reduction in the deposition o~ plaque when tested. The in vitro test pro-cedure employed begins with growth of plaque in small jars containing sterilized trypticase media that has been supplemented with sucrose. T~pically, ten jars are individually inoculated with 0.5 ml of unpooled freshly collected human plaque from 10 subjectsO In a control series, a presterilized glass slide or an extracted human tooth is inserted into each jar. In the test series, the tooth or glass slide is pretrea-ted with a 1% solution of the test compound (dissolved in water or other vehicle), allowed to dry in order to deposit a thin film of the compound on the surface, and the glass slide or tooth placed in the growth media. The jars are incubated under anaerobic conditions for two days at 37C. The tooth or glass slide is removed, air dried, and stained with 0.15%
FD&C #3 red dye solution to reveal the accumulated plaque deposits. The tooth or glass slide is scored for plaque density on a 0 to 5 scale. Plaque barrier activity is reported as the % of average plaque reduction, as compared to appropriate controls for ten subjects.
J&J 1~23 ~9~)~5(~
Example 1 Sodium poly(~-vinylbenzoate) suspension of 4.0 g (0.027 mole) 4-vinylbenzoic aci~ and 0.0~ g azobisisobutyronitrile in 25 ml. benzene was heated under nitro~en at 80C. for about 8 hours, during which time heavy precipitation of polymer took place. The suspension was cooled to room temperature, diluted with 25 ml. benzene, and filtered to give 4.0 g of poly(4-vinylbenzoic acid).
A solution of 1.663~ g of the poly (4-vinylbenzoic acid) in 30 ml. methanol was adjusted from pH 2.5 to pH 11.0 with 23~3 ml. 0.480 N methanolic sodium hydroxide. The resultant solution was solvent stripped to white solids of sodium poly(4~vinylbenæoate). The NMR and IR spectra were consistent with the structure of the polymeric salt.
The plaque barrier oral compositions of this invention may comprise any conventional pharmaceutically acceptable oral hygiene formulation that contains (and is compatible with) an effective amount of a plaque barrier agent as defined herein. Such formulations include, for example, mouth-washes, rinses, irrigating solutions, nonabrasive gel dentifrices, denture cleansers, coated dental floss and interdental stimulator coatings, chewing gums, lozenges, breath fresheners, foams and sprays.
The plaque barrier agents may be present in these formula-tions in effective concentrations generally in the range 30 of from about 0.05 weight percent to as much as 30 weight percent or the limit of compatibility with the vehicle.
However, no advantage will be derived from concentrations in excess of about 20 weight percent. A preferred concen-tration range for the plaque barrier agents in the formu-35 lations of the invention i5 from about 0.5 to about 10 weight percent. A more preferred range is from about 2 to J~J 1023 5~3 a~out 8 percent by weigh-t, about 5% ~eing the presently most preferred concentration in a nonabrasive yel ve-hicle.
The pH of these plaque barrier preparations should be between pH 5.0 and 10.0, preferably between pH 5.0 and 8.0, more preferably between about p~ 6.0 and 7.5.
Lower pH than 5.0 is undesirable because of the possi-ble enhancement of enamel demineralization.
Suitable conventional pharmaceutically acceptable ve-hicles that can be employed with the plaque barrier agents to prepare the barrier compositions of this invention may comprise water, ethanol, such humectants as polypropylene glycol, glycerol and sorbitol, such gelling agents as cellulose derivatives, for example, METHOCE~*, carboxymethylcellulose (CMC 7MF) and KLUCEL*
HF, polyoxypropylene~polyoxyethylene block copolymers, for example, PLURO~IC* F-127, PLURONIC F-108, PLURONIC
P-103, PLURONIC P-104, PLURO~IC P-105, and PLURO~IC
P-123, colloidial magnesium aluminosilicate complexes such as V~EGUM*, and mucoprotein thickening agents such as CARBOPOL* 934, gel stabilizers such as the silicon dioxides, for example, CAB-O-SIL* M5 and poly-vinylpyrrolidone, sweeteners such as sodium saccharin preservatives such as citric acid, sodium benzoate, cetylpyrridinium chloride, potassium sorbate, methyl and ethyl parabens, detergents such as sodium lauryl sulfate, sodium cocomonoglyceride sulfonate, sodium lauryl sarcosinate and polyoxyethylene isohexadecyl ether (ARLASOLVE* 200) and approved colors and flavors.
Anticaries fluoride compounds, such as sodium fluoride, can also be incorporated into the compositions of this invention.
The following specific examples will serve further to illustrate the plaque barrier compositions of this invention.
*Trade mark 3(31~
EXAMPLE A - Mouthwash Solution Barrier Agent 0.5-2.0 ~ w/w Glycerol (humectant) 6.0 Pluronic F 108 1.0 Sodium saccharin (sweetener) 0.3 Deionized Water q~s.
Flavors 1.0 EXAMPLE B - Mouthwash Solution Plaque Barrier Agent0.5-3.0 % w/w Ethanol, USP 15.0 Pluronic F-108 (foaming agent) 2.0 Glycerol (humectant)10.0 Sorbitol (humectant)10.0 Sodium saccharin (sweetener) 0.2 Deionized Water q.s.
Flavors o.z 100 .0 EXAMPLE C - Abrasive Dentrifice Gel Plaque Barrier Agent2.0-10.0 % w/w Fumed Silica (abrasive) 55.0 Sodium Lauryl Sulfate (detergen~) 1.5 Glycerol (humectant) 10.0 Carboxymethylcellulose (gelling agent) 2.0 Sodium saccharin (sweetener)0.2 Sorbitol (humectant) 10.0 E`lavors 1.0 Deionized Water q.s.
Preservative 0.05 100 .0 Jh J 1023 3~
EXAMPLE D Chewlng Gum Plaque Barrier Agent 1.0-11.0% w/w Gum Base 21.3 Sugar 48.5-58.5 Corn 5yrup (Baume 45)18.2 Flavors 1.0 100 . O
EXAMPLE ~ - Nonabrasive Gel Dentifrice 10 Plaque Barrier Agent 0.05-30.0% w/w Sorbistat (preservative) 0.15 Deionized Water q.s.
Silicon Dioxide (gel stabilizer) 1.0 Pluronic F 127 (gelling agen-t~ 20,0 Sodium Saccharin 0.2 Flavors 1.5 100 .0 Example F
The following formulation illustrates a presently preferred nonabrasive gel composition containing a barrier agent in accordance with the present invention.
Ingredients % w/w Distilled Water q.s.
Sodium Saccharin (sweetener) 0.20 Sodium Benzoate (preservative) 0.30 FD~C ~lue #1 (0.1%aq. soln.) 0.27 D&C Yellow ~10 (0.5~ aq. soln.) 0.50 Gelling agent 18.00 Glycerol (Humectant) 2Q.00 Cab-O-Sil M5 (Silicon Dioxide) 1.00 Plaque Barrier Agent 5.00 (dry basis) Flavor 0.80 100 .0 J&J 10~3 3~5~
.~
While the details of preparing all of the above formula-tions are well within the skill of the art, a suggested procedure for preparing the gel formulation of this example will be described for completeness.
In a first container the water, sodium saccharin, sodium benzoate and dyes are mixed. Then the container is put into an ice bath. When the temperature reaches 6C, the gelling agent is added and the contents mixed slowly until the gelling agent is dissolved. Then the solution is heated to 70C.
Into a second container is added the glycerin. Then the Cab~O-Sil M5 is sprinkled in with mixing. Then the plaque barrier agent is added and mixing continued to a smooth paste. The paste is then heated in a water bath with mixing to a temperature of 70C.
The contents of the first container are added to the second container and blended together until the batch is homogenous while maintaining a 70C temperature. Then the flavoring is added, all mixing is stopped, and the formu-lation allowed to settle for approximately one hour. If necessary to remove air bubbles, overnight refrigeration may be employed.
These compositions are preferably employed from one to three times daily in a routine oral hygiene program to prevent the attachment of plaque to the teeth.
Variations can, of course, be made without departing from the spirit or scope of the invention.
J&J 1023
Claims (4)
1. An oral hygiene composition comprising an effective amount for preventing deposition of dental plaque or teeth of an alkali metal salt of a homopoly-mer of vinylbenzoic acid having repeating units of structure (A), (A) wherein M is selected from the group consisting of lithium, sodium, and potassium, in a pharmaceutically acceptable oral hygiene vehicle compatible with said polymer.
2. The composition of claim 1, in the form of an oral hygiene formulation selected from the group consisting of mouthwashes, mouthrinses, irrigating solutions, abrasive gel dentifrices, non-abrasive gel dentifrices, denture cleaners, coated dental floss, coated interdental stimulators, chewing gums, lozenges, breath fresheners, foams and sprays.
3. The composition of claim 1, which further includes an anticaries fluoride compound.
4. The composition of claim 3, wherein said fluoride compound is sodium fluoride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000413631A CA1190150A (en) | 1982-10-18 | 1982-10-18 | Alkali metal salts of poly(vinylbenzoic acid) as dental plaque barrier agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000413631A CA1190150A (en) | 1982-10-18 | 1982-10-18 | Alkali metal salts of poly(vinylbenzoic acid) as dental plaque barrier agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1190150A true CA1190150A (en) | 1985-07-09 |
Family
ID=4123780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413631A Expired CA1190150A (en) | 1982-10-18 | 1982-10-18 | Alkali metal salts of poly(vinylbenzoic acid) as dental plaque barrier agents |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1190150A (en) |
-
1982
- 1982-10-18 CA CA000413631A patent/CA1190150A/en not_active Expired
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