US3542917A - Dental calculus inhibitor - Google Patents
Dental calculus inhibitor Download PDFInfo
- Publication number
- US3542917A US3542917A US738389A US3542917DA US3542917A US 3542917 A US3542917 A US 3542917A US 738389 A US738389 A US 738389A US 3542917D A US3542917D A US 3542917DA US 3542917 A US3542917 A US 3542917A
- Authority
- US
- United States
- Prior art keywords
- teeth
- acid
- composition
- saliva
- test
- 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 - Lifetime
Links
- 208000006558 Dental Calculus Diseases 0.000 title description 5
- 206010044029 Tooth deposit Diseases 0.000 title description 5
- 239000003112 inhibitor Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 description 27
- 229920000728 polyester Polymers 0.000 description 24
- 239000002253 acid Substances 0.000 description 21
- 210000003296 saliva Anatomy 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 18
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 16
- 229910052791 calcium Inorganic materials 0.000 description 16
- 239000011575 calcium Substances 0.000 description 16
- 230000003247 decreasing effect Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 239000002324 mouth wash Substances 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229940051866 mouthwash Drugs 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 210000004763 bicuspid Anatomy 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229960005233 cineole Drugs 0.000 description 2
- -1 ether polyol Chemical class 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 229940034610 toothpaste Drugs 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000005888 Periodontal Pocket Diseases 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 208000024693 gingival disease Diseases 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 230000003239 periodontal effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000021058 soft food Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
Definitions
- the composition includes, in a physiologically acceptable vehicle a solution of a polyester of a polycarboxylic acid having at least three carboxyl groups with a polyalkylene ether polyol having a molecular weight of at least 400, the ester having a molecular weight of at least 600 and a neutralization equivalent from 200 to 5000.
- This invention relates to a composition for inhibiting at least in part the deposition of calculus on the surface of teeth and pertains more specifically to a composition comprising a physiologically acceptable vehicle and a solution in a suitable solvent of certain acidic polyesters of polyalkylene ether polyols.
- Dental calculus is a hard intractable deposit which accumulates on those tooth surfaces subject to little abrasion or wear under normal conditions. Calculus is formed at least partially from material contained in the saliva. Frequently these calculus deposits accumulate on those surfaces of teeth adjacent to gum tissue and tend to cause irritation, pain, and rupture of the gum tissue, and if allowed to persist, produce open areas between the root of the tooth and its supporting gum tissue. These areas, called periodontal pockets, may become filled with calculus which further aggravates the supporting gum tissue and in extreme cases can exert sufficient pressure against the supporting bone to cause it to resorb. Recession of the gum tissue from the root of the tooth may also occur. If damage to the tissues supporting the tooth is sufficiently severe, loss of the tooth may result. Even in less severe cases of periodontal or gum disease the affiicted individual may find it necessary to restrict his diet to soft foods, and in any event dental calculus deposits are cosmetically unattractive.
- esters of the present invention when applied to teeth inhibit at least in part the formation of calculus deposits on the surfaces of the teeth. While the theory of operation of the present invention may not be fully understood and applicants do not wish to be limited thereto, it is believed that the compositions of the present invention function by chemical sorption of the acid polyesters in dilute solution with the surface of the teeth to form an adherent coating which interferes with the normal mechanism for calculus deposition.
- the method by which the acidic polyesters are applied to the teeth is not critical and any method may be employed which allows the composition to achieve contact with the tooth surfaces.
- the composition may be applied in the form of a toothpaste, mouthwash, chewing gum, etc., and the time periods and temperatures normally employed for brushing the teeth or using a mouthwash suffice to permit the acidic polyester to sorb on the teeth.
- the amount of acid polyester present in the total composition is not critical; satisfactory results are obtained when the acid 3,542,917 Patented Nov. 24, 1970 polyester amounts to 0.1 to 20% by weight of the total composition including the vehicle.
- the solvent in which the acid polyester is dissolved in the composition may be water, ethyl alcohol, or other liquid solvent chemically inert to the acid polyester and suitable for use in the mouth. A mixture of two or more such solvents may be employed if desired.
- any of the usual additives employed in conventional mouthwashes or toothpastes may be present in the composltions of the present invention.
- Such additives include menthol, eucalyptol, methyl salicylate, and the like to provide flavor and astringency; thymol, boric acid, benzoic acid or other similar antiseptic; and any of the usual abrasive materials and thickeners employed in toothpaste.
- the polyesters of the present invention may be prepared from a variety of starting'materials but will be defined in terms of their alcohol and acid components as is usual in defining esters.
- the alcoholic component may be any polyalkylene ether having at least two hydroxyl groups, and having a weight average molecular weight of at least 400; among suitable materials are tetrahydric polyether alcohols of various molecular weights made by the ethoxylation of pentaerythritol, and trihydric polyether alcohols made by ethoxylation of glycerol; polyethylene glycol and polypropylene glycol of molecular weight 400 to 10,000 are particularly preferred.
- the acid component of the polyester may be any of a variety of polycarboxylic acids having three or more carboxyl groups such as citric, tricarballylic, mellitic, trimesic, trimellitic, acontic, pyromellitic, polyacrylic, and the like. These acids contain, except for the oxygen of the carboxyl and hydroxyl groups, only carbon and hydrogen.
- the useful esters are polyesters in the usual sense inasmuch as they contain a plurality of ester linkages at spaced intervals in the backbone or chain of carbon atoms of the molecule.
- the polyester of such alcohol and acid components contain some free unreacted carboxyl groups; the proportion of such carboxyl groups may be defined in terms of the neutralization equivalent of the polyester, that is the weight average molecular weight of the polyester divided by the number of free acidic groups in the molecule (Shriner and Fuson, Systematic Identification of Organic Compounds, 3rd ed. John Wiley, New York, 1948).
- the acid polyesters of the present invention should have a neutralization equivalent in the range of 200 to 5000.
- the carboxyl groups may be terminal groups or they may be pendent on the backbone of the polyester molecules.
- the weight average molecular weight of the polyesters preferably is at least 600.
- the acid polyesters may be prepared by esterifying the alcohol component with the appropriate acid, or by reacting the alcohol component with an acid halide or acid anhydride, the relative proportions of the reactant being chosen so that the number of hydroxyl groups in the alcoholic component is insufficient to react with all of the carboxyl or acyl halide or acid anhydride groups. If necessary, hydrolysis of residual acyl halide or acid anhydride groups may be carried out so that the finished polyester contains free carboxyl groups.
- composition for use on the teeth containing a solution of the acidic polyester, should have a pH of 2 to 7, that is, the hydrogen ion concentration in the composition should be such that its negative logarithm is from 2 to 7.
- the acid polyesters of the present invention were tested for effectiveness by immersing sound extracted human bicuspid teeth in human saliva at room temperature for stated time periods; at specified intervals the teeth were removed from the saliva and immersed for a specified time period (usually 30 seconds) in a solution of the desired acid polyester. Changes in the calcium content of the saliva were determined by analysis, and extent of deposition of calculus on the teeth was observed. The results are set forth in the following specific examples which are intended to illustrate more clearly the nature of the present invention.
- EXAMPLE 1 In a 100 ml. beaker were placed 30 grams (.005 mole) of poly (ethylene glycol) 6000, 1 gram (.005 mole) of pyromellitic dianhydride and 0.1 ml. of 35 percent aqueous hydrochloric acid as a catalyst. The reactants were heated to 90 C., and allowed to remain at that temperature for a period of four hours with agitation. The product had a melting point of 52.5 C. and a neutralization equivalent of 2080. The infrared spectrum of the product showed it to be an ester of poly (ethylene glycol) and pyromellitic acid.
- a 0.5 percent aqueous solution of the ester was prepared.
- Two clean, sound bicuspid teeth were treated by dipping them in this solution 30 seconds daily for a period of three weeks.
- the teeth were dipped and withdrawn at two second intervals in human saliva containing 62.4 parts per million (p.p.m.) calcium.
- the calcium content of the saliva had decreased only to 50.8 and 56.0 p.p.m., respectively.
- the treated teeth gained 0.24 and 0.31 percent in weight, and mechanically removed scrapings were found to contain only 0.12 and 0.16 milligram calcium, respectively.
- EXAMPLE 2 A similar test was conducted with the ester described in Example 1, using the same techniques, with teeth and saliva obtained from other people.
- the fresh saliva used in this experiment contained 48.8 p.p.m. calcium. After three weeks contact with the teeth the calcium content of the saliva exposed to the treated teeth decreased to 28.8 p.p.m. while that exposed to untreated teeth decreased to 13.6 p.p.m.
- the untreated teeth had appreciably larger calculus deposits than the treated teeth.
- EXAMPLE 3 A test similar to that described in Example 1 was conducted except that a 1 percent aqueous solution of the ester was used.
- the saliva used in this test had an initial calcium content of 43 p.p.m. which decreased to 27 p.p.m. when exposed to the treated teeth.
- the calcium content decreased to 16 p.p.m.
- the treated teeth appeared substantially cleaner and relatively free of calculus deposits when compared with the untreated teeth in this test after two weeks exposure.
- EXAMPLE 4 A test similar to that described in Example 1 was conducted except that a 2 percent aqueous solution of the ester was used.
- the saliva used in this test had an initial calcium content of 61 p.p.m. which decreased to 55 p.p.m. when exposed to the treated teeth, but decreased to only 30 p.p.m. when exposed to untreated teeth. correspondingly, the treated teeth appeared substantially cleaner and relatively free of calculus deposits when com- 4 pared with the untreated teeth in this test after two weeks exposure.
- EXAMPLE 5 A test similar to that described in Example 1 was conducted except that a 4 percent aqueous solution of the ester was used.
- the saliva used in this test had an initial calcium content of 49 which decreased to 36 p.p.m. when exposed to the treated teeth, and decreased to 27 p.p.m. when exposed to untreated teeth.
- the treated teeth appeared substantially cleaner and relatively free of calculus deposits when compared with the untreated teeth in this test after two weeks exposure.
- EXAMPLE 6 A test similar to that described in Example 1 was conducted except that in place of the 0.5 percent aqueous solution of ester there was employed a mouthwash having the following composition.
- the saliva used in this test had an initial calcium content of 58 p.p.m. which did not decrease when exposed to the treated teeth. In contrast, that portion of the saliva sample exposed to untreated teeth decreased in content to 42 p.p.m. after the test. Correspondingly, the treated teeth appeared substantially cleaner and relatively free of calculus deposits when compared with the untreated teeth in this test after two Weeks exposure.
- EXAMPLE 7 In a ml. beaker were placed 30 grams .005 mole) poly (ethylene glycol) 6000, and 1.2 grams (.005 mole) aconityl chloride. The mixture was heated to 70 C. and agitated at that temperature for 2 hours. There was then added to the reaction mixture 1.8 grams (0.1 mole) of water and the mixture was heated to C. for about 15 minutes until evolution of hydrogen chloride ceased. The resulting ester product had a melting point of 47.5 C. and a neutralization equivalent of 387. A five percent aqueous solution of the ester was prepared and tested by the procedure of Example 1. The saliva used in this test had an initial calcium content of 67 p.p.m. which decreased to 55 p.p.m. when exposed to the treated teeth, and to 49 p.p.m. when exposed to untreated teeth. Correspondingly, the treated teeth appeared substantially cleaner and relatively free of calculus deposits when compared with the untreated teeth in this test after three weeks exposure.
- EXAMPLE 8 In a 100 ml. beaker were placed 31 grams (.016 mole) poly (propylene glycol) with a molecular weight of 2000, 3.4 grams (.016 mole) pyromellitic dianhydride and .1 ml. 35 percent aqueous hydrochloric acid. The mixture was heated to C. for 35 minutes and subsequently allowed to cool. The resulting ester product was an amber solid which had a melting point of 62.5 C. and a neutralization equivalent of 930. A 0.5 aqueous solution of the poly (propylene glycol) ester of pyromellitic acid described above was prepared and tested as in Example 1. The saliva used in this test had an initial calcium content of 32 p.p.m.
- a composition for treating teeth which comprises a physiologically acceptable vehicle containing in solution from 0.1 to 20 percent by weight of a polyester of (1) a polycarboxylic acid having three to six carboxyl groups with (2) a polyalkylene ether having two to four hydroxyl groups and having a molecular weight of 400 to 10,000, said ester having a molecular weight of at least 600 and a neutralization equivalent from 200 to 5,000.
- composition as claimed in claim 5 in which said acid is pyromellitic.
- a method of treating teeth to reduce calculus formation thereon which comprises contacting the surface thereof with a composition as claimed in claim 1.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US73838968A | 1968-06-20 | 1968-06-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3542917A true US3542917A (en) | 1970-11-24 |
Family
ID=24967791
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US738389A Expired - Lifetime US3542917A (en) | 1968-06-20 | 1968-06-20 | Dental calculus inhibitor |
Country Status (11)
Country | Link |
---|---|
US (1) | US3542917A (de) |
AT (1) | AT291442B (de) |
BE (1) | BE734721A (de) |
BR (1) | BR6909992D0 (de) |
CA (1) | CA920513A (de) |
CH (1) | CH517490A (de) |
DE (1) | DE1931451A1 (de) |
FR (1) | FR2011342A1 (de) |
GB (1) | GB1256267A (de) |
NL (1) | NL6909428A (de) |
SE (1) | SE356212B (de) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3671626A (en) * | 1970-12-14 | 1972-06-20 | Gillette Co | Inhibiting dental plaque |
US4080441A (en) * | 1976-12-27 | 1978-03-21 | Colgate-Palmolive Company | Antibacterial oral composition |
US4105756A (en) * | 1976-11-24 | 1978-08-08 | Monsanto Company | Inhibition of dental calculus |
US4130635A (en) * | 1976-11-22 | 1978-12-19 | Monsanto Company | Calculus inhibition |
US4139609A (en) * | 1976-12-27 | 1979-02-13 | Colgate Palmolive Company | Oral compositions containing an anticalculus agent |
US4139608A (en) * | 1976-12-27 | 1979-02-13 | Colgate Palmolive Company | Oral compositions containing an anticalculus agent |
US4143125A (en) * | 1976-12-27 | 1979-03-06 | Monsanto Company | Calculus-inhibiting compositions and method |
US4151271A (en) * | 1976-11-01 | 1979-04-24 | Monsanto Company | Oral compositions |
US4188372A (en) * | 1976-12-27 | 1980-02-12 | Colgate-Palmolive Company | Antibacterial oral composition |
US4289753A (en) * | 1977-04-04 | 1981-09-15 | Monsanto Company | Calculus-inhibiting method and compositions |
US6013287A (en) * | 1996-10-22 | 2000-01-11 | Wm. Wrigley Jr. Company | Gum base and chewing gum containing edible polyesters |
US6017566A (en) * | 1997-10-20 | 2000-01-25 | Wm. Wrigley Jr. Company | Gum base and chewing gum containing edible polyesters and method for manufacture |
US9616003B2 (en) | 2012-05-31 | 2017-04-11 | Hakki Sema | Antibacterial mouthwash which is nontoxic in cellular level |
WO2017097638A1 (de) * | 2015-12-09 | 2017-06-15 | Basf Coatings Gmbh | Carboxyfunktionelle polyether-basierte reaktionsprodukte und wässrige basislacke enthaltend die reaktionsprodukte |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050215730A1 (en) * | 2004-03-24 | 2005-09-29 | Rainer Schoenfeld | Polycarboxy-functionalized prepolymers |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3108085A (en) * | 1960-04-29 | 1963-10-22 | Standard Oil Co | Polyester resin based on a tetracarboxylic acid |
US3120469A (en) * | 1959-09-24 | 1964-02-04 | Tamas Istvan | Therapeutic dental composition |
-
1968
- 1968-06-20 US US738389A patent/US3542917A/en not_active Expired - Lifetime
-
1969
- 1969-06-12 CA CA054177A patent/CA920513A/en not_active Expired
- 1969-06-16 GB GB30299/69A patent/GB1256267A/en not_active Expired
- 1969-06-18 BE BE734721D patent/BE734721A/xx unknown
- 1969-06-19 SE SE08789/69A patent/SE356212B/xx unknown
- 1969-06-19 CH CH940369A patent/CH517490A/fr not_active IP Right Cessation
- 1969-06-19 NL NL6909428A patent/NL6909428A/xx unknown
- 1969-06-20 FR FR6920799A patent/FR2011342A1/fr not_active Withdrawn
- 1969-06-20 DE DE19691931451 patent/DE1931451A1/de active Granted
- 1969-06-20 AT AT587369A patent/AT291442B/de not_active IP Right Cessation
- 1969-06-20 BR BR209992/69A patent/BR6909992D0/pt unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3120469A (en) * | 1959-09-24 | 1964-02-04 | Tamas Istvan | Therapeutic dental composition |
US3108085A (en) * | 1960-04-29 | 1963-10-22 | Standard Oil Co | Polyester resin based on a tetracarboxylic acid |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3671626A (en) * | 1970-12-14 | 1972-06-20 | Gillette Co | Inhibiting dental plaque |
US4151271A (en) * | 1976-11-01 | 1979-04-24 | Monsanto Company | Oral compositions |
US4130635A (en) * | 1976-11-22 | 1978-12-19 | Monsanto Company | Calculus inhibition |
US4105756A (en) * | 1976-11-24 | 1978-08-08 | Monsanto Company | Inhibition of dental calculus |
US4188372A (en) * | 1976-12-27 | 1980-02-12 | Colgate-Palmolive Company | Antibacterial oral composition |
US4139609A (en) * | 1976-12-27 | 1979-02-13 | Colgate Palmolive Company | Oral compositions containing an anticalculus agent |
US4139608A (en) * | 1976-12-27 | 1979-02-13 | Colgate Palmolive Company | Oral compositions containing an anticalculus agent |
US4143125A (en) * | 1976-12-27 | 1979-03-06 | Monsanto Company | Calculus-inhibiting compositions and method |
US4080441A (en) * | 1976-12-27 | 1978-03-21 | Colgate-Palmolive Company | Antibacterial oral composition |
FR2374898A1 (fr) * | 1976-12-27 | 1978-07-21 | Colgate Palmolive Co | Composition buccale antibacterienne contenant un ester de bis-(o-carboxyphenyle) d'un acide carboxylique |
US4289753A (en) * | 1977-04-04 | 1981-09-15 | Monsanto Company | Calculus-inhibiting method and compositions |
US6013287A (en) * | 1996-10-22 | 2000-01-11 | Wm. Wrigley Jr. Company | Gum base and chewing gum containing edible polyesters |
US6017566A (en) * | 1997-10-20 | 2000-01-25 | Wm. Wrigley Jr. Company | Gum base and chewing gum containing edible polyesters and method for manufacture |
US9616003B2 (en) | 2012-05-31 | 2017-04-11 | Hakki Sema | Antibacterial mouthwash which is nontoxic in cellular level |
WO2017097638A1 (de) * | 2015-12-09 | 2017-06-15 | Basf Coatings Gmbh | Carboxyfunktionelle polyether-basierte reaktionsprodukte und wässrige basislacke enthaltend die reaktionsprodukte |
US10793744B2 (en) | 2015-12-09 | 2020-10-06 | Basf Coatings Gmbh | Carboxy-functional polyether-based reaction products and aqueous base coats containing the reaction products |
Also Published As
Publication number | Publication date |
---|---|
GB1256267A (en) | 1971-12-08 |
CA920513A (en) | 1973-02-06 |
FR2011342A1 (de) | 1970-02-27 |
CH517490A (fr) | 1972-01-15 |
DE1931451A1 (de) | 1970-06-04 |
SE356212B (de) | 1973-05-21 |
AT291442B (de) | 1971-07-12 |
BE734721A (de) | 1969-12-18 |
BR6909992D0 (pt) | 1973-04-26 |
NL6909428A (de) | 1969-12-23 |
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