US2746905A - Dehydroacetic acid dental compositions - Google Patents
Dehydroacetic acid dental compositions Download PDFInfo
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- US2746905A US2746905A US279648A US27964852A US2746905A US 2746905 A US2746905 A US 2746905A US 279648 A US279648 A US 279648A US 27964852 A US27964852 A US 27964852A US 2746905 A US2746905 A US 2746905A
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- Prior art keywords
- dehydroacetic acid
- weight
- compound
- dentifrice
- acid
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- 239000004287 Dehydroacetic acid Substances 0.000 title claims description 37
- 229940061632 dehydroacetic acid Drugs 0.000 title claims description 37
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 title claims description 37
- 235000019258 dehydroacetic acid Nutrition 0.000 title claims description 37
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 title claims description 33
- 239000000203 mixture Substances 0.000 title description 32
- 230000001225 therapeutic effect Effects 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002324 mouth wash Substances 0.000 claims description 15
- 229940051866 mouthwash Drugs 0.000 claims description 12
- 239000000551 dentifrice Substances 0.000 description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 229940039748 oxalate Drugs 0.000 description 16
- 159000000000 sodium salts Chemical class 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- -1 dehydroacetic acid compound Chemical class 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 230000001680 brushing effect Effects 0.000 description 5
- 210000000214 mouth Anatomy 0.000 description 5
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 5
- 229940039790 sodium oxalate Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 208000002925 dental caries Diseases 0.000 description 4
- 210000003298 dental enamel Anatomy 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 210000003296 saliva Anatomy 0.000 description 4
- 241000416162 Astragalus gummifer Species 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 238000013494 PH determination Methods 0.000 description 3
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002053 acidogenic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical class [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
Definitions
- This invention relates to therapeutic compositions and more particularly to therapeutic compositions for use in the oral cavity.
- the present invention is directed to dental therapeutic compositions which contain dehydroacetic acid compounds and which may also contain a water-soluble oxalate.
- compositions for use in the oral cavity which inhibit acid production for prolonged periods of time and are sufliciently persistent to inhibit acid formation from sugars ingested any time over a period of at least twelve hours; the provision of such therapeutic compositions which reduce the incidence of dental caries and which protect and whiten tooth enamel; the provision of compositions of the class described which increase the surface oxalate content of teeth and render teeth more resistant to acid attack; the provision of dental therapeutic compositions which are nontoxic, nonsensitizing, nonirritating and stable; and the provision of such therapeutic compositions which may be made from inexpensive and readily obtainable materials.
- Other features will be in part apparent and in part pointed out hereinafter.
- tooth decay is the result of acid action on tooth enamel. It is also recognized that inorganic tooth enamel material will be dissolved at a pH of approximately 5.2 or below. Acids which will act to damage the teeth are produced by acidogenic bacterial action. These bacteria, the enzymes formed by such bacteria and a carbohydrate substrate are necessary elements in the chemical conversion of sugars or starches into these destructive acids.
- the dehydroacetic acid compound component of these therapeutic compositions inhibits acid production by inhibiting enzymatic action necessary in the conversion of carbohydrates to acids, while the water-soluble oxalate component operates as an enamel protective agent to in- 2,745,905 Patented May 22, 1956 crease the resistance of the tooth to acid attack.
- These therapeutic compositions will exert a sufiiciently persistent effect in inhibiting acid production to be elfective under conditions of morning and evening use.
- the dehydroacetic acid compounds specified herein are not only compatible with other components generally used in therapeutic compositions which may be used orally, but they are also stable, nontoxic, nonirritating, nonsensitizing, inexpensive and readily available. It is preferred, however, that these compositions do not include an aldehyde.
- the therapeutic compositions of the present invention comprise a dehydroacetic acid compound and a vehicle for the compound which is compatible therewith.
- this vehicle would be the tooth cleaning components thereof.
- These compositions include not only paste, powder, and liquid dentifrices, but also mouthwashes, chewing gum, tablets, lozenges and troches.
- the percentage of the dehydroacetic acid compound incorporated in these therapeutic compositions may be varied considerably, although the preferred percentage by Weight is between approximately 0.5% and approximately 1.5%.
- the amount of oxalate component, if one is included in these compositions similarly may be varied considerably, but a range of approximately 0.25% to approximately 1.5% by weight is preferred.
- compositions may also vary depending upon whether the composition is a dentifrice, where say 1.0% of a dehydroacetic acid compound and 0.5% of the oxalate compound may be preferred, or a mouthwash where perhaps 0.5% of a dehydroacetic acid compound and 0.25% of the oxalate component are preferred.
- dehydroacetic acid compound includes dehydroacetic acid and its watersoluble salts, such as, for example, the sodium, potassium and ammonium salts.
- watersoluble salts such as, for example, the sodium, potassium and ammonium salts.
- any water-soluble oxalate such as sodium, potassium and ammonium oxalates and the urea salt of oxalic acid may be utilized in these dental therapeutic compositions.
- Example 1 A dentifrice composition was prepared from the following components:
- Example 2 A dentifrice composition as described in Example 1 was prepared, except that 0.75% of the sodium salt of dehydroacetic acid was employed. The percentage by weight of the water component was adjusted to compensate for the increased percentage of the sodium salt of dehydroacetic acid.
- Example 3 A dentifrice composition as described in Example 1 was prepared, except that 1.00% of the sodium salt of dehydroacetic acid was employed. The percentage by Weight of the water component was adjusted to compensate for the increased percentage of the sodium salt of dehydroacetic acid.
- Example 4 A dentrifrice composition was prepared from the following components:
- Example 5 A dentrifrice composition was prepared from the following components:
- Example 6 A mouthwash was prepared from the following components:
- Example 7 A mouthwash was prepared from the following components:
- Example 8 A number of subjects were given a standard dentrifrice which they used morning and evening for seven days. On the morning of the eighth day, and after the morning brushing, a 10 ml. sample of saliva, stimulated by chewing parafiin, was obtained from each subject. Duplicate samples of 4 ml. each were removed from the original 10 ml. sample and 1 ml. of glucose-water solution was added to each 4 ml. saliva sample. An initial pH of these (4 ml. saliva plus 1 ml. glucose solution) samples was determined by a Beckmann pH meter immediately after addition of the glucose solution. These two samples were incubated at 37.5 C. for four hours, the pH of each of the two samples being taken at two and at four hours after the initial pH determination. The averages of the pH values at O, 2 and 4 hours were plotted against time as shown by the dashed line of Fig. 1.
- Example 9 The procedure of Example 8 was repeated using the dentifrice of Example 2 in place of the Example 1 dentifrice.
- Example 10 A number of subjects were selected and the normal curve of the rate of acid production in the mouth was determined as follows: A given area of a given tooth of each subject was marked oft" and the pH of this tooth area was determined by means of microelectrode technique. The subjects then immediately rinsed their mouths for thirty seconds with a rinse of a 50% aqueous sucrose solution. The pH of the area was again determined by the microelectrode technique at intervals of 5, l0 and 15 minutes after the first pH determination. The averages of the pH values at 0, 5, 10, 15 and 20 minutes were plotted versus time as shown by the dashedline curve of Fig. 3.
- Example 2 The same subjects were then each given a supply of the dentrifrice of Example 2 which they used morning and evening for seven days. On the morning of the eighth day, and without a morning brushing, the pH of the marked tooth area of each subject was again determined by means of microelectrode technique. The subjects then immediately rinsed their months for thirty secends with a rinse of a 50% aqueous sucrose solution. The pH was again determined at intervals of 5, 10, 15 and 20 minutes after the first pH determination. The average pH values were plotted versus time as shown by the solid-line curve of Fig. 3.
- Example 11 The procedure of Example 8 was repeated using the dentifrice of Example 3 in place of the Example 1 dentifrice.
- the average pH values of the control curve are shown by the dashed-line curve of Fig. 4, and the results after the seven-day test period are shown by the solidline curve of Fig. 4.
- Example 12 The procedure of Example 10 was repeated using the dentrifn'ce of Example 3 in place of the Example 2 dentifrice.
- Example 13 The procedure of Example 10 was repeated using the dentifrice of Example 4 in place of the Example 2 dentifrice.
- Example 14 The procedure of Example 10 was repeated using the dentifrice of Example 5 in place of the Example 2 dentifrice.
- Example 15 The procedure of Example 10 was repeated using the mouthwash of Example 6 in place of the dentifrice of Example 2. It is to be understood that the mouthwash was used morning and evening as a mouth rinse instead of brushing the teeth morning and evening.
- Example 16 The procedure of Example was repeated using the mouthwash of Example 7 in place of the dentifrice of Example 2. it is to be understood that the mouthwash was used morning and evening as a mouth rinse instead or" brushing the teeth morning and evening.
- a therapeutic mouthwash comprising not less than 0.5 by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid and a dispersing vehicle compatible with said compound.
- a dental therapeutic composition comprising not less than 0.5 by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, and a dispersing vehicle compatible with said compound.
- a dental therapeutic composition comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, not substantially less than 0.25% by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with said compound.
- a therapeutic dentifrice comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, not substantially less than 0.25 by Weight of a Water-soluble oxalate, and tooth cleaning components, said tooth cleaning components being compatible with said compound.
- a therapeutic mouthwash comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the Water soluble salts of dehydroacetic acid, not substantially less than 0.25% by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with said compound.
- a therapeutic dentifrice comprising approximately 0.7 5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, approximately 0.5% by weight of a water-soluble oxalate, and tooth cleaning components, said tooth cleaning components being compatible with compound.
- a therapeutic mouthwash comprising approximately 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, approximately 0.25 by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with acid compound.
- a therapeutic paste dentifrice comprising approximately 0.75% by Weight of the sodium salt of dehydroacetic acid, approximately 0.5% by weight of sodium oxalate, and tooth cleaning components, said tooth cleaning components being compatible with said salt.
- a therapeutic mouthwash comprising approximately 0.5% by weight of the sodium salt of dehydroacetic acid, approximately 0.25 by weight of sodium oxalate, and an alcohol-water vehicle.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
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- Cosmetics (AREA)
Description
y 1956 H. M. BAUM DEHYDROACETIC ACID DENTAL COMPOSITIONS 2 Sheets-Sheet 1 Filed March 31, 1952 I I I I MOE @MFDZIL 3: v n M Q 8v [om I S I 3 1 Q o IQ 31v w N o mmmw u o mv 3 I l 1 I Q om A Q 1 I l l 0o 3 I $6 3 l IQN l ON I 2 m I1 May 22, 1956 H M. BAUM DEHYDROACETIC ACID DENTAL COMPOSITIONS 2 Sheets-Sheet 2 Filed March 31, 1952 III' I III QOE WMIDZZZ O.
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WWFDZZZ llllll'l QUE DEHYDRQACETEC ACID DENTAL COWOSITEQNS Harold M. Baum, Ladue, Mo., assignor to Warner-Lamhart Pharmaceutical Company, a corporation of Delaware Application March 31, 1952, Serial No. 279,648
9 Claims. (Cl. 167-93) This invention relates to therapeutic compositions and more particularly to therapeutic compositions for use in the oral cavity.
Briefly, the present invention is directed to dental therapeutic compositions which contain dehydroacetic acid compounds and which may also contain a water-soluble oxalate.
Among the several objects of the invention may be noted the provision of therapeutic compositions for use in the oral cavity which inhibit acid production for prolonged periods of time and are sufliciently persistent to inhibit acid formation from sugars ingested any time over a period of at least twelve hours; the provision of such therapeutic compositions which reduce the incidence of dental caries and which protect and whiten tooth enamel; the provision of compositions of the class described which increase the surface oxalate content of teeth and render teeth more resistant to acid attack; the provision of dental therapeutic compositions which are nontoxic, nonsensitizing, nonirritating and stable; and the provision of such therapeutic compositions which may be made from inexpensive and readily obtainable materials. Other features will be in part apparent and in part pointed out hereinafter.
The invention accordingly comprises the products hereinafter described, the scope of the invention being indicated in the following claims.
The accompanying drawings graphically illustrate the results of in vivo tests of the therapeutic activity and the inhibition of acid formation resulting from the use of the dental therapeutic compositions of the present invention, which tests will be described in detail hereinafter.
Research and study of dental caries etiology has revealed that tooth decay is the result of acid action on tooth enamel. It is also recognized that inorganic tooth enamel material will be dissolved at a pH of approximately 5.2 or below. Acids which will act to damage the teeth are produced by acidogenic bacterial action. These bacteria, the enzymes formed by such bacteria and a carbohydrate substrate are necessary elements in the chemical conversion of sugars or starches into these destructive acids.
It has been found in accordance with the present invention that the incidence of dental caries can be greatly reduced by the use of therapeutic compositions including dehydroacetic acid compounds. The introduction of such novel therapeutic compositions into the oral cavity inhibits acid formation over prolonged periods of time and operates to maintain the pH above a value of approximately 5.2. It has also been found that it is advantageous to incorporate a Water-soluble oxalate in the dehydroacetic acid compound-containing therapeutic compositions. Although the exact mechanism is'not entirely clear, it is believed that the dehydroacetic acid compound component of these therapeutic compositions inhibits acid production by inhibiting enzymatic action necessary in the conversion of carbohydrates to acids, while the water-soluble oxalate component operates as an enamel protective agent to in- 2,745,905 Patented May 22, 1956 crease the resistance of the tooth to acid attack. These therapeutic compositions will exert a sufiiciently persistent effect in inhibiting acid production to be elfective under conditions of morning and evening use. The dehydroacetic acid compounds specified herein are not only compatible with other components generally used in therapeutic compositions which may be used orally, but they are also stable, nontoxic, nonirritating, nonsensitizing, inexpensive and readily available. It is preferred, however, that these compositions do not include an aldehyde.
The therapeutic compositions of the present invention comprise a dehydroacetic acid compound and a vehicle for the compound which is compatible therewith. In the case of a dentifrice this vehicle would be the tooth cleaning components thereof. These compositions include not only paste, powder, and liquid dentifrices, but also mouthwashes, chewing gum, tablets, lozenges and troches. The percentage of the dehydroacetic acid compound incorporated in these therapeutic compositions may be varied considerably, although the preferred percentage by Weight is between approximately 0.5% and approximately 1.5%. The amount of oxalate component, if one is included in these compositions, similarly may be varied considerably, but a range of approximately 0.25% to approximately 1.5% by weight is preferred. These percentages may also vary depending upon whether the composition is a dentifrice, where say 1.0% of a dehydroacetic acid compound and 0.5% of the oxalate compound may be preferred, or a mouthwash where perhaps 0.5% of a dehydroacetic acid compound and 0.25% of the oxalate component are preferred.
It will be understood that the term dehydroacetic acid compound includes dehydroacetic acid and its watersoluble salts, such as, for example, the sodium, potassium and ammonium salts. Similarly, any water-soluble oxalate such as sodium, potassium and ammonium oxalates and the urea salt of oxalic acid may be utilized in these dental therapeutic compositions.
The following examples illustrate the invention.
Example 1 A dentifrice composition was prepared from the following components:
Components: Percent by weight Calcium sulfate 35.70 Dicalcium phosphate 15.60 Detergent 3.00 Gum tragacanth 1.40 Sodium saccharin 0.175 Glycerin 19.90 Water 22.525 Flavor 1.2 Sodium salt of dehydroacetic acid 0.50
Example 2 A dentifrice composition as described in Example 1 was prepared, except that 0.75% of the sodium salt of dehydroacetic acid was employed. The percentage by weight of the water component was adjusted to compensate for the increased percentage of the sodium salt of dehydroacetic acid.
Example 3 A dentifrice composition as described in Example 1 was prepared, except that 1.00% of the sodium salt of dehydroacetic acid was employed. The percentage by Weight of the water component was adjusted to compensate for the increased percentage of the sodium salt of dehydroacetic acid. a
Example 4 A dentrifrice composition was prepared from the following components:
Components: Percent by weight Alumina hydrate 48.30 Titanium dioxide 1.00 Detergent 3.00 Gum tragacanth 0.56 Sodium saccharin 0.15 d-Sorbitol solution 19.10 Glycerin 12.80 Water 12.62 Flavor 1.22 Sodium salt of dehydroacetic acid 0.75 Sodium oxalate 0.50
Example 5 A dentrifrice composition was prepared from the following components:
Components: Percent by weight Alumina hydrate 48.30 Titanium dioxide 1.00 Detergent 3.00 Gum tragacanth 0.56 Sodium saccharin 0.15 d-Sorbitol solution 19.10 Glycerin 12.80 Water 12.37 Flavor 1.22 Sodium salt of dehydroacetic acid 1.00 Sodium oxalate 0.50
Example 6 A mouthwash was prepared from the following components:
Ethyl alcohol ml 12.00
Water q. s. to rn1 100.00
Sodium salt of dehydroacet'ic acid g 1.00
Example 7 A mouthwash was prepared from the following components:
Ethyl alcohol ml 12.00
Water q. s. to ml 100.00
Sodium salt of dehydroacetic acid g 0.75
Sodium oxalate g 0.25
Example 8 A number of subjects were given a standard dentrifrice which they used morning and evening for seven days. On the morning of the eighth day, and after the morning brushing, a 10 ml. sample of saliva, stimulated by chewing parafiin, was obtained from each subject. Duplicate samples of 4 ml. each were removed from the original 10 ml. sample and 1 ml. of glucose-water solution was added to each 4 ml. saliva sample. An initial pH of these (4 ml. saliva plus 1 ml. glucose solution) samples was determined by a Beckmann pH meter immediately after addition of the glucose solution. These two samples were incubated at 37.5 C. for four hours, the pH of each of the two samples being taken at two and at four hours after the initial pH determination. The averages of the pH values at O, 2 and 4 hours were plotted against time as shown by the dashed line of Fig. 1.
The same subjects were then each given a sample of the dentifrice of Example 1 which they used morning and evening for seven more days. On the morning of the eighth day, and without a morning brushing, a 10 ml. sample of stimulated saliva was taken, duplicate 4 ml. samples removed, glucose solution added, the samples incubated and the pH determined as described in the preceding paragraph. The results are indicated graph ically by the solid-line curve of Fig. 1,
4 Example 9 The procedure of Example 8 was repeated using the dentifrice of Example 2 in place of the Example 1 dentifrice.
The average pH values after the initial seven-day period are shown by the dashed-line curve of Fig. 2, and the results after the second seven-day period are shown by the solid-line curve of Fig. 2.
Example 10 A number of subjects were selected and the normal curve of the rate of acid production in the mouth was determined as follows: A given area of a given tooth of each subject was marked oft" and the pH of this tooth area was determined by means of microelectrode technique. The subjects then immediately rinsed their mouths for thirty seconds with a rinse of a 50% aqueous sucrose solution. The pH of the area was again determined by the microelectrode technique at intervals of 5, l0 and 15 minutes after the first pH determination. The averages of the pH values at 0, 5, 10, 15 and 20 minutes were plotted versus time as shown by the dashedline curve of Fig. 3.
The same subjects were then each given a supply of the dentrifrice of Example 2 which they used morning and evening for seven days. On the morning of the eighth day, and without a morning brushing, the pH of the marked tooth area of each subject was again determined by means of microelectrode technique. The subjects then immediately rinsed their months for thirty secends with a rinse of a 50% aqueous sucrose solution. The pH was again determined at intervals of 5, 10, 15 and 20 minutes after the first pH determination. The average pH values were plotted versus time as shown by the solid-line curve of Fig. 3.
Example 11 The procedure of Example 8 was repeated using the dentifrice of Example 3 in place of the Example 1 dentifrice. The average pH values of the control curve are shown by the dashed-line curve of Fig. 4, and the results after the seven-day test period are shown by the solidline curve of Fig. 4.
Example 12 The procedure of Example 10 was repeated using the dentrifn'ce of Example 3 in place of the Example 2 dentifrice.
The average pH values of the control curve are shown by the dashed-line curve of Fig. 5, and the results after the seven-day test period are shown by the solid-line curve of Fig. 5.
Example 13 The procedure of Example 10 was repeated using the dentifrice of Example 4 in place of the Example 2 dentifrice.
The average pH values of the control curve are shown by the dashed-line curve of Fig. 6, and the results after the seven-day test period are shown by the solid-line curve of Fig. 6.
Example 14 The procedure of Example 10 was repeated using the dentifrice of Example 5 in place of the Example 2 dentifrice.
The average pH values of the control curve are shown by the dashed-line curve of Fig. 7, and the results after the seven-day test period are shown by the solid-line curve of Fig. 7.
Example 15 The procedure of Example 10 was repeated using the mouthwash of Example 6 in place of the dentifrice of Example 2. It is to be understood that the mouthwash was used morning and evening as a mouth rinse instead of brushing the teeth morning and evening.
The average pH values of the control curve are shown by the dashed'line curve of Fig. 8, and the results after the seven-day test period are shown by the solid-line curve of Fig. 8.
Example 16 The procedure of Example was repeated using the mouthwash of Example 7 in place of the dentifrice of Example 2. it is to be understood that the mouthwash was used morning and evening as a mouth rinse instead or" brushing the teeth morning and evening.
The average pH values of the control curve are shown by the dashed-line curve of Fig. 9, and the results after the seven-day test period are shown by the solid-line curve of Fig. 9.
in view of the above, it will be seen that the several objects of the invention are achieved and other advantageous results attained.
As many changes could be made in the above products without departing from the scope of the invention, it is intended that all matter contained in the above description or shown in the accompanying drawings shall be interpreted as illustrative and not in a limiting sense.
1 claim:
1. A therapeutic mouthwash comprising not less than 0.5 by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid and a dispersing vehicle compatible with said compound.
2. A dental therapeutic composition comprising not less than 0.5 by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, and a dispersing vehicle compatible with said compound.
3. A dental therapeutic composition comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, not substantially less than 0.25% by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with said compound.
4. A therapeutic dentifrice comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, not substantially less than 0.25 by Weight of a Water-soluble oxalate, and tooth cleaning components, said tooth cleaning components being compatible with said compound.
5. A therapeutic mouthwash comprising not substantially less than 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the Water soluble salts of dehydroacetic acid, not substantially less than 0.25% by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with said compound.
6. A therapeutic dentifrice comprising approximately 0.7 5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, approximately 0.5% by weight of a water-soluble oxalate, and tooth cleaning components, said tooth cleaning components being compatible with compound.
7. A therapeutic mouthwash comprising approximately 0.5% by weight of a compound selected from the group consisting of dehydroacetic acid and the water soluble salts of dehydroacetic acid, approximately 0.25 by weight of a water-soluble oxalate, and a vehicle for said compound and oxalate, said vehicle being compatible with acid compound.
8. A therapeutic paste dentifrice comprising approximately 0.75% by Weight of the sodium salt of dehydroacetic acid, approximately 0.5% by weight of sodium oxalate, and tooth cleaning components, said tooth cleaning components being compatible with said salt.
9. A therapeutic mouthwash comprising approximately 0.5% by weight of the sodium salt of dehydroacetic acid, approximately 0.25 by weight of sodium oxalate, and an alcohol-water vehicle.
References Cited in the file of this patent UNITED STATES PATENTS 2,474,227 Coleman et a1 June 28, 1949 2,474,229 Coleman June 28, 1949 FOREIGN PATENTS 134, 156 Australia Sept. 6, 1947 OTHER REFERENCES Orol Surgery, Oral Med. and Oral Path, April 1949,
Oral Medicine, pages 459-473 (page 471 pertinent).
Science News Letter, August 29, 1953, page 131. Goodman: Cosmetic Dermatology, McGraw-Hill Book' Company, Inc., page 424 (1936).
Science News Letter, page 252, October 18, 1947.
Claims (1)
1. A THERAPEUTIC MOUTHWASH COMPRISING NOT LESS THAN 0.5% BY WEIGHT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF DEHYDROACETIC ACID AND THE WATER SOLUBLE SALTS OF DEHYDROACETIC ACID AND DISPERSING VEHICLE COMPATIBLE WITH SAID COMPOUND.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US279648A US2746905A (en) | 1952-03-31 | 1952-03-31 | Dehydroacetic acid dental compositions |
GB8921/53A GB779734A (en) | 1952-03-31 | 1953-03-31 | Improvements in dental therapeutic compositions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US279648A US2746905A (en) | 1952-03-31 | 1952-03-31 | Dehydroacetic acid dental compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US2746905A true US2746905A (en) | 1956-05-22 |
Family
ID=23069869
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US279648A Expired - Lifetime US2746905A (en) | 1952-03-31 | 1952-03-31 | Dehydroacetic acid dental compositions |
Country Status (2)
Country | Link |
---|---|
US (1) | US2746905A (en) |
GB (1) | GB779734A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4057621A (en) * | 1976-05-24 | 1977-11-08 | Pashley David H | Desensitizing oxalate dental composition and method of treatment |
US10231913B2 (en) * | 2013-10-28 | 2019-03-19 | The Procter & Gamble Company | Tooth desensitizing oral care compositions, devices, and methods |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2474229A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Retarding growth of microorganisms in light alocholic beverages |
US2474227A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Making carbohydrate foods resistant to microorganisms |
-
1952
- 1952-03-31 US US279648A patent/US2746905A/en not_active Expired - Lifetime
-
1953
- 1953-03-31 GB GB8921/53A patent/GB779734A/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2474229A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Retarding growth of microorganisms in light alocholic beverages |
US2474227A (en) * | 1947-01-13 | 1949-06-28 | Dow Chemical Co | Making carbohydrate foods resistant to microorganisms |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4057621A (en) * | 1976-05-24 | 1977-11-08 | Pashley David H | Desensitizing oxalate dental composition and method of treatment |
US10231913B2 (en) * | 2013-10-28 | 2019-03-19 | The Procter & Gamble Company | Tooth desensitizing oral care compositions, devices, and methods |
Also Published As
Publication number | Publication date |
---|---|
GB779734A (en) | 1957-07-24 |
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