US3201316A - Trifluorostannite salts of amines in oral compositions for caries prophylaxis - Google Patents

Trifluorostannite salts of amines in oral compositions for caries prophylaxis Download PDF

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Publication number
US3201316A
US3201316A US227044A US22704462A US3201316A US 3201316 A US3201316 A US 3201316A US 227044 A US227044 A US 227044A US 22704462 A US22704462 A US 22704462A US 3201316 A US3201316 A US 3201316A
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United States
Prior art keywords
trifluorostannite
salts
amines
amine
caries
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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
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US227044A
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English (en)
Inventor
Paul E Norris
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Procter and Gamble Co
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Procter and Gamble Co
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Publication date
Priority to BE637883D priority Critical patent/BE637883A/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US227044A priority patent/US3201316A/en
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Publication of US3201316A publication Critical patent/US3201316A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A61K8/21—Fluorides; Derivatives thereof
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof

Definitions

  • This invention relates to a new class of compounds More particularly, it relates to trifluorostannite salts of amines and oral compositions for caries prophylaxis containing same.
  • oral composition means a product which in the ordinary course of usage would not be ingested, but would be retained in the oral cavity for a time suflicient to contact substantially all of the dental surfaces.
  • Such products include, for example, dentifrices, mouthwashes, dental prophylaxis pastes and topical solutions.
  • inorganic fluoride compounds have been employed for caries prophylaxis.
  • sodium fluoride has been found to be a preferred watersoluble source of fluoride ion to use in drinking water.
  • Stannous fluoride has been used with a great degree of success in topical application of oral compositions for caries prophylaxis, with both the stannous ion and the fluoride ion playing an important role in anticaries effeet by virtue of their ability to reduce the solubility rate of dental enamel.
  • Organic fluorides such as amine hydrofluorides have also been suggested for use in formulations for caries prophylaxis.
  • novel class of compounds of this invention are trifluorostannite salts of amines having the general structural formula:
  • R R and R are each members selected from the group consisting of hydrogen, and alkyl, hydroxyalkyl and aminoalkyl radicals, at least one of said Rs being one of said radicals containing from about 1 to about 18 carbon atoms.
  • the total carbon content of R R and R will be less than about 30 carbon atoms.
  • the compound must be sufliciently soluble to provide about 50 ppm. of analytically available fluoride ions in aqueous solution.
  • Hydrophilic substituents such as hydroxyl radicals increase the solubility and permit radicals of greater chain lengths.
  • Such substituted trifluorostannite salts are especially preferred for the purposes of this invention.
  • compositions of this invention include the following:
  • the trifiuorostannite salts listed in column 2 are prepared by reacting equimolar quantitles of the desired .amine and hydrofluoric acid and subsequently reacting the resultant amine hydrofluorides with equimolar quantities of stannous fluoride in aqueous solution.
  • Test method I Step 1.Six human cuspid or bicuspid teeth, free of decay and fillings, are cleaned with a scalpel and polished with a fluor ide free dentifrice. A portion of the roots are cut off to permit imbedding the upright tooth to the enamel margin in hot inlay casting wax contained in a beaker. Additional hot Wax is touched t-o flaw-spots on the enamel and allowed to harden. The teeth are then covered with distilled water until immediately prior to use.
  • Step 2 A base line solubility rate for the six teeth is obtained by totally immersing them in 40 ml. of an acid buffer solution (approximately 0.1 N lactic acidsodium lactate adjusted to pH 4.5 with NaOH) for minutes. During this time interval the beaker is immersed in a water bath kept at 37 C. and the buffer solution is stirred mechanically with a glass propeller turning at a speed of 1700 rpm. At the end of the accur-ately timed 15 minute interval, the buffer solution is removed from the teeth and set aside for analysis. The teeth are immediately rinsed with distilled water.
  • an acid buffer solution approximately 0.1 N lactic acidsodium lactate adjusted to pH 4.5 with NaOH
  • Step 3 The rinsed teeth are immersed in an aqueous solution of the agent to be evaluated (40 ml.), while maintaining the system at 37 C. with stirring for a 5 minute accurately timed period. The solution is then quickly removed from the beaker, the teeth are rinsed with Water and step 2 is repeated.
  • Chemical analysis of solutions from steps 2 and 3 for phosphate ion is undertaken using the methods of Martin, J, B. and Doty, D. M., Anal. Chem. 21, 965 (1949) or Lucena-Conde & Prat, Analytica Chemica Acta 16, 473 (1957). Comparison of the two values (decalcification of teeth by acid with and Without pre-treatment) permits calculation of a percentage reduction in enamel solubility rate.
  • the following table sets forth the percentage reduction in enamel solubility rate effected through the use of several of the compounds of the present invention.
  • the amine trifluorostannite salts are highly effective in reducing the solubility of dental enamel.
  • one of the causes of caries is the demineralization of dental enamel in the presence of the biologically produced acids of the oral cavity. The relationship between reduction of enamel solubility and reduced caries incidence is well established.
  • compositions of this invention contain at least one of the hereinbefore described trifluorostannite salts and a fluoride compatible vehicle.
  • the pH of the oral compositions of this invention is desirably within the range from about 3.5 to about 6.0. Above about pH 6.0 the stannous ion hydrolyze to form stannous hydroxide which has no effect in protecting dental enamel. Below about pH 3.5 the consumer characteristics of the product are altered in an undesirable way. Preferably the pH values of the compositions are maintained within the range from about 4.5 to about 5.5.
  • the trifluorostannite salts of amines can be used in varying concentrations in the oral compositions of this invention.
  • concentrations of the amine trifluorostannit sufficient to provide from about p.p.m. to 7500 p.p.m. of fluoride ion can be used.
  • concentrations providing from about 100 p.p.m. to about 4000 p.p.m. of fluoride ion can be employed.
  • these compounds are present in an amount sufiicient to provide from about 500 to 2,000 parts of fluoride ion per million parts of the total composition in products intended for unsupervised use by the consumer.
  • Dentifrice compositions containing the amine trifluorostannites constitute a preferred embodiment of this invention.
  • such dentifrice compositions will be formulated with components possessed of a high level of ionic compatibility so that the stability of the product is maintained.
  • compatible abrasive materials such as particulate condensation products of melamine and urea or formaldehyde which do not form insoluble salts with fluoride ions or inactive stannous and fluoride ions by adsorption are preferred.
  • Other abrasives which are practical both from the standpoint of compatibility and availability and which are desirable for use in the dentifrice compositions of this invention include calcium pyrophosphate, insoluble metaphosphates and alumina.
  • Toothpastes require binder substances to impart desired texture properties.
  • Natural gum binders such as gum tragacanth, gum karaya, gum arabic, etc. and seaweed derivatives such as irish moss and alginates and water soluble cellulose derivatives such as hydroxyethyl cellulose and sodium carboxymethyl cellulose can be used for this purpose. Desirably those materials are employed which are most compatible with stannous and fluoride ions. Binders which have no ionic groups such as hydroxyethyl cellulose are especially preferred. Improvements in texture can also be attained by including an additional material such as colloidal magnesium aluminum silicate.
  • Dentifrices conventionally contain sudsing agents, although these are not critical in the practice of the present invention. Any of the commonly used sudsing agents can be used if they are reasonably stable and form suds within the pH range of the dentifrices of this invention.
  • suitable sudsing agents include, but are not limited to, water-soluble alkyl and alkyl ether sulfonate and sulfates having alkyl groups of from about 8 to 18 carbon atoms, such as sodium lauryl sulfate, water-soluble salts of sulfonated monoglycerides of fatty acids having from 10 to 18 carbon atoms, such as sodium coconut monoglyceride sulfonate, salts of fatty acid amides of taurines such as sodium-N-methyl-N-palmitoyl tauride, salts of fatty acid esters of isethionic acid, and substantially saturated aliphatic acyl amides of saturated aliphatic monoaminocarboxylic acids having 2
  • dentifrices of this invention by weight of dentifrice, can be used in dentifrices of this invention.
  • humectant material in a toothpaste to keep it from hardening.
  • Materials commonly used for this purpose include glycerine, sorbitol, and other polyhydric alcohols.
  • Flavoring materials which can be included in toothpaste formulations include small amounts of oils of wintergreen and peppermint and sweetening agents such as saccharin, dextrose and levulose.
  • the dentifrice compositions of this invention will preferably contain a quantity of an amine trifluorostannite sufiicient to provide at least about 100 p.p.m. of fluoride ions but not more than 4000 p.p.m. total fluorine.
  • compositions for caries prophylaxis containing the amine trifluorostannites of this invention were prepared. Each composition was formulated to provide a compatible milieu for the active agent.
  • pH 4.8 (measurement made on a slurry made up of 1 part paste and 3 parts distilled water by volume).
  • the above composition possesses excellent consumer characteristics and eifectively reduces the solubility of dental enamel in acid.
  • This toothpaste will substantially reduce the incidence of dental caries when used in conjunction with a program of sound oral hygiene and regular professional care.
  • the amine trifluorostannite employed in this example can be replaced with equimolar quantities of dodecanolamine trifiuorostannite, diethanolamine trifluorostannite or triethanolamine trifluorostannite without loss of anticaries effect or impairment of consumer characteristics.
  • a mouthwash which constitutes another embodiment of this invention, is prepared having the following formulation.
  • This composition when retained in the oral cavity 1 to 2 minutes each day constitutes an effective caries prophylactic.
  • Any of the other amine trifluorostannites disclosed herein or mixtures thereof can be used in place of dodeoylamine trifluorostannite.
  • 0.2% of propylamine trifluorostannite, octylamine trifluorostannite or tetradecylamine trifiuorostannite can be used in the foregoing composition with no substantial change in activity.
  • the composition maintains its anticaries activity over a long period of time.
  • a tooth powder embodying the invention is formulated as follows:
  • This formulation is effective in caries prophylaxis, has good consumer characteristics, and remains active for long periods of time.
  • the trifluorostannite salt employed in this example can be replaced with equimolar quantities of any of the t-rifluorostannite salts listed in column 2 with no significant change in anticaries activity.
  • compositions which are usually applied by the dentist also constitutes embodiments of this invention.
  • dental prophylaxis pastes employed by dentist in cleaning teeth and containing the usual pumice and flavoring components can be formulated to contain in addition, 7.2% of methyldiethanolamine triiiuorostannite, trimethylamine trifluorostannite, diisopropanolamine trifluorostannite, dodecylaminoethyl trifluorostannite, or ethylene diamine trifluorostannite.
  • the pH of the composition is adjusted to 6.0 with a citric acid-sodium citrate buffer solution.
  • Such compositions employed in the usual manner by the dentist are of exceptional value in caries prophylaxis.
  • Aqueous solutions of the amine trifluorostannite salts of this invention designed to be topically applied to the teeth by the dentist are also etficacious compositions for caries prophylaxis.
  • Such compositions can also contain flavoring materials and the like.
  • the concentration of the trifluorostannite salts of amines in such a composition is within the range from about 0.14% to about 7.0% and the pH of the solution is the range from about 3.5 to about 6.0.
  • compositions of this invention can contain, in addition to the usual components of such formulation, functional adjuvants such as antibacterial, deodorizing and medicinal agents.
  • An oral composition for caries prophylaxis comprising an amine trifluorostannite having the formula:
  • R R and R are each members selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, and aminoalkyl groups, at least one of said Rs being one of said groups containing from about 1 to about 18 carbon atoms, the total carbon content of said groups being less than 30 carbon atoms in a quantity sufficient to provide at least about p.p.m. of fluoride ions but not more than 7500 p.p.m. total fluorine, and a fluoride compatible abrasive, the pH of said composition being within the range from about 3.5 to about 6.0 in aqueous solution.
  • composition of claim 1 wherein the amine trifluorostannite is N-octadecyl-N-hydroxyethyl-N-di(hydroxyethyl)-propylene diamine trifinorostannite.
  • composition of claim 1 wherein the amine trifluorostannite is monoethanolamine trifluorostannite.
  • composition of claim 7 4.
  • OTHER REFERENCES 5 The composition of claim 1 wherein the amine trifluorostannite is triethanolaminee trifiuorostannite.

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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)
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  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)
US227044A 1962-09-28 1962-09-28 Trifluorostannite salts of amines in oral compositions for caries prophylaxis Expired - Lifetime US3201316A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011663A1 (en) * 1978-12-01 1980-06-11 Unilever Plc Toilet and dental preparations and their use for oral and dental hygiene
US4430324A (en) 1981-11-27 1984-02-07 Lever Brothers Company Ammonium fluorometallate containing compositions
US4578489A (en) * 1982-06-10 1986-03-25 Ciba-Geigy Corporation Ammonium stannates-(IV)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2836544A (en) * 1955-02-07 1958-05-27 Indiana University Foundation Stannous chlorofluoride, method of preparing same, and dentifrice compositions therewith
US3070615A (en) * 1960-04-15 1962-12-25 Seyferth Dietmar Novel organo tin compounds
US3083143A (en) * 1957-07-13 1963-03-26 Gaba Ag Fluorides of organic bases as well as of amphoteric compounds, a method for their preparation, including the application of such new compounds in the caries prophylaxis, new dentifrices and mouth washes as well as a method for their preparation
US3085102A (en) * 1959-04-15 1963-04-09 Nippon Catalytic Chem Ind Process for producing alkyl tin halide compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2836544A (en) * 1955-02-07 1958-05-27 Indiana University Foundation Stannous chlorofluoride, method of preparing same, and dentifrice compositions therewith
US3083143A (en) * 1957-07-13 1963-03-26 Gaba Ag Fluorides of organic bases as well as of amphoteric compounds, a method for their preparation, including the application of such new compounds in the caries prophylaxis, new dentifrices and mouth washes as well as a method for their preparation
US3085102A (en) * 1959-04-15 1963-04-09 Nippon Catalytic Chem Ind Process for producing alkyl tin halide compounds
US3070615A (en) * 1960-04-15 1962-12-25 Seyferth Dietmar Novel organo tin compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0011663A1 (en) * 1978-12-01 1980-06-11 Unilever Plc Toilet and dental preparations and their use for oral and dental hygiene
US4430324A (en) 1981-11-27 1984-02-07 Lever Brothers Company Ammonium fluorometallate containing compositions
US4578489A (en) * 1982-06-10 1986-03-25 Ciba-Geigy Corporation Ammonium stannates-(IV)

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